A green route to 1,2-cyclohexanediol via the hydrolysis of cyclohexene oxide catalyzed by water
详细信息    查看全文
  • 作者:Qiusheng Yang (1)
    Xue Yang (1)
    Yanji Wang (1) yqiusheng@sina.com
    Haiou Wang (1)
    Qingyan Cheng (1)
  • 关键词:Hydrolysis – ; Water – ; Cyclohexene oxide – ; 1 ; 2 ; Cyclohexanediol ; Polymer
  • 刊名:Research on Chemical Intermediates
  • 出版年:2012
  • 出版时间:November 2012
  • 年:2012
  • 卷:38
  • 期:9
  • 页码:2277-2284
  • 全文大小:358.8 KB
  • 参考文献:1. Y.F. Korytnyi, M.A. Vartapetov, S.A. Nizova, P.S. Belov, Petrochem. U.S.S.R. 28, 39 (1988)
    2. Q.Z. Xiong, Z.L. Liu, M. Chen, Y.M. Li, W.W. Liao, W. Ren, Fine Chem. 18(6), 137 (2001)
    3. A. Romero, A. Santos, G. Ruiz, E. Sim贸n, Ind. Eng. Chem. Res. 50(14), 8498 (2011)
    4. A.P. Zhang, S. Gao, Y. Lv, Z.W. Xi, Res. Chem. Int. 35(5), 563 (2009)
    5. W.B. Fan, P. Wu, T. Tatsumi, J. Catal. 256(1), 62 (2008)
    6. G. Sankar, N.R. Shiju, A. Welch, Stud. Surf. Sci. Catal. 172, 365 (2007)
    7. C. Palazzi, L. Oliva, M. Signoretto, G. Strukul, J. Catal. 194(2), 286 (2000)
    8. M.G. Buonomenna, G. Golemme, M.P. De Santo, E. Drioli, Org. Process Res. Dev. 14, 252 (2009)
    9. N. Azizi, M.R. Saidi, Org. Lett. 7(17), 3649 (2005)
    10. H. Cavdar, N. Saracoglu, Tetrahedron 65(5), 985 (2009)
    11. P. Salehi, M.M. Khodaei, M.A. Zolfigol, A. Keyvan, Synth. Commun. 33(17), 3041 (2003)
    12. J.L. Jiang, Z. Xiu, R. Hua, Synth. Commun. 38(2), 232 (2008)
    13. A. Venkat Narsaiah, B.V.S. Reddy, K. Premalatha, S.S. Reddy, J.S. Yadav, Catal. Lett. 131(3–4), 480 (2009)
    14. R. Dalpozzo, M. Nardi, M. Oliverio, R. Paonessa, A. Procopio, Synthesis 20, 3433 (2009)
    15. J.M. Ready, E.N. Jacobsen, J. Am. Chem. Soc. 123(11), 2687 (2001)
    16. S.H. Lee, E.Y. Lee, D.W. Yoo, S.J. Hong, J.H. Lee, H. Kwak, Y.M. Lee, J. Kim, C. Kim, J.K. Lee, New J. Chem. 31(9), 1579 (2007)
    17. D.P. Steinhuebel, S.J. Lippard, Organometallics 18(2), 109 (1998)
    18. V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Tetrahedron 59(41), 8213 (2003)
    19. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S.A. Taghavi, Catal. Commun. 8(12), 2087 (2007)
    20. A. McCluskey, S.K. Leitch, J. Garner, C.E. Caden, T.A. Hill, L.R. Odell, S.G. Stewart, Tetrahedron Lett. 46(47), 8229 (2005)
    21. Z. Wang, Y.T. Cui, Z.B. Xu, J. Qu, J. Org. Chem. 73(6), 2270 (2008)
    22. H.Y. Tian, Y.D. Zhang, Z.X. Wang, Speciality Petrochem. 26(2), 37 (2009)
    23. H.C. Kolb, M. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40(11), 2004 (2001)
    24. N. Akiya, P.E. Savage, Ind. Eng. Chem. Res. 40(8), 1822 (2001)
    25. H. Kotsuki, M. Kataoka, H. Nishizawa, Tetrahedron Lett. 34(25), 4031 (1993)
    26. D.J. Miller, S.B. Hawthorne, J. Chem. Eng. Data 45(1), 78 (2000)
  • 作者单位:1. Institute of Green Chemical Technology, Hebei University of Technology, Tianjin, 300130 China
  • ISSN:1568-5675
文摘
Effective hydrolysis of cyclohexene oxide (CHO) was conducted by heating in water between 100 and 140 掳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 掳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.

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700