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Progress in Chemistry 2009, Vol. 21 Issue (04): 784-790 Previous Articles   Next Articles

• Review •

Cross-Metathesis Reaction of Olefins over Heterogeneous Catalysts

Xu Zehui*; Gu Chaoran; Wang Peilin   

  1. (Chemical Research Institute, SINOPEC Shanghai Petrochemical Company Limited, Shanghai 200540, China)
  • Received: Online: Published:
  • Contact: Xu Zehui E-mail:spcxzh@163.com
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Olefin metathesis opens up new industrial processes for the production of important olefins in the field of petrochemicals. In particular, the production of propylene and other important olefins via olefins metathesis reaction from n-butenes feedstock has received considerable attention. The most recent progress of olefin cross-metathesis reaction process, reactive mechanism, catalytic theory and catalysts for metathesis is reviewed in this paper and we try to explain the improved aspect of catalyst performance and provide reference for the study of metathesis catalyst afterwards.

Contents
1 Introduction
2 Cross metathesis process
2.1 Olefin conversion technology
2.2 Meta-4 technology
2.3 BASF technology
2.4 Sasol technology
2.5 SHOP technology
3 Cross-metathesis catalysts
3.1 WO3/SiO2 catalyst
3.2 Re2O7/Al2O3 catalyst
3.3 MoO3/Al2O3 catalyst
3.4 Catalytic performance comparison among three kinds of catalysts
4 Mechanisms of metathesis reaction
4.1 Mechanisms of metathesis reaction over WO3/SiO2 catalyst
4.2 Mechanisms of metathesis reaction over Re2O7/Al2O3 catalyst
4.3 Mechanisms of metathesis reaction over MoO3/Al2O3 catalyst
5 Conclusion

CLC Number: 

[ 1 ]  Banks R L , Bailey G C. Ind. Eng. Chem. Prod. Res. Develo. ,1964 , 3 : 170 —173
[ 2 ]  Schrock R R , Hoveyda A H. Angew. Chem. Int . Ed. Engl . ,2003 , 42 (38) : 4592 —633
[ 3 ]  Chatterjee A K, Choi T L , Sanders D P , Grubbs R H. J . Am.Chem. Soc. , 2003 , 125 (37) : 11360 —11370
[ 4 ]  Funk T W, Efskind J , Grubbs R H. Org. Lett . , 2005 , 7 (2) :187 —190
[ 5 ]  Hsu M C , Junia A J , Haight A R , Zhang W. J . Org. Chem. ,2004 , 69 (11) : 3907 —3911
[ 6 ]  La D S , Sattely E S , Ford J G, Schrock R R , Hoveyda A H. J .Am. Chem. Soc. , 2001 , 15 ;123 (32) : 7767 —7778
[ 7 ]  Chatterjee A K, Grubbs R H. Org. Lett . , 1999 , 1 (11) : 1751 —1753
[ 8 ]  Connon S J , Blechert S. Angew. Chem. Int . Ed. Engl . , 2003 , 42(17) : 1900 —1923
[ 9 ]  Tsang W C , Jernelius J A , Cortez GA , Weatherhead G S , Schrock R R , Hoveyda A H. J . Am. Chem. Soc. , 2003 , 5 ; 125 ( 9) :2591 —2596
[10 ]  Sanford M S , Love J A , Grubbs R H. J . Am. Chem. Soc. , 2001 ,123 (27) : 6543 —6554
[11 ]  Banks R L. Journal of Molecular Catalysis , 1980 , 8 : 269 —276
[12 ]  Mol J C. Journal of Molecular Catalysis A: Chemical , 2004 , 213 :39 —45
[13 ]  Hu J C , Wang YD , Chen L F , et al . Microporous and Mesoporous Materials , 2006 , 93 (1P3) : 158 —163
[14 ]  Huang S J , Liu S L , Xia WJ , et al . Journal of Molecular Catalysis A: Chemical , 2005 , 226 (1) : 61 —68
[15 ]  Moodley D J , van Schalkwyk C , Spamer A , et al . Applied Catalysis A: General , 2007 , 318 : 155 —159
[16 ]  Spamer A , Dube T I , Moodley D J , et al . Applied Catalysis A:General , 2003 , 255 (2) : 133 —142
[17 ]  Van Schalkwyk C , Spamer A , Moodley DJ , et al . Applied Catalysis A: General , 2003 , 255 (2) : 121 —131
[18 ]  Van Schalkwyk C , Spamer A , Moodley DJ , et al . Applied Catalysis A: General , 2003 , 255 (2) : 143 —152
[19 ]  Gartside RJ , Greene M I , Khonsari A M, et al . US 6683019 , 2004
[20 ]  Botha J M, Justice MMJ , Nkosi B S , et al . US 6586649 , 2003
[21 ]  Spamer A , Botha J M, ˇZilkovàN , et al . US 0293548 , 2006
[22 ]  Balcar H , Hamtil R , ˇZilkovàN , et al . Applied Catalysis A:General , 2007 , 320 : 56 —63
[23 ]  Hamtil R , ˇZilkováN , Balcar H , et al . Applied Catalysis A:General , 2006 , 302 (2) : 193 —200
[24 ]  Aguado J , Escola J M, Castro M C , et al . Applied Catalysis A:General , 2005 , 284 (1P2) : 47 —57
[25 ]  Oikawa A , Ookoshi T, Tanaka T, et al . Microporous and Mesoporous Materials , 2004 , 74 (1P3) : 93 —103
[26 ]  Mathew TM, Du Plessis J A K, Prinsloo J J . Journal of Molecular Catalysis A: Chemical , 1999 , 148 (1P2) : 157 —164
[27 ]  Cristiane B , Rodella , Buffon R. Applied Catalysis A: General ,2004 , 263 (2) : 203 —211
[28 ]  Doledec G, Commereuc D. Journal of Molecular Catalysis A: Chemical , 2000 , 161 (1P2) : 125 —140
[29 ]  Sibeijn M, Vanveen J A R , Bliek A , et al . Journal of Catalysis ,1994 , 145 (2) : 416 —428
[30 ]  Spronk R , Andreini A , Mol J C. Journal of Molecular Catalysis ,1991 , 65 (1P2) : 219 —235
[31 ]  Amigues P , Chauvin Y. Journal of Molecular Catalysis , 1991 , 65 (1/2) : 39 —50
[32 ]  Commereuc D , Hugues F , Saussine L. US 6277781 , 2001
[33 ]  Commereuc D , Hugues F , Saussine L. US 6235958 , 2001
[34 ]  Commereuc P , Mikitenkop. US 6437209 , 2002
[35 ]  Commereuc D , Hugues F , Saussine L. US 6624338 , 2003
[36 ]  Euzen P , Guibert S , Kruger-Tissot V , et al . US 6908878 , 2005
[37 ]  Brown D S , Ginestra J M R. US 2006P0116542 , 2006
[38 ]  Handzlik J , Ogonowski J , Stoch J , et al . Applied Catalysis A: General , 2006 , 312 : 213 —219
[39 ]  Handzlik J , Ogonowski J , Stoch J , et al . Applied Catalysis A: General , 2004 , 273 (1P2) : 99 —104
[40 ]  Pantoja A , Sarrin J , Gonzalez L , et al . Journal of Catalysis , 1993 ,142 (1) : 110 —120
[41 ]  Liu SL , Huang SJ , Xin WJ , et al . Catalysis Today , 2004 , 93P95 :471 —476
[42 ]  Kwini M N , Botha J M. Applied Catalysis A: General , 2005 , 280(2) : 199 —208
[43 ]  Lombardo E A , Jacono ML , Hall W K. Journal of Catalysis , 1980 ,64 (1) : 150 —162
[44 ]  Grupp T. , Kohl V , Sch?fer H , et al . Applied Catalysis , 1991 , 76(1) : 61 —77
[45 ]  Basrur A G, Patwardhan S R , Was S N. Journal of Catalysis , 1991 ,127 (1) : 86 —95
[46 ]  Verpoort F , Fiermans L , Bossuyt A R , et al . Journal of Molecular Catalysis , 1994 , 90 (1P2) : 43 —52
[47 ]  Verpoort F , Bossuyt A R , Verdonck L. Journal of Electron Spectroscopy and Related Phenomena , 1996 , 82 (3) : 151 —163
[48 ]  Wang Y D , Chen Q L , Yang W M, et al . Applied Catalysis A:General , 2003 , 250 (1) : 25 —37
[49 ]  Mahmood C S , Yarmo M A , Hamid S B D. Journal of Molecular Catalysis A: Chemical , 2000 , 161 (1P2) : 11 —16
[50 ]  Schekler-Nahama F , Clause O , Commereuc C , et al . Applied Catalysis A: General , 1998 , 167 (2) : 247 —256
[51 ]  Rumeana M, Edreva-Kardjieva M, Vuurman A , et al . Journal of Molecular Catalysis , 1992 , 76 (1P3) : 297 —305
[52 ]  McCoy J R , Farona M F. Journal of Molecular Catalysis , 1991 , 66(1) : 51 —58
[53 ]  Vikulov K A , Shelimov B N , Kazansky V B. Journal of Molecular Catalysis , 1991 , 65 (3) : 393 —402
[54 ]  Lombardo E A , Jacono ML , Hall W K. Journal of Catalysis , 1978 ,51 (2) : 243 —255
[55 ]  Vikulov K A , Shelimov B N , Kazansky V B. Journal of Molecular Catalysis , 1992 , 72 (1) : 1 —11
[56 ]  Vikulov K A , Shelhnov B N , Kazansky V B. Journal of Molecular Catalysis , 1992 , 72 (1) : 117 —125
[57 ]  Oliveros I , Zurita MJ P , Scott C , et al . Journal of Catalysis , 1997 ,171 (2) : 485 —489

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