Central Glass Company, Limited

Kitasato Daiichi Sankyo Vaccine Co., Ltd.

Mineo Watanabe

Toshikazu Kawai

Takaaki Yoshimura

Masatomi Kanai

Hideaki Imura

Takashi Kume

Ryo Nadano

Yutaka Katsuhara

Yoshihiko Goto

Takashi Sakaya

Manami Kumakura

Masamichi Maruta

Kenji Hosoi

Toshihiro Nakamichi

Manami Kobayashi

Kensuke Hirotaki

Naoya Ueshima

Eiji Komatsu

Shigeru Suenaga

Showzou Kaneda

Etsuko Katoh

Manami Kamakura

Fluoral is obtained by gas-phase fluorination of chloral in the presence of a catalyst and then reacted with trimethyl orthoformate, thereby readily forming 1,2,2,2-tetrafluoroethyl methyl ether as an intermediate for production of desflurane. 1,2,2,2-Tetrafluoroethyl difluoromethyl ether (desflurane) is produced with high yield from the thus-formed 1,2,2,2-tetrafluoroethyl methyl ether by chlorination and fluorination. This method enables efficient industrial-scale production of desflurane useful as an inhalation anesthetic.

Production method for 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane)

An objective of the present invention is to provide a whole-cell bacterial vaccine composition for preventing whooping cough caused by, comprising whole cells, whole-cell homogenate, or cell lysate ofas an immunogen, and methods for producing them.

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A process of producing chlorofluoroacetones represented by a general formula

Process of producing chlorofluoroacetones

The invention relates to a method for producing 3,3-dichloro-1,1,1-trifluoroacetone. This method includes a step of fluorinating pentachloroacetone by hydrogen fluoride in the presence of a fluorination catalyst. This fluorination may be conducted in a liquid phase in the presence of an antimony compound as the fluorination catalyst. Alternatively, the fluorination may be conducted in a gas phase in the presence of a fluorination catalyst which may be a fluorinated alumina or at least one compound of at least one metal selected from Al, Cr, Mn, Ni, and Co. The method is suited to an industrial scale production of 3,3-dichloro-1,1,1-trifluoroacetone. The invention further relates to another method for producing 3,3-dichloro-1,1,1-trifluoroacetone. This method includes a step of purifying a crude 3,3-dichloro-1,1,1-trifluoroacetone by a distillation in the presence of water, thereby to produce 3,3-dichloro-1,1,1-trifluoroacetone which is substantially free of organic matters other than 3,3-dichloro-1,1,1-trifluoroacetone. This crude 3,3-dichloro-1,1,1-trifluoroacetone may be the reaction products of the fluorination of pentachloroacetone in a gas phase. Due to the provision of the another method, 3,3-dichloro-1,1,1-trifluoroacetone can be produced with high yield.

Method for producing 3,3-dichloro-1,1,1-triflouroacetone

Method of producing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether

Method of purifying fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether

Method of purifying fluoromethyl-1,1,1,3,3,3, hexafluoroisopropyl ether

Gas chromatographic analysis of

2,2-Bis(4-aminophenyl)hexafluoropropane is prepared by the steps of (a) reacting 2,2-bis(4-carboxyphenyl)hexafluoropropane with thionyl chloride at 80.degree.-150.degree. C. in a water insoluble organic liquid in the presence of a catalyst such as dimethylformamide to obtain a solution of 2,2-bis(4-chloroformylphenyl)hexafluoropropane, (b) mixing the obtained solution with an aqueous solution of sodium azide to obtain an acid azide solution, (c) heating the organic phase of the acid azide solution to 80.degree. C. or above to cause rearrangement of the acid azide into an isocyanate, (d) hydrolyzing the isocyanate by mixing the isocyanate solution with an acid such as 40-80% sulfuric acid to form a salt of the aimed diamine as an aqueous solution mixed with an organic phase, and (e) neutralyzing the aqueous solution separated from the liquid mixture obtained at step (d) to precipitate the aimed diamine. This process is favorable for industrial practice because the main steps (a) to (d) are all reactions in organic liquids without precipitating solid intermediates.

Process of preparing 2,2-bis(4-aminophenyl)-hexafluoropropane

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Saitama, Japan

Mineo Watanabe