Articles & Issues
- Language
- English
- Conflict of Interest
- In relation to this article, we declare that there is no conflict of interest.
- Publication history
-
Received July 21, 2003
Accepted September 8, 2003
- This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
Copyright © KIChE. All rights reserved.
All issues
A Novel Non-phosgene Approach to the Synthesis of Methyl N-phenyl Carbamate by a Reaction of Methanol with Phenylurea
Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan Shanxi 030001, China 1Laboratory of Molecular Catalysis and Innovative Materials, Department of Chemistry, Fudan University, Shanghai 200433, China
Korean Journal of Chemical Engineering, March 2004, 21(2), 378-380(3), 10.1007/BF02705423
Download PDF
Abstract
A novel non-phosgene process for the synthesis of methyl N-phenyl carbamate (MPC) by a reaction of phenylurea with methanol was studied. The reaction between phenylurea and methanol was found to be a spontaneous reaction that took place in the absence of catalyst and gave MPC as the main product. Addition of a catalyst markedly influenced the reaction behavior. A basic catalyst greatly enhanced the yield of MPC, whereas an acidic catalyst promoted the formation of aniline and methyl carbamate. Moderate strength of basicity showed the best catalytic performance in the cases studied. The mechanism of reaction and catalyst functioning was discussed.
References
Baba T, Fujiwara M, Oosaku A, Kobayashi A, Deleon RG, Ono Y, Appl. Catal. A: Gen., 227(1-2), 1 (2002)
Chen B, Chuang SSC, J. Mol. Catal. A-Chem., 195, 37 (2003)
Davis TL, Blanchard KC, "Phenylurea and Sym-Diphenylurea," Organic Syntheses CV1, 453
Frulla FF, Stuber AF, Whiteman JP, U.S. Patent, 4,550,188 (1985)
Fu ZH, Ono Y, J. Mol. Catal., 91, 399 (1994)
Giannoccaro P, Inorg. Chim. Acta, 142, 81 (1988)
Gurgiolo AE, U.S. Patent, 4,268,684 (1981)
Ikariya T, Shokubai, 31, 271 (1989)
Kim HS, Kim YJ, Lee H, Lee SD, Chin CS, J. Catal., 184(2), 526 (1999)
Katada N, Fujinaga H, Nakamura Y, Okumura K, Nishigaki K, Niwa M, Catal. Lett., 80(1-2), 47 (2002)
Lee JS, Woo JW, Lee CW, Hong KS, Yeo JK, Korean J. Chem. Eng., 7(2), 145 (1990)
Niwa M, Suzuki K, Kishida M, Murakami Y, Appl. Catal., 67, 297 (1991)
Oh JS, Lee SM, Yeo JK, Lee CW, Lee JS, Ind. Eng. Chem. Res., 30, 1456 (1991)
Paul F, Coordination Chem. Rev., 203, 269 (2000)
Smith RM, "Lucky Non-phosgenation Process: MDI and PMPPI by Carbonylation," PEP Review 94-1-2, SRI International (1995)
Solmons GTW, "Organic Chemistry," 3rd ed., John Wiley (1984)
Wan BS, Liao SJ, Yu DR, Appl. Catal. A: Gen., 183(1), 81 (1999)
Yang Y, Lu SW, Tetrahedron Lett., 40, 4845 (1999)
Chen B, Chuang SSC, J. Mol. Catal. A-Chem., 195, 37 (2003)
Davis TL, Blanchard KC, "Phenylurea and Sym-Diphenylurea," Organic Syntheses CV1, 453
Frulla FF, Stuber AF, Whiteman JP, U.S. Patent, 4,550,188 (1985)
Fu ZH, Ono Y, J. Mol. Catal., 91, 399 (1994)
Giannoccaro P, Inorg. Chim. Acta, 142, 81 (1988)
Gurgiolo AE, U.S. Patent, 4,268,684 (1981)
Ikariya T, Shokubai, 31, 271 (1989)
Kim HS, Kim YJ, Lee H, Lee SD, Chin CS, J. Catal., 184(2), 526 (1999)
Katada N, Fujinaga H, Nakamura Y, Okumura K, Nishigaki K, Niwa M, Catal. Lett., 80(1-2), 47 (2002)
Lee JS, Woo JW, Lee CW, Hong KS, Yeo JK, Korean J. Chem. Eng., 7(2), 145 (1990)
Niwa M, Suzuki K, Kishida M, Murakami Y, Appl. Catal., 67, 297 (1991)
Oh JS, Lee SM, Yeo JK, Lee CW, Lee JS, Ind. Eng. Chem. Res., 30, 1456 (1991)
Paul F, Coordination Chem. Rev., 203, 269 (2000)
Smith RM, "Lucky Non-phosgenation Process: MDI and PMPPI by Carbonylation," PEP Review 94-1-2, SRI International (1995)
Solmons GTW, "Organic Chemistry," 3rd ed., John Wiley (1984)
Wan BS, Liao SJ, Yu DR, Appl. Catal. A: Gen., 183(1), 81 (1999)
Yang Y, Lu SW, Tetrahedron Lett., 40, 4845 (1999)