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US3720710A Expired / Lapsed US ⏱️ 0.0 years remaining

Carbonyl compounds from allene and its derivatives

Assignee: Marathon Oil Co
•
Filing: 1968-11-01
•
Granted: 1973-03-13
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Expires: 1988-11-01
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Abstract

Abstract Organic carbonyl compounds containing at least five carbon atoms are prepared by reacting an organic carbonyl compound having at least one hydrogen alpha to the carbonyl group with an acyclic organic compound containing at least two adjacent carbon to carbon double bonds at a temperature of from - 50* to 200* C for a period of from 0.1 to about 100 hours in the presence of a free radical initiator. A mixture of monomeric and polymeric carbonyl products are formed. Selectivity to any particular weight product is monitored by selection of the mole ratio of reactants. As a specific example, reaction of allene with excess acetic acid forms a product mixture comprising pimelic acid, allyl acetic acid and a resin acid of average gram molecular weight between about 200 and about 2,000. These synthetic resin acids may be used as substitutes for naturally occurring organic acids or may be used to control the molecular weight or cross linking in polyesters.

Inventors

  • 👤 C Norton
  • 👤 E Hurley

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 11:56
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C07; C07C; C07C55/00; C07C55/02; C07C55/14; C07C55/16; C07C57/00; C07C57/02; C07C57/03; C08G63/00; C08G63/02; C08G63/12; C08G63/46; C08G63/48

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 81 words
A process for the preparation of resin acids having average molecular weights of from about 200 to about 2,000, said process comprising reacting allene with an organic carbonyl compound having at least 1 hydrogen alpha to the carbonyl group and selected from the class consisting of acid anhydrides, acid halides, carboxylic acids, and esters in the presence of a free radical initiator, wherein from about 2 to about 8 moles of allene are reacted for each mole of said carbonyl group.
Claim 2
Dependent Claim 81 words
A process for the preparation of resin acids having average molecular weights of from about 200 to about 2,000, said process comprising reacting allene with an organic carbonyl compound having at least 1 hydrogen alpha to the carbonyl group and selected from the class consisting of acid anhydrides, acid halides, carboxylic acids, and esters in the presence of a free radical initiator, wherein from about 2 to about 8 moles of allene are reacted for each mole of said carbonyl group.
Claim 3
Dependent Claim 68 words
A process according to claim 1 wherein the organic carbonyl compound is selected from the group consisting of acetic anhydride, propionic anhydride, glutaconic anhydride, acetyl chloride, butyryl bromide, crotonic acid, benzylic acid, malonic acid, succinic acid, maleic acid, adipic acid, dodecanedioic acid, malonaldehydric acid, pyruvic acid, methyl acetate, n-amyl acetate, isoamyl n-butyrate, phenyl acetate, vinyl acetate, and carboxylic acids having from 2 to 5 carbon atoms per molecule.
Claim 4
Dependent Claim 12 words
The process of claim 2 wherein the carboxylic acid comprises acetic acid.
Claim 5
Dependent Claim 101 words
A process for the preparation of resin acids having average molecular weights of from about 200 to about 2,000, said process comprising reacting a lower alkanoic acid with allene or mono-lower allyl substituted allene at a temperature of about -50* to 200*C. in the presence of a free radical initiator compound for a period of from 0.1 to about 100 hours in the presence of from 0.01 to 10 mole percent radical initiator based on allene, wherein from about 2 to about 8 moles of allene or said mono-lower allyl substituted allene are reacted for each mole of said carbonyl group.
Claim 6
Dependent Claim 101 words
A process for the preparation of resin acids having average molecular weights of from about 200 to about 2,000, said process comprising reacting a lower alkanoic acid with allene or mono-lower allyl substituted allene at a temperature of about -50* to 200*C. in the presence of a free radical initiator compound for a period of from 0.1 to about 100 hours in the presence of from 0.01 to 10 mole percent radical initiator based on allene, wherein from about 2 to about 8 moles of allene or said mono-lower allyl substituted allene are reacted for each mole of said carbonyl group.

References Cited (Backward Citations)

US3600420A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1976-03-12 1976-09-11 1977-03-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1980-03-12 1980-09-11 1981-03-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1984-03-12 1984-09-11 1985-03-13 $7700.00 Window Closed / Lapsed

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