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

CHEN Chun-yan; GUO Xiao-ya; LU Guang-qiang; Christian Marcus Pedersen; QIAO Yan; HOU Xiang-lin; WANG Ying-xiong

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

Volume 32 Issue 2

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Article Navigation > New Carbon Mater. > 2017 > 32(2): 160-167

CHEN Chun-yan, GUO Xiao-ya, LU Guang-qiang, Christian Marcus Pedersen, QIAO Yan, HOU Xiang-lin, WANG Ying-xiong. Graphene oxide: a novel acid catalyst for the synthesis of 2, 5-dimethyl-N-phenyl pyrrole by the Paal-Knorr condensation. New Carbon Mater., 2017, 32(2): 160-167. doi: 10.1016/S1872-5805(17)60113-6

Citation:

CHEN Chun-yan, GUO Xiao-ya, LU Guang-qiang, Christian Marcus Pedersen, QIAO Yan, HOU Xiang-lin, WANG Ying-xiong. Graphene oxide: a novel acid catalyst for the synthesis of 2, 5-dimethyl-N-phenyl pyrrole by the Paal-Knorr condensation. New Carbon Mater., 2017, 32(2): 160-167. doi: 10.1016/S1872-5805(17)60113-6

Citation:

CHEN Chun-yan, GUO Xiao-ya, LU Guang-qiang, Christian Marcus Pedersen, QIAO Yan, HOU Xiang-lin, WANG Ying-xiong. Graphene oxide: a novel acid catalyst for the synthesis of 2, 5-dimethyl-N-phenyl pyrrole by the Paal-Knorr condensation. New Carbon Mater., 2017, 32(2): 160-167. doi: 10.1016/S1872-5805(17)60113-6

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

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

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).

Received Date: 2017-01-20
Accepted Date: 2017-04-26
Rev Recd Date: 2017-04-10
Publish Date: 2017-04-28

Abstract

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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References(34)

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