5-异氰酸酯-异肽酰氯的合成

化工进展

5-异氰酸酯-异肽酰氯的合成

刘立芬1,2，徐德志1，陈欢林2，高从堦2,3

1浙江工业大学绿色化学合成技术国家重点实验室培育基地，浙江杭州 310014；2浙江大学化学工程与生物工程学系，浙江杭州 310027； 3杭州水处理技术研究开发中心有限公司，浙江杭州 310012

出版日期:2013-01-05 发布日期:2013-01-25

Synthesis of 5-isocyanato-isophthaloyl chloride

LIU Lifen1,2, XU Dezhi1, CHEN Huanlin2, GAO Congjie2,3

1State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, Zhejiang, China; 2Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China; 3Development Center of Water Treatment Technology, Hangzhou 310012, Zhejiang, China

Online:2013-01-05 Published:2013-01-25

摘要/Abstract

摘要： 5-异氰酸酯-异酞酰氯（ICIC）作为一种关键功能单体可用于制备耐污染的聚酰胺-脲复合反渗透膜。采用反加料方式，以5-氨基-异酞酸为基本原料，在催化剂作用下与酰氯化剂三光气（BTC）反应得到中间体5-氯甲酰胺基-异酞酰氯，再经回流得产品ICIC。对合成工艺如加料方式、催化剂组成及溶剂组合进行了优化，并分析了反应机理。研究结果表明，反加料方式是确保反应顺利进行的首要条件，复合催化剂三乙胺（TEA）/咪唑（Imidazole）的催化效果最佳，而四氢呋喃/氯苯则是反应最理想的溶剂组合。此外，采用红外光谱（IR）、氢核磁（1HNMR）和质谱（MS）分析了产品的化学结构。

关键词: 5-异氰酸酯-异酞酰氯, 反加料方式, 三光气, 复合催化剂, 溶剂组合

Abstract: 5-Isocyanato-isophthaloyl chloride（ICIC）as a key functional monomer can be used to prepare the antifouling polyamide-urea RO membrane by interfacial polymerization. In this study, ICIC was synthesized with carbonyl chlorinating reagent of triphosgene (BTC). The substrate 5-amido-isophthalio acid reacted with BTC in the presence of composite catalyst to get the intermediate 5-chloride formylamine-isophthaloyl, then the resulting intermediate was refluxed to obtain the final product ICIC. The synthesis parameters, such as adding mode of substrate, catalyst composition and solvent combination were optimized, and the reaction mechanism was proposed. The results showed that the reverse adding mode was the primary condition of driving the reaction. It was also demonstrated that the composite catalyst of TEA/imdazole had the best catalysis performace, and THF/chlorobenzene was the optimum solvent combination. Furthermore, the chemical structure of product ICIC was identified via infrared spectra (IR), hydrogen nuclear magnetic resonance (1HNMR) and mass spectragraph (MS).

Key words: 5-isocyanato-isophthaloyl chloride, reverse adding mode, triphosgene, composite catalyst, solvent combination

刘立芬1,2，徐德志1，陈欢林2，高从堦2,3. 5-异氰酸酯-异肽酰氯的合成[J]. 化工进展.

LIU Lifen1,2, XU Dezhi1, CHEN Huanlin2, GAO Congjie2,3. Synthesis of 5-isocyanato-isophthaloyl chloride[J]. Chemical Industry and Engineering Progree.

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