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

Chengping Zhang; Feiyao Qing; Hengdao Quan; Akira Sekiya

doi:10.1016/j.jfluchem.2015.10.012

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

Chengping Zhang
, Feiyao Qing
, Hengdao Quan^*
, Akira Sekiya

^*Corresponding author for this work

Beijing Institute of Technology
National Institute of Advanced Industrial Science and Technology

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	11-16
Number of pages	6
Journal	Journal of Fluorine Chemistry
Volume	181
DOIs	https://doi.org/10.1016/j.jfluchem.2015.10.012
Publication status	Published - Jan 2016
Externally published	Yes

Keywords

1,1,2,2,3,3,4,4,5-Heptafluorocyclopentane
1-Chloroheptafluorocyclopentene
Fluorination
Green solvent
Hydrogenation

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10.1016/j.jfluchem.2015.10.012

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@article{302f43650f584c28a05896473e11c41e,

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

abstract = "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.",

keywords = "1,1,2,2,3,3,4,4,5-Heptafluorocyclopentane, 1-Chloroheptafluorocyclopentene, Fluorination, Green solvent, Hydrogenation",

author = "Chengping Zhang and Feiyao Qing and Hengdao Quan and Akira Sekiya",

note = "Publisher Copyright: {\textcopyright} 2015 Published by Elsevier B.V.",

year = "2016",

month = jan,

doi = "10.1016/j.jfluchem.2015.10.012",

language = "English",

volume = "181",

pages = "11--16",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Synthesis of 1,1,2,2,3,3,4-heptafluorocyclopentane as a new generation of green solvent

AU - Zhang, Chengping

AU - Qing, Feiyao

AU - Quan, Hengdao

AU - Sekiya, Akira

PY - 2016/1

Y1 - 2016/1

N2 - 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.

AB - 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.

KW - 1,1,2,2,3,3,4,4,5-Heptafluorocyclopentane

KW - 1-Chloroheptafluorocyclopentene

KW - Fluorination

KW - Green solvent

KW - Hydrogenation

UR - https://www.scopus.com/pages/publications/84947228652

U2 - 10.1016/j.jfluchem.2015.10.012

DO - 10.1016/j.jfluchem.2015.10.012

M3 - Article

AN - SCOPUS:84947228652

SN - 0022-1139

VL - 181

SP - 11

EP - 16

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -

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

Abstract

Keywords

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