Patents by Inventor Isoo Shimizu
Isoo Shimizu 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: 7060779Abstract: A process for efficiently producing hydrocarbon/phenol resin having a satisfactory hue through reaction of phenol with an unsaturated cyclic hydrocarbon having two or more carbon—carbon double bonds in the presence of an acid catalyst, which comprises (1) a step in which the molar fraction of ether type reaction products to all the reaction products is regulated to at least 0.1 and (2) a step in which the ether type reaction products yielded by the progress of the reaction is substantially eliminated. The hydrocarbon/phenol resin thus obtained is reacted with an epihalohydrin in the presence of a base catalyst to obtain an epoxy resin having an excellent hue.Type: GrantFiled: April 28, 2000Date of Patent: June 13, 2006Assignee: Nippon Petrochemicals Company, LimitedInventors: Satoshi Mori, Isoo Shimizu
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Patent number: 6180079Abstract: In wet oxidizing process of an aqueous alkali waste which contains absorbed hydrogen sulfide and carbon dioxide, a convenient method for improving the safety in oxidizing operation and the efficiency in oxidation reaction.Type: GrantFiled: January 28, 1997Date of Patent: January 30, 2001Assignee: Nippon Petrochemicals Company, LimitedInventor: Isoo Shimizu
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Patent number: 5846429Abstract: A method for effectively separating and removing or recovering BF.sub.3 existing in a liquid hydrocarbon which is characterized in that an organic liquid mixture containing suspended or dissolved BF.sub.3 is brought into liquid phase contact with a synthetic polymer fiber containing nitrile groups at a temperature of 50.degree. C. or lower, so that the BF.sub.3 is adsorbed by the synthetic polymer fiber and it is then heated to 80.degree. C. or higher to recover the BF.sub.3.Type: GrantFiled: February 13, 1997Date of Patent: December 8, 1998Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yoshisuke Kakuyama, Tsutomu Takashima
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Patent number: 5777191Abstract: A wet oxidizing process for waste soda to attain stable cooling and complete gas-liquid separation of waste soda which is discharged from a wet oxidation reactor for alkali waste liquid, and which process comprises the steps of (1) and (2) and optionally any one of steps (3) to (5), wherein (1) a wet oxidation step in which the alkali waste liquid is brought into contact with excess molecular oxygen, said alkali waste liquid being obtained by bringing an aqueous alkali into contact with a hydrocarbon fluid containing acidic substances of hydrogen sulfide and carbon dioxide, (2) a reducing step to reduce the pressure of a mixture of the oxidized alkali waste liquid from said wet oxidation step and a surplus gas, (3) a separation step to separate said mixture into a gas phase and a liquid phase in a gas-liquid separation tank, (4) a cooling step to cool the separated liquid phase and (5) another cooling step to cool the separated gas phase.Type: GrantFiled: January 28, 1997Date of Patent: July 7, 1998Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Jun-ichi Kohhashi
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Patent number: 5457228Abstract: A method for producing a lower alkyl acetate in which undesirable polymerization of the starting material of olefin and deterioration of catalyst can be avoided, a higher catalytic efficiency and a higher reaction rate are attained, the installation of reaction equipment is inexpensive and the operation of the reaction can be carried out without difficulty. The method of the invention comprises the steps of feeding acetic acid and an olefin both in a liquid state and in cocurrent through a continuous flow type fixed bed reactor containing an acidic ion exchange resin catalyst(s) under the conditions that the molar ratio of acetic acid to the olefin in a feed current is in the range of 1.0 to 2.0 and an LHSV of acetic acid relative to the catalyst layer is 0.1 to 10.0 with maintaining the inlet of the catalyst bed at 70.degree. C. to 120.degree. C.; cooling the obtained reaction mixture to a temperature not lower than 70.degree. C.; and recycling it to the catalyst bed.Type: GrantFiled: October 27, 1994Date of Patent: October 10, 1995Assignees: Daicel Chemical Industries, Ltd., Nippon Petrochemicals Company, LimitedInventors: Yuichi Tokumoto, Kazuo Sakamoto, Kikuo Sasaki, Isoo Shimizu
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Patent number: 5436402Abstract: A method for preparing a high-purity p-isobutylstyrene is here disclosed which comprises the first step of reacting o- and/or m-isobutylethylbenzene, if necessary, together with isobutylbenzene, in the presence of an acid catalyst in a liquid phase at a reaction temperature of -10.degree. to 600.degree. C. so that the production of sec-butylethylbenzene in butylethylbenzene may not exceed 20% by weight, in order to form a mixture of p-isobutylethylbenzene and sec-butylethylbenzene; and the second step of bringing the mixture of p-isobutylethylbenzene and sec-butylethylbenzene recovered from the first step into contact with a dehydrogenation metal catalyst containing at least one metal selected from the groups Ib, IIb, VIa, VIIa and VIII of the periodic table at a reaction temperature of 300.degree. to 650.degree. C. under a reaction pressure of 50 kg/cm.sup.2 or less in a gaseous phase.Type: GrantFiled: October 17, 1994Date of Patent: July 25, 1995Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuichi Tokumoto, Kazumichi Uchida
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Patent number: 5260477Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step (I) of dehydrogenating p-isobutylethylbenzene in a gaseous phase in the presence of a dehydrogenating metal catalyst to form p-isobutylstyrene and at least one unsaturated hydrocarbon compound selected from a group A defined in Claim 1; a step (II) of reacting p-isobutylstyrene obtained in the step (I) with carbon monoxide and hydrogen or with carbon monoxide and water or a lower alcohol in the presence of a transition metal complex carbonylating catalyst to form .alpha.-(4-isobutylphenyl)propionic acid or its precursor; and a step (III) of hydrogenating at least one unsaturated hydrocarbon compound selected from the group A obtained in the dehydrogenation step (I) to form p-isobutylethylbenzene, and recycling the thus formed p-isobutylethylbenzene through the step (I) as the raw material of the step (I).Type: GrantFiled: December 18, 1989Date of Patent: November 9, 1993Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuichi Tokumoto, Kazumichi Uchida
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Patent number: 5221766Abstract: A method for producing .alpha.-(p-isobutylphenyl)-propionic acid with a high selectivity and high purity. The method is characterized in that .alpha.-(p-isobutylphenyl)propionaldehyde is oxidized at temperatures not higher than -12.degree. C. in the presence of an acid using a hypohalogenite. The acid is an inorganic acid such as sulfuric acid, phosphoric acid and hydrochloric acid and the hypohalogenite may be sodium salts, potassium salts or calcium salts of hypochlorous acid or hypobromous acid.Type: GrantFiled: April 7, 1992Date of Patent: June 22, 1993Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura
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Patent number: 5166419Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises the following steps (I), (II) and (III):step (I): subjecting isobutylbenzene and a polyalkylbenzene to disproportionation reaction in order to form p-isobutylethylbenzenestep (II): dehydrogenating p-isobutylethylbenzene obtained in the step (I) to form p-isobutylstyrene, andstep (III): the following step (IIIa) or (IIIb):step (IIIa): reacting p-isobutylstyrene obtained in the step (II) with carbon monoxide and hydrogen to prepare .alpha.-(4-isobutylphenyl)propionaldehyde, orstep (IIIb): reacting p-isobutylstyrene obtained in the preceding step (II) with carbon monoxide and water or a lower alcohol to prepare .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester.Type: GrantFiled: August 22, 1990Date of Patent: November 24, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Yuuichi Tokumoto, Isoo Shimizu, Satoru Inoue
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Patent number: 5097061Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.Type: GrantFiled: June 19, 1989Date of Patent: March 17, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
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Patent number: 5081279Abstract: This invention provides a method of producing highly pure .alpha.-(3-benzoylphenyl)propionic acid derivatives, which are medicines per sec or which can easily afford the same, from readily available 3-ethylbenzophenone in a very simplified manner efficiently and economically. The method comprises dehydrogenating 3-ethylbenzophenone in vapor phase in the presence of an inert gas and carbonylating the formed 3-ethenylbenzophenone in the presence of a carbonylation catalyst comprising a transition metal complex.Type: GrantFiled: November 6, 1990Date of Patent: January 14, 1992Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
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Patent number: 5026939Abstract: A method for producing alkylstyrene which is characterized in that 1,2-di(substituted phenyl)ethane is brought into contact with an acid catalyst at 200.degree. C. to 650.degree. C. in the presence of an inert gas to crack it into alkylstyrene and alkylbenzene. The method of the invention has advantages in that the operation of reaction and separation of reaction mixture are quite easy, the lowering of catalytic activity is small, and unreacted starting material can be reused.Type: GrantFiled: May 5, 1988Date of Patent: June 25, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
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Patent number: 4999450Abstract: A process for preparing .alpha.-(3-benzylphenyl)-propionic acid or its derivative, a precursor of ketoprofen (trade name), which comprises dehydrogenating a by-product oil fraction formed in the production of ethylbenzene using synthetic zeolite as an alkylating catalyst, and carbonylating the product with carbon monoxide or the like. This precursor can be easily converted into ketoprofen, a useful medicine as an anti-inflammatory agent.Type: GrantFiled: March 23, 1990Date of Patent: March 12, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4982007Abstract: A process for selectively hydroformylating a diolefin, which comprises reacting a (1-arylethyl)vinylbenzene with carbon monoxide and hydrogen under the conditions of 40.degree. to 200.degree. C. in reaction temperature and 5 kg/cm.sup.2 or above in reaction pressure in the presence of a transition metal carbonylation catalyst to thereby selectively hydroformylating only the vinyl group and produce .alpha.-((1-arylethenyl)phenyl)propionaldehyde. The starting material to be hydroformylated may be a mixture of the (1-arylethenyl)vinylbenzene with a 1,1-di(substituted aryl)ethylene not substituted by a vinyl group.Type: GrantFiled: March 2, 1990Date of Patent: January 1, 1991Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4967009Abstract: This invention relates to a method for manufacturing aromatic compounds having the following formula (II) comprising the step of reacting an unsaturated aromatic compound having the following formula (I) with an aryl compound containing an iodosyl group or the salt thereof within a temperature range of from -50.degree. to 200.degree. C.Type: GrantFiled: July 7, 1989Date of Patent: October 30, 1990Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Kouichi Iwamoto
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Patent number: 4937375Abstract: New compounds of .alpha.-(3-(1-phenylethenyl)phenyl)-propionic acid and its esters and a method for producing .alpha.-(3-benzoylphenyl)propionic acid which is prepared by oxidizing the former compound as an intermediate. The method is characterized in the easiness in operation, the low cost and the high purity of the product.Type: GrantFiled: March 9, 1988Date of Patent: June 26, 1990Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4922052Abstract: The invention relates to a new compound of (3-Vinylphenyl)phenylmethane and a method for producing .alpha.-(3-benzoylphenyl)propionic acid of ketoprofen without difficulty at low cost and in a high yield. The method comprises the steps of: reacting (3-vinylphenyl)phenylmethane with carbon monoxide and hydrogen, water or lower alcohol in the presence of a transition metal carbonylation catalyst to form .alpha.-(3-benzylphenyl)propionic acid derivative, and when the thus obtained compound is an aldehyde, oxidizing methylene group and formyl group of the compound simultaneously or sequentially, or when the obtained compound is an acid or its ester, oxidizing the methylene group of the compound, and if need be, it is followed by hydrolysis.Type: GrantFiled: March 18, 1988Date of Patent: May 1, 1990Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4914242Abstract: 3-Ethylbenzophenone is prepared by oxidizing a by-product heavy oil fraction produced in the production of ethylbenzene using ZSM-5 type synthetic zeolite catalyst, without splitting carbon-to-carbon bonds. 3-Ethylbenzophenone is a starting material for synthesis of medicines, etc.Type: GrantFiled: November 23, 1988Date of Patent: April 3, 1990Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4908473Abstract: A process for selectively hydroesterifying a diolefin, which comprises reacting a (1-arylethenyl)vinylbenzene with carbon monoxide and water or a lower alcohol at a reaction temperature of 40.degree. to 200.degree. C. and a carbon monoxide pressure 20 to 700 kg/cm.sup.2 in the presence of a noble metal complex catalyst to thereby selectively hydroesterifying only the vinyl group of it and produce .alpha.-((1-arylethenyl)phenyl)propionic acid or its alkyl ester. The starting material to be hydroesterified may be a mixture of 1,1-di(substituted aryl)ethylene not substituted by a vinyl group.Type: GrantFiled: November 14, 1988Date of Patent: March 13, 1990Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
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Patent number: 4889952Abstract: A novel compound of .alpha.-(3-(1-phenylethenyl)phenyl)-propionaldehyde and a method for producing .alpha.-(3-benzoylphenyl)propionic acid which is prepared by oxidizing the former compound as an intermediate. The method is characterized in the easiness in operation, the low cost and the high purity of the product.Type: GrantFiled: March 11, 1988Date of Patent: December 26, 1989Assignee: Nippon Petrochemical Company, Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai