WO2008111557A1 - 光学活性エポキシ化合物の製造方法 - Google Patents

光学活性エポキシ化合物の製造方法 Download PDF

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Publication number
WO2008111557A1
WO2008111557A1 PCT/JP2008/054301 JP2008054301W WO2008111557A1 WO 2008111557 A1 WO2008111557 A1 WO 2008111557A1 JP 2008054301 W JP2008054301 W JP 2008054301W WO 2008111557 A1 WO2008111557 A1 WO 2008111557A1
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WO
WIPO (PCT)
Prior art keywords
optically active
epoxy compound
active epoxy
reduce
production
Prior art date
Application number
PCT/JP2008/054301
Other languages
English (en)
French (fr)
Inventor
Shoichi Kondo
Yuya Shimada
Original Assignee
Nissan Chemical Industries, 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 Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to AU2008225526A priority Critical patent/AU2008225526A1/en
Priority to CA002680425A priority patent/CA2680425A1/en
Priority to JP2009504046A priority patent/JPWO2008111557A1/ja
Priority to US12/450,034 priority patent/US20100081808A1/en
Priority to EP08721717A priority patent/EP2133343A4/en
Publication of WO2008111557A1 publication Critical patent/WO2008111557A1/ja
Priority to IL200823A priority patent/IL200823A0/en

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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
    • B01J31/18—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
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • B01J2231/72—Epoxidation
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
    • B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
    • B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
    • 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
    • B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
    • B01J2531/46—Titanium

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epoxy Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

【課題】光学活性エポキシ化合物の製造方法の提供。 【解決手段】 　光学活性エポキシ化合物の工業的に有用な製造方法に関して、光学活性チタンサレン錯体、光学活性チタンサラレン錯体又は光学活性チタンサラン錯体の存在下おける、不飽和化合物と酸化剤との反応において、反応系中に緩衝剤又は緩衝液の添加により、従来技術よりも、触媒の分解を抑制できること、触媒使用量が低減できること、および副生成物を抑制できることを見出し、高い化学収率、光学純度で品質の良い光学活性エポキシ化合物を製造できることを見い出して本発明を完成した。 【化１】
PCT/JP2008/054301 2007-03-10 2008-03-10 光学活性エポキシ化合物の製造方法 WO2008111557A1 (ja)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU2008225526A AU2008225526A1 (en) 2007-03-10 2008-03-10 Process for production of optically active epoxy compound
CA002680425A CA2680425A1 (en) 2007-03-10 2008-03-10 Process for production of optically active epoxy compound
JP2009504046A JPWO2008111557A1 (ja) 2007-03-10 2008-03-10 光学活性エポキシ化合物の製造方法
US12/450,034 US20100081808A1 (en) 2007-03-10 2008-03-10 Process for production of optically active epoxy compound
EP08721717A EP2133343A4 (en) 2007-03-10 2008-03-10 PROCESS FOR PREPARING OPTICALLY ACTIVE EPOXY COMPOUND
IL200823A IL200823A0 (en) 2007-03-10 2009-09-08 Process for production of optically active epoxy compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007061129 2007-03-10
JP2007-061129 2007-03-10

Publications (1)

Publication Number Publication Date
WO2008111557A1 true WO2008111557A1 (ja) 2008-09-18

Family

ID=39759492

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/054301 WO2008111557A1 (ja) 2007-03-10 2008-03-10 光学活性エポキシ化合物の製造方法

Country Status (10)

Country Link
US (1) US20100081808A1 (ja)
EP (1) EP2133343A4 (ja)
JP (2) JP2008255086A (ja)
KR (1) KR20090127417A (ja)
CN (1) CN101636392A (ja)
AU (1) AU2008225526A1 (ja)
CA (1) CA2680425A1 (ja)
IL (1) IL200823A0 (ja)
RU (1) RU2009137591A (ja)
WO (1) WO2008111557A1 (ja)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010275191A (ja) * 2009-05-26 2010-12-09 Nissan Chem Ind Ltd 光学活性シス−シリルオレフィンオキシド化合物の製造方法
WO2011007877A1 (ja) * 2009-07-17 2011-01-20 日産化学工業株式会社 光学活性エポキシ化合物の製造方法、並びに該方法に用いる配位子、錯体、該配位子の製造方法、及び該錯体の製造方法

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8907032B2 (en) 2010-06-18 2014-12-09 Ramot At Tel-Aviv University Ltd. Salalen ligands and organometallic complexes
CN104379680B (zh) 2012-08-03 2017-11-28 埃克森美孚化学专利公司 具有长链支化的乙烯基封端的聚烯烃
CN104411778B (zh) 2012-08-03 2017-07-28 埃克森美孚化学专利公司 使用改性的Salan催化剂化合物制备的聚α烯烃
US9382349B2 (en) 2012-08-03 2016-07-05 Exxonmobil Chemical Patents Inc. Polyalphaolefins prepared using modified Salan catalyst compounds
EP2880006B1 (en) 2012-08-03 2017-12-20 ExxonMobil Chemical Patents Inc. Non-symmetric catalysts comprising salan ligands
EP2880098B1 (en) 2012-08-03 2018-01-10 ExxonMobil Chemical Patents Inc. Halogenated catalysts comprising salan ligands
BR112014031937A8 (pt) 2012-08-03 2021-04-06 Exxonmobil Chemical Patents Inc catalisadores compreendendo ligantes salen, sistema de catalisador, poliolefina e processo para polimerizar olefinas
CN104428324B (zh) 2012-11-02 2018-08-17 埃克森美孚化学专利公司 负载型Salan催化剂
WO2014143202A1 (en) 2013-03-13 2014-09-18 Exxonmobil Chemical Patents Inc. Diphenylamine salan catalyst
CN105392776B (zh) 2013-06-20 2019-02-12 埃克森美孚化学专利公司 硫代-Salalen催化剂
US9200099B2 (en) 2013-06-20 2015-12-01 Exxonmobil Chemical Patents Inc. Salenol catalyst
CN105142777B (zh) * 2013-06-20 2017-12-26 埃克森美孚化学专利公司 长桥Salen催化剂
WO2015088819A1 (en) 2013-12-13 2015-06-18 Exxonmobil Chemical Patents Inc. Cyclopentadienyl-substituted salan catalysts
EP3126325B1 (en) 2014-03-31 2019-04-24 ExxonMobil Chemical Patents Inc. Phenylene-bridged salalen catalysts
WO2016033720A1 (zh) * 2014-09-01 2016-03-10 中国科学院长春应用化学研究所 钛系催化剂及其制备方法和应用
JP7431155B2 (ja) * 2018-03-30 2024-02-14 持田製薬株式会社 テトラヒドロナフチルウレア誘導体の製造方法
CN109665967B (zh) * 2018-11-27 2021-09-07 暨明医药科技（苏州）有限公司 茚类化合物不对称环氧化反应用配体及其制备方法与应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05507645A (ja) * 1990-03-21 1993-11-04 リサーチ　コーポレイション　テクノロジーズ　インコーポレイテッド キラル触媒及びそれにより触媒されたエポキシ化反応
JPH09508405A (ja) * 1994-02-04 1997-08-26 スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー プロキラルなオレフィンのエポキシ化法およびそのエポキシ化に用いる触媒ならびにその触媒を調製するための中間体
WO2006087874A1 (ja) 2005-02-18 2006-08-24 Japan Science And Technology Agency 光学活性なエポキシ化合物の製造方法、並びに該方法に用いる錯体及びその製造方法
WO2007105658A1 (ja) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. 光学活性クロメンオキシド化合物の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5637739A (en) * 1990-03-21 1997-06-10 Research Corporation Technologies, Inc. Chiral catalysts and catalytic epoxidation catalyzed thereby
IT1261155B (it) * 1993-12-31 1996-05-09 P & G Spa Struttura assorbente stratificata, articolo assorbente comprendente tale struttura e metodo per la sua realizzazione.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05507645A (ja) * 1990-03-21 1993-11-04 リサーチ　コーポレイション　テクノロジーズ　インコーポレイテッド キラル触媒及びそれにより触媒されたエポキシ化反応
JPH09508405A (ja) * 1994-02-04 1997-08-26 スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー プロキラルなオレフィンのエポキシ化法およびそのエポキシ化に用いる触媒ならびにその触媒を調製するための中間体
WO2006087874A1 (ja) 2005-02-18 2006-08-24 Japan Science And Technology Agency 光学活性なエポキシ化合物の製造方法、並びに該方法に用いる錯体及びその製造方法
WO2007105658A1 (ja) * 2006-03-10 2007-09-20 Nissan Chemical Industries, Ltd. 光学活性クロメンオキシド化合物の製造方法

Non-Patent Citations (13)

* Cited by examiner, † Cited by third party
Title
"Jikken Kagaku Koza 20 Yuki Gosei II -Alcohol.Amine-", vol. 4TH ED., 1992, MARUZEN CO., LTD., pages: 213, XP008142172 *
"Jikkenkagakukoza", vol. 23
"Organic Synthesis V; Oxidation Reaction", 1991, THE CHEMICAL SOCIETY OF JAPAN, pages: 245 - 246
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 3478 - 3480
CHEM. INT. ED., vol. 44, 2005, pages 4935 - 4939
D.D. PERRIN; B. DEMPSEY: "Buffers for pH and Metal Ion Control", 1974, CHAPMAN AND HALL
GRIGOROPOULOU G. ET AL.: "A catalytic environmentally benign method for the epoxidation of unsaturated terpenes with hydrogen peroxide", TETRAHEDRON LETTERS, vol. 47, no. 26, 2006, pages 4461 - 4463, XP005458501 *
K. MATSUMOTO ET AL., ANGEW. CHEM. INT. ED., vol. 44, 2005, pages 4935 - 4939
K. MATSUMOTO; Y. SAWADA; T. KATSUKI, SYNLETT, vol. 20, 2006, pages 3545 - 3547
KAGAKU BINRAN: "Handbook of Chemistry", 1984, THE CHEMICAL SOCIETY OF JAPAN, pages: 354 - 357
See also references of EP2133343A4
SHIMADA Y. ET AL.: "Titanium-catalyzed asymmetric epoxidation of olefins with aqueous hydrogen peroxide: remarkable effect of phosphate buffer on epoxide yield", SYNLETT., vol. 15, October 2007 (2007-10-01), pages 2445 - 2447, XP008117797 *
Y. SAWADA ET AL., ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 3478 - 3480

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010275191A (ja) * 2009-05-26 2010-12-09 Nissan Chem Ind Ltd 光学活性シス−シリルオレフィンオキシド化合物の製造方法
WO2011007877A1 (ja) * 2009-07-17 2011-01-20 日産化学工業株式会社 光学活性エポキシ化合物の製造方法、並びに該方法に用いる配位子、錯体、該配位子の製造方法、及び該錯体の製造方法
JP5752036B2 (ja) * 2009-07-17 2015-07-22 日産化学工業株式会社 光学活性エポキシ化合物の製造方法、並びに該方法に用いる配位子、錯体、該配位子の製造方法、及び該錯体の製造方法

Also Published As

Publication number Publication date
EP2133343A4 (en) 2010-12-29
US20100081808A1 (en) 2010-04-01
RU2009137591A (ru) 2011-04-20
EP2133343A1 (en) 2009-12-16
IL200823A0 (en) 2010-05-17
KR20090127417A (ko) 2009-12-11
AU2008225526A1 (en) 2008-09-18
CN101636392A (zh) 2010-01-27
JP2008255086A (ja) 2008-10-23
JPWO2008111557A1 (ja) 2010-06-24
CA2680425A1 (en) 2008-09-18

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