CN112480059A - 一种金属卟啉催化烯烃直接合成环碳酸酯的方法 - Google Patents

一种金属卟啉催化烯烃直接合成环碳酸酯的方法 Download PDF

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CN112480059A
CN112480059A CN202011372914.2A CN202011372914A CN112480059A CN 112480059 A CN112480059 A CN 112480059A CN 202011372914 A CN202011372914 A CN 202011372914A CN 112480059 A CN112480059 A CN 112480059A
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metalloporphyrin
cyclic carbonate
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张治国
产圣
易敏
郑学根
陈静雯
杨森
鲍宗必
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China Petroleum and Chemical Corp
Zhejiang University ZJU
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Zhejiang University ZJU
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Abstract

本发明公开了一种金属卟啉催化烯烃直接合成环碳酸酯的方法，涉及催化合成技术领域，其技术方案包括：以金属卟啉为催化剂，离子液体为助催化剂，催化烯烃、二氧化碳和氧化剂进行环氧化羧化反应，一锅法制备环碳酸酯，具体反应方程为：
Figure DDA0002806646290000011
本发明反应条件温和，催化剂制备简便、催化剂用量少，并以高转化率和高选择性得到目标产物环碳酸酯。

Description

一种金属卟啉催化烯烃直接合成环碳酸酯的方法
技术领域
本发明涉及一种催化物合成技术领域，具体为一种环碳酸酯的合成方法。
背景技术
当前，关于烯烃与二氧化碳直接制备环碳酸酯的研究报道很少。现有技术中使用有机铑配合物催化烯烃在氧气中的环氧化反应，随后环氧化产物进一步与二氧化碳环加成生成环碳酸酯，该体系中环碳酸酯产率为20～30％(J.Mol.Catal.,1987,41,355-399)。随后，该研究小组使用一系列金属氧化物作催化剂，结果表明五氧化二铌具有较好的催化效果，以16.6％的产率得到相应的环碳酸酯(Organomel.Chem.,2000,14,779-802)。此外，其它金属盐、金属有机框架材料等也被开发用于催化烯烃与二氧化碳反应制备环碳酸酯，然而反应的转化率、选择性及经济性等仍无法满足实际生产需求。
当前报道的烯烃与二氧化碳直接合成环碳酸酯的收率<50％，无法满足工业生产要求。针对现有技术的不足，本发明目的在于提供一种可在温和条件下，直接由烯烃、氧化剂、二氧化碳通过环氧化羧化直接、高效地制备环碳酸酯的方法。达到简化操作步骤、降低催化剂用量，并以高收率和高选择性得到目标产物的目的。
发明内容
本发明的目的在于克服现有技术的不足，提供了一种金属卟啉催化烯烃直接合成环碳酸酯的方法，以解决现有技术中收率低等的技术问题。
本发明是通过以下技术方案实现的：
本发明提供了一种金属卟啉催化烯烃直接合成环碳酸酯的方法，该方法包括将烯烃、金属卟啉配合物以及助催化剂加入高压反应釜中，通入二氧化碳及氧气/空气，反应结束后获得目标产物。
其中，烯烃与二氧化碳和氧气经催化剂混合物催化反应生产环碳酸酯的反应式具体为：
Figure BDA0002806646270000011
烯烃与CO2一步制备环碳酸酯反应式。其中，式中R4、R5独自地选自氢、烷基、烷氧基、芳基、酯基；或R4、R5独自地选自烷基、烷氧基，且R4、R5与它们所连接的原子可形成环。
金属卟啉配合物的结构式为：
Figure BDA0002806646270000021
其中，四齿配位金属卟啉配合物meso位苯环上R1、R2、R3分别选自氢、卤素、脂肪族基团、取代的脂肪族基团、硝基或者氨基中的任意一种基团；
所述的X为卤基、-NO3、CH3COO-、-CO、CF3COO-、ClO4、-CN、-BF4中任意一种；所述的金属离子为Fe、Mn、Ru、Co中任意一种；
所述助催化剂具体为一系列基于吡啶及其衍生物和含氮有机碱的质子型和非质子型离子液体中一种，其化学结构参考图1。
进一步，金属卟啉配合物的用量与底物的摩尔比为0.01％～0.5％。
进一步，助催化剂的用量与金属卟啉配合物的用量的摩尔比为0.1～5:1。
进一步，氧气/空气的压力为0.1～5MPa，二氧化碳的压力为0.1～10MPa，高压反应釜内反应温度为25～150℃，反应时间为0.5～10h。
进一步，所述金属卟啉配合物具体为四苯基卟啉锰，所述助催化剂具体为[DMAPH]Br。
进一步，所述烯烃具体为1.2g苯乙烯，金属卟啉配合物用量为1mg，助催化剂用量为51mg，氧气压力为0.1MPa，二氧化碳压力为1.2MPa，反应时间为8h，反应温度为100℃。
本发明相比现有技术具有以下优点：本发明提供了一种金属卟啉催化烯烃直接合成环碳酸酯的方法，以价廉易得的烯烃及二氧化碳为原料，在温和的条件下制备环碳酸酯；将环氧化反应与环氧化物和CO2的环加成反应在一锅中进行，实现了过程集成，简化了反应体系，减少分离提纯步骤，降低能耗及生产成本；催化剂制备简便，反应转化率高，选择性好，容易实现工业化生产。
附图说明
图1为助催化剂化学结构示意图。
具体实施方式
下面将结合本发明实施例，对本发明的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
本实施例中合成环碳酸酯的具体反应式为：
Figure BDA0002806646270000031
具体的步骤为将末端烯烃、金属卟啉配合物催化剂以及助催化剂加入反应器中，通入二氧化碳及氧气/空气，反应温度为25～150℃，反应0.5～10h，其反应式为式1，为烯烃与CO2一步制备环碳酸酯反应式。其中，式中R4、R5独自地选自氢、烷基、烷氧基、芳基、酯基；或R4、R5独自地选自烷基、烷氧基，且R4、R5与它们所连接的原子可形成环。
金属卟啉配合物具有下式所示结构：
Figure BDA0002806646270000032
其中，四齿配位金属卟啉配合物meso位苯环上R1、R2、R3选自氢、卤素、脂肪族基团、取代的脂肪族基团、硝基或者氨基等基团；
所述的X为卤基、-NO3、CH3COO-、-CO、CF3COO-、ClO4、-CN、-BF4等；所述的金属离子为Fe、Mn、Ru、Co等；
本实施例中的反应在100mL高压反应釜中进行。向反应釜中加入烯烃、金属卟啉配合物、助催化剂，封闭反应釜，依次通入0.1～10MPa二氧化碳和0.1～5MPa氧气。在一定温度下搅拌反应0.5～10h，得到相应的环碳酸酯产物，产物采用气相色谱法测定其产品收率，以下实施例中金属卟啉配合物具体为四苯基卟啉锰，MnTPP。
实施例1
苯乙烯(1.2g,10mmol)、四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[4-Pr-PyH]Br a(40mg,0.25％mol)，0.1MPa氧气和1.2MPa二氧化碳，在80℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率为89％。
实施例2
苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[4-NH2-PyH]Br b(44mg,0.25％mol)，封闭反应釜，通入0.8MPa氧气和1.2MPa二氧化碳。在100℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率95％。
实施例3
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[4-OH-PyH]Br c(44mg,0.25％mol)，封闭反应釜，通入0.6MPa氧气和1.2MPa二氧化碳。在130℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率90％。
实施例4
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[PyH]Br d(57mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在90℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率88％。
实施例5
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[DMAPH]F e(36mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在150℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率86％。
实施例6
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[DMAPH]Cl f(40mg,0.25％mol)，封闭反应釜，通入0.5MPa氧气和2MPa二氧化碳。在120℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率95％。
实施例7
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[DMAPH]Br g(51mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在100℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率96％。
实施例8
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[DBUH]Cl h(47mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在90℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率87％。
实施例9
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(1.0mg,0.14％mmol)，助催化剂[DBUH]Br i(58mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在120℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率89％。
实施例10
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(2.0mg,2％mmol)，助催化剂[DABCOH]Br j(48mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在25℃反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率78％。
实施例11
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉锰(2.0mg,2％mmol)，助催化剂[HMIM]Br k(41mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在60℃下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率79％。
实施例12
在100mL的高压反应釜中，加入苯乙烯(1.2g,10mmol)，四苯基卟啉氯化锰(2.0mg,2％mmol)，助催化剂[DMAPH]Br g(51mg,0.25％mol)，封闭反应釜，通入0.1MPa氧气和1.2MPa二氧化碳。在一定温度下反应8h，停止反应，得到相应的环碳酸酯，经气相检测其产率78％。
通过上述实施例1-12可知，本发明提供的反应原理能够有效的制备环碳酸酯，同时其收率可观，且本发明以价廉易得的烯烃和二氧化碳为原料，制备过程简单，生产成本低，制备的环碳酸酯纯度大。
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等，均应包含在本发明的保护范围之内。

Claims (6)

1.一种金属卟啉催化烯烃直接合成环碳酸酯的方法，其特征在于，该方法包括将烯烃、金属卟啉配合物以及助催化剂加入高压反应釜中，通入二氧化碳及氧气/空气，反应结束后获得目标产物，金属卟啉配合物的结构式为：
Figure FDA0002806646260000011
其中，四齿配位金属卟啉配合物meso位苯环上R1、R2、R3分别选自氢、卤素、脂肪族基团、取代的脂肪族基团、硝基或者氨基中的任意一种基团；
所述的X为卤基、-NO3、CH3COO-、-CO、CF3COO-、ClO4、-CN、-BF4中任意一种；所述的金属离子为Fe、Mn、Ru、Co中任意一种；
所述助催化剂具体为一系列基于吡啶及其衍生物和含氮有机碱的质子型和非质子型离子液体中一种。
2.根据权利要求1所述的一种金属卟啉催化烯烃直接合成环碳酸酯的方法，其特征在于，金属卟啉配合物的用量与底物的摩尔比为0.01％～0.5％。
3.根据权利要求2所述的一种金属卟啉催化烯烃直接合成环碳酸酯的方法，其特征在于，助催化剂的用量与金属卟啉配合物的用量的摩尔比为0.1～5:1。
4.根据权利要求3所述的一种金属卟啉催化烯烃直接合成环碳酸酯的方法，其特征在于，氧气/空气的压力为0.1～5MPa，二氧化碳的压力为0.1～10MPa，高压反应釜内反应温度为25～150℃，反应时间为0.5～10h。
5.根据权利要求4所述的一种金属卟啉催化烯烃直接合成环碳酸酯的方法，其特征在于，所述金属卟啉配合物具体为四苯基卟啉锰，所述助催化剂具体为[DMAPH]Br。
6.根据权利要求5所述的一种金属卟啉催化烯烃直接合成环碳酸酯的方法，其特征在于，所述烯烃具体为1.2g苯乙烯，金属卟啉配合物用量为1mg，助催化剂用量为51mg，氧气压力为0.1MPa，二氧化碳压力为1.2MPa，反应时间为8h，反应温度为100℃。
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Publication number Priority date Publication date Assignee Title
CN114950545A (zh) * 2022-03-28 2022-08-30 浙江恒逸石化研究院有限公司 一种用于乙醛偶姻缩合反应的噁唑盐催化剂及其制备方法和应用

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114950545A (zh) * 2022-03-28 2022-08-30 浙江恒逸石化研究院有限公司 一种用于乙醛偶姻缩合反应的噁唑盐催化剂及其制备方法和应用
CN114950545B (zh) * 2022-03-28 2024-06-07 浙江恒逸石化研究院有限公司 一种用于乙醛偶姻缩合反应的噁唑盐催化剂及其制备方法和应用

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