乙烯齐聚工艺——从非选择性齐聚到选择性齐聚
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摘要
线性α-烯烃是一类重要的有机化工原料,主要通过乙烯齐聚工艺生产。介绍了乙烯非选择性齐聚工艺(包括Chevron工艺、B P Amoco工艺、Shell工艺、Idemitsu工艺、Alfene工艺、Exxom工艺、AlphaSelect工艺)以及乙烯选择性齐聚工艺(包括乙烯三聚及乙烯四聚)的发展现状。分析了乙烯选择性齐聚存在的问题,并指出了今后的发展方向。
Linear alpha-olefin is an important class of organic chemical raw material that is produced primarily by the ethylene oligomerization process.The paper mainly introduces the development of the non-selective oligomerization technology of ethylene(including Chevron technology,BPAmoco technology,Shell technology,Idemitsu technology,Alfene technology,Exxom technology,AlphaSelect technology)and ethylene selective oligomerization technology(including ethylene trimerization and ethylene tetramerization).The problem of the selective oligomerization of ethylene is analyzed,and the direction of future development is pointed out.
Linear alpha-olefin is an important class of organic chemical raw material that is produced primarily by the ethylene oligomerization process.The paper mainly introduces the development of the non-selective oligomerization technology of ethylene(including Chevron technology,BPAmoco technology,Shell technology,Idemitsu technology,Alfene technology,Exxom technology,AlphaSelect technology)and ethylene selective oligomerization technology(including ethylene trimerization and ethylene tetramerization).The problem of the selective oligomerization of ethylene is analyzed,and the direction of future development is pointed out.
引文
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[2]宋闯,毛国梁,刘振华,等.均相Cr系催化剂催化乙烯选择性齐聚反应机理研究进展[J].有机化学,2016,36(9):2105-2120.
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[10]封智超,毛国梁,吴韦,等.基于5-氨基邻甲酚的膦配体的合成及在乙烯齐聚中的应用[J].有机化学,2018,38(3):698-704.
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[17]WANG T,GAO X,SHI P,et al.Mixed aluminoxanes:eficient cocatalysts for bisphosphineamine/Cr(I)catalyzed ethylene tetramerization toward 1-octene[J].Applied Petrochemical Research,2015,5(2):143-149.
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[19]CARTERA,COHEN S A,COOLEY N A,et al.High activity ethylene trimerisation catalysts based on diphosphine ligands[J].Chem Commun,2002(8):858-859.
[20]毛国梁,郑德金,王钦,等.乙烯四聚用Cr(Ⅲ)系催化剂配体的研究进展[J].合成树脂及塑料,2014,31(3):75-79.
[21]BOLLMANN A,BLANN K,DIXON J T,et al.Ethylenetetramerization:a new route to produce 1-octene in exceptionally high selectivities[J].J Am Chem Soc,2004,126(45):14712-14713.
[22]毛国梁,宁英男,胡文博,等.新型三核双膦胺(PNP)配体的合成及其在乙烯四聚反应中的应用[J].科学通报,2008(21):2592-2595.
[23]BOLLMANN ANNETTE,BLANN KEVIN,DIXON JOHNT,et al.Ethylene tetramerization:A new route to produce 1-octene in exceptionally high selectivities[J].J Am Chem Soc,2004,126(45):14712-14713.
[24]BLANN KEVIN,BOLLMANN ANNETTE,DIXON JOHNT,et al.Highly selective chromium-based ethylene trimerisation catalysts with bulky diphosphinoamine ligands[J].Chem Commun,2005(5):620-621.
[25]MAO G L,NING Y N,HU W B,et al.Synthesis of a novel triplesite diphosphinoamine(PNP)ligand and its applications in ethylene tetramerization[J].Chinese Science Bulletin,2008,53(22):3511-3515.
[26]JIANG T,TAO Y Q,GAO X L,et al.Ethylene tetramerization with a highly active and long-lifetime trinuclear diphenyl-phosphinoamine/Cr(Ⅲ)/MAO catalyst[J].Chinese Science Bulletin,2012,57(13):1510-1515.
[27]宋宪凤,毕四勇,毛国梁,等.乙烯三聚和四聚催化剂的研究进展[J].石油化工,2008,37(8):858-862.
[28]刘睿,肖树萌,钟向宏,等.基于[PNP]配体的铬催化剂体系选择性催化乙烯齐聚的研究进展[J].有机化学,2015,35(9):1861-1888.
[29]MANYIKRM,WALKERWE,WILSONTP.Asoluble chromium-based catalyst for ethylene trimerization and polymerization[J].J Catal,1977,47(2):197-209.
[30]PEITZ S,ALURI B R,PEULECKE N,et al.An alternative mechanistic concept for homogeneous selective ethylene oligomerization of chromium-based catalysts:Binuclear metallacycles as a reason for 1-octene selectivity[J].Chem Eur,2010,16(26):7670-7676.
[31]刘振华,毛国梁,宋闯,等.带有PNP配体的铬系催化剂在乙烯选择性齐聚中的研究进展[J].能源化工,2016,37(4):1-10.
[2]宋闯,毛国梁,刘振华,等.均相Cr系催化剂催化乙烯选择性齐聚反应机理研究进展[J].有机化学,2016,36(9):2105-2120.
[3]AN J X.The synthetic lubricating oil market position and development trend[J].Synthetic Lubricant Material,2016,43(2):14-17.
[4]CARTER A,COHEN S A,COOLEY N A,et al.High activity ethylene trimerisation catalysts based on diphosphine ligands[J].Chemical Communications,2002,8(8):858-859.
[5]封智超,毛国梁,吴韦,等.铬系乙烯选择性齐聚催化剂的研究进展[J].石油学报(石油加工),2018,34(1):190-202.
[6]赵惠萍.1-辛烯生产工艺[J].石化技术,2006(1):59-64.
[7]李山明.新型三核双膦胺(PNP)配体用于乙烯四聚的研究[D].大庆:大庆石油学院,2009.
[8]李达刚,刘东兵.对SHOP法乙烯齐聚制α-烯烃催化剂的改进与创新[J].石油化工,1999(5):17-20.
[9]薛秋梅.新型PNP配体的合成及乙烯齐聚性能研究[D].大庆:东北石油大学,2011.
[10]封智超,毛国梁,吴韦,等.基于5-氨基邻甲酚的膦配体的合成及在乙烯齐聚中的应用[J].有机化学,2018,38(3):698-704.
[11]RAINER E,OLIVER H,PETER W J,et al.The role of metal lacycles in the chromium-catalyzed trimerization of ethylene[J].Organometallics,1997,16:1511-1513.
[12]MANYRK R M,WALKER W E,WSLILSON T P.A soluble chromrum-based catalyst or ethylene trimerization and polymerization[J].J Cat,1977,47:197-219.
[13]姜涛,阎卫东,刘立新,等.乙烯三聚制1-己烯研究进展[J].石化技术与应用,2000(5):284-287.
[14]隋军龙,杜向东,栗同林.乙烯三聚制1-己烯的研究[J].合成树脂及塑料,2001(2):23-25.
[15]LIU S L,YUAN W,LUO C T.Production and application ofα-olefins[J].Aging and Application of Synthetic Materials,2016,45(3):132-135.
[16]王俊,李云,李翠勤,等.铬系聚乙烯催化剂研究开发新进展[J].化工进展,2012,31(1):91-97.
[17]WANG T,GAO X,SHI P,et al.Mixed aluminoxanes:eficient cocatalysts for bisphosphineamine/Cr(I)catalyzed ethylene tetramerization toward 1-octene[J].Applied Petrochemical Research,2015,5(2):143-149.
[18]王静,朱博超,董金勇,等.乙烯齐聚催化剂研究进展[J].高分子通报,2007(12):17-23.
[19]CARTERA,COHEN S A,COOLEY N A,et al.High activity ethylene trimerisation catalysts based on diphosphine ligands[J].Chem Commun,2002(8):858-859.
[20]毛国梁,郑德金,王钦,等.乙烯四聚用Cr(Ⅲ)系催化剂配体的研究进展[J].合成树脂及塑料,2014,31(3):75-79.
[21]BOLLMANN A,BLANN K,DIXON J T,et al.Ethylenetetramerization:a new route to produce 1-octene in exceptionally high selectivities[J].J Am Chem Soc,2004,126(45):14712-14713.
[22]毛国梁,宁英男,胡文博,等.新型三核双膦胺(PNP)配体的合成及其在乙烯四聚反应中的应用[J].科学通报,2008(21):2592-2595.
[23]BOLLMANN ANNETTE,BLANN KEVIN,DIXON JOHNT,et al.Ethylene tetramerization:A new route to produce 1-octene in exceptionally high selectivities[J].J Am Chem Soc,2004,126(45):14712-14713.
[24]BLANN KEVIN,BOLLMANN ANNETTE,DIXON JOHNT,et al.Highly selective chromium-based ethylene trimerisation catalysts with bulky diphosphinoamine ligands[J].Chem Commun,2005(5):620-621.
[25]MAO G L,NING Y N,HU W B,et al.Synthesis of a novel triplesite diphosphinoamine(PNP)ligand and its applications in ethylene tetramerization[J].Chinese Science Bulletin,2008,53(22):3511-3515.
[26]JIANG T,TAO Y Q,GAO X L,et al.Ethylene tetramerization with a highly active and long-lifetime trinuclear diphenyl-phosphinoamine/Cr(Ⅲ)/MAO catalyst[J].Chinese Science Bulletin,2012,57(13):1510-1515.
[27]宋宪凤,毕四勇,毛国梁,等.乙烯三聚和四聚催化剂的研究进展[J].石油化工,2008,37(8):858-862.
[28]刘睿,肖树萌,钟向宏,等.基于[PNP]配体的铬催化剂体系选择性催化乙烯齐聚的研究进展[J].有机化学,2015,35(9):1861-1888.
[29]MANYIKRM,WALKERWE,WILSONTP.Asoluble chromium-based catalyst for ethylene trimerization and polymerization[J].J Catal,1977,47(2):197-209.
[30]PEITZ S,ALURI B R,PEULECKE N,et al.An alternative mechanistic concept for homogeneous selective ethylene oligomerization of chromium-based catalysts:Binuclear metallacycles as a reason for 1-octene selectivity[J].Chem Eur,2010,16(26):7670-7676.
[31]刘振华,毛国梁,宋闯,等.带有PNP配体的铬系催化剂在乙烯选择性齐聚中的研究进展[J].能源化工,2016,37(4):1-10.
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