Method for the synthesis of omega-amino-alkanoic acids
AssigneeArkema France
InventorJean-Luc Dubois
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AssigneeArkema France
InventorJean-Luc Dubois
Estimating the term…
The invention relates to a method for the synthesis of amino acids/esters of general formula NH2—(CH2)n—COOR in which n is an integer between 5 and 14, and R is either H or an alkyl radical including from 1 to 4 carbon atoms, from natural long-chain mono-unsaturated fatty acids or esters including at least 10 adjacent carbon atoms per molecule, said method comprising: first converting, if necessary, said natural long-chain fatty acid or ester into a monounsaturated fatty acid/ester of general formula R1—(CH2)m—CH═CH—(CH2)p—COOR in which R1 is H, CH3 or a COOR radical, m is an integer between 0 and 14 and p is an integer between 2 and 11, then submitting the latter to a crossed catalytic metathesis reaction with a compound of formula R2—CH═CH—R3 in which R2 is either H or CN and R3 is CN or CH2NH2, provided that if R2 is CN, R3 can be only CN, and finally converting the resulting product of the general formula R3—CH═CH—(CH2)p—COOR into an amino-acid, either by hydrogenation, or by hydrogenation of the triple terminal bond, or by amination of the double terminal bond.
1) A process for synthesizing amino acids or amino esters of general formula NH2—(CH2)n—COOR in which n represents an integer between 5 and 14, and R is either H or an alkyl radical containing from 1 to 4 carbon atoms, from monounsaturated long-chain natural fatty acids or esters containing at least 10 adjacent carbon atoms per molecule, which consists first in converting, in an optional first step, said long-chain natural fatty acid or ester, via a physical treatment, via homometathesis or via a microbiological fermentation process, into a monounsaturated fatty acid or ester of general formula R1—(CH2)m—CH═CH—(CH2)p—COOR in which R1 represents H, CH3 or a radical COOR, m is an integer between 0 and 14 and p is an integer between 2 and 11, and then in subjecting said monounsaturated fatty acid or ester of general formula R1—(CH3)m—CH═CH—(CH2)p—COOR to a catalytic cross-metathesis reaction with a compound of formula R2—CH═CH—R3 in which R2 is either H or CN and R3 is H, CN or CH2NH2, with the proviso that if R2 is CN, R3 can be only CN, and then finally in converting into an ω-amino acid the resulting product corresponding to the general formula R3—CH═CH—(CH2)p—COOR, either by hydrogenation of the terminal triple bond, or by amination of the terminal double bond.
12) An amino acid or amino ester of renewable origin of general formula NH2—(CH2)—COOR in which n represents an integer between 5 and 14, and R is either H or an alkyl radical containing from 1 to 4 carbon atoms.
Dependencies are inferred from the claim text.