GB1102609A – Isomerization of acyclic terpene derivatives
– Google Patents
GB1102609A – Isomerization of acyclic terpene derivatives
– Google Patents
Isomerization of acyclic terpene derivatives
Info
Publication number
GB1102609A
GB1102609A
GB38629/65A
GB3862965A
GB1102609A
GB 1102609 A
GB1102609 A
GB 1102609A
GB 38629/65 A
GB38629/65 A
GB 38629/65A
GB 3862965 A
GB3862965 A
GB 3862965A
GB 1102609 A
GB1102609 A
GB 1102609A
Authority
GB
United Kingdom
Prior art keywords
catalyst
allo
butyl
acylates
cis
Prior art date
1964-09-23
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
GB38629/65A
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.)
International Flavors and Fragrances Inc
Original Assignee
International Flavors and Fragrances Inc
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.)
1964-09-23
Filing date
1965-09-09
Publication date
1968-02-07
1965-09-09
Application filed by International Flavors and Fragrances Inc
filed
Critical
International Flavors and Fragrances Inc
1968-02-07
Publication of GB1102609A
publication
Critical
patent/GB1102609A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
C07C5/25—Migration of carbon-to-carbon double bonds
C07C5/2506—Catalytic processes
C07C5/2525—Catalytic processes with inorganic acids; with salts or anhydrides of acids
C07C5/2543—Acids of halogen; Salts thereof
C07C5/255—Metal halides; Complexes thereof with organic compounds
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
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
C07C5/25—Migration of carbon-to-carbon double bonds
C07C5/2506—Catalytic processes
C07C5/2556—Catalytic processes with metals
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C67/00—Preparation of carboxylic acid esters
C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Abstract
Cis- and trans-ocimene and allo-dihydro-myrcene are made by the isomerization of myrcene and dihydromyrcene by contact with a catalytic amount of Rh, Ir, or a trihalide thereof, vat 60-165 DEG C. in the presence of HCl and optionally in the presence of an antioxidant. A catalytic amount is defined as 0.004-15% by wt. catalyst based on terpene. The catalyst may be supported on an inert carrier. The HCl may be added in the gaseous or aqueous form or may be contained in the catalyst as a result of an acid pre-treatment thereof. Specified antioxidants are 2, 6-di-t-butyl-4-methylphenol, 3-t-butyl-4-hydroxy-anisole, hydroquinone, the methyl ether thereof, and t-butyl-catechol. The process yields a mixture of the cis- and transisomers which may be separated by vapour phase chromatography.ALSO:Cis- and trans-ocimene, ocimenol, ocimenyl acylates, allo-dihydromyrcene, allo-dihydromyrcenol and allo-dihydromyrcenyl acylates, wherein the acyl group contains up to 4 carbon atoms, are prepared by isomerization of myrcene, myrcenol, myrcenyl acylates, dihydromyrcene, dihydromyrcenol or dihydromyrcenyl acylates by contact at 60-165 DEG C. with a catalytic amount of Rh, Ir or the trichlorides thereof in the presence of HCl and optionally in the presence of an antioxidant. A catalytic amount is defined as 0.004-15% catalyst by wt. of reactant. The catalyst may be supported on an inert carrier. The HCl may be added in the gaseous or aqueous form or the acid may be present in the catalyst as a result of an acid pretreatment thereof. Specified antioxidants are 2,6-di-t-butyl-4-methylphenol, 3 – t – butyl – 4 – hydroxy – anisole, hydroquinone, the methyl ether thereof and t-butylcatechol. Examples relate to the preparation of ocimene, ocimenol, ocimenyl acetate, allodihydromyrcene, and allo-dihydromyrcenol as cis-trans mixtures. The isomers may be separated by vapour phase chromatography.
GB38629/65A
1964-09-23
1965-09-09
Isomerization of acyclic terpene derivatives
Expired
GB1102609A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US398747A
US3344171A
(en)
1964-09-23
1964-09-23
Isomerization of terpenes with a noble metal catalyst in the presence of hydrogen chloride
Publications (1)
Publication Number
Publication Date
GB1102609A
true
GB1102609A
(en)
1968-02-07
Family
ID=23576652
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB38629/65A
Expired
GB1102609A
(en)
1964-09-23
1965-09-09
Isomerization of acyclic terpene derivatives
Country Status (6)
Country
Link
US
(1)
US3344171A
(en)
BE
(1)
BE669802A
(en)
CH
(1)
CH471757A
(en)
DE
(1)
DE1543083B1
(en)
GB
(1)
GB1102609A
(en)
NL
(1)
NL146775B
(en)
Families Citing this family (6)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3966648A
(en)
*
1971-12-23
1976-06-29
Monsanto Company
2-Alkyl-oct-5-en-2-ols in fragrance compositions
US3859366A
(en)
*
1971-12-23
1975-01-07
Monsanto Co
2-alkyl-oct-5-en-2-ols and their esters
US4066710A
(en)
*
1974-01-02
1978-01-03
Givaudan Corporation
Unsaturated alcohol
US4061667A
(en)
*
1974-01-09
1977-12-06
Monsanto Company
Cis-2-methyl-oct-5-en-2-yl acetate
US4266087A
(en)
*
1978-11-13
1981-05-05
Givaudan Corporation
Process for preparing a myrcenol, cis-ocimenol mixture substantially free of trans-ocimenol
US4254291A
(en)
*
1979-08-22
1981-03-03
Scm Corporation
Allylic rearrangement process
Family Cites Families (1)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
NL272469A
(en)
*
1961-01-04
1900-01-01
1964
1964-09-23
US
US398747A
patent/US3344171A/en
not_active
Expired – Lifetime
1965
1965-09-09
GB
GB38629/65A
patent/GB1102609A/en
not_active
Expired
1965-09-17
BE
BE669802D
patent/BE669802A/xx
unknown
1965-09-20
CH
CH1296965A
patent/CH471757A/en
not_active
IP Right Cessation
1965-09-20
NL
NL656512236A
patent/NL146775B/en
unknown
1965-09-20
DE
DE19651543083
patent/DE1543083B1/en
active
Pending
Also Published As
Publication number
Publication date
US3344171A
(en)
1967-09-26
BE669802A
(en)
1966-03-17
CH471757A
(en)
1969-04-30
NL6512236A
(en)
1966-03-24
DE1543083B1
(en)
1971-07-01
NL146775B
(en)
1975-08-15
Similar Documents
Publication
Publication Date
Title
ES480651A1
(en)
1979-12-16
Process for the preparation of ethyl acetate.
MX172202B
(en)
1993-12-07
PROCEDURE FOR INSULATING VINYL ACETATE
GB1102609A
(en)
1968-02-07
Isomerization of acyclic terpene derivatives
Spatz et al.
1958
Methyl Hydrogen Fumarate
GB1017605A
(en)
1966-01-19
Improvements in or relating to the preparation of dialkyl terephthalates
GB879728A
(en)
1961-10-11
Process for the manufacture of isoprene from 4.4-dimethylmetadioxane
ROSS et al.
1955
The Relative Stabilities of cis-trans Isomers of Bicyclic Ring Systems with Angular Methyl Groups. II
Monson
1971
Dehydrohalogenation of primary alkyl halides in hexamethylphosphoric triamide
ES424607A1
(en)
1976-06-01
Process for preparing hydroxydiphenyl
JPS5227704A
(en)
1977-03-02
Process for selective hydrogenation of compounds containing acetylenic unsaturated bonds
GB935051A
(en)
1963-08-28
Production of acrylic acid compounds
Beverly et al.
1966
Kinetic and thermodynamic control of the ratio of Markownikoff to anti-Markownikoff addition
GB1505584A
(en)
1978-03-30
Production of 1,1-dichloro-4-methylpenta-1,3-diene by an oxidative coupling process
GB1499699A
(en)
1978-02-01
Process for the preparation of 1,5-and 1,8-diaminonaphthalene
GB1077327A
(en)
1967-07-26
Process for preparing sorbic acid by the isomerization of cis-cis and cis-trans hexadiene (2:4) acids
GB1491737A
(en)
1977-11-16
Process for reducing the content of terephthalaldehyde acid methyl ester in dimethyl terephthalate
FR1262344A
(en)
1961-05-26
Process for controlling the reaction temperature in the vapor phase synthesis of vinyl acetate
JPS6252733B2
(en)
1987-11-06
Day et al.
1965
Allenes and 1, 3-dienes from the photolysis of pyrazolenines
GB1287077A
(en)
1972-08-31
Process for the isomerization of unsaturated compounds
IL38952A
(en)
1976-04-30
Process for preparing 17alpha-ethynylestriols
Staley et al.
1969
Stereochemical and kinetic aspects of the formation of allenes and acetylenes by dehydrobromination
GB1120714A
(en)
1968-07-24
Improvements in or relating to the production of carboxylic acids
JPS549212A
(en)
1979-01-24
Preparation of hydroxycitronellal
GB1118499A
(en)
1968-07-03
Method of preparing camphene
None