A green method of adipic acid synthesis: organic solvent- and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide

被引:104
|
作者
Usui, Y [1 ]
Sato, K [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba Cent 5, Tsukuba, Ibaraki 3058565, Japan
关键词
D O I
10.1039/b305847f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Cyclohexanone and cyclohexanol are oxidized to adipic acid in high yield with aqueous 30% H2O2 in the presence of H2WO4 as a catalyst under organic solvent- and halide-free conditions. It is important that no solvent is used in order to achieve high reactivity in this heterogeneous reaction. The use of t-butyl alcohol or dioxane as a solvent (homogeneous conditions) significantly decreases the yield of adipic acid from cyclohexanone. This ketone-to-dicarboxylic acid conversion is applicable to five- to eight-membered cyclic ketones. No operational problems are foreseen for a large-scale version of this green process.
引用
收藏
页码:373 / 375
页数:3
相关论文
共 50 条
  • [11] Hydrogen peroxide oxidation of benzylic alcohols to benzaldehydes and benzoic acids under halide-free conditions
    Sato, K
    Takagi, J
    Aoki, M
    Noyori, R
    TETRAHEDRON LETTERS, 1998, 39 (41) : 7549 - 7552
  • [12] The Effects of Acid and Hydrogen Peroxide Stabilizer on the Thermal Hazard of Adipic Acid Green Synthesis
    Liu, Yinshan
    Ni, Lei
    Yao, Hang
    Su, Jimi
    Cheng, Zhen
    SUSTAINABILITY, 2023, 15 (08)
  • [13] A non-nitric acid method of adipic acid synthesis: organic solvent- and promoter-free oxidation of cyclohexanone with oxygen over hollow-structured Mn/TS-1 catalysts
    Zou, Guoqiang
    Zhong, Wenzhou
    Mao, Liqiu
    Xu, Qiong
    Xiao, Jiafu
    Yin, Dulin
    Xiao, Zisheng
    Kirk, Steven Robert
    Shu, Tao
    GREEN CHEMISTRY, 2015, 17 (03) : 1884 - 1892
  • [14] Influence of reaction conditions on product distribution in the green oxidation of cyclohexene to adipic acid with hydrogen peroxide
    Jin, Peng
    Zhao, Zhonghua
    Dai, Zhipeng
    Wei, Donghui
    Tang, Mingsheng
    Wang, Xiangyu
    CATALYSIS TODAY, 2011, 175 (01) : 619 - 624
  • [15] Anderson-type polyoxometalate as excellent catalyst for green synthesis of adipic acid with hydrogen peroxide
    Jin, Peng
    Wei, Huijuan
    Zhou, Limin
    Wei, Donghui
    Wen, Yiqiang
    Zhao, Bin
    Wang, Xiangyu
    Li, Baojun
    MOLECULAR CATALYSIS, 2021, 510
  • [16] Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent
    D'Aleo, Danielle N.
    Allard, Sheena R.
    Foglia, Cassandra C.
    Parent, Shawna L. M.
    Rohr, David J.
    Gottardo, Christine
    MacKinnon, Craig D.
    CANADIAN JOURNAL OF CHEMISTRY, 2013, 91 (08) : 679 - 683
  • [17] Green Process for Adipic Acid Synthesis: Oxidation by Hydrogen Peroxide in Water Micromelusions using Benzalkonium Chloride C12-14 Surfactant
    Lesage, Geoffroy
    Penate, Isariebel Quesada
    Cognet, Patrick
    Poux, Martine
    INTERNATIONAL JOURNAL OF CHEMICAL REACTOR ENGINEERING, 2012, 10
  • [18] Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine N-oxides
    Rassadin, Valentin A.
    Zimin, Dmitry P.
    Raskil'dina, Gulnara Z.
    Ivanov, Alexander Yu.
    Boyarskiy, Vadim P.
    Zlotskii, Semen S.
    Kukushkin, Vadim Yu.
    GREEN CHEMISTRY, 2016, 18 (24) : 6630 - 6636
  • [19] Microwave assisted solvent-free oxidation of organic halides using aqueous hydrogen peroxide
    Khurana, Jitender M.
    Kumar, Sanjay
    LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (02) : 137 - 139
  • [20] Organic-solvent-free phase-transfer oxidation of alcohols using hydrogen peroxide
    Hulce, M
    Marks, DW
    JOURNAL OF CHEMICAL EDUCATION, 2001, 78 (01) : 66 - 67