GB1457025A - Process for the manufacture of oxo compounds - Google Patents

Process for the manufacture of oxo compounds

Info

Publication number
GB1457025A
GB1457025A GB1834474A GB1834474A GB1457025A GB 1457025 A GB1457025 A GB 1457025A GB 1834474 A GB1834474 A GB 1834474A GB 1834474 A GB1834474 A GB 1834474A GB 1457025 A GB1457025 A GB 1457025A
Authority
GB
United Kingdom
Prior art keywords
denotes
formula
phenyl
radical
silanol
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
GB1834474A
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.)
Roche Products Ltd
Original Assignee
Roche Products Ltd
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 Roche Products Ltd filed Critical Roche Products Ltd
Priority to GB1834474A priority Critical patent/GB1457025A/en
Priority to CH484075A priority patent/CH612169A5/en
Priority to DE19752518031 priority patent/DE2518031A1/en
Priority to FR7512790A priority patent/FR2268775B1/fr
Priority to JP4922575A priority patent/JPS548651B2/ja
Priority to BE155754A priority patent/BE828372A/en
Priority to AT321375A priority patent/AT339270B/en
Priority to NL7504943.A priority patent/NL163497C/en
Publication of GB1457025A publication Critical patent/GB1457025A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/005—Compounds of elements of Group 5 of the Periodic System without metal-carbon linkages
    • 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
    • B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
    • 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
    • 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
    • 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
    • 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
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/225—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
    • C07C47/263—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups acyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0836—Compounds with one or more Si-OH or Si-O-metal linkage
    • 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
    • B01J2531/50—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
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Abstract

It has been found that secondary or tertiary acetylenecarbinols can be isomerised catalytically in a surprisingly simple manner with good yields and high conversion rates to give the corresponding alpha , beta -unsaturated aldehydes or ketones, when the isomerisation is carried out in the presence of a hydrocarbylsiloxyvanadium oxide catalyst of the formula <IMAGE> in which KW denotes a hydrocarbon radical from the series consisting of lower alkyl, cycloalkyl, phenyl or phenyl-lower-alkyl, it being possible for the phenyl radical to be substituted by one or more electron-attracting groups, and R is KW or denotes the radical -Si(KW)3; m denotes the number 1, 2 or 3 and n denotes the number 0, 1 or 2, the total of m and n being 3, and in the presence of a silanol of the formula <IMAGE> the catalyst of the formula III and/or the silanol of the formula IV having at least one phenyl radical which has one or more electron-attracting groups. Using this catalyst system, the isomerisation reactions can be carried out in a relatively short time in a temperature of between approximately 20 and approximately 150 DEG C.
GB1834474A 1974-04-26 1974-04-26 Process for the manufacture of oxo compounds Expired GB1457025A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB1834474A GB1457025A (en) 1974-04-26 1974-04-26 Process for the manufacture of oxo compounds
CH484075A CH612169A5 (en) 1974-04-26 1975-04-16 Process for the preparation of oxo compounds
DE19752518031 DE2518031A1 (en) 1974-04-26 1975-04-23 PROCESS FOR PREPARING OXO COMPOUNDS
FR7512790A FR2268775B1 (en) 1974-04-26 1975-04-24
JP4922575A JPS548651B2 (en) 1974-04-26 1975-04-24
BE155754A BE828372A (en) 1974-04-26 1975-04-25 PROCESS FOR THE PREPARATION OF OXO COMPOUNDS
AT321375A AT339270B (en) 1974-04-26 1975-04-25 PROCESS FOR PRODUCING OXO COMPOUNDS BY CATALYTIC ISOMERIZATION
NL7504943.A NL163497C (en) 1974-04-26 1975-04-25 METHOD FOR PREPARING OXIC COMPOUNDS.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1834574 1974-04-26
GB1834474A GB1457025A (en) 1974-04-26 1974-04-26 Process for the manufacture of oxo compounds

Publications (1)

Publication Number Publication Date
GB1457025A true GB1457025A (en) 1976-12-01

Family

ID=26253328

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1834474A Expired GB1457025A (en) 1974-04-26 1974-04-26 Process for the manufacture of oxo compounds

Country Status (7)

Country Link
JP (1) JPS548651B2 (en)
AT (1) AT339270B (en)
CH (1) CH612169A5 (en)
DE (1) DE2518031A1 (en)
FR (1) FR2268775B1 (en)
GB (1) GB1457025A (en)
NL (1) NL163497C (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5086067A (en) * 1989-12-18 1992-02-04 G. D. Searle & Co. Ltb4 synthesis inhibitors
US5112864A (en) * 1991-05-30 1992-05-12 G. D. Searle & Co. PLA2 inhibitors as antiinflammatories
US5217981A (en) * 1989-12-18 1993-06-08 G. D. Searle & Co. LTB4 synthesis inhibitors
US5356919A (en) * 1991-05-30 1994-10-18 G. D. Searle & Co. Leukotriene B4 synthesis inhibitors
WO2016059152A1 (en) * 2014-10-16 2016-04-21 Dsm Ip Assets B.V. Method for producing specific alpha, beta-unsaturated aldehydes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019088597A1 (en) 2017-10-30 2019-05-09 주식회사 엘지화학 Super absorbent polymer nonwoven fabric and manufacturing method therefor

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1409323A (en) * 1972-11-02 1975-10-08 Roche Products Ltd Process for the manufacture of oxo compounds

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5086067A (en) * 1989-12-18 1992-02-04 G. D. Searle & Co. Ltb4 synthesis inhibitors
US5217981A (en) * 1989-12-18 1993-06-08 G. D. Searle & Co. LTB4 synthesis inhibitors
US5112864A (en) * 1991-05-30 1992-05-12 G. D. Searle & Co. PLA2 inhibitors as antiinflammatories
US5356919A (en) * 1991-05-30 1994-10-18 G. D. Searle & Co. Leukotriene B4 synthesis inhibitors
US5508309A (en) * 1991-05-30 1996-04-16 G. D. Searle & Co. LTB4 synthesis inhibitors
US5591756A (en) * 1991-05-30 1997-01-07 G. D. Searle & Co. LTB4 synthesis inhibitors
WO2016059152A1 (en) * 2014-10-16 2016-04-21 Dsm Ip Assets B.V. Method for producing specific alpha, beta-unsaturated aldehydes
US10029970B2 (en) 2014-10-16 2018-07-24 Dsm Ip Assets B.V. Method for producing specific α, β-unsaturated aldehydes

Also Published As

Publication number Publication date
JPS50148306A (en) 1975-11-27
DE2518031C2 (en) 1987-10-22
ATA321375A (en) 1977-02-15
FR2268775A1 (en) 1975-11-21
AT339270B (en) 1977-10-10
NL7504943A (en) 1975-10-28
CH612169A5 (en) 1979-07-13
FR2268775B1 (en) 1978-06-30
NL163497B (en) 1980-04-15
DE2518031A1 (en) 1975-11-13
JPS548651B2 (en) 1979-04-17
NL163497C (en) 1980-09-15

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee