Citation: FENG Yue-lan, WANG Jun-wei, LI Qi-feng, KANG Mao-qing, WANG Xin-kui. Synthesis of methyl N-phenyl carbamate from phenyl urea and methanol over the KF/Al₂O₃ catalyst[J]. Journal of Fuel Chemistry and Technology, ;2013, 41(12): 1507-1511. shu

Synthesis of methyl N-phenyl carbamate from phenyl urea and methanol over the KF/Al₂O₃ catalyst

1.
Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China

Corresponding author: FENG Yue-lan,
Received Date: 11 May 2013
Available Online: 29 July 2013

The solid alkaline catalysts of supported potassium halides were prepared by impregnation method and used in the methanolysis of phenyl urea with methanol to synthesize methyl N-phenyl carbamate (MPC); the influence of oxide supports and potassium halides on the catalyst performance was investigated. The results indicated that KF/Al₂O₃ exhibits high catalytic activity and selectivity to MPC; the KF/Al₂O₃ catalyst containing 50% KF and calcined at 500 ℃ for 4 h performs best in the methanolysis of phenyl urea, over which the conversion of phenyl urea and selectivity to MPC reach 96.5% and 86.3%, respectively. The XRD results proved that KF and Al₂O₃ are partially transformed to K₃AlF₆ due to the strong interaction between KF and Al₂O₃. Both KF and K₃AlF₆ are active for the activation of methanol and selective conversion of phenyl urea; the excellent performance of KF/Al₂O₃ catalyst in the methanolysis of phenyl urea to MPC can be ascribed to the synergy of KF and K₃AlF₆.
- KF/Al₂O₃,
- methyl N-phenyl carbamate,
- phenyl urea,
- methanol
1. [1]
  [1] MIZUNO T, ALPER H. Reductive carbonylation of nitrobenzenes catalyzed by a new binuclear rhodium complex[J]. J Mol Catal A: Chem, 1997, 121: 119-122.
2. [2]
  [2] SHI F, DENG Y. Polymer-immobilized gold catalysts for the efficient and clean syntheses of carbamates and symmetric ureas by oxidative carbonylation of aniline and its derivatives[J]. J Catal, 2002, 211(2): 548-551.
3. [3]
  [3] FU Z H, ONO Y. Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts[J]. J Mol Catal, 1994, 91(3): 399-405.
4. [4]
  [4] LI Q F, WANG J W, DONG W S, KANG M Q, WANG X K, PENG S Y. A phosgene-free process for the synthesis of methyl N-phenyl carbamate by the reaction of aniline with methyl carbamate[J]. J Mol Catal, 2004, 212(2): 99-105.
5. [5]
  [5] WANG J W, LI Q F, DONG W S, KANG M Q, WANG X K, PENG S Y. A new non-phosgene route for synthesis of methyl N-phenyl carbamate from phenylurea and methanol[J]. Appl Catal A: Gen, 2004, 261(2): 191-195.
6. [6]
  [6] 秦飞, 李其峰, 王军威, 冯月兰, 亢茂青, 朱玉雷, 王心葵. 苯胺、尿素、甲醇一步法合成苯氨基甲酸甲酯[J]. 精细化工, 2008, 25(8): 825-828. (QIN Fei, LI Qi-feng, WANG Jun-wei, FENG Yue-lan, KANG Mao-qing, ZHU Yu-lei, WANG Xin-kui. Synthesis of methyl N-phenyl carbamate from aniline, urea and methanol[J]. Fine Chemicals, 2008, 25(8): 825-828.)
7. [7]
  [7] 刘航飞, 李会泉, 柳海涛, 叶红齐. 甲氧基铅催化合成苯氨基甲酸甲酯[J]. 石油化工, 2009, 38(2): 145-148. (LIU Hang-fei, LI Hui-quan, LIU Hai-tao, YE Hong-qi. Synthesis of methyl N-phenyl carbamate catalyzed by lead methylate[J]. Petrochemical Technology, 2009, 38(2): 145-148.)
8. [8]
  [8] 史芸, 张广林, 王胜平, 马新宾. 由碳酸二甲酯合成异氰酸酯[J]. 石油学报(石油加工), 2010, 26(4): 648-656. (SHI Yun, ZHANG Guang-lin, WANG Sheng-ping, MA Xin-bin. Synthesis of isocyanate from dimethyl carbonate[J]. Acta Petrolei Sinica (Petroleum Processing Section), 2010, 26(4): 648-656.)
9. [9]
  [9] 孙述文, 王高峰, 崔桂花, 白羽. KF/Al₂O₃催化的有机化学反应研究进展[J]. 吉林医药学院学报, 2010, 31(4): 226-229. (SUN Shu-wen, WANG Gao-feng, CUI Gui-hua, BAI Yu. Progress on study of organic synthesis catalyzed by KF/Al₂O₃[J]. Journal of Jilin Medical College, 2010, 31(4): 226-229.)
10. [10]
  [10] HATTORI H. Heterogeneous basic catalysis[J]. Chem Rev, 1995, 95: 537-558.
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沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis of methyl N-phenyl carbamate from phenyl urea and methanol over the KF/Al2O3 catalyst

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通讯作者: 陈斌, bchen63@163.com

Synthesis of methyl N-phenyl carbamate from phenyl urea and methanol over the KF/Al₂O₃ catalyst