Method for the synthesis of diacids or diesters from natural fatty acids and/or esters
AssigneeArkema France
InventorJean-Luc Dubois
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AssigneeArkema France
InventorJean-Luc Dubois
Estimating the term…
The invention relates to a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x—COOR, in which n is an integer between 5 and 14, R is either H or an alkyl radical of 1 to 4 carbon atoms, from natural long-chain monounsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule of the general formula CH3—(CH2)n—CHR1—CH2—CH═CH—(CH2)p—COOR, in which R is H or an alkyl radical with 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are equal or different and are indices between 2 and 11. The method comprises: during a first step, converting the natural fatty acid or ester by pyrolysis or by ethenolysis, into a 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, depending on the nature of the processed fatty acid/ester and the conversion used; during a second step, submitting the product thus obtained to a metathesis or homometathesis reaction for obtaining a compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)m—COOR, or cross-metathesis with a compound of formula R2OOC—(CH2)r—CH═CH—R3, in which R2 is either H or an alkyl radical front with 1 to 4 carbon atoms, r is either 0 or 1 or 2 and R3 is H, CH3 or COOR2, thus defining a cyclic or molecule or not, in order to obtain an unsaturated compound of the general formula ROOC—(CH2)m—CH═CH—(CH2)r—COOR2, and during a third step, converting the unsaturated compound into a saturated compound by hydrogenation of the double bond.
1) 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)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 3 and 11, which comprises:
8) A process for the synthesis of a diester of the formula C13OOC—(C2)8—COOCH3 starting from the methyl ester of ricinoleic acid comprising
9) A process for the synthesis of the diester of the formula CH3OOC—(CH2)12—COOCH3 starting from the methyl ester of lesquerolic acid comprising
10) 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 thin 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 and, thereafter hydrogenation.
11) A process for the synthesis of a diacid or diester of formula ROOC—(CH2)8—COOR starting from 5-lauroleic or 5-physeteric acid or ester comprising
Dependencies are inferred from the claim text.