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Journal articles on the topic 'Hydroformylation of Alkenes'

Author: Grafiati

Published: 6 September 2023

Last updated: 31 July 2025

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1

Shi, Yukun, Yang Lu, Tongxin Ren, et al. "Rh Particles Supported on Sulfated g-C3N4: A Highly Efficient and Recyclable Heterogeneous Catalyst for Alkene Hydroformylation." Catalysts 10, no. 11 (2020): 1359. http://dx.doi.org/10.3390/catal10111359.

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The hydroformylation of alkenes with CO and H2 to manufacture aldehydes is one of the most large-scale chemical reactions. However, an efficient and recyclable heterogeneous catalyst for alkene hydroformylation is extremely in demand in academia and industry. In this study, a sulfated carbon nitride supported rhodium particle catalyst (Rh/S-g-C3N4) was successfully synthesized via an impregnation-borohydride reduction method and applied in the hydroformylation of alkenes. The catalysts were characterized by XRD, FTIR, SEM, TEM, XPS, and nitrogen adsorption. The influence of the sulfate content

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2

Prakash, D., B. Pant, and P. Sagar. "Hydroformylation of Terminal Alkenes with in situ Generation of Syngas using Schiff Base Palladium Complex under Microwave and Conventional Heating." Asian Journal of Chemistry 36, no. 6 (2024): 1281–85. http://dx.doi.org/10.14233/ajchem.2024.31390.

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Hydroformylation of alkenes and alkynes without syngas is preferred for obtaining valuable aldehydes with 100% atom economy using widely available components. Regarding selectivity, atom economy and energy efficiency, microwave-promoted catalytic hydroformylation reactions are the substitutes for conventional techniques. This is compatible with an increasing demand for more environmentally friendly industrial processes. In present work, Schiff base palladium complexes were utilized as catalysts for the hydroformylation of terminal alkenes using glyoxylic acid and formaldehyde as sources of CO

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3

Doyle, MM, WR Jackson, and P. Perlmutter. "The Stereochemistry of Organometallic Compounds. XXXIV. Regioselection in the Hydroformylation of Silylalkenes." Australian Journal of Chemistry 42, no. 11 (1989): 1907. http://dx.doi.org/10.1071/ch9891907.

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The regiochemistry of hydroformylation of alkenes can be controlled by the use of bulky silyl groups attached to the alkene. Use of the t-butyldiphenylsilyl group leads to almost total regiocontrol and the method has been applied to the synthesis of aldols.

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4

Hood, Drew M., Ryan A. Johnson, Alex E. Carpenter, Jarod M. Younker, David J. Vinyard, and George G. Stanley. "Highly active cationic cobalt(II) hydroformylation catalysts." Science 367, no. 6477 (2020): 542–48. http://dx.doi.org/10.1126/science.aaw7742.

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The cobalt complexes HCo(CO)4 and HCo(CO)3(PR3) were the original industrial catalysts used for the hydroformylation of alkenes through reaction with hydrogen and carbon monoxide to produce aldehydes. More recent and expensive rhodium-phosphine catalysts are hundreds of times more active and operate under considerably lower pressures. Cationic cobalt(II) bisphosphine hydrido-carbonyl catalysts that are far more active than traditional neutral cobalt(I) catalysts and approach rhodium catalysts in activity are reported here. These catalysts have low linear-to-branched (L:B) regioselectivity for

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5

Yu, Xuetong, Yuxia Ji, Yan Jiang, Rui Lang, Yanxiong Fang, and Botao Qiao. "Recent Development of Single-Atom Catalysis for the Functionalization of Alkenes." Catalysts 13, no. 4 (2023): 730. http://dx.doi.org/10.3390/catal13040730.

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The functionalization of alkenes is one of the most important conversions in synthetic chemistry to prepare numerous fine chemicals. Typical procedures, such as hydrosilylation and hydroformylation, are traditionally catalyzed using homogeneous noble metal complexes, while the highly reactive and stable heterogeneous single-atom catalysts (SACs) now provide alternative approaches to fulfill these conversions by combining the advantages of both homogeneous catalysts and heterogeneous nanoparticle catalysts. In this review, the recent achievement in single-atom catalyzed hydrosilylation and hydr

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6

Geng, Hui-Qing, Tim Meyer, Robert Franke, and Xiao-Feng Wu. "Copper-catalyzed hydroformylation and hydroxymethylation of styrenes." Chemical Science 12, no. 44 (2021): 14937–43. http://dx.doi.org/10.1039/d1sc05474k.

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7

Peral, Daniel, Daniel Herrera, Julio Real, Teresa Flor та J. Carles Bayón. "Strong π-acceptor sulfonated phosphines in biphasic rhodium-catalyzed hydroformylation of polar alkenes". Catalysis Science & Technology 6, № 3 (2016): 800–808. http://dx.doi.org/10.1039/c5cy01004g.

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8

Chevry, M., T. Vanbésien, S. Menuel, E. Monflier, and F. Hapiot. "Tetronics/cyclodextrin-based hydrogels as catalyst-containing media for the hydroformylation of higher olefins." Catalysis Science & Technology 7, no. 1 (2017): 114–23. http://dx.doi.org/10.1039/c6cy02070d.

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9

Shi, Yukun, Gang Ji, Qiqige Hu, et al. "Highly uniform Rh nanoparticles supported on boron doped g-C3N4 as a highly efficient and recyclable catalyst for heterogeneous hydroformylation of alkenes." New Journal of Chemistry 44, no. 1 (2020): 20–23. http://dx.doi.org/10.1039/c9nj05385a.

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10

Nandakumar, Avanashiappan, Manoj K. Sahoo, and Ekambaram Balaraman. "Reverse-hydroformylation: a missing reaction explored." Organic Chemistry Frontiers 2, no. 10 (2015): 1422–24. http://dx.doi.org/10.1039/c5qo00229j.

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Recent progress in transition-metal catalysed acceptor- and acceptorless-reverse hydroformylation of aldehydes for the conversion of olefins has been discussed. The aldehyde feedstock serves as a source for production of syngas and valuable alkenes.

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11

Wu, Lipeng, Qiang Liu, Anke Spannenberg, Ralf Jackstell, and Matthias Beller. "Highly regioselective osmium-catalyzed hydroformylation." Chemical Communications 51, no. 15 (2015): 3080–82. http://dx.doi.org/10.1039/c4cc05626d.

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Osmium carbonyl combined with 2-imidazoyl-substituted phosphine ligands forms active species for the highly regioselective and general hydroformylation of alkenes to produce aldehydes in good yields and excellent regioselectivities. An unusual phosphido bridged trinuclear osmium catalyst structure was obtained.

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12

Krupčík, Ján, and Dušan Repka. "Analysis of hydroformylation products of higher n-alkenes by capillary gas chromatography." Collection of Czechoslovak Chemical Communications 50, no. 8 (1985): 1808–18. http://dx.doi.org/10.1135/cccc19851808.

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A mixture of alcohols obtained by hydroformylation of C10-C13 n-alkenes was analyzed by capillary gas chromatography using Carbowax 20M stationary phase, and acetates prepared from the alcohols were analyzed on capillary columns using Carbowax 20M and Apiezon L stationary phases. The capillary gas chromatography and gas chromatography-mass spectrometry treatment gave evidence that all of the 24 alcohols that could form by the hydroformylation reaction mechanism were present.

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13

Terhorst, M., C. Plass, A. Hinzmann, et al. "One-pot synthesis of aldoximes from alkenes via Rh-catalysed hydroformylation in an aqueous solvent system." Green Chemistry 22, no. 22 (2020): 7974–82. http://dx.doi.org/10.1039/d0gc03141k.

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Aldoxime synthesis directly starting from alkenes was successfully achieved through the combination of hydroformylation and subsequent condensation of the aldehyde intermediate with aqueous hydroxylamine in a one-pot process.

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14

Bibouche, Bachir, Daniel Peral, Dmitrij Stehl, et al. "Multiphasic aqueous hydroformylation of 1-alkenes with micelle-like polymer particles as phase transfer agents." RSC Advances 8, no. 41 (2018): 23332–38. http://dx.doi.org/10.1039/c8ra04022b.

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Micelle-like polyelectrolyte polymer particles were applied as phase transfer agents and catalyst carriers in the multiphasic hydroformylation of long chain alkenes achieving high turnover frequencies and efficient catalyst recovery.

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15

Kämper, Alexander, Peter Kucmierczyk, Thomas Seidensticker, Andreas J. Vorholt, Robert Franke, and Arno Behr. "Ruthenium-catalyzed hydroformylation: from laboratory to continuous miniplant scale." Catalysis Science & Technology 6, no. 22 (2016): 8072–79. http://dx.doi.org/10.1039/c6cy01374k.

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Ruthenium running its rounds – recycling of a homogeneous ruthenium catalyst for hydroformylation of linear aliphatic alkenes by ex situ product extraction and successful application in a continuously operated miniplant for 90 h.

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16

Imam, Hasan T., Amanda G. Jarvis, Veronica Celorrio, et al. "Catalytic and biophysical investigation of rhodium hydroformylase." Catalysis Science & Technology 9, no. 22 (2019): 6428–37. http://dx.doi.org/10.1039/c9cy01679a.

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Rh-Containing artificial metalloenzymes based on two mutants of sterol carrier protein_2L (SCP_2L) have been shown to act as hydroformylases, exhibiting significant activity and unexpectedly high selectivity in the hydroformylation of alkenes.

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17

Liu, Yan-li, Jian-gui Zhao, Yuan-jiang Zhao, et al. "Homogeneous hydroformylation of long chain alkenes catalyzed by water soluble phosphine rhodium complex in CH3OH and efficient catalyst cycling." RSC Advances 9, no. 13 (2019): 7382–87. http://dx.doi.org/10.1039/c8ra08787c.

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Hydroformylation of long-chain alkenes proceeded homogeneously in methanol efficiently. The catalyst could be separated heterogeneously when methanol was removed and recycled for four times without obvious loss in catalytic performance and rhodium.

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18

Takeuchi, Ryo, and Nobuhiro Sato. "Hydroformylation of alkenes having organosilicon substituents." Journal of Organometallic Chemistry 393, no. 1 (1990): 1–10. http://dx.doi.org/10.1016/0022-328x(90)87193-h.

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19

Kardasheva, Yulia, Maria Terenina, Daniil Sokolov, Natalia Sinikova, Sergey Kardashev, and Eduard Karakhanov. "Hydroformylation of Alkenes over Phosphorous-Free Rhodium Supported on N-Doped Silica." Catalysts 13, no. 5 (2023): 818. http://dx.doi.org/10.3390/catal13050818.

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A new phosphorous-free rhodium supported on a nitrogen-doped silica was successfully used as a catalyst for the hydroformylation of alkenes. The obtained material and the catalyst were characterized by XRD, XPS, FTIR, SEM, TEM, ICP AES, and low-temperature nitrogen adsorption–desorption measurements. The catalytic performance was studied by the example of the hydroformylation of octene-1 at temperatures of 80–140 °C and a pressure of 5.0 MPa. The catalyst provided a 99% conversion of 1-octene with a 98% yield of aldehydes and showed a good conversion of styrene and cyclohexene. The catalyst ca

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20

Zhang, Yang, Michel Sigrist, and Paweł Dydio. "Palladium‐Catalyzed Hydroformylation of Alkenes and Alkynes." European Journal of Organic Chemistry 2021, no. 44 (2021): 5985–97. http://dx.doi.org/10.1002/ejoc.202101020.

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21

Reek, J., M. Kuil, T. Soltner, and P. van Leeuwen. "Hydroformylation of Internal Alkenes by Encapsulated Rhodium." Synfacts 2006, no. 12 (2006): 1262. http://dx.doi.org/10.1055/s-2006-949501.

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22

Sharma, Sumeet K., and Raksh V. Jasra. "Aqueous phase catalytic hydroformylation reactions of alkenes." Catalysis Today 247 (June 2015): 70–81. http://dx.doi.org/10.1016/j.cattod.2014.07.059.

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23

Cocq, Aurélien, Hervé Bricout, Florence Djedaïni-Pilard, Sébastien Tilloy, and Eric Monflier. "Rhodium-Catalyzed Aqueous Biphasic Olefin Hydroformylation Promoted by Amphiphilic Cyclodextrins." Catalysts 10, no. 1 (2020): 56. http://dx.doi.org/10.3390/catal10010056.

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Hydroformylation is an industrial process that allows for the production of aldehydes from alkenes using transition metals. The reaction can be carried out in water, and the catalyst may be recycled at the end of the reaction. The industrial application of rhodium-catalyzed aqueous hydroformylation has been demonstrated for smaller olefins (propene and butene). Unfortunately, larger olefins are weakly soluble in water, which results in very low catalytic activity. In an attempt to counteract this, we investigated the use of amphiphilic oleic succinyl-cyclodextrins (OS-CDs) synthesized from ole

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24

Fuentes, José A., Mesfin E. Janka, Aidan P. McKay, et al. "Ligand Hydrogenation during Hydroformylation Catalysis Detected by In Situ High-Pressure Infra-Red Spectroscopic Analysis of a Rhodium/Phospholene-Phosphite Catalyst." Molecules 29, no. 4 (2024): 845. http://dx.doi.org/10.3390/molecules29040845.

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Phospholane-phosphites are known to show highly unusual selectivity towards branched aldehydes in the hydroformylation of terminal alkenes. This paper describes the synthesis of hitherto unknown unsaturated phospholene borane precursors and their conversion to the corresponding phospholene-phosphites. The relative stereochemistry of one of these ligands and its Pd complex was assigned with the aid of X-ray crystal structure determinations. These ligands were able to approach the level of selectivity observed for phospholane-phosphites in the rhodium-catalysed hydroformylation of propene. High-

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25

Zhang, Xiaoli, Juan Wei, and Xiaoming Zhang. "Encapsulated liquid nano-droplets for efficient and selective biphasic hydroformylation of long-chain alkenes." New Journal of Chemistry 43, no. 35 (2019): 14134–38. http://dx.doi.org/10.1039/c9nj02493j.

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26

Jackson, W. Roy, Patrick Parlmutter, and Guem-Hee Suh. "Chelation control in the hydroformylation of terminal alkenes." Journal of the Chemical Society, Chemical Communications, no. 10 (1987): 724. http://dx.doi.org/10.1039/c39870000724.

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27

Tao, Lin, Mingmei Zhong, Jian Chen, et al. "Heterogeneous hydroformylation of long-chain alkenes in IL-in-oil Pickering emulsion." Green Chemistry 20, no. 1 (2018): 188–96. http://dx.doi.org/10.1039/c7gc02574b.

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An IL-in-oil Pickering emulsion prepared with Rh-sulfo-xantphos as the catalyst and dendritic mesoporous silica nanospheres as the stabilizer could efficiently catalyze the hydroformylation of 1-dodecene to afford TOF as high as 413 h<sup>−1</sup>.

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28

Meyer, Wolfgang H., Richard J. Bowen, and David G. Billing. "Tri(3-pyridyl)phosphine as Amphiphilic Ligand in the Rhodium-catalysed Hydroformylation of 1-Hexene." Zeitschrift für Naturforschung B 62, no. 3 (2007): 339–45. http://dx.doi.org/10.1515/znb-2007-0306.

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The molecular structure of carbonylchlorobis(tri(3-pyridyl)phosphine)rhodium, 1, has been determined by X-ray diffraction methods. The N-protonated trifluoromethanesulfonate (triflate) complex 3 was synthesised as a model compound for the extraction of a rhodium complex bearing amphiphilic ligands which can allow catalyst recycling in the hydroformylation of alkenes by using their distribution behavior in organic and aqueous solvents of different pH. The high water-solubility of the employed ligand renders the recycling method as only partly successful due to insufficient extraction from the w

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29

Breit, Bernhard, and Wolfgang Seiche. "Self-assembly of bidentate ligands for combinatorial homogeneous catalysis based on an A-T base pair model." Pure and Applied Chemistry 78, no. 2 (2006): 249–56. http://dx.doi.org/10.1351/pac200678020249.

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A new concept for generation of chelating ligand libraries for homogeneous metal complex catalysis based on self-assembly is presented. Thus, self-assembly of structurally simple monodentate ligands in order to give structurally more complex bidentate ligands is achieved employing hydrogen bonding. Based on this concept and on the 2-pyridone/hydroxypyridine tautomeric system, a new rhodium catalyst was identified which operated with excellent activity and regioselectivity upon hydroformylation of terminal alkenes. In order to generate defined unsymmetrical heterodimeric ligands, an A-T base pa

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30

Adams, Dave J., James A. Bennett, David J. Cole-Hamilton, et al. "Rhodium catalysed hydroformylation of alkenes using highly fluorophilic phosphines." Dalton Transactions, no. 24 (2005): 3862. http://dx.doi.org/10.1039/b510766k.

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31

Desset, Simon L., Simon W. Reader, and David J. Cole-Hamilton. "Aqueous-biphasic hydroformylation of alkenes promoted by “weak” surfactants." Green Chemistry 11, no. 5 (2009): 630. http://dx.doi.org/10.1039/b822139a.

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32

Watkins, Avery L., Brian G. Hashiguchi, and Clark R. Landis. "Highly Enantioselective Hydroformylation of Aryl Alkenes with Diazaphospholane Ligands." Organic Letters 10, no. 20 (2008): 4553–56. http://dx.doi.org/10.1021/ol801723a.

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33

Tominaga, Ken-ichi, and Yoshiyuki Sasaki. "Ruthenium complex-catalyzed hydroformylation of alkenes with carbon dioxide." Catalysis Communications 1, no. 1-4 (2000): 1–3. http://dx.doi.org/10.1016/s1566-7367(00)00006-6.

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34

Achonduh, George, Qian Yang, and Howard Alper. "From alkenes to alcohols by cobalt-catalyzed hydroformylation–reduction." Tetrahedron 71, no. 8 (2015): 1241–46. http://dx.doi.org/10.1016/j.tet.2015.01.006.

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35

MacDougall, Joanna K., and David J. Cole-Hamilton. "Alcohols as sources of hydrogen in hydroformylation of alkenes." Polyhedron 9, no. 9 (1990): 1235–36. http://dx.doi.org/10.1016/s0277-5387(00)86901-6.

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36

Webb, Paul B., Thulani E. Kunene, and David J. Cole-Hamilton. "Continuous flow homogeneous hydroformylation of alkenes using supercritical fluids." Green Chemistry 7, no. 5 (2005): 373. http://dx.doi.org/10.1039/b416713a.

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37

Murzin, Dmitry Yu, Andreas Bernas, and Tapio Salmi. "Kinetic modelling of regioselectivity in alkenes hydroformylation over rhodium." Journal of Molecular Catalysis A: Chemical 315, no. 2 (2010): 148–54. http://dx.doi.org/10.1016/j.molcata.2009.06.023.

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38

Sharma, Sumeet K., and Raksh V. Jasra. "ChemInform Abstract: Aqueous Phase Catalytic Hydroformylation Reactions of Alkenes." ChemInform 46, no. 21 (2015): no. http://dx.doi.org/10.1002/chin.201521286.

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39

Buhling, Armin, Paul C. J. Kamer, and Piet W. N. M. van Leeuwen. "Rhodium catalysed hydroformylation of higher alkenes using amphiphilic ligands." Journal of Molecular Catalysis A: Chemical 98, no. 2 (1995): 69–80. http://dx.doi.org/10.1016/1381-1169(95)00014-3.

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40

Fehrmann, Rasmus, Anders Riisager, Eduardo Jose Garcia-Suarez, and Le Minh Thang. "Hydroformylation of Alkenes by Supported Ionic Liquid Phase (SILP) Catalysis." ECS Meeting Abstracts MA2024-02, no. 57 (2024): 3881. https://doi.org/10.1149/ma2024-02573881mtgabs.

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Hydroformylation of olefins forms aldehydes which are valuable final products as well as intermediates in synthesizing bulk chemicals like alcohols, amines, and esters with a yearly world production of about 12 Mt. Industrial hydroformylation processes are essentially homogeneously catalyzed systems with an economic incitement for improvement by easy separation of products and reuse of catalysts, high reactivity and selectivity by using new catalysts, novel processes and alternative methodologies. One such potential candidate for an alternative catalyst is a Supported Ionic Liquid- Phase (SILP

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41

Fuchs, Evelyn, Manfred Keller, and Bernhard Breit. "Phosphabarrelenes as Ligands in Rhodium-Catalyzed Hydroformylation of Internal Alkenes Essentially Free of Alkene Isomerization." Chemistry - A European Journal 12, no. 26 (2006): 6930–39. http://dx.doi.org/10.1002/chem.200600180.

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42

Desset, Simon L., David J. Cole-Hamilton, and Douglas F. Foster. "Aqueous-biphasic hydroformylation of higher alkenes promoted by alkylimidazolium salts." Chemical Communications, no. 19 (2007): 1933. http://dx.doi.org/10.1039/b618785d.

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43

Wildt, Julia, Anna C. Brezny, and Clark R. Landis. "Backbone-Modified Bisdiazaphospholanes for Regioselective Rhodium-Catalyzed Hydroformylation of Alkenes." Organometallics 36, no. 16 (2017): 3142–51. http://dx.doi.org/10.1021/acs.organomet.7b00475.

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44

Deng, Yuchao, Hui Wang, Yuhan Sun, and Xiao Wang. "Principles and Applications of Enantioselective Hydroformylation of Terminal Disubstituted Alkenes." ACS Catalysis 5, no. 11 (2015): 6828–37. http://dx.doi.org/10.1021/acscatal.5b01300.

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45

Rosales, Merlin, Angel González, Beatríz González, et al. "Hydroformylation of alkenes with paraformaldehyde catalyzed by rhodium–phosphine complexes." Journal of Organometallic Chemistry 690, no. 12 (2005): 3095–98. http://dx.doi.org/10.1016/j.jorganchem.2005.03.032.

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46

Yu, Zhiyong, Meredith S. Eno, Alexandra H. Annis, and James P. Morken. "Enantioselective Hydroformylation of 1-Alkenes with Commercial Ph-BPE Ligand." Organic Letters 17, no. 13 (2015): 3264–67. http://dx.doi.org/10.1021/acs.orglett.5b01421.

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47

Polas, Anastasios, James D. E. T. Wilton-Ely, Alexandra M. Z. Slawin, et al. "Limonene-derived phosphines in the cobalt-catalysed hydroformylation of alkenes." Dalton Transactions, no. 24 (2003): 4669. http://dx.doi.org/10.1039/b310233e.

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48

Pedrós, Marta Giménez, Anna M. Masdeu-Bultó, Jerome Bayardon, and Denis Sinou. "Hydroformylation of Alkenes with Rhodium Catalyst in Supercritical Carbon Dioxide." Catalysis Letters 107, no. 3-4 (2006): 205–8. http://dx.doi.org/10.1007/s10562-005-0005-7.

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49

Yamane, Motoki, Noriaki Yukimura, Hiroshi Ishiai, and Koichi Narasaka. "Hydroformylation of Monosubstituted Alkenes Catalyzed by W–Rh Bimetallic Complex." Chemistry Letters 35, no. 5 (2006): 540–41. http://dx.doi.org/10.1246/cl.2006.540.

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50

Kamer, Paul C. J., Annemiek van Rooy, Gerard C. Schoemaker, and Piet W. N. M. van Leeuwen. "In situ mechanistic studies in rhodium catalyzed hydroformylation of alkenes." Coordination Chemistry Reviews 248, no. 21-24 (2004): 2409–24. http://dx.doi.org/10.1016/j.ccr.2004.06.006.

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