Process For Preparing Acylglycinates And Compositions Comprising Such Compounds

Abstract

A process for preparing acylglycinates of the formula (I) wherein R 1 is a linear or branched, saturated alkanoyl group having 6 to 30 carbon atoms, or is a linear or branched, singly or multiply unsaturated alkenoyl group having 6 to 30 carbon atoms, and Q + is a cation, wherein glycine is reacted with fatty acid chloride R 1 Cl, in water and in the presence of a basic alkali metal compound which yields cations Q + , but in the absence of organic solvents, at 25 50 ° C. Also described are compositions comprising acylglycinates of the formula (I).

1 . A process for preparing an acylglycinate of the formula (I) 
       
         
           
           
               
               
           
         
         in which 
         R 1  is a linear or branched, saturated alkanoyl group having 6 to 30 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenoyl group having 6 to 30 carbon atoms, and 
         Q +  is a cation selected from the group consisting of alkali metal cations Na +  and K + , 
         comprising the step of reacting glycine with at least one fatty acid chloride R 1 Cl where R 1  is as defined above in formula (I), in water and in the presence of at least one basic alkali metal compound, wherein the at least one basic alkali metal compound provides cations Q + , wherein Q+ is selected from the group consisting of alkali metal cations Na +  and K + , but in the absence of organic solvents, at 25 -50° C., and 
         wherein the proportion of the at least one fatty acid chloride R 1 Cl containing unsaturated acyl groups R 1  having 18 carbon atoms, based on the total amount of fatty acid chloride used, is greater than or equal to 2.0% by weight and, at the same time, the proportion of fatty acid chloride containing saturated acyl groups having 8 and 10 carbon atoms, based on the total amount of fatty acid chloride used, is greater than or equal to 3.0% by weight in each case. 
       
     
     
         2 . The process as claimed in  claim 1 , wherein the at least one basic alkali metal compound is a carbonate or hydroxide of the alkali metal cations Na +  or K +  or mixtures thereof. 
     
     
         3 . The process as claimed in  claim 1 , wherein the step of reacting is performed at a pH of 9 to 13. 
     
     
         4 . The process as claimed in  claim 1 , wherein the molar ratio of glycine to fatty acid chloride R 1 Cl is from 1.1:1.0 to 1.0:1.0. 
     
     
         5 . The process as claimed in  claim 1 , wherein
 the proportion of the at least one fatty acid chloride having saturated C8 acyl groups is greater than or equal to 3.0% by weight,   the proportion of the at least one fatty acid chloride having saturated C 10  acyl groups is greater than or equal to 3.0% by weight,   the proportion of the at least one fatty acid chloride having C12 acyl groups is 40.0-55.0% by weight,   the proportion of the at least one fatty acid chloride having C14 acyl groups is 13.0-22.0% by weight,   the proportion of the at least one fatty acid chloride having C16 acyl groups is 5.0-11.0% by weight,   the proportion of the at least one fatty acid chloride having saturated C18 acyl groups is 0-5.0% by weight, and   the proportion of the at least one fatty acid chloride having unsaturated C18 acyl groups is greater than or equal to 2.0% by weight, based in each case on the total amount of fatty acid chloride used, is reacted.   
     
     
         6 . The process as claimed in  claim 5 , wherein
 the proportion of the at least one fatty acid chloride having saturated C8 acyl groups is 3.0-10.0% by weight,   the proportion of the at least one fatty acid chloride having saturated C 10  acyl groups is 3.0-10.0% by weight,   the proportion of the at least one fatty acid chloride having C12 acyl groups is 40.0-55.0% by weight,   the proportion of the at least one fatty acid chloride having C14 acyl groups is 13.0-22.0% by weight,   the proportion of the at least one fatty acid chloride having C16 acyl groups is 5.0-11.0% by weight,   the proportion of the at least one fatty acid chloride having saturated C18 acyl groups is 0.1-5.0% by weight, and   the proportion of the at least one fatty acid chloride having unsaturated C18 acyl groups is 2.0-11.0% by weight,   based in each case on the total amount of fatty acid chloride used, is reacted.   
     
     
         7 . The process as claimed in  claim 6 , wherein
 the proportion of the at least one fatty acid chloride having saturated C8 acyl groups is 5.0-8.0% by weight,   the proportion of the at least one fatty acid chloride having saturated C 10  acyl groups is 5.0-8.0% by weight,   the proportion of the at least one fatty acid chloride having C12 acyl groups is 44.0-50.0% by weight,   the proportion of the at least one fatty acid chloride having C14 acyl groups is 14.0-20.0% by weight,   the proportion of the at least one fatty acid chloride having C16 acyl groups is 8.0-10.0% by weight,   the proportion of the at least one fatty acid chloride having saturated C18 acyl groups is 1.0-3.0% by weight, and   the proportion of the at least one fatty acid chloride having unsaturated C18 acyl groups is 4.0-10.0% by weight,   based in each case on the total amount of fatty acid chloride used, is reacted.   
     
     
         8 .- 19 . (canceled) 
     
     
         20 . The process as claimed in  claim 1 , wherein R 1  is a linear or branched, saturated alkanoyl group having 8 to 22 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenoyl group having 8 to 22 carbon atoms. 
     
     
         21 . The process as claimed in  claim 1 , wherein R 1  is a linear or branched, saturated alkanoyl group having 8 to 18 carbon atoms, or a linear or branched, mono- or polyunsaturated alkenoyl group having 8 to 18 carbon atoms.