5-异氰酸酯-异肽酰氯的合成.pdf

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化工进展
184
CHEMICAL INDUSTRY AND ENGINEERING PROGRESS
2013年第32卷第1期
研究开发
5-异氰酸酯异肽酰氯的合成
刘立芬-,徐德志,陈欢林2,高从堦23
(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
摘要:5-异氣酸酷一异酞酰氯(ICIC)作为一种关键功能单体可用于制备耐污染的聚酰胺一脲复合反渗透膜。
采用反加料方式,以5-氪基-异酞酸为基本原料,在催化剂作用下与酖氟化剂三光气(BTC)反应得到中间体
氯甲酰胺基-异酞酰,再经回流得产品ICIC。对合成エ艺如加料方式、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剂组合。此外,朱用红外光语(IR)
氢核磁(HNMR)和质谱(MS)分析了产品的化学结构。
关键词:5-异氰酸酯-一异酞酰;反加料方式;三光气;复合催化剂;溶剂组合
中图分类号:O6
文献标志码:A文章编号:1000-6613(2013)01-0184-05
DOl:10.3969 J. issn.1000-6613.2013.01.031
Synthesis of 5-isocyanato-isop hthaloyl chloride
LTU Lifen", XU Dezhi, CHEN Huanlin, GAO Congjie
(State Kcy Laboratory Breeding Base of Green Chemistry-synthesis Technology, Zhejiang University of Technology,
310027, Zhejiang, China; Development enter of water Treatment Technology, Hangzhou 310012, Zhejian, C
Hangzhou 310014, Zhejiang, China; "Department of Chemical and Biological Engineering, Zhejiang University, Hangzho
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(R), hydrogen nuclear magnetic resonance(HNMR
and mass spectragraph(MS)
Key words: 5-isocyanato-isophthaloyl chloride; reverse adding mode; triphosgene; composite catalyst
solvent combination
收稿日期:2012-07-20。修改稿日期:2012-08-01。
5-异氧酸-异酞酰氯(5- Isocyanato- isophthaloyl基金项目:国家自然科学基金(2100及因家973计划
chloride)简称ICIC,也称为3,5-二酰氯基苯异氰酸
(2009CB623402)项目。
第一作者及联系人:刘立芬(1975),女,副研究员,硕士生导师,
酯或3,5-二甲兟氯基-异氰酸酯。ICC是新型的三官主要从事膜分离技术的研究。E-maillifenliu(@zjut.edu.cn