Highly Selective Gas-phase Synthesis of 1,1-Dichloroethylene from 1,1,2-Trichloroethane over Supported Amine Catalysts

doi:10.1007/s40242-015-5172-5

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (5): 787-791.doi: 10.1007/s40242-015-5172-5

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Highly Selective Gas-phase Synthesis of 1,1-Dichloroethylene from 1,1,2-Trichloroethane over Supported Amine Catalysts

TANG Cen¹, JIN Yanxia¹, WANG Xiaoxia¹, HU Gengshen¹, XIE Guanqun^1,2, LI Xiaonian², LUO Mengfei¹

1. Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, Jinhua 321004, P. R. China;
2. Industrial Catalysis Institute of Zhejiang University of Technology, Hangzhou 310014, P. R. China

Received:2015-04-28 Revised:2015-06-01 Online:2015-10-01 Published:2015-09-08
Contact: XIE Guanqun, E-mail: gqxie@zjnu.edu.cn; LUO Mengfei, E-mail: mengfeiluo@zjnu.cn E-mail:gqxie@zjnu.edu.cn;mengfeiluo@zjnu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.NSFC-21476207), and the Open Research Fund of Top Key Discipline of Chemistry in Zhejiang Provincial Colleges(Zhejiang Normal University), China(No.ZJHX201413).

Abstract

Abstract:

The manufacture of 1,1-dichloroethylene(1,1-DCE) usually employs liquid phase method to perform the dehydrochlorination of 1,1,2-trichloroethane(TCE), where large amounts of high-concentration salty wastewater is produced inevitably. It has been a long-term goal to achieve the gas phase synthesis of 1,1-DCE via supported catalysts. In this work, the gas-phase synthesis of 1,1-DCE from TCE was studied in the presence of pentaethylenehexamine(PEHA) supported on silica. High and stable selectivity to 1,1-DCE(up to 98%) was obtained, which could be ascribed to the relatively strong basicity of PEHA according to a proposed E2 mechanism. The formation of PEHA chloride from the HCl generated in situ was detected and was considered to be the main reason for the deactivation of PEHA catalyst.

Key words: 1,1-Dichloroethene, Supported amine catalyst, Dehydrochlorination

TANG Cen, JIN Yanxia, WANG Xiaoxia, HU Gengshen, XIE Guanqun, LI Xiaonian, LUO Mengfei. Highly Selective Gas-phase Synthesis of 1,1-Dichloroethylene from 1,1,2-Trichloroethane over Supported Amine Catalysts[J]. Chemical Research in Chinese Universities, 2015, 31(5): 787-791.

References

[1] Steven M. D., Hotchkiss J. H., Packag. Technol. Sci., 2002, 15, 17
[2] Chaliha M., Cusack A., Currie M., Sultanbawa Y., Smyth H., J. Agric. Food. Chem., 2013, 61, 5738
[3] Zhang Z. J., Lv Z. Y., Li Z. S., Sun C. C., Chem. J. Chinese Universities, 2008, 29(11), 2273
[4] He H. Y., Li W. L., Xie Z. G., Jing X. B., Huang Y. B., Chem. Res. Chinese Universities, 2014, 30(2), 310
[5] Milchert E., Pazdzioch W., Ind. Eng. Chem. Res., 1999, 38, 391
[6] Katayama K., Yoshida N., Hino T., Method for Manufacturing Vinylidene Chloride, JP 04338341A, 1992
[7] Zhang H. P., Pan Q. Z., Zou Y. C., Chem. J. Chinese Universities, 2014, 35(6), 1307
[8] Liu C., Zhuo X., Cheng H., Liu C., Liu X. H., Chem. J. Chinese Universities, 2015, 36(5), 831
[9] Svoboda J., Ondrus I., Mazanec J., Trgina E., Petrochemia, 1982, 22, 21
[10] Reed D. J., Snedecor T. G. Jr., Manufacture of Vinylidene Chloride with Recycling of Phase-transfer Catalyst, WO 9505352 A1, 1995
[11] Wang X. F., Liu P., Tian Y., Micropor. Mesopor. Mater., 2011, 142, 334
[12] Tian Y., Wang X. F., Pan Y. F., J. Hazard. Mater., 2012, 213/214, 361
[13] Yuan X., Jiang P., Song H., Feng D., Method for Preparation of Vinylidene Chloride by Gas phase Catalytic Cracking of Trichloroethane, CN 102030608 A, 2011
[14] Mochida I., Uchino A., Fujitsu H., Takeshita K., Chem. Lett., 1975, 745
[15] Mochida I., Uchino A., Fujitsu H., Takeshita K., J. Catal., 1978, 51, 72
[16] Mochida I., Watanabe H., Uchino A., Fujitsu H., Takeshita K., Furuno M., Sakura T., Nakajima H., J. Mol. Catal., 1981, 12, 359
[17] Mochida I., Miyazaki T., Takagi T., Fujitsu H., Chem. Lett., 1985, 833
[18] Zoltanski A., Lach J., Pokorska Z., Halaburdo N., Chemik, 1989, 42, 102
[19] Zoltanski A., Lach J., Halaburdo N., Pokorska Z., Przemysl Chemiczny, 1990, 69, 112
[20] Zoltanski A., Lach J., Pokorska Z., Halaburdo N., Czelakowski W., Przemysl Chemiczny, 1990, 69, 309
[21] Fujitsu H., Takagi T., Mochida I., Bull. Chem. Soc. Jpn., 1985, 58, 1589
[22] Serhuchev Y. O., Bilokopytov Y. V., Chernobaev I., Composition for the Vapor Phase Dehydrohalogenation of 1,1,2-Trihaloethane to 1,1-Dihaloethylene and Methods for Preparing and Using Such Composition, US 2008242902Al, 2008
[23] Reed D. J., Snedecor T. G., Dehydrohalogenation of 1,1,2-Trichloroethane Using Cyclic Amines, US 5210344A, 1993
[24] Feng X. X., Xie J., Hu G. S, Jia A. P., Xie G. Q., Luo M. F., Acta Phys. Chim. Sin., 2013, 29, 1266
[25] Cai W., Tan L., Yu J., Jaroniec M., Liu X., Cheng B., Verpoort F., Chem. Eng. J., 2014, 239, 207
[26] Yu J. G., Le Y., Cheng B., RSC Adv., 2012, 2, 6784
[27] Feng X. X., Hu G. S., Hu X., Xie G. Q., Xie Y. L., Lu J. Q., Luo M. F., Ind. Eng. Chem. Res., 2013, 52, 4221
[28] Mochida I., Anju Y., Yamamoto H., Kato A., Seiyama T., Bull. Chem. Soc. Jap., 1971, 44, 3305
[29] Cockerill A. F., Harrison R. G.; Ed.:Patai S., The Chemistry of Double-bonded Functional Groups, Part 1, Wiley, New York, 1977, Chapter 4
[30] Saunders W. H., J., Cockerill A. F., Mechanisms of Elimination Reactions, Wiley, New York, 1973

Highly Selective Gas-phase Synthesis of 1,1-Dichloroethylene from 1,1,2-Trichloroethane over Supported Amine Catalysts

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