Process for producing N-phosphonomethylglycine derivatives

Claim 2

A process for producing water-soluble mono and di-N-Phosphonomethylglycine amine and iminourea salts from N-phosphonomethyliminodiacetic acid derivatives comprising oxidizing an aryl substituted iminourea salt of N-phosphonomethyliminodiacetic acid of the formula VI ##STR15## wherein Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, alkylphenyl and halophenyl to form a N-phosphonomethylglycine iminourea salt of the formula VII ##STR16## reacting said salt of formula VII with an amine, iminourea, diamine, or diiminourea having a molecular weight below 600 and a pKa above 10 in aqueous solution and separating the resulting water insoluble aryl iminourea from the resulting water soluble N-phosphonomethylglycine salt product.

Claim 3

A process according to claim 1 for producing N-phosphonomethylglycine derivatives of the formula I ##STR17## wherein (a) R 1 , R 2 and R 3 are independently selected from hydrogen and --R 4 and R 4 is a salt-forming cation iminourea derivative of the formula II ##STR18## wherein R 5 , R 5' , R 6 , R 6' and R 7 are independently H, NH 2 , CH 2 OH ##STR19## or an aryl, cycloalkyl or straight or branched chain alkyl or alkenyl group optionally supstituted by hydroxy or halogen, or an alkylaryl group provided that

Claim 4

at least one but no more than two of R 1 , R 2 or R 3 are R 4 , 2. no more than one R 5 , R 5' , R 6 , R 6' , are aryl or substituted aryl; and 3. no more than one of R 5 , R 5' , R 6 , R 6' , and R 7 is CH 2 OH; or (b) R 1 , R 2 and R 3 are independently selected from hydrogen and R 16 wherein R 16 is a salt-forming cation selected from the groups consisting of cations of organic ammonium selected from primary-, secondary- and tertiary-alkyl, none of these having more than two amine groups; and heterocyclic amines provided that no more than two of R 1 , R 2 and R 3 are --R 16 ; or (c) R 1 and R 2 are hydrogen and R 3 is R 17 wherein R 17 is a salt forming cation of the formula III ##STR20## wherein R is selected from the group consisting of C 2 -C 12 straight or branched chain alkylene radicals and R 8 and R 9 are each independently H or a C 1 -C 4 alkyl group; or (d) R 1 and R 2 are H and R 3 is a salt forming cation of the formula IV ##STR21## wherein Y is N, R 18 is a straight or branched chain alkylene radical having 1-12 carbon atoms and R 19 , R 11 , R 12 and R 10 are each independently H, alkyl, phenyl or allyl provided that only one of R 19 and R 10 may be alkyl, allyl or phenyl and only one of R 11 and R 12 may be alkyl, allyl or phenyl; said process comprising oxidizing an aryl substituted iminourea salt of N-phosphonomethyliminodiacetic acid of the formula VI ##STR22## wherein Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, alkylphenyl and halophenyl to form a N-phosphonomethylglycine iminourea salt of the general formula VII ##STR23## and then reacting said salt of formula VII with the appropriate amine, iminourea, diamine or diiminourea as defined.

Claim 5

at least one but no more than two of R 1 , R 2 or R 3 are R 4 , 2. no more than one R 5 , R 5' , R 6 , R 6' , are aryl or substituted aryl; and 3. no more than one of R 5 , R 5' , R 6 , R 6' , and R 7 is CH 2 OH; or (b) R 1 , R 2 and R 3 are independently selected from hydrogen and R 16 wherein R 16 is a salt-forming cation selected from the groups consisting of cations of organic ammonium selected from primary-, secondary- and tertiary-alkyl, none of these having more than two amine groups; and heterocyclic amines provided that no more than two of R 1 , R 2 and R 3 are --R 16 ; or (c) R 1 and R 2 are hydrogen and R 3 is R 17 wherein R 17 is a salt forming cation of the formula III ##STR20## wherein R is selected from the group consisting of C 2 -C 12 straight or branched chain alkylene radicals and R 8 and R 9 are each independently H or a C 1 -C 4 alkyl group; or (d) R 1 and R 2 are H and R 3 is a salt forming cation of the formula IV ##STR21## wherein Y is N, R 18 is a straight or branched chain alkylene radical having 1-12 carbon atoms and R 19 , R 11 , R 12 and R 10 are each independently H, alkyl, phenyl or allyl provided that only one of R 19 and R 10 may be alkyl, allyl or phenyl and only one of R 11 and R 12 may be alkyl, allyl or phenyl; said process comprising oxidizing an aryl substituted iminourea salt of N-phosphonomethyliminodiacetic acid of the formula VI ##STR22## wherein Ar 1 and Ar 2 are each independently selected from the group consisting of phenyl, alkylphenyl and halophenyl to form a N-phosphonomethylglycine iminourea salt of the general formula VII ##STR23## and then reacting said salt of formula VII with the appropriate amine, iminourea, diamine or diiminourea as defined.

Claim 6

A process according to claim 1 wherein the resulting NPMG salt solution is separated by filtration from the regenerated aryl-substituted iminourea which iminourea is purified and recycled for use in the preparation of the salt of formula VI.

Claim 7

A process according to claim 1 wherein said oxidation is carried out using hydrogen peroxide as an oxidizing agent.

Claim 8

A process according to claim 1 wherein said oxidation is carried out using a molecular oxygen-containing gas in the presence of a metal or activated carbon catalyst.

Claim 9

A process according to claim 1 wherein the salts of formula VI are first prepared by forming an admixture of N-phosphonomethyliminodiacetic acid and an imino urea selected from the group consisting of N, N' diphenyl guanidine, N,N'di-o-tolyl guanidine; N,N'-di-p-tolyl guanidine, N,N'-Di-4-Ethyl phenyl guanidine, N,N'-Di-4-Chloro phenyl guanidine and N,N'-di-4-bromo phenyl guanidine and heating the mixture until a clear solution is obtained.

Claim 10

A process according to claim 1 wherein said oxidation is carried out at a temperature of about 70° to about 120° C.