Synthesis of 1,1,2,2,3,3,4-heptafluorocyclopentane as a new generation of green solvent

• Published in: Journal of fluorine chemistry 2016-01, Vol.181, p.11-16
• Main Authors: Zhang, Chengping, Qing, Feiyao, Quan, Hengdao, Sekiya, Akira
• Format: Article
• Language: English
• Subjects: 1,1,2,2,3,3,4,4,5-Heptafluorocyclopentane; 1-Chloroheptafluorocyclopentene; Fluorination; Green solvent; Hydrogenation
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2015.10.012

1,1,2,2,3,3,4-Heptafluorocyclopentane was synthesized by the liquid-phase fluorination reaction from hexachlorocyclopentadiene to chloroheptafluorocyclopentene via a series of intermediates in the presence of KF in DMF and the vapor-phase hydrogenation reaction of 1-chloroheptafluorocyclopentene in the presence of Pd-based hydrogenation catalysts. •1,1,2,2,3,3,4-Heptafluorocyclopentene was first synthesized comprehensively.•The reactivity of various chlorine was arranged in the liquid-phase fluorination.•Chemical equilibriums between isomers were verified by quantum chemical calculations.•The mechanisms for 1,1,2,2,3,3,4-heptafluorocyclopentane synthesis were proposed. 1,1,2,2,3,3,4-Heptafluorocyclopentane is a new generation of green solvent. It was synthesized by the liquid-phase fluorination reactions from hexachlorocyclopentadiene to 1-chloroheptafluoro-cyclopentene in the presence of KF in DMF and by the vapor-phase hydrogenation reaction from 1-chloroheptafluorocyclopentene to 1,1,2,2,3,3,4-heptafluorocyclopentane in the presence of Pd-based hydrogenation catalyst. Quantum chemical calculations for the isomers energies using Gaussian09 were conducted to verify the chemical equilibriums between isomers of trichloropentafluorocyclopentene or dichlorohexafluorocyclopentene in the fluorination reactions. Possible mechanisms for 1,1,2,2,3,3,4-heptafluorocyclopentane synthesis were proposed.