The influence of different monodentate P-ligand mixtures on Rh-catalyzed 1-butene hydroformylation

doi:10.1016/j.cjche.2018.05.018

Chinese Journal of Chemical Engineering ›› 2018, Vol. 26 ›› Issue (9): 1943-1948.DOI: 10.1016/j.cjche.2018.05.018

• Catalysis, Kinetics and Reaction Engineering • 上一篇下一篇

The influence of different monodentate P-ligand mixtures on Rh-catalyzed 1-butene hydroformylation

Weili Jiang^1,2, Jinxin Chu¹, Jie Yang¹, Pengyu Zang¹, Lijie Gao¹, Guanglin Zhou¹, Hongjun Zhou¹, Huibo Wei³

1 Institute of New Energy, Beijing Key Laboratory of Biogas Upgrading Utilization, China University of Petroleum, Beijing 102249, China;
2 Department of Chemistry, University of California, Riverside, CA 92521, USA;
3 Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

收稿日期:2017-06-21 修回日期:2018-05-17 出版日期:2018-09-28 发布日期:2018-10-17
通讯作者: Hongjun Zhou,E-mail address:zhhj63@163.com
基金资助:
Supported by the National Natural Science Foundation of China (21306227) and the Science Foundation of China University of Petroleum, Beijing (C201604).

The influence of different monodentate P-ligand mixtures on Rh-catalyzed 1-butene hydroformylation

Weili Jiang^1,2, Jinxin Chu¹, Jie Yang¹, Pengyu Zang¹, Lijie Gao¹, Guanglin Zhou¹, Hongjun Zhou¹, Huibo Wei³

1 Institute of New Energy, Beijing Key Laboratory of Biogas Upgrading Utilization, China University of Petroleum, Beijing 102249, China;
2 Department of Chemistry, University of California, Riverside, CA 92521, USA;
3 Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

Received:2017-06-21 Revised:2018-05-17 Online:2018-09-28 Published:2018-10-17
Contact: Hongjun Zhou,E-mail address:zhhj63@163.com
Supported by:
Supported by the National Natural Science Foundation of China (21306227) and the Science Foundation of China University of Petroleum, Beijing (C201604).

摘要/Abstract

摘要： Four monodentate P-ligands and their mixtures (six groups of double-ligand systems, four groups of triple-ligand systems and one group of tetra-ligand system) were used with Rh(acac)(CO)₂ (acac=acetylacetonate) or Rh (acac)CO(PPh₃) as the catalyst in the hydroformylation reaction of 1-butene. It was found that different Rh catalysts showed little difference in the catalysis performance. The general order of catalysis performance is doubleligand system > single-ligand system > triple-ligand system > tetra-ligand system. Some synergistic effect in the double-ligand system was detected which needs a further investigation.

关键词: Homogeneous catalysis, Hydroformylation, Syngas, 1-Butene, Rhodium catalyst

Abstract: Four monodentate P-ligands and their mixtures (six groups of double-ligand systems, four groups of triple-ligand systems and one group of tetra-ligand system) were used with Rh(acac)(CO)₂ (acac=acetylacetonate) or Rh (acac)CO(PPh₃) as the catalyst in the hydroformylation reaction of 1-butene. It was found that different Rh catalysts showed little difference in the catalysis performance. The general order of catalysis performance is doubleligand system > single-ligand system > triple-ligand system > tetra-ligand system. Some synergistic effect in the double-ligand system was detected which needs a further investigation.

Key words: Homogeneous catalysis, Hydroformylation, Syngas, 1-Butene, Rhodium catalyst

Weili Jiang, Jinxin Chu, Jie Yang, Pengyu Zang, Lijie Gao, Guanglin Zhou, Hongjun Zhou, Huibo Wei. The influence of different monodentate P-ligand mixtures on Rh-catalyzed 1-butene hydroformylation[J]. Chinese Journal of Chemical Engineering, 2018, 26(9): 1943-1948.

参考文献

[1] S. Bhaduri, D. Mukesh, Homogeneous Catalysis:Mechanisms and Industrial Applications, John Weliy & Sons Inc., New York, 2000.

[2] X.F. Jia, Z. Wang, C.G. Xia, K.L. Ding, Recent advances in Rh-catalyzed asymmetric hydroformylation of olefins, Chin. J. Org. Chem. 33(2013) 1369-1381.

[3] D. Peral, D. Stehl, B. Bibouche, H. Yu, J. Mardoukh, R. Schomaecker, R. von Klitzing, D. Vogt, Colloidal polymer particles as catalyst carriers and phase transfer agents in multiphasic hydroformylation reactions, J. Colloid Interface Sci. 513(2018) 638-646.

[4] S. Walter, H. Spohr, R. Franke, W. Hieringer, P. Wasserscheid, M. Haumann, Detailed investigation of the mechanism of Rh-diphosphite supported ionic liquid phase (SILP)-catalyzed 1-butene hydroformylation in the gas phase via combined kinetic and density functional theory (DFT) modeling studies, ACS Catal. 7(2017) 1035-1044.

[5] X. Li, K. Zhang, L. Qin, H. Ma, Kinetic studies of hydroformylation of 1-butene using homogeneous Rh/PPh3 complex catalyst, Mol. Catal. 443(2017)270-279.

[6] Y. Wang, L. Yan, C. Li, M. Jiang, W. Wang, Y. Ding, Highly efficient porous organic copolymer supported Rh catalysts for heterogeneous hydroformylation of butenes, Appl. Catal. A Gen. 551(2018) 98-105.

[7] R. Franke, D. Selent, A. Borner, Applied hydroformylation, Chem. Rev. 112(2012) 5675-5732.

[8] D.N. Gorbunov, A.V. Volkov, Y.S. Kardasheva, A.L. Maksimov, E.A. Karakhanov, Hydroformylation in petroleum chemistry and organic synthesis:Implementation of the process and solving the problem of recycling homogeneous catalysts (review), Pet. Chem. 55(2015) 587-603.

[9] H. Warmeling, D. Hafki, T. von Soehnen, A.J. Vorholt, Kinetic investigation of lean aqueous hydroformylation-An engineer's view on homogeneous catalysis, Chem. Eng. J. 326(2017)298-307.

[10] P.W.N.M.v. Leeuwen, J.C. Chadwick, Homogeneous Catalysts, Wiley-VCH Verlag & Co. KGaA, Weinheim, 2011.

[11] J. Pospech, I. Fleischer, R. Franke, S. Buchholz, M. Beller, Alternative metals for homogeneous catalyzed hydroformylation reactions, Angew. Chem. Int. Ed. 52(2013)2852-2872.

[12] Z.S. Mao, X.Y. Bi, G.Z. Yu, Y.Q. Zhang, C. Yang, R. Wang, Preliminary exploration of the reactor configuration for hydroformylation of 1-dodecene catalyzed by water soluble rhodium complex, Chin. J. Chem. Eng. 10(2002) 45-51.

[13] S. Aguado-Ullate, J.A. Baker, V. Gonzalez-Gonzalez, C. Muller, J.D. Hirst, J.J. Carbo, A theoretical study of the activity in Rh-catalysed hydroformylation:The origin of the enhanced activity of the pi-acceptor phosphinine ligand, Catal. Sci. Technol. 4(2014) 979-987.

[14] M. Kumar, R.V. Chaudhari, B. Subramaniam, T.A. Jackson, Ligand effects on the regioselectivity of rhodium-catalyzed hydroformylation:Density functional calculations illuminate the role of long-range noncovalent interactions, Organometallics 33(2014) 4183-4191.

[15] C. Muller, D. Vogt, Phosphinines as ligands in homogeneous catalysis:Recent developments, concepts and perspectives, Dalton Trans. (2007) 5505-5523.

[16] M. Peruzzini, L. Gonsalvi, in:C. Bianchini, D.J. Cole-Hamilton, P.W.N.M.v. Leeuwen (Eds.), Phosphorus Compounds:Advanced Tools in Catalysis and Material Sciences, Catalysis by Metal Complexes, Springer, London, 2011.

[17] M.A.S. Garcia, M. Ibrahim, J.C.S. Costa, P. Corio, E.V. Gusevskaya, E.N. dos Santos, K. Philippot, L.M. Rossi, Study of the influence of PPh3 used as capping ligand or as reaction modifier for hydroformylation reaction involving Rh NPs as precatalyst, Appl. Catal. A Gen. 548(2017) 136-142.

[18] A. Buhling, P.C.J. Kamer, P.W.N.M.v. Leeuwen, Rhodium catalysed hydroformylation of higher alkenes using amphiphilic ligands, J. Mol. Catal. A Chem. 98(1995) 69-80.

[19] A.C.J. Koeken, N.M.B. Smeets, A bulky phosphite modified rhodium catalyst for efficient hydroformylation of disubstituted alkenes and macromonomers in supercritical carbon dioxide, Catal. Sci. Technol. 3(2013) 1036-1045.

[20] G.N. Costa, R.M.B. Carrilho, L.D. Dias, J.C. Viana, G.L.B. Aquino, M. Pineiro, M.M. Pereira, Highly efficient Rh(I)/tris-binaphthyl monophosphite catalysts for hydroformylation of sterically hindered alkyl olefins, J. Mol. Catal. A Chem. 416(2016) 73-80.

[21] M. Yuan, H. Chen, R.X. Li, Y.Z. Li, X.J. Li, High active and regioselective hydroformylation of 1-dodecene catalyzed by Rh-BISBIS in a two-phase system, Catal. Lett. 94(2004) 15-16.

[22] Y.Y. Wang, J.H. Chen, M.M. Luo, H. Chen, X.J. Li, Highly regioselective hydroaminomethylation of long chain alkenes catalyzed by Rh-BISBIS in a twophase system, Catal. Commun. 7(2006) 979-981.

[23] L.A. van der Veen, P.H. Keeven, G.C. Schoemaker, J.N.H. Reek, P.C.J. Kamer, P.W.N.M. van Leeuwen, M. Lutz, A.L. Spek, Origin of the bite angle effect on rhodium diphosphine catalyzed hydroformylation, Organometallics 19(2000) 872-883.

[24] L. Le Goanvic, J. Ternel, J.-L. Couturier, J.-L. Dubois, J.-F. Carpentier, Rhodiumbiphephos-catalyzed tandem isomerization-hydroformylation of oleonitrile, Catalysts 8(2018), https://doi.org/10.3390/catal8010021.

[25] J.R. Logan, W.E. Piers, J. Borau-Garcia, D.M. Spasyuk, Ligand attachment chemistry in the preparation of (PCspP)-P-3 and (PCspP)-P-2 complexes of rhodium, Organometallics 35(2016) 1279-1286.

[26] Z.P. Zhang, Q. Wang, C.Y. Chen, Z.Y. Han, X.Q. Dong, X.M. Zhang, Selective rhodiumcatalyzed hydroformylation of alkynes to alpha,beta-unsaturated aldehydes with a tetraphosphoramidite ligand, Org. Lett. 18(2016) 3290-3293.

[27] K. Saikia, B. Deb, D.K. Dutta, Synthesis of cationic rhodium(I) and iridium(I) carbonyl complexes of tetradentate P(CH2CH2PPh2)(3) ligand:An implication of steric inhibition and catalytic hydroformylation reaction, J. Mol. Catal. A Chem. 381(2014) 188-193.

[28] C. You, S. Li, X. Li, J. Lan, Y. Yang, L.W. Chung, H. Lv, X. Zhang, Design and application of hybrid phosphorus ligands for enantioselective Rh-catalyzed anti-Markovnikov hydroformylation of unfunctionalized 1,1-disubstituted alkenes, J. Am. Chem. Soc. 140(2018) 4977-4981.

[29] S.H. Chikkali, J.I. van der Vlugt, J.N.H. Reek, Hybrid diphosphorus ligands in rhodium catalysed asymmetric hydroformylation, Coord. Chem. Rev. 262(2014) 1-15.

[30] Y.J. Yan, X.M. Zhang, A hybrid phosphorus ligand for highly enantioselective asymmetric hydroformylation, J. Am. Chem. Soc. 128(2006) 7198-7202.

[31] S.H. Chikkali, R. Bellini, G. Berthon-Gelloz, J.I. van der Vlugt, B. Bruin, J.N.H. Reek, Highly enantioselective hydroformylation of dihydrofurans catalyzed by hybrid phosphine-phosphonite rhodium complexes, Chem. Commun. 46(2010) 1244-1246.

[32] R. Bellini, J.N.H. Reek, Application of supramolecular bidentate hybrid ligands in asymmetric hydroformylation, Chem. Eur. J. 18(2012) 13510-13519.

[33] S. Chen, E. Manoury, R. Poli, Slow exchange of bidentate ligands between rhodium (I) complexes:Evidence of both neutral and anionic ligand exchange, Eur. J. Inorg. Chem. (2014) 5820-5826.

[34] M.T. Reetz, Combinatorial transition-metal catalysis:Mixing monodentate ligands to control enantio-, diastereo-, and regioselectivity, Angew. Chem. Int. Ed. 47(2008)2556-2588.

[35] M.T. Reetz, T. Sell, A. Meiswinkel, G. Mehler, A new principle in combinatorial asymmetric transition-metal catalysis:Mixtures of chiral monodentate P ligands, Angew. Chem. Int. Ed. 42(2003) 790-793.

[36] M.T. Reetz, X.G. Li, The influence of mixtures of monodentate achiral ligands on the regioselectivity of transition-metal-catalyzed hydroformylation, Angew. Chem. Int. Ed. 44(2005)2962-2964.

[37] S. Lou, H. Jiang, Theoretical study of adsorption of organic phosphines on transition metal surfaces, Mol. Phys. 116(2018) 944-955.

[38] M. Mo, T. Yi, C.Y. Zheng, M.L. Yuan, H.Y. Fu, R.X. Li, H. Chen, Highly regioselective and active rhodium/bisphosphite catalytic system for isomerization-hydroformylation of 2-butene, Catal. Lett. 142(2012)238-242.

[39] T. Salmi, J. Ahlkvist, A. Bernas, J. Warna, P. Maki-Arvela, C. Still, J. Lehtonen, D.Y. Murzin, Hydroformylation of 1-butene on Rh catalyst, Ind. Eng. Chem. Res. 48(2009) 1325-1331.

[40] C. Li, W. Wang, L. Yan, Y. Ding, A mini review on strategies for heterogenization of rhodium-based hydroformylation catalysts, Front. Chem. Sci. Eng. 12(2018) 113-123.

[41] W. Jiang, Y. Gao, Y. Sun, F. Ding, Y. Xu, Z. Bian, F.Li, J. Bian, C. Huang,Zwitterionic iridium complexes:Synthesis, luminescent properties, and their application in cell imaging, Inorg. Chem. 49(2010) 3252-3260.

[42] K. Kurtev, D. Ribola, R.A. Jones, D.J. Colehamilton, G. Wilkinson, Tris-(2-pyridyl) phosphine complexes of ruthenium(Ⅱ) and rhodium(I)-hydroformylation of hex-1-ene by rhodium complexes, J. Chem. Soc. Dalton Trans. (1980) 55-58.

[43] H.J.V. Barros, M.L. Ospina, E. Arguello, W.R. Rocha, E.V. Gusevskaya, E.N. dos Santos, Rhodium catalyzed hydroformylation of beta-pinene and camphene:Effect of phosphorous ligands and reaction conditions on diastereoselectivity, J. Organomet. Chem. 671(2003) 150-157.

[44] F.H. Westheimer, S. Huang, F. Covitz, Rates and mechanisms of hydrolysis of esters of phosphorous-acid, J. Am. Chem. Soc. 110(1988) 181-185.

The influence of different monodentate P-ligand mixtures on Rh-catalyzed 1-butene hydroformylation

The influence of different monodentate P-ligand mixtures on Rh-catalyzed 1-butene hydroformylation

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