Method of synthesising amino acid by metathesis, hydrolysis, then hydrogenation
AssigneeArkema France
InventorsJean-Luc Dubois, Jean-Luc Couturier
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Abstract
A method of synthesising an amino acid from an unsaturated fatty compound I that includes at least the following steps: cross-metathesis with a short unsaturated compound II, one of compounds I or II comprising a nitrile function and the other of these compounds II or I an ester function, so as to obtain and recover at least one monounsaturated nitrile ester NEU; hydrolysis of the NEU in unsaturated acid nitrile NAU; hydrogenation of the NAU to saturated amino acid AA; and then purification of the AA, if applicable, in particular by crystallisation. Also, a polymer obtained by polymerisation using the amino acid synthesised according to the method.
Claims17
A process for synthesizing an amino acid from an unsaturated fatty compound I of formula:
- R1—CH═CH—[(CH2)q—CH═CH]p—(CH2)n—R2 in which:
- R1 is H, an alkyl radical of 1 to 11 carbon atoms, optionally comprising a hydroxyl function, or (CH2)m—R4
- m is an integer in the range from 0 to 11,
- n is an integer in the range from 2 to 13,
- p is an integer, p being equal to 0, 1 or 2,
- q is an integer equal to 0 or 1,
- R2 is COOR5 or CN,
- R4 is H or R2
- R5 is an alkyl radical of 1 to 11 carbon atoms or a radical comprising two or three carbon atoms bearing one or two hydroxyl functions, or alternatively a diglyceride or a triglyceride residue in which each fatty acid of said glyceride residue is either saturated or unsaturated,
- wherein the process comprises at least the following steps:
- cross metathesis with a unsaturated compound II, the unsaturated compound II having a main chain comprising less than 8 carbons, one of the compounds I or II comprising a nitrile function and the other of these compounds II or I an ester function, so as to obtain and recover at least one monounsaturated nitrile ester UNE;
- hydrolysis of the UNE into an unsaturated acid nitrile UAN;
- hydrogenation of the UAN into a saturated AA;
- and
- optional purification of the AA.
Dependencies are inferred from the claim text.