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化学进展 2008, Vol. 20 Issue (0708): 1021-1031 前一篇   后一篇

• 综述与评论 •

多相催化剂上烯烃交叉歧化反应*

李新 张维萍** 李秀杰 刘盛林   

  1. （中国科学院大连化学物理研究所 催化国家重点实验室 大连 116023）
  • 收稿日期:2007-09-12 修回日期:2007-10-21 出版日期:2008-08-24 发布日期:2008-08-24
  • 通讯作者: 张维萍
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Heterogeneous Catalysts for Olefin Cross-Metathesis

Li Xin; Zhang Weiping**; Li Xiujie; Liu Shenglin   

  1. (State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China)
  • Received:2007-09-12 Revised:2007-10-21 Online:2008-08-24 Published:2008-08-24
  • Contact: Zhang Weiping
烯烃歧化反应广泛用于石油化工和有机合成领域。本文介绍了常用于烯烃交叉歧化反应的多相催化剂，如负载型Re、Mo、W催化剂及其特点，影响催化剂活性的因素，如金属价态、结构、分散度、载体性质及助剂影响等，探讨了烯烃歧化反应的机理及其可能的失活途径。
关键词： 烯烃交叉歧化反应, 多相催化剂, 机理, 失活
Olefin metathesis has been widely used in the fields of petrochemical industry and organic synthesis. It can be classified as ring-opening metathesis, ring-opening metathesis polymerization, ring-closing metathesis, cross-metathesis, etc. Recent developments in the heterogeneous catalysts for olefin cross-metathesis are summarized in this review. Much attention has been paid not only to the heterogeneous catalysts based on Re, Mo and W, but also to the effects that may influence the catalyst activity, such as the metal oxidation state, structure and dispersion of the active species, properties of the support and the addition of promoters, etc. The reaction mechanisms and possible deactivation routes are also discussed in detail.
Key words: olefin cross-metathesis, heterogeneous catalysts, reaction mechanisms, deactivation

中图分类号: 

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[ 1 ] 李蕊琼(Li R Q) , 傅尧( Fu Y) , 刘磊(Liu L) . 有机化学(Chin. J . Org. Chem. ) , 2004 , 24 : 1004 —1017
[ 2 ] Schrock R R , Hoveyda A H. Angew. Chem. Int . Ed. , 2003 ,42 : 4592 —4633
[ 3 ] Schrock R R. J . Mol . Catal . A , 2004 , 213 : 21 —30
[ 4 ] Trnka T M, Grubbs R H. Acc. Chem. Res. , 2001 , 34 : 18 —29
[ 5 ] Grubbs R H , Chang S. Tetrahedron , 1998 , 54 : 4413 —4450
[ 6 ] Schrock R R. Angew. Chem. Int . Ed. , 2006 , 45 : 3748 —3759
[ 7 ] Grubbs R H. Angew. Chem. Int . Ed. , 2006 , 45 : 3760 —3765
[ 8 ] Chauvin Y. Angew. Chem. Int . Ed. , 2006 , 45 : 3741 —3747
[ 9 ] Grubbs R H , Chang S. Acc. Chem. Res. , 1995 , 28 : 446 —452
[10] Mol J C. J . Mol . Catal . A , 2004 , 213 : 39 —45
[11] 白尔铮(Bai E Z) . 精细石油化工( Speciality Petrochem. Fine Petro. ) , 2001 , 2 : 24 —28
[12] 冯静(Feng J) . 化学推进剂与高分子材料( Chem. Propel .Poly. Mat . ) , 2006 , 4 : 20 —23
[13] 瞿勇(Qu Y) , 唐华荣(Tang H R) , 白尔铮(Bai E Z) 等. 石油化工(Petrochem. Technol . ) , 2002 , 31 : 1017 —1021
[14] 李影辉(Li Y H) , 增群英(Zeng Q Y) , 万书宝(Wan S B)等. 现代化工( Mod. Chem. Ind. ) , 2005 , 25 : 23 —26
[15] Banks R L , Bailey G C. Ind. Eng. Chem. Prod. Res. Dev. ,1964 , 3 : 170 —173
[16] Drǎgutan V , Balaban A T , Dimonie M. Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins , 2nd revisededition. John Wiley &Sons , Ltd. , 1985. 28 —29
[17] Crain D L. J . Catal . , 1969 , 13 : 110 —113
[18] Drǎgutan V , Balaban A T , Dimonie M. Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins , 2nd revisededition. John Wiley &Sons , Ltd. , 1985. 31
[19] Hasegawa S , Tanaka T , Kudo M, et al . Catal . Lett . , 1992 , 12 :255 —266
[20] Tanaka K, Miyahara K. J . Mol . Catal . , 1982 , 15 : 133 —146
[21] 黄声骏(Huang S J ) , 辛文杰(Xin W J ) , 刘盛林(Liu S L)等. 石油化工(Petrochem. Technol . ) , 2003 , 32 : 191 —194
[22] Liu S L , Huang S J , Xu L Y, et al . Catal . Today , 2004 , 93/95 :471 —476
[23] Huang S J , Liu S L , Xu L Y, et al . J . Mol . Catal . A , 2005 ,226 : 61 —68
[24] Mol J C. J . Mol . Catal . , 1991 , 65 : 145 —162
[25] Mol J C. Catal . Today , 1999 , 51 : 289 —299
[26] Banks R L , Banasiak D S , Hudson P S , et al . J . Mol . Catal . ,1982 , 15 : 21 —33
[27] Schalkwyk C , Spamer A , Moodley D J , et al . Appl . Catal . A ,2003 , 255 : 121 —131
[28] Basrur A G, Patwardhan S R , Vyas S N. J . Catal . , 1991 , 127 :86 —95
[29] Luckner R C , McConchie G E , Wills G B. J . Catal . , 1973 , 28 :63 —68
[30] Andreini A , Mol J C. J . Coll . Interf . Sci . , 1981 , 84 : 58 —65
[31] Pennella F , Banks R L. J . Catal . , 1973 , 31 : 304 —308
[32] Yermakov Y I. Catal . Rev. Sci . Eng. , 1976 , 13 : 77 —120
[33] Iwasawa Y, Kubo H , Hmamamura H , et al . J . Mol . Catal . ,1985 , 28 : 191 —208
[34] Iwasawa Y, Kubo H , Yamagishi M, et al . Chem. Lett . , 1980 ,1165 —1168
[35] Shelimov B N , Elev I V , Kazansky V B. J . Catal . , 1986 , 98 :70 —81
[36] Engelhardt J , Goldwasser J , Hall W K, et al . J . Catal . , 1982 ,76 : 48 —60
[37] Golawasser J , Engelhardt J , Hall W K, et al . J . Catal . , 1981 ,70 : 275 —286
[38] Grünert W, Stakheev A Y, Feldhaus R , et al . J . Catal . , 1992 ,135 : 287 —299
[39] Ramos I R , Ruiz A G, Homs N , et al . J . Mol . Catal . , 1995 ,95 : 147 —154
[40] Rappe A K, Goddard W A. J . Am. Chem. Soc. , 1982 , 104 :448 —456
[41] Thomas R , Moulijn J A , de Beer V HJ , et al . J . Mol . Catal . ,1980 , 8 : 161 —174
[42] Tanaka K, Miyahara K, Tanaka K I. Proc. 7th Int . Congr.Catal . Tokyo. Amsterdam: Elsevier , 1981. 1318
[43] Zhang B A , Liu N S , Lin Q S , et al . J . Mol . Catal . , 1991 , 65 :15 —28
[44] Aritani H , Fukudao O , Yamamoto T , et al . Chem. Lett . , 2000 ,66 —67
[45] Aritani H , Fukuda O , Miyaji A , et al . Appl . Sur. Sci . , 2001 ,180 : 261 —269
[46] Brown T L. J . Mol . Catal . , 1981 , 12 : 41 —62
[47] Duquette L G, Cieslinsky R C , Jung C W, et al . J . Catal . ,1984 , 90 : 362 —365
[48] Xu Y, Huang J , Guo X. J . Mol . Catal . , 1991 , 65 : 275 —285
[49] Edrevakardjieva R M, Andreev A A. J . Mol . Catal . , 1988 , 46 :201 —207
[50] Xu Y, Wei Y, Guo X, et al . J . Mol . Catal . , 1986 , 36 : 79 —89
[51] Xu Y, Huang J , Guo X, et al . J . Mol . Catal . , 1991 , 65 :275 —285
[52] Nakamura R , Echigoya E. J . Mol . Catal . , 1982 , 15 : 147 —156
[53] Kuznetsov B N , Startsev A N , Yermakov Y I. J . Mol . Catal . ,1980 , 8 : 135 —145
[54] Mol J C. Handbook of Heterogeneous Catalysis ( eds. Ertl G,Knzinger H , Weitkamp J ) , vol . 5. Weinheim: Wiley VCH ,1977. 2387 —2400
[55] Castellan A , Bart J C J , Vaghi A , et al . J . Catal . , 1976 , 42 :162 —172
[56] Iwasawa Y, Ichinose H , Ogasawara S. J . Chem. Soc. Faraday Trans. , 1981 , 77 : 1763 —1777
[57] Sibeijn M, Mol J C. Appl . Catal . , 1991 , 67 : 279 —295
[58] Handzlik J , Ogonowski J , Stoch J , et al . Appl . Catal . A , 2006 ,312 : 213 —219
[59] Henker M, Wendlandt K P , Valyon J , et al . Appl . Catal . ,1991 , 69 : 205 —220
[60] Rajagopal S , Marini H J , Miranda R , et al . J . Catal . , 1994 ,147 : 417 —428
[61] Kiviat F E , Petrakis L. J . Phys. Chem. , 1973 , 77 : 1232 —1239
[62] Drǎgutan V , Balaban A T , Dimonie M. Olefin Metathesis and Ring-Opening Polymerization of Cyclo-Olefins , 2nd revisededition. John Wiley &Sons , Ltd. , 1985. 40 —41
[63] Huang S J , Chen F C , Liu S L , et al . J . Mol . Catal . A , 2007 ,267 : 224 —233
[64] Huang S J , Liu S L , Zhu Q J , et al . Appl . Catal . A , 2007 ,323 : 94 —103
[65] Vuurman M, Stufkens D J , Oskam A , et al . J . Mol . Catal . ,1992 , 76 : 263 —285
[66] Hardcastle F D , Wachs I E , Horsley J A , et al . J . Mol . Catal . ,1988 , 46 : 15 —36
[67] Olsthoorn A A , Boelhouwer C. J . Catal . , 1976 , 46 : 197 —206
[68] Arnoldy P , van Oers E M, de Beer V H J , et al . J . Catal . ,1985 , 93 : 231 —245
[69] Spronk R , Mol J C. Proc. 10th Int . Congr. Catal . (eds. Guczi L , et al . ) . Amsterdam: Elsevier , 1993. 2071
[70] Ookoshi T , Onaka M. Chem. Commun. , 1998 , 2399 —2400
[71] Oikawa T , Ookoshi T , Tanaka T , et al . Micro. Meso. Mat . ,2004 , 74 : 93 —103
[72] Vaghi A , Castellan A , Bart J C J , et al . J . Catal . , 1976 , 42 :381 —387
[73] Thomas R , Moulijn J A. J . Mol . Catal . , 1982 , 15 : 157 —172
[74] Startsev A N , Klimov O V , Khomyakova E A. J . Catal . , 1993 ,139 : 134 —141
[75] Hietala J , Root A , Knuuttila P. J . Catal . , 1994 , 150 : 46 —55
[76] Spronk R , van Veen J A R , Mol J C. J . Catal . , 1993 , 144 :472 —483
[77] Sibeijn M, Spronk R , Mol J C , et al . Catal . Lett . , 1991 , 8 :201 —208
[78] Sheu F C , Hong C T , Huang W L , et al . Catal . Lett . , 1992 ,14 : 297 —304
[79] Xu X D , Mol J C. J . Chem. Soc. Chem. Commun. , 1985 ,631 —633
[80] Schekler-Nahama F , Clause O , Commereuc D , et al . Appl .Catal . A , 1998 , 167 : 237 —245
[81] Li X J , Zhang W P , Bao X H , et al . J . Catal . , 2007 , 250 :55 —66
[82] Mol J C , Andreini A. J . Mol . Catal . , 1988 , 46 : 151 —156
[83] Li X J , Zhang W P , Bao X H , et al . J . Mol . Catal . A , 2006 ,250 : 94 —99
[84] Handzlik J , Stoch J , Ogonowski J , et al . J . Mol . Catal . A ,2000 , 157 : 237 —243
[85] Kalu?a L , Vít Z , Zdra? il M. Appl . Catal . A , 2005 , 282 : 247 —253
[86] Topka P , Balcar H , Rathousky J , et al . Micro. Meso. Mat . ,2006 , 96 : 44 —54
[87] Tanaka K, Tanaka K. J . Chem. Soc. Chem. Commun. , 1984 ,748 —749
[88] Tanaka K, Sasaki M, Toyoshima I. J . Phys. Chem. , 1988 , 92 :4730 —4733
[89] Tanaka K, Tanaka K. J . Chem. Soc. Faraday Trans. , 1987 ,83 : 1859 —1868
[90] Handzlik J , Ogonowski J . Catal . Lett . , 2002 , 83 : 287 —290
[91] Andreini A , Xu X D , Mol J C. Appl . Catal . , 1986 , 27 : 31 —40
[92] Mol J C. J . Mol . Catal . , 1982 , 15 : 35 —45
[93] Handzlik J , Ogonowski J . Catal . Lett . , 2003 , 88 : 119 —122
[94] Tanaka K, Tanaka K. J . Chem. Soc. Faraday Trans. , 1988 ,84 : 601 —608
[95] Tarasov A L , Shelimov B N , Kazansky V B , et al . J . Mol .Catal . A , 1997 , 115 : 219 —228
[96] Astruc D. New J . Chem. , 2005 , 29 : 42 —56
[97] Connon S J , Blechert S. Angew. Chem. Int . Ed. , 2003 , 42 :1900 —1923
[98] Mol J C , Moulijn J A , Boelhouwer C , et al . J . Chem. Soc.Chem. Commun. , 1983 , 130 —132
[99] Vikulov KA , Elev I V , Shelimov B N , et al . J . Mol . Catal . ,1989 , 55 : 126 —145
[100] Shelimov B N , Elev I V , Kazansky V B. J . Mol . Catal . , 1988 ,46 : 187 —200
[101] Vikulov K A , Shelimov B N , Kazansky V B. J . Mol . Catal . ,1991 , 65 : 393 —402
[102] Vikulov K A , Shelimov B N , Kazansky V B. J . Mol . Catal . ,1992 , 72 : 117 —125
[103] Gao F , Wang Y L , Tysoe W T. J . Am. Chem. Soc. , 2006 ,128 : 7091 —7096
[104] Mol J C. Catal . Today , 1999 , 51 : 289 —299
[105] Laverty D T , Rooney J J , Stewart A. J . Catal . , 1976 , 45 :110 —113
[106] Anpo M, Kondo M, Kubokawa Y, et al . J . Chem. Soc. Faraday Trans. , 1988 , 84 : 2771 —2782
[107] Anpo M, Tanahashi I , Kubokawa Y. J . Chem. Soc. Faraday Trans. , 1982 , 78 : 2121 —2128
[108] Spronk R , Andreini A , Mol J C. J . Mol . Catal . , 1991 , 65 :219 —235
[109] Bibby D M, Howe R F , McLellan G D. Appl . Catal . A , 1992 ,93 : 1 —34
[110] Guisnet M, Magnoux P. Stud. Sur. Sci . Catal . , 1994 , 88 : 53 —68
[111] Van Schalkwyk C , Spamer A , Moodley D J . Appl . Catal . A ,2003 , 255 : 143 —152
[112] Kwini M N , Botha J M. Appl . Catal . A , 2005 , 280 : 199 —208
[113] Rodriguezramos I , Guerreroruiz A , Homs N , et al . J . Mol .Catal . A , 1995 , 195 : 147 —154
[114] Amigues P , Chauvin Y, Commereuc D , et al . J . Mol . Catal . ,1991 , 65 : 39 —90
[115] Lehman S E , Schwendeman J E , O’Donnell P M, et al .Inorganica Chimica Acta , 2003 , 345 : 190 —198
[116] Bradshaw C P C , Howman E J , Turner L. J . Catal . , 1967 , 7 :269 —276
[117] Ivin K J , Mol J C. Olefin Metathesis and Polymerization. San Diego : Academic Press , 1997. 97
[118] 黄声骏(Huang S J ) , 刘盛林(Liu S L) , 徐龙伢(Xu L Y)等. 石油化工(Petrochem. Technol . ) , 2003 , 32 : 743 —746
[119] Wang L P , Soto C , Tysoe W T. J . Catal . , 1993 , 143 : 92 —101
[120] Bartlett B F , Schneerson V , Tysoe WT. Catal . Lett . , 1995 , 32 :1 —7
[121] Bartlett B F , Molero H , Tysoe W T. J . Catal . , 1997 , 167 :470 —481
[122] Wu G, Bartlett B F , Tysoe W T. J . Catal . , 1998 , 173 : 172 —176
[123] Bartlett B F , Tysoe W T. Catal . Lett . , 1997 , 46 : 101 —106
[124] Vikulov K V , Shelimov B N , Mol J C , et al . J . Mol . Catal . ,1994 , 90 : 61 —67
[125] Handzlik J . J . Catal . , 2003 , 220 : 23 —34
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摘要

多相催化剂上烯烃交叉歧化反应*