GB1204754A - Process for the preparation of ethylenic carbonyl compounds - Google Patents

Process for the preparation of ethylenic carbonyl compounds

Info

Publication number
GB1204754A
GB1204754A GB56380/68A GB5638068A GB1204754A GB 1204754 A GB1204754 A GB 1204754A GB 56380/68 A GB56380/68 A GB 56380/68A GB 5638068 A GB5638068 A GB 5638068A GB 1204754 A GB1204754 A GB 1204754A
Authority
GB
United Kingdom
Prior art keywords
methyl
ethyl
buten
carbonyl compounds
ethylenic
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.)
Expired
Application number
GB56380/68A
Inventor
Pierre Chabardes
Yvon Querou
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 SA
Original Assignee
Rhone Poulenc 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 SA filed Critical Rhone Poulenc SA
Publication of GB1204754A publication Critical patent/GB1204754A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/20—Vanadium, niobium or tantalum
    • B01J23/22—Vanadium
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/28—Molybdenum
    • 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
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
    • B01J31/0212—Alkoxylates
    • 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
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • 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
    • C07C403/02—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 containing only carbon and hydrogen atoms
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • 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
    • C07C45/68—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 by increase in the number of carbon atoms
    • C07C45/72—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/20—Vanadium, niobium or tantalum
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/32—Manganese, technetium or rhenium
    • B01J23/36—Rhenium
    • 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
    • B01J2531/50—Complexes comprising metals of Group V (VA or VB) as the central metal
    • B01J2531/56—Vanadium
    • 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

Abstract

1,204,754. Ethylenic carbonyl compounds. RHONE-POULENC S.A. 27 Nov., 1968 [28 Nov., 1967], No. 56380/68. Heading C2C. [Also in Division C1] Ethylenic carbonyl compounds (aldehydes and ketones) are prepared by isomerizing by heating an acetylenic alcohol of formula where R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are independently H, saturated or unsaturated aliphatic or cycloaliphatic radicals or aromatic or arylaliphatic radicals, either substituted or unsubstituted, or R<SP>1</SP> and R<SP>2</SP> may be linked together, in the liquid phase in the presence of a catalyst based on a transition metal of Groups V, VI or VII of the Periodic Table, specifically V, Nb, Mo, W or Re. The catalysts may be salts of inorganic or organic acids, salts or esters of acids derived from the specified metals, chelates or co-ordination complexes or metal alkyls. The products are generally of formula but where R<SP>1</SP> and R<SP>2</SP> are linked, a #-ethylenic carbonyl compound with an intracyclic double bond is also formed. Examples prepare citral; 3,7,11 - trimethyldodeca - 2,6,10 - trienal; 4,7- dimethyl - 3 - ethyl -, 3 - methyl - 3 - isobutyl -, 7 - methyl - 3 - ethyl -, 3,7 - dimethyl - 4 - ethyl -, 7 - methyl - 3 - propyl -, 3,4,4,7 - tetramethyl - and 7 - methyl - 3 - isopropyl - 2,6 - octadienal; 3 - methyl - 2 - nonenal; 2,2,6 - trimethylcyclohexylidene -, (2,6,6 - trimethylcyclohexen - 1 - yl) -, 2 - (3 - methyl - 2 - buten- 1 - yl) - cyclohexylidene - and [6 - (3 - methyl - 2 - buten - 1 - yl) - cyclohexen - 1 - yl] - acetaldehyde; 2 - methyl - 2 - nonen - 4 - one; 2 - octen - 4 - one; and 4 - phenyl - 2 - methyl - 2 - buten - 4-one. Catalysts prepared include various lower alkyl, cyclohexyl, dehydrolinalyl and tetrahydrolinalyl orthovanadates; propyl molybdate; ethyl, 1,1-dimethylpropyl, cyclohexyl and butyl orthotungstates; vanadyl acetate, hexahydrobenzoate, benzoate and stearate; vanadyl acetylacetonate; and the reaction product of MoO 3 and acetylacetone. A mixture of citral and dehydrolinalool obtained from dehydrolinalool according to the above process is reacted with acetone and NaOH to give pseudo-ionone and this is treated with H 2 SO 4 to give #-ionone.
GB56380/68A 1967-11-28 1968-11-27 Process for the preparation of ethylenic carbonyl compounds Expired GB1204754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR130019 1967-11-28

Publications (1)

Publication Number Publication Date
GB1204754A true GB1204754A (en) 1970-09-09

Family

ID=8642399

Family Applications (1)

Application Number Title Priority Date Filing Date
GB56380/68A Expired GB1204754A (en) 1967-11-28 1968-11-27 Process for the preparation of ethylenic carbonyl compounds

Country Status (10)

Country Link
JP (1) JPS5231845B1 (en)
AT (1) AT294795B (en)
BE (1) BE724532A (en)
BR (1) BR6804208D0 (en)
CH (1) CH486405A (en)
DE (1) DE1811517A1 (en)
FR (1) FR1554805A (en)
GB (1) GB1204754A (en)
NL (1) NL6816561A (en)
SE (1) SE362411B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0947492A1 (en) * 1998-03-30 1999-10-06 F. Hoffmann-La Roche Ag Process for the preparation of citral
EP0949237A1 (en) * 1998-04-07 1999-10-13 F. Hoffmann-La Roche Ag Process for the preparation of dihydrocitral
US6118027A (en) * 1998-04-20 2000-09-12 Givaudan Roure (International) Sa Preparation of unsaturated aldehydes from propargyl alcohol and conjugated diolefins

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2071288A5 (en) * 1969-12-23 1971-09-17 Rhone Poulenc Sa
CH589023A5 (en) * 1971-05-07 1977-06-30 Hoffmann La Roche
DE2516698A1 (en) * 1974-04-22 1975-10-30 Kuraray Co NEW TUNGSTEN COMPOUNDS
US4010207A (en) * 1976-01-15 1977-03-01 International Flavors & Fragrances Inc. Process for the alkylation of α, β-unsaturated aldehydes
FR2596755B1 (en) * 1986-04-03 1988-05-27 Rhone Poulenc Sante PROCESS FOR THE PREPARATION OF ETHYLENIC CARBONYL COMPOUNDS
ES2713982T3 (en) * 2012-10-08 2019-05-24 Dsm Ip Assets Bv Formulation of aroma and fragrance (III)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0947492A1 (en) * 1998-03-30 1999-10-06 F. Hoffmann-La Roche Ag Process for the preparation of citral
US6198006B1 (en) 1998-03-30 2001-03-06 Roche Vitamins Inc. Process for the manufacture of citral
EP0949237A1 (en) * 1998-04-07 1999-10-13 F. Hoffmann-La Roche Ag Process for the preparation of dihydrocitral
US6191313B1 (en) 1998-04-07 2001-02-20 Roche Vitamins Inc. Process for the manufacture of dihydrocitral
US6118027A (en) * 1998-04-20 2000-09-12 Givaudan Roure (International) Sa Preparation of unsaturated aldehydes from propargyl alcohol and conjugated diolefins

Also Published As

Publication number Publication date
AT294795B (en) 1971-12-10
JPS5231845B1 (en) 1977-08-17
BE724532A (en) 1969-05-27
FR1554805A (en) 1969-01-24
DE1811517A1 (en) 1969-07-17
CH486405A (en) 1970-02-28
NL6816561A (en) 1969-05-30
SE362411B (en) 1973-12-10
BR6804208D0 (en) 1973-01-02

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PS Patent sealed
PE20 Patent expired after termination of 20 years