GB1481577A - Process for the manufacture of oxo compounds and silyl vanadates as catalysts therefor - Google Patents

Process for the manufacture of oxo compounds and silyl vanadates as catalysts therefor

Info

Publication number
GB1481577A
GB1481577A GB8445/75A GB844575A GB1481577A GB 1481577 A GB1481577 A GB 1481577A GB 8445/75 A GB8445/75 A GB 8445/75A GB 844575 A GB844575 A GB 844575A GB 1481577 A GB1481577 A GB 1481577A
Authority
GB
United Kingdom
Prior art keywords
phenyl
yne
hydroxy
oxo compounds
silyl
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
GB8445/75A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1481577A publication Critical patent/GB1481577A/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 Table
    • C07F9/005—Compounds of elements of Group 5 of the Periodic Table 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • 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 Table
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1481577 Ethylenic oxo compounds F HOFFMANN-LA ROCHE & CO AG 28 Feb 1975 [1 March 1974] 8445/75 Heading C2C [Also in Division C3] Acetylenic alcohols are isomerized to ethylenic oxo compounds by contacting them with a silyl vanadate (Ph<SP>1</SP> 3 SiO) m (RO) 3-m V = O, wherein Ph<SP>1</SP> is a phenyl group having at least one electronwithdrawing substituent, R is a C 1-6 alkyl, a cycloalkyl, a phenyl, or a phenyl-C 1-6 -alkyl group or a group K 3 Si, wherein K is a C 1-6 alkyl, a cycloalkyl, a phenyl, or a phenyl-C 1-6 alkyl group, and m is 1, 2 or 3. Suitably 0.1-5 mol per cent of catalyst is used, at up to 150‹ C., preferably 40-110‹ C., optionally in a solvent. In Example 3 3-hydroxy-3 : 7-dimethyl-oct-6- en-l-yne is isomerized to citral at 95‹ C. over 8 hours in a paraffin oil i.p.o. In Example 4 the catalysts are used in the same isomerization. In Examples 3 and 5-12 the catalysts are used for the isomerization of: [3] 3 : 7- dihydroxy - 3 : 7 - dimethyl - oct - 1 - yne and [8] its 7 - methoxy derivative, [5,10 and 11] 3- methyl- or 3-phenyl or 1-propyl-3-hydroxybut-l-yne, [6 and 7] 3-hydroxy-3 : 7 : 11- trimethyl - dodeca - 6 : 10 - dien - 1 - yne and 3 - hydroxy - 3 : 7 : 11 : 15 - tetramethyl - hexadec - 1 - yne, [9] 1 - ethynyl - cyclohexanol, and [12] 4-ethynyl-4-hydroxy- 1 : 1-ethylenedioxy-3 : 5 : 5-trimethyl-cyclohex-2-ene.
GB8445/75A 1974-03-01 1975-02-28 Process for the manufacture of oxo compounds and silyl vanadates as catalysts therefor Expired GB1481577A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH293274A CH601156A5 (en) 1974-03-01 1974-03-01

Publications (1)

Publication Number Publication Date
GB1481577A true GB1481577A (en) 1977-08-03

Family

ID=4244866

Family Applications (1)

Application Number Title Priority Date Filing Date
GB8445/75A Expired GB1481577A (en) 1974-03-01 1975-02-28 Process for the manufacture of oxo compounds and silyl vanadates as catalysts therefor

Country Status (8)

Country Link
JP (1) JPS548649B2 (en)
AT (1) AT338226B (en)
BE (1) BE826112A (en)
CH (1) CH601156A5 (en)
DE (1) DE2508778A1 (en)
FR (1) FR2272971B1 (en)
GB (1) GB1481577A (en)
NL (1) NL163496C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4153615A (en) * 1978-03-27 1979-05-08 Hoffmann-La Roche Inc. Method of producing coloring agents

Also Published As

Publication number Publication date
JPS50117709A (en) 1975-09-16
AT338226B (en) 1977-08-10
FR2272971A1 (en) 1975-12-26
JPS548649B2 (en) 1979-04-17
DE2508778A1 (en) 1975-09-04
NL163496C (en) 1980-09-15
BE826112A (en) 1975-08-28
NL7500922A (en) 1975-09-03
FR2272971B1 (en) 1978-02-24
CH601156A5 (en) 1978-06-30
ATA158975A (en) 1976-12-15
NL163496B (en) 1980-04-15

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Legal Events

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