Study on catalytic properties of novel ether-based perrhenate ionic liquids

doi:10.11949/0438-1157.20191367

Abstract

Abstract:

Two novel ether-based perrhenate ionic liquids 1-(2-methoxyethyl)-3-ethylimidazolium perrhenate ([C₂2O1Im][ReO₄]) and1-(2-ethoxyethyl)-3-ethylimidazolium perrhenate ([C₂2O2Im][ReO₄]) were synthesized and characterized by nuclear magnetic resonance spectroscopy (¹H NMR,¹³C NMR), Raman spectroscopy (Raman), electrospray ionization mass spectrometry (ESI-MS), differential scanning calorimetry (DSC). As a sort of organic synthesis intermediates which is chemically active and easily converted into other substances, epoxy compounds occupy an extremely important position in various industries of national production. The epoxidation of olefins is an important way to synthesize epoxy compounds. Therefore, two novel ether-based perrhenate ionic liquids were used as catalyst and solvent in the reaction system of cyclooctene epoxidation to epoxycyclooctane, respectively. The effects of reaction temperature, time, oxidant amount, catalyst amount and its recycle were investigated systematically. The results showed that the yield was more than 90%, the reaction selectivity was more than 99%, the catalyst was cycled 5 times, and the yield did not decrease significantly.

Key words: ether group, perrhenate ionic liquids, homogeneous catalysis, epoxidation, selectivity

摘要：

自合成两种新型醚基高铼酸盐离子液体：1-(2-甲氧基乙基)-3-乙基咪唑高铼酸盐（[C₂2O1Im][ReO₄]）和1-(2-乙氧基乙基)-3-乙基咪唑高铼酸盐（[C₂2O2Im][ReO₄]），并利用核磁共振氢谱/碳谱、拉曼光谱、质谱和差示扫描量热等方法表征，确定是目标产物。环氧化合物是一种化学性质活泼且易转化为其他物质的有机合成中间体，烯烃的环氧化反应是合成环氧化合物的一种重要途径，因此建立以新型醚基高铼酸盐离子液体为溶剂兼催化剂的环辛烯环氧化均相反应体系，系统研究反应温度、时间、氧化剂用量、催化剂用量及循环使用等因素的影响。结果表明，产率大于90%，反应选择性大于99%，催化剂循环5次，产率无明显下降。

关键词: 醚基, 铼离子液体, 均相催化, 环氧化, 选择性

CLC Number:

TQ 028.8

Xiaoxue MA, Kunhao LIANG, Jie WEI, Zongren SONG, Chuanyou XIAO, Lu GONG, Dawei FANG. Study on catalytic properties of novel ether-based perrhenate ionic liquids[J]. CIESC Journal, 2020, 71(1): 314-319.

马晓雪, 梁坤豪, 魏杰, 宋宗仁, 肖传佑, 巩璐, 房大维. 醚基高铼酸盐离子液体的催化性能研究[J]. 化工学报, 2020, 71(1): 314-319.

Figures/Tables 7

Fig.1 Synthetic route of ionic liquids [C22O1Im][ReO4] and [C22O2Im][ReO4]

Fig.2 Epoxidation of cyclooctene catalyzed by ionic liquids [C22O1Im][ReO4] and [C22O2Im][ReO4]

Fig.3 Effect of amount of catalyst on catalytic yield

Fig.4 Effect of reaction time on catalytic yield

Fig.5 Effect of reaction temperature on catalytic yield

Fig.6 Effect of amount of oxidant urea peroxide on catalytic yield

Fig.7 Effect of cycle times of ionic liquid on catalytic yield

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