A green route to 1,2-cyclohexanediol via the hydrolysis of cyclohexene oxide catalyzed by water

被引:5
|
作者
Yang, Qiusheng [1 ]
Yang, Xue [1 ]
Wang, Yanji [1 ]
Wang, Haiou [1 ]
Cheng, Qingyan [1 ]
机构
[1] Hebei Univ Technol, Inst Green Chem Technol, Tianjin 300130, Peoples R China
关键词
Hydrolysis; Water; Cyclohexene oxide; 1,2-Cyclohexanediol; Polymer; EPOXIDES; ALCOHOLS; DIOLS; AZIRIDINES; CONVERSION; OXIDATION;
D O I
10.1007/s11164-012-0544-7
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Effective hydrolysis of cyclohexene oxide (CHO) was conducted by heating in water between 100 and 140 A degrees C without another catalyst. It provided 100 % purity and 100 % yield of trans-1,2-cyclohexanediol (1,2-CHD) with five times of H2O to CHO at 120 A degrees C for 6 h. These intermediates of polyether polyols could be totally decomposed to 1,2-CHD (monomer) by hot water under the same condition. The improved process eliminates the purification and markedly reduces the cost of 1,2-CHD in the follow-up industrial production. The main factors, such as reaction temperature, time, and water volume, were investigated. It was proposed that water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis of CHO and polymers.
引用
收藏
页码:2277 / 2284
页数:8
相关论文
共 50 条
  • [11] Two routes to 1,2-cyclohexanediol catalyzed by zeolites under solvent-free condition
    Lei, Wenkang
    Wu, Zaikun
    Ma, Jie
    Yu, Ping
    Luo, Yunbai
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (09) : 6893 - 6905
  • [12] Oxidation of 1,2-cyclohexanediol as a step for adipic acid synthesis
    Peckh, Kamil
    Lisicki, Dawid
    Pabich, Ewelina
    Orlinska, Beata
    JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2022, 110 : 131 - 136
  • [13] Study on kinetics of polyesterification of 1,2-cyclohexanediol with adipic acid
    Yuan, Jian-Min
    Deng, Jian-Ru
    Huaxue Fanying Gongcheng Yu Gongyi/Chemical Reaction Engineering and Technology, 2003, 19 (02):
  • [14] CONFORMATIONAL AND MOLECULAR MECHANICS STUDIES OF 1,2-CYCLOHEXANEDIOL DERIVATIVES
    GRINDLEY, TB
    ROCKWELL, G
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 95 - CARB
  • [15] RH(I)-CATALYZED FORMATION OF 2 CONFORMERS DUE TO CIS-1,2-CYCLOHEXANEDIOL
    FUNAKOSHI, K
    SAKAI, K
    HATA, T
    TAMURA, C
    TETRAHEDRON LETTERS, 1989, 30 (36) : 4849 - 4852
  • [16] An unexpected co-crystal with a variable degree of order:: 1:1 rac-1,2-cyclohexanediol/triphenylphosphine oxide
    Siegler, Maxime A.
    Fu, Yigang
    Simpson, Greg H.
    King, Daniel P.
    Parkin, Sean
    Brock, Carolyn Pratt
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2007, 63 (06) : 912 - 925
  • [17] Oxidation of Cyclohexene to trans-1,2-Cyclohexanediol Promoted by p-Toluenesulfonic Acid without Organic Solvents
    Rosatella, Andreia A.
    Afonso, Carlos A. M.
    Branco, Luis C.
    JOURNAL OF CHEMICAL EDUCATION, 2011, 88 (07) : 1002 - 1003
  • [18] DEVELOPMENT OF NEW TECHNOLOGY FOR THE SYNTHESIS OF 1,2-CYCLOHEXANEDIOL AS A STAGE OF PYROCATECHOL PRODUCTION
    SEMENOV, MV
    KOMAROV, AG
    MIKHAILYUK, AI
    LITVINTSEV, IY
    SAPUNOV, VN
    PETROLEUM CHEMISTRY, 1995, 35 (02) : 111 - 115
  • [19] Measurement and correlation of solubilities of trans-1,2-cyclohexanediol in methylacetate and water mixed solvent
    School of Chemical Engineering, Zhengzhou University, Zhengzhou 450000, China
    Huagong Xuebao, 2007, 4 (810-813):
  • [20] Study on molecular dynamics and phase transitions in 1,2-cyclohexanediol and 1,3-cyclohexanediol isomers by calorimetry and dielectric spectroscopy
    Galazka, Miroslaw
    Jasiurkowska-Delaporte, Malgorzata
    Eusebio, M. Ermelinda S.
    Rosado, Mario T. S.
    Juszynska-Galazka, Ewa
    Dryzek, Ewa
    JOURNAL OF MOLECULAR LIQUIDS, 2023, 369