Monsanto Technology LLC

Straitmark Holding Ag

Sebastian Burck

Patrick Pierre Notte

Albert Devaux

Samuel Corentin Cogels

Cedric Nicolas Leclercq

Frederic Bruyneel

Patrick Notté

Frédéric Bruyneel

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&#x2014;O&#x2014;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&#x2014;O&#x2014;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.

Method for the synthesis of alpha-aminoalkylenephosphonic acid

A method for synthesis of N-phosphonoalkyliminodiacetic acid or derivatives thereof by forming a reaction mixture having an acid catalyst, a compound of the following general formula R&#x2014;CH&#x2014;NX&#x2014;CH&#x2014;Rand a compound having one or more P&#x2014;O&#x2014;P anhydride moieties to form a compound having a formula R&#x2014;CH&#x2014;N(&#x2014;CHPOR)(&#x2014;CH&#x2014;R) wherein in R&#x2014;CH&#x2014;NX&#x2014;CH&#x2014;R: X is &#x2014;CH&#x2014;OH or &#x2014;CH&#x2014;COOH; Rand Rare independently selected from the group consisting of nitrile, C-Calkyl carboxylate, and carboxylic acid for when X is &#x2014;CH&#x2014;OH, or Rand Rare both carbonyl groups linked by a hydrogen substituted nitrogen atom or a C-C-alkyl substituted nitrogen atom; and Ris H, an alkyl group, or an aryl group; the anhydride moieties in the P&#x2014;O&#x2014;P anhydride compound have one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V); and 2) hydrolyzing the mixture to form N-phosphonomethyliminodiacetic acid or one of its derivatives.

Method for the synthesis of N-phosphonomethyliminodiacetic acid

A method for the synthesis of an aminoalkylenephosphonic acid or its phosphonate esters including the following steps: a) forming, in the presence of an aldehyde or ketone and an acid catalyst, a reaction mixture by mixing a compound having at least one HNRRmoiety or a salt thereof, with a compound having one or more P&#x2014;O&#x2014;P anhydride moieties, the moieties having one P atom at the oxidation state (+III) and one P atom at the oxidation state (+III) or (+V), wherein the ratio of moles of aldehyde or ketone to N&#x2014;H moieties is 1 or more and wherein the ratio of N&#x2014;H moieties to P&#x2014;O&#x2014;P anhydride moieties is 0.3 or more, and b) recovering the resulting aminoalkylenephosphonic acid having compound or its phosphonate esters.

Method for the synthesis of aminoalkylenephosphonic acid

A method for the synthesis of N-(phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters, or its phosphonate ester salts, which includes the steps of: a) forming, in the presence an acid catalyst, a reaction mixture having 2,5-diketopiperazine, formaldehyde and a compound including one or more P-0-P anhydride moieties, the moieties having one P atom at the oxidation state (+III) and the other P atom at the oxidation state (+III) or (+V), to form N,N'-bisphosphonomethyl-2,5-diketopiperazine, its mono- to tetra phosphonate esters, the dehydrated forms of N,N&#x2032;-bisphosphonomethyl-2,5-diketopiperazine and the phosphonate esters of its dehydrated forms; and b) hydrolyzing the N,N&#x2032;-bisphosphonomethyl-2,5-diketopiperazine, its dehydrated forms or their phosphonate esters to obtain N-(phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts.

Method for the synthesis of N-(phosphonomethyl)glycine

A method for the synthesis of N-(phosphonomethyl) glycine or one of its derivatives selected from the group of its salts, its phosphonate esters and its phosphonate ester salts, including the steps of: a) forming a reaction mixture having an acid catalyst, N,N'-bis(carboxymethyl)-2,5-diketopiperazine and a compound having one or more P&#x2014;O&#x2014;P anhydride moieties, wherein the moieties have one P atom at the oxidation state (+III) and the other P atom at the oxidation state (+III) or (+V), to form N,N&#x2032;-bis(phosphonomethyl)-2,5-diketopiperazine, its dehydrated forms or their phosphonate esters; b) hydrolyzing the reaction mixture to form N-(phosphonomethyl)glycine or one of its derivatives selected from the group consisting of its salts, its phosphonate esters and its phosphonate ester salts.

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Louvain-la-Neuve, Belgium

Sebastian Burck