Citation: ZHANG Xiao-Ya, ZHENG Cong-Ye, ZHENG Xue-Li, FU Hai-Yan, YUAN Mao-Lin, LI Rui-Xiang, CHEN Hua. Preparation of Silica-Bonded Phosphine and Its Influence on 1-Octene Hydroformylation Catalyzed by Rhodium Complex[J]. Acta Physico-Chimica Sinica, ;2015, 31(4): 738-742. doi: 10.3866/PKU.WHXB201502063 shu

Preparation of Silica-Bonded Phosphine and Its Influence on 1-Octene Hydroformylation Catalyzed by Rhodium Complex

  • Received Date: 15 December 2014
    Available Online: 6 February 2015

    Fund Project: 中国石油天然气股份有限公司石油化工研究所(2011B-2606) (2011B-2606)四川大学青年教师科研启动基金(2011SCU11084)资助 (2011SCU11084)

  • Using silica as a support, 2-(diphenylphosphino)ethyltriethoxysilane (DPPES) was anchored on silica surface by a grafting method to produce a bonded phosphine (denoted as SiO2(PPh2)), which displays excellent performance. The supported SiO2(PPh2)/Rh catalyst was formed in situ in 1-octene hydroformylation with SiO2(PPh2) as ligand and Rh(acac)(CO)2 as precursor (acac: acetylacetone). SiO2(PPh2) and SiO2(PPh2)/ Rh were characterized by Fourier transform infrared (FTIR) spectroscopy. The effects of the ratio of phosphine to rhodium ([P]/[Rh]) and reaction temperature on 1-octene hydroformylation were investigated. Results show that an increase of the ratio of phosphine to rhodium can greatly improve the selectivity for aldehydes and decrease the rhodium leaching in organic phase. Under the moderate conditions: [P]/[Rh]=12, 363 K, 2 MPa, and 1.5 h, the conversion of 1-octene and the selectivity for aldehydes were 98.4% and 95.3%, respectively. The catalytic activity could compare with homogeneous catalysis with DPPES or triphenylphosphine (TPP) as ligand. The reaction activity was clearly unchanged after the SiO2(PPh2)/Rh catalyst was reused four times, with the conversion of 1-octene remaining at 97.0%, the rhodium content leaching in organic phase detected by inductively coupled plasma-atomic emission spectroscopy (ICP-AES) was less than 0.1%.

  • 加载中
    1. [1]

      (1) Van Leeuwen, P.W. N. M.; Claver, C. Rhodium Catalyzed Hydroformylation; Kluwer Academic Publisher: Dordrecht, 2002; pp 1-8.

    2. [2]

      (2) Beller, M.; Cornils, B. J. Mol. Catal. A 1995, 104, 17. doi: 10.1016/1381-1169(95)00130-1

    3. [3]

      (3) Ungvary, F. Coord. Chem. Rev. 2004, 248, 867. doi: 10.1016/j.ccr.2003.02.001

    4. [4]

      (4) Jiang, H. Y.; Wu, Z. F.; Chen, H. Acta Phys. -Chim. Sin. 2013, 29 (7), 1572. [蒋和雁, 吴志峰, 陈华. 物理化学学报, 2013, 29 (7), 1572.] doi: 10.3866/PKU.WHXB201304243

    5. [5]

      (5) Zhang, L.; Hu, B.; Chen, H.; Li, X. J.; Li, R. X. Acta Phys. -Chim. Sin. 2010, 26 (9), 2422. [张磊, 胡博, 陈华, 李贤均, 李瑞祥. 物理化学学报, 2010, 26 (9), 2422.] doi: 10.3866/PKU.WHXB20100901

    6. [6]

      (6) Han, D. F.; Li, X. H.; Zhang, H. D.; Liu, Z. M.; Li, J.; Li, C. J. Catal. 2006, 243, 318. doi: 10.1016/j.jcat.2006.08.003

    7. [7]

      (7) Alini, S.; Bottino, A.; Capannelli, G.; Comite, A.; Paganelli, S. Appl. Catal. A 2005, 292, 105. doi: 10.1016/j.apcata.2005.05.048

    8. [8]

      (8) Bourque, S. C.; Alper, H.; Manzer, L. E.; Arya, P. J. Am. Chem. Soc. 2000, 122 (5), 956. doi: 10.1021/ja993196f

    9. [9]

      (9) Li, P.; Thitsartarn, W.; Kawi, S. Ind. Eng. Chem. Res. 2009, 48 (4), 1824. doi: 10.1021/ie800715k

    10. [10]

      (10) Bando, K. K.; Asakura, K.; Arakawa, H.; Isobe, K.; Iwasawa, Y. J. Phys. Chem. 1996, 100 (32), 13636. doi: 10.1021/jp953124k

    11. [11]

      (11) Kontksnen, M. L.; Tuikka, M.; Kinnunen, N. M.; Suvanto, S.; Haukka, M. Catalysis 2013, 3, 324. doi: 10.3390/catal3010324

    12. [12]

      (12) Mukhopadhyay, K.; Chaudhari, R. V. J. Catal. 2003, 213, 73. doi: 10.1016/S0021-9517(02)00020-9

    13. [13]

      (13) Li, B. T.; Li, X. H.; Asami, K.; Fujimoto, K. Energy Fuels 2003, 17 (4), 810. doi: 10.1021/ef0202440

    14. [14]

      (14) Reynhardt, J. P. K.; Yang, Y.; Sayari, A.; Alper, H. Chem. Mater. 2004, 16 (21), 4095. doi: 10.1021/cm0493142

    15. [15]

      (15) Abu-Reziq, R.; Alper, H.; Wang, D. S.; Post, M. L. J. Am. Chem. Soc. 2006, 128 (15), 5279. doi: 10.1021/ja060140u

    16. [16]

      (16) Huang, L.; Kawi, S. Catal. Lett. 2003, 90 (3-4), 165.

    17. [17]

      (17) Bourque, S. C.; Maltais, F.; Xiao, W. J.; Tardif, O.; Alper, H.; Arya, P.; Manzer, L. E. J. Am. Chem. Soc. 1999, 121 (13), 3035. doi: 10.1021/ja983764b

    18. [18]

      (18) Ichikawa, M. J. Catal. 1979, 59, 67. doi: 10.1016/S0021-9517 (79)80046-9

    19. [19]

      (19) Xu, J. Q.; Chu, W.; Luo, R. Z. J. Sichuan Univ. (Engin. Sci. Edit.) 2007, 39 (5), 70. [许俊强, 储伟, 罗仁忠. 四川大学学报(工程科学版), 2007, 39 (5), 70.]

    20. [20]

      (20) Li, P.; Kawi, S. Catal. Today 2008, 131, 61. doi: 10.1016/j.cattod.2007.10.090

    21. [21]

      (21) Zhou, W.; He, D. H. Catal. Lett. 2009, 127, 437. doi: 10.1007/s10562-008-9734-8

    22. [22]

      (22) Peng, Q. R.; Yang, Y.; Yuan, Y. Z. J. Mol. Catal. A: Chem. 2004, 219, 175. doi: 10.1016/j.molcata.2004.05.003

    23. [23]

      (23) Bonati, F.; Wilkinson, G. J. Chem. Soc. 1964, 3156.

    24. [24]

      (24) Zhao, L. Y.; Wang, S. C.; Wu, Y.; Hou, Q. F.; Wang, Y.; Jiang, S. M. J. Phys. Chem. 2007, 111 (49), 18387.

    25. [25]

      (25) Yang, Y.; Peng, Q. R.; Yuan, Y. Z. Chin. J. Catal. 2004, 25 (5), 421. [杨勇, 彭庆荣, 袁友珠. 催化学报, 2004, 25 (5), 421.]

    26. [26]

      (26) Liu, S. M.; Lin, Z. Y.; Yin, Y. Q. Acta Phys. -Chim. Sin. 1992, 8 (4), 530. [刘省明, 林政炎, 殷元骐. 物理化学学报, 1992, 8 (4), 530.] doi: 10.3866/PKU.WHXB19920421

    27. [27]

      (27) Busca, G. Catal. Today 1998, 41, 191. doi: 10.1016/S0920-5861 (98)00049-2

    28. [28]

      (28) Evans, D.; Osborn, J. A.; Wilkinson, G. J. Chem. Soc. A 1968, 3133.


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