Page 152 - 《精细化工》2022年第10期

第 39 卷第 10 期 精 细 化 工 Vol.39, No.10
2022 年 10 月 FINE CHEMICALS Oct. 2022

催化与分离提纯技术
UCST 型玫瑰红催化剂的制备与催化合成

四氢异喹啉类化合物

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黄宝强 ，蔡亭伟 ，王照朋 ，赵强强 1,2*
（1. 东华大学 化学化工与生物工程学院，上海 201620；2. 山东中康国创先进印染技术研究院有限公司
国家先进印染技术创新中心, 山东 泰安 271000）

摘要：以甲基丙烯酸甲酯（MMA）和甲基丙烯酰氧乙基三甲基氯化铵（DMC）为原料，合成了聚合物
P(MMA-xDMC)（x 为 DMC 的含量，以 MMA 物质的量为基准，下同）。通过 P(MMA-xDMC)对玫瑰红（RB）
的吸附作用，制得高临界溶解温度（UCST）型 RB 催化剂〔P(MMA-xDMC)-RB〕。对聚合物的相对分子质量、
UCST 以及 P(MMA-xDMC)-RB 在溶液中溶解再析出的稳定性进行了测试，考察了 P(MMA-xDMC)-RB 催化 N-
苯基四氢异喹啉衍生物与硝基甲烷反应的活性与稳定性。结果表明，x为0.5%~2.0%时，产物的UCST在37~42 ℃，
P(MMA-1% DMC)-RB 经过 4 次溶解-沉淀实验后，溶解再析出百分率达第一次的 93%以上；在 N-苯基四氢异喹
啉衍生物和硝基甲烷的交叉脱氢偶联反应中，P(MMA-1% DMC)-RB 具有较高的催化活性，与常规 RB 相当。在
反应温度为 45 ℃、白色 1 W LED 光源下反应 8 h，产物四氢异喹啉衍生物的收率在 80%以上。该 UCST 型 RB
催化剂具有良好循环稳定性，循环使用 8 次后，四氢异喹啉衍生物的收率降为 77.9%。
关键词：交叉脱氢偶联反应；UCST 聚合物；玫瑰红；光催化反应；催化技术
中图分类号：O643.3 文献标识码：A 文章编号：1003-5214 (2022) 10-2086-06

UCST type Rose Bengal catalyst preparation and its catalytic synthesis of

tetrahydroisoquinoline derivatives

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HUANG Baoqiang , CAI Tingwei , WANG Zhaopeng , ZHAO Qiangqiang 1,2*
（1.College of Chemical and Bioengineering, Donghua University, Shanghai 201620, China;2.Shandong Zhongkang
Guochuang Advanced Printing and Dyeing Technology Research Institute Co., Ltd., National Advanced Printing and Dyeing
Technology Innovation Center, Taian 271000, Shandong, China）
Abstract: UCST (high critical dissolution temperature) type Red Bengal (RB) catalyst
P(MMA-xDMC)-RB (x refers to the content of DMC, based on the molar amount of MMA, the same below)
was prepared via adsorption of P(MMA-xDMC) on RB, of which P(MMA-xDMC) was synthesized from
methyl methacrylate (MMA) and methyl acryloxyethyl trimethyl ammonium chloride (DMC). The relative
molecular mass of the polymer obtained, UCST and stability of P(MMA-xDMC)-RB dissolved and
reprecipitated in solution were analyzed, followed by investigation on its catalytic activity and stability in
the reaction of N-phenyltetrahydroisoquinoline derivatives with nitromethane. The results showed that the
UCST of products prepared was 37~42 ℃ when x = 0.5%~2.0%, and the recovery of P(MMA-1%
DMC)-RB still reached >93% after four cycles of dissolution-precipitation. In the cross dehydrogenation
coupling reaction between N-phenyltetrahydroisoquinoline derivatives and nitromethane, P(MMA-1%
DMC)-RB exhibited high catalytic activity comparable to that of conventional RB. The yield of
tetrahydroisoquinoline was higher than 80% with white 1 W LED light source irradiation for 8 h at 45 ℃.
Moreover, the UCST type RB catalyst displayed good cycle stability with the yield of
tetrahydroisoquinoline derivatives decreased 77.9% after catalyst being cycled for 8 times.

收稿日期：2022-01-24; 定用日期：2022-06-07; DOI: 10.13550/j.jxhg.20220089
基金项目：中国博士后科学基金资助项目（2021M690599）；山东省自然科学基金资助项目（ZR2021ME251）
作者简介：黄宝强（1997—），男，硕士生，E-mail：2190639@mail.dhu.edu.cn。联系人：赵强强（1987—），男，讲师，E-mail：qqzhao@
dhu.edu.cn。