GB1204754A - Process for the preparation of ethylenic carbonyl compounds - Google Patents
Process for the preparation of ethylenic carbonyl compoundsInfo
- 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
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
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- 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
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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.
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)
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)
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) |
-
1967
- 1967-11-28 FR FR130019A patent/FR1554805A/fr not_active Expired
-
1968
- 1968-11-20 NL NL6816561A patent/NL6816561A/xx unknown
- 1968-11-21 BR BR204208/68A patent/BR6804208D0/en unknown
- 1968-11-27 BE BE724532D patent/BE724532A/xx not_active IP Right Cessation
- 1968-11-27 JP JP43086905A patent/JPS5231845B1/ja active Pending
- 1968-11-27 GB GB56380/68A patent/GB1204754A/en not_active Expired
- 1968-11-27 SE SE16186/68A patent/SE362411B/xx unknown
- 1968-11-28 DE DE19681811517 patent/DE1811517A1/en active Pending
- 1968-11-28 CH CH1774268A patent/CH486405A/en not_active IP Right Cessation
- 1968-11-28 AT AT1157368A patent/AT294795B/en not_active IP Right Cessation
Cited By (5)
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 |
---|---|
CH486405A (en) | 1970-02-28 |
JPS5231845B1 (en) | 1977-08-17 |
NL6816561A (en) | 1969-05-30 |
FR1554805A (en) | 1969-01-24 |
SE362411B (en) | 1973-12-10 |
AT294795B (en) | 1971-12-10 |
BR6804208D0 (en) | 1973-01-02 |
DE1811517A1 (en) | 1969-07-17 |
BE724532A (en) | 1969-05-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |