Oxypropylation of fatty alcohols, and the sulfation products

Abstract

Reaction of propylene oxide, rather than ethylene oxide, with fatty alcohols, gives a higher yield (50%) of mono‐oxyalkylation product because the secondary alcohol formed is less reactive than the primary alcohol formed with ethylene oxide. Rate of further reaction is about half the rate of the parent primary alcohol. Distributuon of propylene oxide reaction products follows the Weibull‐Nycander equation.Analysis of reaction products was accomplished by gas‐liquid chromatography of the acetylated ether alcohol mixtures. Pure mono‐oxypropylated alcohols ROCH2CHOHCH3 and in some cases dioxypropylated alcohols R[OCH2CH(CH3)]2OH were separated by fractional distillation.Individual ether alcohols and products with a known average number of oxypropyl groups were sulfated and evaluated in terms of Krafft point, critical micelle concentration, detergency, foam height and lime soap dispersing properties. Incorporation of one oxypropyl group was more effective than the same degree of oxyethylation, and improved solubility with no significant loss in foaming and detergency. Ether alcohol sulfates from propylene oxide are stable to alkaline hydrolysis and nearly equal to the sulfates from ethylene oxide in their stability to acid hydrolysis.

Detection and analysis of unresolved multiplet chromatographic peaks

“…Manatt et al (9) employed 19F NMR spectrometry to determine these ratios in polyalkylene oxides which had been converted to trifluoroacetate esters. Gas-liquid chromatography (GLC), column chromatography, gel permeation chromatography, and thinlayer chromatography (TLC) have been used by numerous investigators to measure molecular weight distributions of oxyethylated p-alkylphenols or alcohols, and of polypropylene glycols (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23).…”

Foaming and Antifoaming by Aqueous Solutions of Surfactants

“…Thus, at 60 C, saturated straight-chain alkyl sulfates containing 16 carbon atoms, palmitate soaps, dodecyl-and tetradecylbenzenesulfonates (hydrophobic groups equivalent to 15.5-17.5 carbon chains), and a-sulfoesters containing 16-17 carbon atoms show maximum foaming power (Weil, 1954(Weil, , 1966Gray, 1955;Kölbel, 1959;Stirton, 1962;Micich, 1966). Near the boiling point, C 18 compounds are best.…”

Soap‐based detergent formulations: XVIII. Effect of structure variations on surface‐active properties of sulfur containing amphoteric surfactants

“…Stability of the amphoteric compounds to equimolar amounts of sodium hydroxide at 100 C or hydrochloric acid at 80 C was determined according to the method of Weil et al (7). The results for the sulfates are listed in Table I, along with corresponding data for an alkanesulfate (7) and sulfated alkanolamides (8) for comparison.…”