GB723316A - Substituted alkylene polyamine acetic acid compounds - Google Patents

Abstract

The invention relates to alkylene polyamine polyacetic acid compounds having the general formula <FORM:0723316/IV (b)/1> wherein R is an alkyl or substituted alkyl group containing 1 to 18 carbon atoms, Alkylene represents -CH2.CH2-, CH3-CH-CH2-, <FORM:0723316/IV (b)/2> , n is 0, 1 or 2 and M is H, NH4, K, Na or an amine. They may be prepared by various methods. Thus, an appropriate a -amino-acid salt (2 mols.) may be reacted with 1 mol. of an alkylene dihalide X-alkylene-(NH-Alkylene)n-X, wherein X is a halogen and Alkylene and n have the above meanings and the product is then N-alkylated by means of an alkali-metal chloroacetate in alkaline solution or as described in Specification 600,629, forming the desired polyacetic derivative which may be isolated in the form of the free acid or above-specified salts. A second method comprises reacting a salt of an appropriate a -halo acid (2 mols.) with 1 mol. of a polyamine NH2-Alkylene-(NH-Alkylene)n-NH2, n and Alkylene having the above meanings and the product is then N-alkylated as before. A third method involves the use of an appropriate a -hydroxy acid salt in method (2). The products are chelating agents; the salts are surface tension reducing and foaming agents; the free acids may be used as anti-oxidants in fats, oils and fatty acids. Some may be used as plasticizers and co-polymerizing emulsants. In examples, (1) alanine sodium salt is reacted with ethylene dibromide in aqueous medium at pH 10 and the resulting ethylene diamine-di-alanine is recovered as free acid on acidification and is reacted with sodium chloracetate in aqueous solution yielding on acidification ethylene diamine-bis-alanine-N,N1-di-acetic acid; (2) ethylene bis-(a -amino caproic acid)-N : N1-di-acetic acid is obtained in like manner using a -amino caproic acid sodium or potassium salt in place of sodium alanine; leucine and iso-leucine may be used similarly; (3) a -amino undecanoic acid; and (4) an a -amino C9 branched chain acid are used as in (1); (5) an a -amino C10 branched chain acid is used as in (1) the first stage, however, being effected in n-butyl alcohol. The properties of the partial sodium and potassium salts of various of these products are discussed. Many other a -amino acid reactants are mentioned including a -amino butyric and a -amino valeric acids and serine, phenyl-alanine, tyrosine, valine, tryptophane, cysteine, cystine and methionine.