Central Glass Company, Limited

Mari Imamura

Akihiro Ishii

Takashi Ootsuka

Shunsuke Mimura

Koji Ueda

Takayuki Nishimiya

Kazuto Kimura

Takashi Masuda

Takehisa Ishimaru

Hiroshi Minesaki

Masato Kimura

A production method of &#x3b1;,&#x3b1;-difluoroacetaldehyde according to the present invention includes reaction of an &#x3b1;,&#x3b1;-difluoroacetic acid ester with hydrogen gas (H) in the presence of a ruthenium catalyst. It is possible to selectively obtain &#x3b1;,&#x3b1;-difluoroacetaldehyde as a partially reduced product of the hydrogenation reaction by the adoption of specific reaction conditions (in particular, reaction solvent and reaction temperature). This hydrogenation process can be alternative to the industrially unpractical hydride reduction process.

&#x3b1;,&#x3b1;-Difluoroacetaldehyde production method

&#x3b1;,&#x3b1;-difluoroacetaldehyde production method

A production method of a 1,1,1,5,5,5-hexafluoroacetylacetone hydrate according to the present invention includes: step 1: step 1: obtaining a reaction mixture that contains at least 1,1,1,5,5,5-hexafluoro-3-pentyn-2-one or an equivalent thereof by reaction of a 3,3,3-trifluoropropynyl metal with a trifluoroacetate; and step 2: forming the 1,1,1,5,5,5-hexafluoroacetylacetone hydrate by contact of the reaction mixture obtained in the step 1 with water in the presence of an acid. It is possible to produce 1,1,1,5,5,5-hexafluoroacetylacetone by dehydration of the thus-formed hydrate. Thus, the production method according to the present invention is industrially applicable.

Method for producing 1,1,1,5,5,5-hexafluoroacetylacetone

A production process of an &#x3b1;-fluoroaldehyde according to the present invention includes reaction of an &#x3b1;-fluoroester with hydrogen gas (H) in the presence of a ruthenium complex. It is possible in the present invention to allow relatively easy industrial production of the &#x3b1;-fluoroaldehyde and to directly obtain, as stable synthetic equivalents of the &#x3b1;-fluoroaldehyde, not only a hydrate (as obtained by conventional techniques) but also a hemiacetal that is easy to purify and is of high value in synthetic applications. The present invention provides solutions to all problems in the conventional techniques and establishes the significantly useful process for production of the &#x3b1;-fluoroaldehyde.

Process for producing &#x3b1;-fluoroaldehydes

A production method of a &#x3b2;-fluoroalcohol includes performing a reaction of an &#x3b1;-fluoroester with hydrogen gas (H) in the presence of a specific ruthenium complex (i.e. a ruthenium complex of the general formula [2], preferably a ruthenium complex of the general formula [4]). This production method can employ a suitable hydrogen pressure of 1 MPa or less by the use of such a specific ruthenium complex and does not require a high-pressure gas production facility when put in industrial practice. In addition, this production method can remarkably reduce the amount of catalyst used therein (to e.g. a substrate/catalyst ratio of 20,000) in comparison to the substrate/catalyst ratio conventional reduction of &#x3b1;-fluoroalcohol. It is possible by these reduction in hydrogen pressure and catalyst amount to largely reduce the production cost of the &#x3b2;-fluoroalcohol. 

Method for producing &#x3b2;-fluoroalcohol

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Kawagoe, Japan

Mari Imamura