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Progress in Chemistry 2006, Vol. 18 Issue (04): 399-409 Previous Articles   Next Articles

• Review •

Progress in Catalytic Epoxidation of Olefins with Hydrogen Peroxide

Yangying Chen 1,2*;Xiuwen Han2   

  1. 1.State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of  Technology, Dalian 116012, China;2.State Key Laboratory of Catalysis, Dalian Institute of  Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
  • Received: Revised: Online: Published:
  • Contact: Yangying Chen
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Environmentally benign catalytic epoxidation of olefins is one of the important aspects in catalytic oxidation field. Hydrogen peroxide as one of the ideal oxidant is used in many catalytic systems. In this paper, the recent progress in catalytic epoxidation of olefins with hydrogen peroxide, from the aspects of homogeneous and heterogeneous catalytic systems, is summarized, and some systems with prospect in industrial application are described in detail.
Key words: hydrogen peroxide, olefins, epoxidation

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[ 1 ] 吕绍洁(Lu S J ) , 徐成华(Xu C H) , 陈义均(Chen Y J ) 等.合成化学(Chin. J . Syn. Chem. ) , 2000 , 8 (1) : 71 —74
[ 2 ] 韩飞(Han F) . 精细石油化工( Speciality Petrochemicals) ,1998 , 5 : 1 —4
[ 3 ] 郑健(Zhen J ) . 氯碱工业(Chlor-Alkali Industry) , 1998 , 4 :4 —11
[ 4 ] 胡景沧(Hu J C) . 化工设计(Chemical Engineering Design) ,1996 , 1 : 3 —7
[ 5 ] 陈晓晖(Chen X H) , 王保国(Wang B G) , 陈宪(Chen X)等. 化工环保( Environment Protection of Chemical Industry) ,2000 , 4 : 20 —24
[ 6 ] Nijhuis T A , Musch S , Makkee M, et al . Appl . Catal . A:Gen. , 2000 , 196 (2) : 217 —224
[ 7 ] Monnier J R. Appl . Catal . A: Gen. , 2001 , 221 (1/2) : 73 —91
[ 8 ] Hamamoto M, Nakayama K, Nishiyama Y, et al . J . Org.Chem. , 1993 , 58 (23) : 6421 —6425
[ 9 ] Neumann R , Dahan M. Nature , 1997 , 388 (6640) : 353 —355
[10] Nishiyama Y, Nakagawa Y, Mizuno N. Angew. Chem. Int .Ed. , 2001 , 40 (19) : 3639 —3640
[11] Grigoropoulou G, Clark J H , Eling J A. Green Chem. , 2003 , 5 :1 —7
[12] Lane B S , Burgess K. Chem. Rev. , 2003 , 103 (7) : 2457 —2473
[13] Venturello C , Alneri E , Ricci M. J . Org. Chem. , 1983 , 48 :3831 —3833
[14] Sato K, Aoki M, Ogawa M, et al . J . Org. Chem. , 1996 , 61(23) : 8310 —8311
[15] Venturello C , D’aloisio R , Bart J C J . J . Mol . Catal . , 1985 ,32 : 107 —110
[16] Duncan D C , Chambers R C , Hecht E , et al . J . Am. Chem.Soc. , 1995 , 117 (2) : 681 —691
[17] Ishii Y. J . Org. Chem. , 1988 , 3587 —3589
[18] Aubry C , Chottard G, Platzer N , et al . Inorg. Chem. , 1991 , 30(23) : 4409 —4415
[19] Salles L , Aubry C , Thouvenot R , et al . Inorg. Chem. , 1994 , 33(5) : 871 —878
[20] Sakaue S , Sakata Y, Nishiyama Y, et al . Chem. Lett . , 1992 ,2 : 289 —292
[21] Griffith W P. J . Chem. Soc. , Dalton Trans. , 1989 , 14 : 1203 —1205
[22] Dengel A C , Griffith W P , Parkin B C. J . Chem. Soc. , Dalton Trans. , 1993 , 18 : 2683 —2688
[23] Xi Z W, Zhou N , Sun Y, et al . Science , 2001 , 292 (5519) :1139 —1141
[24] Sun Y, Xi Z W, Cao G Y. J . Mol . Catal . A: Chem. , 2001 ,166 (2) : 219 —224
[25] Chen Y Y, Zhuang J Q , Liu X M, et al . Catal . Lett . , 2004 , 93(1/2) :41 —46
[26] Neumann R , Gara M. J . Am. Chem. Soc. , 1995 , 117 (18) :5066 —5074
[27] Neumann R , Gara M. J . Am. Chem. Soc. , 1994 , 116 (12) :5509 —5510
[28] Adam W, Alsters P L , Neumann R , et al . J . Org. Chem. ,2003 , 68 (5) : 1721 —1728
[29] Vasylyev M V , Neumann R. J . Am. Chem. Soc. , 2004 , 126(3) : 884 —890
[30] Kamata K, Yonehara K, Sumida Y, et al . Science , 2003 , 300(5621) : 964 —966
[31] Kamata K, Nakagawa Y, Yamaguchi K, et al . J . Catal . , 2004 ,224 (1) : 224 —228
[32] Nakagawa Y, Kamata K, Kotani M, et al . Angew. Chem. Int .Ed. , 2005 , 44 : 2 —6
[33] Espenson J H. Chem. Commun. , 1999 , 479 —488
[34] Gans? uer A. Angew. Chem. Int . Ed. , 1997 , 36 (23) : 2591 —2592
[35] Herrmann WA , Fischer R W, Marz D W. Angew. Chem. Int .Ed. , 1991 , 30 (12) : 1638 —1641
[36] Adam W, Mitchell C M. Angew. Chem. Int . Ed. , 1996 , 35(5) : 533 —535
[37] Rudolph J , Reddy KL , Chiang J P , et al . J . Am. Chem. Soc. ,1997 , 119 (26) : 6189 —6190
[38] Van Vliet M C A , Arends I W C E , Sheldon R A. Chem.Commun. , 1999 , 821 —822
[39] Adolfsson H , Coperet C , Chiang J P , et al . J . Org. Chem. ,2000 , 65 (25) : 8651 —8658
[40] Shu L H , Shi Y. Tetrahedron Lett . , 1999 , 40 (50) : 8721 —8724
[41] Shu L H , Shi Y. J . Org. Chem. , 2000 , 65 (25) : 8807 —8810
[42] Majetich G, Hicks R , Sun GR , et al . J . Org. Chem. , 1998 , 63(8) : 2564 —2573
[43] Hancu D , Green J , Beckman EJ . Acc. Chem. Res. , 2002 , 35(9) : 757 —764
[44] Van Vliet M C A , Arends I W C E , Sheldon R A. Chem.Commun. , 1999 , 3 : 263 —264
[45] Neimann K, Neumann R. Chem. Commun. , 2001 , 487 —488
[46] Kluge R , Schulz M, Liebsch S. Tetrahedron , 1996 , 52 ( 8) :2957 —2976
[47] Nielsen A T, Atkins R L , Norris W P , et al . J . Org. Chem. ,1980 , 45 : 2341 —2345
[48] Yan Z H , Tian W S. Tetrahedron Lett . , 2004 , 45 (10) : 2211 —2213
[49] Wahlen J , de Vos D E , Jacobs P A. Organic Lett . , 2003 , 5(10) :1777 —1780
[50] Battioni P , Renaud J P , Bartoli J F , et al . Chem. Commun. ,1986 , 341 —342
[51] Banfi S , Legramandi F , Montanari F , et al . Chem. Commun. ,1991 , 1285 —1287
[52] Anelli P L , Banfi S , Legramandi F , et al . J . Chem. Soc. ,Perkin Trans. , 1993 , 1 (12) : 1345 —1357
[53] Srinivas K A , Kumar A , Chauhan S M S. Chem. Commun. ,2002 , 20 : 2456 —2457
[54] Rebelo S L H , Pereira M M, Simèes M M Q , et al . J . Catal . ,2005 , 234 : 76 —87
[55] Lane B S , Vogt M, deRose V J , et al . J . Am. Chem. Soc. ,2002 , 124 (40) : 11946 —11954
[56] Tong K H , Wong K Y, Chan T H. Tetrhedron , 2005 , 61 ,6009 —6014
[57] de P ALV , Sels B F , de Vos D E , et al . J . Org. Chem. , 1999 ,64 (19) : 7267 —7270
[58] Hoegaerts D , Sels B F , de Vos D E , et al . Catal . Today , 2000 ,60 (3/4) : 209 —218
[59] Gebard G C R. Acad. Sci . Paris , Serie IIc , Chim.PChem. ,2000 , 3 : 757 —760
[60] Yamada Y M A , Ichinohe M, Takahashi H , et al . Org. Lett . ,2001 , 3 : 1839 —1840
[61] Ghiron C , Nannetti L , Taddei M. Tetrahydron Lett . , 2005 , 46 :1643 —1645
[62] Elings J A , Ait-Meddour R , Clark J H , et al . Chem. Commun. ,1998 , 24 : 2707 —2708
[63] Cohen M, Neumann R. J . Mol . Catal . , 1999 , 146 (1/2) : 291 —298
[64] Sakamoto T, Pac C J , Tetrahedron Lett . , 2000 , 41 ( 51 ) :10009 —10012
[65] Xiang S , Zhang Y L , Xin Q , Li C. Angew. Chem. Int . Ed. ,2002 , 41 (5) : 821 —823
[66] Zhou X G, Yu X Q , Huang J S , et al . Chem. Commun. , 1999 ,18 : 1789 —1790
[67] De Vos D E , de Wildeman S , Sels B F , et al . Angew. Chem.Int . Ed. Engl . , 1999 , 38 (7) : 980 —983
[68] Ueno S , Yamaguchi K, Yoshida K, et al . Chem. Commun. ,1998 , 295 —296
[69] Sels B , de Vos D , BuntinxM, et al . Nature , 1999 , 400 (6747) :855 —857
[70] 薛俊利( Xue J L) , 孟祥坤(Meng X K) , 许锡恩(Xu X E) .化工进展(Chemical Industry and Engineering Progress) , 1999 ,2 : 15 —24
[71] Murugavel R , Roesky H W. Angew. Chem. Int . Ed. , 1997 , 36(5) : 477 —479
[72] Perego C , Carati A , Ingallina P , et al . Appl . Catal . A: Gen. ,2001 , 221 (1/2) : 63 —72
[73] 张小明(Zhang X M) , 张兆荣(Zhang Z R) , 索继栓(Suo J S) 等. 分子催化(J . Mol . Catal . ) , 1997 , 3 : 230 —239
[74] 周继承(Zhou J C) , 王祥生(Wang X S) . 化学进展(Progress in Chemistry) , 1998 , 4 : 383 —394
[75] Nijhuis T A , Musch S , Makkee M, et al . Appl . Catal . A:Gen. , 2000 , 196 (2) : 217 —224
[76] Monnier J R. Appl . Catal . A: Gen. , 2001 , 221 (1P2) : 73 —91
[77] 王海平(Wang H P) , 奚祖威(Xi Z W) , 曹国英(Cao G Y)等. 分子催化(Chin. J . Mol . Catal . ) , 2000 , 14 (1) : 74 —80
[78] Kresge C T, Leonowicz M E , Roth W J , et al . Nature , 1992 ,359 (6397) : 710 —712
[79] Ying J Y, Mehnert C P , Wong M S. Angew. Chem. Int . Ed.Engl . , 1999 , 38 (1/2) : 56 —77
[80] Blasco T, Corma A , Navarro M T, et al . J . Catal . , 1995 , 156(1) : 65 —74
[81] Bagshaw S A , DiRenzo F , Fajula F. Chem. Commun. , 1996 ,2209 —2210
[82] Chen Y Y, Huang Y, Xiu J H , et al . Appl . Catal . A: Gen. ,2004 , 273 (1/2) : 185 —191
[83] Ichihara J , Kambara A , Iteya K, et al . Green Chem. , 2003 , 5(5) : 491 —493
[84] Piquemal J Y, Briot E , Vennat M, et al . Chem. Commun. ,1999 , 13 : 1195 —1196
[85] Dai W L , Chen H , Cao Y, et al . Chem. Commun. , 2003 , 7 :892 —893
[86] Briot E , Piquemal J Y, Vennat M, et al . J . Mater. Chem. ,2000 , 10 : 953 —958
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