Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate
American Journal of Applied and Industrial Chemistry
Volume 2, Issue 2, December 2018, Pages: 15-19
Received: Sep. 6, 2018; Accepted: Oct. 9, 2018; Published: Oct. 23, 2018
Views 1007      Downloads 98
Authors
Jianxun Dong, Department of Nylon Chemical Research Institute, State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, China; Department of Ministry of Technology, Shenma Industrial Co., Ltd, Pingdingshan, China; Department of Nylon Research Institute, China Pingmei Shenma Group Energy and Chemical Research Academy, Pingdingshan, China
Xiaoguang Zheng, Department of Ministry of Technology, Shenma Industrial Co., Ltd, Pingdingshan, China
Xiaohui Li, Department of Nylon Chemical Research Institute, State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, China; Department of Nylon Research Institute, China Pingmei Shenma Group Energy and Chemical Research Academy, Pingdingshan, China
Xiaopeng Zhang, Department of Nylon Chemical Research Institute, State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, China; Department of Nylon Research Institute, China Pingmei Shenma Group Energy and Chemical Research Academy, Pingdingshan, China
Xiaoyan Feng, Department of Nylon Product Development Center, Henan Key Laboratory of Polyamide and Intermediates, Pingdingshan, China
Article Tools
Follow on us
Abstract
1,3-Bis(isocyanatomethyl)benzene is an isocyanate with high quality performance, excellent yellowing resistance and weather resistance. It has wide application in optical polymer composite materials, construction, automotive and other industries. The current production process is mainly prepared by the liquid phase reaction of m-xylylenediamine with highly toxic phosgene. Due to the particularity of phosgene, the synthesis and application of 1,3-bis(isocyanatomethyl)benzene is greatly restricted, the production threshold and the price remains high, which seriously affects the promotion of products. Exploring the non-phosgene green synthesis process for the preparation of 1,3-bis(isocyanatomethyl)benzene is one of hotspots in the isocyanate research and development. The research target of this paper is to explore a safe, convenient and environmentally friendly synthesis route for 1,3-bis(isocyanatomethyl) benzene. The synthesis optimization of 1,3-Bis(isocyanatomethyl) benzene from m-xylylenediamine and bis(trichloromethyl) Carbonate was comprehensively studied. Factors such as molar ratio of raw materials, reaction temperature, reaction time and nitrogen rate were also studied. The optimal conditions were as follows: the molar ratio of m-xylylenediamine to bis(triehloromethyl)carbonate was 1.2:1.0, the nitrogen gas velocity was 8 mL·min-1, the reaction temperature was 125°C and the reaction time was 8.0 hours. Under the optimum condition, the 1,3-Bis (isocyanatomethyl) benzene yield was 83.35%. The reaction mechanism and the key steps involved in the reaction process were also deeply analyzed.
Keywords
1,3-Bis (Isocyanatomethyl) Benzene; Bis(Triehloromethyl)Carbonate; M-Xylylenediamine; Optimization
To cite this article
Jianxun Dong, Xiaoguang Zheng, Xiaohui Li, Xiaopeng Zhang, Xiaoyan Feng, Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate, American Journal of Applied and Industrial Chemistry. Vol. 2, No. 2, 2018, pp. 15-19. doi: 10.11648/j.ajaic.20180202.12
Copyright
Copyright © 2018 Authors retain the copyright of this article.
This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
References
[1]
Harry, B. and Andrew, G. Z., The Chemistry of Phosgene, Journal of Chemical Reviews, 1973,73(1):75-79.
[2]
Liu, Y. H., Zhao, H. and Li, G. P., et al., Isocyanate, Chemical Industry Press. Beijing, 2004, p p.58-65.
[3]
Ding, J. S., Shi, B. and Shang, Y. H., et al., Preparation of m-Xylylene Diisocyanate Based on Salt-Forming Phosgene Gas Reaction, CN 102070491, 2013-12-18.
[4]
Li, C., Dong, J. X. and Guo, X. Z., et al., Synthesis device and method for m-xylylene diisocyanate, CN 1025195080, 2017-10-20.
[5]
Nagata, H., Wada, S. and Mizuta, H., Preparation Method of Xylylene Diisocyanate, CN 1038503, 1998-05-27.
[6]
Zhang, J. Y., Lei, L. L. and Wang, Y., et al., Development of phosgene production technology and phosgenation product development, Chinese Journal of Pesticides, 2004, 43(6): 245-248.
[7]
Ma, D. Q., Ding, J. S. and Song, J. H., The progress of organic isocyanate production technology, Chinese Journal of Chemical Industry Development, 2007, 26(5): 668-673.
[8]
Wang, X. H., He, Y. N. and Pan, M. D., Synthesis of Substituted Phenyl Isocyanates by Triphosgene Method, Chinese Journal of Applied Chemicals, 2008, 37(9):1019-1021.
[9]
Wang, B., Yu, C. M. and Chen, Z. W., et al., An efficient method for the synthesis of dialkyl chlorophosphates from trialkyl phosphites using bis(trichloromethyl) carbonate, Chinese Journal of Chemical Letters, 2008, 19(8): 904-906.
[10]
Weng, Y. Y., Li, J. J. and Su., W. K., An approach to synthesis of (Z)-2-chloro-1,3-diarylpropen-1-ones by Vilsmeier reagent (bis-(trichloromethyl) carbonate/DMF), Chinese Journal of Chemical Letters, 2011, 22(12): 1395-1398.
[11]
Ayala, C. E., Villalpando, A. and Nguyen, A. L., et al., Chlorination of Aliphatic Primary Alcohols via Triphosgene–Triethylamine Activation, Journal of Organic Letters, 2012, 14(14): 3676-3679.
[12]
Villalpando, A., Ayala, C. E. and Watson, C. B., et al., Triphosgene–Amine Base Promoted Chlorination of Unactivated Aliphatic Alcohols, Journal of Organic Chemistry, 2013, 78(8):3989-3996.
[13]
Geller, L. T. and Répási. J., Bis(trichloromethyl)carbonate (BTC, Triphosgene): A Safer Alternative to Phosgene, Journal of Organic Process Research & Development, 2017, 21(9):1439-1446.
[14]
Ji, B., Zhai, X. M. and Xu, Y., Reaction mechanism and application of triphosgene, Chinese Journal of Sci-Tech Information Development & Economy, 2009, 13(10):136-137.
[15]
Wang, W. S. and Li. H., Study on synthesis of p-phenylene diisocyanate by triphosgene method, Chinese Journal of Polyurethane Industry, 2011, 26(3):40-44.
[16]
Cotarca, L., Delogu, P. and Nardelli, A., et al., Bis(trichloromethyl) carbonate in organic synthesis, Journal of Synthesis, 1996, (5): 553-576.
[17]
Dong, J. X., Zhang, Y. J. and Li, S. Q., et al., Study on m-xylylene diisocyanate synthesis with triphosgene, ChineseJournal of Chemical Research and Application, 2015, 27(6): 891-894.
ADDRESS
Science Publishing Group
1 Rockefeller Plaza,
10th and 11th Floors,
New York, NY 10020
U.S.A.
Tel: (001)347-983-5186