JPS5414911A - Process for preparing optically active citronellal - Google Patents

Process for preparing optically active citronellal

Info

Publication number
JPS5414911A
JPS5414911A JP8062078A JP8062078A JPS5414911A JP S5414911 A JPS5414911 A JP S5414911A JP 8062078 A JP8062078 A JP 8062078A JP 8062078 A JP8062078 A JP 8062078A JP S5414911 A JPS5414911 A JP S5414911A
Authority
JP
Japan
Prior art keywords
optically active
preparing optically
active citronellal
citronellal
preparing
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
JP8062078A
Other languages
English (en)
Other versions
JPS6123775B2 (ja
Inventor
Abiron Biore Pooru
Pa Dan Deyuan
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
Publication of JPS5414911A publication Critical patent/JPS5414911A/ja
Publication of JPS6123775B2 publication Critical patent/JPS6123775B2/ja
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)
JP8062078A 1977-07-04 1978-07-04 Process for preparing optically active citronellal Granted JPS5414911A (en)

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
JPS5414911A true JPS5414911A (en) 1979-02-03
JPS6123775B2 JPS6123775B2 (ja) 1986-06-07

Family

ID=9193250

Family Applications (1)

Application Number Title Priority Date Filing Date
JP8062078A Granted JPS5414911A (en) 1977-07-04 1978-07-04 Process for preparing optically active citronellal

Country Status (7)

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

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008515843A (ja) * 2004-10-11 2008-05-15 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製造方法
JP2009502874A (ja) * 2005-07-29 2009-01-29 ビーエーエスエフ ソシエタス・ヨーロピア 光学活性ビスホスフィニルアルカンの調製方法
WO2010061909A1 (ja) 2008-11-27 2010-06-03 高砂香料工業株式会社 不斉水素化触媒
JP2010525008A (ja) * 2007-04-25 2010-07-22 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
WO2010140636A1 (ja) 2009-06-03 2010-12-09 高砂香料工業株式会社 不斉水素化触媒
EP2457655A2 (en) 2010-11-29 2012-05-30 Takasago International Corporation Catalyst for asymmetric hydrogenation comprising peptides and method for manufacturing optically active carbonyl compound using the same
US9000192B2 (en) 2010-11-29 2015-04-07 Takasago International Corporation Catalyst for asymmetric hydrogenation and method for manufacturing optically active carbonyl compound using the same
JP2017537965A (ja) * 2014-12-19 2017-12-21 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 光学活性カルボニル化合物を合成する方法

Families Citing this family (22)

* 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
ATE424465T1 (de) * 2005-11-17 2009-03-15 Basf Se Verfahren zur herstellung von citronellal
JP4938786B2 (ja) * 2005-11-17 2012-05-23 ビーエーエスエフ ソシエタス・ヨーロピア シトロネラールの生産法
CN104211566A (zh) * 2007-11-30 2014-12-17 巴斯夫欧洲公司 生产光学活性、外消旋薄荷醇的方法
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
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
ES2577979T3 (es) 2011-02-22 2016-07-19 Firmenich Sa Hidrogenacion de dienales con complejos de rodio bajo atmosfera libre de monóxido de carbono
DE102013103563A1 (de) 2013-04-10 2014-10-16 Basf Se Verfahren zur Herstellung von Citronellal
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
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
CN109071578B (zh) * 2016-05-06 2022-01-14 巴斯夫欧洲公司 P-手性膦配体及其用于不对称合成的用途
MX2021002670A (es) 2018-09-05 2021-05-12 Basf Se Preparacion continua de un compuesto de carbonilo opticamente activo mediante hidrogenacion asimetrica.
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
WO2021114021A1 (zh) 2019-12-09 2021-06-17 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
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
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
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 (en) * 1971-12-23 1977-12-06 Peter S. Gradeff Process for the semihydrogenation of citral to 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

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008515843A (ja) * 2004-10-11 2008-05-15 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製造方法
JP2009502874A (ja) * 2005-07-29 2009-01-29 ビーエーエスエフ ソシエタス・ヨーロピア 光学活性ビスホスフィニルアルカンの調製方法
US9469662B2 (en) 2005-07-29 2016-10-18 Basf Se Process for preparing optically active biophosphinylalkanes
JP2010525008A (ja) * 2007-04-25 2010-07-22 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
WO2010061909A1 (ja) 2008-11-27 2010-06-03 高砂香料工業株式会社 不斉水素化触媒
WO2010140636A1 (ja) 2009-06-03 2010-12-09 高砂香料工業株式会社 不斉水素化触媒
US8217204B2 (en) 2009-06-03 2012-07-10 Takasago International Corporation Catalyst for asymmetric hydrogenation
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
EP2457655A2 (en) 2010-11-29 2012-05-30 Takasago International Corporation Catalyst for asymmetric hydrogenation comprising peptides and method for manufacturing optically active carbonyl compound using the same
US8674144B2 (en) 2010-11-29 2014-03-18 Takasago International Corporation Catalyst for asymmetric hydrogenation and method for manufacturing optically active carbonyl compound using the same
US9000192B2 (en) 2010-11-29 2015-04-07 Takasago International Corporation Catalyst for asymmetric hydrogenation and method for manufacturing optically active carbonyl compound using the same
JP2017537965A (ja) * 2014-12-19 2017-12-21 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 光学活性カルボニル化合物を合成する方法

Also Published As

Publication number Publication date
EP0000315B1 (fr) 1980-09-17
FR2396735B1 (ja) 1980-02-01
CA1117981A (fr) 1982-02-09
IT1096979B (it) 1985-08-26
EP0000315A1 (fr) 1979-01-10
FR2396735A1 (fr) 1979-02-02
DE2860165D1 (en) 1980-12-18
JPS6123775B2 (ja) 1986-06-07
IT7825303A0 (it) 1978-07-04
US4237072A (en) 1980-12-02

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