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N UMEROUS patents describe the preparation of ethers, esters, amines, and amides of carbohydrates and their sulfated and sulfonated derivatives for detergent use (1), but apparently the sulfuric acid esters of long-chain aliphatic amides of D-gluconic acid have not been investigated. Recent large-scale production of fatty amines and rosin amine and the ready availability of D-gluconolaetone from D-gluconic acid (2) has stimulated a study of the reaction products of these materials as intermediates for the preparation of interracial modifiers.This paper presents the synthesis of N-rosin-D-gluconamide and a series of N-alkyl amides of D-gluconic acid and their sulfated derivatives. Some physical and chemical properties of the sulfated products were determined and used to evaluate them as surface active agents. Comparative soil removal studies were also made with a number of the products, alone and in combination with builders, in hard and distilled water under conditions similar to those used in home laundry practices.The octyl, decyl, dodecyl, tetradecyl, hexadecyl, and octadecyl amines investigated were mixtures of at least 90% of the appropriate amine and about 10% of amines of slightly higher and lower molecular weight. The 2-ethylhexylamine and nonylamine (3,5,5trimethylhexylamine) used were pure substances. The major components of the rosin amine were dihydroabietyl, tetrahydroabietyl, dehydroabietyl, and dextropimarylamines (3). D-gluconic acid cannot readily be reacted with primary amines to form amides because tlle high temperature required for condensation decomposes the sugar acid. However D-glucono-delta-lactone which is easily crystallized by evaporating aqueous D-gluconic acid solution to 85% concentration can be reacted at relatively low temperatures to form substituted D-gluconamides (I) in excellent yield. Reaction of the substituted D-gluconamides with chlorosulfonic acid in dry methylene chloride and neutralization of the product with aqueous sodium hydroxide has readily produced N-alkyl-D-glueonamide sodium sulfates (II). This sequence of reactions may be illustrated as follows: IIThe monosulfates are assumed to have the sulfate group attached to carbon six since primary alcohol groups of sugars (4) generally esterify more rapidly than secondary hydroxyl groups. that the N-alkyl-D-gluconamide sodium monosulfates containing alkyl radicals of more than nine carbon atoms are incompletely soluble in 1% aqueous solution. Introduction of a second or third sulfate group conferred the solubility desired.While the sulfated N-alkyl-D-gluconamides are not as stable in aqueous solution as sulfonated detergents, the sulfate radical is sufficiently firmly attached to the molecule to allow their satisfactory use in neutral, mildly acid, or alkaline solutions. N-rosin-D-gluconamides were prepared by interaction of D-glueono-delta-lactone and the primary amines in hot methanol. The desired products readily crystallized from their reaction mixtures. A typical procedure for the synthesis of N-2-ethylhexyl-D-gluco...

Dimethylene-D-gluconic acid was first prepared by Henneberg and Tollens2 who suggested the most probable structure to be 3,4; 5,6-dime thylenegluconic acid (I). No experimental proof for this configuration was given, however, and the possibility existed that the compound could have one of a number of other structures.