Mechanism of Synthesis of 1,5-Naphthalene Dicarbamate from1,5-Naphthalene Diamine and Dimethyl Carbonate

Chinese Journal of Catalysis ›› 2006, Vol. 27 ›› Issue (7): 573-578.

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Mechanism of Synthesis of 1,5-Naphthalene Dicarbamate from1,5-Naphthalene Diamine and Dimethyl Carbonate

XIAO Fukui1,2,3, ZHANG Desheng3, DONG Qingnian1, WEN Dongmei3, PAN Ling3, JIAO Liping3, WEI Wei1*, SUN Yuhan1

1 State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, The Chinese Academy of Sciences, Taiyuan 030001, Shanxi, China; 2 Graduate University of The Chinese Academy of Sciences, Beijing 100049, China; 3 Research Institute of Jilin Petrochemical Company of Petrochina, Jilin 132021, Jilin, China

Received:2006-07-25 Online:2006-07-25 Published:2006-07-25

Abstract

Abstract: The methoxycarbonylation mechanism of 1,5-naphthalene diamine with dimethyl carbonate catalyzed by zinc acetate was investigated by Fourier transform infrared spectroscopy. Zinc acetate dihydrate was not active for the reaction until it changed into anhydrous zinc acetate by losing the crystal water. Anhydrous zinc acetate activated 1,5-naphthalene diamine by the formation of a new zinc complex. The new complex was a suitable nucleophilic reagent that could react with dimethyl carbonate to produce a methoxycarbonylation compound. When the complex of anhydrous zinc acetate with 1,5-naphthalene diamine was formed, the anhydrous zinc acetate changed from a bidentate ligand to a unidentate ligand.

Key words: 1,5-naphthalene dicarbamate, zinc acetate, 1,5-naphthalene diamine, dimethyl carbonate, reaction mechanism

XIAO Fukui1,2,3, ZHANG Desheng3, DONG Qingnian1, WEN Dongmei3, PAN Ling3, JIAO Liping3, WEI Wei1*, SUN Yuhan1. Mechanism of Synthesis of 1,5-Naphthalene Dicarbamate from1,5-Naphthalene Diamine and Dimethyl Carbonate[J]. Chinese Journal of Catalysis, 2006, 27(7): 573-578.

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Mechanism of Synthesis of 1,5-Naphthalene Dicarbamate from1,5-Naphthalene Diamine and Dimethyl Carbonate

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