GB1308793A - Nitrotriacetic acid anhydrides and derivatives thereof - Google Patents

Abstract

1308793 Nitrilotriacetic acid derivatives STAUFFER CHEMICAL CO 28 July 1970 [18 Aug 1969] 36390/70 Headings C2C and C2P [Also in Division C3] The invention comprises compounds of the formula provided that when R is H, Z is other than H and when Z is H, R is other than H and when R is cycloalkyl or heterocycloalkyl then Z and R are connected by an alkylene bridge, and compounds of the formula where R and R 1 -R 5 are H, alkyl, substituted alkyl, aryl, substituted aryl, peptide, carboxyalkyl, substituted carboxyalkyl, heteroaryl, alkyl substituted heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkenyl, heterocycloalkyl, a carbohydrate, a mono or polysaccharide, provided the R cannot be hydrogen in Formula V and providing that at least one R group in Formula VI is not hydrogen, Z is hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, peptide, carboxyalkyl, substituted carboxyalkyl, heteroaryl, alkyl substituted heteroaryl, cycloalkyl, cycloalkenyl, heterocycloalkenyl, heterocycloalkyl, a carbohydrate, a mono or polysaccharide or OH, OR or where M<SP>(+)</SP> is an alkali or alkaline earth metal, m is 0-20, n is 1-10,000 and g is 0-10,000. Monomeric and dimeric nitrilotriacetic anhydride are prepared by reacting the nitrilotriacetic anhydride with a dehydrating agent selected from an alkyl or aryl carboxylic acid anhydride, a dicarboxylic acid anhydride, an N,N<SP>1</SP>-disubstituted carbodiimide or a haloaliphatic acid anhydride in the presence of a solvent of the formula where Y, Y<SP>1</SP> and Y<SP>2</SP> are H, alkyl, substituted alkyl, aryl or substituted aryl and n is 2-5. The compounds of Formulµ III-XI are prepared by reacting monomeric or dimeric nitrilotriacetic anhydride with a compound having a hydrogen atom replaceable by an acyl function. A phosphorus derivative referred to is diethanolaminomethylphosphonate - bisnitrilotriacetate.