Reactions of aliphatic fluoro-alcohols with CHClF2 at atmospheric pressure

被引:17
作者
Mizukado, J [1 ]
Matsukawa, Y [1 ]
Quan, HD [1 ]
Tamura, M [1 ]
Sekiya, A [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Tsuchiura, Ibaraki 3058565, Japan
关键词
difluoromethylation; difluorocarbene; chlorodifluoromethane; fluorinated ether;
D O I
10.1016/j.jfluchem.2005.12.034
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
The reactions of aliphatic fluoro-alcohols with chlorodifluoromethane (CHCIF2) 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. (c) 2006 Elsevier B.V. All rights reserved.
引用
收藏
页码:400 / 404
页数:5
相关论文
共 14 条
[1]
BAGNALL RD, 1978, J FLUORINE CHEM, V11, P93, DOI 10.1016/S0022-1139(00)81010-6
[2]
A SIMPLE CONVENIENT METHOD FOR PREPARATION OF DIFLUOROMETHYL ETHERS USING FLUOROSULFONYLDIFLUORACETIC ACID AS A DIFLUOROCARBENE PRECURSOR [J].
CHEN, QY ;
WU, SW .
JOURNAL OF FLUORINE CHEMISTRY, 1989, 44 (03) :433-440
[3]
FUSS A, 1990, SYNTHESIS-STUTTGART, P604
[4]
[5]
ITAGAKI T, 2003, Patent No. 200312591
[6]
KOLYCHEVA MT, 1991, J ORG CHEM USSR, V27, P670
[7]
Selective production of difluoromethyl methyl ether from chlorodifluoromethane using alkali metal carbonates [J].
Lee, HJ ;
Kim, HS ;
Lee, SD ;
Lee, WK ;
Kim, HG .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (01) :133-136
[8]
Insertion reactions of difluorocarbene generated by pyrolysis of hexafluoropropene oxide to O-H bond [J].
Mizukado, J ;
Matsukawa, Y ;
Quan, HD ;
Tamura, M ;
Sekiya, A .
JOURNAL OF FLUORINE CHEMISTRY, 2005, 126 (03) :365-369
[9]
PLUDNENKO VG, 1984, J ORG CHEM USSR, V20, P2261
[10]
The potential of hydrofluoroethers to replace CFCs, HCFCs and PFCs [J].
Sekiya, A ;
Misaki, S .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 101 (02) :215-221