Page 223 - 《精细化工》2020年第6期

第 37 卷第 6 期 精 细 化 工 Vol.37, No.6
202 0 年 6 月 FINE CHEMICALS June 2020

精细化工中间体
N,N-双[2-(1,3-二氧异吲哚-2-基)乙基]

丙烯酰胺的合成与表征

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郭 睿，徐 康 ，张晓飞，闫育蒙，马丽娟
（陕西科技大学 教育部轻化工助剂化学与技术重点实验室，陕西 西安 710021）

摘要：以邻苯二甲酸酐（PA）、二乙烯三胺（DETA）为原料，经亲电加成-消除反应合成有机中间体双（2-邻苯
二甲酰亚胺）胺（DETA-2PA），其再与丙烯酰氯（AC）发生酰胺化反应合成有机中间体 N,N-双[2-（1,3-二氧异
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吲哚-2-基）乙基]丙烯酰胺（AC-DETA-2PA）。通过 FTIR、 HNMR、元素分析、HRMS、HPLC 对产物结构进
行了确证，并用 TGA、荧光光谱对产物的性能进行了测试。考察了反应温度、反应时间、n(AC)∶n(DETA-2PA)
及催化剂用量 4 个因素对合成 AC-DETA-2PA 胺值的影响。通过响应面设计对 AC-DETA-2PA 的合成工艺进行了
优化，确定其较佳合成工艺条件为：n(AC)∶n(DEETA-2PA)=1.6∶1.0，反应温度为 25 ℃，催化剂氢化钠用量
占反应物（AC 和 DETA-2PA）总质量的 8.46%，反应时间 4 h。在该条件下，AC-DETA-2PA 的胺值可达
2.96 mg KOH/g。
关键词：双(2-邻苯二甲酰亚胺)胺；N,N-双[2-（1,3-二氧异吲哚-2-基）乙基]丙烯酰胺；响应面设计；精细化工中
间体
中图分类号：Q626.1 文献标识码：A 文章编号：1003-5214 (2020) 06-1289-08

Synthesis and characterization of N,N-bis[2-(1,3-

dioxoisoindol-2-yl)ethyl] acrylamide

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GUO Rui, XU Kang , ZHANG Xiaofei, YAN Yumeng, MA Lijuan
（Key Laboratory of Auxiliary Chemistry and Technology for Light Chemicals, Ministry of Education, Shaanxi
University of Science & Technology, Xi'an 710021, Shaanxi, China）

Abstract: Bis(2-phthalimide) amine (DETA-2PA) was synthesized from phthalic anhydride (PA) and
diethylenetriamine (DETA) through electrophilic addition-elimination reaction. The organic intermediate
DETA-2PA was then amidated with acryloyl chloride (AC) to synthesize an organic intermediate,
N,N-bis[2-(1,3-dioxoindol-2-yl)ethyl] acrylamide (AC-DETA-2PA). The structure of the product was
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confirmed by FTIR, HNMR, elemental analysis, HRMS and HPLC. The performance of the product was
tested by TGA and fluorescence spectrum. The effects of reaction temperature, reaction time, n(AC)∶
n(DETA-2PA) and catalyst dosage on the amine value of AC-DETA-2PA were investigated. The synthesis
process of AC-DETA-2PA was optimized by response surface design. The best synthetic process conditions
were determined as follows: n(AC)∶n(DETA-2PA)=1.6∶1.0, reaction temperature 25 ℃, dosage of
catalyst sodium hydride accounting for 8.46% of the total mass of the reactants (AC and DETA-2PA) and
reaction time 4 h. Under these conditions, the amine value of AC-DETA-2PA could reach 2.96 mg KOH/g.
Key words: bis(2-phthalimide) amine; N,N-bis[2-(1,3-dioxoisoindol-2-yl)ethyl] acrylamide; response
surface design; fine chemical intermediates

[1]
酰亚胺类化合物通常应用在生物学、合成化学、 医学和聚合物化学等领域 。在医学中，可用于合

收稿日期：2019-10-28; 定用日期：2020-03-03; DOI: 10.13550/j.jxhg.20191020
基金项目：陕西省重点研发计划（2017GY-185, 2017ZDXM-GY-087）；西安市科技计划项目〔CXY1701(3)〕
作者简介：郭 睿（1959—），男，教授，E-mail：365726475@qq.com。联系人：徐 康（1995—），男，硕士生，E-mail：294631213@qq.com。