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1
Namijo, S. N. "Carbon dioxide hydrogenation over supported metal catalysts." Thesis, Brunel University, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.379411.
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ELHUSSIEN, HUSSIEN Eldod. "NON- CATALYTIC TRANSFER HYDROGENATION IN SUPERCRITICAL CO2 FOR COAL LIQUEFACTION." OpenSIUC, 2014. https://opensiuc.lib.siu.edu/theses/1409.
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This thesis presents the results of the investigation on developing and evaluating a low temperature (<150oC) non - catalytic process using a hydrogen transfer agent (instead of molecu-lar hydrogen) for coal dissolution in supercritical CO2. The main idea behind the thesis was that one hydrogen atom from water and one hydrogen atom from the hydrogen transfer agent (HTA) were used to hydrogenate the coal. The products of coal dissolution were non-polar and polar while the supercritical CO2, which enhanced the rates of hydrogenation and dissolution of the non-polar molecules and removal from the reaction site, was non-polar. The polar modifier (PM) for CO2 was added to the freed to aid in the dissolution and removal of the polar components. The addition of a phase transfer agent (PTA) allowed a seamless transport of the ions and by-product between the aqueous and organic phases. DDAB, used as the PTA, is an effective phase transfer catalyst and showed enhancement to the coal dissolution process. COAL + DH- +H2O COAL.H2 + DHO-- This process has a great feature due to the fact that the chemicals were obtained without requir-ing to first convert coal to CO and H2 units as in indirect coal liquefaction. The experiments were conducted in a unique reactor set up that can be connected through two lines. one line to feed the reactor with supercritical CO2 and the other connected to gas chromatograph. The use of the supercritical CO2 enhanced the solvent option due to the chemical extraction, in addition to the low environmental impact and energy cost. In this thesis the experiment were conducted at five different temperatures from atmos-pheric to 140°C, 3000 - 6000 psi with five component of feed mixture, namely water, HTA, PTA, coal, and PM in semi batch vessels reactor system with a volume of 100 mL. The results show that the chemicals were obtained without requiring to first convert coal to CO and H2 units as in indirect coal liquefaction. The results show that the conversion was found to be 91.8% at opti-mum feed mixtures values of 3, 1.0 and 5.4 for water: PM, HTA: coal, water: coal respectively. With the oil price increase and growing in energy demand, the coal liquefaction remain afforda-ble and available energy alternative.
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Afonso, Joana da Costa Franco. "Catalytic hydrogenation of carbon dioxide to form methanol and methane." Master's thesis, Faculdade de Ciências e Tecnologia, 2013. http://hdl.handle.net/10362/10854.
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Gaikwad, Rohit. "Carbon Dioxide To Methanol: Stoichiometric Catalytic Hydrogenation Under High Pressure Conditions." Doctoral thesis, Universitat Rovira i Virgili, 2018. http://hdl.handle.net/10803/586089.
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El CO2 en la atmósfera aumenta a raíz del empleo de combustibles fósiles. La hidrogenación de CO2 ofrece una ruta
única para transformar esta molécula en productos químicos o combustibles como el metanol. El uso de alta presión
en el ratio CO2:H2 = 1:>3 permite incrementar la cinética de la reacción, alcanzando así la conversión termodinámica
como ya se ha reportado. No obstante, el mayor inconveniente del mencionado proceso es el tratamiento del
hidrógeno sin reaccionar. Por ello, se evaluaron las ventajas de realizar la reacción a alta presión en condiciones
estequiométricas (CO2:H2=1:3) examinando diferentes parámetros. Una vez optimizados, se alcanzó el límite
termodinámico y se obtuvo un valor de conversión de CO2 cercano al 90% con una selectividad para metanol > 95%
a 280 °C y 442 bar empleando Cu/ZnO/AlO3 como catalizador. Al minimizar las limitaciones de transferencia de
masa, el rendimiento fue de 15.6 gMeOH gcat-1 h-1, aproximadamente un orden de magnitud mayor comparado con
los de bibliografía. Adicionalmente, los mecanismos de la reacción en condiciones de alta presión se estudiaron
mediante análisis espacial de la fase gas por CG y espectroscopía Raman. El estudio mostró que el CO2 se convierte
directamente a metanol a baja temperatura, mientras que a alta temperatura la reacción water-gas shift es
predominante generando CO, que produce metanol posteriormente. estructura core-shell. Este material mostró un recubrimiento uniforme del ZnO en los cores de Cu, y el espesor del
shell se optimizó. Dichos nanomateriales mostraron alta actividad catalítica, útil para comprender la interacción entre
Cu y Zn y en concreto, las exclusivas fases de Zn formadas durante la reacción a alta presión mediante operando
DRX a alta presión.Carbon dioxide concentration in the atmosphere is continuously increasing as a consequence of the combustion of fossil fuels. CO2 hydrogenation offers a unique path to transform the chemically stable CO2 to useful chemicals or fuel such as methanol. High-pressure advantages under over-stoichiometric CO2:H2 ratio (1:>3) has been reported previously by drastically increasing the reaction kinetics and even reaching the thermodynamic conversion. However, the major drawback of such processes is the treatment of unreacted hydrogen. Reflecting this background, the advantages of the high pressure approach in stoichiometric CO2:H2 (1:3) ratio were critically evaluated by examining different reaction and process parameters. When optimized, we could reach the thermodynamic limit and obtained about 90% CO2 conversion with >95% methanol selectivity at 280 °C and 442 bar using Cu/ZnO/Al2O3 catalyst. When the mass transfer limitation was minimized, an outstanding weight time yield was achieved with 15.6 gMeOH gcat-1 h-1, which is about one order of magnitude higher than the state-of-the-art values. Furthermore, the reaction mechanisms under high-pressure reaction conditions were studied by spatially-resolved gas phase analysis through the axial direction of the catalytic reactor by GC and Raman spectroscopy.
5
Hasan, Tanvir. "NON-CATALYTIC TRANSFER HYDROGENATION IN SUPERCRITICAL CO2 FOR COAL LIQUEFACTION AND GRAPHENE EXTRACTION." OpenSIUC, 2015. https://opensiuc.lib.siu.edu/theses/1742.
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The paper discusses a two-step process for the simultaneous extraction of graphene quantum dots and chemicals. The two steps are sequential structure disruption by supercritical CO2 explosion followed by a low temperature (120oC), non-catalytic transfer hydrogenation in supercritical CO2. The key idea of this research is, one hydrogen atom from hydrogen transfer agent (HTA) one hydrogen atom from water is used to hydrogenate the coal. The use of supercritical CO2 enhances the rate of hydrogenation, helps in dissolution of non-polar molecules and removal from the reaction site. The coal dissolution products are polar and non-polar. A phase transfer agent (PTA) allows seamless transport of the ions and byproduct between the aqueous and organic phases. A polar modifier (PM) for CO2 has been added to aid in the dissolution and removal of the polar components. The effect of feed conditions on the liquefaction process has been investigated. The response metrics considered were the conversion of coal and the yields of various organic classes such as ketones, alkanes, alkenes, aliphatic acids, alcohols, amines, aromatics and aromatic oxygenates. Ketones were found to be the major constituent of the products. Graphene quantum dots were also extracted.
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Bansode, Atul Baban. "Exploiting high pressure advantages in catalytic hydrogenation of carbon dioxide to methanol." Doctoral thesis, Universitat Rovira i Virgili, 2014. http://hdl.handle.net/10803/135008.
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The aim of this thesis was to develop highly efficient CO2 hydrogenation process towards methanol by making use of high pressure approach. A high pressure lab scale plant was developed to conduct CO2 hydrogenation up to 400 bar. High pressure and low temperature were found to be the favourable conditions to excellent catalytic activity. Improved reaction performance towards methanol synthesis and reverse water-gas shift reaction was observed for the Ba and K promoted Cu/Al2O3 catalysts, respectively. Almost complete one-pass conversion of CO2 into methanol was observed under optimized process conditions over coprecipitated Cu/ZnO/Al2O3 catalysts. One-step transformation of CO2 into dimethyl ether was achieved with excellent catalytic activity. Selective formation of alkane or alkene was obtained by varying pressure of the secondary reactor coupled with methanol synthesis reactor. A high pressure, high temperature capillary cell for in-situ XAS was developed having capability for combined XAFS-Raman experiments under high pressure conditions.El propòsit d’aquesta tesis va ser desenvolupar un procés altament eficient per a la hidrogenació de CO2 a metanol, mitjançant l’ús de micro-reactors d’alta pressió. Una planta d’alta pressió va ser desenvolupada per a dur a terme la hidrogenació de CO2 fins a 400 bar. Una millora en el rendiment de la reacció cap a la síntesis de metanol i cap a la reacció inversa del desplaçament del gas d’aigua va ser observada per als catalitzadors de Cu/Al2O3 promocionats amb Ba i K, respectivament. Conversió, gairebé completa de CO2 a metanol, en una etapa, va ser observada en les condicions de procés optimitzades utilitzant catalitzadors de Cu/ZnO/Al2O3. Transformació de CO2 a dimetil-èter, alcans i alquens en una sola etapa de reacció, tot mantenint la conversió de CO2 elevada. Una cel•la capil•lar d’alta pressió i alta temperatura, per a mesures espectroscòpiques de raig-X in-situ, va ser desenvolupada.
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Parent, John Scott. "Catalytic hydrogenation of butadiene copolymers." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1997. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp04/nq21378.pdf.
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Willoughby, Christopher Alan. "Catalytic hydrogenation using titanium complexes." Thesis, Massachusetts Institute of Technology, 1995. http://hdl.handle.net/1721.1/11382.
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Yu, Jinquan. "Mechanistic investigation into catalytic hydrogenation." Thesis, University of Cambridge, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.621759.
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Sutherland, Luke Malcolm. "Catalytic mild hydrogenation of pygas." Thesis, University of Glasgow, 2018. http://theses.gla.ac.uk/8687/.
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In the production of ethylene and propylene via steam cracking, one of the major by-products is pygas. This mixture has a high octane number, owing to the large quantity of aromatics, diolefins, and olefins present within this mixture. This stream contains, in particular, a significant quantity of benzene and toluene. This is a waste product, but is currently heavily utilised for the extraction of benzene, mainly in order to produce styrene, cumene, and cyclohexane. While the demand for these compounds will continue to increase, the usage of pygas products will decrease in terms of its other main use, as a petrol additive, due to the increasingly strict regulation regarding the total allowable content of aromatics in fuel. When attempting to refine pygas for use as an aromatic chemical feedstock, the most common method of purification is to perform a hydrocracking reaction. Reactions will usually be carried out in two steps; the first is to hydrogenate the diolefins and styrene over, typically, a Pd-alumina catalyst under mild conditions. The second stage involves hydrogenating olefins, removing sulfur compounds by converting them into H2S, acid-catalysed ring opening of napthenics, and cracking paraffins. The aim of this research was to perform an analysis of the effect of reaction mixture on the retention of benzene when passed over an industrially-used bifunctional metal/zeolite hydrocracking catalyst, and to analyse the carbon laydown and other relevant effects produced by altering the reaction mixture. Previous work looking at pygas has mostly been carried out using only one, or a few, reaction compounds for simplicity of analysis. A number of studies use only styrene as a model for pygas. This is an excessively simplistic model of the reaction, and neglects the interactions between the various components of pygas present in a real reaction setting. Therefore, within this research, a mixture of alkanes, cycloalkanes, and aromatics are used to make a model reaction feed. These were reacted over the hydrocracking metal/zeolite catalyst, and an as-prepared zeolite catalyst. This reaction mixture model is more comprehensive in scope than most research performed, without also including olefins, which would accelerate coking of the catalyst, therefore obscuring the more basic interactions between aromatic and saturated paraffin compounds. The efficacy of each reaction mixture was measured by running a model feed based on common pygas compositions in industry, then running reactions in which a single one of four of the the six feed components was removed from the mixture. When the as-prepared zeolite support was used as a catalyst it was found to crack more of the aromatics, benzene and toluene, along with producing significantly more xylenes due to disproportionation, than the metal/zeolite catalyst. One of the main causes of catalyst deactivation in hydrocracking catalysts is coking, due to carbon deposition. The effect of coking was analysed using thermogravimetric analysis (TGA) ex-situ, which was also verified using CHN analysis. The as-prepared zeolite support was found to produce more carbon laydown than the metal/zeolite catalyst, although it is unclear if the difference would have a significant effect during longer reactions. Within the two groups of catalyst, metal/zeolite and zeolite, the total quantity of coke detected for each reaction mixture was found to show some variation, but would be similar. Some of the reaction mixtures showed a difference in product composition in the offline GC results, although the cause of this is unclear. The results in these reactions cannot, therefore, be anticipated based upon a simple addition-subtraction model in terms of feed components, as there appears to be a complex interdependence between these components that influences the final retention of products observed, that was not assumed to be present before this work was carried out. Analysis of the coke deposit by Raman spectroscopy revealed that the graphite platelets in all reactions were between 10 and 13 nm. Therefore, it appears coke deposition was observed only on the external surface of the catalyst.
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McGregor, James. "Heterogeneous catalytic hydrogenation and dehydrogenation : catalysts and catalytic processes." Thesis, University of Cambridge, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.612796.
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Glennie, Sarah. "Catalytic hydrogenation of nitriles to amines." Thesis, Cardiff University, 2006. http://orca.cf.ac.uk/54626/.
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The adiponitrile hydrogenation reaction, relevant for the production of aminocapronittile and hexamemyldiamine precursors for Nylon 6 and Nylon 6, 6 respectively, has been investigated. Three different reactor systems were used trickle-bed reactor, fixed-bed gas-phase reactor and the stirred-tank autoclave reactor. This meant comparisons between flow system and batch process could be made. Supported metal catalysts were investigated as alternatives for the currendy industrially used Raney catalyst. Precious metals, specifically rhodium, were compared with the base metals nickel and cobalt on the basis of activity and selectivity. Mixed metal alloy catalysts were also prepared and comparisons drawn. Finally a range of supports were also tested. Both flow systems were found to be of limited use with problems attributed to the practical applications of the reactor systems. Using Autoclave activity data as a standard it was possible to define differences in activity between each of the catalysts prepared.
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Shermer, Duncan J. "Sequential reactions involving catalytic transfer hydrogenation technology." Thesis, University of Bath, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.432384.
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Musadi, Maya Ramadianti. "Catalytic hydrogenation of CO₂ for sustainable transport." Thesis, University of Manchester, 2009. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.505377.
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C02 emissions are one of the main causes of the greenhouse effect. Reactions between C02 and H2, such as methanol synthesis and methanation, could play an important role in reducing these emissions. The low methanol yield, both selectivity and conversion, is the main problem in the methanol synthesis. Methanation could be considered as another alternative process, because recent research showed that the yield in methanation'process is high, the conversion of C02 to C~ was nearly 100%. By using a combination of the Zero Emission Petrol Vehicle (ZEPV) concept, catalytic hydrogenation of CO2 and methanol to gasoline (MTG) process gasoline can be re-synthesised from recycle C02. The objectives of this thesis are to examine the methanol sY!lthesis behaviour in the lab scale tubular catalytic reactor, to investigate the effect of molecular Sieve 4A (MS 4A) on this synthesis and to analyse the feasibility study for a re-syn fuel refinery. First, methanol synthesis experiments were performed on a CuO/ZnO/AhOJ catalyst at 190- 2200 C, 1 bar, 3600 - 7200 h-I and H2/C02 = 3 - 4. The results indicated that methanol was produced from reaction between H2 and CO2 at those conditions. A maximum C02 conversion was reached at 1900 C, 1 bar, 3600 h-I and H2/C02 = 4. The numerical model results predicted that the initial rate of methanol synthesis increase sharply at pressures into 50 atm and is then relativ~ly constant at pressures above 50 atm. At 50 atm, the initial rate ratio is predicted to increase 35 - 45 times than the initial rate at 1 atm. The presence of water is one of the problems affecting the synthesis. Then to investigate the effect of adding a desiccant, methanol synthesis using a CuO/ZnO/AhOJ catalyst and a MS 4A were carried out at the conditions with the maximum CO2 conversion. The results showed that MS 4A adsorbed water hence the conversion of C02 increased from 1.13% to 2.12%. According to the numerical model, these conversions are predicted 35 - 45 times at pressure around 50 atm. Finally, material and energy balances were calculated for four possible chemical pathways for this re-synthesis (the direct CO2 hydrogenation, the Camere process, the methane to methanol process and the electrolysis process) to determine energy requirements in the re-syn fuel refineries. By using the ZEPV concept, some 70 MT/year of C02 from the combustion of about 22 MT/year of gasoline in around 30 million vehicles in UK can be liquefied at 70 bar and stored on board. This liquid C02 is available to be converted back to gasoline via methanol. The 30% conversion, which was obtained from combination of experiment and numerical model results, was applied for direct hydrogenation of CO2. For the other chemical pathways, the conversion used was based on previous studies. Carrying out this recycling in a set of geographically distributed 're-syn fuel' refineries using offshore wind energy has no further requirement for exploration of crude oil, no limitation of raw material and furthermore no cost penalty for the emitted carbon value. The economic analysis shows that the present (2008) forecourt price for the typical oil refinery (98 p/l) is lower than this forecourt price for the 're-syn fuel' refinery using the offshore wind energy (l09 p/l). By predicting that the wind energy cost will be reduced to as Iowa 2.5 plkWh in the future (2020), it is estimated that the forecourt price of gasoli~e from this futuristic sustainable resynthesis refinery would be decreased to 89 p/l. This forecourt price is cheaper than the current gasoline forecourt price from a typical conventional oil refinery. Based on this preliminary economic assessment, gasoline re-synthesis from recycled CO2 using offshore wind energy is both perfectly sustainable and almost competitive for today and will be cheaper than gasoline from crude oil in the future.
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Zhao, Haiyan. "Catalytic Hydrogenation and Hydrodesulfurization of Model Compounds." Diss., Virginia Tech, 2009. http://hdl.handle.net/10919/26526.
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This dissertation describes two related studies on hydrogenation and hydrodesulfurization of heterocyclic S-containing compounds.
Alkyl substituted thiophenes are promising candidates for hydrogen carriers as the dehydrogenation reactions are known to occur under mild conditions. Four types of catalysts including supported noble metals, bimetallic noble metals, transition metal phosphides and transition metal sulfides have been investigated for 2-methylthiophene (2MT) hydrogenation and ring opening. The major products were tetrahydro-2-methylthiophene (TH2MT), pentenes and pentane, with very little C5-thiols observed. The selectivity towards the desired product TH2MT follows the order: noble metals > bimetallics > phosphides > sulfides. The best hydrogenation catalyst was 2% Pt/Al2O3 which exhibited relatively high reactivity and selectivity towards TH2MT at moderate temperatures. Temperature-programmed desorption (TPD) of hydrogen indicated that the H2 desorption amount was inversely related to the rate of TH2MT formation. Temperature programmed reaction (TPR) experiments revealed that pentanethiol became the major product, especially with HDS catalysts like CoMoS/Al2O3 and WP/SiO2, which indicates that poisoned or modified conventional HDS catalysts would be good candidates for further 2MT hydrogenation studies.
The role of tetrahedral Ni(1) sites and square pyramidal Ni(2) sites in Ni2P hydrotreating catalysts was studied by substitution of Ni with Fe. The Fe component was deemed as a good probe because Ni2P and Fe2P adopt the same hexagonal crystal structure, yet Fe2P is completely inactive for hydrodesulfurization (HDS). For this purpose a series of NiFeP/SiO2 catalysts were prepared with different Ni:Fe molar ratios (1:0, 3:1, 1:1, 1:3, and 0:1) and investigated in the HDS of 4,6-dimethyldibenzothiophene at 300 and 340 oC. The uniformity of the NiFe series was demonstrated by x-ray diffraction analysis and by Fourier transform infrared (FTIR) spectroscopy of adsorbed CO. The position of substitution of Fe was determined by extended X-ray absorption fine structure (EXAFS) analysis. It was found that at 300 oC the HDS activity of the catalysts decreased with increasing Fe content and that this could be explained by the substitution of Fe at the more active Ni(2) sites. As temperature was raised to 340 oC, the activity of the Fe-containing samples increased, although not to the level of Ni2P, and this could be understood from a reconstruction of the NiFe phase to expose more Ni(2) sites. This was likely driven by the formation of surface Ni-S bonds, which could be observed by EXAFS in spent samples.Ph. D.
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Savourey, Solene. "Nouveaux procédés de réduction catalytique du CO2 en consommables chimiques." Thesis, Université Paris-Saclay (ComUE), 2016. http://www.theses.fr/2016SACLV051/document.
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L’utilisation des ressources fossiles a permis l’industrialisation de notre société, cependant, après 200 ans de consommation effrénée, notre dépendance nous oblige à faire face à plusieurs défis. 1) Capter et stocker/valoriser le CO2 pour limiter le relargage massif de CO2 dans l’atmosphère 2) Trouver une nouvelle source de carbone pour la synthèse de produits chimiques afin de réduire la pression mise sur les réserves de ressources fossiles 3) Développer des nouveaux moyens de stockage de l’énergie pour pouvoir se reposer sur les énergies renouvelables intermittentes. Le CO2 étant une source de carbone abondante et peu chère il peut être utilisé comme brique moléculaire pour la synthèse de produits chimiques et être ainsi valorisé. De plus il peut également être utilisé notamment via le coupleCO2/MeOH pour le stockage de l’énergie. Cependant peu de procédés utilisant le CO2 sont actuellement déployés à l’échelle industrielle car la barrière cinétique associée à la réduction du CO2 entraîne de faibles rendements faradiques et les produits accessibles directement à partir de celui-ci sont peu nombreux.En s’inspirant de la Nature nous avons voulu, au cours de cette thèse, développer des réactions à partir de molécules facilement et directement accessibles à partir du CO2 afin de s’affranchir des limitations liés à ce dernier. Nous avons donc développé plusieurs réactions catalytiques à partir de l’acide formique et du monoxyde de carbone qui sont les principaux dérivés du CO2. Nous avons notamment étudié la réduction du CO2 en méthanol en utilisant l’acide formique comme réducteur et nous avons appliqué cette réactivité pour la méthylation des amines. Enfin nous avons également utilisé le CO comme relais pour la synthèse de liaison C–C à partir du CO2. Cette stratégie a été prouvée pour la synthèse d’alkylamines avec de longues chaînes alkyl à partir de CO et d’un réducteurFossil resources have been extensively used for the past 200 years allowing a fast paced industrializationin our society. However we are facing today several challenges to preserve our way of life 1) CO2 shouldbe captured and stored/used to avoid large quantity of CO2 to be released in the atmosphere 2) Bypassthe use of fossil resource by using another source of carbon for the synthesis of chemicals 3) Developefficient energy storage technologies to rely more on renewable intermittent energy sources. As CO2 is acheap widely available resource, this waste could be used as well as a source of carbon for the synthesisof value added chemicals but also as a way to store energy in the tandem CO2/MeOH. However as it isan inert gas few processes using CO2 have been industrialized so far.Inspired by Nature’s way to use CO2 we decided to design new reactions from carbon monoxide andformic acid, two derivatives easily available from CO2 that could enable us to overcome the limitationwe faced with CO2. We therefore studied the transformation of CO2 to methanol using formic acid as anintermediate and a reductant and we subsequently used this reaction to perform the methylation ofaromatic amines using formic acid. Finally we developed a new reaction of amines homologation withcarbon monoxide allowing the formation of several C–C bonds
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Islam, Aunul. "Catalytic hydrogenation of model coal extract mid-distillates." Thesis, Imperial College London, 1986. http://hdl.handle.net/10044/1/38048.
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McEwan, Lynsey. "Selective catalytic hydrogenation for industrial 1-hexene purification." Master's thesis, University of Cape Town, 2010. http://hdl.handle.net/11427/10852.
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Includes abstract.Includes bibliographical references (leaves 79-82).
Linear alpha-olefins, including 1-hexene, are used mainly as co-monomers in the production of polymers. The very low tolerance of the polymerisation catalyst to highly unsaturated impurities makes removal of these impurities from the olefin feedstock crucial. In South Africa, linear alpha-olefins are a major product of Fischer-Tropsch synthesis. A complex extractive distillation process is used to separate impurities from the product stream. A final polishing step by adsorption results in a significant loss of valuable alpha-olefin.
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Khan, Zaffer. "Catalytic hydrogenation in a cocurrent downflow contactor reactor." Thesis, University of Birmingham, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.588602.
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In order to investigate the full mass transfer potential of the CDC reactor as a three phase chemical reactor, model reactants were hydrogenated in the CDC operating as a packed bed and slurry reactor. Two model reactants, itaconic acid and 3-nitrobenzoic acid were chosen for study and hydrogenated using a 5% PdlC catalyst for all slurry reactions and a commercially prepared 3 w/w% PdlA1203 catalyst for all packed bed reactions. To further enhance the mass transfer capabilities of the CDC, swirlflow was fitted to the lower region of the column for both packed bed and slurry reactors. For all model hydrogenation reactions, the transport parameters were evaluated and compared for the different reactor configurations enabling evaluation of the mass transfer capabilities of the CDC reactors. Two very different reactions of commercial significance were studied in the CDC firstly, the consecutive hydrogenation of 2-butyne-l ,4-diol a possible reaction stage in the production of vitamin B 12 and the hydrogenation of soyabean oil, an essential step necessary for the production of margarine. For butynediol hydrogenation, substrate inhibition occurred, preventing the full capabilities of the CDC to be utilised. For comparison with reaction in the CDC, butynediol was hydrogenated in a small stirred reactor and comparable rates of reaction were observed. Soyabean oil was hydrogenated in both packed bed and slurry modes and showed comparable rates of reaction between the two different reaction modes. From the evaluated transport parameters and reaction kinetics, the CDC operated in both packed bed and slurry modes achieved reaction which was occurring under diffusion resistance free conditions, whereas normally soyabean oil is hydrogenated in conditions which are limited by resistances to diffusion. For both reaction modes, high linolenic selectivities were achieved. This study has shown that the CDC is suitable for use as a three phase chemical reactor providing a high degree of chemical reaction which is not limited by resistances to mass transfer. The CDC is particularly suitable for reactions were efficient mass transfer is required with chemical reaction.
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Wierzbicki, Dominik. "New nano-oxide catalysts for CO2 hydrogenation reaction." Thesis, Sorbonne université, 2019. http://www.theses.fr/2019SORUS420.
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L’augmentation de la concentration de CO2 dans l'atmosphère, considérée comme l'une des sources anthropiques du réchauffement de la planète, suscite de plus en plus d'inquiétudes et une prise de conscience sociale face au changement climatique. Les stratégies de réduction des émissions de CO2 peuvent être divisées en deux groupes (i) capture et stockage du carbone (CCS) et (ii) capture et utilisation du carbone (CCU). En comparaison avec le CCS, les technologies CCU permettent de convertir le dioxyde de carbone en un produit valorisé. Ainsi, les méthodes CCU traitent le CO2 en tant que matière première et non en tant que polluant. Parmi les processus convertissant le CO2 en un composé valorisé, on trouve la méthanation du dioxyde de carbone. Dans ce processus, le dioxyde de carbone est hydrogéné en méthane à l’aide de l'hydrogène provenant de l’électrolyse de l'eau en utilisant par exemple des excès d'énergie. Il convient de mentionner qu’une installation à l’échelle industrielle existe déjà (jusqu’à 10 MW). La littérature suggère que le nickel est le métal actif le plus approprié dans ce procédé en raison de (i) sa très bonne activité catalytique (comparable aux métaux nobles), (ii) un faible coût et (iii) une grande disponibilité. Dans la littérature, différentes stratégies ont déjà été mises en œuvre afin d'accroître l'activité des catalyseurs à base de Ni lors de la méthanation du CO2. Les plus courants incluent l’utilisation de divers supports, la modification de la teneur en nickel ou l’introduction de promoteurs. De telles stratégies modifient les propriétés physicochimiques telles que l'interaction entre la phase active au nickel et le support, ce qui inhibe le frittage et augmente la capacité d'adsorption du CO2. Ces deux propriétés sont essentielles afin d’obtenir un catalyseur à la fois actif et sélectif pour la méthanation du CO2. L’application d’oxydes mixtes de magnésie et d’alumine permet d’introduire ces propriétés car le MgO possède un caractère basique et est fortement lié au NiO en raison de la formation d’une solution solide de NiO-MgO. Les hydrotalcites semblent être les matériaux les plus prometteurs pour une telle application car NiO, MgO et Al2O3 peuvent être facilement introduits dans ceux-ci. La littérature a confirmé que les hydrotalcites contenant du Ni sont très actifs dans cette réaction. L'objectif de cette thèse était donc d'évaluer les propriétés catalytiques d'oxydes mixtes dérivés d'hydrotalcite contenant du Ni lors de la méthanation du CO2. Comme la revue de littérature a montré qu'il y avait peu d'études sur de tels matériaux pour cette réaction, ces travaux ont servi à combler ces lacunes. Ces travaux peuvent être divisé en quatre parties : (i) évaluation des propriétés catalytiques d’hydrotalcites contenant diverses quantités de nickel dans des couches de type brucite, (ii) évaluation des propriétés catalytiques d’hydrotalcites contenant du nickel activées à l'aide de Fe ou de La, (iii) évaluation de l'effet de la méthode d'introduction de La sur les propriétés catalytiques des Ni-hydrotalcites et (iv) optimisation des catalyseurs et examen de l'effet promoteur de La. Afin de corréler les modifications des propriétés physico-chimiques des matériaux préparés par co-précipitation, les catalyseurs ont été caractérisés par analyse élémentaire (ICP-MS ou XRF), DRX, IRTF, sorption de l’azote à basse température, H2-TPR et CO2-TPD. De plus, les catalyseurs sélectionnés ont été caractérisés par TEM, XANES et XES. Les tests catalytiques ont été effectués dans une plage de températures allant de 250°C à 450°C. Afin d'examiner l'effet de promotion de l'introduction du lanthane, les méthodes XANES et XES dans diverses conditions de réaction ont été mises en œuvre. (...)The increasing concentration of CO2 in the atmosphere, which is considered to be one of the anthropogenic sources of global warming, increased concerns and social awareness about the climate change. The strategies for CO2 emissions reduction may be divided into (i) carbon capture and storage (CCS) and (ii) carbon capture and utilization (CCU) groups. In comparison to CCS, the CCU technologies allow to convert carbon dioxide into a valuable product. Thus, CCU methods are treating CO2 as raw material and not as pollutant. Among the processes that convert CO2 into a valuable compound is carbon dioxide methanation. In this process carbon dioxide is hydrogenated to methane with hydrogen supplied via water electrolysis using e.g. excess energy. It should be mentioned that some industrial scale installation already exists (up to 10MW). The literature study suggests that the most appropriate active metal in this process is nickel due to (i) very good catalytic activity (comparable to noble metals), (ii) low cost and (iii) availability. As reported in literature, different strategies were implemented in order to increase the activity of Ni-based catalysts in CO2 methanation. The most common ones include using various supports, changing the content of nickel or introduction of promoters. These strategies change the physicochemical properties, such as interaction of nickel active phase with the support, which inhibits sintering and increases the CO2 adsorption capacity. The latter property , as well as stability towards sintering, are crucial in order to obtain an active, selective and stable catalyst for CO2 methanation reaction. The application of mixed oxides of magnesia and alumina allows to introduce these properties, as MgO possesses basic character and is strongly bonded with NiO due to the formation of a solid solution of NiO-MgO. Hydrotalcites seem to be the highly promising materials for such application, because NiO, MgO and Al2O3 may be easily introduced into such materials. Literature studies confirmed that Ni-containing hydrotalcites are very active in CO2 methanation. Therefore, the goal of this PhD thesis was to evaluate the catalytic properties of Ni-containing hydrotalcite-derived mixed oxide materials in CO2 methanation. As the literature review showed that there are not many studies focused on such materials in the mentioned field, this work was focused on filling these gaps. The work was divided into four parts: (i) evaluation of catalytic properties of hydrotalcites containing various amounts of nickel in brucite-like layers, (ii) evaluation of catalytic properties of nickel-containing hydrotalcites promoted with Fe or La, (iii) evaluation of the effect of different methods of introduction of La on catalytic properties of Ni-hydrotalcites, and (iv) optimization of the catalysts and examination of promoting effect of La. In order to correlate the changes of physico-chemical properties, of the materials prepared by co-precipitation, the catalysts were characterized by means of elemental analysis (ICP-MS or XRF), XRD, FTIR, low temperature nitrogen sorption, H2-TPR and CO2-TPD. Additionally, selected catalysts were characterized using TEM, XANES and XES. The catalytic tests were carried out in the temperature range from 250°C to 450°C. In order to elucidate the promoting effect of lanthanum introduction operando XANES and XES under various reaction conditions were implemented. (...)
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Cadu, Alban. "Iridium Catalysed Asymmetric Hydrogenation of Pyridines." Licentiate thesis, Uppsala universitet, Syntetisk organisk kemi, 2013. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-212413.
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This thesis presents the hydrogenation of substituted pyridines using N,P-ligated iridium catalystsin homogeneous media. These iridium catalysts were developed within this research group in thepast decade. This method of hydrogenation is highly stereoselective, and in several cases good to excellent ees were obtained.The hydrogenation of substituted pyridines was studied: by screening for the catalyst giving thehighest conversion and ee, by optimising the reaction conditions and by attempting to improve existingcatalysts. New substrates were synthesised for this process, in particular alkyl substituted Nprotectedpyridines. Their reduction provided chiral piperidines, which could be used as chiralbuilding blocks once deprotected.
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Diaz, Valenzuela Maria Belen. "New ruthenium catalysts for asymmetric hydrogenation." Thesis, University of St Andrews, 2007. http://hdl.handle.net/10023/479.
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A review on catalytic asymmetric hydrogenation of C=O double bonds is presented in the first chapter. Noyori’s pioneering research on ruthenium complexes containing both phosphine and diamine ligands using [i superscript]PrOH and [t superscript]BuOK is described, this system gave impressive highly chemeo-selectivity for C=O bonds and extremely high enantioselectivity for a range of acetophenone derivatives. Numerous groups have been inspired by Noyori’s catalyst of the type RuCl₂(chiraldiphosphine)(chiraldiamine), these systems often give excellent results for acetophenone. However, these catalysts have limitations, they are found to be either inactive or unselective for hydrogenation of tetralones, dialkylketones, bulky ketones, some heterocyclic ketones and imines prove difficult using this system. In this project, we are searching for a new catalyst for asymmetric hydrogenation of ketones that solve the difficult challenges faced when using Noyori’s [Ru(diphosphine)(diamine)Cl₂] catalysts system. Departing from Noyori’s type catalyst in the second chapter is described our effort to synthesise new diamines derived from amino acids and the synthesis of [Ru(diamine)(diphosphine)Cl₂] complexes. These catalysts are tested in asymmetric hydrgenation of ketones. In the next two chapters the finding of a new tridentate P N NH₂ type ligand is reported and the novel ruthenium complex containing the tridentate ligand has been synthesised and characterised by X-ray crystallography and been found to be active in the hydrogenation of a range of C=O and C=N double bonds, including the enantioselective hydrogenation of normally unreactive bulky ketones with up to 93 % ee. The last chapter explains the transfer hydrogenation activity for this new catalyst, involving a novel method of transfer hydrogenation reaction under microwave irradiation.
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Willett, Paul. "Heterogeneous catalytic hydrogenation and purification applied to commercial processes." Thesis, Durham University, 2002. http://etheses.dur.ac.uk/4099/.
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Three distinct chemical processes have been investigated, with the aim of producing high purity 1,5-pentanediol (PDO), 1,4-butanediol (BDO) and tetrahydrofurfuryl alcohol (THFA) and thereby improving the efficiency of their manufacture. The production of 1,5-pentanediol via the low-pressure vapour phase hydrogenation of 1,5-dimethylpentanedioate has been studied using a copper manganese heterogeneous catalyst system and found to be as good as the usually favoured copper chrome, which is now becoming difficult to operate commercially due to toxicity concerns. The optimum conditions were determined for a commercial process. The purification of the PDO produced, to the high standards dictated by polymer manufacture, has also been examined. Simple distillation was not possible because reactive oligomeric species were present. To overcome this, a reactive distillation scheme was developed and demonstrated experimentally. During the manufacture of 1,4-butanedlol, a by-product (4-hydroxybutyl)-2- tetrahydrofuran, known commercially as "Acetal", is formed during hydrogenation and proves very difficult to remove by conventional means. By conversion of this compound to more volatile species, by hydrogenation over a nickel catalyst, it was demonstrated that the purity of BDO obtained was greater than that previously possible.
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Samran, Jareerat Phinyocheep Pranee. "A study of non-catalytic hydrogenation of natural rubber." [S.l.] : [s.n.], 2005. http://cyberdoc.univ-lemans.fr/theses/2005/2005LEMA1022.pdf.
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Reproduction de : Thèse de doctorat : Physique : Bangkok : 2005. Reproduction de : Thèse de doctorat : Physique : Le Mans : 2005.Thèse soutenue en co-tutelle. Titre provenant de l'écran-titre. Bibliogr. p. 274-282.
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Fan, Xiaolei. "Selective catalytic hydrogenation in a structured compact multifunctional reactor." Thesis, University of Bath, 2010. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.519009.
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Selective hydrogenation is an important class of chemical reactions for the production of speciality chemicals, pharmaceuticals and petrochemicals. The challenges in this type of reactions are to control selectivity in hydrogenation of poly-functional molecules, and avoid the possible risk of reaction runaway due to the high exothermisity. In this project the fundamentals of liquid-phase hydrogenation reactions in a structured compact multifunctional reactor were investigated. This technology represents an advance over the existing hydrogenation technologies because it exploits the effects of reduced characteristic paths of mass and heat transfer, attained in compact reactor architecture with mm-scale reaction channels and integrated static mixers and micro-heat exchangers. Catalysts based on mesoporous synthetic carbons were developed especially for preparing micro-packed beds in the compact reactor. The investigation resulted in fundamental information on reactor performance for selected model reactions, heat transfer efficiency of the integrated micro-heat exchangers, development of continuous tandem reaction, and evaluation of developed catalysts for hydrogenation and hydrodehalogenation reactions under the continuous flow conditions being used. The results demonstrate that the structured compact multifunctional reactor might be a promising technology to transfer conventional heterogeneous catalysis to flow regime.
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Rouckout, Nicolas Julien. "Catalytic hydrogenation of an aromatic sulfonyl chloride into thiophenol." [College Station, Tex. : Texas A&M University, 2008. http://hdl.handle.net/1969.1/ETD-TAMU-2686.
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Samran, Jareerat. "A study of non-catalytic hydrogenation of natural rubber." Le Mans, 2005. http://cyberdoc.univ-lemans.fr/theses/2005/2005LEMA1022.pdf.
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Cette étude aborde l'hydrogénation du caoutchouc naturel dans un but de développement et de valorisation de cette substance largement produite dans le sud-est asiatique et en particulier en Thaïlande. En effet, ce composé est un polymère insaturé bien connu, possédant d'excellentes propriétés élastiques, mais sa résistance en température est nettement inférieure aux élastomères synthétiques. Dans ce travail, l'hydrogénation a été menée par voie non catalytique, en utilisant un agent intermédiaire de type diimide généré in-situ à partir de deux types de composés, à savoir i) la décomposition thermique du p-toluensulfonnylhydrazide (TSH) ainsi que ii) la réaction de l'hydrazine (N2H4) et l'hydroperoxide (H202) en présence d'un catalyseur. La structure des caoutchoucs hydrogénés a été analysée par différentes méthodes spectroscopiques : absorption infrarouge, diffusion Raman, RMN en phase liquide et solide. L'hydrogénation du caoutchouc naturel et de sa forme époxyde a été réalisée à l'aide de TSH dans une solution de xylène à l35°C. Un ratio molaire [TSH] :[C=C] de 2 a été choisi pour l'hydrogénation du caoutchouc naturel et de 4 formes époxydes contenant respectivement 10,22,30 et 40% d'époxyde. Les mesures quantitatives menées par les différentes techniques spectroscopiques sont toutes concordantes et indiquent une augmentation du taux d'hydrogénation avec le temps de réaction pour atteindre des valeurs limites proches de 90% pour un temps de réaction égal à 8h. L'isomérisation cis-trans a été observée par RMN en phase liquide et solide. En outre des réactions secondaires peuvent apparaître, dues aux températures élevées des protocoles utilisés. Dans le cas de l'utilisation de N2H4 et de H2O2, l'hydrogénation a été réalisée directement sur la forme latex du caoutchouc naturel, avec étude de l'influence de divers paramètres : temps de réaction, température, taux des réactifs. Le suivi du taux d'hydrogénation par RMN liquide montre que les meilleurs résultats sont obtenus pour des rapports équimolaires de N2H4 et de H2O2. Les caractéristiques moléculaires du caoutchouc naturel, de la forme époxyde à 10% et des différents composés hydrogénés a été complètement étudiée par diffusion Raman et RMN du carbone 13e. La diffusion Raman montre l'augmentation de la constante de force associée à la double liaison C=C en fonction du taux d'hydrogénation, qu'il est possible d'associer à un accroissement de la rigidité de la structure d'ensemble. L'étude thermique effectuée par DSC révèle une amélioration des propriétés des échantillons après hydrogénation tant en solution que pour les systèmes en phase aqueuse. La comparaison des propriétés de stabilité thermique des caoutchoucs naturels hydrogénés, par analyse thermogravimétrique, sous air ou sous atmosphère d'azote montre que la décomposition en température est plus faible sous air. De même les propriétés thermiques des formes époxydes ont été améliorées après hydrogénation. L'ensemble des matériaux également fait l'objet d'une étude rhéologique complète. Enfin la technique d'imagerie Raman révèle que l'hydrogénation est un processus aléatoire au moins à l'échelle micrométriqueHydrogenation is one of the most efficient methods to alter and improve the physical properties of unsaturated polymers and to produce a new material. The aim of this research is to transform partially the unsaturated part of natural rubber (NR) into saturated moiety in order to improve its thermal and oxidative properties and to widen its area of applications. In this study, non-catalytic hydrogenation process was applied by using diimide generated in situ from two types of hydrogenating agent i. E. Thermal decomposition of p-tolueriesulfonylhydrazide (TSH) and oxidation of hydrazine (N2H4) by hydrogen peroxide (H2O2). The chemical structure of the hydrogenated rubbers was analyzed by vibrational and resonance spectroscopies i. E. FTIR, Raman, 1H- and 13C-NMR. First, the hydrogenation of NR and its modified form as epoxidized NR (ENR) was performed by using TSH in xylene solution at 135°C. The molar ratio of [TSH]:[C=C] equal to 2 was used for hydrogenation of NR and four different types of ENR i. E. ENR-10, ENR-22, ENR-30 and ENR-40, containing 10, 22, 30 and 40% mole of epoxide content, respectively. The quantitative measurements on fraction of saturated units determined by Raman, 1H-NMR in liquid state and 13C-NMR in solid state gave similar results which indicated that percent hydrogenation increased with increasing reaction time and about 80-89 % hydrogenation was obtained at 8h. While in the case of ENRs, the percent hydrogenation is approximately 93-98%. Cis-trans isomerization was also observed by 1H-NMR in liquid state and 13C_NMR both in liquid and solid state. Sorne side reaction occurred i. E. Chain degradation of both NR and ENRs which might be due to a relatively high temperature process. In the case of hydrogenation of ENRs, formation of furan structure and fixation of p-toluenesulfinic acid (TSOH) by-product were detected by FTIR. For hydrogenation using (N2H4) and (H2O2), NR in the original form of latex was used. Various parameters affecting the hydrogenation reaction were investigated i. E. Reaction time and temperature, amount of reactants, and dry rubber content. The hydrogenation progress could be monitored by means of NMR in liquid state as function of reaction condition. The results indicated that the best result was obtained when equimolar ratio of (N2H4) and (H2O2) was used. With addition of varying hydrazine and hydrogen peroxide contents, the best condition of diimide reduction is achieved when their content is 1. 5 times the amount C=C of the rubber. Molecular characteristics in the NR, ENR-l 0 and the hydrogenated rubbers were investigated by Raman and 13C-NMR in solid state techniques. The relative variation force constant as analyzed by Raman spectroscopy tends to increase with the hydrogenation level. It might be suggested that the higher stiffness of the rubber chains upon hydrogenation is correlated to the increased relative variation force constants. In cross-polarization (CP) experiment of HNR and HENR, it was found that the rate of cross polarization of methyl carbon in HENR-30(8) is highest with respect to methyl carbon in HNR(8) and HENR-IO(8). It is clear that the methyl carbon of HENR-30(8) has the least mobility due to more furan units and chemical fixation of TSOH on the rubber chains. Thermal properties studied by a differential scanning calorimetry revealed thermal improvement after hydrogenation, both in solution and in aqueous systems. Comparison of the thermal stability using thermogravimetric analyzer, under air and nitrogen atmosphere, showed the decomposition temperature of HNR in air is lower than that in nitrogen atmosphere. The thermal stability of ENR was also enhanced after hydrogenation. Rheological properties of HNR samples measured using RPA rheometer exhibited the storage and loss moduli of HNR97 sample with the highest value compared to HNR38 and HNR69 samples. For instance, the fully hydrogenated NR has a significant increment in the loss and storage moduli of the samples. By using Raman mapping technique, it revealed that the hydrogenation of NR is a random process at the micron level
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Mahishi, Shreesha. "Rate Enhancement Of The Catalytic Hydrogenation Of An Unsaturated Ketone By Ultrasonic Irradiation." Thesis, Indian Institute of Science, 1996. http://hdl.handle.net/2005/138.
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The aim of the work was to develop an understanding of the phenomenon of rate enhancement observed when a heterogeneous catalytic reaction system is irradiated by ultrasound. The system under investigation was the catalytic hydrogenation of an a, B - unsaturated ketone, using zinc dust and aqueous nickel chloride as a source of hydrogen. When a slurry of zinc particles and aqueous nickel chloride is stirred or sonicated, nickel deposits in the form of patches on the surface of the zinc particles and simultaneously, zinc dissolves into the solution in the form of zinc ions, a process called pitting corrosion.
Hydrogen atoms are formed when hydrogen ions diffuse from the bulk, adsorb onto the nickel surface and take up electrons generated by the dissolution of zinc. Once the atoms are formed on the surface, the atoms combine to form hydrogen molecules, which desorb in the form of hydrogen gas. When ketone is added to this slurry, the hydrogen atom formed on the surface of nickel is used as the source of hydrogen for the hydrogenation reaction. In these processes, nickel serves as catalyst. The ketone first has to diffuse to the bulk, adsorb onto the surface of nickel and undergo reduction by the hydrogen atoms to form the product. The product then has to desorb from the surface and diffuse into the bulk, in order to create vacant sites on the nickel surface for the adsorption of more ketone.
Experiments dealing with measurements of hydrogen evolution rates pointed out that hydrogen is not a limiting reactant, since evolution was sustained for long periods of time. The evolution rates versus time data revealed that the nature of the plots for both, the stirred and sonicated systems were similar. These facts lead us to infer that the basic mechanism of nickel deposition, pitting corrosion, etc. was similar for the two cases.
To study the hydrogenation reaction, experiments were first conducted keeping the nickel catalyst surface area constant. The results of these experiments showed that the hydrogenation reaction can be explained by a first order mechanism. Changing the speed of the stirrer did not effect the rate of the reaction; hence it was inferred that the reaction was not external mass transfer controlled. It was also seen that there was an no significant difference in reaction rates between the stirred and sonicated systems. Hence we conclude that sonication does not effect any process involved in the actual process of hydrogenation, i.e., adsorption, desorption, surface reaction, etc., do not get effected.
It was concluded that the observed rate enhancements of similar compounds in the same system occur only when nickel catalyst is being continuously formed. This is possible only if irradiation with ultrasound enhances the rate of formation of the surface area of the nickel deposit. To study this phenomena, experiments were conducted with continuous formation of nickel catalyst. These experiments were conducted in three ways - stirring with zinc dust, sonication with zinc dust and stirring with presonicated zinc dust. For the first two kinds of experiments, the rates were low, increased to a maximum value and then decreased, but the nature of the third kind of experiments were different. The initial rates were very high as compared to either of the other two kinds of experiments but the rate rapidly reduces and becomes comparable to the rates obtained by stirring with zinc dust. We conclude that sonication creates many active sites on the surface of the zinc particles in the form of crystal defects, which are perhaps necessary for the deposition of nickel. When presonicated zinc particles are used, there are large numbers of these sites and these get consumed rapidly when stirred with aqueous nickel chloride solution. In this work, we do not deal with this case.
In the case of sonication with zinc dust, these active sites are continuously created and are consumed by nickel deposition. For the stirred system, these sites are quite small to start with and new ones are not generated since there is no irradiation by ultrasound. Hence, the rates in the latter case are low for both nickel deposition and the hydrogenation reaction.
In the model, it was assumed that the rate of increase of surface area of nickel, characterized by a specific rate term k z, was proportional to the amount of nickel in the bulk and also to the amount of free zinc surface area available. Similarly, nickel which deposits on previously deposited nickel (characterized by another specific rate constant, kn) was proportional to the amount of nickel in the bulk, the nickel area already deposited and also the free zinc surface area available.
The model is in excellent agreement with the experimental data obtained. The model predicted higher values of kn and kz for the sonicated system, indicating that the rate of deposition of nickel is much higher in this case than for the stirred system. Moreover, the model also predicts that the deposit in the case of a sonicated system is thinner and flatter, since it was seen that the surface area created for the same amount of nickel deposited was much higher in this case than the stirred system.
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McLean, William Neil. "Metal catalysed reactions in organic chemistry." Thesis, University of Liverpool, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.257123.
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Ren, Chenhao. "Investigating Catalytic Selectivity of Nanoparticles encapsulated in MOFs:." Thesis, Boston College, 2021. http://hdl.handle.net/2345/bc-ir:109074.
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Thesis advisor: Chia-kuang TsungThesis advisor: Dunwei Wang
Coating porous materials is a potential pathway to improve Catalytic performance of heterogeneous catalysts. The unique properties of Metal organic frameworks (MOFs) like huge surface area, long range order and high tenability make them promising coating materials. However, two traditional MOF encapsulation methods have their own issues. Herein, we synthesized Pt/Pd metal nanoparticles @UiO-66-NH2 via a one-pot in situ method which has good control of nanoparticles size while avoids the introduction of capping agent. The catalytic performance of synthesized Pt@UiO-66-NH2 is tested via selective hydrogenation of Crotonaldehyde. And the selectivity of our desired product achieves 70.42% which is much higher than merchant Pt catalysts. A step further, we used linker exchange to replace the original NH2-BDC linker of which amine group plays an important role in the coating process. After linker exchanging, the significant decreasing in selectivity of our target product demonstrates that the interaction between Pt and amine group does have some positive impacts on their catalytic performance. We hope our research could provide some insights of the MOFs and nanoparticles interface and help rational design of catalysts with high performance
Thesis (MS) — Boston College, 2021
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Nieuwoudt, Josias Jakobus. "Mathematical Modelling of Catalytic Distillation in a 1-Hexene Hydrogenation System." Doctoral thesis, University of Cape Town, 2010. http://hdl.handle.net/11427/5425.
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Silva, Fortes Antonio Belmiro Gil da. "Synthesis and applications of chiral phosphine ligands to catalytic asymmetric hydrogenation." Thesis, University of Liverpool, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.359177.
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Sun, Xiuyan. "Studies of catalytic asymmetric transfer hydrogenation in batch and continuous reactors." Thesis, University College London (University of London), 2008. http://discovery.ucl.ac.uk/1446201/.
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The aim of this work was to design novel reactors to increase the reaction conversion and enantioselectivity for the asymmetric transfer hydrogenation (ATH) of acetophenone. The reactor designs should also be amenable to scale-out for increase of productivity. Asymmetric transfer hydrogenation of acetophenone with isopropanol is a reversible reaction and backwards reaction limits the reaction conversion and enantioslectivity. Novel reactor design aims to efficient acetone removal, which is a byproduct in the reaction system. By gas stripping, reaction equilibrium can be shifted and hence conversion and enantioselectivity improved. Reaction conditions optimization was initially conducted in a laboratory batch reactor and a simple kinetic model was built. The catalyst deactivation, the effect of the temperature, substrate concentration, substrate/catalyst concentration ratio and acetone concentration on the ATH were investigated. The metal-ligand bifunctional mechanism was considered for the kinetic model. The gPROMS/gEST commercial software was used for kinetic parameters estimation. Three continuous reactors (tubular reactor, rotating disc reactor and micromesh reactor) were designed and fabricated, each one encompassing a different gas/liquid contacting method. In the tubular reactor, gas/liquid contact is achieved through slugs. In the rotating disc reactor, gas/liquid contact is achieved through a thin film formed on the disc which rotates. In the micromesh reactor, a micromesh forms and stabilizes the gas/liquid interface. Acetone removal and asymmetric transfer hydrogenation studies were carried out under different conditions in these reactors and the performance of the different reactors were compared. The tubular reactor showed similar performance as the batch reactor. The rotating disc reactor enhanced acetone removal, thus improved the conversion and enantioselectivity. Acetone was removed most efficiently in the micromesh reactor. Therefore, the highest conversion and enantioslectivity were also obtained in this reactor. By simplified calculations, it was established that in order to increase the acetone removal efficiency, the ratio of gas to liquid flowrate and the gas-liquid interfacial area has to be increased. The scale out/up concept was also demonstrated with the micromesh reactor. Scale out/up was achieved by increasing the number of meshes in parallel and enlarging the single mesh reactor. The conversion and enantioselectivity was slightly lower in the scaled out version reactor which is probably due to the fact that the flow distribution inside the reactor was not uniform.
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Johansson, Johannes. "Inhibition Kinetics of Hydrogenation of Phenanthrene." Thesis, KTH, Skolan för kemi, bioteknologi och hälsa (CBH), 2019. http://urn.kb.se/resolve?urn=urn:nbn:se:kth:diva-279025.
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In this thesis work the hydrogenation kinetics of phenanthrene inhibited by the basic nitrogen compound acridine and the non-basic carbazole was investigated. Based on a transient reactor model a steady state plug flow model was developed and kinetic parameters were estimated through nonlinear regression to experimental data. The experimental data was previously collected from hydrotreating of phenanthrene in a bench-scale reactor packed with a commercial NiMo catalyst mixed with SiC. As a first two-step solution, the yields of the hydrogenation products of phenanthrene were predicted as a function of conversion, which subsequently was used to calculate concentration profiles as a function of position in reactor. As a second improved solution, the concentration profiles were calculated directly as a function of residence time, and these results were then used for further analysis. Reaction network 2 in figure 7 was considered sufficient to describe the product distribution of phenanthrene, with a pseudo-first-order rate law for the nitrogen compounds. Both solution methods provided similar results which gave good predictions of the experimental data, with a few exceptions. These cases could be improved by gathering more experimental data or by investigating the effect of some model assumptions. The two-step method thus proved useful in evaluating the phenanthrene reaction network and providing an initial estimate of the parameters, while the onestep method then could give a more precise solution by calculating all parameters simultaneously. As expected, acridine was shown to be more inhibiting than carbazole, both in the produced concentration profiles and estimated parameters. A possible saturation effect was also seen in the inhibition behavior, where adding more nitrogen compounds only had a small additional effect on the phenanthrene conversion. The Mears and Weisz-Prater criteria were found to be inversely proportional to the concentrations of the nitrogen compounds and otherwise only depend on rate constants, with values well below limits for diffusion controlled processes. Sensitivity analyses also supported that the global minimum had been found in the nonlinear regression solution.
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Carter, Charles Ross. "The novel synthesis of aldehyde insect sex pheromones." Thesis, Bangor University, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.341179.
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L'Hospital, Valentin. "Développement et optimisation de catalyseurs à base de cuivre pour la synthèse de méthanol et de diméthyléther à partir de CO2." Thesis, Strasbourg, 2018. http://www.theses.fr/2018STRAF028/document.
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Diminuer les émissions de CO2, principal gaz à effet de serre, constitue un des enjeux majeurs de notre ère actuelle. De nombreuses mesures existent déjà mais sont encore insuffisantes. C’est dans ce cadre que le projet ANR DIGAS a vu le jour. Durant ces travaux, des matériaux catalytiques composés de CuO/ZnO/ZrO2 ont été développés par coprécipitation classique et ont été testés sous une pression de 50 bar pour la synthèse de méthanol à partir de l’hydrogénation de CO2. Ces catalyseurs ont ensuite été optimisés à l’aide d’un système développé au laboratoire : la synthèse microfluidique en continu. Elle a permis de rendre les catalyseurs plus homogènes et ainsi plus efficaces. Le catalyseur le plus performant a, par la suite, été couplé à un catalyseur acide, une zéolithe ZSM5, pour permettre la synthèse directe de diméthyléther (DME) à partir de l’hydrogénation de CO2. Dans le cas de la synthèse de méthanol ainsi que pour la synthèse de DME, les catalyseurs développés sont compétitifs et plus performants que les catalyseurs actuellement sur le marchéReducing CO2 emissions, the main greenhouse gas, is one of the major challenges of our current era. Many measures already exist but are still insufficient. It is in this context that the ANR project called DIGAS was funded. During this work, catalytic materials composed of CuO/ZnO/ZrO2 were developed by classical coprecipitation and tested under a pressure of 50 bar for the methanol synthesis from CO2 hydrogenation. Then, these catalysts were optimized using a system developed in the laboratory: microfluidic continuous synthesis. It has made the catalysts more homogeneous and thus more efficient. The most efficient catalyst was subsequently coupled to a ZSM5 zeolite to allow direct dimethyl ether (DME) synthesis from the CO2 hydrogenation. In the case of methanol as well as for DME synthesis, the developed catalysts are competitive and more efficient than the catalysts currently on the market
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Elkhaseh, Salem Farag. "Fundamental studies of enantioselective catalytic hydrogenation of ethyl pyruvate at supported platinum." Thesis, Cardiff University, 2008. http://orca.cf.ac.uk/54794/.
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Goda, Amit. "Correlating electronic and catalytic properties of bimetallic surfaces for model hydrogenation reactions." Access to citation, abstract and download form provided by ProQuest Information and Learning Company; downloadable PDF file, 184 p, 2009. http://proquest.umi.com/pqdweb?did=1654493511&sid=3&Fmt=2&clientId=8331&RQT=309&VName=PQD.
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Kasick, Andrew G. "The Effect of Ethanol upon the Catalytic Hydrogenation of Lactose to Lactitol." Ohio University / OhioLINK, 2019. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1575464470510949.
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Corral, Pérez Juan José. "Continuous hydrogenation of carbon dioxide to formates and formic acid over heterogeneous catalysts." Doctoral thesis, Universitat Rovira i Virgili, 2019. http://hdl.handle.net/10803/667680.
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La síntesi de format i àcid fòrmic via la hidrogenació de diòxid de carboni ofereix un camí prometedor en la valorització de diòxid de carboni, i una alternativa atractiva als processos comercials actuals. No obstant, aquesta reacció no és termodinàmicament favorable en fase gas. Per això, l’ús d’additius bàsics juntament amb catalitzadors homogenis en processos per lots representa l’estat de l’art en aquest camp. L’escassa investigació d’aquesta reacció fent ús de catalitzadors heterogenis ha pogut dificultar el seu posterior desenvolupament a escala industrial. En aquest treball, es demostra la síntesi contínua de format a partir de CO2 i H2 utilitzant catalitzadors heterogenis i amb l’avantatge de treballar a alta pressió. D’una banda, en la presència de metanol, el producte de la reacció és metanoat de metil, que és un potencial intermedi en la síntesi contínua d’àcid fòrmic mitjançant la hidròlisi. S’aporten nous enfocs en relació amb la reactivitat dels metalls d’encunyació, els rols dels òxids metàl·lics com suports, i els intermediaris reactius, així com els mecanismes de reacció. D’altra banda, la incorporació d’aigua o trietilamina a la corrent d’alimentació sobre un catalitzador molecular heterogenitzats promou la formació d’àcid fòrmic. A més, s’explora el potencial d’utilitzar un material porós per a immobilitzar un complex molecular d’iridi. Aquesta tesi destaca la importància de fer ús de distintes metodologies conjuntament per a verificar la localització i naturalesa dels llocs actius del catalitzador, i facilita així el seu disseny racional.La síntesis de formiato y ácido fórmico vía la hidrogenación de dióxido de carbono ofrece un camino prometedor en la valorización de dióxido de carbono, y una alternativa atractiva a los procesos comerciales. No obstante, esta reacción no es termodinámicamente favorable en fase gas. Por ello, el uso de aditivos básicos junto catalizadores homogéneos en procesos por lotes representa el estado del arte en este campo. La escasa investigación de esta reacción empleando catalizadores heterogéneos ha podido dificultar su posterior desarrollo a escala industrial. En este trabajo, se demuestra la síntesis continua de formiato a partir de CO2 e H2 utilizando catalizadores heterogéneos y con la ventaja de trabajar a alta presión. Por un lado, en la presencia de metanol, el producto de la reacción es metanoato de metilo, que es un potencial intermedio en la síntesis continua de ácido fórmico mediante la hidrólisis. Se aportan nuevos enfoques en relación con la reactivad de los metales de acuñación, los roles de los óxidos metálicos como soportes, y los intermediarios reactivos, así como los mecanismos de reacción. Por otro lado, la incorporación de agua o trietilamina en la corriente de alimentación sobre un catalizador molecular heterogeneizado promueve la formación de ácido fórmico. Además, se explora el potencial de utilizar un material poroso para inmovilizar un complejo molecular de iridio. Esta tesis destaca la importancia de emplear distintas metodologías conjuntamente para verificar la localización y naturaleza de los sitios activos del catalizador, facilitando así su diseño racional.
The synthesis of formates and formic acid by hydrogenation of carbon dioxide offers a promising path to valorise carbon dioxide and an appealing alternative to the commercial processes. However, such reaction is not thermodynamically favourable in gas phase. Thus, the use of basic additives together with homogeneous catalysts under batch conditions represent the state-of-the-art in this field. The scarce research on this reaction over heterogeneous catalysts may have hindered its further development at industrial scale. In this work, the continuous synthesis of formates from CO2 and H2 is demonstrated over heterogeneous catalysts, while taking advantage of high-pressure conditions. On one hand, in the presence of methanol, the reaction product is methyl formate, which can be a potential intermediate in the continuous synthesis of formic acid through its hydrolysis. New insights are provided regarding the reactivity of coinage metals, the roles of metal oxides as supports, and the reactive intermediates and reaction mechanisms. On the other hand, the cofeeding of water or triethylamine over a heterogenized molecular catalyst promotes the formation of formic acid. The potential of using a covalent triazine framework to immobilize an iridium molecular complex, as well as of the unique properties of the resulting material in CO2 hydrogenation reactions is explored. This thesis highlights the importance of employing combined methodologies to verify the location and nature of active sites, which can facilitate rational catalyst design by tuning active metal and support materials.
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Alvaro, Vasco Filipe Domingues. "Selective catalytic activity of metals supported on metal(IV) phosphates for heterogeneous reduction." Thesis, University of Liverpool, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.263780.
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Theodoulou, Louise. "Supported platinum and iridium catalysts for the selective hydrogenation of cinnamaldehyde." Thesis, University of Reading, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.343323.
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Azhari, C. H. "Characterisation and activity of polymer supported platinum and gold in catalytic hydrogenation reactions." Thesis, Brunel University, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.351570.
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Capezzuoli, Fabio. "Carbon dioxide adsorption on porous materials and its catalytic hydrogenation in supercritical phase." Thesis, Imperial College London, 2007. http://hdl.handle.net/10044/1/11969.
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Irvine, Stephanie. "Highly active iridium (I)complexes for catalytic hydrogen isotope exchange and selective hydrogenation." Thesis, University of Strathclyde, 2009. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.510835.
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Colley, Stephen William. "Synthesis of ethyl ethanoate from ethanol by heterogeneous catalytic dehydrogenation, hydrogenation and purification." Thesis, Durham University, 2002. http://etheses.dur.ac.uk/4159/.
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A study has been carried out into the reactions of ethanol over transition metal dehydrogenation catalysts, with particular emphasis on the reaction of ethanol to ethyl ethanoate. The reaction is of commercial interest, and the test work has been aimed at the development of a process that would yield ethyl ethanoate at commercially acceptable purity. Copper based catalysts have been shown to selectively promote the formation of ethyl ethanoate. Experimental work has been carried out to identify an optimised catalyst and reaction conditions for the ethanol to ethyl ethanoate reaction. A copper based catalyst that yields >95% selectivity to ethyl ethanoate, at >40% conversion of ethanol, has been identified. A purification scheme has been devised that incorporates selective hydrogenation using either nickel or ruthenium heterogeneous catalysts to remove aldehyde and ketone by-products. The purification scheme includes a novel distillation section. The catalyst system developed can be used to synthesise ethyl ethanoate at a purity of >99.98% from industrially available ethanol that contains up to 5% 2-propanol. A commercial plant producing 50,000 tonnes of ethyl ethanoate per annum, using the technology described in this thesis, has been in operation since April 2001.Four patents, based on the technology described in this thesis, have been applied for or granted.
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Dharmasena, Ureshini Lasantha. "N-heterocyclic carbenes as activating ligands in hydrogenation catalysts: Synthetic and catalytic studies." Thesis, University of Ottawa (Canada), 2005. http://hdl.handle.net/10393/26888.
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Novel hydridochlorocarbonyl ruthenium complexes containing N-heterocyclic carbene (NHC) ligands were prepared in order to explore the effect of the NHC ligand class in hydrogenation chemistry. Routes were developed to RuHCl(CO)(NHC)(PPh 3) (NHC = IMes, H2IMes) from RuHCl(CO)(PPh3) 3, and the hydrogenation activities of these complexes were screened against that of the known complexes RuHCl(CO)(PCy3)2 and RuHCl(CO)(IMes)(PCy3). The combination of the donor ability of the NHC ligand, in conjunction with the lability of the PPh3 group, increased activity for the challenging hydrogenation of sterically hindered trans internal olefins, but also led to competing isomerization of terminal olefins and polymerization of strained cycloolefins.
In the course of this work, high yield, efficient new routes were also developed to the known complexes RuHCl(CO)(PCy3)2 and RuHCl(CO)(NHC)(PCy3) from RuHCl(CO)(PPh3)3. The lability of the phosphine groups in the latter precursor complex enabled milder reaction conditions than had been possible in the literature methods.
In an effort to gain access to carbonyl-free analogues, synthesis of a ruthenium hydride complex containing a cyclometalated IMes ligand was undertaken. However, the product obtained using the reported method was a novel complex, formulated as RuHCl(IMes)2 on the basis of extensive NMR and MALDI-MS analysis.
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Kobl, Kilian. "Aspects mécanistiques et cinétiques de la production catalytique de méthanol à partir de CO2/H2." Thesis, Strasbourg, 2015. http://www.theses.fr/2015STRAF023/document.
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En vue du changement climatique et de la transition énergétique, le présent travail s’intègre dans le projet ANR VItESSE2 portant sur le stockage d’énergie électrique renouvelable et la valorisation du CO2 par hydrogénation en méthanol sur des catalyseurs au cuivre. Au cours de cette thèse, une méthode analytique pour la mesure des surfaces de cuivre par chimisorption de N2O a été mise au point. À partir de tests catalytiques sous 50 bar, des modèles cinétiques pour des catalyseurs Cu/ZnO/Al2O3 et Cu/ZnO/ZrO2 ont été élaborés. Pour l’étude mécanistique, un montage infrarouge en réflexion diffuse a été développé afin d’étudier différents catalyseurs pour la synthèse de méthanol et pour la réaction du gaz à l’eau. Le montage a servi pour des tests catalytiques in situ à 34 bar sous flux réactionnel. L’étude a été complétée par des expériences de désorption thermoprogrammée de différentes molécules sonde. Les résultats suggèrent que le catalyseur Cu/ZnO/ZrO2 est plus sélectif pour le méthanol que Cu/ZnO/Al2O3 et qu’un mode de préparation favorisant les interactions Cu–ZnO–ZrO2 peut être bénéfique pour l’activité catalytiqueIn view of the climate change and the energy transition, this work is part of the ANR project VItESSE2 about renewable electric energy storage and CO2 valorization by methanol hydrogenation on copper catalysts. During this thesis, an analytical method for copper surface measurement by N2O chemisorption was developed. Based on catalytic tests at 50 bar, kinetic models for Cu/ZnO/Al2O3 and Cu/ZnO/ZrO2 catalysts were elaborated. For the study of the mechanism, a diffuse reflection infrared setup was developed in order to study different catalysts for methanol synthesis and water-gas shift reaction. The setup was used for in situ catalytic tests at 34 bar under reaction flow. The study was complemented by temperature programmed desorption experiments with different probe molecules. The results suggest that the Cu/ZnO/ZrO2 catalyst is more selective for methanol than Cu/ZnO/Al2O3 and that a preparation method which favors Cu–ZnO–ZrO2 interactions can be beneficial for catalytic activity
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Ellis, Ieuan. "Interstitial modification of palladium for partial hydrogenation reactions." Thesis, University of Oxford, 2016. https://ora.ox.ac.uk/objects/uuid:7c8c294c-0583-4a61-98e5-4c32d76cbf89.
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Heterogeneous catalysis is a key industrial process involved in the synthesis of nearly all chemicals currently produced. The environmental impact of these processes is huge so improvements must be made to current catalysts. Should a new material provide better yields at lower energy cost the benefits to both the industry and the planet are significant. There are many ways to change the behaviour of a catalyst, the addition of dopants, the selective blocking of active sites, and changing the strength of the support interaction to name a few. One technique that has become increasingly investigated is interstitial modification, the insertion of a light element into a metal lattice to change the metal's catalytic properties. The work presented in this thesis devises greener synthetic routes to the known Pd-interstitialB/C catalyst and investigates potential routes to a novel interstitial material, Pd-interstitialLi/C. Initially, successful verification of interstitial modification comes from the characteristic increase in palladium lattice parameter from 3.89 to 4.00 Å and the blocking of the β-hydride formation. Initial catalytic screening determines the synthetic route which yields the most active catalyst which subsequently undergoes thorough characterisation. The wealth of evidence generated confirms the interstitial location of lithium within the palladium lattice, as well as adding to the current understanding of the Pd-interstitialB/C material. EELS analysis on Pd-interstitialB is the closest to direct observation of boron within the palladium lattice to date. PDF on Pd-interstitialLi shows 13.7 % of the palladium octahedral interstitial sites are occupied by lithium. This is the first report of interstitial lithium within palladium to date. The effect of the interstitial modification on catalytic hydrogenation by two elements that have opposite effects on the surface electronics of the host palladium gives intriguing results. The effect on catalysis varies depending on the conditions investigated. This bank of hydrogenation data allows an informed choice as to which interstitial material would be best suited to the gas or liquid phase catalytic hydrogenation under investigation.
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Furst, Marc R. L. "Polymer precursors from catalytic reactions of natural oils." Thesis, University of St Andrews, 2013. http://hdl.handle.net/10023/3684.
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The bidentate ligand 1,2-bis(ditertbutylphosphinomethyl)benzene has been shown to be a very efficient catalyst for operating the alkoxycarbonylation of alkenes and unsaturated esters and carboxylic acids giving a very high selectivity to the linear product with very few exceptions to this general rule. Due to the increasing prices of petroleum feedstock and petroleum-derived chemicals, the preparation of chemicals starting from renewable resources and waste products from the industry becomes an interesting alternative. Fatty acids and fatty esters, due to the existence of one or more unsaturation in their alkyl chain are subjected to the alkoxycarbonylation reactions in presence of 1,2-bis(ditertbutylphosphinomethyl)benzene, palladium, methane sulfonic acid, carbon monoxide and methanol, yielding diesters with a long carbon chain (up to 19 carbon atoms). The diesters are shown to be readily prepared from unpurified olive, rapeseed or sunflower oils as well as from tall oil. In the last case triesters are also formed. The diesters are subjected to hydrogenation in the presence of 1,1,1-tris(diphenylphosphinomethyl)ethane, ruthenium and hydrogen, in a mixture of dioxane and water at high temperature, yielding the corresponding diols. The resulting products of the reactions are monomers for preparing polyesters having the potential to replace some existing petroleum-based polymers (for instance polyethylene). The aminocarboxylation reaction in the presence of the same palladium/1,2-bis(ditertbutylphosphinomethyl) benzene catalyst, in the presence of aniline, 2{naphthol and potassium iodide in diethylether, is employed for preparing esteramides, which are subjected to hydrogenation. Aromatic polyamides are prepared by melting together an aromatic diamine and diacids obtained from methoxycarbonylation. Finally, N-Heterocyclic Carbene (NHC) ligands are employed for preparing new palladium complexes which are used in the Suzuki-Miyaura cross-coupling reaction in a water/isopropanol mixture. Other complexes based on copper are employed for developing an inexpensive transmetallation reaction for transferring a NHC ligand from copper to palladium and gold.