以氧化石墨烯为酸催化剂制备2,5-二甲基-N-苯基吡咯

陈春燕; 郭晓亚; 吕广强; Christian Marcus Pedersen; 乔岩; 侯相林; 王英雄

doi:10.1016/S1872-5805(17)60113-6

以氧化石墨烯为酸催化剂制备2,5-二甲基-N-苯基吡咯

doi: 10.1016/S1872-5805(17)60113-6

1.
上海大学环境与化学工程学院, 上海 200444;
2.
中国科学院山西煤炭化学研究所, 山西省生物炼制工程技术研究中心, 山西太原 030001;
3.
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark;
4.
中国科学院山西煤炭化学研究所, 煤转化重点实验室, 山西太原 030001

基金项目: 国家重点基础研究发展规划项目资助（973计划项目，2012CB215305）；国家自然科学基金（21106172，21403273）；中国科学院引进杰出技术人才计划（2011137）；中国科学院国际人才交流计划项目资助（2015VMB052）.

详细信息

通讯作者:
侯相林,研究员.E-mail:houxianglin@sxicc.ac.cn;王英雄,副研究员.E-mail:wangyx@sxicc.ac.cn

中图分类号: TQ127.1⁺1
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- 被引次数: 0
出版历程
- 收稿日期: 2017-01-20
- 录用日期: 2017-04-26
- 修回日期: 2017-04-10
- 刊出日期: 2017-04-28

Graphene oxide: a novel acid catalyst for the synthesis of 2, 5-dimethyl-N-phenyl pyrrole by the Paal-Knorr condensation

1.
Department of Chemical Engineering, Shanghai University, Shanghai 200444, China;
2.
Shanxi Engineering Research Center of Biorefinery, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China;
3.
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen Ø, Denmark;
4.
State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China

Funds: Major State Basic Research Development Program of China (973 Program, 2012CB215305); National Natural Science Foundation of China (21106172, 21403273); Youth Innovation Promotion Association of Chinese Academy of Sciences (2011137); CAS President's International Fellowship Initiative (2015VMB052).

摘要

摘要: 介绍了氧化石墨烯作为一种高效且可回收的催化剂应用于2，5-己二酮与苯胺通过Paal-Knorr缩合反应合成N-取代吡咯。研究了反应时间、反应温度、溶剂、催化剂用量以及苯胺与2，5-己二酮的摩尔比对2，5-二甲基-N-苯基吡咯收率的影响。通过原位核磁技术在分子水平上跟踪了Paal-Knorr缩合的反应过程。结果表明在25℃下通过氧化石墨烯的催化作用反应6 h后吡咯的最大收率可达到90%。氧化石墨烯易回收，且经5次回收使用后还能表现出很好的循环使用性和高催化性能。
- 氧化石墨烯 /
- Paal-Knorr /
- 吡咯 /
- 非均相酸催化 /
- 原位核磁
Abstract: Graphene oxide (GO) was used as an efficient and recyclable catalyst for the synthesis of N-substituted pyrrole using a Paal-Knorr condensation reaction between 2,5-hexanedione and aniline. The effects of reaction time, reaction temperature, solvent, catalyst loading and molar ratio of aniline to 2,5-hexanedione on the yield of 2,5-dimethyl-N-phenyl pyrrole were investigated. In situ NMR was used to follow the Paal-Knorr reaction at the molecular level. Results revealed that the oxygen-containing groups of GO, such as sulfonic acid and carboxyl groups, played a key role in this catalytic reaction. Polar protic solvents were favorable for the reaction. The catalytic activity increased with temperature without any side reaction. The GO could be easily recovered and showed remarkable reusability and excellent catalytic performance allowing it to be reused 5 times.
- Graphene oxide /
- Paal-Knorr /
- Pyrrole /
- Heterogeneous acid catalysis /
- In situ NMR

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