Method for the preparation of omega-amino-carboxylic acids and derivatives thereof
AssigneeVersalis S.P.A.
InventorsNicola Vecchini, Mirco Nodari, Armando Galeotti, Daniele Delledonne
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Abstract
A Method for the synthesis of ω-amino acids or derivatives thereof, includes the following steps synthesis of an ω-oxoester/linear acid by hydroformylation by CO/H2 mixture of at least one monounsaturated acid/ester, the monounsaturated acid/ester preferably resulting from a reaction of metathesis of oils/fats from renewable sources; synthesis of a linear ω-amino acid/ester and/or ω-aminoamide, subjecting the aforementioned ω-oxoester/linear acid to reductive amination; and possible synthesis of a linear ω-amino acid, subjecting the aforementioned linear ω-aminoester and/or ω-aminoamide to hydrolysis.
Claims21
A process for the preparation of an ω-aminocarboxylic acid or a derivative thereof of formula (III), starting from an ω-unsaturated carboxylic compound with the following formula (I):
- H2C═CR′-(Q)-COR″ (I)
- wherein R′ is H or an aliphatic hydrocarbon group, possibly substituted, with 1 to 10 carbon atoms;
- R″ is an OR or NR1R2 group, wherein R is selected from between H, ammonium, a monovalent M metal, a C1-C15 alkyl group and a C6-C15 aryl group;
- R1 and R2 are independently selected from between H, a C1-C15 alkyl group and a C6-C15 aryl group;
- Q is a divalent, aliphatic, optionally substituted hydrocarbon group with 1 to 12 carbon atoms,
- and, furthermore, said R′ and Q groups can be linked together to form an aliphatic carbocyclic structure with 5 to 7 carbon atoms;
- said process comprising the following stages in sequence:
- (A) making said compound of formula (I) react under the hydroformylation conditions with a mixture of hydrogen and carbon monoxide in the presence of a hydroformylation catalyst, based on rhodium (I) and phosphine binders and, optionally, a solvent, to obtain the corresponding ω-oxocarboxylic derivative with the following formula (II):
- HOC—CH2—CHR′-(Q)-COR″ (II)
- with R′, R″ and Q correspondingly having the meaning specified above,
- (B) subjecting said compound of formula (II) as obtained in step (A), in the absence of intermediate purification steps of the compound of formula (II) from the other reaction products, to reductive amination by reaction with hydrogen and ammonia in the presence of a catalyst to obtain the ω-aminocarboxylic derivative of formula (III):
- H2N—CH2—CH2—CHR′-(Q)-COR″ (III)
- and separating it from any reaction solvent;
- (C) optionally subjecting said compound of formula (III) to hydrolysis to obtain the corresponding ω-aminocarboxylic acid wherein R″ in formula (III) is OH.
Dependencies are inferred from the claim text.