Reactions of aliphatic fluoro-alcohols with CHClF2 at atmospheric pressure

Junji Mizukado; Yasuhisa Matsukawa; Heng Dao Quan; Masanori Tamura; Akira Sekiya

doi:10.1016/j.jfluchem.2005.12.034

Reactions of aliphatic fluoro-alcohols with CHClF₂ at atmospheric pressure

Junji Mizukado^*, Yasuhisa Matsukawa, Heng Dao Quan, Masanori Tamura, Akira Sekiya

^*Corresponding author for this work

National Institute of Advanced Industrial Science and Technology

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

14 Citations (Scopus)

Abstract

The reactions of aliphatic fluoro-alcohols with chlorodifluoromethane (CHClF₂) at atmospheric pressure were examined. In the reaction of CF₃CF₂CH₂OH, the difluoromethylated ether was obtained in moderate yield by using ethers such as 1,4-dioxane, diglyme and THF, or their mixtures with water as a reaction solvent. While acetal and orthoformate were also produced, the selectivity of the difluoromethylated ether could be improved by adding water to the reaction. The effect of water could be explained by the reaction mechanism.

Original language	English
Pages (from-to)	400-404
Number of pages	5
Journal	Journal of Fluorine Chemistry
Volume	127
Issue number	3
DOIs	https://doi.org/10.1016/j.jfluchem.2005.12.034
Publication status	Published - Mar 2006
Externally published	Yes

Keywords

Chlorodifluoromethane
Difluorocarbene
Difluoromethylation
Fluorinated ether

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10.1016/j.jfluchem.2005.12.034

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title = "Reactions of aliphatic fluoro-alcohols with CHClF2 at atmospheric pressure",

abstract = "The reactions of aliphatic fluoro-alcohols with chlorodifluoromethane (CHClF2) at atmospheric pressure were examined. In the reaction of CF3CF2CH2OH, the difluoromethylated ether was obtained in moderate yield by using ethers such as 1,4-dioxane, diglyme and THF, or their mixtures with water as a reaction solvent. While acetal and orthoformate were also produced, the selectivity of the difluoromethylated ether could be improved by adding water to the reaction. The effect of water could be explained by the reaction mechanism.",

keywords = "Chlorodifluoromethane, Difluorocarbene, Difluoromethylation, Fluorinated ether",

author = "Junji Mizukado and Yasuhisa Matsukawa and Quan, {Heng Dao} and Masanori Tamura and Akira Sekiya",

year = "2006",

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language = "English",

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journal = "Journal of Fluorine Chemistry",

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T1 - Reactions of aliphatic fluoro-alcohols with CHClF2 at atmospheric pressure

AU - Mizukado, Junji

AU - Matsukawa, Yasuhisa

AU - Quan, Heng Dao

AU - Tamura, Masanori

AU - Sekiya, Akira

PY - 2006/3

Y1 - 2006/3

N2 - The reactions of aliphatic fluoro-alcohols with chlorodifluoromethane (CHClF2) at atmospheric pressure were examined. In the reaction of CF3CF2CH2OH, the difluoromethylated ether was obtained in moderate yield by using ethers such as 1,4-dioxane, diglyme and THF, or their mixtures with water as a reaction solvent. While acetal and orthoformate were also produced, the selectivity of the difluoromethylated ether could be improved by adding water to the reaction. The effect of water could be explained by the reaction mechanism.

AB - The reactions of aliphatic fluoro-alcohols with chlorodifluoromethane (CHClF2) at atmospheric pressure were examined. In the reaction of CF3CF2CH2OH, the difluoromethylated ether was obtained in moderate yield by using ethers such as 1,4-dioxane, diglyme and THF, or their mixtures with water as a reaction solvent. While acetal and orthoformate were also produced, the selectivity of the difluoromethylated ether could be improved by adding water to the reaction. The effect of water could be explained by the reaction mechanism.

KW - Chlorodifluoromethane

KW - Difluorocarbene

KW - Difluoromethylation

KW - Fluorinated ether

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U2 - 10.1016/j.jfluchem.2005.12.034

DO - 10.1016/j.jfluchem.2005.12.034

M3 - Article

AN - SCOPUS:33645397664

SN - 0022-1139

VL - 127

SP - 400

EP - 404

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

IS - 3

ER -

Reactions of aliphatic fluoro-alcohols with CHClF₂ at atmospheric pressure

Abstract

Keywords

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