GB1105956A - Process for the production of vinyl ethers - Google Patents

Process for the production of vinyl ethers

Info

Publication number
GB1105956A
GB1105956A GB47173/64A GB4717364A GB1105956A GB 1105956 A GB1105956 A GB 1105956A GB 47173/64 A GB47173/64 A GB 47173/64A GB 4717364 A GB4717364 A GB 4717364A GB 1105956 A GB1105956 A GB 1105956A
Authority
GB
United Kingdom
Prior art keywords
vinyl ether
ether
acetal
hydroxy compound
methyl
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
GB47173/64A
Inventor
Duncan CLARK
Percy Hayden
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB47173/64A priority Critical patent/GB1105956A/en
Priority to NL6514991A priority patent/NL6514991A/xx
Priority to FR39068A priority patent/FR1465520A/en
Priority to DEJ29414A priority patent/DE1275532B/en
Priority to US3637867D priority patent/US3637867A/en
Publication of GB1105956A publication Critical patent/GB1105956A/en
Priority to FR7020143A priority patent/FR2049783A5/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D19/00—Degasification of liquids
    • B01D19/02—Foam dispersion or prevention
    • B01D19/04—Foam dispersion or prevention by addition of chemical substances
    • B01D19/0404—Foam dispersion or prevention by addition of chemical substances characterised by the nature of the chemical substance
    • 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
    • B01J27/08—Halides
    • 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
    • B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate ligands
    • 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
    • B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
    • B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
    • B01J31/30—Halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/14—Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
    • 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
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening 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
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • 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
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A second vinyl ether is made from a first vinyl ether by transetherification, by contacting the said first ether with an organic hydroxy compound under substantially anhydrous conditions (defined as up to 10% water present) in the presence of a salt or co-ordination compound of Ru, Rh, Pd, Os, Ir or Pt, whereby the second vinyl ether is formed, comprising a vinyl moiety from the starting vinyl ether, and an organic moeity from the organic hydroxy compound. The starting vinyl ether may be of formula <FORM:1105956/C2/1> wherein R1, R2 and R3 represent aliphatic, cycloaliphatic, aryl or heterocyclic groups, or wherein any two of R1, R2 and R3 form part of a cyclic group as defined above, and R6 represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aralkyl or heterocyclic group. Methyl vinyl ether and isobutyl vinyl ether are specified. The organic hydroxy compound may carry further substituent groups, e.g. ketone, ether, ester, hydroxy, halogen or amino. Examples include C1- 20 alkanols (many named), phenols, cresols, xylenols, rescorcinol and hydroquinone. Particular catalysts are palladous chloride, bromide or acetate, lithium chloropalladite or bromopalladite, and dichloro-bis-(benzonitrile)-palladium (II). The complexes among these may be prepared in situ by conducting the transetherification in a solvent which can complex with the simple salts, e.g. sulphoxides, sulphones, benzonitrile or diethylene glycol dimethyl ether. Suitably reaction proceeds at -50 DEG to +200 DEG C. at 0.1-1.0 At., with a catalyst concentration up to 1 M. Additionally, there may be present as complexing agent an alkali metal halide (not the fluoride), e.g. lithium chloride. To suppress acetal formation, a stationary content of up to 20 wt. per cent of an acetal may be incorporated. In examples, isobutyl methyl acetal, diisobutyl acetal, and acetaldehyde appear as by-products in the reaction of methyl vinyl ether with isobutanol. The product may be recovered by distillation, crystallization or countercurrent solvent extraction.
GB47173/64A 1964-11-19 1964-11-19 Process for the production of vinyl ethers Expired GB1105956A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB47173/64A GB1105956A (en) 1964-11-19 1964-11-19 Process for the production of vinyl ethers
NL6514991A NL6514991A (en) 1964-11-19 1965-11-18
FR39068A FR1465520A (en) 1964-11-19 1965-11-19 Process for the production of ethylenic compounds from vinyl ethers
DEJ29414A DE1275532B (en) 1964-11-19 1965-11-19 Process for the production of a vinyl ether
US3637867D US3637867A (en) 1964-11-19 1968-03-07 Process for the production of ethylenic compounds
FR7020143A FR2049783A5 (en) 1964-11-19 1970-06-02 Non-ionic biodegradable anti-foam additives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB47173/64A GB1105956A (en) 1964-11-19 1964-11-19 Process for the production of vinyl ethers

Publications (1)

Publication Number Publication Date
GB1105956A true GB1105956A (en) 1968-03-13

Family

ID=10444011

Family Applications (1)

Application Number Title Priority Date Filing Date
GB47173/64A Expired GB1105956A (en) 1964-11-19 1964-11-19 Process for the production of vinyl ethers

Country Status (4)

Country Link
DE (1) DE1275532B (en)
FR (1) FR2049783A5 (en)
GB (1) GB1105956A (en)
NL (1) NL6514991A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012105879A1 (en) 2012-07-02 2014-01-02 Oxea Gmbh Process for the preparation of isononyl derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950420A (en) * 1988-08-31 1990-08-21 Nalco Chemical Company Antifoam/defoamer composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2579412A (en) * 1950-03-02 1951-12-18 Du Pont Reaction of vinyl ethers with hydroxy compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102012105879A1 (en) 2012-07-02 2014-01-02 Oxea Gmbh Process for the preparation of isononyl derivatives
WO2014005854A1 (en) 2012-07-02 2014-01-09 Oxea Gmbh Method for the production of isononyl derivatives

Also Published As

Publication number Publication date
DE1275532B (en) 1968-08-22
FR2049783A5 (en) 1971-03-26
NL6514991A (en) 1966-05-20

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