Central Glass Company, Limited

Tokyo Institute of Technology

Calsonic Kansei Corporation

Takashi Ootsuka

Akihiro Ishii

Koji Ueda

Manabu Yasumoto

Kenjin Inomiya

Yokusu Kuriyama

Masatomi Kanai

Mari Imamura

Hideyuki Tsuruta

Kaori Mogi

Shunsuke Mimura

Takayuki Nishimiya

Kazuto Kimura

Takeshi Ogasawara

Hiroki Yoshioka

Koichi Mikami

Mikihiro Takahashi

Satoru Miyazawa

Michitaka Ootani

Takao Ikariya

Naohisa Kamiyama

Takako Yamazaki

Takashi Masuda

Takehisa Ishimaru

Daiju Suzuki

Masataka Fujimoto

Kohsuke Aikawa

Hiroshi Minesaki

Tetsuro Nishii

Ayumi Yamaguchi

Akira Shiibashi

Katsuhide Suto

Masato Kimura

Naoki Sawai

Masato Ito

A fluid-heating device for heating fluid includes a heater unit configured to have a heater and a heating portion, the heating portion being formed as to cover surrounding of the heater, wherein the heating portion has an inner heat exchange surface formed on an inner surface of a through hole penetrating through an inner side of the heater and an outer heat exchange surface formed on an outer-wall portion of an outer side of the heater, the inner heat exchange surface being configured to perform heat exchange with the fluid, and the outer heat exchange surface being configured to perform the heat exchange with the fluid.

Fluid-heating device

It is possible to produce an optically active fluoroalkyl chloromethyl alcohol with a high optical purity and a good yield by treating a fluoroalkyl chloromethyl ketone with a microorganism having an activity for asymmetrically reducing the ketone or an enzyme having the activity. Then, it is possible to obtain a fluoroalkyl ethylene oxide by treating the alcohol with a base. Industrial implementation of the production method of the present invention is easy.

Method for industrial production of optically active fluoroalkyl ethylene oxide

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

According to the present invention, there is provided a production process of a 2-fluoroacrylic ester including: a bromination step of converting a 2-fluoropropionic ester to a 2-bromo-2-fluoropropionic ester by reaction of the 2-fluoropropionic ester with a nitrogen-bromine bond-containing brominating agent in the presence of a radical initiator; and a dehydrobromination step of reacting the 2-bromo-2-fluoropropionic ester with a base. It is not necessary in this process to adopt very-low-temperature conditions and to use a stoichiometric amount of expensive reagent. The target 2-fluoroacrylic ester can be thus produced at low cost.

Process for preparation of 2-fluoroacrylic esters

Esters and lactones can be respectively reduced to alcohols and diols in the presence of the Group 8 (VIII) transition metal complex, base and hydrogen gas (H). An extremely practical reduction method can be provided by preferable combinations of the Group 8 (VIII) transition metal complex, the base, a used amount of the base, a pressure of hydrogen gas and a reaction temperature. This method is used in place of hydride reduction and is a useful method by which design of highly active catalysts can be relatively easily made while a high productivity can be expected.

Practical method for reducing esters or lactones

An optically active, fluorine-containing carbonyl-ene product is produced by reacting a fluorine-containing &#x3b1;-ketoester with an alkene in the presence of a transition metal complex having an optically active ligand. There are Mode 1 of conducting this reaction in the absence of reaction solvent, Mode 2 of conducting this reaction in a solvent that is low in relative dielectric constant, and Mode 3 of conducting this reaction in a halogenated hydrocarbon-series solvent. In each of these three modes, it is possible to produce the optically active, fluorine-containing carbonyl-ene product with low cost.

Method for producing optically active fluorine-containing carbonyl-ene product

There is provided a novel, useful dehydroxyfluorination agent containing sulfuryl fluoride (SOF) and an organic base that is free from a free hydroxyl group in the molecule. According to the present dehydroxyfluorination agent, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in large-scale use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, for example, 4-fluoroproline derivatives, 2'-deoxy-2&#x2032;-fluorouridine derivatives, optically-active &#x3b1;-fluorocarboxylate derivatives, and monofluoromethyl derivatives, even in large scale.

Dehydroxyfluorination agent

It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SOF) in the presence of an organic base or in the presence of an organic base and 'a salt or complex comprising an organic base and hydrogen fluoride'. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2'-deoxy-2&#x2032;-fluorouridine derivatives, optically-active &#x3b1;-fluorocarboxylate derivatives, and the like, even in a large scale.

Process for production of fluoro derivative

The present invention relates to a process for producing an optically active &#x3b1;-fluorocarboxylate derivative represented by the formula [2], by reacting an optically active &#x3b1;-hydroxycarboxylate derivative with trifluoromethanesulfonyl fluoride (CFSOF) in the presence of an organic base, in the formula [2], R represents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 12; one of or two by any combination of aromatic hydrocarbon groups, unsaturated hydrocarbon groups, straight-chain or branched alkoxy groups of a carbon number of 1 to 6, aryloxy groups, halogen atoms (fluorine, chlorine, bromine and iodine), protected carboxyl groups, protected amino groups or protected hydroxyl group can be substituted on any carbon atoms of the alkyl group; Rrepresents a straight-chain or branched-chain alkyl group of a carbon number of 1 to 8; any carbon atoms of the alkyl groups of R and Rmay form a covalent bond; and * represents an asymmetric carbon.

Process for production of optically active &#x3b1;-fluoro-carboxylic ester derivatives

The present invention relates to a method of producing an optically active 1-aryl-2-fluoro-substituted ethylamine compound of the formula [2] or a salt thereof by hydrogenolysis of an optically active secondary amine compound of the formula [1] or a salt thereof in the presence of a transition metal catalyst of Group VIII [Chem. 59] [where Ar represents an aryl group; n represents an integer of 1 or 2; and * represents an asymmetric carbon][Chem. 60] [where Ar represents an aryl group; n represents an integer of 1 or 2; and * represents an asymmetric carbon].

Optically active 1-aryl-2-fluoro-substituted ethylamine and method for producing same

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Kawagoe, Japan

Takashi Ootsuka