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US3609180A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing carboxylic acid esters of unsaturated alcohols

Assignee: Individual
•
Filing: 1966-08-22
•
Granted: 1971-09-28
•
Expires: 1986-08-22
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Abstract

Abstract A process for preparing the corresponding carboxylic acid esters of unsaturated alcohols by contacting olefins with aliphatic carboxylic acids in the presence of a gas selected from the group consisting of oxygen and oxygen-containing gases, using as catalyst a palladium salt and a copper salt, the improvement which comprises effecting the reaction in the presence of an organo-quaternary ammonium compound, said ammonium compound being one which does not have hydrogen directly linked to nitrogen and which can form under reaction conditions a carboxylic acidsoluble complex with said palladium salt.

Inventors

  • 👤 Hiroshi Shigematsu
  • 👤 Yasushi Shibahara

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 16:23
CPC Classifications
D; D04; D04B; D04B11/00; C; C07; C07C; C07C67/00; C07C67/04; C07C67/05; C07C67/055

Claims Analysis

Total Claims: 16
Claim 1
Independent Claim 15 words
The process of claim 1 wherein said organo-quaternary ammonium compound is said organo-quaternary ammonium halide.
Claim 2
Dependent Claim 18 words
The process according to claim 2 wherein the halogen ion of said organo-quaternary ammonium halide is chlorine ion.
Claim 3
Dependent Claim 15 words
The process of claim 1 wherein said organo-quaternary ammonium compound is said organo-quaternary ammonium hydroxide.
Claim 4
Dependent Claim 22 words
The process of claim 1 wherein said organo-quaternary ammonium compound is selected from the group consisting of betaine and said derivatives thereof.
Claim 5
Dependent Claim 23 words
The process of claim 1 wherein said organo-quaternary ammonium compound is selected from the group consisting of said amine-N-oxides and the hydrohalides thereof.
Claim 6
Dependent Claim 45 words
The process according to claim 6 wherein the hydrohalide of said amine oxide is an aqueous solution containing an amine oxide and a hydrohalide, said hydrohalide of amine oxide being formed in the reaction zone when said aqueous solution is added to the reaction system.
Claim 7
Dependent Claim 27 words
The process according to claim 1 wherein said lower alkanoic acid is an acid selected from the group consisting of acetic, propionic, butyric, valeric and caproic acids.
Claim 8
Dependent Claim 17 words
The process according to claim 1 wherein said carboxylic acid esters of unsaturated alcohols are vinyl acetate.
Claim 9
Dependent Claim 25 words
The process according to claim 1 wherein said palladium salt is a member selected from the group consisting of halides and aliphatic carboxylates of palladium.
Claim 10
Dependent Claim 24 words
The process according to claim 1 wherein said copper salt is a member selected from the group consisting of halides and carboxylates of copper.
Claim 11
Dependent Claim 29 words
The process according to claim 1 wherein said organo-quaternary ammonium compound is used in an amount of 0.001 to 1.0 mol per 1,000 cc. of the aliphatic carboxylic acid.
Claim 12
Dependent Claim 20 words
The process according to claim 1 wherein said reaction is effected at a temperature ranging between 50* and 140* C.
Claim 13
Dependent Claim 36 words
The process according to claim 1 wherein said reaction is effected in the presence of at least one member selected from the group consisting of alkali metal salts of aliphatic carboxylic acids and alkali metal halides.
Claim 14
Dependent Claim 22 words
The process according to claim 14 wherein the metal of said alkali metal salt is a member selected from lithium and sodium.
Claim 15
Dependent Claim 30 words
The process according to claim 14 wherein said alkali metal halide is used in an amount of not more than 1.0 mol per 1,000 cc. of said lower alkanoic acid.
Claim 16
Dependent Claim 31 words
The process according to claim 14 wherein said alkali metal carboxylate is used in an amount of not more than 6 mols per 1, 000 cc. of said lower alkanoic acid.

References Cited (Backward Citations)

BE615596A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1974-09-27 1975-03-29 1975-09-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1978-09-27 1979-03-29 1979-09-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1982-09-27 1983-03-29 1983-09-28 $7700.00 Window Closed / Lapsed

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