GB1256184A - Process for the preparation of allylic primary or secondary alcohols - Google Patents

Process for the preparation of allylic primary or secondary alcohols

Info

Publication number
GB1256184A
GB1256184A GB63395/69A GB6339569A GB1256184A GB 1256184 A GB1256184 A GB 1256184A GB 63395/69 A GB63395/69 A GB 63395/69A GB 6339569 A GB6339569 A GB 6339569A GB 1256184 A GB1256184 A GB 1256184A
Authority
GB
United Kingdom
Prior art keywords
allylic
methyl
optionally
alcohols
acyl
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
GB63395/69A
Inventor
Charles Grard
Pierre Chabardes
Charles Schneider
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 GB1256184A publication Critical patent/GB1256184A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast
    • 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
    • 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
    • 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
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • 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

1,256,184. Allylic alcohols. RHONE POULENC S.A. 30 Dec., 1969 [30 Dec., 1968], No. 63395/69. Heading C2C. Allylic primary or secondary alcohols having the general formula are prepared by heating an allylic tertiary alcohol having the formula wherein R 1 and R 2 are each saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or araliphatic radicals, optionally substituted by a halogen or a hydroxy, alkoxy, acyl or acyloxy group, and optionally having their carbon chain interrupted by hetero-atoms, such as O, N or S, or functional groups such as -CO- or -CONH, to together form a single, divalent, saturated or unsaturated aliphatic radical of 2 or more carbon atoms optionally substituted by a halogen or an alkyl, cycloalkyl, aryl, aralkyl, hydroxy, alkoxy, acyl or acyloxy radical, and optionally having their carbon chain interrupted as above, and R 3 is hydrogen or the same as R 1 and R 2, in the liquid phase in the presence of a catalyst comprising a derivative of a transition metal from Group VA, VIA or VIIA of the Periodic Table. Suitable specified tertiary alcohols include linalol, nerolidol, 3- methyl - 1 - penten - 3 - ol, 2 - methyl - 3- nonen - 2 - ol, 2,2,6 - trimethyl - 1 - vinylcyclohexanol and 3-methyl-l-buten-3-ol. Suitable specified catalysts include, ammonium metavanadate, t-butyl-, t-amyl-, cyclohexyl-, and tetrahydrolinalyl - orthovanadates, ammonium molybdate and vanadyl acetylacetonate. The reaction is preferably carried out continuously at a temperature of from 50‹ to 250‹ C. under an anhydrous atmosphere in the presence of a co-catalyst e.g. ammonia.
GB63395/69A 1968-12-30 1969-12-30 Process for the preparation of allylic primary or secondary alcohols Expired GB1256184A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR181946 1968-12-30

Publications (1)

Publication Number Publication Date
GB1256184A true GB1256184A (en) 1971-12-08

Family

ID=8659427

Family Applications (1)

Application Number Title Priority Date Filing Date
GB63395/69A Expired GB1256184A (en) 1968-12-30 1969-12-30 Process for the preparation of allylic primary or secondary alcohols

Country Status (9)

Country Link
JP (1) JPS4823407B1 (en)
AT (1) AT294027B (en)
BE (1) BE743806A (en)
BR (1) BR6915641D0 (en)
CH (1) CH514520A (en)
FR (1) FR1599581A (en)
GB (1) GB1256184A (en)
NL (1) NL170528C (en)
SE (1) SE379750B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006193A (en) * 1972-03-13 1977-02-01 Kuraray Co., Ltd. Isomerization of the unsaturated alcohols
WO2001042177A1 (en) * 1999-12-06 2001-06-14 Basf Aktiengesellschaft Method for isomerising allyl alcohols
US7132576B2 (en) 2001-12-07 2006-11-07 Basf Aktiengesellschaft Method for isomerizing allyl alcohols
EP2657216A1 (en) 2012-04-27 2013-10-30 Symrise AG Method for converting farnesol to nerolidol in the presence of alpha-bisabolol

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5536648B2 (en) * 1972-06-14 1980-09-22
US4254291A (en) * 1979-08-22 1981-03-03 Scm Corporation Allylic rearrangement process

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006193A (en) * 1972-03-13 1977-02-01 Kuraray Co., Ltd. Isomerization of the unsaturated alcohols
WO2001042177A1 (en) * 1999-12-06 2001-06-14 Basf Aktiengesellschaft Method for isomerising allyl alcohols
US6566564B1 (en) 1999-12-06 2003-05-20 Basf Aktiengesellschaft Method for isomersing allyl acohols
US7132576B2 (en) 2001-12-07 2006-11-07 Basf Aktiengesellschaft Method for isomerizing allyl alcohols
EP2657216A1 (en) 2012-04-27 2013-10-30 Symrise AG Method for converting farnesol to nerolidol in the presence of alpha-bisabolol
US9199900B2 (en) 2012-04-27 2015-12-01 Symrise Ag Method for converting farnesol to nerolidol in the presence of alpha-bisabolol

Also Published As

Publication number Publication date
DE1965377A1 (en) 1970-07-16
DE1965377B2 (en) 1977-03-10
SE379750B (en) 1975-10-20
FR1599581A (en) 1970-07-15
NL6919194A (en) 1970-07-02
BE743806A (en) 1970-06-29
AT294027B (en) 1971-11-10
JPS4823407B1 (en) 1973-07-13
NL170528C (en) 1982-11-16
CH514520A (en) 1971-10-31
BR6915641D0 (en) 1973-05-10
NL170528B (en) 1982-06-16

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