Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate

Jianxun Dong; Xiaoguang Zheng; Xiaohui Li; Xiaopeng Zhang; Xiaoyan Feng

doi:doi:10.11648/j.ajaic.20180202.12

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Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate

Jianxun Dong, Xiaoguang Zheng, Xiaohui Li, Xiaopeng Zhang, Xiaoyan Feng

Published in American Journal of Applied and Industrial Chemistry (Volume 2, Issue 2)

Received: 6 September 2018 Accepted: 9 October 2018 Published: 23 October 2018

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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.

Published in	American Journal of Applied and Industrial Chemistry (Volume 2, Issue 2)
DOI	10.11648/j.ajaic.20180202.12
Page(s)	15-19
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2018. Published by Science Publishing Group

Keywords

1,3-Bis (Isocyanatomethyl) Benzene; Bis(Triehloromethyl)Carbonate; M-Xylylenediamine; Optimization

References

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[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.

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APA Style

Jianxun Dong, Xiaoguang Zheng, Xiaohui Li, Xiaopeng Zhang, Xiaoyan Feng. (2018). Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate. American Journal of Applied and Industrial Chemistry, 2(2), 15-19. https://doi.org/10.11648/j.ajaic.20180202.12

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ACS Style

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. Am. J. Appl. Ind. Chem. 2018, 2(2), 15-19. doi: 10.11648/j.ajaic.20180202.12

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AMA Style

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. Am J Appl Ind Chem. 2018;2(2):15-19. doi: 10.11648/j.ajaic.20180202.12

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@article{10.11648/j.ajaic.20180202.12,
  author = {Jianxun Dong and Xiaoguang Zheng and Xiaohui Li and Xiaopeng Zhang and Xiaoyan Feng},
  title = {Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate},
  journal = {American Journal of Applied and Industrial Chemistry},
  volume = {2},
  number = {2},
  pages = {15-19},
  doi = {10.11648/j.ajaic.20180202.12},
  url = {https://doi.org/10.11648/j.ajaic.20180202.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajaic.20180202.12},
  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.},
 year = {2018}
}

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TY  - JOUR
T1  - Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate
AU  - Jianxun Dong
AU  - Xiaoguang Zheng
AU  - Xiaohui Li
AU  - Xiaopeng Zhang
AU  - Xiaoyan Feng
Y1  - 2018/10/23
PY  - 2018
N1  - https://doi.org/10.11648/j.ajaic.20180202.12
DO  - 10.11648/j.ajaic.20180202.12
T2  - American Journal of Applied and Industrial Chemistry
JF  - American Journal of Applied and Industrial Chemistry
JO  - American Journal of Applied and Industrial Chemistry
SP  - 15
EP  - 19
PB  - Science Publishing Group
SN  - 2994-7294
UR  - https://doi.org/10.11648/j.ajaic.20180202.12
AB  - 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.
VL  - 2
IS  - 2
ER  -

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Author Information

Jianxun Dong

Department of Nylon Chemical Research Institute, State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, 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
Xiaopeng Zhang

Department of Nylon Chemical Research Institute, State Key Laboratory of Coking Coal Exploitation and Comprehensive Utilization, Pingdingshan, China
Xiaoyan Feng

Department of Nylon Product Development Center, Henan Key Laboratory of Polyamide and Intermediates, Pingdingshan, China

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APA Style

Jianxun Dong, Xiaoguang Zheng, Xiaohui Li, Xiaopeng Zhang, Xiaoyan Feng. (2018). Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate. American Journal of Applied and Industrial Chemistry, 2(2), 15-19. https://doi.org/10.11648/j.ajaic.20180202.12

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ACS Style

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. Am. J. Appl. Ind. Chem. 2018, 2(2), 15-19. doi: 10.11648/j.ajaic.20180202.12

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AMA Style

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. Am J Appl Ind Chem. 2018;2(2):15-19. doi: 10.11648/j.ajaic.20180202.12

Copy | Download

@article{10.11648/j.ajaic.20180202.12,
  author = {Jianxun Dong and Xiaoguang Zheng and Xiaohui Li and Xiaopeng Zhang and Xiaoyan Feng},
  title = {Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate},
  journal = {American Journal of Applied and Industrial Chemistry},
  volume = {2},
  number = {2},
  pages = {15-19},
  doi = {10.11648/j.ajaic.20180202.12},
  url = {https://doi.org/10.11648/j.ajaic.20180202.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajaic.20180202.12},
  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.},
 year = {2018}
}

Copy | Download

TY  - JOUR
T1  - Study on the Optimization of 1,3-Bis (Isocyanatomethyl) Benzene Synthesis with Bis (Trichloromethyl) Carbonate
AU  - Jianxun Dong
AU  - Xiaoguang Zheng
AU  - Xiaohui Li
AU  - Xiaopeng Zhang
AU  - Xiaoyan Feng
Y1  - 2018/10/23
PY  - 2018
N1  - https://doi.org/10.11648/j.ajaic.20180202.12
DO  - 10.11648/j.ajaic.20180202.12
T2  - American Journal of Applied and Industrial Chemistry
JF  - American Journal of Applied and Industrial Chemistry
JO  - American Journal of Applied and Industrial Chemistry
SP  - 15
EP  - 19
PB  - Science Publishing Group
SN  - 2994-7294
UR  - https://doi.org/10.11648/j.ajaic.20180202.12
AB  - 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.
VL  - 2
IS  - 2
ER  -

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