Patents by Inventor Teruaki Mukaiyama
Teruaki Mukaiyama 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: 6222072Abstract: A novel process for producing an optically active amine is provided. The optically active amine is adapted for use as an intermediate in synthesizing physiologically active compounds such as pharmaceuticals and agricultural chemicals, as a functional material such as a liquid crystal, and as a starting material in synthesizing fine chemicals. The process comprises the step of reacting an imine with a hydride reagent in the presence of an optically active metal compound and an alcohol compound and/or carboxylic acid compound.Type: GrantFiled: November 6, 1998Date of Patent: April 24, 2001Assignee: Mitsui Chemicals Inc.Inventors: Teruaki Mukaiyama, Kiyoaki Sugi, Takushi Nagata, Toru Yamada
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Patent number: 5859158Abstract: Disclosed in an olefin polymerization catalyst comprising a transition metal compound having at least two transition metals in which at least one of said metals is bonded to a ligand having a cyclopentadienyl skeleton, at least one of said metals is selected from Sc, Y, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W and lanthanoid metals and at least on of the others is selected from the specific transition metals; and an organoaluminum oxy-compound or an organoboron compound. Corresponding to the kind of the metal combined with said metal selected from Sc, Y, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W and lanthanoid metals, the olefin polymerization catalyst exhibit a property to give polymers having a wide molecular weight distribution in spite of the catalyst system using one kind of a transition metal compound, or to give polymers having high molecular weight and be excellent in the polymerization activity at low polymerization temperature.Type: GrantFiled: November 14, 1996Date of Patent: January 12, 1999Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Teruaki Mukaiyama, Makoto Mitani, Kunihiro Oouchi
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Patent number: 5756790Abstract: The invention provides a method for preparing an optically active alcohol comprising the step of reacting a ketone compound with a hydride reagent in the presence of an optically active metal compound. The resulting optically active alcohols are useful as intermediates for the synthesis of physiologically active compounds such as drugs and pesticides, functional materials such as liquid crystals, and raw materials for synthesis in fine chemistry. A novel optically active cobalt (II) complex useful as a catalyst is also provided.Type: GrantFiled: September 27, 1996Date of Patent: May 26, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Teruaki Mukaiyama, Kiyotaka Yorozu, Takushi Nagata, Toru Yamada, Kiyoaki Sugi
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Patent number: 5627117Abstract: Disclosed in an olefin polymerization catalyst comprising a transition metal compound having at least two transition metals in which at least one of said metals is bonded to a ligand having a cyclopentadienyl skeleton, at least one of said metals is selected from Sc, Y, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W and lanthanoid metals and at least on of the others is selected from the specific transition metals; and an organoaluminum oxy-compound or an organoboron compound. Corresponding to the kind of the metal combined with said metal selected from Sc, Y, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W and lanthanoid metals, the olefin polymerization catalyst exhibit a property to give polymers having a wide molecular weight distribution in spite of the catalyst system using one kind of a transition metal compound, or to give polymers having high molecular weight and be excellent in the polymerization activity at low polymerization temperature.Type: GrantFiled: December 27, 1994Date of Patent: May 6, 1997Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Teruaki Mukaiyama, Makoto Mitani, Kunihiro Oouchi
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Patent number: 5475157Abstract: There is disclosed a process for producing an aromatic hydroxylic compound by acid decomposition of a hydroperoxide having the general formula (I) ##STR1## wherein Ar represents an aromatic hydrocarbon group having a valence of n; and n represents an integer of 1 or 2, in the presence of an acid catalyst, thereby to provide an aromatic hydroxylic compound having the general formula (II)Ar--(OH)n (II)wherein Ar and n are the same as above defined, characterized in that tetrafluoroboric acid, hexafluorosilicic acid or hexafluorophosphoric acid is used as the acid catalyst. According to this process, the aromatic hydroxylic compound is obtained in a high yield while the by-production of hydroxyacetone is effectively suppressed.Type: GrantFiled: September 2, 1994Date of Patent: December 12, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Shintaro Araki, Hiroshi Iwasaki, Hiroyasu Ohno, Isao Hashimoto, Teruaki Mukaiyama
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Patent number: 5412128Abstract: The catalyst for olefin polymerization of the present invention contains R.sub.k.sup.1 R.sub.l.sup.2 R.sub.m.sup.3 M(SO.sub.3 R.sup.4) (M=Zr, Ti or Hf; R.sup.1-3 =a group having a cyclopentadienyl skeleton) as a catalyst component of a transition metal compound. According to the catalyst of the invention, an olefin polymer having excellent particle properties can be prepared with high polymerization activities, and further a copolymer having a narrow composition distribution can be prepared when two or more monomers are copolymerized. Of the above-mentioned transition metal compounds, a compound represented by the following formula is a novel compound unknown so far and shows excellent catalytic properties. ##STR1## (Cp=a group having a cyclopentadienyl skeleton, X=SO.sub.3 R, a halogen atom, R, OR, NR.sub.n, S(O).sub.q R, SiR.sub.3 or P (O).sub.q R.sub.Type: GrantFiled: July 9, 1993Date of Patent: May 2, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Junichi Imuta, Junji Saito, Takashi Ueda, Teruaki Mukaiyama
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Patent number: 5409874Abstract: The catalyst for olefin polymerization of the present invention contains R.sup.1.sub.k R.sup.2.sub.l R.sup.3.sub.m M(SO.sub.3 R.sup.4) (M=Zr, Ti or Hf; R.sup.1-3 =a group having a cyclopentadienyl skeleton) as a catalyst component of a transition metal compound. According to the catalyst of the invention, an olefin polymer having excellent particle properties can be prepared with high polymerization activities, and further a copolymer having a narrow composition distribution can be prepared when two or more monomers are copolymerized. Of the above-mentioned transition metal compounds, a compound represented by the following formula is a novel compound unknown so far and shows excellent catalytic properties. ##STR1## (Cp=a group having a cyclopentadienyl skeleton, X=SO.sub.3 R, a halogen atom, R, OR, NR.sub.n, S(O).sub.q R, SiR.sub.3 or P(O).sub.q R.sub.Type: GrantFiled: June 19, 1992Date of Patent: April 25, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Junichi Imuta, Junji Saito, Takashi Ueda, Teruaki Mukaiyama
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Patent number: 5072007Abstract: Process for preparing polyalkyl-2-alkoxy-7-hydroxychroman derivative of the general formula (V): ##STR1## wherein R.sup.1 denotes lower primary alkyl, R.sup.2 denotes hydrogen or lower primary alkyl and R.sup.3 denotes loweralkyl, by reacting resorcin with either an aliphatic ketone of the general formula (I): ##STR2## wherein R.sup.1 and R.sup.2 are as defined above, and an alcohol of the formula (II):R.sup.3 OH (II)wherein R.sup.3 is as defined above, in the presence of an acid catalyst, or an aliphatic ketone acetal of the general formula (III): ##STR3## wherein R.sup.1, R.sup.2 and R.sup.3 are as defined above, in the presence of an acid catalyst.Type: GrantFiled: July 3, 1990Date of Patent: December 10, 1991Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Daisuke Fukuoka, Takeshi Ishitoku, Katsuya Takahashi, Takashi Tashiro, Junichi Imuta, Hiroaki Tan, Masaharu Ishiguro, Noriaki Kihara, Teruaki Mukaiyama
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Patent number: 4814500Abstract: A novel cyanoguanidine derivative represented by the following general formula (I): ##STR1## wherein X stands for a hydrogen atom, a chlorine atom or a bromine atom, and R stands for a lower alkyl group, is an effective precursor for the synthesis of N-cyano-N'-methyl-N"-(2-(5-methyl-4-imidazolylmethylthio(ethyl)-guanidine (Cimetidine) which has an action of controlling secretion of gastric acid and is valuable as an agent for the remedy of a gastric ulcer.This cyanoguanidine derivative is prepared by reacting a methylvinylketone derivative with a mercaptoguanidine derivative or by reacting an amidinoketone derivative with a halogenating agent.Type: GrantFiled: September 1, 1987Date of Patent: March 21, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Noriaki Kihara, Teruaki Mukaiyama, Takeshi Ishitoku, Katsuya Takahashi
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Patent number: 4808726Abstract: N-cyano-N'-methyl-N"-(2-(5-methyl-4-imidazolylmethylthio)ethyl)guanidine (Cimetidine), which is valuable as an agent for controlling secretion of gastric acid, is prepared in a high yield by reacting N-cyano-N'-methyl-N"-(2-(butane-2,3-dionyl)thioethyl)-guanidine as the starting compound with an ammonium salt of a carboxylic acid and formaldehyde.Type: GrantFiled: September 1, 1987Date of Patent: February 28, 1989Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Isao Hashimoto, Ikuo Tomino, Houji Kato, Noriaki Kihara, Teruaki Mukaiyama
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Patent number: 4616092Abstract: An optically active or inactive .beta.-formyl-.beta.-hydroxy ester of the formula (1), ##STR1## wherein R.sup.1 represents a C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.14 aralkyl group, R.sup.2 represents a C.sub.1 -C.sub.4 alkyl group and R.sup.3 represents a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, and a method for producing the same which comprises reacting an optically active or inactive compound of the formula (2), ##STR2## wherein A represents a C.sub.6 -C.sub.14 aryl group and R.sup.1 is as defined above, with an .alpha.-halo ester of the formula (3), ##STR3## wherein X represents a halogen atom and R.sup.2 and R.sup.3 are as defined above, in the presence of zinc, followed by hydrolysis, or reacting an ester of the formula (4),R.sup.3 CH.sub.2 COOR.sup.2 (4)wherein R.sup.2 and R.sup.Type: GrantFiled: February 18, 1981Date of Patent: October 7, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4584387Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.Type: GrantFiled: January 13, 1983Date of Patent: April 22, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4383122Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.Type: GrantFiled: April 27, 1981Date of Patent: May 10, 1983Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4337346Abstract: An optically active or racemic .alpha.-hydroxyaldehyde represented by the general formula (2), ##STR1## wherein R.sub.1 represents a C.sub.6 -C.sub.14 aryl group, C.sub.1 -C.sub.10 alkyl group, C.sub.3 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7 -C.sub.14 aralkyl group, or a group containing a functional group in the organic portion of said groups and R.sub.2 represents a C.sub.1 -C.sub.10 alkyl group, C.sub.2 -C.sub.10 alkenyl group, C.sub.2 -C.sub.10 alkynyl group, C.sub.7-C.sub.14 aralkyl group, C.sub.6 -C.sub.14 aryl group, or a group containing a functional group in the organic portion of these groups, which is an important intermediate for preparation of pharmaceuticals and agricultural chemicals, and prepared by allowing an optically active or racemic compound represented by the general formula (1), ##STR2## (wherein A represents a C.sub.6 -C.sub.14 aryl group or a C.sub.1 -C.sub.4 alkyl or alkoxy group- or halogen-substituted C.sub.6 -C.sub.14 aryl group and R.sub.Type: GrantFiled: October 30, 1979Date of Patent: June 29, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito, Masatoshi Asami
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Patent number: 4328378Abstract: A method for producing optically active or racemic 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane characterized by reducing optically active or racemic 2-hydroxy-2,6-dimethyl-6-heptenal and oxidizing the resuling optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol, and optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol.Type: GrantFiled: February 9, 1981Date of Patent: May 4, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito
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Patent number: 4276217Abstract: A method for producing optically active or racemic 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane characterized by reducing optically active or racemic 2-hydroxy-2,6-dimethyl-6-heptenal and oxidizing the resulting optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol, and optically active or racemic 2,6-dimethyl-6-heptene-1,2-diol.Type: GrantFiled: July 21, 1980Date of Patent: June 30, 1981Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Yoji Sakito
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Patent number: 4206310Abstract: An improved process for producing an ester from a carboxylic acid and an alcohol which comprises reacting said carboxylic acid with said alcohol by the use of a 1-substituted-2-halopyridinium salt or a 1-substituted-2-haloquinolinium salt as a condensing agent in the presence of a hydrogen halide captor. According to this process, various esters, even if they have some steric hindrances, may be obtained in good yields.Type: GrantFiled: September 8, 1978Date of Patent: June 3, 1980Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Masahiro Usui, Kazuhiko Saigo, Eiichiro Shimada
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Patent number: 4105673Abstract: An improved process for producing a large ring lactone which comprises subjecting a hydroxy acid to intramolecular condensation by the use of a 1-substituted-2-halopyridinium salt or a 1-substituted-2-haloquinolinium salt as a condensing agent in the presence of an acid captor in an anhydrous organic solvent. According to this process, a variety of lactones, even complex lactones such as macrolides can be obtained in good yields.Type: GrantFiled: September 20, 1976Date of Patent: August 8, 1978Assignee: Sumitomo Chemical Company, LimitedInventors: Teruaki Mukaiyama, Masahiro Usui, Kazuhiko Saigo
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Patent number: 3937718Abstract: An improved and novel process for the preparation of a carboxylic acid ester which comprises reacting a carboxylic acid with an alcohol or a sulfenic acid ester thereof in the presence of a tertiary phosphine and a disulfide of a mercaptoheterocyclic compound containing a nitrogen-carbon double bond with which the disulfide linkage is conjugated.Type: GrantFiled: November 17, 1970Date of Patent: February 10, 1976Assignee: Sankyo Company LimitedInventors: Teruaki Mukaiyama, Masaaki Ueki, Rei Matsueda, Hiroshi Maruyama