CN112409190A - 胺盐类离子液体高效催化合成环状碳酸酯的方法 - Google Patents

胺盐类离子液体高效催化合成环状碳酸酯的方法 Download PDF

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CN112409190A
CN112409190A CN202011221353.6A CN202011221353A CN112409190A CN 112409190 A CN112409190 A CN 112409190A CN 202011221353 A CN202011221353 A CN 202011221353A CN 112409190 A CN112409190 A CN 112409190A
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张敬来
王丽
任铁钢
刘昉
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Abstract

本发明提供了一种胺盐类离子液体催化合成环状碳酸酯的方法，其以二氧化碳和环氧化合物为底物，在反应压力为0.1‑0.5MPa，温度30℃‑60℃，反应时间1‑10小时条件下制备环状碳酸酯的。该反应所使用的催化剂是酸碱反应的产物‑‑‑一种胺盐类离子液体，该离子液体备受青睐主要是因为它具有易于制备、原料成本低廉、绿色环保、催化剂活性高等优点。需要指出的是，在50℃相当温和的条件下，加入少量的离子液体催化剂，环状碳酸酯的收率可达99%以上。

Description

胺盐类离子液体高效催化合成环状碳酸酯的方法
技术领域
本发明属于环状碳酸酯合成技术领域，具体涉及由一种新型的胺盐类离子液体作为催化剂，通过环加成反应高效催化合成环状碳酸酯的方法。
背景技术
CO2的过量排放会引起温室效应，温室效应将会造成全球变暖、海平面上升、气候反常等一系列环境问题。但同时它又是一种廉价丰富、无毒、可持续使用的C1资源。目前，每年有一亿吨以上的CO2被转化利用，较为成熟的产品有尿素、水杨酸、甲醇、环状碳酸酯和聚碳酸酯。这对改善环境、从绿色可持续角度来说具有重大的意义。在众多的CO2转化利用途径中，CO2与环氧化合物的环加成反应是一种最有效且被广泛利用的方法，一方面是其具有原子经济型的特点，副产物可以忽略不计，另一方面生成的环状碳酸酯应用广泛。它是生产聚合物和精细化学品的重要中间体。此外，环状碳酸酯也可以直接用作有机合成中的良好极性溶剂，或作为锂电池中的液体电解质。
由于环状碳酸酯具有巨大的市场需求和广泛的应用前景，因此需要探索出活性较高的催化剂以提高环状碳酸酯的产率。目前已报道出各种不同的均相和非均相催化剂用于CO2和环氧化合物的环加成反应，包括MOF、金属-salen配合物和金属卟啉化合物。它们在温和反应条件下表现出良好的反应活性，但其毒性大、合成工艺复杂、成本较高，而胺盐类离子液体以其独特的优势在众多催化剂中脱颖而出。近十年来，各种离子液体得到了长足的发展，功能化离子液体、双阳离子型离子液体、双功能化离子液体等层出不穷，但在没有金属助催化剂或有机溶剂的条件下，一般离子液体仍可能具有合成困难、不够环保、经济性差、催化活性低中的一个或多个缺点。因此，在温和条件下探索无毒无害、成本较低且具有高催化活性的高效离子液体是十分必要的。
发明内容
本发明针对现有环状碳酸酯合成方法存在的反应条件较为苛刻、催化剂合成复杂且催化剂活性较低，以及不够环保、成本较高等问题，探索出一种在温和条件下、以新型的胺盐类离子液体作为催化剂，通过环加成反应高效催化合成环状碳酸酯的新方法。
本发明提供了一种胺盐类离子液体，所述胺盐类离子液体的结构如下述任一所示：
Figure BDA0002762126010000011
本发明还提供了利用上述胺盐类离子液体催化合成环状碳酸酯的方法，具体为：将胺盐类离子液体与环氧化合物按(5-15)：100的摩尔比在反应釜内混合，保持反应釜密闭状态，通入二氧化碳使反应釜的压强在0.1-0.5MPa，然后在反应温度30-60℃条件下恒温恒压反应1-10小时，反应结束后，加入乙酸乙酯，产物溶于乙酸乙酯，而催化剂析出，产物经气相色谱分析，测得产物收率。
作为本发明的进一步优化，所述的环氧化合物结构可以为
Figure BDA0002762126010000021
Figure BDA0002762126010000022
进一步优选的，胺盐类离子液体与环氧化合物的摩尔比为15:100。
进一步优选的，所述的反应温度为50-60℃。
本发明方法以二氧化碳与环氧化合物为反应物，在反应压力为0.1-0.5MPa、温度30-60℃，反应时间1-10小时条件下通过环加成反应制备相应的环状碳酸酯，所使用的催化剂是酸碱反应的产物---胺盐类离子液体。和现有技术相比，本发明具有如下有益效果：
本发明方法值得称道的地方在于催化剂的创新性，它是通过酸碱反应制备的一种新型胺盐类离子液体，它的合成步骤较为简单，原料成本较低，并且催化活性高，重复利用五次后仍然具有良好的活性，是一种比较理想的催化剂。当反应温度为50℃时，仅仅加入很少量的离子液体催化剂就能达到意想不到的环状碳酸酯产率(99％)。根据以上叙述可以看出本发明方法具有很大的应用潜力，价值巨大，令人憧憬。
附图说明
图1是实施例1中制备的[BETMA+][-O2EEPZ+][Br-]催化剂的核磁共振氢谱；
图2是实施例1中制备的[BETMA+][-O2EEPZ+][Br-]催化剂的核磁共振碳谱；从图1和2中可以看出，合成的催化剂为目标催化剂。
具体实施方式
本发明所用的胺盐类离子液体催化剂合成方法用以下实施例说明，但以下实施例只用于说明本发明，并不是本发明的限定。
实施例1胺盐类离子液体的制备
将10mmol溴化羧乙基乙基吡唑盐(CEEPzBr)与10mmol苄基三甲基氢氧化铵放入50ml容量瓶中，再向其中加入5ml甲醇作为溶剂，在常温条件下反应12h，反应结束后经旋蒸(除去甲醇溶剂)、洗涤(20ml乙酸乙酯洗涤三次)、干燥(60℃真空干燥4h)得到纯净的离子液体[BETMA+][-O2EEPZ+][Br-]，其核磁共振氢谱图如图1所示，核磁共振碳谱图如图2所示，其结构如下所示：
Figure BDA0002762126010000031
参考上述方法，将苄基三甲基氢氧化铵替换为1,8-二氮杂二环十一碳-7-烯(DBU)，得到离子液体[DBUH+][-O2EEPZ+][Br-]；将溴化羧乙基乙基吡唑盐(CEEPzBr)替换为2,2,2-三氟乙醇(TFE)，得到离子液体[BETMA+][TFE-]；两离子液体的结构式分别为：
Figure BDA0002762126010000032
实施例2
取实施例1中的[BETMA+][-O2EEPZ+][Br-]催化剂0.75mmol放入50ml清洗干净的高压反应釜中，再向其中加入5mmol的环氧氯丙烷，催化剂占环氧氯丙烷摩尔含量为15mol％，密闭反应釜保持反应釜密闭状态，向其中缓慢通入CO2气体把反应釜内空气除净，最终把CO2压力稳定在0.1MPa，在50℃下反应6h,反应结束后，加入乙酸乙酯，产物溶于乙酸乙酯，而催化剂析出，产物经气相色谱分析，测得产物碳酸丙烯酯收率为99.3％，选择性＞99％。
实施例3
具体实验过程与检测方法同实施例2，区别仅在于所使用的催化剂为[DBUH+][-O2EEPZ+][Br-]，测得的产物收率为97.5％，选择性＞99％。
实施例4
具体实验过程与检测方法同实施例2，区别仅在于所使用的催化剂为[BETMA+][TFE-]，测得的产物收率为69.5％，选择性＞99％。
实施例5
具体实验过程与检测方法同实施例2，区别仅在于催化剂占环氧氯丙烷摩尔含量为5mol％，测得的产物收率为74.2％，选择性＞99％。
实施例6
具体实验过程与检测方法同实施例2，区别仅在于催化剂占环氧氯丙烷摩尔含量为7mol％，测得的产物收率为85.2％，选择性＞99％。
实施例7
具体实验过程与检测方法同实施例2，区别仅在于催化剂占环氧氯丙烷摩尔含量为10mol％，测得的产物收率为92.8％，选择性＞99％。
实施例8
具体实验过程与检测方法同实施例2，区别仅在于催化剂占环氧氯丙烷摩尔含量为12mol％，测得的产物收率为96.1％，选择性＞99％。
实施例9
具体实验过程与检测方法同实施例2，区别仅在于反应时间为1h，测得的产物收率为57.9％，选择性＞99％。
实施例10
具体实验过程与检测方法同实施例2，区别仅在于反应时间为2h，测得的产物收率为74.8％，选择性＞99％。
实施例11
具体实验过程与检测方法同实施例2，区别仅在于反应时间为3h，测得的产物收率为84.8％，选择性＞99％。
实施例12
具体实验过程与检测方法同实施例2，区别仅在于反应时间为4h，测得的产物收率为90.1％，选择性＞99％。
实施例13
具体实验过程与检测方法同实施例2，区别仅在于反应时间为5h，测得的产物收率为95.4％，选择性＞99％。
实施例14
具体实验过程与检测方法同实施例2，区别仅在于使用的环氧化合物为环氧丙烷，测得的产物收率为48.1％，选择性＞99％。
实施例15
具体实验过程与检测方法同实施例2，区别仅在于使用的环氧化合物为环氧丙醇，称重法测得的产物收率为57.7％，选择性＞99％。
称重法：将反应结束后的产物用甲醇溶解后从反应釜中取出，旋蒸后称得质量为m，使用的催化剂质量为m1，底物的质量为m2，产率的计算方法为
Figure BDA0002762126010000041
本实验反应方程式为：
Figure BDA0002762126010000042
实施例16
具体实验过程与检测方法同实施例2，区别仅在于使用的环氧化合物为苯基缩水甘油醚，反应温度为60℃，0.5MPa的CO2，反应时间为10h，称重法测得的产物收率为72.7％，选择性＞99％。
本实验反应方程式为：
Figure BDA0002762126010000051
实施例17
具体实验过程与检测方法同实施例2，区别仅在于使用的环氧化合物为氧化苯乙烯，反应温度为60℃，0.5MPa的CO2，反应时间为10h，测得的产物收率为85.2％，选择性＞99％。
本实验反应方程式为：
Figure BDA0002762126010000052
实施例18
具体实验过程与检测方法同实施例17，区别仅在于使用的环氧化合物为烯丙基缩水甘油醚，测得的产物收率为91.9％，选择性＞99％。
本实验反应方程式为：
Figure BDA0002762126010000053
实施例19
具体实验过程与检测方法同实施例17，区别仅在于使用的环氧化合物为环氧环己烷，测得的产物收率为20.5％，选择性＞99％。
本实验反应方程式为：
Figure BDA0002762126010000054
实施例21-25
具体实验过程与检测方法同实施例2，区别仅在于使用的催化剂为实施例2中回收的[BETMA+][-O2EEPZ+][Br-]催化剂，在相同条件下进行5次循环回收实验，所得结果见表1。
表1、实施例21-25催化剂回收使用催化结果
Figure BDA0002762126010000061
由表1可以看出，[BETMA+][-O2EEPZ+][Br-]循环使用2次后，催化产率只下降了0.5％，循环使用5次后，催化产率仍保持在91％以上，说明该催化剂具有良好的循环使用性能。
综上可以看出：反应所使用的催化剂是酸碱反应的产物---一种新型胺盐类离子液体，该离子液体具有易于制备、原料成本低廉、绿色环保、催化剂活性高等优点。在50℃相当温和的条件下，加入少量的离子液体催化剂，环状碳酸酯的收率可达99％以上。

Claims (5)

1.一种胺盐类离子液体，其特征在于，所述胺盐类离子液体的结构如下述任一所示：
Figure DEST_PATH_IMAGE001
、
Figure DEST_PATH_IMAGE002
。
2.权利要求1所述胺盐类离子液体催化合成环状碳酸酯的方法，其特征在于，将胺盐类离子液体与环氧化合物按（5-15）：100的摩尔比在反应釜内混合，通入二氧化碳使反应釜的压强在0.1-0.5MPa，然后在反应温度30-60℃条件下恒温恒压反应1-10小时，反应结束后经后处理即得。
3.根据权利要求2所述胺盐类离子液体催化合成环状碳酸酯的方法，其特征在于，所述的环氧化合物结构为
Figure DEST_PATH_IMAGE003
Figure DEST_PATH_IMAGE004
。
4.根据权利要求2或3所述胺盐类离子液体催化合成环状碳酸酯的方法，其特征在于，胺盐类离子液体与环氧化合物的摩尔比为15:100。
5.根据权利要求4所述胺盐类离子液体催化合成环状碳酸酯的方法，其特征在于，所述的反应温度为50-60℃。
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