Solvent-dependent selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid under neat conditions

被引：46
作者：
Liu, Kai-Jian [1 ]
Zeng, Tang-Yu [1 ]
Zeng, Jia-Le [1 ]
Gong, Shao-Feng [1 ]
He, Jun-Yi [2 ]
Lin, Ying-Wu [4 ]
Tan, Jia-Xi [3 ]
Cao, Zhong [2 ]
He, Wei-Min [1 ,2 ]
机构：
[1] Hunan Univ Sci & Engn, Dept Chem, Yongzhou 425100, Peoples R China
[2] Changsha Univ Sci & Technol, Hunan Prov Key Lab Mat Protect Elect Power & Tran, Changsha 410114, Peoples R China
[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Peoples R China
[4] Univ South China, Sch Chem & Chem Engn, Hengyang 421001, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2019年 / 30卷 / 12期
关键词：
5-Hydroxymethylfurfural; 2,5-Furandicarboxylic acid; Base-free; External initiator-free; Dioxygen; INDUCED DEOXYGENATIVE C2-SULFONYLATION; QUINOLINE N-OXIDES; AEROBIC OXIDATION; CATALYST; CYCLIZATION; ALCOHOL; KETONES; AMINES; BASE;
D O I：
10.1016/j.cclet.2019.10.031
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An eco-friendly and economical route for the oxidation of 5-hydroxymethylfurfural (HMF) to 2,5-furandicarboxylic acid (FDCA) with atmospheric dioxygen as the sole oxidant under acid-, base-, metal-, and external initiator-free conditions in minimal solvent was reported. In the present reaction, the 1,2-diethoxyethylane has a dual role: reaction medium and free-radical initiator. The FDCA easily crystallizes during the reaction and was simple purified via recrystallization to provide the pure FDCA. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：2304 / 2308
页数：5
相关论文
共 59 条
[1]   Clean preparation of S-thiocarbamates with in situ generated hydroxide in 2-methyltetrahydrofuran [J].
Bao, Wen-Hu ;
Wang, Zheng ;
Tang, Xiao ;
Zhang, Yun-Fu ;
Tan, Jia-Xi ;
Zhu, Qin ;
Cao, Zhong ;
Lin, Ying-Wu ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2259-2262
[2]   The concept of dual roles design in clean organic preparation [J].
Cao, Zhong ;
Zhu, Qin ;
Lin, Ying-Wu ;
He, Wei-Min .
CHINESE CHEMICAL LETTERS, 2019, 30 (12) :2132-2138
[3]   B2pin2-catalyzed oxidative cleavage of a C?C double bond with molecular oxygen [J].
Cheng, Zhen ;
Jin, Weiwei ;
Liu, Chenjiang .
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (06) :841-845
[4]   Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids for the synthesis of 2-sulfonylquinoline via radical reactions [J].
Dong, Dao-Qing ;
Li, Li-Xia ;
Li, Guang-Hui ;
Deng, Qi ;
Wang, Zu-Li ;
Long, Shu .
CHINESE JOURNAL OF CATALYSIS, 2019, 40 (10) :1494-1498
[5]   Carbon Support Surface Effects in the Gold-Catalyzed Oxidation of 5-Hydroxymethylfurfural [J].
Donoeva, Baira ;
Masoud, Nazila ;
de Jongh, Petra E. .
ACS CATALYSIS, 2017, 7 (07) :4581-4591
[6]   OXIDATION OF N-ALKYLAMIDES TO NOVEL HYDROPEROXIDES BY DIOXYGEN [J].
DRAGO, RS ;
RILEY, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (01) :215-218
[7]   Influence of Support Basic Sites in Green Oxidation of Biobased Substrates Using Au-Promoted Catalysts [J].
Ferraz, Camila P. ;
Zielinski, Michal ;
Pietrowski, Mariusz ;
Heyte, Svetlana ;
Dumeignil, Franck ;
Rossi, Liane M. ;
Wojcieszak, Robert .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2018, 6 (12) :16332-16340
[8]   Copper-catalyzed aerobic oxidative coupling of ketones with P(O)-H compounds leading to β-ketophosphine oxides [J].
Fu, Qiang ;
Yi, Dong ;
Zhang, Zhijie ;
Liang, Wu ;
Chen, Suyuan ;
Yang, Lu ;
Zhang, Qiang ;
Ji, Jianxin ;
Wei, Wei .
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07) :1385-1389
[9]   Bio-based solvents: an emerging generation of fluids for the design of eco-efficient processes in catalysis and organic chemistry [J].
Gu, Yanlong ;
Jerome, Francois .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (24) :9550-9570
[10]   Selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over MnOx-CeO2 composite catalysts [J].
Han, Xuewang ;
Li, Chaoqun ;
Liu, Xiaohui ;
Xia, Qineng ;
Wang, Yanqin .
GREEN CHEMISTRY, 2017, 19 (04) :996-1004
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