Chinese Journal of Organic Chemistry >
Progress in Platinum Catalysts Supported by Inorganic Carriers for Hydrosilylation
Received date: 2015-09-21
Revised date: 2015-12-20
Online published: 2016-01-04
Supported by
Project supported by the National Natural Science Foundation of China (No. 21276121) and the Natural Science Foundation of Jiangxi Province (No. 20122BAB203021).
Hydrosilylation catalyzed by transition metals or their complexes is one of the most important ways to synthesize organosilicones, and platinum catalysts are widely used. Inorganic carriers supported platinum catalysts not only can avoid the disadvantages of homogeneous catalysts, such as corroding reactor, pain platinum recovery and low reaction selectivity, but also can be available for sequential reactions due to the good mechanical strength and stability in reaction medium. A lot of literatures relating to platinum catalysts supported by inorganic carriers for hydrosilylation have been published. The platinum compounds have been supported by carbon carriers, silica, metallic oxide, molecular sieve or other inorganic carriers via direct load method or complexation between platinum and vinyl, phosphino, amino, arsino or mercapto functional group modified on the surface of the carriers. The research progresses in preparation, structure and properties of inorganic carriers supported platinum catalysts for hydrosilylation during recent 15 years are summarized with the description of their development trend.
Key words: inorganic carrier; platinum; supported catalyst; hydrosilylation; progress
Xiao Jianjun , Qiu Zumin , He Weijuan , Du Chengcheng , Zhou Wei . Progress in Platinum Catalysts Supported by Inorganic Carriers for Hydrosilylation[J]. Chinese Journal of Organic Chemistry, 2016 , 36(5) : 987 -999 . DOI: 10.6023/cjoc201509028
[1] Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis, Vol. 8, Eds.: Trost, B. M.; Fleming, I., Pergamon, New York, 1991, pp. 763~792.
[2] Marciniec, B. Comprehensive Handbook on Hydrosilylation, Pergamon, New York, 1992, pp. 3~7.
[3] Lai, G. Q.; Xing, S. M. Synthesis Process and Application of Organic Silicon Products, 2nd ed, Chemical Industry Press, Beijing, 2010, pp. 24~159 (in Chinese).
(来国桥, 幸松民, 有机硅产品合成工艺及应用, 第二版, 化学工业出版社, 北京, 2010, pp. 24~159.)
[4] Long, Q.; Zhou, D. L.; Zhang, X.; Wei, D. J.; Liu, S. J.; Chen, D. N. Chin. J. Inorg. Chem. 2013, 29, 948 (in Chinese).
(龙沁, 周大利, 张翔, 卫冬娟, 柳淑婧, 陈冬宁, 无机化学学报, 2013, 29, 948.)
[5] Sommer, L. H.; Pietrusza, E. W.; Whitmore, F. C. J. Am. Chem. Soc. 1947, 69, 188.
[6] Nesmeyanov, A. N.; Freidlina, R. K.; Chukovskaya, E. C.; Petrova, R. G.; Belyavsky, A. B. Tetrahedron 1962, 17, 61.
[7] Brunner, H.; Eder, R.; Hammer, B.; Klement, U. J. Organomet. Chem. 1990, 394, 555.
[8] Zhou, S.; Fleischer, S.; Junge, K.; Das, S.; Addis, D.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 8121.
[9]
[9] Enthaler, S. Chem. Cat. Chem. 2011, 3, 666.
[10]
[10] Wang, Z. L.; Ding, H. J.; Yang, Y. X.; Huan, W. W.; Yuan, H. M.; Li, B. W.; Liu, X. N. Chin. J. Inorg. Chem. 2011, 27, 1033 (in Chinese).
(王兆伦, 丁海军, 杨宇翔, 郇伟伟, 袁宏明, 李必武, 刘向农, 无机化学学报, 2011, 27, 1033.)
[11] Ojima, I. In Organic Silicon Compounds, Vol. 1~2, Eds.: Patai, S.; Rappoport, Z., John Wiley and Sons, New York, 1989, pp. 1479~1526.
[12] Li, R.; Liu, B. L.; Zhang, B. T.; Chen, X. N.; Zhang, F.; Wang, G. Y. Chin. J. Synth. Chem. 2010, 48 (in Chinese).
(李茹, 刘白玲, 张保坦, 陈修宁, 张帆, 王公应, 合成化学, 2010, 48.)
[13] Bai, Y.; Peng, J. J.; Li, J. Y.; Lai, G. Q.; Li, X. N. Prog. Chem. 2011, 23, 2466 (in Chinese).
(白赢, 彭家建, 厉嘉云, 来国桥, 李小年, 化学进展, 2011, 23, 2466.)
[14] Speier, J. L.; Webster, J. A.; Barnes, G. H. J. Am. Chem. Soc. 1957, 79, 974.
[15] Ma, G. W.; Weng, J. X.; Fan, H. Bull. Sci. Technol. 2012, 28, 140 (in Chinese).
(马国维, 翁剑秀, 范宏, 科技通报, 2012, 28, 140.)
[16] Karstedt, B. US 3775452, 1973 [Chem. Abstr. 1969, 71, 91641].
[17] Dioumaev, V. K.; Bullock, R. M. Nature 2000, 424, 530.
[18] Markó, I. E.; Stérin, S.; Buisine, O.; Mignani, G.; Branlard, P.; Tinant, B.; Declercq, J. Science 2002, 298, 204.
[19] Pagliaro, M.; Ciriminna, R.; Pandarus, V.; Béland, F. Eur. J. Org. Chem. 2013, 2013, 6227.
[20] Jiménez, R.; Martínez-Rosales, J. M.; Cervantes, J. Can. J. Chem. 2003, 81, 1370.
[21] Caporusso, A. M.; Aronica, L. A.; Schiavi, E.; Martra, G.; Vitulli, G.; Salvadori, P. J. Organomet. Chem. 2005, 690, 1063.
[22] Hamasaka, G.; Kawamorita, S.; Ochida, A.; Akiyama, R.; Hara, K.; Fukuoka, A.; Asakura, K.; Chun, W. J.; Ohmiya, H.; Sawamura, M. Organometallics 2008, 27, 6495.
[23] Shih, H.; Williams, D.; Mack, N. H.; Wang, H. Macromolecules 2008, 42, 14.
[24] Bai, Y.; Peng, J. J.; Hu, Y. Q.; Li, J. Y.; Lai, G. Q. J. Fluorine Chem. 2011, 132, 123.
[25] Bandari, R.; Buchmeiser, M. R. Catal. Sci. Technol. 2012, 2, 220.
[26] Yermakov, Y. I.; Kuznetsov, B. N.; Zakharov, V. A. Catalysis by Supported Complexes, Vol. 8, Elsevier, Amsterdam, 1981, pp. 1~58.
[27] Jiao, J. L.; Huang, L. J.; Teng, D. W. Chem. Bioeng. 2010, 27, 4 (in Chinese).
(焦建丽, 黄龙江, 滕大为, 化学与生物工程, 2010, 27, 4.)
[28] Jia, Y.; Xu, G. G.; Wang, X. J. Application of Lightweight Carbon Materials, National Defence Industry Press, Beijing, 2013, pp. 1~10 (in Chinese).
(贾瑛, 许国根, 王煊军, 轻质碳材料的应用, 国防工业出版社, 北京, 2013, pp. 1~10.)
[29] Yang, Y. Engineering Technology and Equipment of Flue Gas Desulfurization and Denitration, Chemical Industry Press, Beijing, 2013, pp. 409~411 (in Chinese).
(杨颺, 烟气脱硫脱硝净化工程技术与设备, 化学工业出版社, 北京, 2013, pp. 409~411.)
[30] Li, Z.; Zhu, Q. F.; Wang, R. Y.; Niu, Y. Y.; Zheng, H. Y. Chin. J. Inorg. Chem. 2011, 27, 718 (in Chinese).
(李忠, 朱琼芳, 王瑞玉, 牛燕燕, 郑华艳, 无机化学学报, 2011, 27, 718.)
[31] Chauhan, M.; Hauck, B. J.; Keller, L. P.; Boudjouk, P. J. Organomet. Chem. 2002, 645, 1.
[32] Marciniec, B.; Maciejewski, H.; Duczmal, W.; Fiedorow, R.; Kityński, D. Appl. Organomet. Chem. 2003, 17, 127.
[33] Bai, Y.; Peng, J. J.; Li, J. Y.; Hu, Y. G.; Qiu, H. Y.; Jiang, J. X.; Lai, G. Q. Silicone Mater. 2008, 22, 194 (in Chinese).
(白赢, 彭家建, 厉嘉云, 胡应乾, 邱化玉, 蒋剑雄, 来国桥, 有机硅材料, 2008, 22, 194.)
[34] Yang, H.; Bai, Y.; Peng, J. J.; Li, J. Y.; Liu, S.; Lai, G. Q. Chem. Reag. 2012, 34, 694 (in Chinese).
(杨虎, 白赢, 彭家建, 厉嘉云, 刘帅, 来国桥, 化学试剂, 2012, 34, 694.)
[35] Liu, Y. R. Carbon Materials for Supercapacitor Application, National Defence Industry Press, Beijing, 2013, pp. 211~237 (in Chinese).
(刘玉荣, 碳材料在超级电容器中的应用, 国防工业出版社, 北京, 2013, pp. 211~237.)
[36] Dongil, A. B.; Bachiller-Baeza, B.; Guerrero-Ruiz, A.; Rodríguez-Ramos, I. J. Catal. 2011, 282, 299.
[37] Dongil, A. B.; Bachiller-Baeza, B.; Guerrero-Ruiz, A.; Rodríguez-Ramos, I. Catal. Commun. 2012, 26, 149.
[38] Hu, Z.; Liu, C. B. J. Polym. Res. 2013, 20, 1.
[39] Zhao, Y. F.; Zhang, H. Y.; Huang, C. L.; Chen, S.; Yu, B.; Xu, J. L.; Liu, Z. M. Sci. China Chem. 2013, 56, 203.
[40] Mungse, H. P.; Verma, S.; Kumar, N.; Sain, B.; Khatri, O. P. J. Mater. Chem. 2012, 22, 5427.
[41] Li, Z. F.; Wu, S. J.; Ding, H.; Zheng, D. F.; Hu, J.; Wang, X.; Huo, Q.; Guan, J.; Kan, Q. New J. Chem. 2013, 37, 1561.
[42] Rao, F. Y.; Deng, S. J.; Chen, C.; Zhang, N. Catal. Commun. 2014, 46, 1.
[43] Deng, S. J.; Zheng, Q.; Rao, F. Y.; Lin, L. Z.; Zhang, N. Chin. J. Inorg. Chem. 2015, 31, 1085 (in Chinese).
(邓圣军, 郑强, 饶福原, 林凌志, 张宁, 无机化学学报, 2015, 31, 1085.)
[44] Liao, X. N.; Xiao, J. H.; Li, F. Y.; Hu, C. Y.; Hua, L. New Chem. Mater. 2006, 34, 40 (in Chinese).
(廖晓宁, 肖军华, 李凤仪, 胡长元, 华丽, 化工新型材料, 2006, 34, 40.)
[45] Funck, A.; Kaminsky, W. Compos. Sci. Technol. 2007, 67, 906.
[46] Deng, D. H.; Yu, L.; Chen, X. Q.; Wang, G.; Jin, L.; Pan, X.; Deng, J.; Sun, G.; Bao, X. Angew. Chem., Int. Ed. 2013, 52, 371.
[47] Li, X. T.; Zang, P. Y.; Ye, Q. M.; Geng, J.; Wang, X. Z.; Wang, Y. N.; Hu, Z. Chin. J. Inorg. Chem. 2011, 27, 1550 (in Chinese).
(李雪亭, 臧鹏远, 叶秋明, 耿皎, 王喜章, 王秧年, 胡征, 无机化学学报, 2011, 27, 1550.)
[48] Dai, Y. F.; Li, F. Y.; Xiao, B. Modern Chem. Ind. 2005, 25, 31 (in Chinese).
(戴延凤, 李凤仪, 萧斌, 现代化工, 2005, 25, 31.)
[49] Zhao, J. B.; Sun, Y. A.; Liu, Y. F.; Chen, C. F.; Xie, B.; Zheng, X. J. China Surfactant Deterg. Cosmet. 2010, 40, 427 (in Chinese).
(赵建波, 孙雨安, 刘应凡, 陈长福, 谢冰, 郑先君, 日用化学工业, 2010, 40, 427.)
[50] Zarei, A. Tetrahedron Lett. 2012, 53, 5176.
[51] Chandrachood, P.; Gadkari, T.; Deshpande, N.; Kashalkar, R. J. Iran. Chem. Soc. 2012, 9, 47-51.
[52] Zupp, L. R.; Campanella, V. L.; Rudzinski, D. M.; Beland, F.; Priefer, R. Tetrahedron Lett. 2012, 53, 5343.
[53] Mahmoodi, N. O.; Heirati, S. Z. D.; Ekhlasi-Kazaj, K. J. Iran. Chem. Soc. 2012, 9, 521.
[54] Bauer, J. C.; Veith, G. M.; Allard, L. F.; Oyola, Y.; Overbury, S. H.; Dai, S. ACS Catal. 2012, 2, 2537.
[55] Okamoto, M.; Kiya, H.; Yamashita, H.; Suzuki, E. Chem. Commun. 2002, 1634.
[56] Okamoto, M.; Kiya, H.; Matsumura, A.; Suzuki, E. Catal. Lett. 2008, 123, 72.
[57] Afanasev, D. S.; Yakovina, O. A.; Kuznetsova, N. I.; Lisitsyn, A. S. Catal. Commun. 2012, 22, 43.
[58] Franco, C. A.; Montoya, T.; Nassar, N. N.; Pereira-Almao, P.; Cortés, F. B. Energy Fuels 2013, 27, 7336.
[59] Li, J.; Yang, C. H.; Zhang, L.; Ma, T. L. J. Organomet. Chem. 2011, 696, 1845.
[60] Liu, G.; Huang, B.; Cai, M. Z. React. Funct. Polym. 2007, 67, 294.
[61] Zhu, H. F. Preparation and Application Technology of Catalyst Carriers, Petroleum Industry Press, Beijing, 2002, pp. 614~626 (in Chinese).
(朱洪法, 催化剂载体制备及应用技术, 石油工业出版社, 北京, 2002, pp. 614~626.)
[62] Huang, S.; Ganesan, P.; Popov, B. N. Appl. Catal. B-Environ. 2011, 102, 71.
[63] Djeddi, A.; Fechete, I.; Garin, F. Top. Catal. 2012, 55, 700.
[64] Su, R.; Tiruvalam, R.; Logsdail, A. J.; He, Q.; Downing, C. A.; Jensen, M. T.; Dimitratos, N.; Kesavan, L.; Wells, P. P.; Bechstein, R. ACS Nano 2014, 8, 3490.
[65] Alonso, F.; Buitrago, R.; Moglie, Y.; Ruiz-Martínez, J.;Sepúlveda-Escribano, A.; Yus, M. J. Organomet. Chem. 2011, 696, 368.
[66] Alonso, F.; Buitrago, R.; Moglie, Y.; Sepúlveda-Escribano, A.; Yus, M. Organometallics 2012, 31, 2336.
[67] Selvamani, T.; Yagyu, T.; Kawasaki, S.; Mukhopadhyay, I. Catal. Commun. 2010, 11, 537.
[68] Zhang, Y. F.; Ma, M. Z.; Zhang, X. Y.; Wang, B. A.; Liu, R. P. J. Alloys Compd. 2014, 590, 373.
[69] Kalu?a, L.; Gulková, D.; Vít, Z.; Zdra?il, M. Appl. Catal. B-Environ. 2015, 162, 430.
[70] Yang, X. L.; Xia, C. G.; Tang, L. P.; Xiong, X. M.; Mu, X. Y.; Hu, B. Chin. J. Inorg. Chem. 2011, 27, 1541 (in Chinese).
(杨晓龙, 夏春谷, 唐立平, 熊绪茂, 慕新元, 胡斌, 无机化学学报, 2011, 27, 1541.)
[71] Jiménez, R.; López, J. M.; Cervantes, J. Can. J. Chem. 2000, 78, 1491.
[72] Ramírez-Oliva, E.; Hernández, A.; Martínez-Rosales, J. M. ARKIVOC 2006, 126.
[73] Xu, H. J.; Wan, X.; Shen, Y. Y.; Xu, S.; Feng, Y. S. Org. Lett. 2012, 14, 1210.
[74] Xu, L.; Wang, J. Environ. Sci. Technol. 2012, 46, 10145.
[75] Baykal, A.; Karaoglu, E.; Sözeri, H.; Uysal, E.; Toprak, M. S. J. Supercond. Novel Magn. 2013, 26, 165.
[76] Cano, R.; Yus, M.; Ramón, D. J. ACS Catal. 2012, 2, 1070.
[77] Huang, Z.; Shi, Y.; Wen, R.; Guo, Y. H.; Su, J. F.; Matsuura, T. Sep. Purif. Technol. 2006, 51, 126.
[78] Chen, F.; Li, Y.; Cai, W. D.; Zhang, J. L. J. Hazard. Mater. 2010, 177, 743.
[79] Dai, Y. F.; Ru, X.; Li, F. Y. New Chem. Mater. 2005, 33, 57 (in Chinese).
(戴延凤, 茹翔, 李凤仪, 化工新型材料, 2005, 33, 57.)
[80] Deng, F. J.; Xu, S. H.; Wen, Y. Q.; Li, W. F.; Li, F. Y. Chem. Ind. Eng. Prog. 2008, 27, 112 (in Chinese).
(邓锋杰, 徐少华, 温远庆, 李卫凡, 李凤仪, 化工进展, 2008, 27, 112.)
[81] Mastalir, A.; Rác, B.; Király, Z.; Molnár, Á. J. Mol. Catal. A: Chem. 2007, 264, 170.
[82] Duan, X. Z.; Qian, G.; Zhou, X. G.; Chen, D.; Yuan, W. K. Chem. Eng. J. 2012, 207, 103.
[83] Wang, N.; Yu, X. P.; Wang, Y.; Chu, W.; Liu, M. Catal. Today. 2013, 212, 98.
[84] Lovell, E.; Jiang, Y.; Scott, J.; Wang, F.; Suhardja, Y.; Chen, M.; Huang, J.; Amal, R. Appl. Catal. A-Gen. 2014, 473, 51.
[85] Guan, Q. X.; Wan, F. F.; Han, F.; Liu, Z. H.; Li, W. Catal. Today 2016, 259, 467.
[86] Wu, H. Y.; Zhang, X. L.; Chen, X.; Chen, Y.; Zheng, X. C. J. Solid State Chem. 2014, 211, 51.
[87] Yan, X. W.; Han, X. W.; Cao, Y.; Wei, Y. L.; Zhu, J. H. Chin. J. Inorg. Chem. 2002, 18, 1101 (in Chinese).
(颜学武, 韩小伟, 曹毅, 魏一伦, 朱建华, 无机化学学报, 2002, 18, 1101.)
[88] Zhang, H. A.; Liu, J. Q.; Cheng, S. J.; Cai, M. Z. J. Chem. Res. 2012, 36, 241.
[89] Hu, R. H.; Zha, L. F.; Cai, M. Z. Catal. Commun. 2010, 11, 563.
[90] Zha, L. F.; Hao, W. Y.; Cai, M. Z. J. Chem. Res. 2010, 34, 648.
[91] Ye, Z.; Shi, H.; Shen, H. Phosphorus Sulfur. 2015, 190, 1621.
[92] Yang, H.; Chang, S. F.; Bai, Y.; Peng, J. J.; Li, J. Y.; Lai, G. Q. J. Hangzhou Normal Univ.
(Nat. Sci. Ed.) 2012, 11, 217 (in Chinese).
(杨虎, 张淑芳, 白赢, 彭家建, 厉嘉云, 来国桥, 杭州师范大学学报(自然科学版), 2012, 11, 217.)
[93] Ma, J.; Xue, J. Q. Theory and Application of Industrial Catalysis, Metallurgical Industry Press, Beijing, 2013, pp. 120~144 (in Chinese).
(马晶, 薛娟琴, 工业催化原理及应用,冶金工业出版社, 北京, 2013, pp. 120~144.)
[94] Deng, Y.; Bai, Y.; Li, L. J. Hangzhou Normal Univ.
(Nat. Sci. Ed.) 2009, 8, 367 (in Chinese).
(邓元, 白赢, 李丽, 杭州师范大学学报(自然科学版), 2009, 8, 367.)
[95] Li, J. Ph.D. Dissertation, Harbin Institute of Technology, Harbin, 2011 (in Chinese).
(李季, 博士论文, 哈尔滨工业大学, 哈尔滨, 2011.)
[96] Yang, H. T. Ph.D. Dissertation, Zhejiang University, Hangzhou, 2007 (in Chinese).
(羊海棠, 博士论文, 浙江大学, 杭州, 2007.)
[97] Miao, Q. J.; Fang, Z. P.; Cai, G. P. Catal. Commun. 2003, 4, 637.
[98] Fang, Z. P.; Yang, H. T.; Miao, Q. J.; Cai, G. P. Chin. Chem. Lett. 2006, 17, 1155.
[99] Yang, H. T.; Fang, Z. P.; Fu, X. Y.; Tong, L. F. Chin. J. Catal. 2007, 28, 947.
[100] Yang, H. T.; Fang, Z. P.; Fu, X. Y.; Tong, L. F. Catal. Commun. 2008, 9, 1092.
[101] Du, M. L. Ph.D. Dissertation, South China University of Technology, Guangzhou, 2007 (in Chinese).
(杜明亮, 博士论文, 华南理工大学, 广州, 2007.)
[102] Ma, Z.; Wang, J. Y.; Gao, X.; Ding, T.; Qin, Y. N. Prog. Chem. 2012, 24, 275 (in Chinese).
(马智, 王金叶, 高祥, 丁彤, 秦永宁, 化学进展, 2012, 24, 275.)
[103] Wang, J.; Yuan, X. Y.; Huo, W. J.; Cheng, X. J.; Zhang, A. Q.; Zhang, D. H. Petrochem. Technol. 2011, 40, 949 (in Chinese).
(王晶, 袁晓焉, 火文君, 程新建, 张爱清, 张道洪, 石油化工, 2011, 40, 949.)
[104] Liang, E. B.; Wang, J.; Zhang, A. Q.; Zhang, D. H. Adhesion 2012, 38 (in Chinese).
(梁恩宾, 王晶, 张爱清, 张道洪, 粘接, 2012, 38.)
[105] Zhang, D. H.; Huo, W. J.; Wang, J.; Li, T. C.; Cheng, X. J.; Li, J. L.; Zhang, A. Q. J. Appl. Polym. Sci. 2012, 126, 1580.
/
〈 |
|
〉 |