R. G. Bistline

Long chain alkanesulfonates and 1-hydroxy-2-alkanesulfonates: Structure and property relations

Even chain sodium alkanesulfonates from the Strecker reaction, odd chain sodium alkanesulfonates from the alkaline decarboxylation of α-sulfo acids, and sodium 1-hydroxy-2-alkanesulfonates from the reduction of esters of α-sulfo acids were compared with respect to Krafft point, critical micelle concentration, detergency and foam height. Sodium alkanesulfonates and crude fusion products from the α-sulfo acids (mixtures of alkanesulfonates of one less carbon atom with a lesser amount of a soap of two less carbon atoms) are more soluble and have better detergent and foaming properties. Sodium 1-hydroxy-2-alkanesulfonates resemble monosodium salts of α-sulfo acids.Alkanesulfonic acids and 1-hydroxy-2-alkane-sulfonic acids obtained from the sodium salts by ion exchange have lower Krafft points and are more readily soluble. The critical micelle concentrations of 1-hydroxy-2-alkanesulfonic acids and α-sulfo acids are nearly the same and about equal to those of alkanesulfonic acids of one less carbon atom.

Lipase-catalyzed triglyceride hydrolysis in organic solvent

An investigation of lipases fromRhizomucor miehei,Candida rug osa and porcine pancreas revealed that these enzymes hydrolyzed triglycerides in an organic solvent system. The presence of secondary amines,i.e., diethylamine,N-methylbutylamine, or the tertiary amine, Methylamine, greatly increased the extent of hydrolysis. The lipolysis of tallow took place under mild conditions,e.g., room temperature, moderate shaking and within 20 hr. At 45°C, complete hydrolysis of tallow was obtained in 6 hr. Vegetable oils and a fish oil (cod liver oil) were also hydrolyzed at 20°C byR. miehei lipase in the presence of iV-methylbutylamine for 20 hr. The lipases were recovered for reuse with some loss of activity. Optimum yields of free fatty acids were obtained by usingR. miehei lipase as catalyst.

Lipase catalyzed formation of fatty amides

Certain lipase preparations were found to facilitate the preparation of fatty amides at 20°C in hexane. Lipase preparations investigated were from the fungiCandida rugosa, Rhizomucor miehei and porcine pancreas. Reactants were various primary alkylamines and fatty acid methyl esters or triglycerides. Moderate yields of fatty amides were obtained using aR. miehei lipase preparation which is immobilized on a solid support as catalyst, although all three lipase preparations showed some catalytic activity under these conditions and, in addition, showed different kinds of selectivity for fatty acid and alkylamine chain lengths. No reaction was observed in similar experiments using one fatty acid as the substrate or one secondary amine.

Soap-based detergent formulations I. Comparison of soap-lime soap dispersing agent formulations with phosphate built detergents

Blends of soap with small amounts of lime soap dispersing agents are efficient detergents in hard water and require little or no tripolyphosphate builder. Lime soap dispersing agents examined include sulfated ethoxylated fatty alcohols, sulfated N-(2-hydroxyethyl) fatty amides, methyl esters of α-sulfo fatty acids, 2-sulfoethyl fatty acid esters and N-methyl-N-(2-sulfoethyl) fatty amides as well as nonionics derived from tallow alcohols. Detergency evaluations were carried out with three commercial soiled cotton cloths as well as by a laboratory multi-wash technique. Formulations containing 80% soap, 10% lime soap dispersing agent and 10% builder gave optimum detergency values. Builder effectiveness was rated tripolyphosphate>silicate (1:1.6)> metasilicate = citrate = oxydiacetate = nitrilotriacetate>carbonate≫sulfate. The detergency of soap-lime soap dispersed combinations compared favorably with a standard brand household heavy duty granular detergent in 50, 150 and 300 ppm hardness water on three soiled cloths.

Soap-based detergent formulations: X. Nature of detergent deposits

The cumulative deposition of detergent residue on unsoiled cotton and polyester-cotton permanent press finish cloth was determined for a variety of detergent formulations after washing 25 consecutive times in 300 ppm hard water in a laboratory Tergotometer. Included in this study were: a phosphate-built laundry detergent, two carbonate-built detergents, tallow soap and various tallow soap formulations with anionic and amphoteric lime soap dispersing agents, and a glassy sodium silicate. Sample swatches washed with each formulation were analyzed for calcium, magnesium, and organic acid content. Fabric washed with the carbonate detergents showed the highest calcium and magnesium content, while those washed with the phosphate detergent and the soap-lime soap dispersant-builder formulations had the lowest. Fabric washed with soap alone had a much higher fatty acid residue than those washed with the other detergent formulations. However, the amount of organic acids left on the fabric after washing with a soap-lime soap dispersing agent formulation was no greater than that produced by phosphate- and carbonate-built detergents. The presence or absence of deposits also was verified visually with a scanning electron microscope. Each formulation also was tested for detergency by measuring the soil buildup in a multiwash procedure. Generally, the buildup of soil paralleled the deposit of detergent residue on the unsoiled cloths.

Soap-based detergent formulations: VI. Alkylaryl sulfonamide derivatives as lime soap dispersing agents

Alkylbenzenes, such as industrial detergent alkylates, as well as pure 1-phenylalkanes whose side chain lengths varied C8−C12, were converted into the corresponding alkylbenzenensulfonyl chlorides with chlorosulfonic acid. Surface active sulfonamides were obtained from the reaction of the sulfonyl chlorides with various low mol wt aminosulfonic acids, such as N-methyltaurine, or with aminoalkyl esters of sulfuric acid, such as 2-aminoethyl hydrogen sulfate. The hydrolytic stability of the resulting surface active sulfonamide derivatives was investigated. As expected, the sulfonates were quite resistant to acid or alkaline hydrolysis, while the sulfates were more susceptible to hydrolysis. Hydrolytic stability of the sulfonamides was compared with that of the analogous fatty acid amide sulfactants. All of the compounds were excellent lime soap dispersing agents giving Borhetty-Bergman values of 4–10. The compounds were evaluated for detergency either alone or formulated either with tallow soap or with tallow soap and sodium silicate (Na2O/SiO2 ratio of 1∶1.6) The derivatives of the pure hydrocarbons which gave the best overall detergency were those of 1-phenyldecane and 1-phenyldodecane, whereas those of 1-phenyloctane exhibited poor detergency. This ranking was observed when the compounds were tested alone as well as when formulated. The sulfonamide derivatives of the detergent alkylate type of alkylbenzenes exhibited excellent detergency characteristics and showed substantial potentiation of detergency when mixed with soap or with a soap-sodium silicate blend. The detergency performance of some of these formulated detergents was equal to that of a commercial household detergent used as a control.

Amides ofa-sulfonated palmitic and stearic acids

SummaryCarboxylic acid amides of α-sulfopalmitic and α-sulfostearic acids were prepared from ammonia, ethylamine, ethanolamine, isopropylalcoholamine, diethanolamine, and N-methyltaurine, and were isolated as the sodium, ammonium, or ethanolammonium salt.A satisfactory method was found to be the reaction of the sulfocarboxylic acid with an excess of thionyl chloride, and further reaction of the acid chloride with an amine in a chlorinated solvent. More work is needed on the application of direct amidation methods to the preparation of these compounds.The solubility of the α-sulfonated amides increased with substitution of alkyl, hydroxyalkyl, and sulfoalkyl groups at the nitrogen atom. Ethanolammonium N-hydroxyethyl-α-sulfopalmitamide, ethanolammonium N-hydroxyethyl-α-sulfostearamide, sodium N-(2-hydroxypropyl)-α-sulfostearamide, sodium di-(N-hydroxyethyl)-α-sulfostearamide, and disodium N-methyl,N-(2-sulfoethyl)-α-sulfostearamide have aqueous solubility in excess of 10% at room temperature.Most of the sodium salts of the α-sulfonated amides have good or excellent stability to calcium and other divalent ions and are excellent lime soap dispersing agents.

Cosulfation of fatty acid alkanolamides and lower molecular weight alcohols

Abstract and SummaryThe process for the sulfation of tallow isopropanolamide or of a 50:50 mixture of tallow diglycolamide and isopropanolamide with chlorosulfonic acid was studied. The major obstacle to complete and uniform sulfation was the high viscosity of the sulfation mix. This could be overcome most advantageously by cosulfation with lower molecular weight alcohols, preferably isopropanol. The most fluid reaction mix and product were prepared from the mixed amides. No chlorinated solvent is required for such cosulfations.

Reaction of fatty acids with 3,3′-iminobis-propylamine to produce soil hydrophobic agents

AbstractThe reaction between two moles of fatty acid and one of 3,3′-iminobis-propylamine (DPTA) is somewhat analogous to the reaction between fatty acid and diethylenetriamine (DETA) that we had reported previously, but there are significant differences. Conversion to the diamide HN(CH2CH2CH2NHCOR)2 proceeds much more rapidly but less efficiently than does the reaction of fatty acid with DETA. The former diamide is obtained in only about a 70% yield and byproducts are obtained, whereas the reaction with DETA yields the diamide almost quantitatively. Cyclization to the pyrimidine % MathType!MTEF!2!1!+-% feaafiart1ev1aaatCvAUfeBSjuyZL2yd9gzLbvyNv2CaerbuLwBLn% hiov2DGi1BTfMBaeXatLxBI9gBaerbd9wDYLwzYbItLDharqqtubsr% 4rNCHbGeaGqiVu0Je9sqqrpepC0xbbL8F4rqqrpepeei0xd9vqVe0x% b9q8qqqrpe0db9pwe9Q8fs0-yqaqVepee9pg0Firpepe0de9vr0-vr% 0-vqpWqaaeaabiGaciaacaqabeaadaqaaqaaaOqaaGqaaiaa-jfaca% WFdbGaa83taiaa-5eacaWFibGaa83qaiaa-HeadaWgaaWcbaGaa8Nm% aaqabaGccaWFdbGaa8hsamaaBaaaleaacaWFYaaabeaakiaa-neaca% WFibWaaSbaaSqaaiaa-jdaaeqaaOGaa8hiaiaa-5eacaWFdbGaa8hs% amaaBaaaleaacaWFYaaabeaakiaa-neacaWFibWaaSbaaSqaaiaa-j% daaeqaaOGaa83qaiaa-HeadaWgaaWcbaGaa8NmaaqabaGccaWFobGa% a8hiaiaa-1dacaWFGaGaa83qaiaa-jfaaaa!4F73!