Fatty oil ex helianthus annuus for the production of diperazelaic acid
AssigneeHenkel Kommanditgesellschaft auf Aktien
InventorsHorst Eierdanz, Paul Schulz, Beatrix Kottwitz
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Abstract
The use of a fatty oil ex Helianthus annuus containing 78 to 92% by weight oleic acid and 2 to 10% by weight linoleic acid for the production of diperazelaic acid, with elimination of enrichment steps with respect to the oleic acid content, by fat splitting, distillation, oxidative ozonolysis of the fatty acid mixture obtained, and reaction of the azelaic acid thus obtained with hydrogen peroxide to form diperazelaic acid. The resulting diperazelaic acid has improved stability in storage and is obtained in high yields and in highly pure form.
Claims14
A process for the preparation of diperazelaic acid comprising the steps of:
- (A) reacting a fatty oil obtained from the seeds of Helianthus annuus and which contains from about 78 to about 92% by weight, based on the total weight of fatty acids present therein, of oleic acid, with water at a temperature in the range of from about 150.degree. to about 250.degree. C. to form a fatty acid phase and a glycerol/water phase, and separating the glycerol/water phase from the fatty acid phase,
- (B) distilling the fatty acid phase,
- (C) reacting the distilled fatty acid with an ozone/air mixture in the presence of water at a temperature in the range of from about 20.degree. to about 40.degree. C., to form azelaic acid, and
- (D) contacting the azelaic acid with concentrated sulfuric acid and hydrogen peroxide to form diperazelaic acid.
A process for the preparation of diperazelaic acid comprising the steps of
- (A) reacting a fatty oil obtained from the seeds of Helianthus annuus and which contains from about 78 to about 92% by weight, based on the total weight of fatty acids present therein, of oleic acid, without prior enrichment of the oleic acid content, with water at a temperature in the range of from about 185.degree. to about 215.degree. C., and under a pressure of from about 20 to about 35 bar to form a fatty acid phase and a glycerol/water phase, and separating the glycerol/water phase from the fatty acid phase,
- (B) distilling the fatty acid phase under reduced pressure,
- (C) reacting the distilled fatty acid with an ozone/air mixture in the presence of water at a temperature in the range of from about 20.degree. to about 40.degree. C., to form a reaction mixture which separates into an aqueous phase and an organic phase,
- (D) separating the organic phase from the aqueous phase,
- (E) air oxidizing the organic phase at a temperature of from about 60.degree. C. to about 100.degree. C.,
- (F) treating the organic phase with hydrogen peroxide at a temperature of from about 80.degree. C. to about 95.degree. C.,
- (G) heating the organic phase to a temperature of from about 120.degree. to about 140.degree. C. to thermally degrade the hydrogen peroxide,
- (H) contacting the organic phase with concentrated sulfuric acid followed by hydrogen peroxide at a temperature in the range of from about 20.degree. to about 25.degree. C. to form a reaction mixture containing diperazelaic acid, and
- (I) isolating the diperazelaic acid from the reaction mixture.
Dependencies are inferred from the claim text.