Fatty Acid Diesters Research Articles

Preparation of Some New Ethylene Glycol Monoesters and Mixed Diesters of Fatty Acids

AbstractTri‐(2‐hydroxyethyl)‐orthoborate, obtained by reaction of ethylene glycol with boric acid, was esterified with palmitic, stearic, arachidic, oleic, hydnocarpic, elaidic and stearolic acids. Pure monoesters were obtained on hydrolysis with water in high yields. Monoelaidate and monostearolate are reported for the first time. The monoesters were reacted with acyl chlorides to yield the mixed diesters, viz., oleostearate, oleopalmitate, oleoarachidate, oleoelaidate, oleostearolate, elaidohydnocarpate, stearocaproate and stearolaurate. Except oleostearate the other compounds are reported for the first time.

The occurence of diester waxes in human vernix caseosa and in hair lipids of common laboratory animals

1. 1. The hair lipids of rabbit and cat contain diesters of hydroxy fatty acids with aliphatic monohydric alcohols and unsubstituted fatty acids (Type I). 2. 2. The lipids of human vernix caseosa and the hair lipids of mouse and guinea-pig contain diesters of aliphatic diols with unsubstituted fatty acids (Type II). 3. 3. The main fraction of the dog hair lipids gives rise to diols and unsubstituted fatty acids upon hydrolysis, but it is not identical with the Type II diester waxes.

Pyrolysis of Ethylene Glycol Fatty Acid Esters

Four ethylene glycol di-fatty acid esters (A) and four ethylene glycol mono-fatty acid esters (B), prepared from ethylene glycol and butyric, caprylic, lauric and palmitic acid, were pyrolyzed at 200750°C in nitrogen atmosphere. The products of pyrolysis of the former (A) were fatty acids and fatty acid vinyl esters and a small amount of lower fatty acids and ketones, and those of the latter (B) were fatty acids and acetaldehyde and a small amount of fatty acid vinyl esters, lower fatty acids and ketones.

Interaction of Sucrose and Propoxylated Sucrose Esters with Some Pharmaceuticals

The interaction between either fatty acid mono or diesters of sucrose or fatty acid monoesters of propoxylated sucrose and benzoic acid or a series of hydroxy and amino substituted benzoic acids is reported. The sugar esters, because of their lack of long polyether chains, have been proposed for use in formulations in which association between a nonionic emulsifier and preservative is a problem. A dialysis method was used to study the interactions. The degree of interaction appears to be dependent upon the type of functional group present and its position in the complexed molecule. In the case of the surfactant the esters of the propoxylated sucrose appear to associate more than those of sucrose. The fatty acid moiety influences the extent of interaction; of the series studied, the laurate esters generally undergo interaction to the greatest extent, while the stearate esters exhibit only slight interaction. The results obtained differ to some degree from work previously reported with other nonionic surfactants. A possible mechanism of interaction based upon the binding of drug within the palisade layer of the micelles of the surfactant solution is proposed. The interaction between either fatty acid mono or diesters of sucrose or fatty acid monoesters of propoxylated sucrose and benzoic acid or a series of hydroxy and amino substituted benzoic acids is reported. The sugar esters, because of their lack of long polyether chains, have been proposed for use in formulations in which association between a nonionic emulsifier and preservative is a problem. A dialysis method was used to study the interactions. The degree of interaction appears to be dependent upon the type of functional group present and its position in the complexed molecule. In the case of the surfactant the esters of the propoxylated sucrose appear to associate more than those of sucrose. The fatty acid moiety influences the extent of interaction; of the series studied, the laurate esters generally undergo interaction to the greatest extent, while the stearate esters exhibit only slight interaction. The results obtained differ to some degree from work previously reported with other nonionic surfactants. A possible mechanism of interaction based upon the binding of drug within the palisade layer of the micelles of the surfactant solution is proposed.

Synthesis of Fatty Acid Diesters of the Sulfur Analogs of Batyl and Chimyl Alcohols

Synthesis of Fatty Acid Diesters of the Sulfur Analogs of Batyl and Chimyl Alcohols

Methyl glucoside fatty acid diesters

Summary and ConclusionProcedures are described for the preparation of methyl glucoside diesters by direct esterification, using a ratio of one mole of methyl glucoside with two moles of fatty acids. Rate studies indicated that lead or stannous soaps are more effective catalysts than the sodium soaps for speeding up tis esterification. With equal molar quantities of methyl glucoside and fatty acid, the lead and the sodium soap catalysts give products containing predominantly diester and half the methyl glucoside remaining unreacted. Under the same conditions stannous soap catalysis gives high yields of monoesters containing only very small percentages of unreacted methyl glucoside. From the standpoint of speed of reaction, color of the final produets, ease of removal of catalyst from the ester products, and catalyst cost, litharge is the preferred cytalyst for the preparation of methyl glucoside diesters.Properties of various methyl glucoside fatty acid diesters, prepared on a laboratory scale, are given. Du Noü;y surface‐tension measurements indicate that small quantities of the methyl glucoside dilaurate, dicaprate, or dioleate are quite effective in lowering the surface tension of water.

Some Properties of Licinoleyl Diesters of Lower Fatty Acids

Some Properties of Licinoleyl Diesters of Lower Fatty Acids

Urea adducts of mono‐ and diesters of fatty acids

The experimental work has shown how molecular configurations of fatty acid glycerides affect urea complex formation. Extraction data indicate that urea will form a complex with glycerol monopalmitate, monostearate, and mono-oleate but not under these conditions with glycerol monolinoleate or monolinolenate from mixtures containing these monoesters. Data also indicate that it is easier for urea to form a complex with monoglycerides than with diglycerides.

Urea adducts of mono‐ and diesters of fatty acids

SummaryThe experimental work has shown how molecular configurations of fatty acid glycerides affect urea complex formation. Extraction data indicate that urea will form a complex with glycerol monopalmitate, monostearate, and mono‐oleate but not under these conditions with glycerol monolinoleate or monolinolenate from mixtures containing these monoesters. Data also indicate that it is easier for urea to form a complex with monoglycerides than with diglycerides.In a mixture containing mono‐ and diglycerides of saturated and unsaturated fatty acids, urea will separate first on the basis of saturation, then secondly on the basis of the degree of esterification of the glycerol.