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).

  • Patent number: 4885419
    Abstract: Novel compounds of 1,2-di(isobutylphenyl)ethane and 1,2-di(isobutylphenyl)ethylene, method for producing the same and method for preparing 4-isobutylstyrene and .alpha.-(4-isobutylphenyl)propionic acid from any of these compounds. In the preparation of 4-isobutylstyrene from the former two compounds by cracking or disproportionation, the components in the resultant reaction mixture can be separated without difficulty, the formation of by-product isobutylbenzene can be avoided, and the remaining unreacted starting material can be reused for the same reaction without causing any adverse effect on a catalyst.
    Type: Grant
    Filed: May 5, 1988
    Date of Patent: December 5, 1989
    Assignee: Nippon Petrochemicals Company, Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4855519
    Abstract: A method for producing arylethylene comprising four steps of: (I) bringing 1,1-diarylethane into contact with an acid catalyst in the presence of an inert gas to crack said compound into arylethylenes and alkylbenzenes; (II) separating the reaction mixture obtained in the above cracking step (I) into at least a fraction mainly containing 1,1-diarylethane; (III) bringing said fraction mainly containing 1,1-diarylethane into contact with hydrogen gas in the presence of a hydrogenation catalyst; and (IV) re-cracking hydrogenated fraction obtained in the preceding hydrogenation step (III) by bringing it into said cracking step (I).Particularly, this method is useful for producing p-isobutylstyrene which is a starting material for preparing a valuable medicine of ibuprofen.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Petrochemicals Company
    Inventors: Isoo Shimizu, Hitoshi Mitsuyuki, Kazumichi Uchida, Yuuichi Tokumoto
  • Patent number: 4855518
    Abstract: A method for producing p-alkylstyrene which is characterized in that side reaction scarcely occurs, catalyst and unreacted material are easily recovered for the reuse, the p-position selectivity is excellent and yield of aimed product is high. In the method, monoalkylbenzene having an alkyl group with 3 or more carbon atoms is reacted with acetaldehyde in the presence of hydrogen fluoride catalyst under the conditions of a temperature of 0.degree. C. or lower, a molar ratio of 2 to 100 in "alkylbenzene/acetaldehyde", the other molar ratio of 1.7 to 300 in "hydrogen fluoride/acetaldehyde", the proportion of hydrogen fluoride to the sum of hydrogen fluoride and water in the reaction system of 65% by weight or higher, and the concentration of acetaldehyde in the reaction system of 1.0% by weight or lower to obtain 1,1-bis(p-alkylphenyl)ethane, and then subjecting it to catalytic cracking at a temperature in the range of 200.degree. to 650.degree. C. in the presence of an acid catalyst.
    Type: Grant
    Filed: July 19, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yuuichi Tokumoto
  • Patent number: 4835337
    Abstract: A method for producing efficiently a highly pure 1-(m-ethylphenyl)-1-phenylethane or m-ethylphenylphenylmethane which are used as the starting materials for preparing medicines and other organic compounds. The method comprises the step of reacting a diaryl compound with benzene or alkylbenzene in the presence of an acid catalyst selected from the group consisting of AlCl.sub.3, AlBr.sub.3, HF.BF.sub.3 complex and Y-type zeolites.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: May 30, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yasuo Matsumura, Kazumichi Uchida
  • Patent number: 4827065
    Abstract: A method for producing p-isobutylstyrene which is characterized in that starting materials are inexpensive, processes are easy to be done and products are highly pure. The method comprises the step of catalytically cracking 1,1-bis(p-isobutylphenyl)ethane at temperatures in the range of 200.degree. to 650.degree. C. in the presence of a protonic acid catalyst and/or a solid acid catalyst to produce p-isobutylstyrene and isobutylbenzene, and at least a portion of said isobutylbenzene is recycled to produce said 1,1-bis(p-isobutylphenyl)ethane by reaction with acetaldehyde in the presence of sulfuric acid.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: May 2, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
  • Patent number: 4822934
    Abstract: 1-(3-Vinylphenyl)-1-phenylhydrocarbons and method for producing the same. The invention further relates to 1-(3-vinylphenyl)-1-phenylethane which is used for preparing the former compound. The 1-(3-vinylphenyl)-1-phenylethylene is used as a new intermediate for preparing .alpha.-(3-benzoylphenyl)propionic acid (tradename: ketoprofen) through .alpha.-3-(1-phenylethenyl)phenyl)propionic acid or its alkyl ester. The ketroprofen is a useful medicine for the relief of pain and inflammation.
    Type: Grant
    Filed: March 9, 1988
    Date of Patent: April 18, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yutaka Arai
  • Patent number: 4814494
    Abstract: An effective method for producing highly pure (aryl substituted)carboxylic acid or its salt which comprises the steps of:(I) oxidizing (aryl substituted)aldehyde in an acidic phase in the presence of hypohalogenite; and(II) bringing the oxidized product obtained in the preceding step into contact in a liquid phase with hydrogen in the presence of a catalyst of transistion metal of the group VIII in the periodic table.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: March 21, 1989
    Assignee: Nippon Petrochemicals Company, Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4761508
    Abstract: The present invention is concerned with a novel intermediate 1,1-(3-ethylphenyl)phenylethylene represented by the formula (I) and its manufacturing method, and according to the present invention, Ketoprofen can be synthesized at a low cost and in a high yield.
    Type: Grant
    Filed: July 22, 1986
    Date of Patent: August 2, 1988
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Shigenobu Kawakami, Atsushi Sato
  • Patent number: 4734528
    Abstract: The present invention provides a method for preparing 3-ethylbenzophenone in a high purity which comprises the steps of alkylating benzene with ethylene in the presence of an alkylating catalyst to obtain an alkylated product composed mainly of unreacted benzene, ethylbenzene, polyethylbenzenes and heavier substances; subjecting the alkylated product to rectification in order to recover therefrom a fraction which has a temperature range of boiling points within the range of 275.degree. to 310.degree. C.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: March 29, 1988
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Atsushi Sato
  • Patent number: 4731483
    Abstract: The present invention provides a method for preparing 3-ethylbenzophenone in a high purity which comprises the steps of alkylating benzene with ethylene with the aid of an alkylating catalyst to obtain an alkylated product composed mainly of unreacted benzene, ethylbenzene, polyethylbenzenes and heavier by-products; subjecting the alkylated product to distillation in order to recover therefrom a fraction which has a temperature range of boiling points within the range of 275.degree. to 310.degree. C. (in terms of atmospheric pressure); dehydrogenating the recovered fraction at a reaction temperature within the range of 200.degree. to 700.degree. C.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: March 15, 1988
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Shigenobu Kawakami, Atsushi Sato
  • Patent number: 4709089
    Abstract: An effective method for refining 2-(aryl substituted)propionic acid or its salt which is characterized in that 2-(aryl substituted)propionic acid or its salt containing halogenated by-products is brought into contact with hydrogen in a liquid phase containing water under a basic condition at temperatures in the range of 20.degree. C. to 170.degree. C. in the presence of a catalyst of transition metal of the group VIII in the periodic table, thereby dehalogenating said halogenated by-product and producing highly pure 2-(aryl substituted)propionic acid or its salt.
    Type: Grant
    Filed: February 6, 1987
    Date of Patent: November 24, 1987
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4694100
    Abstract: A method for producing .alpha.-(p-isobutylphenyl)propionic acid or its alkyl esters which is characterized in that starting materials are inexpensive, processes are easy to be done and products are highly pure. The method comprises the steps of (I): catalytically cracking 1,1-bis(p-isobutylphenyl)ethane at temperatures in the range of 200.degree. to 650.degree. C. in the presence of a protonic acid catalyst and/or a solid acid catalyst to produce isobutylbenzene and p-isobutylstyrene; and (II): reacting said p-isobutylstyrene with carbon monoxide and water or alcohol at temperatures in the range of 40.degree. to 150.degree. C. in the presence of a metal complex carbonylation catalyst to produce .alpha.-(p-isobutylphenyl)propionic acid or its alkyl ester; or (III): reacting said p-isobutylstyrene with carbon monoxide and hydrogen at temperatures in the range of 40.degree. to 150.degree. C. in the presence of a metal complex carbonylation catalyst to produce .alpha.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: September 15, 1987
    Assignee: Nippon Petrochemicals Company, Ltd.
    Inventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
  • Patent number: 4659840
    Abstract: Provided is a method for preparing diaryl iodonium salts represented by the formula:[Ar.sub.1 --I.sup..sym. --Ar.sub.2 ]HSO.sub.4.sup..crclbar.wherein Ar.sub.1 and Ar.sub.2 respectively are an aryl group which may be substituted with an electron donor group and which may be the same or different which comprises subjecting a compound represented by the formula Ar.sub.1 --H wherein Ar.sub.1 is as defined above and a compound Ar.sub.2 --I wherein Ar.sub.2 is as defined above to a coupling reaction in a sulfuric acid solution containing an oxidizing agent and diluted with a diluting agent to a concentration of 85% by weight or less at a reaction temperature in the range from -20.degree. to +35.degree. C.
    Type: Grant
    Filed: March 8, 1984
    Date of Patent: April 21, 1987
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Yasuo Matsumura, Yoshihisa Inomata
  • Patent number: 4620056
    Abstract: A method for producing an aromatic hydrocarbon easily and safely without the use of carrier-supported catalyst and is characterized in that an unsaturated compound having a double bond or bonds that are conjugated with the benzene ring is allowed to coexist in the process to alkylate a substituted aromatic hydrocarbon with olefins in the presence of 5 mM or more of metallic sodium and potassium compound to provide 3 mM or more of potassium ions relative to 1 mole of the substituted aromatic hydrocarbon, said substituted aromatic hydrocarbon having at least one alkyl group or alkylene group which has at least one hydrogen atom in the .alpha.-position relative to the aromatic ring of said substituted aromatic hydrocarbon.
    Type: Grant
    Filed: August 28, 1985
    Date of Patent: October 28, 1986
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Isoo Shimizu, Hideki Nomura, Kazumichi Uchida, Hitoshi Mitsuyuki
  • Patent number: 4554360
    Abstract: Provided is a process for converting an aromatic compound to prepare an iodoarene, Ar--I, and an aryl compound which is a compound wherein an unsaturated compound is bonded directly to an aryl group, Ar, which process comprises reacting a diaryliodonium salt represented by general formula (I)[Ar--I.sup..sym. --Ar]X.sup..crclbar. (I)wherein Ar is an aryl group which may be substituted and two Ar's are identical and X.sup..crclbar. is a counter ion inert to the reaction with the unsaturated compound in a solvent in the presence of a transition metal catalyst and a base or a reducing metal, said reaction being carried out at a temperature not higher than 80.degree. C. and/or by using at least one of the base, the reducing metal and the unsaturated compound in an amount not more than 1.
    Type: Grant
    Filed: March 29, 1984
    Date of Patent: November 19, 1985
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Yamazaki, Takehiko Suzuki, Isoo Shimizu, Yasuo Matsumura
  • Patent number: 4390194
    Abstract: A recording material prepared by using a solvent mixture which has excellent dissolving property for dye-precursors and which gives high color developing rate and high developed color density. The recording material comprises a sheet material having thereon a layer of microcapsules containing an electron donating dye-precursor and a solvent mixture for said dye-precursor, and is characterized in that said solvent mixture consists essentially of 5 to 50 wt % of 1-methyl-3-phenylindane and 95 to 50 wt % of at least one kind of diarylalkanes.
    Type: Grant
    Filed: June 23, 1981
    Date of Patent: June 28, 1983
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Atsushi Sato, Isoo Shimizu, Naoya Takahashi
  • Patent number: 4329536
    Abstract: Provided is an oil-impregnated power cable comprising an insulation layer formed by winding a composite film of polyolefin film and insulating paper onto an electric conductor and impregnated with an impregnating oil, said impregnating oil comprising distillates within a boiling range in terms of values at normal pressure between 265.degree. C. and 360.degree. C. obtained by contacting a hydrocarbon mixture with a boiling range between 75.degree. C. and 198.degree. C. resulting from a thermal cracking of petroleum hydrocarbons at a temperature of 700.degree. C. or higher and containing monocyclic aromatics and aromatic olefins, in liquid phase with an acid catalyst.
    Type: Grant
    Filed: June 16, 1980
    Date of Patent: May 11, 1982
    Assignee: Nippon Petrochemical Company, Ltd.
    Inventors: Atushi Sato, Isoo Shimizu, Keizi Endo, Hitoshi Yanagishita
  • Patent number: 4289806
    Abstract: A pressure-sensitive recording material which is excellent in several properties and prepared at a low cost. The pressure-sensitive recording material of the invention is applied with pressure-rupturable microcapsules containing a solution of dyestuff in a solvent fraction having a boiling range of 265.degree. C. to 360.degree. C. (converted to atm. press.) which is obtained by treating a raw material fraction in the presence of an acid catalyst. The raw material fraction is obtained from the product of thermal cracking of petroleum hydrocarbons at a temperature of 700.degree. C. or above and mainly contains the distillate having boiling points in the range of 75.degree. C. to 198.degree. C. and the main components thereof are monocyclic aromatic hydrocarbons (excluding aromatic olefins) and monocyclic aromatic olefins.
    Type: Grant
    Filed: January 24, 1980
    Date of Patent: September 15, 1981
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Atsushi Sato, Isoo Shimizu, Eiichi Matsuzaka
  • Patent number: 4289918
    Abstract: Provided is a method of aralkylating alkylbenzenes by contacting styrene and alkylbenzene at an elevated temperature in the presence of a resinous perfluoro polymer.
    Type: Grant
    Filed: July 23, 1980
    Date of Patent: September 15, 1981
    Assignee: Nippon Petrochemical Company, Limited
    Inventors: Atsushi Sato, Isoo Shimizu, Masahito Gotoh
  • Patent number: RE32162
    Abstract: A solvent for the pressure sensitive record material which consists of a normally liquid compound having 13 to 18 Carbon atoms and being represented by the following general formula: ##STR1## in which each of R.sub.1 to R.sub.5 is hydrogen, methyl group or etyl group R.sub.6 is hydrogen, methyl, ethyl, iso-propyl, n-propyl, tert-buthyl or sec-buthyl group; and the preparation method of the above solvent from styrene and C.sub.7 -C.sub.10 aromatic hydrocarbons using sulfuric acid as the catalyst.
    Type: Grant
    Filed: August 29, 1979
    Date of Patent: May 27, 1986
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Atsushi Sato, Yoshiaki Aida, Isoo Shimizu