Patents by Inventor Yutaka Katsuhara
Yutaka Katsuhara has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 8865946Abstract: There is provided according to the present invention a process for producing fluoromethyl hexafluoroisopropyl ether ((CF3)2CH—O—CH2F), including: reacting bisfluoromethyl ether with hexafluoroisopropyl alcohol in a solvent substantially immiscible with hydrogen fluoride in the presence of a catalytic amount of a strong acid selected from sulfuric acid and any other acids stronger in acidity than sulfuric acid. The process of the present invention enables industrial production of the fluoromethyl hexafluoroisopropyl ether without using hydrogen fluoride or a large amount of sulfuric acid and thereby without causing a large amount of waste as a by-product.Type: GrantFiled: April 9, 2010Date of Patent: October 21, 2014Assignee: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Hiroshi Takahashi, Michio Ishida
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Patent number: 8524941Abstract: According to the present invention, an ?-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an ?-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 ?-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the ?-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 ?-substituted acrylic acid.Type: GrantFiled: April 26, 2010Date of Patent: September 3, 2013Assignee: Central Glass Company, LimitedInventors: Shinya Akiba, Ryo Nadano, Yutaka Katsuhara
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Publication number: 20120136177Abstract: Disclosed is a method for producing hexafluoroacetone monohydrate by (1) allowing, in an organic solvent, hexafluoroacetone to be absorbed into water or a hexafluoroacetone hydrate (water addition method) or by (2) an easy method in which a hexafluoroacetone hydrate is mixed with an organic solvent and then distillation is conducted, thereby removing a mixture of water and the organic solvent as a low-boiling-point composition and obtaining a mixture of hexafluoroacetone monohydrate and the organic solvent as a high-boiling-point composition (dehydration method).Type: ApplicationFiled: July 30, 2010Publication date: May 31, 2012Applicant: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Tatsuya Hayasaka, Mineo Watanabe, Takashi Kume
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Publication number: 20120041237Abstract: There is provided according to the present invention a process for producing fluoromethyl hexafluoroisopropyl ether ((CF3)2CH—O—CH2F), including: reacting bisfluoromethyl ether with hexafluoroisopropyl alcohol in a solvent substantially immiscible with hydrogen fluoride in the presence of a catalytic amount of a strong acid selected from sulfuric acid and any other acids stronger in acidity than sulfuric acid. The process of the present invention enables industrial production of the fluoromethyl hexafluoroisopropyl ether without using hydrogen fluoride or a large amount of sulfuric acid and thereby without causing a large amount of waste as a by-product.Type: ApplicationFiled: April 9, 2010Publication date: February 16, 2012Applicant: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Hiroshi Takahashi, Michio Ishida
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Publication number: 20120004444Abstract: According to the present invention, an ?-substituted acrylic ester monomer for a fluorinated resist is produced by direct addition of an ?-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 ?-substituted acrylic ester monomer for the fluorinated resist by carrying out the target addition reaction of the fluorinated alkene and the ?-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 ?-substituted acrylic acid.Type: ApplicationFiled: April 26, 2010Publication date: January 5, 2012Applicant: Central Glass Company, LimitedInventors: Shinya Akiba, Ryo Nadano, Yutaka Katsuhara
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Patent number: 7919657Abstract: To provide a process for producing anhydrous hexafluoroacetone from hexafluoroacetone hydrate. To provide a process taking environment into consideration, that does not require a treatment of wastes, such as waste sulfuric acid, containing organic substances, which is inevitable in processes conducted hitherto using concentrated sulfuric acid, fuming sulfuric acid, and the like. A process for dehydrating a hexafluoroacetone hydrate, comprising introducing a hexafluoroacetone hydrate and hydrogen fluoride either as a mixture or separately into a distillation column, obtaining a composition containing hexafluoroacetone or a hexafluoroacetone-hydrogen fluoride adduct and hydrogen fluoride as a low boiling component, and obtaining a composition containing water and hydrogen fluoride as a high boiling component.Type: GrantFiled: August 28, 2008Date of Patent: April 5, 2011Assignee: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Tatsuya Hayasaka, Yoshiaki Miyamoto
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Publication number: 20100217049Abstract: [Task] To provide a process for producing anhydrous hexafluoroacetone from hexafluoroacetone hydrate. To provide a process taking environment into consideration, that does not require a treatment of wastes, such as waste sulfuric acid, containing organic substances, which is inevitable in processes conducted hitherto using concentrated sulfuric acid, fuming sulfuric acid, and the like. [Solving Means] A process for dehydrating a hexafluoroacetone hydrate, comprising introducing a hexafluoroacetone hydrate and hydrogen fluoride either as a mixture or separately into a distillation column, obtaining a composition containing hexafluoroacetone or a hexafluoroacetone-hydrogen fluoride adduct and hydrogen fluoride as a low boiling component, and obtaining a composition containing water and hydrogen fluoride as a high boiling component.Type: ApplicationFiled: August 28, 2008Publication date: August 26, 2010Applicant: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Tatsuya Hayasaka, Yoshiaki Miyamoto
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Patent number: 6331649Abstract: The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1). This process includes the step of reducing an oxime represented by the general formula (2), where R1 represents hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, or trifluoromethyl group, where R1 is defined as above, and R2 represents hydrogen atom, an alkyl group or an aralkyl group. With this process, the trifluoromethylbenzylamine can be produced with high selectivity.Type: GrantFiled: March 21, 2000Date of Patent: December 18, 2001Assignee: Central Glass Company, LimitedInventors: Satoru Narizuka, Yutaka Katsuhara
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Patent number: 6093858Abstract: The invention relates to a method for producing a bis(trifluoromethyl)benzene. This method includes the steps of (a) chlorinating a compound represented by the general formula (1) by chlorine, thereby to produce a trichloromethyltrifluoromethylbenzene; and (b) fluorinating the tricbloromethyltrifluoromethylbenzene by hydrogen fluoride, thereby to produce the bis(trifluoromethyl)benzene, ##STR1## where m is 1, 2 or 3. It is not necessary in the invention to handle solid in any reaction step.Type: GrantFiled: April 27, 1999Date of Patent: July 25, 2000Assignee: Central Glass Company, LimitedInventors: Michio Ishida, Makoto Koide, Yutaka Katsuhara
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Patent number: 5233098Abstract: A method for removing a perfluoroalkyl alcohol from a waste gas and recovering the perfluoroalkyl alcohol comprising the steps of bringing the waste gas into contact with an aqueous alkaline solution thereby to absorb the perfluoroalkyl alcohol into said solution and consequently obtain an aqueous alkaline solution containing an alkoxide of the perfluoroalkyl alcohol. Adding an acid to the aqueous alkaline solution containing the alkoxide of the perfluoroalkyl alcohol until the alkaline solution turns into an acidic solution with a pH value smaller than 5, thereby to turn said alkoxide into said perfluoroalkyl alcohol and subjecting the acidic solution to distillation to recover the perfluoroalkyl alcohol.Type: GrantFiled: June 12, 1992Date of Patent: August 3, 1993Assignee: Central Glass Company, LimitedInventors: Toru Nakazora, Toshihiro Nakamichi, Tuneyoshi Hisayuki, Katumi Takesita, Yutaka Katsuhara
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Patent number: 4691066Abstract: In the preparation of m-chlorobenzotrifluoride (m-CBTF) by reaction between benzotrifluoride and chlorine gas, a combination of a chloride of a metal having a valence of 3 to 6 and a small amount of iodine is used as catalyst. Alternative to iodine use can be made of an iodide that liberates iodine in the presence of chlorine. The catalyst exhibits high selectivity for m-CBTF and is effective for increasing the ratio of m-CBTF to p-CBTF in the reaction product.Type: GrantFiled: March 11, 1985Date of Patent: September 1, 1987Assignee: Central Glass Company, LimitedInventors: Fumio Inoue, Yutaka Katsuhara, Koshi Okazaki
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Patent number: 4599455Abstract: A fluorinated carbonyl compound ##STR1## where x is 2 or 3 and A represents CF.sub.3 or H, coexisting with hydrogen fluoride in a mixed gas is purified by first adjusting the temperature of the mixed gas to 100.degree.-300.degree. C. to cause decomposition of a usually coexisting complex of the fluorinated compound with HF and then bringing the hot mixed gas into contact with concentrated sulfuric acid maintained at 10.degree.-40.degree. C. Almost the entire amount of HF is absorbed in sulfuric acid and subsequently recovered, while the purified compound neither dissolves in sulfuric acid nor reacts with HF present in sulfuric acid.Type: GrantFiled: April 27, 1984Date of Patent: July 8, 1986Inventors: Yutaka Maruyama, Junji Negishi, Katuyoshi Murata, Yutaka Katsuhara
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Patent number: 4564716Abstract: 1,1,1,3,3,3-hexafluoropropane-2-ol is prepared easily and efficiently by gas-liquid reaction between hydrogen gas and a hexafluoroacetone hydrate such as trihydrate, which is liquid at room temperature, using a suitable catalyst such as active carbon-palladium catalyst. Preferably the gauge pressure of hydrogen gas is 2-10 kg/cm.sup.2, and the hydrogenolysis reaction temperature is 70.degree.-100.degree. C. The life of the catalyst can be prolonged by the addition of a small quantity of sodium hydroxide. The addition of a small quantity of aluminum hydroxide is effective in suppressing the formation of fluorine ions in the reaction liquid.Type: GrantFiled: September 27, 1984Date of Patent: January 14, 1986Assignee: Central Glass Company, LimitedInventors: Yutaka Katsuhara, Toshihiro Nakamichi, Toshikazu Kawai, Toru Nakazora
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Patent number: 4554382Abstract: Dehydrating decomposition of compound (I), i.e. gem-diol, hemi-acetal or hemi-ketal, by contact with sulfuric acid gives a carbonyl compound (II). ##STR1## Disclosed is a two-stage process in which the first stage is the contact of compound (I) with sulfuric acid at 90.degree.-140.degree. C. so as to partly decompose and dehydrate the compound (I), permitting the concentration of sulfuric acid to become lower than 93 wt. % but not lower than 65 wt. %, and the second stage is the contact of the product of the first-stage reaction with concentrated sulfuric acid at a temperature not higher than 60.degree. C., preventing the concentration of sulfuric acid from becoming lower than 93 wt %. For example, hexafluoroacetone is obtained from a hydrate thereof by this process using only a small amount of sulfuric acid.Type: GrantFiled: March 29, 1984Date of Patent: November 19, 1985Assignee: Central Glass Company LimitedInventors: Yoshihiro Tasaka, Toshihiro Nakamichi, Yutaka Katsuhara
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Patent number: 4544772Abstract: Crude hexafluoroacetone (HFA) hydrate containing chlorofluoroacetone(s) hydrate(s) as impurity is purified by adding an alkali metal hydroxide and maintaining at an elevated temperature, preferably at 100.degree.-110.degree. C., to thereby cause decomposition reaction of every chlorofluoroacetone hydrate with the alkali metal hydroxide, followed by neutralization of an excess portion of the alkali metal hydroxide. Alkali metal hydroxides, which readily react with anhydrous HFA, react preferentially with chlorofluoroacetone hydrates but hardly react with coexisting HFA hydrate.Type: GrantFiled: April 27, 1984Date of Patent: October 1, 1985Assignee: Central Glass Company, LimitedInventors: Mithio Sawai, Yoshihiro Tasaka, Toshikazu Kawai, Yutaka Katsuhara
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Patent number: 4450298Abstract: Vapor phase contact reaction between water and benzal chloride or a substitute expressed by C.sub.6 H.sub.(5-n) X.sub.n CHCl.sub.2, wherein X representing a halogen atom or a trifluoromethyl group and n being 1 or 2, to form benzaldehyde or a substitute expressed by C.sub.6 H.sub.(5-n) X.sub.n CHO can efficiently be achieved by using activated carbon treated with an acid such as sulfuric acid or impregnated with a metal chloride such as ferric chloride and/or a metal sulfate such as cupric sulfate as catalyst. The activated carbon catalyst long retains its high activity even when the starting material has trifluoromethyl group, which is liable to undergo partial decomposition with formation of hydrogen fluoride.Type: GrantFiled: July 20, 1982Date of Patent: May 22, 1984Assignee: Central Glass Company, LimitedInventors: Takeshi Kondow, Koshi Okazaki, Yutaka Katsuhara, Kimiaki Matsuoka