Method for the synthesis of diacids or diesters from natural fatty acids and/or esters
AssigneeArkema France
InventorJean-Luc Dubois
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Abstract
Disclosed herein a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x-COOR, in which n represents an integer between 5 and 14 and R is either H or an alkyl radical of 1 to 4 carbon atoms, starting from long-chain natural monounsaturated fatty acids or esters comprising at least 10 adjacent carbon atoms per molecule, of formula CH3—(CH2)n-CHR1—CH2—CH═CH—(CH2)p-COOR, in which R represents H or an alkyl radical comprising from 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are identical or different, are indices between 2 and 11.
Claims8
A process for the synthesis of diacids or diesters of the general formula ROOC—(CH2)x—COOR, in which x represents an integer between 5 and 24 and R is either H or an alkyl radical of 1 to 4 carbon atoms, starting from long-chain natural monounsaturated fatty acids or esters comprising at least 10 adjacent carbon atoms per molecule, of the formula CH3—(CH2)nCHR1—CH2—CH═CH—(CH2)p—COOR, in which R represents H or an alkyl radical comprising from 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are identical or different, are indices between 3 and 11, which comprises:
- converting said natural monounsaturated fatty acid or ester, into an ω-monounsaturated fatty acid or ester of the general formula CH2═CH—(CH2)m—COOR, in which m is equal to p or p+1, then,
- subjecting the product thus obtained to cross-metathesis with a compound of the formula R2OOC—(CH2)r—CH═CH—R3, in which R2 is either H or an alkyl radical comprising from 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R3 is H, CH3 or COOR2, in the last case forming a cyclic or noncyclic molecule, to obtain an unsaturated compound of the formula ROOC—(CH2)m, —CH═CH—(CH2)r—COOR2, wherein the cross-metathesis is carried out in the presence of a second generation Grubbs catalyst, and then,
- converting, by hydrogenation, the unsaturated compound to a saturated compound.
A process for the synthesis of a diester of the formula CH3OOC—(CH2)8—COOCH3 starting from the methyl ester of ricinoleic acid comprising
- pyrolysis, to form an ester of the formula CH2═CH—(CH2)8—COOCH3, and subsequently cross-metathesis with methyl acrylate in the presence of a second generation Grubbs catalyst to form a diester of the formula CH3OOC—CH═CH—(CH2)8—COOCH3, which is subsequently hydrogenated.
A process for the synthesis of the diester of the formula CH3OOC—(CH2)12—COOCH3 starting from the methyl ester of lesquerolic acid comprising
- pyrolysis of the methyl ester of lesquerolic acid to form an ester of the formula CH2═CH—(CH2)10COOCH3, followed by cross-metathesis with methyl acrylate in the presence of a second generation Grubbs catalyst and thereafter hydrogenation.
A process for the synthesis of a diacid or diester of formula ROOC—(CH2)12—COOR starting from vaccenic acid or ester comprising ethenolysis of the acid or ester to give an unsaturated acid or ester of the formula CH2═CH—(CH2)9—COOR, followed by cross-metathesis with an acid or ester of the formula CH3—CH═CH—CH2—COOR in the presence of a second generation Grubbs catalyst and, thereafter hydrogenation.
Dependencies are inferred from the claim text.