GB1105293A – Process for the production of alkyl vinyl ethers
– Google Patents
GB1105293A – Process for the production of alkyl vinyl ethers
– Google Patents
Process for the production of alkyl vinyl ethers
Info
Publication number
GB1105293A
GB1105293A
GB25672/65A
GB2567265A
GB1105293A
GB 1105293 A
GB1105293 A
GB 1105293A
GB 25672/65 A
GB25672/65 A
GB 25672/65A
GB 2567265 A
GB2567265 A
GB 2567265A
GB 1105293 A
GB1105293 A
GB 1105293A
Authority
GB
United Kingdom
Prior art keywords
concentration
acetate
stage
acetic acid
weight
Prior art date
1965-06-17
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
GB25672/65A
Inventor
Duncan CLARK
Percy Hayden
John Charlton
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.)
1965-06-17
Filing date
1965-06-17
Publication date
1968-03-06
1965-06-17
Application filed by Imperial Chemical Industries Ltd
filed
Critical
Imperial Chemical Industries Ltd
1965-06-17
Priority to GB25672/65A
priority
Critical
patent/GB1105293A/en
1966-06-02
Priority to US554652A
priority
patent/US3515758A/en
1966-06-08
Priority to NL6607927A
priority
patent/NL6607927A/xx
1966-06-16
Priority to DE19661568847
priority
patent/DE1568847A1/en
1966-06-17
Priority to ES0328053A
priority
patent/ES328053A1/en
1966-06-17
Priority to FR65904A
priority
patent/FR1483617A/en
1966-06-17
Priority to BE682738D
priority
patent/BE682738A/xx
1968-03-06
Publication of GB1105293A
publication
Critical
patent/GB1105293A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C67/00—Preparation of carboxylic acid esters
C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
C07C67/05—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation
C07C67/055—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds with oxidation in the presence of platinum group metals or their compounds
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
C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Abstract
Alkyl vinyl ethers are prepared by a process consisting of a first stage (Stage I) comprising contacting ethylene with a salt or co-ordination compound of palladium, in the presence of less than 5% by weight of the reaction medium of water and in the presence of acetate ions, molecular oxygen, a copper salt, acetic acid and 1,1-diacetoxyethane or 1,2-diacetoxyethane (the concentration of acetic acid in the process not exceeding 30% by weight of the reaction medium), separating a mixture comprising vinyl acetate, acetic acid and water, removing from said mixture at least some of the water by phase separation, and a second stage (Stage II) comprising contacting the remainder of the said separated mixture, containing vinyl acetate and acetic acid, with an aliphatic alcohol in the presence of a salt or co-ordination compound of palladium. Preferably in Stage I the concentration of acetic acid does not exceed 10% by weight of the reaction medium; the concentration of water does not exceed 1% by weight of the reaction medium; palladous chloride, palladous bromide or palladous acetate are used as the palladium salt, or lithium chloropalladite, sodium chloropalladite, or bis-(benzonitrile)-dichloropalladium II as the co-ordination compound in concentrations between 10-4 and 10-3 molar; halide ions may be present, in the form of an alkali metal chloride in concentrations up to 100 moles per mole of palladium compound, but in any case so that the total halide concentration does not exceed 0.2 molar; up to 1 mole (per litre of the reaction mixture) of nitrate, nitrite, nitrosyl, nitro or nitroso compound may be added, especially in the form of an alkali metal nitrate or nitric acid; acetate ions are provided by 0.1 to 0.5 moles of alkali metal or alkaline earth acetate per litre; the copper salt is copper acetate in concentrations between 0.05 and 0.3 molar; the reaction temperature is between 50 DEG C. and 180 DEG C.; ethylene and molecular oxygen are introduced as a gaseous mixture containing 3 to 10% of the latter; and an overall operating pressure of 20-34 atmospheres is maintained. The phase separation is suitably carried out at temperatures between 20 DEG C. and 50 DEG C. Preferably in stage II, the palladium compounds are as indicated in stage I in a similar concentration range; halide ions may be present in the form of an alkali metal bromide in concentrations up to 100 molar per mole of palladium compound, but in any case so that the total halide concentration does not exceed 0.2 molar; the redox system is present in the form of a copper salt, e.g. copper bromide; the reaction temperature is in the range -50 DEG C. to 200 DEG C.; the vinyl acetate and acetic acid mixture is introduced continuously; the aliphatic alcohols contain 1 to 6 carbon atoms, e.g. methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol; the vinyl acetate is present in excess; an inert solvent is present; a base is present, e.g. lithium acetate, at 0.1 to 2 times the molar concentration of the palladium compound; the concentration of the acetal, derived from the alcohol used in the process, is kept stationary at a level of up to 10% by weight of the reaction mixture, or up to 5% by weight, with up to 5% of water; the concentration of acetic acid is kept stationary at a level of up to 50% by weight of the reaction medium; the operating pressure is maintained between 0.1 and 1 atmosphere.
GB25672/65A
1965-06-17
1965-06-17
Process for the production of alkyl vinyl ethers
Expired
GB1105293A
(en)
Priority Applications (7)
Application Number
Priority Date
Filing Date
Title
GB25672/65A
GB1105293A
(en)
1965-06-17
1965-06-17
Process for the production of alkyl vinyl ethers
US554652A
US3515758A
(en)
1965-06-17
1966-06-02
Process for the production of ethylene compounds
NL6607927A
NL6607927A
(en)
1965-06-17
1966-06-08
DE19661568847
DE1568847A1
(en)
1965-06-17
1966-06-16
Process for the production of ethylene compounds
ES0328053A
ES328053A1
(en)
1965-06-17
1966-06-17
Procedure for the preparation of eteres vinyl car hire (Machine-translation by Google Translate, not legally binding)
FR65904A
FR1483617A
(en)
1965-06-17
1966-06-17
Manufacturing process of vinyl ethers
BE682738D
BE682738A
(en)
1965-06-17
1966-06-17
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
GB25672/65A
GB1105293A
(en)
1965-06-17
1965-06-17
Process for the production of alkyl vinyl ethers
Publications (1)
Publication Number
Publication Date
GB1105293A
true
GB1105293A
(en)
1968-03-06
Family
ID=10231466
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB25672/65A
Expired
GB1105293A
(en)
1965-06-17
1965-06-17
Process for the production of alkyl vinyl ethers
Country Status (6)
Country
Link
US
(1)
US3515758A
(en)
BE
(1)
BE682738A
(en)
DE
(1)
DE1568847A1
(en)
ES
(1)
ES328053A1
(en)
GB
(1)
GB1105293A
(en)
NL
(1)
NL6607927A
(en)
Family Cites Families (13)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
GB964001A
(en)
*
1960-09-28
1964-07-15
Ici Ltd
Improvements in and relating to the production of unsaturated esters
NL289217A
(en)
*
1962-02-22
GB952718A
(en)
*
1962-02-26
1964-03-18
Nippon Synthetic Chem Ind
Process for producing acetaldehyde
US3221045A
(en)
*
1962-03-26
1965-11-30
Union Carbide Corp
Preparation of olefinic esters
US3210152A
(en)
*
1962-05-25
1965-10-05
Shell Oil Co
Regeneration of metal-containing reaction components and process for the production of palladium chloride
NL294964A
(en)
*
1962-07-06
GB975709A
(en)
*
1962-07-25
1964-11-18
Ici Ltd
Improvements in and relating to the production of carboxylic acid esters of unsaturated monohydric alcohols
NL299889A
(en)
*
1962-10-29
US3277158A
(en)
*
1963-06-11
1966-10-04
Union Oil Co
Production of vinyl acetate from ethylene
US3285970A
(en)
*
1963-06-18
1966-11-15
Union Oil Co
Synthesis of acetals
US3277159A
(en)
*
1963-06-18
1966-10-04
Union Oil Company Of America
Process for the production of unsaturated esters and acetals from olefins
DE1249856B
(en)
*
1963-10-14
1967-09-14
Imperial Chemical Industries Limited I ondon
Process for the preparation of alkyl alkenyl ethers
US3306930A
(en)
*
1964-08-17
1967-02-28
Du Pont
Cyclic method of preparing vinyl acetate
1965
1965-06-17
GB
GB25672/65A
patent/GB1105293A/en
not_active
Expired
1966
1966-06-02
US
US554652A
patent/US3515758A/en
not_active
Expired – Lifetime
1966-06-08
NL
NL6607927A
patent/NL6607927A/xx
unknown
1966-06-16
DE
DE19661568847
patent/DE1568847A1/en
active
Pending
1966-06-17
ES
ES0328053A
patent/ES328053A1/en
not_active
Expired
1966-06-17
BE
BE682738D
patent/BE682738A/xx
unknown
Also Published As
Publication number
Publication date
DE1568847A1
(en)
1970-04-02
BE682738A
(en)
1966-12-19
ES328053A1
(en)
1967-08-01
NL6607927A
(en)
1966-12-19
US3515758A
(en)
1970-06-02
Similar Documents
Publication
Publication Date
Title
Pritchard et al.
1956
Kinetics and mechanism of the acid-catalyzed hydrolysis of substituted ethylene oxides1
Garrett
1957
The kinetics of solvolysis of acyl esters of salicyclic acid
US3393136A
(en)
1968-07-16
Preparation of oxalates
US4229591A
(en)
1980-10-21
Process for preparing a diester of oxalic acid in the gaseous phase
McKeon et al.
1972
The palladium (II) catalyzed vinyl interchange reaction—II
Lorette et al.
1959
Use of acetone dimethyl acetal in preparation of methyl esters
US3387043A
(en)
1968-06-04
Homologation process
US3045051A
(en)
1962-07-17
Production of dialkyl sulfoxides
Ogata et al.
1962
Kinetics of the sodium alkoxide reduction of nitrobenzenes
GB1105293A
(en)
1968-03-06
Process for the production of alkyl vinyl ethers
Barusch et al.
1951
Identification of β-dicarbonyl compounds
Jones et al.
1954
Conductances of Some Salts and Ion-Pair Equilibria in Acetic Acid at 30° 1, 2
GB1378446A
(en)
1974-12-27
Process for the manufacture of dicyanovinyl compounds
ES316221A1
(en)
1965-11-16
Procedure for the obtaining of aliphatic alcohols. (Machine-translation by Google Translate, not legally binding)
GB808108A
(en)
1959-01-28
Production of polyvinyl alcohol
US3381037A
(en)
1968-04-30
Process for producing acetaldehyde
GB1047408A
(en)
1966-11-02
GB1405714A
(en)
1975-09-10
Purification of hydrogen chloride
Schmid et al.
1965
Structural Determinations by Nuclear Magnetic Resonance. 3-Substituted Propionyl Chlorides
US3053621A
(en)
1962-09-11
Production of stannous halide
GB1041376A
(en)
1966-09-07
Production of glyoxal
KR840006962A
(en)
1984-12-04
Method for producing diester of oxalic acid
US3641162A
(en)
1972-02-08
Production of ethers
USRE31245E
(en)
1983-05-17
Process for preparing a diester of oxalic acid in the gaseous phase
GB1086347A
(en)
1967-10-11
Production of acetaldehyde
None