欢迎访问《日用化学工业(中英文)》,今天是

日用化学工业 ›› 2021, Vol. 51 ›› Issue (4): 288-293.doi: 10.3969/j.issn.1001-1803.2021.04.004

• 开发与应用 • 上一篇    下一篇

短碳氟链缩合剂的绿色合成与应用

汪琴琴1(),李颜利1(),邹伟1,颜杰1,刘波2,李慧2   

  1. 1.四川轻化工大学 化学工程学院,四川 自贡 643000
    2.中昊晨光化工研究所有限公司,四川 自贡 643201
  • 收稿日期:2020-06-25 修回日期:2021-03-23 出版日期:2021-04-22 发布日期:2021-04-27
  • 通讯作者: 李颜利
  • 作者简介:汪琴琴(1995-),女,四川内江人,硕士研究生,电话:18381302644,E-mail: 547726284@qq.com
  • 基金资助:
    四川省科技厅重点研发项目资助(2019YFG0174);四川省科技厅重点研发项目资助(2020YFG0422);自贡市重点科技计划项目资助(2019YYJC19);四川轻化工大学人才引进项目资助(2018RCL02)

Green synthesis and application of a condensating agent with short fluorocarbon chain

WANG Qin-qin1(),LI Yan-li1(),ZOU Wei1,YAN Jie1,LIU Bo2,LI Hui2   

  1. 1. College of Chemical Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000, China
    2. Zhonghao Chenguang Chemical Research Institute of Chemical Industry Co., Ltd., Zigong, Sichuan 643201, China
  • Received:2020-06-25 Revised:2021-03-23 Online:2021-04-22 Published:2021-04-27
  • Contact: Yan-li LI

摘要:

以2,2,3,3,4,4,5,5-八氟-1-戊醇(OFP)作为短碳氟链来源,三聚氯氰(TCT)为反应活性基团,通过一锅两步法合成了一种高活性的三嗪类缩合剂1-氯-3,5-双((八氟-1-戊基)氧基)-三嗪(DFCT),采用傅里叶变换红外光谱(FT-IR)、核磁共振(1H NMR、13C NMR、19F NMR)对目标产物(DFCT)进行了表征,通过质谱对中间体2,4-二氯-6-((八氟-1-戊基)氧基)-三嗪(DCFT)和目标产物DFCT进行了表征;同时对缩合试剂合成条件进行研究,确定了合成的较佳工艺:二氯甲烷为溶剂,氢氧化钠为中和试剂,n(TCT)∶n(OFP)=1∶2.2,先在0 ℃反应生成中间体DCFT,然后在30 ℃反应生成目标产物DFCT,收率为96%。用制备的DFCT作为缩合试剂,以羧酸和胺/醇为原料,分别合成了酰胺类目标产物(Ⅰa~Ⅰc)和酯类目标产物(Ⅱa~Ⅱc),说明DFCT可应用于酰胺化、酯化反应的缩合试剂,且反应条件温和,易于操作。

关键词: 短氟碳链, 缩合试剂, 合成, 酰胺化, 酯化

Abstract:

A triazine-type condensating agent with high activity, 1-chloro-3,5-bis((octafluoropentyl)oxy)-triazine(DFCT), was synthesized by one-pot two-step method, in which cyanuric chloride(TCT)was used as reactive group and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol(OFP)was used as the source of short fluorocarbon chain. The intermediate(2,4-dichloro-6-((octafluoropentyl)oxy)-triazine, DCFT)and the target product(DFCT)were characterized by FT-IR,1H NMR,13C NMR,19F NMR and mass spectrometry. The reaction conditions were optimized according to the yield of product: Dichloromethane was used as the solvent; sodium hydroxide was used as acid binding agent; n(TCT)∶n(OFP)=1∶2.2; the reaction temperature was 0 ℃ to generate DCFT, and then 30 ℃ to obtain the target product DFCT, and the yield of DFCT was 96%. DFCT was used as a condensating agent to activate carboxylic acid which would react with amines/alcohols to produce amides(Ⅰa-Ⅰc)/esters(Ⅱa-Ⅱc). It showed that DFCT could be used as a condensating agent for amidation and esterification reactions, and the reaction conditions were mild and easy to operate.

Key words: short fluorocarbon chain, condensating agent, synthesis, amidation, esterification

中图分类号: 

  • TQ423