Isomerization Patents (Class 568/384)
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Patent number: 9573872Abstract: The present invention relates to a process of manufacturing compound having stereogenic centers from a mixture of E/Z isomers of unsaturated compounds having prochiral double bonds. The hydrogenation product has a specific desired configuration at the stereogenic centers. The process involves an asymmetric hydrogenation and an isomerization step. The process is very advantageous in that it forms the desired chiral product from a mixture of stereoisomers of the starting product in an efficient way.Type: GrantFiled: December 18, 2013Date of Patent: February 21, 2017Assignee: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Thomas Netscher, Jonathan Alan Medlock, René Tobias Stemmler, Gerardus Karel Maria Verzijl, Andreas Hendrikus Maria De Vries
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Patent number: 8802898Abstract: Isomerization of ?-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding ?,?-dienones of formula II by treatment with a basic ion exchange resin.Type: GrantFiled: April 18, 2011Date of Patent: August 12, 2014Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Reinhard Karge, Thomas Netscher, Yann Pressel
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Publication number: 20130197272Abstract: Isomerization of ?-keto-allenes of the general formula I wherein R1 is hydrogen, methyl or ethyl, in particular hydrogen or methyl; R2 is hydrogen or methyl; R3 is hydrogen or methyl, in particular methyl and R4 is an aliphatic hydrocarbon residue containing 1-37 carbon atoms, into corresponding ?,?-dienones of formula II by treatment with a basic ion exchange resin.Type: ApplicationFiled: April 18, 2011Publication date: August 1, 2013Applicant: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Reinhard Karge, Thomas Netscher, Yann Pressel
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Patent number: 7176177Abstract: 4,8-dimethyl-3,7-nonadien-2-one has aromatizing properties and increases the extendibility and intensity of the aroma when used in an aroma composition.Type: GrantFiled: December 4, 2000Date of Patent: February 13, 2007Assignee: Symrise GmbH & Co. KGInventors: Stefan Lambrecht, Günter Kindel, Erich Dilk, Matthias Güntert
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Patent number: 6933413Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.Type: GrantFiled: July 2, 2002Date of Patent: August 23, 2005Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
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Publication number: 20030149309Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.Type: ApplicationFiled: February 26, 2003Publication date: August 7, 2003Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Patent number: 6310258Abstract: The invention provides a process for preparing 1,3-diketones by rearrangement of the isomeric enol ester in a tube reactor comprising a heated portion and an unheated insulated portion which can optionally be provided with cooling means. The unheated portion of the reactor has a higher volume to surface ratio than the heated portion of the reactor. The reaction can be carried out adiabatically in the unheated portion of the reactor. The process and apparatus provide higher yields and selectivity to the 1,3-diketones.Type: GrantFiled: July 31, 2000Date of Patent: October 30, 2001Assignee: Wacker Chemie GmbHInventors: Dominik Dempf, Thomas List, Wolfgang Deinhammer, Georges Heyen
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Patent number: 6300523Abstract: This invention is intended to provide a method for producing pinacoline by means of pinacol rearrangement in supercritical water, which affords an extremely high reaction rate without the addition of high concentrations of acid, and this invention is directed to a method for increasing the reaction rate during organic synthesis by utilizing the supply of protons from water under noncatalytic conditions in supercritical water, a method of pinacol rearrangement comprising the production of pinacoline by pinacol rearrangement under noncatalytic conditions without the addition of an acid catalyst in supercritical water, and a method of synthesis comprising the production of cyclic compounds from pinacol under noncatalytic conditions without the addition of an acid catalyst around the critical point (375 to 380° C., 22.5 to 25 MPa) in supercritical water.Type: GrantFiled: October 27, 1999Date of Patent: October 9, 2001Assignee: Agency of Industrial Science and TechnologyInventors: Yutaka Ikushima, Osamu Sato
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Patent number: 5576462Abstract: A process for the preparation of .alpha.-hydroxyketones of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 denote hydrogen or C.sub.1 -C.sub.8 alkyl orR.sub.1 and R.sup.3 together form a C.sub.2 -C.sub.10 alkylene chain optionally mono- to tri-substituted by methyl and/or ethyl andR.sup.5 denotes hydrogen, methyl or ethyl,from 2,3-epoxyalcohols of the general formula II ##STR2## in which R.sup.1, R.sup.2, R.sup.3, and R.sup.4 have the above meanings, at temperatures of from -10.degree. to 120.degree. C. and pressures of from 0.01 to 20 bar in the presence of a catalyst, wherein the catalyst used is a hydridocobalt compound, and the preparation of 2,3-epoxyalcohols II from 3-hydroperoxy alkenes III and their preparation from alkenes IV using oxygen or gas mixtures containing oxygen.Type: GrantFiled: August 3, 1995Date of Patent: November 19, 1996Assignee: BASF AktiengesellschaftInventors: Norbert Rieber, Joaquim H. Teles
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Patent number: 5457238Abstract: This invention concerns a process for the preparation of fluoroketones by the isomerization of corresponding epoxides, in the presence of an aluminum chlorofluoride catalyst. Fluorinated ketones are useful intermediates for the synthesis of various fluorinated compounds.Type: GrantFiled: June 30, 1994Date of Patent: October 10, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Viacheslav A. Petrov, Bruce E. Smart
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Patent number: 5102581Abstract: Process for the preparation of: ##STR1## by oxidative decarboxylation of an allyl .beta.-ketoester: ##STR2## in an organic solvent, in the presence of a palladium-based catalyst. The organic solvent selected from an amide, a nitrile, or a dinitrile.Type: GrantFiled: June 21, 1990Date of Patent: April 7, 1992Assignee: Rhone-Poulenc SanteInventors: Claude Mercier, Gerard Mignani
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Patent number: 5032323Abstract: Epoxides are isomerized to ketones by contacting the epoxides with a catalyst effective amount of a substantially fully hydrogenated palladium catalyst at a temperature of from about 200.degree. C. to about 300.degree. C. while contacting the epoxides with hydrogen at a partial pressure of equal to or less than one atmosphere.Type: GrantFiled: March 28, 1990Date of Patent: July 16, 1991Assignee: Henkel Research CorporationInventor: Michael J. Virnig
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Patent number: 4980511Abstract: Aldehydes and ketones are prepared from epoxides of the formula ##STR1## where R.sup.1 and R.sup.2 are each alkyl, alkenyl, aryl, alkoxy or aralkyl and R.sup.3 has the same meanings or is hydrogen, by a catalytic rearrangement reaction in the presence of various catalysts, in particular zeolites of the pentasil type.Type: GrantFiled: September 25, 1987Date of Patent: December 25, 1990Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Norbert Goetz, Leopold Hupfer, Helmut Lermer
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Patent number: 4950797Abstract: A process for the preparation of carbonyl compounds by catalyzed isomerization of allyl alcohols in a tertiary phosphine or phosphite ester in the presence of a rhodium compound at a temperature of from 80.degree. C. to 180.degree. C., a carrier gas being passed through the reaction mixture and the carbonyl compound being separated from the emergent gas mixture by cooling.Type: GrantFiled: June 1, 1988Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Rudolf Kummer, Werner Bertleff, Michael Roeper
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Patent number: 4925985Abstract: A process for the production of 4,6-dimethyl-7-hydroxynonan-3-one of specific stereochemistry is disclosed. The process results in an active (+)-serricornin.Type: GrantFiled: November 2, 1988Date of Patent: May 15, 1990Assignee: Philip Morris IncorporatedInventors: David L. Williams, William B. Edwards, III, Richard H. Cox, Daryl L. Faustini, Surnease Drew
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Patent number: 4845301Abstract: A process for the preparation of .alpha.-hydroxyketones ##STR1## having a high purity in a good yield from a compound ##STR2## by rearrangement reaction in aqueous alkaline solution, where R.sub.1 and R.sub.3 each represent an alkyl, alkenyl or aryl group, R.sub.2 represents a hydrogen atom or an alkyl, alkenyl or aryl group, and X represents hydroxyl group or a halogen atom.Type: GrantFiled: September 8, 1987Date of Patent: July 4, 1989Assignee: Daicel Chemical Industries, Ltd.Inventors: Kazuo Sato, Noritsugu Yamasaki, Ichirou Takase
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Patent number: 4749814Abstract: Ethylenic carbonyl compounds of formula ##STR1## are made by the isomerization of acetylenic alcohols of formula ##STR2## in the presence of a catalyst consisting of a titanium derivative, a copper or silver derivative, and, if required, an acid, which may be in the form of an ester or anhydride, or an inorganic ester.Type: GrantFiled: April 2, 1987Date of Patent: June 7, 1988Assignee: Rhone-Poulenc SanteInventor: Pierre Chabardes
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Patent number: 4734529Abstract: The method for the isomerization of oxiranes of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 are hydrogen; R.sub.2 is alkyl or alkylene groups of 3 to 26 carbon atoms or the phenyl group which may also be substituted, and R.sub.4 is hydrogen or alkyl from 1 to 26 carbon atoms and in which the carbon atoms of the epoxy ring can also form components of a cyclic system, wherein as a catalyst there is used alkali iodide and a polyethyleneglycol with an average mol mass of 400 to 10,000 with a boiling point, preferably above the boiling point of the carbonyl compounds that are formed.Type: GrantFiled: December 22, 1986Date of Patent: March 29, 1988Assignee: Degussa AktiengesellschaftInventors: Marion Berg, Andreas Grund, Guenter Prescher
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Patent number: 4721820Abstract: A process for isomerizing allylic ethers is disclosed. In this process a compound having the structural formulaCH.sub.2 .dbd.CH--CH(OR)--R.sup.1where R is hydrocarbyl; and R.sup.1 is an organo group is contacted with a hydroxy-containing compound and a catalytically effective amount of a catalyst selected from the group consisting of cupric chloride, cupric bromide, a mixture of cupric chloride and palladium chloride, a mixture of cupric chloride and palladium bromide, a mixture of cupric bromide and palladium chloride and a mixture of cupric bromide and palladium bromide whereby a compound having the structural formulaRO--CH.sub.2 --CH.dbd.CH--R.sup.1where R and R.sup.1 have the meanings given above is formed.Type: GrantFiled: December 22, 1986Date of Patent: January 26, 1988Assignee: National Distillers and Chemical CorporationInventor: Ronnie M. Hanes
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Patent number: 4695673Abstract: An acylated 1,3-dicarbonyl compound is produced by rearrangement of the corresponding enol ester in the presence of a cyanide source. In one embodiment the cyanide source is employed with a molar excess of a moderate base, with respect to the enol ester. In another embodiment, the cyanide source is a stoichiometric amount, with respect to the enol ester, of potassium or lithium cyanide and a catalytic amount of a crown ether is used.Type: GrantFiled: June 9, 1986Date of Patent: September 22, 1987Assignee: Stauffer Chemical CompanyInventors: James B. Heather, Pamela D. Milano
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Patent number: 4694107Abstract: Ketones are prepared by isomerization of aldehydes at elevated temperatures over zeolites.Type: GrantFiled: July 2, 1986Date of Patent: September 15, 1987Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Franz Merger, Wolf D. Mross, Rolf Fischer
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Patent number: 4609764Abstract: Stereoisomers having no cigarette beetle's sex pheromone activity contained in synthesized 4,6-dimethyl-7-hydroxy-nonan-3-one which is an equilibrium mixture of eight stereoisomers may be converted into stereoisomer having said sex pheromone activity by repeating column chromatographic fractionation, epimerization with an acidic or a basic catalyzer and/or racemization with a basic catalyzer in relation to said 3-one compound.Type: GrantFiled: December 26, 1984Date of Patent: September 2, 1986Assignees: The Japan Tobacco & Salt Public Corporation, Fuji Flavor Company, LimitedInventors: Mori Masataka, Chuman Tatsuji, Kato Kunio, Ono Mikio
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Patent number: 4537995Abstract: A process of isomerizing branched aldehydes to ketones is provided which comprises contacting at isomerization conditions a branched aldehyde with a zeolite catalyst of the formula: ##EQU1## wherein M is selected from the group consisting of a mixture of alkali metal cations, especially sodium, and tetraalkylammonium cations, the alkyl groups of which preferably contain 2 to 5 carbon atoms, and x is at least 5. The contacting is conducted at a temperature of from about 200.degree. C. to about 600.degree. C. and at a pressure of from about 20 psig to about 100 psig. The branched aldehyde is contacted in the presence of water in a molar ratio of water-to-aldehyde of up to about 20 to 1.Type: GrantFiled: November 7, 1983Date of Patent: August 27, 1985Assignee: Celanese CorporationInventors: H. Clay Linstid, III, Gerald S. Koermer
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Patent number: 4508923Abstract: There is disclosed an improved process for oxidizing a hydrocarbon to produce a reaction mixture containing the corresponding organic hydroperoxide of said hydrocarbon and decomposing said hydroperoxide to provide a mixture containing reaction products of said decomposition reaction, including alcohol and/or ketone products, comprising effecting said oxidation and/or decomposition in the presence of a catalytic quantity of a catalyst system comprised of ruthenium and chromium.Type: GrantFiled: February 22, 1983Date of Patent: April 2, 1985Assignee: Atlantic Richfield CompanyInventors: Paul D. Taylor, Michael T. Mocella
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Patent number: 4476147Abstract: A process for augmenting or enhancing the aroma or taste of alliaceous flavors, particularly garlic flavors, by augmenting or enhancing the garlic and green aroma and taste nuances of alliaceous-flavored foodstuffs comprising the step of adding to a alliaceous-flavored foodstuff an aroma or taste augmenting quantity of a mixture of cis and trans isomers of a compound having the structure: ##STR1## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond.Type: GrantFiled: October 17, 1983Date of Patent: October 9, 1984Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, James M. Sanders, James N. Siano
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Patent number: 4460801Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.Type: GrantFiled: June 28, 1983Date of Patent: July 17, 1984Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4451672Abstract: Methyl ethyl ketone is produced in quantitative yields by isomerizing 1,2-butylene oxide or isomeric mixtures of n-butylene oxides in the presence of a tertiary butyl alcohol solution of dicobalt octacarbonyl.Type: GrantFiled: January 31, 1983Date of Patent: May 29, 1984Assignee: Atlantic Richfield CompanyInventor: Roger A. Grey
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Patent number: 4424399Abstract: New unsaturated fatty alcohols of the formula: ##STR1## in which n=2 or 4 are provided and are prepared by the novel process of reacting butadiene with water in the presence of a palladium salt and orthoboric acid, B(OH).sub.3, in a polar aprotic solvent.Type: GrantFiled: September 9, 1980Date of Patent: January 3, 1984Assignee: Rhone-Poulenc IndustriesInventor: Didier Morel
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Patent number: 4421934Abstract: Process for the preparation of .delta.-ethylenic carbonyl compounds of the formula (I) by the oxy-Cope rearrangement of a diethylenic alcohol of the formula (II), in the presence of a mercuric salt: in formulae (I) and (II), R.sub.1, R.sub.2, R.sub.4, R.sub.5 and R.sub.6, which are identical or different, represent a hydrogen atom or an acyclic hydrocarbon radical and R.sub.3 represents an acyclic hydrocarbon radical, it being understood that R.sub.1 and R.sub.3 can together form a trimethylene radical, or alternatively that R.sub.3 and R.sub.4 can together form an alkylene radical containing 3 to 20 carbon atoms.Type: GrantFiled: March 5, 1982Date of Patent: December 20, 1983Assignee: Rhone-Poulenc SanteInventors: Norbert Bluthe, Jacques Gore, Max Malacria
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Patent number: 4329506Abstract: Aldehydes, such as isobutyraldehyde, are isomerized to ketones, such as methyl ethyl ketone, by contact at isomerization conditions, typically vapor-phase conditions, with a catalyst of the formula M.sub.0.15-15 M'.sub.0.05-12 O.sub.x where M is at least one of Mo and Cu and M' is a promoter, such as a Group IIB or VIII element.Type: GrantFiled: August 28, 1980Date of Patent: May 11, 1982Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Andrew S. Krupa
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Patent number: 4302608Abstract: A continuous process for the isomerization of hexafluoropropylene oxide to hexafluoroacetone comprises passing hexafluoropropylene oxide in contact with liquid antimony pentafluoride adsorbed on a solid support under conditions which substantially prevent loss of antimony pentafluoride from the reactor in which the isomerization is carried out and removing the hexafluoroacetone product at about the same rate as that at which it is formed. Hexafluoroacetone is an important industrial monomer, which can be copolymerized, for example, with ethylene and tetrafluoroethylene to a product that finds use in coating electrical wires.Type: GrantFiled: August 20, 1980Date of Patent: November 24, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward N. Squire
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Patent number: 4246200Abstract: This invention relates to compounds having the formula ##STR1## in which R.sub.F is a perfluoro radical C.sub.n F.sub.2n+1 with n=1-20, and R is a C.sub.1-20 alkyl radical, a C.sub.4-15 cycloalkyl radical, a C.sub.5-20 cycloalkyl-alkyl radical, or a C.sub.6-20 aromatic radical.Said compounds constitute valuable intermediates for the synthesis of surface-active agents.Type: GrantFiled: May 29, 1979Date of Patent: January 20, 1981Assignee: Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Claude Wakselman, Marc Tordeux
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Patent number: 4238416Abstract: A method for isomerization of fluorinated epoxy compounds by contacting with a catalyst to produce the corresponding fluorinated carbonyl compounds, which is characterized in that the catalyst is a fluorinated alumina or a fluorinated silica alumina.Type: GrantFiled: January 29, 1979Date of Patent: December 9, 1980Assignee: Daikin Kogyo Co., Ltd.Inventors: Takashi Tohzuka, Yohnosuke Ohsaka
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Patent number: 4222963Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## and; .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.Type: GrantFiled: February 28, 1979Date of Patent: September 16, 1980Assignee: Kuraray Co., Ltd.Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara