Process for the manufacture of alkylamino alkylene phosphonic acids

Abstract

A process for the manufacture of alkylamino alkylene phosphonic acids is disclosed. In detail, a specific phosphonate is reacted with an agent selected to yield an alkylamino moiety substituted by a radical selected from OH, OR', NH 2 , NHR′, N(R′) 2 , NH, N, S, S—S and SH in aqueous alkaline medium having a pH of 8 or higher at a temperature of 0° C. or higher.

1 . A process for the manufacture of alkylamino alkylene phosphonic acids having the formula:
   U—[X—N (W) (ZPO 3 M 2 )] s  
   by reacting a phosphonic acid compound having the formula:
   Y—X—N(W) (ZPO 3 M 2 )
 
   with a precursor of the moiety:   U   the structural elements having the following meaning:   Y is selected from: substituents the conjugated acid of which have a pKa equal to or smaller than 4.0;   X is selected from C 2 -C 50  linear, branched, cyclic or aromatic hydrocarbon chains, optionally substituted by a C 1 -C 12  linear, branched, cyclic, or aromatic group, (which chain and/or which group can be) optionally substituted by COOH, F, R 2 0 [A-O] x -wherein R 2  is a C 1 -C 50  linear, branched, cyclic or aromatic hydrocarbon chain, and SR′ moieties, wherein R′ is a C 1 -C 50  linear, branched, cyclic or aromatic hydrocarbon chain, optionally substituted by C 1 -C 12  linear, branched, cyclic or aromatic hydrocarbon groups, (said chains and/or groups can be) optionally substituted by COOH, F, and SR′; and [A-O] x -A wherein A is a C 2 -C 9  linear, branched, cyclic or aromatic hydrocarbon chain and x is an integer from 1 to 200;   Z is a C 1 -C 6  alkylene chain;   M is selected from H and C 1 -C 20  linear, branched, cyclic or aromatic hydrocarbon chains;   W is selected from H, ZPO 3 M 2  and [V-N (K)] n K, wherein V is selected from: a C 2 -C 50  linear, branched, cyclic or aromatic hydrocarbon chain, optionally substituted by C 1 -C 12  linear, branched, cyclic or aromatic groups, (which chains and/or groups can be) optionally substituted by OH, COOH, F, OR′, R 2 O[A-O] x -wherein R 2  is a C 1 -C 50  linear, branched, cyclic or aromatic hydrocarbon chain, and SR′ moieties; and from [A-O] x -A wherein A is a C 2 -C 9  linear, branched, cyclic or aromatic hydrocarbon chain and x is an integer from 1 to 200;   K is ZPO 3 M 2  or H and n is an integer from 0 to 200; and   U is a moiety selected from OH and OR′ wherein R′ is as defined above; s is 1,   in aqueous medium, having a pH of 8 or more, at a temperature of 0° C. or higher.   
     
     
         2 . The process as claimed in  claim 1  wherein the pH of the reaction medium is in the range of from 9-14. 
     
     
         3 . The process as claimed in  claim 1  wherein X is selected from C 2 -C 30  or [A-O] x -A wherein A is C 2 -C 6  and x is from 1-100 when U is OH. 
     
     
         4 . The process as claimed in  claim 1  wherein the individual moieties in the phosphonate reaction partner are selected as follows: X is C 2 -C 30  or [A-O] x -A; V is C 2 -C 30  or [A-O]  x -A; wherein for both, X and V independently, A is C 2 -C 6  and x is 1-100; R 2  is C 1 -C 30 ; Z is C 1 -C 3 ; M is H or C 1 -C 6 ; and n is 1-00. 
     
     
         5 . The process as claimed in  claim 1  wherein the individual moieties in the phosphonate reaction partner are selected as follows: X is C 2 -C 12  or [A-O]  x -A; V is C 1 -C 12  or [A-O] x -A; wherein for both, X and V independently, A is C 2 -C 4  and x is 1- 100; R   2  is C 1 -C 12i  Z is C 1 ; M is H or C 1 -C 4  and n is 1-25. 
     
     
         6 . The process as claimed in  claim 1  wherein the precursor for U is; OH. 
     
     
         7 . The process as claimed in  claim 2  wherein the precursor for U is OR′. 
     
     
         8 . The process as claimed in  claim 1  wherein Y is selected from Cl, Br, I, HSO 4r  NO 3 , CH 3 SO 3  and p-toluene sulfonate.