Study on 1-Octene Hydroformylation Promoted by Cetyltrihydroxyethyl Ammonium Bromide in Aqueous/Organic Biphasic Solution

doi:10.6023/A13020164

Acta Chimica Sinica ›› 2013, Vol. 71 ›› Issue (05): 844-848.DOI: 10.6023/A13020164 Previous Articles Next Articles

Article

十六烷基三羟乙基溴化铵促进1-辛烯氢甲酰化水/有机两相反应研究

苏珂, 蒋红斌, 朱德明, 付海燕, 郑学丽, 袁茂林, 李瑞祥, 陈华

四川大学化学学院有机金属络合催化研究所绿色化学与技术教育部重点实验室成都 610064

投稿日期:2013-02-01 发布日期:2013-03-21
通讯作者: 袁茂林,cdscyml@sina.com.cn E-mail:cdscyml@sina.com.cn
基金资助:
项目受四川大学青年教师科研启动基金(No. 2011SCU11084)和中国石油天然气股份有限公司石油化工研究院(No. 2011B-2606)资助.

Study on 1-Octene Hydroformylation Promoted by Cetyltrihydroxyethyl Ammonium Bromide in Aqueous/Organic Biphasic Solution

Su Ke, Jiang Hongbin, Zhu Deming, Fu Haiyan, Zheng Xueli, Yuan Maolin, Li Ruixiang, Chen Hua

Key Laboratory of Green Chemistry and Technology of the Ministry of Education, Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064

Received:2013-02-01 Published:2013-03-21
Supported by:
Project supported by Sichuan University Scientific Research Foundation for Young Teachers (No. 2011SCU11084) and Petrochemical Research Institute of China National Petroleum Corporation (No. 2011B-2606).

1. Study on 1-Octene Hydroformylation Promoted by Cetyltrihydroxyethyl Ammonium Bromide in Aqueous/Organic Biphasic Solution.PDF(1309KB)

Abstract

A persisting problem in homogenous olefin hydroformylation is the recovery and reuse of the expensive rhodium catalyst. The aqueous/organic biphasic catalysis offers a feasible way to solve the problem of separation of products from catalysts. However, owing to very low solubility of higher olefin in the aqueous phase and the higher energy barrier of olefin transfer from the organic phase to the aqueous phase, the reaction rate is extremely low. The addition of a surfactant is a practical way to accelerate long-chain alkene hydroformylation in aqueous/organic bisphasic solution. In this paper, the influence of cetyltrihydroxyethyl ammonium bromide (CTHAB) on 1-octene hydroformylation in aqueous/organic two-phase solution with HRh(CO)(TPPTS)₃ as catalyst and TPPTS [P(m-C₆H₄SO₃Na)₃] as ligand was investigated. It was confirmed that a complex formed between CTHAB and HRh(CO)(TPPTS)₂ and the complex was further led to the enrichment of the catalytically active species on the micelle surface. Compared with the traditional surfactant cetyltrimethyl ammonium bromide (CTAB), results showed that the addition of surfactant CTHAB not only accelerated the 1-octene hydroformylation but also improved the molar ratio of linear to branched aldehydes. The effects of various reaction parameters, such as concentration of surfactants, [TPPTS]/[Rh] molar ratio, pressure of syngas and recycling number of catalytic system were investigated. Under the mild conditions: [Rh]=0.8 mmol/L, [TPPTS]/[Rh]=40, [CTHAB]=4.0 mmol/L, 90 ℃, 0.5 MPa, 1.5 h, the TOF and the molar ratio of linear to branched aldehydes reached up to 497 h^-1 and 25.6, respectively. The catalyst-containing aqueous could be easily separated from organic phase and efficiently reused for seven times without evident loss of activity and regioselectivity. Meanwhile, the hydroformylation of different chain length olefins was also promoted by CTHAB.

Key words: hydroformylation, 1-octene, biphasic catalysis, water-soluble rhodium phosphine complex, surfactant, cetyltrihydroxyethyl ammonium bromide

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Su Ke, Jiang Hongbin, Zhu Deming, Fu Haiyan, Zheng Xueli, Yuan Maolin, Li Ruixiang, Chen Hua . Study on 1-Octene Hydroformylation Promoted by Cetyltrihydroxyethyl Ammonium Bromide in Aqueous/Organic Biphasic Solution[J]. Acta Chimica Sinica, 2013, 71(05): 844-848.

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[1] Kuntz, E. G. CHEMTECH 1987, 17(9), 570.
[2] Yuan, M. L.; Chen, H.; Li, R. X.; Li, Y. Z.; Li, X. J. Appl. Catal. 2003, 251, 181.
[3] Tilloy, S.; Genin, E.; Hapiot, F.; Landy, D.; Fourmentin, S.; Genet, J. P.; Michelet, V.; Monflier, E. Adv. Synth. Catal. 2006, 348, 1547.
[4] Chen, H.; Li, Y. Z.; Chen, J. R.; Cheng, P. M.; He, Y. E.; Li, X. J. J. Mol. Catal. A: Chem. 1999, 149, 1.
[5] Naziruddin, A. R.; Hepp, A.; Pape, T.; Hahn, F. E. Organometallics 2011, 30, 5859.
[6] Fu, H. Y.; Yuan, M. L.; Chen, H.; Li, R. X.; Li, X. J. Chin. J. Catal. 2010, 31, 251. (付海燕, 袁茂林, 陈华, 李瑞祥, 李贤均, 催化学报, 2010, 31, 251.)
[7] Lü, S. F.; Huang, F. X.; Hu, B.; Qin, Y. H.; Zhang, X. Y. Speciality Petrochem. 2008, 25(6), 49. (吕顺风, 黄凤兴, 胡波, 秦燕璜, 张秀英, 精细石油化工, 2008, 25(6), 49.)
[8] Ding, H.; Hanson, B. E.; Glass, T. E. Inorg. Chim. Acta 1995, 229, 329.
[9] Giménez-Pedrós, M. D.; Aghmiz, A.; Claver, C.; Masdeu-Bultó, A. M.; Sinou, D. J. Mol. Catal. A: Chem. 2003, 200, 157.
[10] Chaudhari, R. V.; Bhanage, B. M.; Deshpande, R. M.; Delmas, H. Nature 1995, 373, 501.
[11] Kalck, P.; Dessoudeix, M.; Schwarz, S. J. Mol. Catal. A: Chem. 1999, 143, 41.
[12] Jin, Z. L.; Zheng, X. L.; Fell, B. J. Mol. Catal. A: Chem. 1997, 116(2), 55.
[13] Peng, Q. R.; Liao, X. L.; Yuan, Y. Z. Catal. Commun. 2004, 5, 447.
[14] Goedheijt, M. S.; Hanson, B. E.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2000, 122, 1650.
[15] Liu, C.; Jiang, J. Y.; Wang, Y. H.; Cheng, F.; Jin, Z. L. J. Mol. Catal. A: Chem. 2003, 198, 23.
[16] Ji, Z. J.; Jiang, J. Y.; Wang, Y. H. Chin. Chem. Lett. 2010, 21, 515.
[17] Sueur, B.; Leclercq, L.; Sauthier, M.; Castanet, Y.; Mortreux, A.; Bricout, H.; Tilloy, S.; Monflier, E. Chem. Eur. J. 2005, 11(21), 6228.
[18] Patrigeon, J.; Hapiot, F.; Canipelle, M.; Menuel, S.; Monflier, E. Organometallics 2010, 29, 6668.
[19] Klosin, J.; Landis, C. R. Acc. Chem. Res. 2007, 40, 1251.
[20] Sieffert, N.; Wipff, G. J. Phys. Chem. B 2006, 110(9), 4125.
[21] Leclercq, L.; Schmitzer, A. R. Organometallics 2010, 29, 3442.
[22] Leclercq, L.; Hapiot, F.; Tilloy, S.; Ramkisoensing, K.; Reek, J. N. H.; van Leeuwen, P. W. N. M.; Monflier, E. Organometallics 2005, 24, 2070.
[23] Fu, H. Y.; Wang, X.; Yuan, M. L.; Li, Y. Z.; Chen, H.; He, Y. E.; Li, X. J. Chem. Res. Appl. 2003, 15, 332. (付海燕, 王霞, 袁茂林, 黎耀忠, 陈华, 何玉萼, 李贤均, 化学研究与应用, 2003, 15, 332.)
[24] Miyagawa, C. C.; Kupka, J.; Schumpe, A. J. Mol. Catal. A: Chem. 2005, 234, 9.
[25] Chen, H.; Li, Y. Z.; Chen, J. R.; Cheng, P. M.; Li, X. J. Catal. Today 2002, 74, 131.
[26] Li, M.; Li, Y.; Chen, H.; He, Y. E.; Li, X. J. J. Mol. Catal. A: Chem. 2003, 194, 13.
[27] Yuan, M. Y.; Chen, H.; Li, R. X.; Li, Y. Z.; Li, X. J. Catal. Lett. 2003, 94, 15.
[28] Li, M.; Xu, B.; Chen, H.; He, Y. E.; Huang, X. Y.; Li, L. B.; Li, Y. Z.; Li, X. J. Chem. J. Chin. Univ. 2004, 25(4), 717. (李敏, 徐斌, 陈华, 何玉萼, 黄雪原, 李丽波, 黎耀忠, 李贤均, 高等学校化学学报, 2004, 25(4), 717.)
[29] Chen, H.; Li, Y.; Chen, J.; Cheng, P.; He, Y.; Li, X. J. J. Mol. Catal. A: Chem. 1999, 149, 1.
[30] Fu, H. Y.; Li, M.; Chen, H.; Li, X. J. J. Mol. Catal. A: Chem. 2006, 259, 156.
[31] Fu, H. Y.; Li, M.; Mao, H.; Lin, Q.; Yuan, M. L.; Li, X. J.; Chen, H. Catal. Commun. 2008, 9, 1539.
[32] Evan, D.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1968, 3133.
[33] Wu, J. C.; Yuan, G.; Zhou, Q. Z. Petrochem. Technol. 1991, 20, 79. (吴己丑, 袁刚, 周启昭, 石油化工, 1991, 20, 79.)
[34] Chen, H.; Li, X. J.; Liu, H. C.; Li, Y. Z. CN 1179428, 1999. (陈华, 李贤均, 刘海超, 黎耀忠, CN 1179428, 1999).
[35] Li, X. J.; Chen, H.; Li, Y. Z.; Liu, H. C. CN 1179429, 1999. (李贤均, 陈华, 黎耀忠, 刘海超, CN 1179429, 1999).

十六烷基三羟乙基溴化铵促进1-辛烯氢甲酰化水/有机两相反应研究

Study on 1-Octene Hydroformylation Promoted by Cetyltrihydroxyethyl Ammonium Bromide in Aqueous/Organic Biphasic Solution

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