ES2393105T3 - Procedimiento de isomerización de un ciclohexenil alquilo o una alquenil cetona - Google Patents

Procedimiento de isomerización de un ciclohexenil alquilo o una alquenil cetona Download PDF

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Publication number
ES2393105T3
ES2393105T3 ES04799031T ES04799031T ES2393105T3 ES 2393105 T3 ES2393105 T3 ES 2393105T3 ES 04799031 T ES04799031 T ES 04799031T ES 04799031 T ES04799031 T ES 04799031T ES 2393105 T3 ES2393105 T3 ES 2393105T3
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Prior art keywords
formula
acid
diene
coordinating
groups
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Expired - Lifetime
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ES04799031T
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English (en)
Spanish (es)
Inventor
Denis Jacoby
Bessaa Neffah
Christian Chapuis
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Firmenich SA
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Firmenich SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
    • C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
    • B01J31/14—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron
    • B01J31/146—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides of aluminium or boron of boron
    • 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
    • B01J31/2291—Olefins
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • 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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/543—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
    • C07C49/557—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings having unsaturation outside the 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
    • B01J2231/52—Isomerisation reactions
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/06—Halogens; Compounds thereof
    • B01J27/08—Halides
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical 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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
ES04799031T 2003-12-16 2004-11-30 Procedimiento de isomerización de un ciclohexenil alquilo o una alquenil cetona Expired - Lifetime ES2393105T3 (es)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IB0306118 2003-12-16
WOPCT/IB03/06118 2003-12-16
EP03029166 2003-12-18
EP03029166 2003-12-18
PCT/IB2004/003978 WO2005061426A1 (en) 2003-12-16 2004-11-30 Process for the isomerisation of a cyclohexenyl alkyl or alkenyl ketone

Publications (1)

Publication Number Publication Date
ES2393105T3 true ES2393105T3 (es) 2012-12-18

Family

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Family Applications (1)

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ES04799031T Expired - Lifetime ES2393105T3 (es) 2003-12-16 2004-11-30 Procedimiento de isomerización de un ciclohexenil alquilo o una alquenil cetona

Country Status (7)

Country Link
US (1) US7250536B2 (https=)
EP (1) EP1697290B1 (https=)
JP (1) JP4696077B2 (https=)
CN (1) CN100404487C (https=)
ES (1) ES2393105T3 (https=)
IL (1) IL175984A (https=)
WO (1) WO2005061426A1 (https=)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0624814D0 (en) * 2006-12-13 2007-01-24 Givaudan Sa Organic compounds
GB0624818D0 (en) * 2006-12-13 2007-01-24 Givaudan Sa Organic compounds
WO2009015360A2 (en) * 2007-07-26 2009-01-29 San Diego State University Research Foundation Catalysts for alkene isomerization and conjugating double bonds in polyunsaturated fats and oils
CN101125805B (zh) * 2007-09-14 2010-05-26 杭州格林香料化学有限公司 1-(2,6,6-三甲基环己-3-烯基)丁-2-烯-1-酮的制备方法
EP2948245B1 (en) 2013-01-23 2018-05-30 Firmenich SA Process for the preparation of 4-methylpent-3-en-1-ol derivatives
CN108101760B (zh) * 2017-12-19 2020-11-24 万华化学集团股份有限公司 一种α-环柠檬醛的合成方法
CN116867762A (zh) * 2021-02-19 2023-10-10 株式会社Api 环己烯酮化合物的制造方法
WO2025120108A1 (en) * 2023-12-08 2025-06-12 Firmenich Sa Isomerization process
WO2025125532A1 (en) * 2023-12-15 2025-06-19 Givaudan Sa Perfume ingredients and compositions containing them
WO2026017530A1 (en) 2024-07-18 2026-01-22 Firmenich Sa Ruthenium-catalyzed isomerization of cyclohexenyl aldehydes, esters, or ketones
WO2026017532A1 (en) 2024-07-18 2026-01-22 Firmenich Sa Ruthenium-catalyzed isomerization of alkenes

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4226892A (en) * 1967-11-09 1980-10-07 Firmenich Sa Flavoring with cycloaliphatic unsaturated ketones
CH537352A (fr) * 1969-08-08 1973-05-31 Firmenich & Cie Procédé pour la préparation de cétones insaturées
DE69820205T2 (de) * 1997-05-20 2004-09-30 Firmenich S.A. Ruthenium-katalysatoren und ihre verwendung zur asymmetrischen hydrierung von substraten mit schwacher koordination
US6214763B1 (en) * 1997-05-20 2001-04-10 Firmenich Sa Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates
US6175047B1 (en) * 1997-12-26 2001-01-16 Takasago International Corporation Ruthenium metathesis catalyst and method for producing olefin reaction product by metathesis reaction using the same
JP4071421B2 (ja) * 2000-06-07 2008-04-02 高砂香料工業株式会社 シクロヘキセニルメチルケトンの製造法
JP2003160529A (ja) * 2001-11-29 2003-06-03 Takasago Internatl Corp ２，２，６−トリメチルシクロヘキセニルメチルケトンの二重結合異性体組成物およびその製造法

Also Published As

Publication number Publication date
CN1890204A (zh) 2007-01-03
US20060211889A1 (en) 2006-09-21
IL175984A0 (en) 2006-10-05
EP1697290A1 (en) 2006-09-06
JP2007515421A (ja) 2007-06-14
WO2005061426A1 (en) 2005-07-07
EP1697290B1 (en) 2012-09-12
IL175984A (en) 2010-12-30
US7250536B2 (en) 2007-07-31
JP4696077B2 (ja) 2011-06-08
CN100404487C (zh) 2008-07-23

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