双功能催化体系催化二氧化碳与环氧化合物的偶联反应研究
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摘要
本论文论述了二氧化碳和环氧化合物偶联反应的研究进展,确定了发展高效、简单、容易重复使用的催化体系的研究方向,同时引入新型的双功能催化体系,用于二氧化碳与环氧化合物的动力学拆分。主要内容和结论如下:
1.在传统的有机盐的基础上,成功地合成了一系列的季翁三溴盐(其中3个为新合成),并首次将其单独用于催化二氧化碳和环氧化合物的偶联反应,表现出较好的催化活性。当其与SalenCoX共同组成双功能催化体系。在温和的条件下(室温、100psi)可以高效地实现偶联反应,其中当共催化剂为苯基三甲基三溴化铵(PTAT)时,催化效果最好,可适合于各种末端取代的环氧化合物。并且在0℃实现了二氧化碳与环氧丙烷的动力学拆分,得到44.7%e.e.值的手性环碳酸酯。
2.开发了溴化锌-季鎓三溴盐简单催化体系催化二氧化碳和环氧化合物偶联反应,考察了反应温度、压力和不同金属盐对反应的影响以及催化剂的循环使用性能。结果表明,在413K和1.0MPa条件下,以溴化锌为催化剂,PTAT为共催化剂,无需加入任何溶剂就可以使二氧化碳和环氧化合物发生偶联反应,并以很高的收率得到环碳酸酯;并且催化剂实现了多次循环,具有工业应用价值。
3.研究了SalenRu(Ⅱ)(PPh_3)_2/SalenRu(Ⅲ)X催化二氧化碳与环氧化合物的偶联反应,考察了不同催化剂、共催化剂、助催化剂、反应温度以及不同的共催化剂对二氧化碳与环氧化合物偶联反应的影响。结果表明,当以SalenRu(Ⅱ)(PPh_3)_2为催化剂,重氮乙酸乙酯(EDA)为助催化剂,PTAT为共催化剂可以实现反应的转化;当以SalenRu(Ⅲ)(PPh_3)X为催化剂,PTAT为共催化剂,反应温度在343K时,不同的环氧化合物可以较高的收率得到环碳酸酯。
4.合成了一系列双功能单分子有机盐SalenCo(Ⅲ)X催化剂,该催化剂同时具有Lewis酸和Lewis碱中心,可以实现二氧化碳与环氧化合物的动力学拆分,以高收率和中等ee值得到碳酸丙烯酯。考察了不同的抗衡离子、阴离子、阳离子、金属离子等对动力学拆分的影响。这种新颖的催化剂循环使用5次以后,产率和光学选择性没有明显的降低。
5.研究了SalenCo(Ⅲ)X/四丁基溴化铵(TBAB)体系中,不同氨基酸衍生物作为抗衡离子对催化剂催化性能以及拆分能力的影响。并且考察了不同手性有机酸盐作为共催化剂对于动力学拆分的影响。研究结果表明,在加入β环糊精(β-CD),得到的碳酸丙烯酯的ee值有了明显的提高。在优化的条件下考察了SalenCo(Ⅲ)X/手性共催化剂/β-CD催化体系对二氧化碳与环氧化合物动力学拆分的影响。
The coupling reaction of carbon dioxide and epoxides was well reviewed.And the orientation of developing efficient,simple and recyclable catalyst systems was determined.Meanwhile,new chiral catalyst systems based on a bifunctional catalyst in one molecule were synthesized and developed for the catalytic kinetic resolution of racemic epoxides with carbon dioxide to generate chiral cyclic carbonates.The contents are as follows:
1.We have synthesized several quaternary onium tribromides(3 new compounds) based on the traditional organic salts and firstly applied to catalyze the coupling reaction of carbon dioxide and epoxides.Phenyltrimethyl ammonium tribromide (PTAT)was the best catalyst,which combined with the metal compounds SalenCoX and developed to catalyze the coupling reaction of carbon dioxide and epoxides generating relevant cyclic carbonates including chiral propylene carbonate under mild conditions.The chiral propylene carbonate obtained 44.7%ee at 0℃.
2.A simple catalyst system of ZnBr_2-quaternary onium tribromide salt has been developed for the coupling reaction of carbon dioxide and epoxides.The effects of metal salts and reaction conditions and the recyclability of the catalysts were investigated.The results demonstrated that the coupling reaction of CO_2 and epoxides to form cyclic carbonates with high yield proceeds very effectively at 413K under 1.0MPa by using ZnBr_2 in conjunction with the PTAT co-catalyst without solvent.The catalyst could be recycled several times,which is of great prospect in industrial applications.
3.The coupling reaction of epoxides with carbon dioxide catalyzed by SalenRu(Ⅱ)(PPh_3)_2 or SalenRu(Ⅲ)X was studied.Reaction conditions were optimized. The new catalyst system of Salen-Ru(Ⅱ)(PPh_3)_2/PTAT promoted by ethyl diazoacetate(EDA)is able to catalyzed the coupling reaction,and the catalyst system of Salen-Ru(Ⅲ)(PPh_3)/PTAT is very efficient to catalyze synthesis of cyclic carbonate from various epoxides and carbon dioxide at 343K.
4.New chiral catalyst systems based on a bifunctional catalyst in one molecule were synthesized and developed for the catalytic kinetic resolution of racemic epoxides with carbon dioxide to generate chiral cyclic carbonates with high yield and moderate enantioselectivity.The effect of counterion,anion and cation of quaternary salt and metal center were investigated.These new catalysts have a great advantage being recycled easily at least 5 times without obviously lose of their activity and enantioselectivity.
5.In the chiral catalyst system SalenCoX/tetrabutylammonium bromide(TBAB), we investigated the effect of counterion and different chiral co-catalysts to catalyst activity and resolution,which based on the amino acid derivatives.When addingβCD, the enantioselectivity was increased obviously.Under the optimized conditions,we investigated the catalyst system of SalenCoX/chiral co-catalyst/βCD to resolution propylene oxide with carbon dioxide.
1.在传统的有机盐的基础上,成功地合成了一系列的季翁三溴盐(其中3个为新合成),并首次将其单独用于催化二氧化碳和环氧化合物的偶联反应,表现出较好的催化活性。当其与SalenCoX共同组成双功能催化体系。在温和的条件下(室温、100psi)可以高效地实现偶联反应,其中当共催化剂为苯基三甲基三溴化铵(PTAT)时,催化效果最好,可适合于各种末端取代的环氧化合物。并且在0℃实现了二氧化碳与环氧丙烷的动力学拆分,得到44.7%e.e.值的手性环碳酸酯。
2.开发了溴化锌-季鎓三溴盐简单催化体系催化二氧化碳和环氧化合物偶联反应,考察了反应温度、压力和不同金属盐对反应的影响以及催化剂的循环使用性能。结果表明,在413K和1.0MPa条件下,以溴化锌为催化剂,PTAT为共催化剂,无需加入任何溶剂就可以使二氧化碳和环氧化合物发生偶联反应,并以很高的收率得到环碳酸酯;并且催化剂实现了多次循环,具有工业应用价值。
3.研究了SalenRu(Ⅱ)(PPh_3)_2/SalenRu(Ⅲ)X催化二氧化碳与环氧化合物的偶联反应,考察了不同催化剂、共催化剂、助催化剂、反应温度以及不同的共催化剂对二氧化碳与环氧化合物偶联反应的影响。结果表明,当以SalenRu(Ⅱ)(PPh_3)_2为催化剂,重氮乙酸乙酯(EDA)为助催化剂,PTAT为共催化剂可以实现反应的转化;当以SalenRu(Ⅲ)(PPh_3)X为催化剂,PTAT为共催化剂,反应温度在343K时,不同的环氧化合物可以较高的收率得到环碳酸酯。
4.合成了一系列双功能单分子有机盐SalenCo(Ⅲ)X催化剂,该催化剂同时具有Lewis酸和Lewis碱中心,可以实现二氧化碳与环氧化合物的动力学拆分,以高收率和中等ee值得到碳酸丙烯酯。考察了不同的抗衡离子、阴离子、阳离子、金属离子等对动力学拆分的影响。这种新颖的催化剂循环使用5次以后,产率和光学选择性没有明显的降低。
5.研究了SalenCo(Ⅲ)X/四丁基溴化铵(TBAB)体系中,不同氨基酸衍生物作为抗衡离子对催化剂催化性能以及拆分能力的影响。并且考察了不同手性有机酸盐作为共催化剂对于动力学拆分的影响。研究结果表明,在加入β环糊精(β-CD),得到的碳酸丙烯酯的ee值有了明显的提高。在优化的条件下考察了SalenCo(Ⅲ)X/手性共催化剂/β-CD催化体系对二氧化碳与环氧化合物动力学拆分的影响。
The coupling reaction of carbon dioxide and epoxides was well reviewed.And the orientation of developing efficient,simple and recyclable catalyst systems was determined.Meanwhile,new chiral catalyst systems based on a bifunctional catalyst in one molecule were synthesized and developed for the catalytic kinetic resolution of racemic epoxides with carbon dioxide to generate chiral cyclic carbonates.The contents are as follows:
1.We have synthesized several quaternary onium tribromides(3 new compounds) based on the traditional organic salts and firstly applied to catalyze the coupling reaction of carbon dioxide and epoxides.Phenyltrimethyl ammonium tribromide (PTAT)was the best catalyst,which combined with the metal compounds SalenCoX and developed to catalyze the coupling reaction of carbon dioxide and epoxides generating relevant cyclic carbonates including chiral propylene carbonate under mild conditions.The chiral propylene carbonate obtained 44.7%ee at 0℃.
2.A simple catalyst system of ZnBr_2-quaternary onium tribromide salt has been developed for the coupling reaction of carbon dioxide and epoxides.The effects of metal salts and reaction conditions and the recyclability of the catalysts were investigated.The results demonstrated that the coupling reaction of CO_2 and epoxides to form cyclic carbonates with high yield proceeds very effectively at 413K under 1.0MPa by using ZnBr_2 in conjunction with the PTAT co-catalyst without solvent.The catalyst could be recycled several times,which is of great prospect in industrial applications.
3.The coupling reaction of epoxides with carbon dioxide catalyzed by SalenRu(Ⅱ)(PPh_3)_2 or SalenRu(Ⅲ)X was studied.Reaction conditions were optimized. The new catalyst system of Salen-Ru(Ⅱ)(PPh_3)_2/PTAT promoted by ethyl diazoacetate(EDA)is able to catalyzed the coupling reaction,and the catalyst system of Salen-Ru(Ⅲ)(PPh_3)/PTAT is very efficient to catalyze synthesis of cyclic carbonate from various epoxides and carbon dioxide at 343K.
4.New chiral catalyst systems based on a bifunctional catalyst in one molecule were synthesized and developed for the catalytic kinetic resolution of racemic epoxides with carbon dioxide to generate chiral cyclic carbonates with high yield and moderate enantioselectivity.The effect of counterion,anion and cation of quaternary salt and metal center were investigated.These new catalysts have a great advantage being recycled easily at least 5 times without obviously lose of their activity and enantioselectivity.
5.In the chiral catalyst system SalenCoX/tetrabutylammonium bromide(TBAB), we investigated the effect of counterion and different chiral co-catalysts to catalyst activity and resolution,which based on the amino acid derivatives.When addingβCD, the enantioselectivity was increased obviously.Under the optimized conditions,we investigated the catalyst system of SalenCoX/chiral co-catalyst/βCD to resolution propylene oxide with carbon dioxide.
引文
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