Synthesis of methyl N -phenyl carbamate catalyzed by ionic liquid-promoted zinc acetate

Industrial and Engineering Chemistry Research

Volumn 51, Issue 35, 2012, Pages 11335-11340

  Zhao, Xinqiang ^a   Kang, Lijuan ^a   Wang, Na ^a   An, Hualiang ^a   Li, Fang ^a   Wang, Yanji ^a  

^a HEBEI UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANHYDROUS ZINC ACETATE; ANILINE MOLECULES; CARBONYL CARBON; CARBONYL OXYGEN; CATALYTIC PERFORMANCE; COORDINATION STRUCTURES; DIMETHYL CARBONATE; FTIR ANALYSIS; NITROGEN ATOM; REACTION CONDITIONS; UNIDENTATE; ZINC ACETATE; ZINC ATOMS;

ANILINE; CATALYSTS; HYDROGEN BONDS; MODEL PREDICTIVE CONTROL; MOLECULES; OXYGEN; ZINC; ZINC COMPOUNDS;

IONIC LIQUIDS;

EID: 84865854510     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie301246q     Document Type: Article

References (25)

1. Shinsuke, F.; Masazumi, C.; Masashi, K. A novel catalytic synthesis of carbamates by oxidative alkoxycarbonylation of amines in the presence of palladium and iodide J. Chem. Soc., Chem. Commun. 1984, 399
2. Alessio, E.; Mestroni, G. Catalytic reductive carbonylation of aromatic nitro compounds to urethanes promoted by supported palladium activated with 1,10-phenanthroline derivatives J. Organomet. Chem. 1985, 291, 117
3. Hwang, K.; Chen, Y.; Chu, C.; Liao, H. Process for preparing carbonate compounds. European Patent 0709363 A1, 1996.
4. Heitkamper, P.; Konig, K.; Findeisen, K.; Fauss, R.; Sundermann, R. Process for the preparation of N, O -disubstituted urethanes useful for the preparation of isocyanates. U.S. Patent 4430505, 1984.
5. Zhao, X.; Wang, Y.; Wang, S.; Yang, H.; Zhang, J. Synthesis of MDI from dimethyl carbonate over solid catalysts Ind. Eng. Chem. Res. 2002, 41, 5139
6. Li, F.; Miao, J.; Wang, Y.; Zhao, X. Synthesis of methyl N -phenyl carbamate from aniline and dimethyl carbonate over supported zirconia catalyst Ind. Eng. Chem. Res. 2006, 45, 4892
7. Kricsfalussy, Z.; Waldmann, H.; Traenckner, H.-J. Oxycarbonylation of methanol to dimethyl carbonate using molten salts as catalyst Ind. Eng. Chem. Res. 1998, 37, 865
8. Arthur, E. G. Preparation of carbamates from aromatic amines and organic carbonates. U.S. Patent 4268684, 1981.
9. Aldo, B.; Pietro, C.; Fausto, C. Process for the production of aromatic carbamates. U.S. Patent 5698731, 1997.
10. Fu, Z.; Ono, Y. Synthesis of methyl N-phenyl carbamate by methoxycarbonylation of aniline with dimethyl carbonate using Pb compounds as catalysts J. Mol. Catal. 1994, 91, 399
11. Sima, T.; Guo, S.; Shi, F.; Deng, Y. The syntheses of carbamates from reactions of primary and secongdary aliphatic amines with dimethyl carbonate in ionic liquids Tetrahedron Lett. 2002, 43, 8145
12. Zhang, L.; Yang, Y.; Xue, Y.; Fu, X.; An, Y.; Gao, G. Experimental and theoretical investigation of reaction of aniline with dimethyl carbonate catalyzed by acid-base bifunctional ionic liquids Catal. Today 2010, 158, 279
13. Wang, N.; Geng, Y.; Zhao, X.; An, H.; Wang, Y. Synthesis of methyl N -phenyl carbamate catalyzed by ionic liquid and 1,1,3,3-tetramethylguanidine Shiyou Huagong 2008, 37, 1255
14. Fang, D.; Cheng, H.; Gong, K.; Shi, Q.; Zhou, X.; Liu, Z. A green and novel procedure for the preparation of ionic liquid J. Fluorine Chem. 2008, 129, 108
15. Ranu, B. C.; Banerjee, S. Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmim]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles Org. Lett. 2005, 7, 3049
16. 4 and its catalytic performance in the reaction for 4,4″-MDC synthesis J. Mol. Catal. A: Chem. 2007, 276, 168
17. Qin, F.; Li, Q.; Wang, J.; Feng, Y.; Kang, M.; Zhu, Y.; Wang, X. One pot synthesis of methyl N -phenyl carbamate from aniline, urea and methanol Catal. Lett. 2008, 126, 419
18. Li, Q.; Wang, J.; Dong, W.; Wang, X.; Peng, S. Studies on synthesis of methyl N-phenylcarbamate by reaction of aniline and methyl carbamate Chem. J. Chin. Univ. 2003, 24, 1227
19. Xiao, F.; Zhang, D.; Dong, Q.; Wen, D.; Pan, L.; Jiao, L.; Wei, W.; Sun, Y. Mechanism of synthesis of 1,5-naphthalene dicarbamate from 1,5-naphthalene diamine and dimethyl carbonate Cuihua Xuebao 2006, 27, 573
20. Ma, D.; Wang, G.; Wang, Y.; Zhao, X. Application of IR spectrum to the research on mechanism of synthesis of 2,4-toluene dicarbamate catalyzed by zinc acetate Guangpuxue Yu Guangpufenxi 2009, 29, 331
21. Wang, H.; He, G.; Wang, G.; Tan, H. Apparent kinetics and reaction mechanism of synthesis of methyl phenyl carbamate from aniline and dimethyl carbonate Tianranqi Huagong 2009, 34, 7
22. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4 th ed.; Wiley-Interscience: New York, 1997.
23. Schreiner, P. R.; Wittkopp, A. H-bonding additives act like Lewis acid catalysts Org. Lett. 2002, 4, 217
24. Aggarwal, A.; Lancaster, N. L.; Sethi, A. R.; Welton, T. The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids Green Chem. 2002, 4, 517
25. Sun, N.; He, X.; Dong, K.; Zhang, X.; Lu, X.; He, H.; Zhang, S. Prediction of the melting points for two kinds of room temperature ionic liquids Fluid Phase Equilib. 2006, 246, 137