WO2002010101A1 - Procede de production d'un alcool en presence d'un complexe de metaux de transition contenant un compose amide en tant que liant - Google Patents

Procede de production d'un alcool en presence d'un complexe de metaux de transition contenant un compose amide en tant que liant Download PDF

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Publication number
WO2002010101A1
WO2002010101A1 PCT/JP2001/006478 JP0106478W WO0210101A1 WO 2002010101 A1 WO2002010101 A1 WO 2002010101A1 JP 0106478 W JP0106478 W JP 0106478W WO 0210101 A1 WO0210101 A1 WO 0210101A1
Authority
WO
WIPO (PCT)
Prior art keywords
ligand
transition metal
metal complex
amide compound
producing alcohol
Prior art date
Application number
PCT/JP2001/006478
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English (en)
Japanese (ja)
Inventor
Moriyasu Masui
Yasushi Hasegawa
Original Assignee
Shionogi & Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to AU2001276690A priority Critical patent/AU2001276690A1/en
Priority to JP2002516234A priority patent/JP5041501B2/ja
Publication of WO2002010101A1 publication Critical patent/WO2002010101A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium

Abstract

L'invention concerne un procédé de production d'un alcool représenté par la formule générale (IIa), dans laquelle R?1a' et R2a'¿ représentent chacun hydrogène, un résidu organique ou un groupe formé par réduction du résidu organique, à condition que R?1a' et R2a'¿ soient liés l'un à l'autre pour former un groupe cyclique éventuellement substitué. Ledit procédé consiste à réduire un composé représenté par la formule générale (Ia) (dans laquelle R?1a et R2a¿ représentent chacun hydrogène ou un résidu organique, à condition que R?1a et R2a¿ soient liés l'un à l'autre pour former un groupe cyclique éventuellement substitué), en présence d'un complexe de métaux de transition contenant un composé α-aminocarboxamide en tant que liant, d'une base et d'un composé donneur d'hydrogène.
PCT/JP2001/006478 2000-08-01 2001-07-27 Procede de production d'un alcool en presence d'un complexe de metaux de transition contenant un compose amide en tant que liant WO2002010101A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2001276690A AU2001276690A1 (en) 2000-08-01 2001-07-27 Process for producing alcohol with transition metal complex having amide compound as ligand
JP2002516234A JP5041501B2 (ja) 2000-08-01 2001-07-27 アミド化合物を配位子とする遷移金属錯体を用いたアルコールの製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-232725 2000-08-01
JP2000232725 2000-08-01

Publications (1)

Publication Number Publication Date
WO2002010101A1 true WO2002010101A1 (fr) 2002-02-07

Family

ID=18725360

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2001/006478 WO2002010101A1 (fr) 2000-08-01 2001-07-27 Procede de production d'un alcool en presence d'un complexe de metaux de transition contenant un compose amide en tant que liant

Country Status (3)

Country Link
JP (1) JP5041501B2 (fr)
AU (1) AU2001276690A1 (fr)
WO (1) WO2002010101A1 (fr)

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007182419A (ja) * 2005-12-07 2007-07-19 Tokyo Univ Of Science プロリン誘導体及び光学活性アンチ選択性増強触媒
WO2008114891A1 (fr) 2007-03-22 2008-09-25 Sumitomo Chemical Company, Limited Réductase, gène la réductase et procédé d'utilisation associé
WO2008114892A1 (fr) 2007-03-22 2008-09-25 Sumitomo Chemical Company, Limited Réductase, gène de cette réductase, et procédé d'utilisation correspondant
WO2009005024A1 (fr) * 2007-07-03 2009-01-08 Hamari Chemicals, Ltd. Procédé de fabrication d'une amine optiquement active
WO2010093059A1 (fr) * 2009-02-16 2010-08-19 住友化学株式会社 Procédé de production d'un composé phénylacétamide
EP2228377A1 (fr) * 2009-03-12 2010-09-15 Kanto Kagaku Kabushiki Kaisha Composés organométalliques et procédé de preparation d'un composé amine
WO2011108754A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108753A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108749A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Composition et procédé de lutte contre une maladie végétale
WO2011108758A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108760A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108763A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108752A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108748A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108751A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108759A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
EP2431353A1 (fr) 2010-09-15 2012-03-21 Kanto Kagaku Kabushiki Kaisha Procédé de préparation d'un composé amine
WO2012046876A2 (fr) 2010-10-07 2012-04-12 Sumitomo Chemical Company, Limited Composition de lutte contre les maladies des plantes, et méthode de lutte contre les maladies des plantes
WO2012046877A2 (fr) 2010-10-07 2012-04-12 Sumitomo Chemical Company, Limited Composition de lutte contre les maladies des plantes, et méthode de lutte contre les maladies des plantes
WO2012050232A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et procédé de lutte anti-parasitaire
WO2012050233A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
WO2012050228A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
WO2012050235A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
WO2012050234A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
WO2012057366A2 (fr) 2010-10-28 2012-05-03 Sumitomo Chemical Company, Limited Composition antiparasitaire et procédé de lutte contre les parasites
WO2012117572A1 (fr) 2011-03-01 2012-09-07 Sumitomo Chemical Company, Limited Composition pesticide et procédé de lutte contre les parasites
US8399684B2 (en) 2007-09-17 2013-03-19 State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University Sulfonamide-based organocatalysts and method for their use
WO2013061999A1 (fr) * 2011-10-25 2013-05-02 浜理薬品工業株式会社 Procédé de production d'alcool optiquement actif
WO2014013841A1 (fr) 2012-07-20 2014-01-23 住友化学株式会社 Composition phytosanitaire et son application
WO2014013842A1 (fr) 2012-07-20 2014-01-23 住友化学株式会社 Composition phytosanitaire et son application
WO2014098201A1 (fr) 2012-12-21 2014-06-26 住友化学株式会社 Procédé pour augmenter le nombre ou le poids de graines ou de fruits
WO2015122502A1 (fr) * 2014-02-14 2015-08-20 高砂香料工業株式会社 Procédé de production de composé optiquement actif, et nouveau complexe métal-diamine
JP2017095462A (ja) * 2011-07-15 2017-06-01 浜理薬品工業株式会社 光学活性テトラヒドロキノリン類の製造方法
KR101807773B1 (ko) 2010-09-21 2017-12-11 다카사고 고료 고교 가부시키가이샤 아미드 화합물로부터 알코올 및/또는 아민을 제조하는 방법
JP2018199103A (ja) * 2017-05-26 2018-12-20 国立研究開発法人産業技術総合研究所 二酸化炭素の水素化に用いる触媒、ギ酸製造方法、水素の貯蔵方法

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Publication number Priority date Publication date Assignee Title
JP2007182419A (ja) * 2005-12-07 2007-07-19 Tokyo Univ Of Science プロリン誘導体及び光学活性アンチ選択性増強触媒
WO2008114891A1 (fr) 2007-03-22 2008-09-25 Sumitomo Chemical Company, Limited Réductase, gène la réductase et procédé d'utilisation associé
WO2008114892A1 (fr) 2007-03-22 2008-09-25 Sumitomo Chemical Company, Limited Réductase, gène de cette réductase, et procédé d'utilisation correspondant
US8192967B2 (en) 2007-03-22 2012-06-05 Sumitomo Chemical Company, Limited Reductase, gene thereof and method of using the same
US8252563B2 (en) 2007-03-22 2012-08-28 Sumitomo Chemical Company, Limited Reductase, gene thereof and method of using the same
JP5208934B2 (ja) * 2007-07-03 2013-06-12 浜理薬品工業株式会社 光学活性アミンの製造方法
WO2009005024A1 (fr) * 2007-07-03 2009-01-08 Hamari Chemicals, Ltd. Procédé de fabrication d'une amine optiquement active
US8399684B2 (en) 2007-09-17 2013-03-19 State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University Sulfonamide-based organocatalysts and method for their use
WO2010093059A1 (fr) * 2009-02-16 2010-08-19 住友化学株式会社 Procédé de production d'un composé phénylacétamide
US8624062B2 (en) 2009-02-16 2014-01-07 Sumitomo Chemical Company, Limited Method for producing phenylacetamide compound
TWI551576B (zh) * 2009-02-16 2016-10-01 Sumitomo Chemical Co Method for producing phenylacetamide compounds
EP2682382A3 (fr) * 2009-02-16 2014-02-26 Sumitomo Chemical Company, Limited Procédé de production de composé phénylacétamide
CN103641731A (zh) * 2009-02-16 2014-03-19 住友化学株式会社 苯基乙酰胺化合物的制造方法
JP2011098951A (ja) * 2009-02-16 2011-05-19 Sumitomo Chemical Co Ltd フェニルアセトアミド化合物の製造方法
CN103641731B (zh) * 2009-02-16 2015-10-28 住友化学株式会社 苯基乙酰胺化合物的制造方法
TWI570098B (zh) * 2009-02-16 2017-02-11 住友化學股份有限公司 苯乙醯胺化合物的製造方法
CN102348677A (zh) * 2009-02-16 2012-02-08 住友化学株式会社 苯基乙酰胺化合物的制造方法
AU2010214305B2 (en) * 2009-02-16 2015-11-05 Sumitomo Chemical Company, Limited Method for producing phenylacetamide compound
EP2228377A1 (fr) * 2009-03-12 2010-09-15 Kanto Kagaku Kabushiki Kaisha Composés organométalliques et procédé de preparation d'un composé amine
US9211533B2 (en) 2009-03-12 2015-12-15 Kanto Kagaku Kabushiki Kaisha Organic metal complex and process for preparing amine compound
US8481735B2 (en) 2009-03-12 2013-07-09 Kanto Kagaku Kabushiki Kaisha Organic metal complex and process for preparing amine compound
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WO2011108754A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
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WO2011108748A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
CN102834006A (zh) * 2010-03-03 2012-12-19 住友化学株式会社 植物病害防治组合物和防治植物病害的方法
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US8946298B2 (en) 2010-03-03 2015-02-03 Sumitomo Chemical Company, Limited Plant disease controlling composition and method for controlling plant disease
US8871762B2 (en) * 2010-03-03 2014-10-28 Sumitomo Chemical Company, Limited Plant disease controlling composition and method for controlling plant disease
WO2011108758A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Méthode et composition pour lutter contre les maladies des plantes
WO2011108749A2 (fr) 2010-03-03 2011-09-09 Sumitomo Chemical Company, Limited Composition et procédé de lutte contre une maladie végétale
US8940717B2 (en) 2010-03-03 2015-01-27 Sumitomo Chemical Company, Limited Plant disease controlling composition and method for controlling plant disease
US8940795B2 (en) 2010-03-03 2015-01-27 Sumitomo Chemical Company, Limited Plant disease controlling composition and method for controlling plant disease
EP2431353A1 (fr) 2010-09-15 2012-03-21 Kanto Kagaku Kabushiki Kaisha Procédé de préparation d'un composé amine
KR101807773B1 (ko) 2010-09-21 2017-12-11 다카사고 고료 고교 가부시키가이샤 아미드 화합물로부터 알코올 및/또는 아민을 제조하는 방법
WO2012046876A2 (fr) 2010-10-07 2012-04-12 Sumitomo Chemical Company, Limited Composition de lutte contre les maladies des plantes, et méthode de lutte contre les maladies des plantes
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CN103153060A (zh) * 2010-10-14 2013-06-12 住友化学株式会社 病虫害防治组合物和病虫害防治方法
WO2012050228A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
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US9668478B2 (en) 2010-10-14 2017-06-06 Sumitomo Chemical Company, Limited Pest controlling composition and method for controlling pest
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WO2012050235A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
US9370181B2 (en) 2010-10-14 2016-06-21 Sumitomo Chemical Company, Limited Pest controlling composition and method for controlling pest
WO2012050234A2 (fr) 2010-10-14 2012-04-19 Sumitomo Chemical Company, Limited Composition antiparasitaire et méthode de lutte anti-parasitaire
US9179671B2 (en) 2010-10-14 2015-11-10 Sumitomo Chemical Company, Limited Pest controlling composition and method for controlling pest
WO2012057366A2 (fr) 2010-10-28 2012-05-03 Sumitomo Chemical Company, Limited Composition antiparasitaire et procédé de lutte contre les parasites
US9049858B2 (en) 2010-10-28 2015-06-09 Sumitomo Chemical Company, Limited Pest controlling composition and method for controlling pest
WO2012117572A1 (fr) 2011-03-01 2012-09-07 Sumitomo Chemical Company, Limited Composition pesticide et procédé de lutte contre les parasites
JP2017095462A (ja) * 2011-07-15 2017-06-01 浜理薬品工業株式会社 光学活性テトラヒドロキノリン類の製造方法
US9174899B2 (en) * 2011-10-25 2015-11-03 Hamari Chemicals, Ltd. Method for producing optically active alcohols
WO2013061999A1 (fr) * 2011-10-25 2013-05-02 浜理薬品工業株式会社 Procédé de production d'alcool optiquement actif
JPWO2013061999A1 (ja) * 2011-10-25 2015-04-02 浜理薬品工業株式会社 光学活性アルコールの製造方法
US20140296584A1 (en) * 2011-10-25 2014-10-02 Hamari Chemicals, Ltd. Method for Producing Optically Active Alcohols
WO2014013841A1 (fr) 2012-07-20 2014-01-23 住友化学株式会社 Composition phytosanitaire et son application
WO2014013842A1 (fr) 2012-07-20 2014-01-23 住友化学株式会社 Composition phytosanitaire et son application
WO2014098201A1 (fr) 2012-12-21 2014-06-26 住友化学株式会社 Procédé pour augmenter le nombre ou le poids de graines ou de fruits
US10485233B2 (en) 2012-12-21 2019-11-26 Sumitomo Chemical Company, Limited Method for increasing yield of crop seeds or fruits in number or weight
WO2015122502A1 (fr) * 2014-02-14 2015-08-20 高砂香料工業株式会社 Procédé de production de composé optiquement actif, et nouveau complexe métal-diamine
JP2018199103A (ja) * 2017-05-26 2018-12-20 国立研究開発法人産業技術総合研究所 二酸化炭素の水素化に用いる触媒、ギ酸製造方法、水素の貯蔵方法

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