光谱学与光谱分析 |
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Application of IR Spectrum to the Research on Mechanism of Synthesis of 2,4-Toluene Dicarbamate Catalyzed by Zinc Acetate |
MA Dan,WANG Gui-rong*,WANG Yan-ji,ZHAO Xin-qiang |
Key Laboratory of Green Chemical Technology and High Efficient Energy Saving of Hebei Province, Hebei University of Technology, Tianjin 300130, China |
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Abstract The methoxycarbonylation mechanism of synthesizing 2,4-toluene dicarbamate from 2,4-toluene diamine and dimethyl carbonate catalyzed by anhydrous zinc acetate was investigated by Fourier transform infrared spectroscopy. The result shows that the new coordination complex was formed by oxygen atom of dimethyl carbonate’s carbonyl group attaching to zinc atom of anhydrous zinc acetate to form the Zn—O coordination bond, and the anhydrous zinc acetate changed from a bidentate ligand to a unidentate ligand. Simultaneously, dimethyl carbonate’s carbonyl group was activated. 2,4-toluene diamine was a nucleophilic reagent, and it’s amidos attacked the activated carbon of dimethyl carbonate’s carbonyl group in the new coordination complex to produce the methoxycarbonylation compound 2,4-toluene dicarbamate, then the Zn—O coordination bond in the new coordination complex was broken. At the same time, the anhydrous zinc acetate returned to a bidentate ligand.
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Received: 2007-08-10
Accepted: 2007-11-20
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Corresponding Authors:
WANG Gui-rong
E-mail: wangguirong111@126.com
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[1] WANG Yan-ji, ZHAO Xin-qiang(王延吉, 赵新强). Green Catalytic Process and Technology(绿色催化过程与工艺). Beijing: Chemical Industry Press(北京:化学工业出版社), 2002. 102. [2] LI Qi-feng, WANG Jun-wei, DONG Wen-sheng, et al(李其峰, 王军威, 董文生, 等). Chemical Journal of Chinese University(高等学校化学学报), 2003, 24(7): 1277. [3] Arthur E Gurgiolo, Lake Jackson. US 4268683, 1981-05-19. [4] Smith R C, Hunns J C. WO 9856758 , 1998-12-17. [5] ZHAO Xin-qiang, WANG Yan-ji, LI Fang, et al(赵新强, 王延吉, 李 芳, 等). Petrochemical Technology(石油化工), 1999, 28(9): 611. [6] Robert G Deleon, Akane K, Tatsuya Y. et al. Applied Catalysis A: General, 2002, 225: 43. [7] XUE Wei, CONG Jing-sheng, LI Fang, et al(薛 伟, 丛津生, 李 芳, 等). Acta Petrolei Sinica, Petroleum Processing Section(石油学报, 石油加工), 2004, 20(2): 35. [8] JING Xu-ying, CHEN Shi-di, YAO En-yun(荆煦英, 陈式棣, 么恩云). Practical Guide of Infrared Spectrum(红外光谱实用指南). Tianjin: Science and Technology Press(天津:科学技术出版社), 1992. 92. [9] LI Xiao-jun, HU Ke-liang, HUANG Yun-lan, et al(李小俊, 胡克良, 黄允兰, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2002, 22(3): 392. [10] Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compound(无机和配位化合物的红外和拉曼光谱). Translated by HUANG De-ru, WANG Ren-qing(黄德如, 汪仁庆,译). Beijing: Chemical Industry Press(北京: 化学工业出版社), 1986. 257. [11] MEI Yan, NIE Zuo-ren, WANG Wei(梅 燕, 聂祚仁, 王 为). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2007, 27(2): 254. [12] Bachari E M, Baud G, Amor S Ben,et al. Thin Solid Film, 1999, 348: 165. [13] Pierre Deslongchamps. Stereoelectronic Effects in Organic Chemistry(有机化学中的立体电子效应). Translated by LI Guo-qing, FANG Xiu-hua(李国清, 房秀华,译). Beijing: Peking University Press(北京: 北京大学出版社), 1991. 52. [14] Morrison R T, Boyd R. N. Organic Chemistry(有机化学). Translated by Organic Chemistry Teaching Groups of Fudan University(复旦大学化学系有机教研组译). Beijing: Science Press(北京: 科学出版社), 1980. 725. [15] XIAO Fu-kui, ZHANG De-sheng, DONG Qing-nian, et al(肖福魁, 张德胜, 董庆年, 等). Chinese Journal of Catalysis(催化学报), 2006, 27(7): 573. |
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