Method for the synthesis of alpha-aminoalkylenephosphonic acid
AssigneeMonsanto Technology LLC
InventorsPatrick Notte, Samuel Cogels, Sebastian Burck
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Abstract
The present invention is related to a new method for the synthesis of alpha-aminoalkylenephosphonic acid or its phosphonate esters comprising the steps of forming a reaction mixture by mixing a P—O—P anhydride moiety comprising compound, having one P-atom at the oxidation state (+III) and the other P-atom at the oxidation state (+III) or (+V), an aminoalkanecarboxylic acid and an acid catalyst, wherein said reaction mixture comprises an equivalent ratio of alpha-aminoalkylene carboxylic acid to P—O—P anhydride moieties of at least 0.2, and recovering the resulting alpha-aminoalkylene phosphonic acid compound or an ester thereof from the reaction mixture.
Claims20
A method for the synthesis of an alpha-aminoalkylenephosphonic acid or an ester thereof, the method comprising the steps of:
- a) forming a reaction mixture by mixing an alpha-aminoalkylenecarboxylic acid, an acid catalyst, and a compound comprising one or more P—O—P anhydride moieties, wherein at least one of the P—O—P anhydride moieties comprises one P-atom at the oxidation state (+III) and the other P-atom at the oxidation state (+III) or (+V);
- and
- b) recovering the resulting alpha-aminoalkylenephosphonic acid or an ester thereof from said reaction mixture, wherein at least one carboxylic acid group in the alpha-aminoalkylenecarboxylic acid is replaced by a phosphonic acid group or an ester thereof, and wherein
- said alpha-aminoalkylenecarboxylic acid is selected from the group consisting of nitrilotriacetic acid, ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid, N-benzyliminodiacetic acid, N-methyliminodiacetic acid, iminodiacetic acid, N,N-bis(carboxymethyl)-1-glutamic acid, trisodium-N,N-bis(carboxymethyl)-alanine, N-cyanomethyl alanine, N,N-bis(cyanomethyl)-glycine, 4-morpholinoacetic acid, pyroglutamic acid, N-acetyl glycine, N,N-bis(carboxymethyl)-6-aminohexanoic acid, N-phenyl glycine, N-tosyl glycine, trans-1,2-cyclohexyldiaminotetraacetic acid monohydrate, N-phosphonomethyliminodiacetic acid, iminodiacetic acid grafted on resin, 1,4,7,10-tetraazadodecane-1,4,7,10-tetraacetic acid, N-phthaloglycine, and N′N′-dimethylglycine;
- and
- said P—O—P anhydride moiety comprising compound is selected from the group consisting of tetraphosphorus hexaoxide, P4O7, P4O8, P4O9, tetraethylpyrophosphite, and combinations thereof.
Dependencies are inferred from the claim text.