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Relevant bibliographies by topics / Wilkinson’s Catalyst

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Academic literature on the topic 'Wilkinson’s Catalyst'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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Journal articles on the topic "Wilkinson’s Catalyst"

1

Albayer, Mohammad, and Jason L. Dutton. "Reactions of Trivalent Iodine Reagents with Classic Iridium and Rhodium Complexes." Australian Journal of Chemistry 70, no. 11 (2017): 1180. http://dx.doi.org/10.1071/ch17173.

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In this work, the reactions of iodine(iii) reagents (PhI(L)2: L = pyridine, acetate (OAc−), triflate (OTf−)) with iridium(i) and rhodium(i) complexes (Vaskas’s compound, Wilkinson’s catalyst, and bis[bis(diphenylphosphino)ethane]rhodium(i) triflate) are reported. In all cases, the reactions resulted in two-electron oxidation of the metal complexes. Mixtures of products were observed in the reactions of Iiii reagents with Vaska’s compound and Wilkinson’s catalyst via ligand exchange and anion scrambling. In the case of reacting Iiii reagents with chelating ligand-containing bis[bis(diphenylphosphino)ethane]rhodium(i) triflate, no scrambling was observed.

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Osei Akoto, Clement, and Jon D. Rainier. "Concise Seven-Membered Oxepene/Oxepane Synthesis – Structural Motifs in Natural and Synthetic Products." Synthesis 51, no. 18 (May 20, 2019): 3529–35. http://dx.doi.org/10.1055/s-0037-1611838.

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This work outlines a suitable method for the synthesis of oxepane skeleton using iterative C-glycoside technology on the oxepene intermediate, which was synthesized utilizing Wilkinson’s catalyst [Rh(PPh3)3Cl] to generate the isomerized product in a linear synthetic manner. The central core of the oxepene motif was achieved via an olefin metathesis reaction using the Grubbs second-generation and Schrock catalysts. The synthesis of the functionalized oxepane having the desired adriatoxin E-ring relative stereochemistry was achieved starting from commercially available homopropargylic alcohol.

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Kyselka, J., L. Thomes, S. Remišová, M. Dragoun, M. Berčíková, and V. Filip. "Preparation of conjugated linoleic acid enriched derivatives by conventional and biphasic isomerisation." Czech Journal of Food Sciences 34, No. 6 (December 21, 2016): 511–21. http://dx.doi.org/10.17221/362/2016-cjfs.

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The preparation of conjugated linoleic acid (CLA)-enriched free fatty acids by industrial processes compared with our biphasic isomerisation experiments in a special designed reactor enabling the preparation of CLA esters was evaluated. Our experiments further revealed the main disadvantage of semi-synthetic alkali isomerisation to be the formation of conjugated E,E-octadecadienoic acid isomers (2.92–3.44%) and the bioavailability of free fatty acid products. Urea fractionation technology improved the quality of the reaction mixture, but at the same time the yield of rumenic acid was decreased on purification. Therefore, we decided to apply complexes of noble metals in order to isomerise linoleic acid ester derivatives. The known Wilkinson’s hydrogenation catalyst, RhCl (PPh<sub>3</sub>)<sub>3</sub>, was found to be the most effective. We investigated the preparation of bioavailable CLA-enriched triacylglycerols. Special attention was paid to recycling of Wilkinson’s catalyst.

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Patel, Pranav, Chih-Tsung Chang, Namin Kang, Gue-Jae Lee, William S. Powell, and Joshua Rokach. "Reductive deprotection of silyl groups with Wilkinson’s catalyst/catechol borane." Tetrahedron Letters 48, no. 30 (July 2007): 5289–92. http://dx.doi.org/10.1016/j.tetlet.2007.05.118.

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Bezuidenhoudt, Barend, Johannes van Tonder, Charlene Marais, and David Cole-Hamilton. "Regioselective Hydrogenation of α,β-Unsaturated Ketones over Wilkinson’s Catalyst." Synthesis 2010, no. 03 (November 13, 2009): 421–24. http://dx.doi.org/10.1055/s-0029-1217117.

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Yang, Zhenyu, Maike H. Wahl, and Jonathan G. C. Veinot. "Size-independent organosilane functionalization of silicon nanocrystals using Wilkinson’s catalyst." Canadian Journal of Chemistry 92, no. 10 (October 2014): 951–57. http://dx.doi.org/10.1139/cjc-2014-0048.

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A low-temperature size-independent method for modifying the surface chemistry of the silicon nanocrystal (SiNC) surface is reported. Wilkinson’s catalyst has been applied to accelerate the dehydrogenative coupling reaction between organosilane molecules and hydride-terminated SiNCs. Two strategies and multiple organosilanes were evaluated to study surface modification efficiency. During the investigations, it was determined that surface functionalization efficiency showed some dependence upon the organic modifier in question. The comparatively low reactivity of octadecyldimethyl silanes may result from the formation of “Si–Rh–Si” intermediates hindered by the steric bulk of the silanes when reacted with activated SiNCs. Quenching of the SiNC-based photoluminescence is observed and the origin of this phenomenon has been attributed to the present of trace rhodium on SiNCs detected using X-ray photoelectron spectroscopy.

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Leitmannová, Eliška, Petr Jirásek, Jakub Rak, Lucie Potucká, Petr Kačer, and Libor Červený. "Terminal C≡C triple bond hydrogenation using immobilized Wilkinson’s catalyst." Research on Chemical Intermediates 36, no. 5 (September 2010): 511–22. http://dx.doi.org/10.1007/s11164-010-0162-1.

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Yang, Lijuan, Hui Wang, Garry L. Rempel, and Qinmin Pan. "Recovery of Wilkinson’s Catalyst from Hydrogenated Nitrile Butadiene Rubber Latex Nanoparticles." Topics in Catalysis 57, no. 17-20 (September 5, 2014): 1558–63. http://dx.doi.org/10.1007/s11244-014-0333-1.

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Kramer, Jurjen, Erica Nöllen, Wim Buijs, Willem L. Driessen, and Jan Reedijk. "Investigations into the recovery of Wilkinson’s catalyst with silica-immobilised P-donor ligands." Reactive and Functional Polymers 57, no. 1 (November 2003): 1–11. http://dx.doi.org/10.1016/j.reactfunctpolym.2003.06.001.

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Grünberg, Anna, Xu Yeping, Hergen Breitzke, and Gerd Buntkowsky. "Solid-State NMR Characterization of Wilkinson’s Catalyst Immobilized in Mesoporous SBA-3 Silica." Chemistry - A European Journal 16, no. 23 (May 5, 2010): 6993–98. http://dx.doi.org/10.1002/chem.200903322.

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Dissertations / Theses on the topic "Wilkinson’s Catalyst"

1

Gillman, Kevin W. "Hydroboration of strained cyclopropane ring systems promoted by Wilkinson's catalyst /." Online version of thesis, 1991. http://hdl.handle.net/1850/10947.

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2

Feng, Pingyun. "Hydroboration-oxidation of styrene, 2,3-dihydrofuran and quadricyclene dimethylester promoted by Wilkinson's catalyst /." Online version of thesis, 1991. http://hdl.handle.net/1850/10959.

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3

Li, Ting. "Catalytic Hydrogenation of Nitrile Rubber in High Concentration Solution." Thesis, 2011. http://hdl.handle.net/10012/6120.

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Chemical modification is an important way to improve the properties of existing polymers, and one of the important examples is the hydrogenation of nitrile butadiene rubber (NBR) in organic solvent by homogeneous catalysis in order to extend its application. This process has been industrialized for many years to provide high performance elastomers (HNBR) for the automotive industry, especially those used to produce components in engine compartments. In the current commercial process, a batch reactor is employed for the hydrogenation step, which is labor intensive and not suitable for large volume of production. Thus, novel hydrogenation devices such as a continuous process are being developed in our research group to overcome these drawbacks. In order to make the process more practical for industrial application, high concentration polymer solutions should be targeted for the continuous hydrogenation. However, many problems are encountered due to the viscosity of the high concentration polymer solution, which increases tremendously as the reaction goes on, resulting in severe mass transfer and heat transfer problems. So, hydrogenation kinetics in high concentration NBR solution, as well as the rheological properties of this viscous solution are very essential and fundamental for the design of novel hydrogenation processes and reactor scale up. In the present work, hydrogenation of NBR in high concentration solution was carried out in a batch reactor. A commercial rhodium catalyst, Wilkinson’s catalyst, was used with triphenylphosphine as the co-catalyst and chlorobenzene as the solvent. The reactor was modified and a PID controller was tuned to fit this strong exothermic reaction. It was observed that when NBR solution is in a high concentration the kinetic behavior was greatly affected by mass transfer processes, especially the gas-liquid mass transfer. Reactor internals were designed and various agitators were investigated to improve the mechanical mixing. Experimental results show that the turbine-anchor combined agitator could provide superior mixing for this viscous reaction system. The kinetic behavior of NBR hydrogenation under low catalyst concentration was also studied. It was observed that the hydrogenation degree of the polymer could not reach 95% if less than 0.1%wt catalyst (based on polymer mass) was used, deviating from the behavior under a normal catalyst concentration. The viscosity of the NBR-MCB solutions was measured in a rotational rheometer that has a cylinder sensor under both room conditions and reaction conditions. Parameters that might affect the viscosity of the solutions were studied, especially the hydrogenation degree of polymer. Rheological properties of NBR-MEK solutions, as well as NBR melts were also studied for relevant information. It is concluded that the hydrogenation kinetics deviates from that reported by Parent et al. [6] when polymer is in high concentration and/or catalyst is in low concentration; and that the reaction solution (HNBR/NBR-MCB solution) deviates from Newtonian behavior when polymer concentration and hydrogenation degree are high.

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Naicker, Serina. "An investigation into air stable analogues of Wilkinson's catalyst." Thesis, 2010. http://hdl.handle.net/10413/10765.

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Since the discovery of Wilkinson’s catalyst and its usefulness in the homogeneous hydrogenation of olefins many investigations have been carried out on trivalent, tertiary phosphine–rhodium complexes.¹ Studies have shown that N-Heterocyclic carbenes as ligands offer increased stability to the complex and possess similar electronic properties as phosphine ligands.² The applications of the traditional catalyst are limited due to the limited stability of its solutions and its susceptibility to attack from the environment i.e. oxygen and moisture. The hydrogenation of olefins and other unsaturated compound is of great importance for the fine chemical and petroleum industries. The aim is to produce more stable and active versions of the traditional catalyst and also to demonstrate their improved stability and activity in catalytic applications. This study involves the investigation of the effects of ligand modification on Wilkinson type hydrogenation catalysts. Five Rhodium-phosphine complexes 1a: Rh(PPh₃)₃Cl, 1b: Rh(PPh₂Me)₃Cl, 1c: Rh(PPh₂Et)₃Cl, 1d: Rh(PPhMe₂)₃Cl, 1e: Rh(PPhMe₂)₃Cl have been synthesised and characterised by means of melting point,¹H NMR, ¹³C NMR, ³¹P NMR, IR and Mass Spectroscopy. Complexes 1d and 1e have also been characterised by means of elemental analysis and single crystal XRD. Five rhodium-N-heterocyclic carbene complexes 2a: Rh(COD)ImesCl [Imes =1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] , 2b: Rh(COD)(diisopropylphenyl)₂Cl 2c: Rh(COD)(adamantyl)²Cl, 2d: Rh(COD)(diisopropyl)²Cl 2e: Rh(COD)(ditertbutyl)²Cl have been synthesised and characterised by means of melting point, ¹H NMR, ¹³C NMR, IR and Mass Spectroscopy. Five rhodium-NHC-CO complexes 3a: Rh(CO)₂ImesCl, 3b: Rh(CO)₂(diisopropylphenyl)₂Cl, 3c: Rh(CO)₂(adamantyl)₂Cl , 3d: Rh(CO)₂(diisopropyl)₂Cl, 3e: Rh(CO)₂(ditertbutyl)₂Cl, have been synthesised and characterised by means of ¹H NMR, ¹³C NMR, IR and Mass Spectroscopy. Complexes 1a, 1d, 1e, 2a, 2b, 2c, 2d, 2e were tested in the hydrogenation of simple alkenes under mild conditions. For the rhodium-phosphine complexes the catalyst efficiency based on TOF increases in the following order: 1a > 1d > 1e or RhCl₃(PPhMe₂)₃ > RhCl₃(PPhEt₂)₃ > RhCl(PPh₃)₃. For the rhodium-(COD)-NHC complexes catalyst efficiency based on TOF increases in the following order: 2d > 2b > 2e > 2a > 2c. While rhodium-phosphine complexes are far more active than rhodium-(COD)-NHC complexes, the latter seem to be active for a longer time and hence more stable under mild hydrogenation conditions.
Thesis (M.Sc.)-University of KwaZulu-Natal, Durban, 2010.

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5

石如悅. "The studies of decarbonylation of acid halides with Wilkinson's catalyst." Thesis, 1987. http://ndltd.ncl.edu.tw/handle/60269659427178749894.

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6

Schumacher, C., Deborah E. Crawford, B. Raguž, R. Glaum, S. L. James, C. Bolm, and J. G. Hernández. "Mechanochemical dehydrocoupling of dimethylamine borane and hydrogenation reactions using Wilkinson's catalyst." 2018. http://hdl.handle.net/10454/17697.

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No
Mechanochemistry enabled the selective synthesis of the recherche´ orange polymorph of Wilkinson’s catalyst [RhCl(PPh3)3]. The mechanochemically prepared Rh-complex catalysed the solvent-free dehydrogenation of Me2NHBH3 in a ball mill. The in situ-generated hydrogen (H2) could be utilised for Rh-catalysed hydrogenation reactions by ball milling.
We thank the RWTH Aachen University for support from the Distinguished Professorship Program funded by the Excellence Initiative of the German federal and state governments, and the EPSRC for funding (EP/L019655/1).

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7

Wei, Zhenli. "Direct Catalytic Hydrogenation of Unsaturated Diene-Based Polymers in Latex Form." Thesis, 2006. http://hdl.handle.net/10012/2682.

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The direct catalytic hydrogenation of nitrile butadiene rubber (NBR) in latex form was studied as a model system for the development of a new latex hydrogenation process for the modification of unsaturated diene-based polymers. NBR is a synthetic rubber of copolymerized acrylonitrile and butadiene produced in latex form by emulsion polymerization. The catalytic hydrogenation of NBR is an important post-polymerization process resulting in a more stable and tougher derivative, hydrogenated NBR (HNBR), which has been widely used in the automotive and oil drilling industry. The present commercial process involves a number of cumbersome steps to obtain solid NBR from the latex and subsequent dissolution of the solid NBR in a large amount of organic solvent followed by solvent recovery after coagulation of the hydrogenated NBR. Since NBR is produced in latex form, it is very desirable to directly hydrogenate NBR in the latex form which will significantly simplify the hydrogenation process and facilitate subsequent applications. As an economical and environmentally benign alternative to the commercial processes based on the hydrogenation of NBR in organic solution, this direct latex hydrogenation process is of special interest to industry. The objective of this project is to develop an efficient catalytic system in order to realize the direct catalytic hydrogenation of NBR in latex form. OsHCl(CO)(O2)(PCy3)2 was initially used as the catalyst to investigate the possibility of hydrogenation of NBR in latex form and to understand the major factors which affect the hydrogenation operation. It was found that an organic solvent which is capable of dissolving or swelling the NBR was needed in a very small amount for the latex hydrogenation using the Os catalyst, and gel occurred in such a catalytic system during hydrogenation. Wilkinson’s catalyst, RhCl(PPh3)3, was then used for the latex hydrogenation in the presence of a small amount of solvent successfully without gel formation. Further investigation found that Wilkinson’s catalyst has a high activity for NBR latex hydrogenation without the use of any organic solvent. The influences of various operation conditions on hydrogenation rate, such as catalyst and polymer concentrations, latex system composition, agitation, reaction temperature and hydrogen pressure, have been investigated. It was found that the addition of triphenylphosphine (TPP) has a critical effect for the hydrogenation of NBR latex, and the hydrogenation rate was mainly controlled by the amount of catalyst which diffused into the polymer particles. In the presence of TPP, NBR latex can be hydrogenated to more than 95% degree of hydrogenation after about 30 hours at 160oC using Wilkinson’s catalyst with a catalyst to NBR rubber ratio of 1 wt%, without the addition of any organic solvent. The apparent activation energy for such NBR latex hydrogenation over the temperature range of 152oC to 170oC was found to be 57.0 kJ/mol. In the present study, it was also found that there are some impurities within the NBR latex which are detrimental to the hydrogenation reaction and are suspected to be water-soluble surfactant molecules. Deliberately designed solution hydrogenation experiments were conducted to study the impurity issue, and proper latex treatment methods have been found to purify the latex before hydrogenation. To improve the hydrogenation rate and to optimize the latex hydrogenation system, water soluble RhCl(TPPMS)3 catalyst (TPPMS: monosulphonated-triphenylphosphine) was used for the latex hydrogenation of NBR. The latex hydrogenation using the water soluble catalyst with TPP can achieve more than 90% degree of hydrogenation within 20 hours at 160oC. Further experiments using RhCl3 with TPP proved that the water soluble RhCl3 can be directly used as a catalyst precursor to generate the catalytic species in situ for the latex hydrogenation, and a stable NBR latex with 96% degree of hydrogenation can be produced without any gel problem within 19 hours of reaction at 160oC. The catalyst mass transport processes for these Rh based catalysts in the latex system were investigated in order to further optimize the solvent-free latex hydrogenation process. While maintaining the emulsified state of the original latex, the direct catalytic hydrogenation of NBR latex can be carried out efficiently without any cross-linking problem to more than 92% degree of hydrogenation within 8 hours at 160oC. As a result of this research project, new latex hydrogenation technologies were successfully developed to fulfill all major requirements for a solvent-free polymer latex hydrogenation route, which is a significant milestone for the improvement of this polymer modification technology. The finding of TPP’s role as the “catalyst mass transfer promoter” is a breakthrough for the research field related to the hydrogenation of unsaturated diene-based polymers in latex form.

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Book chapters on the topic "Wilkinson’s Catalyst"

1

Osborn, J. A., G. Wilkinson, and J. J. Mrowca. "Chlorotris(Triphenylphosphine)Rhodium(I)(Wilkinson'S Catalyst)." In Inorganic Syntheses, 77–79. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470132593.ch17.

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2

Koga, Nobuaki, and Keiji Morokuma. "Potential Energy Surface of Olefin Hydrogenation by Wilkinson Catalyst." In ACS Symposium Series, 77–91. Washington, DC: American Chemical Society, 1989. http://dx.doi.org/10.1021/bk-1989-0394.ch006.

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3

Hussain, M. Sakhawat, Shafique Ahmad Awan, M. A. Khan, and Haleem Hamid. "Pulsed Laser Polymerization of Methyl Methacrylate Using Wilkinson's Catalyst as a Photoinitiator." In ACS Symposium Series, 451–61. Washington, DC: American Chemical Society, 2003. http://dx.doi.org/10.1021/bk-2003-0847.ch038.

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4

"Anchored Wilkinson’s Catalyst." In Catalysis of Organic Reactions, 83–88. CRC Press, 2005. http://dx.doi.org/10.1201/9781420028034-16.

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Augustine, Robert, Gabriela Alvez, Norman Marin, and Setrak Tanielyan. "Anchored Wilkinson's Catalyst." In Catalysis of Organic Reactions, 175–83. CRC Press, 2008. http://dx.doi.org/10.1201/9781420070774.ch20.

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6

Doraiswamy, L. K. "Homogeneous Catalysis." In Organic Synthesis Engineering. Oxford University Press, 2001. http://dx.doi.org/10.1093/oso/9780195096897.003.0014.

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Catalysis by soluble complexes of transition metals is a rapidly gaining mode of catalysis in organic synthesis. These metals form bonds with one or more carbons in an organic reactant resulting in complexes that are known as organometallic complexes. Catalysis by these complexes is often referred to as homogeneous catalysis. Among the important applications of homogeneous catalysis in organic synthesis are isomerization of olefins; hydrogenation of olefins (carried out using Wilkinson type catalysts); oligomerization; hydroformylation of olefins to aldehydes with CO and H2 (the oxo process); carbonylation of unsaturated hydrocarbons and alcohols with CO (and coreactants such as water); oxidation of olefins to aldehydes, ketones, and alkenyl esters (Wacker process); and metathesis of olefins (a novel kind of disproportionation). Enantioselective catalysis that rivals enzymes in selectivity is a major development in homogeneous catalysis. As a result, many earlier processes in the pharmaceutical and perfumery industries are being replaced by more elegant syntheses using soluble catalysts in which “handedness” is introduced in the critical step of the process, thus avoiding the costly separation of racemic mixtures. In view of its importance in organic synthesis, enantioselective (or asymmetric) catalysis was briefly introduced in Chapter 6 and is again considered as a powerful synthetic tool in Chapter 9. This chapter is concerned with the use in general of homogeneous catalysis in organic synthesis (including asymmetric synthesis). Among the several books and reviews written on the subject, the following may be mentioned: Halpern (1975, 1982), Bau et al. (1978), Parshall (1980), Masters (1981), Collman and Hegedus (1980), Eby and Singleton (1983), Chaudhari (1984), Davidson (1984), Kegley and Pinhas (1986), Collman et al. (1987), Parshall and Nugent (1988), Noyori and Kitamura (1989), Parshall and Ittel (1992), Gates (1992), Chan (1993), Akutagawa (1995). Gas (or liquid)-phase reactions on solid catalysts are among the most common industrial reactions. However, homogeneous catalysis is rapidly catching up. Excluding applications in petroleum refining, the dollar value of organic chemicals produced worldwide by homogeneous catalysis (more than $35 billion) is quite impressive compared to that by heterogeneous catalysis (more than $45 billion). Attempts are now under way to find an integrated approach to homogeneous and heterogeneous catalyses (Moulijn et al., 1993).

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Joó, F. "Alkanes by Hydrogenation of Alkenes with Water-Soluble Analogues of Wilkinsonʼs Catalyst." In Water in Organic Synthesis, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-206-00078.

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