English
往期目录
新闻公告
More
化学进展 2005, Vol. 17 Issue (02): 209-216 前一篇   后一篇

• •

液/液两相催化高碳烯烃氢甲酰化反应*

冯翠兰 王艳华 金子林**   

  1. (大连理工大学精细化工国家重点实验室　大连116012)
  • 收稿日期:2003-12-01 修回日期:2004-06-01 出版日期:2005-03-24 发布日期:2005-03-24
  • 通讯作者: 金子林 E-mail:hpzuo @mail. dlptt. ln. cn
  • 基金资助:

    国家自然科学基金;教育部博士点科研基金

下载PDF ( 1559 ) 引用
导出

The Development in Hydroformylation of Higher Olefin in LiquidPLiquid Biphase Systems

feng Cuilan Wang Yanhua Jin Zilin**   

  1. (State Key Laboratory of Fine Chemicals , Dalian University of Technology , Dalian 116012 , China)
  • Received:2003-12-01 Revised:2004-06-01 Online:2005-03-24 Published:2005-03-24
  • Contact: Jin Zilin E-mail:hpzuo @mail. dlptt. ln. cn

结合作者近年来的研究工作,对液P液两相催化高碳烯烃氢甲酰化的研究进展作一综述,针对经典的水P有机两相体系不能用于高碳烯烃氢甲酰化的问题,全面介绍了适用于高碳烯烃水P有机两相氢甲酰化的温控相转移催化等6 种改进方法。同时,对90 年代以来发展迅速的氟两相、离子液体两相、超临界流体等非水液P液两相体系中的高碳烯烃氢甲酰化作了系统阐述,对它们的应用前景进行了评较。

关键词： 氢甲酰化反应, 水/有机两相, 温控相转移催化, 氟两相, 离子液体两相, 超临界流体, 温控相分离催化

The development in hydroformylation of higher olefins in liquidP liquid biphase systems is reviewed , par2 tially based on the authors’research results in recent years. The classical aqueousPorganic biphase system is unsuitable for hydroformylation of higher olefins. In order to solve this problem , six kinds of improved methods including thermoreg2 ulated phase2transfer catalysis are introduced in detail . In addition , the hydroformylation of higher olefins in nonaqueous liquidP liquid biphase systems , such as fluorous biphasic system , non2aqueous ionic liquid and supercritical fluid is also introduced. Meanwhile , the possibilities of commercial applications of each system have been discussed.

Key words: hydroformylation, aqueouesPorganic biphase system, thermoregulated phase2transfer catalysis, flu/orous biphasic system, non2aqueous ionic liquid, supercritical fluid, thermoregulated phase/separable catalysis

中图分类号: 

()

[ 1 ] Bahrmann H , Bogdamovic S. Aqueous Phase Organometallic Catalysis ( eds. Cormils B , Herrmann W A) . Weinheim: Wiley VCH , 1998. 306 —321
[ 2 ] 刘春(Liu C) , 梅建庭(Men J T) , 金子林(Jin Z L) . 化工进展(Chemical Industry and Engineering Progress) , 2000 , 19 (1) :28 —31
[ 3 ] Bahrmann H , Cornils B. DE 3 412 335 , 1985
[ 4 ] Cornils B , Konkol W, Bahrmann H. DE 3 447 030 , 1986
[ 5 ] Ding H , Hanson B E , Glass T E. Inorg. Chim. Acta , 1995(229) : 329 —333
[ 6 ] Ding H , Hanson B E , Bartik B. Organometallics , 1994 , 13 :3761 —3763
[ 7 ] Russell M J H. Platinum Met . Rev. , 1988 , 34(4) : 179
[ 8 ] Russell M J H , Murrer B A. BP 208 574 , 1981
[ 9 ] 吴乙丑(Wu Y C) , 袁刚(Yuan G) , 周启昭(Zhou Q Z) . 石油化工(Petrochemical Technology) , 1990 , 19(4) : 209 —214
[10] 陈华(Chen H) , 李贤均(Liu X J) 等. 分子催化(Journal of Mo lecular Catalysis) , 1994 , 8(5) : 347 —352
[11] 陈华(Chen H) , 李贤均(Liu X J) 等. 分子催化(Journal of Mo lecular Catalysis) , 1995 , 9(2) : 145 —151
[12] Fell B , Papadogianakis G. J . Mol . Catal . , 1991(66) : 143 —154
[13] Bvartik T , Bartik B , Hanson B E. J . Mol . Catal . , 1995 (98) :117 —122
[14] Bvartik T , Bartik B , Hanson B E , et al . Organometallics , 1993(12) : 164 —170
[15] Bartik T , Bartik B , Hanson B E. J . Mol . Catal . , 1994 , 88 :43 —56
[16] Chem H , Li Y, Li X. J . Mol . Catal . , 1999 , 149 : 1 —6
[17] Buhing A , Kamer P C J , Leeuwen P W N M. J . Mol . Catal . ,1995 , 98 : 69 —80
[18] Buhing A , Elgersma J W, Kamer P C J , Leeuwen P W N M. J Mol . Catal . , 1997 , 116 : 297 —308
[19] Buhing A , Elgersma J W, Nkrumah S , Kamer P C J , Leeuwen P W N M. J , Chem. Soc. , Dalton Trans. , 1996 : 2143 —2154
[20] Monflied E , Tilloy S , Fremy G, et al . Tetrahedron Lett . , 1995 ,36(52) : 9481 —9489
[21] Monflied E , Framy G, Castanet Y, et al . Angew. Chem. Int .Ed. Eng. , 1995 , 34(20) : 2269 —2271
[22] Deshpande R , Fukuoka A , Ichikawa M. Chem. Lett . , 1999 , 1 :13 —14
[23] Reetz M T , Waldvogel S R. Angew. Chem. Int . Ed. Engl . ,1997 , 36(8) : 865 —867
[24] Reetz M T. Catal . Today , 1998 , 42 : 399 —411
[25] Tilloy S , Bertoux F , Montreux A , et al . Catal . Today , 1999 ,48 : 245 —253
[26] Chaudhari R V , Bhanage B M, Deshpande R M. Nature , 1995 ,373 : 501 —502
[27] Cornils B. Angew. Chem. Int . Ed. Engl . , 1995 , 34 : 1575 —1577
[28] Chaudhari R V ,Bhanage B M. Aqueous- Phase Organometallic Cataplysis ( eds. Cormils B , Herrmann W A) . Weinheim: Wiley-VCH , 1998. 283 —294
[29] Chen R F , Liu X Z , Jin Z L. J . Organomet . Chem. , 1998 , 571(2) : 201 —204
[30] Jiang J Y, Wang Y H , Liu C , Han F S , Jin Z L. J . Mol . Catal .A , 1999 , 147 (1P2) : 131 —136
[31] Jin Z L , Yan Y Y, Zuo H P , Fell B. J . Prakt . Chem. , 1996 ,338(2) : 124 —128
[32] 刘春(Liu C) . 大连理工大学博士论文(Doctoral Thesis of Dalian University of Technology) , 2000
[33] Bailey F E , Koleke J V. Poly(ethylene oxide) . New York : Academic Press , 1976
[34] Jin Z L , Zheng X L , Fell B. J . Mol . Catal . A , 1997 , 116(1) :55 —58
[35] Horvath I T , Rabai J . Science , 1994 , 266 : 72 —75
[36] Chauvin Y, Olivier H. Angew. Chem. Int . Ed. Engl . , 1995 ,34 : 2698 —2700
[37] Waffenschmidt H , Wasserscheid P. J . Mol . Catal . , 2000 , 164 :61 —67
[38] McHugh M, Krukonis V. Supercritical Fluid Extraction , Principles and Practice. Boston : Butterworths , 1986
[39] Wang Y, Jiang J , Wu X, Cheng F , Jin Z. Catal . Letter , 2002 ,79 : 55
[40] Horvath I T , Rabai J , Horvatn I T. EP 633 062 , 1995
[41] Horvath I T , Kiss G, Cook R A , et al . J . Am. Chem. Soc. ,1998 , 120 : 3133 —3143
[42] Horvath I T , Rabai J . US 5 463 082 , 1995
[43] Bhattacharyya P , Croxtall B , Fawcett J , Fawcett J , Gudmunsen D , Hope E G, Kemmitt R D W, Paige D R , Russell D R , Stuart A M, Wood D R W. J . Fluorine Chem. , 2000 , 101 : 247 —255
[44] Hope E G, Stuart A M. J . Fluorine Chem. , 1999 , 100 : 75 —83
[45] Stuart A M, Gudmunsen D , Hope E G, Schwarz G P , Foster D F , Cole2Hamilton D J . UK26 619 , 1998
[46] Cornils B. Angew. Chem. Int . Ed. Engl . , 1997 , 36 : 2057 —2059
[47] Counils B. Angew. Chem. Int . Ed. Engl . , 1995 , 34 ( 15) :1575 —1577
[48] Gordon C M. Applied Catal . A: General , 2001 , 222 : 101 —117
[49] Wasserscheid P , Waffenschmidt H. J . Mol . Catal . A: Chem. ,2000 , 164 : 61 —67
[50] Olivier H. J . Mol . Catal . A: Chem. , 1999 , 146 : 285 —289
[51] Ngo HL , LeCompte K, Hargens L , McEwen A B. Thermochimica Acta , 2000 , 357 —358 : 97 —102
[52] Karodia N , Guise S , Newlands C , Andersen J A. Chem. Commun. , 1998 , 2341 —2342
[53] Rogers R D , Sedden K R. Science , 2003 , 302 : 792 —793
[54] David J , Cole2Hamilton O J . Science , 2003 , 299 : 1702 —1706
[55] Jessop P G, Hsion Y, Ikariya T , Noyori R. J . Am. Chem.Soc. , 1996 , 118 : 344 —355
[56] Yazdi A V , Beckman E J . Mater. Res. , 1995 , 10 : 530 —537
[57] Yazdi A V , Beckman EJ . Ind. Eng. Chem. (Seoul) 1997 , 36 :2368 —2374
[58] Kainz S , Koch D , Baumann W, Leitner W. Angew. Chem. Int .Ed. Engl . , 1997 , 36 : 1628 —1630
[59] Jentoft R E , Gouw T H. Anal . Chem. , 1972 , 44 : 681
[60] Hughes R P , Trujillo H A. Organometallics , 1996 , 15 : 286 —294
[61] Bhattacharyya P , Gudmunsen D , Hope E G. J . Chem. Soc. ,Perkin Trans. 1 , 1997 , 3609 —3612
[62] Erkey C , Davis T. Ind. Eng. Chem. Res. , 2000 , 39 : 3671 —3678
[63] Palo D R , Erkey C. Ind. Eng. Chem. Res. , 1998 , 37 : 4203 —4206
[64] Palo D R , Erkey C. Organometallics , 2000 , 19 : 81 —86
[65] Timothy D , Erkey C. Ind. Eng. Chem. Res. , 2000 , 39 : 3671—3678
[66] Palo D R , Erkey C. Ind. Eng. Chem. Res. , 1998 , 38 : 2163 —2165
[67] Sellin M F , Webb P B , Cole-Hamilton D J . Chem. Commun. ,2001 , 781 —782
[68] 郑晓来(Zheng X L) , 陈瑞芳(Cheng R F) , 金子林(Jin Z L) ,高等学校化学学报(Chem. J . Chinese Universities) , 1998 , 19(4) : 574 —576
[69] Jin Z L , Mei J T , Jiang J Y. Chem. J . Chinese Universities ,2000 , 21(6) : 941 —946
[70] Wang Y H , Jiang J Y, Zhang R , Liu X Z. Jin Z L. J . Mol .Catal . , 2000 , 157 : 111 —115
[71] Wang Y H , Jiang J Y, Cheng F , Jin Z L. J . Mol . Catal . , 2002 ,188 : 79 —83
[72] 吴小伟(Wu X W) , 王艳华(Wang Y H) , 赵玉亮(Zhao Y L) ,金子林(Jin Z L) . 催化学报(Chinese Journal of Catalysis) ,2002 , 23(4) : 388 —390
[73] 吴小伟(Wu X W) , 王艳华(Wang Y H) , 程　(Cheng F) , 金子林(Jin Z L) . 高等学校化学学报(Chem. J . Chinese Universities) , 2002 , 23(10) : 1939 —1943
[1] 翁西伦, 鲍宗必, 罗飞, 苏宝根, 杨亦文, 任其龙. 纤维素类手性色谱固定相的制备及其应用[J]. 化学进展, 2014, 26(0203): 415-423.
[2] 倪敏, 徐琴琴, 徐刚, 王恩俊, 银建中. 超临界流体输运技术在缓/控释药物制备中的应用[J]. 化学进展, 2011, 23(8): 1611-1617.
[3] 朱礼洋, 文明芬, 段五华, 徐景明, 朱永(贝睿). 超临界流体萃取技术在乏燃料后处理中的应用[J]. 化学进展, 2011, 23(7): 1308-1315.
[4] 金子林 刘宁 刘春. 温控液/液两相催化进展*[J]. 化学进展, 2010, 22(07): 1295-1309.
[5] 张怀平,陈鸣才. 超临界二氧化碳中的聚合反应*[J]. 化学进展, 2009, 21(09): 1869-1879.
[6] 银建中,张宪阵,徐琴琴,张传杰,王爱琴. 超临界流体沉积技术在纳米复合材料制备中的应用*[J]. 化学进展, 2009, 21(04): 606-614.
[7] 许群,倪伟. 超临界流体技术制备纳米材料的研究与展望[J]. 化学进展, 2007, 19(9): 1419-1427.
[8] 刘伟,张宝泉,刘秀凤. 钯复合膜的研究进展*[J]. 化学进展, 2006, 18(11): 1468-1481.
[9] 姜涛 韩布兴 . 超临界流体化学热力学[J]. 化学进展, 2006, 18(05): 657-669.
[10] 牟天成,韩布兴. 超临界流体的共溶剂效应和混合流体研究进展*[J]. 化学进展, 2006, 18(01): 19-23.
[11] 张阳,杨基础,于养信,李以圭. 分子模拟在超临界流体领域中的应用[J]. 化学进展, 2005, 17(06): 955-962.
[12] 洪海龙,贺文智,索全伶,阿山. 制备超细微粒的超临界流体沉淀技术新进展*[J]. 化学进展, 2005, 17(05): 789-792.
[13] 浮东宝,赵锁奇,浦劲军,孙学文. 超临界流体萃取分离离子液体与有机物及其相平衡的研究*[J]. 化学进展, 2005, 17(05): 793-799.
[14] 刘志敏 张建玲 韩布兴. 超( 近) 临界水中的化学反应[J]. 化学进展, 2005, 17(02): 266-274.
[15] 全灿,李淑芬. 固体溶质在超临界三元系统中的溶解度[J]. 化学进展, 2004, 16(06): 858-.