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
  • [1] Organic Solvent- and Halide-Free Oxidation with Hydrogen Peroxide
    Chishiro, Takefumi
    Kon, Yoshihiro
    Sato, Kazuhiko
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2008, 66 (11) : 1085 - 1092
  • [2] Organic solvent- and halide-free oxidation of alcohols with aqueous hydrogen peroxide
    Sato, K
    Aoki, M
    Takagi, J
    Noyori, R
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12386 - 12387
  • [3] A practical method for alcohol oxidation with aqueous hydrogen peroxide under organic solvent- and halide-free conditions
    Sato, K
    Aoki, M
    Takagi, J
    Zimmermann, K
    Noyori, R
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (10) : 2287 - 2306
  • [4] A halide-free method for olefin epoxidation with 30% hydrogen peroxide
    Sato, K
    Aoki, M
    Ogawa, M
    Hashimoto, T
    Panyella, D
    Noyori, R
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (04) : 905 - 915
  • [5] A Halide-Free Method for Olefin Epoxidation with 30% Hydrogen Peroxide
    Sato, K.
    Aoki, M.
    Ogawa, M.
    Hashimoto, T.
    Bulletin of the Chemical Society of Japan, 70 (04):
  • [6] Hydrogen peroxide oxidation of aldehydes to carboxylic acids: an organic solvent-, halide- and metal-free procedure
    Sato, K
    Hyodo, M
    Takagi, J
    Aoki, M
    Noyori, R
    TETRAHEDRON LETTERS, 2000, 41 (09) : 1439 - 1442
  • [7] Oxidation of sulfides to sulfoxides and sulfones with 30% hydrogen peroxide under organic solvent- and halogen-free conditions
    Sato, K
    Hyodo, M
    Aoki, M
    Zheng, XQ
    Noyori, R
    TETRAHEDRON, 2001, 57 (13) : 2469 - 2476
  • [8] A "green" route to adipic acid: Direct oxidation of cyclohexenes with 30 percent hydrogen peroxide
    Sato, K
    Aoki, M
    Noyori, R
    SCIENCE, 1998, 281 (5383) : 1646 - 1647
  • [9] A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions
    Sato, K
    Aoki, M
    Ogawa, M
    Hashimoto, T
    Noyori, R
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23): : 8310 - 8311
  • [10] Chemoselective oxidation of alcohols by a H2O2-Pt black system under organic solvent- and halide-free conditions
    Kon, Yoshihiro
    Yazawa, Hideaki
    Usui, Yoko
    Sato, Kazuhiko
    CHEMISTRY-AN ASIAN JOURNAL, 2008, 3 (8-9) : 1642 - 1648