E. W. Maurer

Synthetic detergents from animal fats. X. Sulfated, ethenoxylated tallow alcohols

SummarySulfated ethenoxylated tallow alcohols of average composition corresponding to the formulas C16H33(OC2H4)2OSO3Na, C18H37(OC2H4)2OSO3Na, and C18H37(OC2H4)10OSO3Na, were prepared by ethenoxylation and sulfation of hexadecanol and octadecanol.The incorporation of two ethenoxy groups improved solubility without loss in detergency compared to the corresponding sodium hexadecyl and octadecyl sulfates. With consideration also of economy in the number of ethenoxy groups, two appear to be near the optimum. The product with 10 ethenoxy groups was an even more readily soluble but less effective detergent.Of the sulfated ethenoxylated tallow alcohols, sodium hexadecyloxyethoxyethyl sulfate [C16H33(OC2H4)2OSO3Na] had the lowest surface-tension and the best foaming properties; sodium octadecyloxyethoxyethyl sulfate [C18H37(OC2H4)2OSO3Na] was the best emulsifying agent; and the product with 10 ethenoxy groups [C18H37(OC2H4)10OSO3Na] had the greatest stability in regard to metallic ions and to acid hydrolysis.All three were excellent lime-soap dispersing agents with good or excellent emulsifying properties and stability in regard to metallic ions.

The biodegradation of esters of α-sulfo fatty acids

Abstract and SummaryMethyl and aminoalkyl esters of α-sulfonated fatty acids in the C9-C18 range were subjected to aerobic biodegradation in a controlled nutrient medium in which sewage microorganisms were used as the inoculum and the test compound was the sole source of carbon and energy. The extent of biodegration increased with increasing alkyl chain length of the α-sulfo fatty acid and decreased with increasing substitution on the amino nitrogen and possibly with the increasing molecular weight of the substituent on the amino nitrogen atom. No connection was found between the degree of biodegradability and anti-microbial activity of the test compounds. Methyl α-sulfopalmitate was the compound of this study most inhibitory againstStaphylococcus aureus.

The course of biodegradation of anionic detergents by analyses for carbon, methylene blue active substance and sulfate ion

Tallow alcohol sulfates, ether alcohol sulfates and esters of α-sulfo tallow fatty acids were degraded aerobically by sewage microorganisms in a system in which detergent was the sole source of C. Biodegradation was followed by loss of C and methylene blue active substance (MBAS) and formation of SO4−−. Tallow alcohol sulfates were rapidly and completely degraded; ether alcohol sulfates not quite as readily. Reduction in MBAS was rapid for the α-sulfo esters but loss of C and SO4−− formation was incomplete, possibly because of the intermediate formation of a resistant sulfosuccinate. Sodiump-(1-methylundecyl) benzenesulfonate (LAS) was the reference standard.

The effect of tallow-based detergents on anaerobic digestion

Eight anionic detergents from three general classes (alcohol sulfates,a-sulfo fatty acid esters and alkylbenzenesulfonates were tested for biodegradability under anaerobic conditions of sludge digestion. The alcohol sulfates were found to be readily and completely degraded. Thea-sulfo fatty acid esters did not degrade but had no adverse effect on bacteriological digestion while the alkylbenzenesulfonates used for control purposes did not degrade and disrupted the normal digestion process.Preliminary lysimeter studies showed that sodium isopropyla-sulfostearate is completely degraded, linear alkylbenzenesulfonate 83%, and ABS 35%.

Synthetic detergents from animal fats. VII. Detergent combinations

SummaryLaboratory measurements of detergency were made on mixtures of sodium salts of sulfated hydrogenated tallow alcohol (X), disodium salts of α-sulfonated hydrogenated tallow acids (Y), sodium dodecylbenzenesulfonate (Z), and a builder (B) using three different kinds of standard soiled cotton. Component X was the most important, and mixtures not containing X were generally inferior detergents. Built XY mixtures were better than XZ mixtures with one kind of soiled cotton (cloth I). Built XZ mixtures were better than XY mixtures with another soiled cotton (cloth III).The results, based on laboratory measurements of detergency using standard soiled cotton, are suggestive rather than conclusive. Partial substitution of X by Y or Z, or by both Y and Z, may be possible without loss in detergency.

Synthetic detergents from animal fats. IV. Sodium 9,10-dichlorooctadecyl sulfates

SummarySodium 9,10-dichlorooctadecyl sulfates were prepared by the addition of chlorine to oleyl and to elaidyl alcohols, and sulfation of the dichlorooctadecanols with chlorosulfonic acid. The sodium 9,10-dichlorooctadecyl sulfates are readily soluble in water at 25°C and resemble sodium oleyl sulfate in detergent and surface-active properties. Tallow alcohols can be chlorinated by the addition of chlorine and sulfated with one of the usual sulfating agents to produce an adequately soluble detergent and surface-active agent.

Biological behavior of some soap-based detergents

The biodegradability of tallow soap, three soap-based detergent formulations and their component lime soap dispersing agents—sodium methyl α-sulfotallowate, sulfated N-(2-hydroxypropyl) tallowamide, and sodium N-methyl N-(2-sulfoethyl) tallowamide—was determined under aerobic and microaerophilic conditions. Both sewage and river water microorganisms were used as the sources of inoculum. The course of biodegradation was followed by loss of carbon and methylene blue active substance, and by increase in turbidity and surface tension. Carbon analysis for soap in solutions containing Ca++ and Mg++, which would precipitate soap, was performed by an improved technique using the disodium salt of ethylenediamine tetraacetic acid. Invariably a decrease in carbon content was accompanied by an increase in turbidity and surface tension. Also, loss in methylene blue active substance was concurrent with an increase in turbidity and surface tension of the degrading solutions of the detergent. Soap cannot be determined as methylene blue active substance because of the low pH of the test. Soap and the built soap formulations degraded under aerobic and microaerophilic conditions. Preliminary toxicity data upon mammals and fish indicated that the soap-based detergents are as safe as conventional commercial detergents.

Octadecylsulfuric acid. Properties of the acid, amine salts, and salts of amino acids

SummaryOctadecanol, hexadecanol, tetradecanol, and dodecanol were sulfated with chlorosulfonic acid, and the corresponding alkylsulfuric acids were isolated in a pure state as white crystalline solids with definite melting points.Octadecylsulfuric acid resembles sodium octadecyl sulfate in detergent and surface-active properties and in stability to hydrolysis at equal concentrations of hydrogen ion. It is more soluble in water than sodium octadecyl sulfate and readily soluble in organic solvents. The critical micelle concentration (0.0387 millimoles/I.) is only about one-third that of the sodium salt.Isolation of octadecylsulfuric acid as a useful chemical intermediate made possible the preparation of a number of salts with amines and amino acids and their rapid screening for useful properties.

Detergent bars from salts ofa-sulfonated tallow acids

Summary and ConclusionsExperimental detergent bars were based entirely on selected salts of α-sulfonated saturated tallow acids. Some compositions appear to merit further investigation for the production of finished detergent bars, and an opportunity exists for the discovery of favorable combinations with soap. General conclusions are these.1.Attractive detergent bars can be made from the monosodium or monoammonium salt [RCH (SO3M)CO2H] by partial neutralization with an amine or mixture of amines. Representative bars had the following compositions in mole percentage, anhydrous basis: a) 72 monosodium, 20 sodium ammonium, 8 sodium triethanolammonium salts; b) 85 monoammonium, 15 ammonium ethanolammonium salts.2.Hardness and solubility can be controlled by water content and particularly by choice of the amine and the extent of the partial neutralization. Triethanolamine, isopropanolamine, and triethylamine tend to produce softer and more soluble bars than do ethanolamine or ethylamine.3.The following compositions were suitable for detergent bars useful in sea water: a) 80 mole percentage of disodium 20 acid triethanolammonium; b) 20 monosodium, 50 sodium ammonium, 30 sodium triethanolammonium.

Microaerophilic biodegradation of tallow-based anionic detergents in river water.

Nine anionic detergents from five general classes (alcohol sulfates, ether alcohol sulfates, sulfated alkanolamides, α-sulfo esters and alkylbenzenesul-fonates) were rapidly screened for biodegradability under aerobic and microaerophilic conditions in river water at 25 and 35 C. In decreasing order, the ease of biodegradation under microaerophilic conditions at 35 C was as follows: alcohol sulfates, sulfated alkanolamides, α-sulfo fatty acid esters and ether alcohol sulfates. Linear alkylbenzenesulfonate did not degrade.