Hydrofluoroether compounds and processes for their preparation and use

A technology of compound and hydrofluoroether, applied in the direction of ether preparation, chemical instruments and methods, lubricating composition, etc., can solve problems such as unsuitable and difficult alkylation reactions of perfluoroketones

Inactive Publication Date: 2009-09-23
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above method is generally not suitable for the preparation of certain types of branched chain HFE (because of the difficulty of alkylation of some branched chain perfluoroketones)

Method used

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  • Hydrofluoroether compounds and processes for their preparation and use
  • Hydrofluoroether compounds and processes for their preparation and use
  • Hydrofluoroether compounds and processes for their preparation and use

Examples

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preparation example Construction

[0222] Preparation of hydrofluoroether compounds

[0223] The hydrofluoroether compound (HFE) of the present invention can be prepared by alkylation of a fluorine-containing alkoxide compound by subjecting a fluorine-containing ketone compound (more specifically, comprising independently A fluorine-containing ketone compound having two end groups of a fluoroalkyl or perfluoroalkyl group and an intervening oxytetrafluoroethylene moiety bonded to a carbonyl group through its central carbon atom, each Each of said terminal groups optionally contains at least one catenary heteroatom) with anhydrous alkali metal fluoride (for example, potassium fluoride or cesium fluoride) or anhydrous silver fluoride (preferably in anhydrous polar aprotic solvent Middle) prepared by reaction. See, for example, the preparation methods described in French Patent Publication No. 2,287,432 and German Patent Publication No. 1,294,949, as well as the methods detailed in US Patent No. 5,750,797 (Vitca...

example

[0340] Objects and advantages of this invention are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit this invention. These examples are illustrative only, and are not intended to limit the scope of the appended claims.

[0341] All parts, percentages, ratios, etc. in the examples and in the remainder of the specification are by weight unless otherwise indicated. Solvents and other reagents used were obtained from Sigma-Aldrich Chemical Company, St. Louis, MO (Sigma-Aldrich Chemical Company, St. Louis, MO) unless otherwise indicated.

[0342] In the following examples, a mixture of diastereomers is obtained due to the presence of two (or more) optical centers in the molecule. These diastereomers have boiling points very close to each other and therefore diastereomers cannot be separated by distillation. In some cases, howev...

example 1

[0373] preparation

[0374]

[0375] a- Preparation of intermediate ketones :

[0376]

[0377] Perfluoromorpholinoacetyl fluoride (94.6 g, 65% purity, 0.19 moles), C 3 f 7 OCF=CF 2 (50 g, 0.19 mol), anhydrous diglyme (75 g), potassium fluoride (2.2 g, 0.04 mol), stored in an oven at 125°C, and ground with a mortar and pestle just before use ) and phase transfer catalyst methyltributylammonium methylsulfate (1.2 g, 48% solution in diglyme) were mixed into a 600 mL Parr reaction vessel. The vessel was sealed, heated to 82°C, and maintained at this temperature for 16 hours. After cooling, the vessel was drained, the solid potassium fluoride was filtered, and the resulting biphasic reaction mixture was phase separated. The resulting ketone was purified to a purity of 92% by distillation (b.p. = 145-146°C). The IR spectrum shows 1790.4cm -1 CO absorption at the

[0378] b- Preparation of ethyl ether from intermediate ketones :

[0379] The intermediate ketone ...

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Abstract

A hydrofluoroether compound comprises two terminal, independently fluoroalkyl or perfluoroalkyl groups and an intervening oxytetrafluoroethylidene moiety (-OCF(CF3)-) bonded through its central carbon atom to an alkoxy- or fluoroalkoxy-substituted fluoromethylene moiety (-CF(OR)-), each of the terminal groups optionally comprising at least one catenated heteroatom.

Description

[0001] Cross references to related patent applications [0002] This application claims priority to US Patent Application No. 11 / 567,643, filed December 6, 2006, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] This invention relates to partially fluorinated ether compounds. In other aspects, the present invention also relates to methods for preparing partially fluorinated ether compounds and methods of using them. Background technique [0004] Hydrofluoroethers (HFEs) comprise a class of commercially valuable compounds. Among many applications, hydrofluoroethers have been found suitable as replacements for chlorofluorocarbons (CFCs), which are currently believed to be out of favor and regulated due to their adverse impact on the environment. Unlike CFCs, hydrofluoroether compounds containing fluorine as the only halogen basically do not affect the Earth's ozone layer. This HFE compound is therefore said to exhibit an ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/12C07C41/16C07D307/12C07D295/088C07D295/108C09K5/00B23K35/00B29C44/00C09K3/14
CPCC07D307/18C10N2240/401C10M147/04C07D265/30C09K5/10C07D413/12B23K35/3612C07C43/126C10N2040/22Y10T83/364B23K35/00C07C43/12C07D307/16
Inventor 理查德·M·弗林迈克尔·G·科斯特洛丹尼尔·R·维特卡克
Owner 3M INNOVATIVE PROPERTIES CO
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