Synthesis of Z-1,1,1,4,4,4-hexafluoro-2-butene from hexachlorobutadiene

Chengping Zhang, Xiaoqing Jia, Hengdao Quan*

*Corresponding author for this work

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Abstract

A novel synthetic route of Z-1,1,1,4,4,4-hexafluoro-2-butene (Z-HFO-1336mzz)was developed. It contains three-step reactions as follows: (1) The vapor-phase catalytic fluorination from hexachlorobutadiene to (E/Z)-2,3-dichlorohexafluoro-2-butenepromoted by Cr-based catalyst; (2) The liquid-phase dechlorination reaction from (E/Z)-2,3-dichlorohexafluoro-2-butene to 1,1,1,4,4,4-hexafluoro-2-butyne with Zn in DMF; (3) The gas-phase hydrogenation reaction from 1,1,1,4,4,4-hexafluoro-2-butyne to Z-HFO-1336mzz promoted by Pd + Bi/PAF (porous aluminium fluoride) catalyst. It provided a potential method for industrial production of Z-HFO-1336mzz.

Original languageEnglish
Pages (from-to)77-83
Number of pages7
JournalJournal of Fluorine Chemistry
Volume191
DOIs
Publication statusPublished - 1 Nov 2016
Externally publishedYes

Keywords

  • Chlorofluorination
  • Dechlorination
  • Hexachlorobutadiene
  • Hydrogenation
  • Z-1,1,1,4,4,4-hexafluoro-2-butene

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Zhang, C., Jia, X., & Quan, H. (2016). Synthesis of Z-1,1,1,4,4,4-hexafluoro-2-butene from hexachlorobutadiene. Journal of Fluorine Chemistry, 191, 77-83. https://doi.org/10.1016/j.jfluchem.2016.09.012