FR2396735A1 - Procede de preparation de citronellal optiquement actif - Google Patents

Procede de preparation de citronellal optiquement actif

Info

Publication number
FR2396735A1
FR2396735A1 FR7721377A FR7721377A FR2396735A1 FR 2396735 A1 FR2396735 A1 FR 2396735A1 FR 7721377 A FR7721377 A FR 7721377A FR 7721377 A FR7721377 A FR 7721377A FR 2396735 A1 FR2396735 A1 FR 2396735A1
Authority
FR
France
Prior art keywords
optically active
preparation process
citronellal
active citronellal
preparation
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.)
Granted
Application number
FR7721377A
Other languages
English (en)
Other versions
FR2396735B1 (fr
Inventor
Paul Aviron-Violet
Tuan-Phat Dang
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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7721377A priority Critical patent/FR2396735A1/fr
Priority to DE7878420001T priority patent/DE2860165D1/de
Priority to EP78420001A priority patent/EP0000315B1/fr
Priority to US05/920,981 priority patent/US4237072A/en
Priority to CA000306584A priority patent/CA1117981A/fr
Priority to IT25303/78A priority patent/IT1096979B/it
Priority to JP8062078A priority patent/JPS5414911A/ja
Publication of FR2396735A1 publication Critical patent/FR2396735A1/fr
Application granted granted Critical
Publication of FR2396735B1 publication Critical patent/FR2396735B1/fr
Granted legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • 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
    • B01J31/1845—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 phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • B01J31/188—Amide derivatives thereof
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • B01J31/2414—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • 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
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
    • B01J31/2457—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom comprising aliphatic or saturated rings, e.g. Xantphos
    • 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
    • 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
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • 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
    • 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
    • B01J31/20—Carbonyls

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Procédé de préparation de citronellal optiquement actif caractérisé en ce que l'on hydrogène le néral ou le géranial en présence d'un catalyseur constitué par un complexe soluble dans le milieu réactionnel, formé à partir d'un dérivé du rhodium et d'une phosphine chirale. Ce procédé permet d'accéder au d-citronellal intermédiaire de la synthèse du (-) (1S) menthol.
FR7721377A 1977-07-04 1977-07-04 Procede de preparation de citronellal optiquement actif Granted FR2396735A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FR7721377A FR2396735A1 (fr) 1977-07-04 1977-07-04 Procede de preparation de citronellal optiquement actif
DE7878420001T DE2860165D1 (en) 1977-07-04 1978-06-14 Process for preparing optically active citronellal
EP78420001A EP0000315B1 (fr) 1977-07-04 1978-06-14 Procédé de préparation de citronellal optiquement actif
US05/920,981 US4237072A (en) 1977-07-04 1978-06-30 Preparation of optically active citronellal
CA000306584A CA1117981A (fr) 1977-07-04 1978-06-30 Procede de preparation de citronellal optiquement actif
IT25303/78A IT1096979B (it) 1977-07-04 1978-07-04 Procedimento per preparare citronellale otticamento attivo
JP8062078A JPS5414911A (en) 1977-07-04 1978-07-04 Process for preparing optically active citronellal

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7721377A FR2396735A1 (fr) 1977-07-04 1977-07-04 Procede de preparation de citronellal optiquement actif

Publications (2)

Publication Number Publication Date
FR2396735A1 true FR2396735A1 (fr) 1979-02-02
FR2396735B1 FR2396735B1 (fr) 1980-02-01

Family

ID=9193250

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7721377A Granted FR2396735A1 (fr) 1977-07-04 1977-07-04 Procede de preparation de citronellal optiquement actif

Country Status (7)

Country Link
US (1) US4237072A (fr)
EP (1) EP0000315B1 (fr)
JP (1) JPS5414911A (fr)
CA (1) CA1117981A (fr)
DE (1) DE2860165D1 (fr)
FR (1) FR2396735A1 (fr)
IT (1) IT1096979B (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2934250A1 (de) * 1979-08-24 1981-03-19 Basf Ag, 6700 Ludwigshafen Verfahren zur herstellung von olefinisch ungesaettigten carbonylverbindungen und alkoholen
FR2651152B1 (fr) * 1989-08-23 1991-11-29 Elf Aquitaine Perfectionnement a la preparation de catalyseurs chiraux a base de complexes du ruthenium et du phosphore.
ZM3391A1 (en) * 1990-08-06 1992-04-30 R & C Products Pty Ltd Insect repellent
JP3247277B2 (ja) * 1994-07-29 2002-01-15 高砂香料工業株式会社 液状ｌ−ｎ−メントール組成物及びその調製法
DE102004049631A1 (de) 2004-10-11 2006-04-20 Basf Ag Verfahren zur Herstellung optisch aktiver Carbonylverbindungen
DE102005036340A1 (de) * 2005-07-29 2007-02-01 Basf Ag Verfahren zur Herstellung optisch aktiver Bis-Phosphinylalkane
CN101415831B (zh) * 2005-11-17 2013-03-13 巴斯夫欧洲公司 用于产生香茅醛的方法
WO2007057354A1 (fr) * 2005-11-17 2007-05-24 Basf Se Procede de fabrication de citronellal
JP5479320B2 (ja) * 2007-04-25 2014-04-23 ビーエーエスエフ ソシエタス・ヨーロピア 光学活性カルボニル化合物の調製方法
ES2636456T3 (es) 2007-11-30 2017-10-05 Basf Se Procedimiento para la producción de mentol ópticamente activo y racémico
JPWO2010061909A1 (ja) 2008-11-27 2012-04-26 高砂香料工業株式会社 不斉水素化触媒
CN101747152B (zh) * 2008-12-18 2012-10-24 复旦大学 一种柠檬醛液相加氢合成不饱和醇的方法
JP5663791B2 (ja) * 2009-06-03 2015-02-04 高砂香料工業株式会社 不斉水素化触媒
JP5711209B2 (ja) 2010-03-04 2015-04-30 高砂香料工業株式会社 均一系不斉水素化触媒
EP2646150A4 (fr) 2010-11-29 2014-10-08 Takasago Perfumery Co Ltd Catalyseur pour hydrogénation asymétrique et procédé de fabrication de composé carbonylé optiquement actif à l'aide du catalyseur
JP5560464B2 (ja) 2010-11-29 2014-07-30 高砂香料工業株式会社 不斉水素化触媒
JP5916767B2 (ja) 2011-02-22 2016-05-11 フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ 一酸化炭素を含まない雰囲気下でのロジウム錯体によるジエナールの水素化
DE102013103563A1 (de) 2013-04-10 2014-10-16 Basf Se Verfahren zur Herstellung von Citronellal
WO2016097242A1 (fr) * 2014-12-19 2016-06-23 Basf Se Procédé de préparation de composés carbonyle optiquement actifs
CN105254474B (zh) * 2015-10-20 2017-07-21 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醇的方法
CN105330515B (zh) * 2015-10-20 2017-07-21 万华化学集团股份有限公司 一种光学纯香茅醇的制备方法
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
WO2017191310A1 (fr) * 2016-05-06 2017-11-09 Basf Se Ligands phosphine à chiralité p et leur utilisation à des fins de synthèse asymétrique
US11242306B2 (en) 2018-09-05 2022-02-08 Basf Se Continuous preparation of an optically active carbonyl compound by asymmetric hydrogenation
CN109851486B (zh) * 2018-12-20 2022-03-11 万华化学集团股份有限公司 一种钌络合物选择性氢化二烯酮的方法
US20230043867A1 (en) 2019-12-09 2023-02-09 Wanhua Chemical Group Co., Ltd. Preparation method for optically active citronellal
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
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

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3489786A (en) * 1964-12-10 1970-01-13 Shell Oil Co Hydrogenation process
US3849480A (en) * 1968-09-09 1974-11-19 Monsanto Co Catalytic asymmetric hydrogenation
US3860657A (en) * 1970-03-25 1975-01-14 Givaudan Corp Process for the preparation of citronellal
FR2116905A5 (fr) * 1970-12-10 1972-07-21 Inst Francais Du Petrole Nouveaux coordinats bidentes,leur fabrication et leurs applications
CA1022187A (fr) * 1971-12-23 1977-12-06 Peter S. Gradeff Procede de semi-hydrogenation du citral en citronellal
US3939188A (en) * 1972-03-24 1976-02-17 Exxon Research And Engineering Company Preparation of zerovalent phosphine substituted rhodium compounds and their use in the selective carbonylation of olefins
FR2314911A1 (fr) * 1975-06-18 1977-01-14 Rhone Poulenc Ind Procede de semi-hydrogenation du citral et de ses homologues en citronnellal et homologues du citronnellal
US4029709A (en) * 1976-02-17 1977-06-14 Rhodia, Inc. Process for the hydrogenation of citral to citronellal and of citronellal to citronellol using chromium-promoted Raney nickel catalyst

Also Published As

Publication number Publication date
JPS5414911A (en) 1979-02-03
IT7825303A0 (it) 1978-07-04
EP0000315A1 (fr) 1979-01-10
EP0000315B1 (fr) 1980-09-17
CA1117981A (fr) 1982-02-09
FR2396735B1 (fr) 1980-02-01
JPS6123775B2 (fr) 1986-06-07
IT1096979B (it) 1985-08-26
US4237072A (en) 1980-12-02
DE2860165D1 (en) 1980-12-18

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