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WO2009068444A3 - Procédé de production de menthol racémique et optiquement actif - Google Patents

Procédé de production de menthol racémique et optiquement actif Download PDF

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Publication number
WO2009068444A3
WO2009068444A3 PCT/EP2008/065503 EP2008065503W WO2009068444A3 WO 2009068444 A3 WO2009068444 A3 WO 2009068444A3 EP 2008065503 W EP2008065503 W EP 2008065503W WO 2009068444 A3 WO2009068444 A3 WO 2009068444A3
Authority
WO
WIPO (PCT)
Prior art keywords
menthol
optically active
isopulegol
producing optically
citronellal
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2008/065503
Other languages
German (de)
English (en)
Other versions
WO2009068444A2 (fr
Inventor
Gunnar Heydrich
Gabriele Gralla
Matthias Rauls
Joachim Schmidt-Leithoff
Klaus Ebel
Wolfgang Krause
Steffen OEHLENSCHLÄGER
Christoph JÄKEL
Marko Friedrich
Eike Johannes Bergner
Nawid Kashani-Shirazi
Rocco Paciello
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to ES08854428.3T priority Critical patent/ES2636456T3/es
Priority to US12/744,110 priority patent/US8318985B2/en
Priority to MX2010005737A priority patent/MX2010005737A/es
Priority to JP2010535330A priority patent/JP5599716B2/ja
Priority to CN200880125808.5A priority patent/CN101932543B/zh
Priority to EP08854428.3A priority patent/EP2225192B1/fr
Publication of WO2009068444A2 publication Critical patent/WO2009068444A2/fr
Publication of WO2009068444A3 publication Critical patent/WO2009068444A3/fr
Anticipated expiration legal-status Critical
Priority to US13/658,003 priority patent/US9988331B2/en
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • 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
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
    • 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
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/78—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by condensation or crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne un procédé global particulièrement économique permettant la production de menthol, en particulier la production de menthol racémique et de L-menthol optiquement actif, sensiblement énantio- et diastéréomériquement pur, en utilisant le citral comme produit de départ bon marché disponible à l'échelle industrielle. Le procédé comprend les étapes suivantes : a.1) hydrogénation catalytique de néral et/ou de géranial en citronellal, b.1) cyclisation du citronellal en isopulégol en présence d'un catalyseur acide, c.1) purification de l'isopulégol par cristallisation et d.1) hydrogénation catalytique de l'isopulégol en menthol.
PCT/EP2008/065503 2007-11-30 2008-11-13 Procédé de production de menthol racémique et optiquement actif Ceased WO2009068444A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
ES08854428.3T ES2636456T3 (es) 2007-11-30 2008-11-13 Procedimiento para la producción de mentol ópticamente activo y racémico
US12/744,110 US8318985B2 (en) 2007-11-30 2008-11-13 Method for producing optically active, racemic menthol
MX2010005737A MX2010005737A (es) 2007-11-30 2008-11-13 Metodo para producir mentol racemico opticamente activo.
JP2010535330A JP5599716B2 (ja) 2007-11-30 2008-11-13 光学活性ラセミメントールを製造するための方法
CN200880125808.5A CN101932543B (zh) 2007-11-30 2008-11-13 生产光学活性、外消旋薄荷醇的方法
EP08854428.3A EP2225192B1 (fr) 2007-11-30 2008-11-13 Procédé de production de menthol racémique et optiquement actif
US13/658,003 US9988331B2 (en) 2007-11-30 2012-10-23 Method for producing optically active, racemic menthol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07122036 2007-11-30
EP07122036.2 2007-11-30

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/744,110 A-371-Of-International US8318985B2 (en) 2007-11-30 2008-11-13 Method for producing optically active, racemic menthol
US13/658,003 Continuation US9988331B2 (en) 2007-11-30 2012-10-23 Method for producing optically active, racemic menthol

Publications (2)

Publication Number Publication Date
WO2009068444A2 WO2009068444A2 (fr) 2009-06-04
WO2009068444A3 true WO2009068444A3 (fr) 2010-05-27

Family

ID=40521497

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/065503 Ceased WO2009068444A2 (fr) 2007-11-30 2008-11-13 Procédé de production de menthol racémique et optiquement actif

Country Status (7)

Country Link
US (2) US8318985B2 (fr)
EP (1) EP2225192B1 (fr)
JP (2) JP5599716B2 (fr)
CN (2) CN101932543B (fr)
ES (1) ES2636456T3 (fr)
MX (1) MX2010005737A (fr)
WO (1) WO2009068444A2 (fr)

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MX2013004872A (es) * 2010-11-02 2013-05-22 Basf Se Procesos para preparar un fenilciclohexano.
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US20150329452A1 (en) 2012-11-15 2015-11-19 Takasago International Corporation Method for producing optically active isopulegol and optically active menthol
CN103044204A (zh) * 2012-12-24 2013-04-17 广东省食品工业研究所 一种不对称合成左旋薄荷醇的方法
CN103446948A (zh) * 2013-08-27 2013-12-18 梧州市松桦化学品有限公司 反应塔
JP6544237B2 (ja) * 2013-10-23 2019-07-17 荒川化学工業株式会社 リサイクル可能な工業用共沸洗浄剤、物品の洗浄方法、工業用共沸洗浄剤の再生方法、当該再生方法により再生された工業用共沸洗浄剤、並びに洗浄再生装置
CN106132496B (zh) 2014-03-19 2020-03-13 巴斯夫欧洲公司 用于将物质从溶液中分离出来的方法和装置
RU2579122C1 (ru) * 2015-03-25 2016-03-27 Федеральное государственное бюджетное учреждение науки Новосибирский институт органической химии им. Н.Н. Ворожцова Сибирского отделения Российской академии наук (НИОХ СО РАН) Способ получения гераниаля
CN105218335B (zh) * 2015-10-20 2017-06-16 万华化学集团股份有限公司 一种由柠檬醛不对称催化氢化制备手性香茅醛的方法
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CN111056932A (zh) * 2019-12-09 2020-04-24 万华化学集团股份有限公司 一种制备光学活性香茅醛的方法
US12202792B2 (en) * 2019-12-09 2025-01-21 Wanhua Chemical Group Co., Ltd. Preparation method for optically active citronellal
CN110872217A (zh) * 2019-12-09 2020-03-10 万华化学集团股份有限公司 一种光学活性的香茅醛的制备方法
CN111004102B (zh) * 2019-12-23 2022-11-04 万华化学集团股份有限公司 一种制备光学活性香茅醛的方法及用于该方法的催化剂
CN111056933B (zh) * 2019-12-24 2022-11-08 万华化学集团股份有限公司 一种制备光学活性香茅醛的方法及用于该方法的催化剂体系
CN111269103A (zh) * 2020-02-24 2020-06-12 万华化学集团股份有限公司 一种高效制备r-香茅醛的方法
CN114011463B (zh) * 2021-11-24 2023-07-14 万华化学集团股份有限公司 一种催化剂及制备高纯度l-薄荷醇的方法
CN114349600B (zh) * 2022-01-06 2023-05-30 万华化学集团股份有限公司 一种富集l-异胡薄荷醇的制备方法
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WO2024246272A1 (fr) 2023-06-02 2024-12-05 Basf Se Procédés de préparation de citral et produits interdépendants
WO2025011972A1 (fr) 2023-07-07 2025-01-16 Basf Se Photoisomérisation de géranial et de neral
WO2025078316A1 (fr) 2023-10-13 2025-04-17 Basf Se Procédé de préparation de prénal et d'isovaléraldéhyde
EP4549617A1 (fr) 2023-10-31 2025-05-07 Basf Se Préparation de composés (cyclo)aliphatiques saturés ou éthyléniques par hydrogénation de composés (cyclo)aliphatiques insaturés éthyléniquement ou acétyléniques à l'aide d'hydrogène à faible teneur en deutérium
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WO2025108976A2 (fr) 2023-11-20 2025-05-30 Basf Se Procédé d'isomérisation d'un alcool à insaturation éthylénique
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US9988331B2 (en) 2018-06-05
CN101932543B (zh) 2014-07-30
EP2225192B1 (fr) 2017-05-03
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US20130046118A1 (en) 2013-02-21
JP2011504895A (ja) 2011-02-17
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CN101932543A (zh) 2010-12-29
MX2010005737A (es) 2010-06-09
ES2636456T3 (es) 2017-10-05
US20100249467A1 (en) 2010-09-30
CN104211566A (zh) 2014-12-17
EP2225192A2 (fr) 2010-09-08

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