Process for preparing caryophyllene oxide
AssigneeSymrise AG
InventorsMichael Backes, Nadine Heinemeier, Stefan Brennecke, Martin Heinemeier, Dietmar Schatkowski, Artur Dueck
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Abstract
The present invention relates to a method for oxidizing beta-caryophyllene with oxygen, in particular atmospheric oxygen, which avoids the use of catalysts, enzymes and solvents. Furthermore, the present invention provides a mixture comprising certain caryophyllene oxides as well as their use as a flavor and/or fragrance. The present invention also relates to products and semi-finished products comprising the mixture according to the invention.
Claims19
A method for oxidizing beta-caryophyllene comprising:
- (i) reacting 60 to 95 wt. % of beta-caryophyllene and 2 to 20 wt. % of alpha-humulene with oxygen at a temperature of 80 to 150° C. without a catalyst, without an enzyme, and without a solvent for 10 to 60 hours, and forming a reaction mixture comprising compounds (1), (2), and (3),
- wherein the reaction is carried out until a ratio of unreacted beta-caryophyllene to a sum of the compounds (1), (2), and (3) in the reaction mixture is 4:1 to 1:4 (unreacted beta-caryophyllene:sum of compounds (1), (2), and (3));
- (ii) after carrying out the reaction of (i) and reaching the ratio of 4:1 to 1:4, heating the reaction mixture to a temperature of 110 to 150° C. until the reaction mixture has a peroxide value of less than 30 meq O/kg;
- (iii) distilling the reaction mixture to obtain a fraction comprising the compounds (1), (2), and (3);
- and
- (iv) optionally, crystalizing the fraction comprising the compounds (1), (2), and (3).
A method for oxidizing beta-caryophyllene comprising:
- (i) reacting 60 to 95 wt. % of beta-caryophyllene and 2 to 20 wt. % of alpha-humulene with oxygen at a temperature of 80 to 150° C. without a catalyst, without an enzyme, and without a solvent for 10 to 60 hours, and forming a reaction mixture comprising compounds (1), (2), and (3),
- wherein the reaction is carried out until a ratio of unreacted beta-caryophyllene to a sum of the compounds (1), (2), and (3) in the reaction mixture is 4:1 to 1:4 (unreacted beta-caryophyllene:sum of compounds (1), (2), and (3));
- (ii) optionally, heating the reaction mixture to a temperature of 110 to 150° C.;
- (iii) adding a co-solvent to the reaction mixture and then distilling the reaction mixture with the added co-solvent to obtain a fraction comprising the compounds (1), (2), and (3),
- wherein the co-solvent is polyethylene glycol and is added in a ratio of 3:1 to 1:1 (reaction mixture:polyethylene glycol);
- and
- (iv) optionally, crystalizing the fraction comprising the compounds (1), (2), and (3).
A method for oxidizing beta-caryophyllene comprising:
- (i) reacting 60 to 95 wt. % of beta-caryophyllene and 2 to 20 wt. % of alpha-humulene with oxygen at a temperature of 80 to 150° C. without a catalyst, without an enzyme, and without a solvent for 10 to 60 hours, and forming a reaction mixture comprising compounds (1), (2), and (3),
- wherein the reaction is carried out until a ratio of unreacted beta-caryophyllene to a sum of the compounds (1), (2), and (3) in the reaction mixture is 4:1 to 1:4 (unreacted beta-caryophyllene:sum of compounds (1), (2), and (3));
- (ii) optionally, heating the reaction mixture to a temperature of 110 to 150° C.;
- (iii) distilling the reaction mixture to obtain a fraction comprising the compounds (1), (2), and (3),
- wherein the distilling comprises adding a co-solvent of polyethylene glycol to the reaction mixture, and distilling the reaction mixture with the co-solvent to obtain the fraction comprising the compounds (1), (2), and (3);
- and
- (iv) optionally, crystalizing the fraction comprising the compounds (1), (2), and (3).
Dependencies are inferred from the claim text.