Surfactants and detergents from sulfated N‐alkyl‐gluconamides

Abstract

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...

Surface properties of surfactants derived from natural products. Part 1: Syntheses and structure/property relationships—Solubility and emulsification

“…Only the characteristic spectral peaks of new compounds are presented. More analytical data are found in other sources (13)(14)(15)(16)(17)(18)(19)(20)(21)(22).…”

“…Alkyl/aryl-D-gluconamides (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18) (14,19). In a 50-mL round bottle with stirrer D-(+)-glucono-1,5-lactone (1.78 g, 10 mmol, 1 eq) and a primary or secondary amine (20.0 mmol, 2 eq) are dissolved in dimethylsulfoxide (DMSO) (20 mL).…”

“…A range of nonionic D-gluconamides, compounds 6-18 (Scheme 2), some of which, 11-14, have been described previously (15), also were prepared and characterized. Gluconamides have previously been used in commercial products as hydrotropes (16).…”

Effective sugar-derived organic gelator for three different types of lubricant oils to improve tribological performance

“…NOG was synthesized according to a previously reported protocol [16]. Briefly, 20 mmol δ-glucolactone was dissolved in 100 mL methanol at 60 °C , and then added to a mixture of methanol (50 mL) and n-octadecylamine (20 mmol).…”

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

“…Bicyclic systems like carboxymethylglycoside lactones (CMGLs) prepared from isomaltulose [227][228] or from the oxidation of corresponding allyl glycosides [229] provide amphiphilic amides by treatment with fatty amines in anhydrous CH 2 Cl 2 . Let us note that further functionalization of glucamides can be performed, such as in the case of sulfated urnoamides [230,231]. Analogous sugar thioamides have been obtained using Lawesson's reagent and the peracteylated glucamide [232].…”