Central Glass Company, Limited

The State University of New York

Shinya Akiba

Takeo Komata

Ryo Nadano

Kenji Hosoi

Masaki Fujiwara

Satoru Miyazawa

Yusuke Kuramoto

Masaaki Takeda

Eri Nishizawa

Makoto Kobayashi

Kazuhiko Maeda

Haruhiko Komoriya

Kei Matsunaga

Yutaka Katsuhara

Yuzuru Morino

Toshihiro Nakamichi

Asuka Sano

Takaaki Yoshimura

Yoshiki Hirotsu

Takahisa Tada

Seiji Murata

Toshihiko Oono

Mitsutaka Otani

Shigeru Fujii

Robert L Brainard

Asami Inazu

Katsumi Iwao

Tishihiro Nakamichi

The present invention is directed to a purification method for purifying a fluorine-containing polymerizable monomer of the formula (1), in which the fluorine-containing polymerizable monomer is purified by distillation in the coexistence of a phenolic compound A such as 6-tert-butyl-2,4-xylenol and a phenolic compound B such as 2,2'-methylene-bis(4-methyl-6-tert-butylphenol). By the combined use of the phenolic compound A and the phenolic compound B, it is possible to significantly suppress polymerization or oligomerization of the fluorine-containing polymerizable monomer even during industrial-production-scale distillation and efficiently purify the fluorine-containing polymerizable monomer by distillation.

Method for purifying polymerizable fluoromonomer by distillation

A purification method of desflurane (difluoromethyl-1,2,2,2-tetrafluoroethyl ether of the formula (1)) includes bringing a mixture containing desflurane and a trihalomethane into contact with a base in the presence of a phase transfer catalyst, thereby decomposing the trihalomethane. By this method, only the trihalometane contained as a by-product in the desflurane is decomposed without causing decomposition of the desflurane, whereby the desflurane is obtained with high purity. 

Purification method and production method of difluoromethyl-1, 2, 2, 2-tetrafluoroethyl ether

Disclosed is an industrial method for efficient production of an &#x3b1;,&#x3b1;-difluoroaldehyde compound, which includes reaction of an &#x3b1;,&#x3b1;-difluoroacetate with hydrogen gas (H) in the presence of a ruthenium catalyst and a base. By the adoption of specific reaction conditions (catalyst, base, pressure etc.), it is possible to produce the target &#x3b1;,&#x3b1;-difluoroaldehyde compound with a high conversion rate and high selectivity.

Method for producing &#x3b1;,&#x3b1;-difluoroacetaldehyde

An object of the present invention is to remove a compound A from 'sevoflurane containing fluoromethyl-1,1,3,3,3-pentafluoroisopropenyl ether (compound A)' so as to collect high-purity sevoflurane. The present invention concerns a method for producing sevoflurane containing substantially no compound A, comprising the following steps of: bringing a composition containing hydrogen fluoride (HF) and water at a mass ratio of 1:1 to 1:30 into contact with a 1st organic liquid containing sevoflurane and a compound A, thereby obtaining a 2nd organic liquid containing the compound A in an amount that is lower than that in the 1st organic liquid (step 1a); and distilling the 2nd organic liquid under the presence of a degradation inhibitor, thereby obtaining sevoflurane containing substantially no compound A as a main distillation fraction (step 2).

Method for producing sevoflurane

A method for improving preservation stability of 2,2-difluoroacetaldehyde according to the present invention include at least: a first step of forming a '2,2-difluoroacetaldehyde-alcohol composite system' in which a 2,2-difluoroacetaldehyde hemiacetal coexists with an excess alcohol, wherein the total molar amount of the alcohol is 1.15 to 4.00 times the total molar amount of 2,2-difluoroacetaldehyde; and a second step of storing, in a storage container, the '2,2-difluoroacetaldehyde-alcohol composite system' formed in the first step. It is possible by this method to suppress the conversion of the 2,2-difluoroacetaldehyde hemiacetal to a dimer and maintain the original aldehyde activity of the target compound with less composition change over a long term.

Method for improving preservation stability of 2,2-difluoroacetaldehyde

Disclosed is a method for producing a hexafluoroisopropanol, including the steps of (a) purifying a mixture containing hexafluoroacetone and at least 1,1,1-trifluoro-2,2-dichloroethane as an impurity, thereby obtaining a purified hexafluoroacetone containing 120 ppm or lower of the 1,1,1-trifluoro-2,2-dichloroethane; and (b) bringing hydrogen (H) into contact with the purified hexafluoroacetone in the presence of a catalyst, thereby hydrogenating the hexafluoroacetone into the hexafluoroisopropanol. It is possible by this method to produce the hexafluoroisopropanol with a short reaction time and a high conversion. Therefore, it is possible to particularly advantageously produce fluoromethyl hexafluoroisopropyl ether (sevoflurane) by using the hexafluoroisopropanol produced by the method.

Method for producing hexafluoroisopropanol and fluoromethyl hexafluoroisopropyl ether (sevoflurane)

A method of stabilizing a fluorine-containing acid amplifier. The method is provided to include the step of dissolving a fluorine-containing acid amplifier in an organic solvent thereby producing a solution of the fluorine-containing acid amplifier, the fluorine-containing acid amplifier being represented by general formula (1): 

Method of stabilizing fluorine-containing acid amplifier

According to the present invention, an &#x3b1;-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an &#x3b1;-substituted acrylic acid to a fluorinated alkene in the presence of a specific acid catalyst having a sulfonyl group. By the use of such a specific acid catalyst, it is possible to achieve industrial-scale production of the &#x3b1;-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the &#x3b1;-substituted acrylic acid efficiently during the occurrence of side reactions such as isomerization of the alkene, generation of a diol and excessive addition of the &#x3b1;-substituted acrylic acid.

Process for producing monomer for fluorinated resist

A method for forming a protective film of a fluorine-containing polymer composition excellent in smoothness and adhesiveness on a photoresist. Moreover, there is provided a means for removing the protective film without impairing the underlying photoresist. A polymer coating composition obtainable by dissolving a fluorine-containing polymer compound in a solvent comprising a fluorinated acetal having a specific structure is applied on a photoresist and dried to form a protective film. A fluorinated acetal having the specific structure is suitable as a solvent for being brought into contact with a fluorine-containing polymer film, peeling the film, and forming a photoresist or a lithographic pattern.

Fluorine-containing polymer coating composition, method for forming fluorine-containing polymer film using coating composition, and method for forming photoresist or lithographic pattern

A benzyl vinyl ether represented by the following formula is hydrolyzed in the presence of a catalyst selected among Arrhenius acids and Lewis acids to obtain 3,3,3-trifluoropropionaldehyde. Subsequently, the 3,3,3-trifluoropropionaldehyde is oxidized with an oxidizing agent. Thus, 3,3,3-trifluoropropionic acid can be more advantageously produced than in conventional techniques from an inexpensive starting material.

Process for producing 3,3,3-trifluoropropionic acid

There is provided a process for producing 3,3,3-trifluoropropionyl chloride, which is characterized in that 3,3,3-trifluoropropionaldehyde is chlorinated by a chlorinating agent selected from the group consisting of chlorine (Cl), sulfuryl chloride (SOCl) and organic N-chloro compounds.

Method for producing 3,3,3-trifluoropropionyl chloride

There is provided a process for producing 3,3,3-trifluoropropionaldehyde, including the step of hydrolyzing a benzyl vinyl ether of the formula [1] in the presence of a catalyst selected from the group consisting of Arrhenius acids and Lewis acids, [Chem. 17] where R represents phenyl or phenyl having a substituent Rselected from the group consisting of alkyl groups, alkoxy groups, halogen atoms, nitro groups and amino groups.

Process for producing 3,3,3-trifluoropropionaldehyde

A process for producing an &#x3b1;-substituted acrylic norbornanyl compound represented by the formula [3] includes reacting an &#x3b1;-substituted acrylic acid anhydride represented by the formula [1] with a substituted norbornanyl alcohol represented by the formula [2]. wherein Rrepresents a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, or perfluoroethyl group, and wherein one of R, Rand Ris a CFC(CF)(OH)CH&#x2014; group, and each of the other two of R, Rand Ris a hydrogen.

Process for producing &#x3b1;-substituted acrylic norbornanyyl compounds

A process for producing a fluorine-containing 2,4-diol represented by the formula [4], wherein Rrepresents a hydrogen atom or an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; Rrepresents an acyclic or cyclic alkyl group having a carbon atom number of 1 to 7; and Rand Rare optionally bonded to each other to form a ring, includes reducing a hydroxy ketone represented by the formula [3], wherein Rand Rare defined as above, by hydrogen in the presence of a ruthenium catalyst.

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Kawagoe, Japan

Shinya Akiba