X-Ray diffraction study of sodium soaps of monounsaturated and polyunsaturated fatty acids

X-Ray powder diffraction patterns of the sodium soaps of 14 monounsaturated and polyunsaturated fatty acids were obtained at room temperature. The patterns of the soaps of 9,12-trans,trans-octadecadienoic acid, 11,14-cis,cis-eicosadienoic acid 11,14,17-allcis-eicosatrienoic acid and 5 monounsaturated fatty acids were typical of the crystalline lamellar phase. The patterns of the soaps of 9,12-cis,cis-octadecadienoic, allcis-9,12,15-octadecatrienoic, allcis-8,11,14-eicostrienoic, allcis-5,8,11,14-eicosatetraenoic, allcis-5,8,11,14,17-eicosapentaenoic and allcis-4,7,10,13,16,19-docosahexaenoic acids were indicative of the less ordered forms reported for sodium oleate at elevated temperature. The diffraction data from the less ordered soaps are consistent with the melted form of the hydrocarbon chains of the unsaturated acids at room temperature.     

Foam performance of fatty acid soaps of odd carbon numbers

The foam capacities, foam stabilities, expanding single bubble stabilities, surfact tensions, and surface viscosities of the straight chain C₉–C₁₄ sodium soaps were measured at various concentration. The C₁₂–C₁₄ soaps, most notably the C₁₃, gave the best over-all foam performance of the compounds studied. The critical micelle concentrations for these soaps were also determined.     

The separation of solid fatty acids from liquid fatty acids by the formation of acid soaps. I. Tallow soaps

The formation of acid soaps has been used successfully for the separation of a mixture of fatty acids into high and low iodine value fractions. The acid soaps of saturated acid can be made to crystallize from water leaving their unsaturated counter parts in solution. Acid soaps of saturated fatty acids are well characterized compounds with the formula R-COOM.R-COOH, where R is a straight alkyl chain, and M is sodium, potassium or ammonium. Optimum crystallization conditions involve a soap concentration of 2–5%, pH adjustment to between 7.0 and 8.0, an initial crystallization temperature not below 25C, and a crystallization period of at least 4 hr during which time cooling to a final temperature of 5–10C must be gradual, and agitation gentle.     

Effect of tallow-coconut fatty acid ratios on properties of bar soaps

In this study, blends of tallow and coconut fatty acids prepared at ratios ranging from 95:5 to 75:25 were converted to sodium soaps, and were processed into soap bars through conventional milling and pressing techniques. Other minor ingredients were included in the bar to protect against rancidity and to provide color. The resulting bars were tested for lather, solubility, penetration, swell, slushing tendency, moisture and cracking. According to one mechanical method, the 85:15 tallow/coconut fatty acid blend yields optimum lather quickness. This does not agree with lather preference by an expert panel which preferred bars with increasing sodium cocoate content or with increasing levels of sodium laurate. Coincident with these effects was an increase in aqueous solubility. However, certain deleterious effects were observed with increase of sodium cocoate, namely: increased slushing and a higher erosion rate.     

Esterification kinetics of glycerol with fatty acids in the presence of sodium and potassium soaps

The kinetics of the direct esterification of glycerol with fatty acids in the presence of sodium and potassium soaps, synthesized in situ to obtain modified acylglycerol emulsifiers, were investigated. The effect of temperature, soap concentration and fatty acid hydrocarbon chain length on the concentration of monoacylglycerols in the reaction mixture was examined. The kinetic studies proved that esterification of glycerol with fatty acids by our method is a first order consecutive reaction with monoacylglycerol as stable intermediate product. The corresponding rate constants and activation energies were evaluated. With the known reaction rate constants, the maximum concentration of monoacylglycerol may be calculated. It was stated that the proposed method opens up possibilities for a specific adjustment of the acylglycerol composition and, thus, of the hydrophilic-lipophilic properties and the characteristics of the emulsifier.     

Foaming properties of rosin soap and their comparison with those of fatty acid soaps

Summary The foam production of soaps made from rosin, modified rosins, and rosin acids were evaluated. The foam production of rosin soaps was compared with soaps made from the individual fatty acids. There was no difference in the foaming properties of soaps made from longleaf and slash pine rosin. Oxidation of the unstable rosin acids in rosin caused the foaming properties of the rosin soap to become more nearly proportional to the concentration. The more hydrogen present in the rosin acid molecule the greater were the foaming properties of the rosin soap. At temperatures between 200° C. and 275° C., the lower the temperature employed for producing pyroabietic acid catalytically, the greater were the foaming properties of the pyroabietic acid soap. There was a difference in the foaming properties of commercial stabilized rosins. In foaming properties the soaps made from rosins, modified rosins, and rosin acids were more like sodium laurate than the other individual fatty acid soaps tested. The author wishes to express his indebtedness to to Dr. G. S. Jamieson and W. G. Rose of the Agricultural Chemical Research Division for the pure lauric, myristic, palmitic and stearic acid used in this study.     

The solubility of sodium and potassium soaps and the phase diagrams of aqueous potassium soaps

Summary Solubility data are provided and collected for the pure sodium and potassium soaps. Hydrolysis obscures the temperatures of solution but is obviated by the presence of a small excess of alkali. Each sodium soap has a large range of temperature between fair and high solubility, whereas the potassium soaps go abruptly into solution, at almost the same temperature and concentration of each soap. The only soaps that are even moderately soluble at room temperature are potassium laurate, myristate, and oleate, the potassium salt of acids from coconut oil, and the sodium oleate. The other sodium and potassium soaps of the saturated fatty acids require elevated temperatures for solution. Phase diagrams for the five commonest potassium soaps are developed and recorded. This work was the basis of a thesis submitted in partial fulfillment of the requirements for the degree of Master of Science, Stanford University, 1947.     

Applications of fatty acids in metallic soaps

Summary In this discussion we have attempted to cover pertinent factors concerning the production and applications of solid fatty acid soaps, with particular emphasis on how the fatty acid characteristics come into play. We have avoided reference to specific formulations because these must be kept in the realm of metallic soap manufacturers’ “know how.” Those interested in modifiers and their effect on metallic soaps can find reference material in past issues of the Journal of American Oil Chemists’ Society (for example, reference 9) and in the patent literature. Reference to theoretical considerations of metallic soap structure has also been avoided as in this area the reader can again find reference material in the Journal of American Oil Chemists’ Society (for example, reference 10).     

Thermal analysis of failed-batch palm oil by differential scanning calorimetry

Thermal behavior of palm oil samples drawn from the batch crystallizers that failed during crystallization and of a control oil that was drawn from a batch that produced good crystallization were analyzed by differential scanning calorimetry under constant heating and cooling conditions. Four polymorphs—β’₂, α, β’₁, and β₁—were observed, and their temperatures were tabulated. A rapid and sudden surge of heat demand was observed for samples from failed crystallizers. Less supercooling values were obtained from the control oil compared to the higher values for samples from failed crystallizers. In crystallization thermograms, a sharp high-temperature exotherm (high-T peak) and a broad low-temperature exotherm (low-T peak) were observed. Low-T peaks were found almost invariably stationary at −5.1 to −5.6°C, and high-T peaks varied depending on the saturation level of the oil. A new peak, sandwiched between the high-T and low-T peaks, was observed for the control oil.     

The prediction of lathering and solubility properties of bar soaps by differential scanning calorimetry

The present differential scanning calorimetry (DSC) study of eight commercial bar soap products has resulted in the assignment of DSC thermal absorptions to three key polymorphic states of soap (also known as“soap phases”): Δ,β,Ω. The DSC data have also been correlated with polymorphic states of soap identified previously by x-ray diffraction (XRD) method. The correlations of quantitative DSC data with consumer-perceived lathering attributes and experimentally determined solubility properties of these bars also are discussed. ¹ Presented at the American Oil Chemists’ Society Meeting, Baltimore, April 1990. *To whom correspondence should be addressed at American Soap Company, Inc., 11170 Green Valley Drive, Olive Branch, MS 38654.     

The solubilization of calcium soaps by fatty acids

The solubilization of the calcium soaps of long chain fatty acids by liquid fatty acids was observed. The solubilities of calcium palmitate, calcium laurate, and calcium oleate were 15.6, 22.8, and 53.3 wt%, respectively, in oleic acid at 40°C. The formation of an acid-calcium soap complex was demonstrated by x-ray diffraction studies of calcium laurate, lauric acid, and a mixture of these compounds that had been heated. Similar evidence was obtained for a calcium oleate-oleic acid complex. The solubility of calcium oleate in a bile salt micellar system was enhanced by obeic acid. The solubilization of calcium soaps by liquid fatty acids may explain the unexpectedly high bioavailability of some calcium soaps.     

Antimicrobial activity of some fatty acid derivatives

Twelve fatty acid amide or ester derivatives were screened for antimicrobial activity against a grampositive bacterium,Staphylococcus aureus; a gramnegative bacterium,Escherichia coli; a mold, eitherAspergillus flavus orA. species; and a yeast, eitherCandida albicans orTorula species. These compounds were adducts of unsaturated fatty derivatives in which the addends were hexachlorocyclopentadiene, thiolacetic acid, bromotrichloromethane, or O,O-diethylphosphorodithioic acid. All of the new compounds appreciably inhibited the activity of at least one of the test organisms, and most of them showed activity against all four types of organisms. The hexachlorocyclopentadiene adduct of 2-(2-ethoxyethoxy)ethyl oleate was especially potent in this regard.     

The fatty acid composition of some entomophthoraceae

Lipids extracted fromConidiobolus denaesporus Drechsl. were found to contain three branched-chain fatty acids, which together comprised about 35% of the total fatty acids of the fungus. The branchedchain acids were identified by gas-liquid chromatography, infrared and mass spectroscopy as 12-methyl tridecanoic, 12-methyl tetradecanoic, and 14-methyl pentadecanoic acids respectively. Then-saturated acids comprise C12, C13, C14, C16, and C18. Then C16,n C18, andn C20 unsaturated acids were also found. The occurrence of 15.2% of myristic acid and of 8.9% of eicosatetraenoic acid provides a further distinctive feature of the lipids ofConidiobolus denaesporus. Contribution No. 94.     

Antimycotic activity of some fatty acid derivatives

Petroselinic and ricinoleic acids and a number of their derivatives, together with stearic acid and two oleic acid derivatives which were in-cluded for the purpose of comparison, have been screened for antimycotic activity against 22 pathogenic yeasts and molds. A number of the compounds exhibited a wide spectrum of activity, testing either fair or good against all or most of the yeasts and molds, and almost all were fairly active against at least one of the organisms. A laboratory of the So. Utiliz. Res. and Dev. Div., ARS, USDA.     

The function of fatty acids in metallic soaps

Conclusion The above consideration of metallic soaps has been conducted from the point of view of the fatty acid used. It is evident that the fatty acid does play an important function in determining the method of preparation, the physical properties, and ultimately the use of metallic soaps. Presented at the annual Fall Meeting, American Oil Chemists’ Society, Nov. 2–4, 1953, Chicago, Ill.     

Tocopherol and fatty acid composition of some Indian pulses

The tocopherol and tocotrienol composition of the Indian pulses Bengal gram (Cicer arietinum L.), blackgram (Vigna mungo L.), green gram (Vigna radiata L.), and horse gram (Dolichos biflorus L.) were studied. The total tocopherol content ranged from 230 to 1567 mg/100 g fat, while the tocopherol content of the pulses as a whole ranged from 6.76 to 12.54 mg/100 g seed. Presence of such a high amount of tocopherol, both in the oil fraction of Indian pulses and in an oil fraction of a food material, is being reported for the first time. The fatty acid composition of the fat extracted from these pulses showed substantial amounts of unsaturated fatty acids (Bengal gram, 88.7%; black gram, 82.9%; green gram, 64.3%; and horse gram, 66.9%). These pulses contained 3.8 to 49.1% linolenic acid in the fat.     

聚马来酸单脂肪醇酯钠盐的制备及其性能研究

将马来酸酐(MA)先聚合为低聚物聚马来酸酐(PMA),然后再与脂肪醇反应生成一种低聚表面活性剂.聚合反应主要受溶剂种类的影响,而酯化方法对酯化反应影响比较大,在丙酮中以三乙胺催化回流制备聚马来酸单脂肪醇酯(PMAM)的较佳工艺条件为:m(丙酮):m(PMA)=2.0:1,反应时间4 h,催化剂用量1.0%(相对于PMA的质量).PMA经脂肪醇改性、烧碱液中和后生成聚马来酸单脂肪醇酯钠盐(PMAMS).产品用IR和GPC进行表征,测定了产品的表面活性数据cmc、?cmc以及乳化力等.     

Mutual solubilities of some fatty acid methyl esters

Mutual solubility data have been obtained for methyl esters of the predominant fatty acids in vegetable oils. Binary freezing point diagrams are presented for systems exhibiting regions of metastable equilibria. Simple eutectic systems were obtained for both saturated-unsaturated and unsaturated-unsaturated methyl ester binary mixtures.     

The insecticidal properties of some fatty acid derivatives

Summary The insecticidal properties of a number of fatty acid derivatives have been investigated, and it was found that certain primary and secondary amines were highly lethal to the common house fly, Musca domestica. Of the primary amines examined, octyl and decyl amine possessed the highest insecticidal activity; however, they were considered to be somewhat irritating for general use. Dioctyl amine was found to be the most active of the secondary amines examined. In view of its exceptionally high paralyzing and killing power for insects and its comparatively non-irritating properties to humans, together with its absence of toxicity to domestic animals, it can be considered as a possible substitute for pyrethrum.     

Preparation and analysis of some food fats and oils for fatty acid content by gas-liquid chromatography

The fatty acid compositions of some food fats and oils were determined by gas-liquid chromatography (GLC) before and after application of reagents and conditions of some extraction procedures. The extraction procedures studied had a nonsignificant effect on the fatty acid compositions. Procedures leading to methyl ester formation through a series of room temp reactions were selected over procedures requiring higher temp reactions, on the basis of yield of products, fatty acid compositions of food lipids of simple composition, or both. These procedures were then used to prepare some food fats and oils for analysis by GLC and the fatty acid compositions determined in this manner are presented. Food Composition Laboratory, ARS, USDA.