CN112159387B - 一种金属配位离子液体催化合成环状碳酸酯的方法 - Google Patents

一种金属配位离子液体催化合成环状碳酸酯的方法 Download PDF

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CN112159387B
CN112159387B CN202010973143.6A CN202010973143A CN112159387B CN 112159387 B CN112159387 B CN 112159387B CN 202010973143 A CN202010973143 A CN 202010973143A CN 112159387 B CN112159387 B CN 112159387B
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张香平
孟祥磊
刘莹
张晓春
张锁江
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Abstract

本发明涉及一种金属配位型离子液体催化CO2和环氧化物制备环状碳酸酯的方法，其特征在于使用金属配位型离子液体作为催化剂，催化剂用量为环氧化物的1.0～10.0mol％,在反应压力为0.1～20.0bar,反应温度为20～150℃，反应时间为0.25～12h的条件下催化环氧化物和二氧化碳环加成制备相应的环状碳酸酯。该法可在室温和常压的反应条件下表现出高效的催化活性，无需额外助催化剂和其他溶剂添加，且可实现催化剂多次循环使用。

Description

一种金属配位离子液体催化合成环状碳酸酯的方法
技术领域
本发明涉及CO2资源化利用的绿色清洁催化技术领域，具体指一种金属配位离子液体催化剂，催化 CO2和环氧化物环加成反应合成环状碳酸酯的方法。
背景技术
二氧化碳(CO2)是温室气体的主要成分，同时二氧化碳也是一种资源丰富、廉价易得的可再生C1资源。因此CO2的化学转化一直是国际学术界乃至工业上的热门问题。但是，其固有的强热力学稳定性，容易导致低反应活性和高能量输入，从而限制了CO2转化利用。其中一种有效的策略是通过CO2和环氧化物环加成制备五元环状碳酸酯产物。
催化CO2和环氧化物制备环状碳酸酯的关键问题在于CO2和环氧化物的活化上。目前大量的催化体系被开发出来催化活化CO2和环氧化物合成碳酸酯产品，包括含金属的配合物、有机金属材料、有机盐、碱金属和离子液体等。然而，报道的催化体系通常反应条件苛刻，需要高温(大于120℃)或高压(大于2MPa)，且需要添加额外助催化剂，这不仅造成了相对较高的能量输入和生产成本，同时增加了危险系数，不利于工业化应用。目前一些报道可以在相对比较温和的反应条件下催化环氧化物和CO2制备环状碳酸酯。天津大学何良年课题组使用Salen金属配合物和季铵盐作为催化剂，可在常压150℃的、条件下高效制备环状碳酸酯(中国专利CN104496959A)。太原理工大学发明了一种氨基功能化离子液体为活性组分，并添加四丁基溴化铵为助催剂的二元体系催化剂，能在常压和90℃的条件下反应36h得到90％碳酸丙烯酯的产率 (中国专利CN106732770A)。故本发明提供了一种以廉价易得含量丰富的金属元素为原料设计合成金属配位离子液体催化剂，并可在30℃、常压的条件下反应6h得到91％的环状碳酸酯，本发明催化剂廉价易得、催化效率高，具有很好的工业化应用前景。
发明内容
本发明研究使用金属配位离子液体催化剂，在温和反应氛围、无任何溶剂和助催化剂添加的条件下，实现高效催化二氧化碳和环氧化物合成环状碳酸酯的方法。
本反应的通式为：
Figure RE-GDA0002788434830000011
当R2表示H时，通式中所用环氧化物的结构为：
Figure RE-GDA0002788434830000012
中的一种，其中n＝0-6,X＝Cl,Br。当R2不为H时，所用环氧化物的结构为：
Figure RE-GDA0002788434830000021
本发明涉及一种金属配位型离子液体催化CO2和环氧化物制备环状碳酸酯的方法，其特征在于使用金属配位型离子液体作为催化剂，催化剂用量为环氧化物的1.0-10.0mol％,在反应压力为0.1-20.0bar,反应温度为20-150℃，反应时间为0.25-12h的条件下催化环氧化物和二氧化碳环加成制备相应的环状碳酸酯。该法可在室温和常压的反应条件下显示高效的催化活性，无需额外的助催化剂及溶剂的添加，且催化剂可多次循环使用。
本发明通过以下实施例说明，但并不限于实施例涉及范围，在不脱离前后所述宗旨的范围下，变化或更改实施例中反应技术参数，均包括在本发明的技术范围内。
具体实施方式
实施例1金属配位型离子液体催化剂的合成
本发明涉及的金属配位型离子液体的结构为
Figure RE-GDA0002788434830000022
中的一种，其中X为Cl,Br,I中的任意一种。M为Al,Zn,Cu,Mg中的任意一种。
所用金属配位离子液体的合成范例如下：
Figure RE-GDA0002788434830000023
首先，将0.02mol的氢氧化铝与0.03mol的3-溴丙酸加入到去离子水溶液中，加热至回流，搅拌保持回流24h，反应结束后冷却至室温，过滤除去过量未反应氢氧化铝，混合液经减压蒸馏，除去多余水分，得到黄色液体，得到的溶液中加入乙酸乙酯，滴加足量1,8-二氮杂二环十一碳-7-烯(DBU)，并不断搅拌，有固体产物析出，反应结束后，得到的固体物质用乙酸乙酯洗涤三次以上，50℃干燥24h即可得到金属铝配位离子液体。
实施例2催化二氧化碳和环氧化合物合成环状碳酸酯
Figure RE-GDA0002788434830000031
在20mL Schlenk管中，依次加入0.5mL环氧氯丙烷(1a)和4％mol合成范例中所示金属配位离子液体，磁力搅拌至金属配位离子液体全部溶解，由控温仪控制温度稳定至50℃,将充满二氧化碳的球胆连接至 Schlenk管，通入CO2，反应6小时后，冷却至室温，二氧化碳球胆取下备用，所得液体混合液以CDCl3作溶剂，在核磁光谱表征产物的产率，产品2a的选择性大于99％，产率为99％。
实施例3
同实施案例2，所用反应温度30℃反应时间6h，其他反应条件不变，得到产物2b的产率为91％。
实施例4
同实施案例2，所用反应温度25℃反应时间6h，其他反应条件不变，得到产物2b的产率为83％。
实施例5
同实施案例2，所用催化剂用量为环氧氯丙烷量的5mol％，反应温度30℃，反应时间2h，其他反应条件不变，得到产物2b的产率为68％。
实施例6
同实施案例2，所用催化剂用量为环氧氯丙烷量的5mol％，反应温度50℃，反应时间2h，其他反应条件不变，得到产物2b的产率为90％。
实施例7
同实施案例2，所用催化剂用量为环氧氯丙烷量的5mol％，反应温度25℃，反应时间2h，其他反应条件不变，得到产物2b的产率为58％。
实施例8
Figure RE-GDA0002788434830000032
同实施案例2，所用环氧化物为环氧溴丙烷(1b)，所用金属配位离子液体催化剂用量为环氧溴丙烷的 5mol％，反应时间5h，其他反应条件不变，得到产物2b的产率为99％。
实施例9
Figure RE-GDA0002788434830000041
同实施案例8，所用环氧化物为环氧丙烷丁基醚(1c)，其他反应条件不变，得到产物2c的产率为95％。
实施例10
Figure RE-GDA0002788434830000042
同实施案例8，所用环氧化物为1-烯丙氧基-2,3-环氧丙烷(1d)，其他反应条件不变，得到产物2d的产率为99％。
实施例11
Figure RE-GDA0002788434830000043
同实施案例8，所用环氧化物为氧化苯乙烯(1e)，其他反应条件不变，得到产物2e的产率为95％。
实施例12
Figure RE-GDA0002788434830000044
同实施案例8，所用环氧化物为苯基缩水甘油醚(1f)，其他反应条件不变，得到产物2f的产率为96％。
实施例13
Figure RE-GDA0002788434830000045
同实施案例8，所用环氧化物为苯基缩水甘油醚(1g)，其他反应条件不变，得到产物2g的产率为97％。
实施例14
Figure RE-GDA0002788434830000051
同实施案例8，所用环氧化物为环氧环己烷(1h)，其他反应条件不变，得到产物2h的产率为72％。
实施例15催化剂循环稳定性
Figure RE-GDA0002788434830000052
对金属配位离子液体循环利用效果进行考察。反应条件同实施案例12，反应后通过添加去离子水分相，回收金属配位离子液体，其他反应条件不变，循环四次得到产物2f的产率为96％，95％，95％，94％，结果显示反应4次后没有显著降低。
尽管上述内容已经用-般性说明及具体实施方案对本发明作了详尽的描述，但在本发明的基础上，所属领域的技术人员可以对之作的一些修改或改进，均是本领域显而易见的。因此，在不偏离本发明精神的基础上所做的修改或改进，均属于本发明要求保护范围。

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1.一种金属配位离子液体催化制备环状碳酸酯的方法，其特征在于使用环氧化物和二氧化碳作为反应物，催化剂选自金属配位离子液体中的一种，催化剂用量为环氧化物的0.1～10 mol％,在反应压力0.1～100bar,温度为20～50℃,反应时间0.25～12h条件下合成环状碳酸酯。所述金属配位离子液体结构选自以下：
Figure FDA0003028701630000011
其中金属离子液体的n为1-4的整数，X为Cl、Br、I卤素基团中的任意一种，M为1/3Al。所述环氧化物结构为：
Figure FDA0003028701630000012
其中环氧化物的n为0-6的自然数，X为Cl、Br。
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