FTIR Spectroscopic Studies on Catalytic Mechanism of Lead Compounds in the Reaction of Methylene Dianiline and Dimethyl Carbonate

doi:10.3969/j.issn.0251-0790.2012.03.031

Abstract

Abstract:

The stability and component change of the Pb(OAc)₂?3H₂O catalyst, in the reaction of methylene dianiline(MDA) and dimethyl carbonate(DMC) to synthesize methyl diphenyl dicarbamate(MDC), were studied. The results show that the catalyst converts to be lead carbonate containing amine ligand, which still has a highly activity in the synthesis of MDC. The catalytic mechanism of the lead acetate catalyst was studied by in-situ infrared analysis with a temperature controlled liquid cells. The results show that the coordination ligand of catalyst plays an important role in the formation of intermediate tetrahedron, and the transformation between bidentate and monodentate is one of the key steps in catalysis. A possible reaction mechanism for the methoxycarbonylation reaction was proposed based on the in-situ FTIR analysis.

Key words: Dimethyl carbonate, Lead compound, FTIR spectroscopy, Bidentate coordination, Catalytic mechanism

CLC Number:

O643

TrendMD:

PEI Yi-Xia, LI Hui-Quan, LIU Hai-Tao, ZHANG Yi. FTIR Spectroscopic Studies on Catalytic Mechanism of Lead Compounds in the Reaction of Methylene Dianiline and Dimethyl Carbonate[J]. Chem. J. Chinese Universities, 2012, 33(03): 598.

References

[1] LUO Xiao-Lie(罗筱烈), LIU Jin(刘瑾). Chem. J. Chinese Universities(高等学校化学学报)[J], 1995, 16(5): 799-803
[2] Lewandowski G., Milchert E.. J. Hazard. Mater.[J], 2005, 119: 19-24
[3] Pei Y. X., Li H. Q., Liu H. T., Zhang Q. H., Zhang Y.. Chem. Res. Chinese Universities[J], 2010, 26(4): 550-553
[4] Zhao X. Q., Wang Y. J., Wang S. F., Yang H. J., Zhang J. Y.. Ind. Eng. Chem. Res.[J], 2002, 41: 5139-5144
[5] Ono Y.. Catal. Today[J], 1997, 35: 15-25
[6] Gong J. L., Ma X. B., Wang S. P.. Applied Catalysis A-General[J], 2007, 316: 1-21
[7] Carafa M., Quaranta E.. Mini-Rev. Org. Chem.[J], 2009, 6: 168-183
[8] Vauthey I., Valot F., Gozzi C., Fache F., Lemaire M.. Tetrahedron Lett.[J], 2000, 41: 6347-6350
[9] Guo X. C., Qin Z. F., Fan W. B., Wang G. F., Zhao R. H., Peng S. Y., Wang J. H.. Catal. Lett.[J], 2009, 128: 405-412
[10] Aresta M., Dibenedetto A., Quaranta E.. Green Chemistry[J], 1999, 10: 237-242
[11] Baba T., Kobayashi A., Kawanami Y., Inazu K., Ishikawa A., Echizenn T., Murai K., Aso S., Inomata M.. Green Chem.[J], 2005, 7: 159-165
[12] Qiu Z. G., Wang J. W., Kang M. Q., Li Q. F., Wang X. K.. Catal. Lett.[J], 2008, 124: 243-249
[13] Tonto P., Mekasuwandumrong O., Phatanasri S., Pavarajarn V., Praserthdam P.. Ceram. Int.[J], 2008, 34: 57-62
[14] Fu Z. H., Ono Y.. J. Mol. Catal.[J], 1994, 91: 399-405
[15] Wang S. P., Zhang G. L., Ma X. B., Gong J. L.. Ind. Eng. Chem. Res.[J], 2007, 46: 6858-6864
[16] Pei Y. X., Li H. Q., Liu H. T., Zhang Y.. Ind. Eng. Chem. Res.[J], 2011, 50: 1955-1961
[17] LI Xiao-Jun(李小俊), HU Ke-Liang(胡克良). Spectrosc. Spectral Anal.(光谱学与光谱分析)[J], 2002, 22: 392-395
[18] Deacon G. B., Phillips R. J.. Coord. Chem. Rev.[J], 1980, 33: 227-250
[19] Nakmoto K.; Translated by HUANG Di-Ru(黄的如), WANG Qing-Ren(王庆仁). Infrared and Raman Spectra of Inorganic and Coordination Compounds(无机和配位化合物的红外和拉曼光谱)[M], Beijing: Chemical Industry Press, 1986: 235-255, 126-150
[20] Colin S. R.. Method for the Preparation of Carbamates, WO 9855450, 1998-12-10