Synthesis of 3,3,3-trifluoropropyne from chlorotrifluoropropene isomers in liquid phase

Tongyun Zhang, Chengping Zhang, Xiaoxun Ma*, Hengdao Quan

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

Chlorotrifluoropropene isomers including 1‑chloro-3,3,3-trifluoroproene (HCFO-1233zd(Z/E)) and 2‑chloro-3,3,3-trifluoropropene (HCFO-1233xf) were adopted as the dehydrochlorination materials to produce 3,3,3-trifluoropropyne (TFPY) by one-pot method were reported. The experimental data indicated that HCFO-1233zd(Z) was the most favorable synthetic raw material in this process, followed by HCFO-1233xf, and HCFO-1233zd(E) then. However, DFT calculations demonstrated the superiority of HCFO-1233zd(E) to HCFO-1233xf according to the reaction energy barrier. By further referring to the thermodynamic calculations and the computed water solubility, the reaction priority herein was identified as HCFO-1233zd(Z) > HCFO-1233xf > HCFO-1233zd(E). Therefore, compared to kinetic effects, the reactivity of HCFO-1233zd(Z/E) and HCFO-1233xf was evidently determined by their thermodynamic properties and solubility. This work thus provides guidance for similar hydrogen halide removal in liquid phase.

Original languageEnglish
Article number109950
JournalJournal of Fluorine Chemistry
Volume255-256
DOIs
Publication statusPublished - Mar 2022

Keywords

  • 1‑chloro‑3,3,3-trifluoroproene
  • 2‑chloro‑3,3,3-trifluoropropene
  • 3,3,3-trifluoropropyne
  • DFT
  • Dehydrochlorination

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