Über die Herstellung der Imidazoline von Fettsäuren

Preparation of Imidazolines of Fatty Acids The formation of imidazolines was studied in the reaction of diethylene triamine with fatty acids and oils. With the aid of IR- and UV-spectroscopy, it could be proved that imidazolines are formed at temperatures between 150° - 200° C. Aminoamides are also formed at these temperatures. Above 280° C, decomposition takes place, and low molecular nitrogen compounds, including probably ammonia, are formed.     

Untersuchungen über die Entstehung von Kohlenwasserstoffen in UV-bestrahlten Fettsäuren und Fettsäure-Estern

Studies on the Formation of Hydrocarbons in Fatty Acids and Fatty Acid Esters Irradiated with UV Rays The investigation of volatile compounds in unsaponifiable matter and in steam distillates of UV-irradiated saturated fatty acids and fatty acid esters has shown that by irradiation in the presence of air as well as under vacuum, along with other substances, unsaturated hydrocarbons are formed. They are most probably 1,2 alkenes whose chains are shorter than the corresponding fatty acids by 2 C-atoms. The volatile compounds in the unsaponifiable matter of the UV-irradiated oleic acid comprise predominantly of carbonyle compounds.     

Über die Struktur cyclisierter Fettsäureester

The Structure of Cyclised Fatty Acid Esters It is proved that the cyclic fatty acids which are obtained from tung and linseed oils by alkali-treatment contain mainly two types of products. Approximately 30% of these consist of 1,2-disubstituted cyclohexadiens, whose one double bond of the ring is in the 1-position and the other one is conjugated to the former. Approximately 60% of the mixture is comprised of ω-(2-alkyliden-cyclohexenyl)-fatty acid esters. The double bond in the ring is predominantly in the 3-position. As a result of the rearrangement of double bonds before cyclisation, R′varies from C₂ to C₁₁ and R″ from C₀ to C₉.     

Über den Einfluß der Begleitstoffe der Fettsäuren auf die Kinetik ihrer Hydrierung

Ta Influence of Concomitant Substances of Fatty Acids on the Kinetics of their Hydrogenation In the present paper the influence of concomitant substances of animal fats and their degradations components on the kinetics of the hydrogenation of free fatty acids of these fats was investigated. Our attention was directed to the balance of organic sulphur, phosphor and nitrogen compounds during high pressure splitting of fats, distillation of fatty acids and following hydrogenation. During the splitting process 70% of nitrogen and sulphur containing substances were degradated or removed, the content of phosphor containing substances didn't change basically. Another decrease of concomitant substances and their splitting products occurs during distillation of fatty acids. In the subsequent hydrogenation the content of phosphor containing compounds decreased significantly. Residual contents of amino acids and sulphur compounds were absorbed by the Ni-catalyst and contributed to the decrease of its activity. The effect of the confirmed substances on the decrease of its activity. The effect of the concomitant substances on the decrease of the hydrogenation velocity was confirmed by their addition to the fatty acids of sunflower oil after chromatographic isolation. This addition (concentration from 1 to 3%) lowered the reaction velocity up to 50%.     

Untersuchungen über die Entstehung von Kohlenwasserstoffen in erhitzten gesättigten Fettsäuren und Fettsäureestern

Studies on the Formation of Hydrocarbons in Fatty Acids and Fatty Acid Esters on Heating The investigations on the volatile compounds of the unsaponifiable matter and the steam distillate of heated saturated fatty acids have shown that on heating in the presence of air, along with other substances, hydrocarbons having a chain length 1 to 2 C atoms shorter than the corresponding fatty acids are formed. The splitting proceeds so slowly in the case of esters that even after 4 hrs of heating at 160°C no reaction products could be detected. By heating palmitic acid under the same conditions, except that vacuum was employed, no perceptible quantities of hydrocarbons were found.     

Über Sorptionsvorgänge von Carbonsäuren an Haarkeratin

The Sorption Process of Carboxylic Acids on Hair Keratin Methods for the measurement of adsorption of carboxylic acids by hair keratin were worked out. The different methods show good agreement in their results. The adsorption of monochloroacetic acid was determined in relation to its concentration, time of action and pH value. Also the adsorption of homologous and variedly substituted carboxylic acids from aqueous as well as absolute propanol solutions was compared to each other. For the adsorption of carboxylic acids by hair keratin, the dissociation, chain length, substitution and solvent are of utmost importance.     

Vergleichende Untersuchungen über die Wirkung von Antioxidantien,Aminosäuren und Casein auf die Autoxidation ungesättigter Fettsäuren

Comparative Investigations of the Effect of Antioxidants, Amino Acids and Casein on the Autoxidation of Unsaturated Fatty Acids The antioxidants α-tocopherol and ascorbyl palmitate (AP), the amino acids histidine and methionine as well as casein were added to emulsions of methyl linoleate (ML) in water, and the influence of these components on autoxidation of ML was determined by measuring the rate of oxygen uptake using the Warburg method. The monohydroperoxides of ML being the primary autoxidation products were analyzed by HPLC; hexanal being their main fragmentation product which essentially contributes to rancidity of foods was determined by head space gas chromatography. α-Tocopherol on the one side acts as a radical scavenger by its hydrogen donating effect discernible by a high ratio of cis/trans- to trans/trans-isomers of the ML-hydroperoxides, on the other side it stabilizes these intermediary products thus inhibiting the formation of hexanal. In the presence of Fe(II)-ions AP has a prooxidative effect by causing a rapid decomposition of hydroperoxides, whereas in the initial oxidation phase histidine and methionine have no or only a minor antioxidative effect which increases later on, connected with an inhibitory effect on peroxide decomposition creating hexanal. During ML autoxidation the different components added to the ML emulsion including methionine bound in the casein, which has a strong antioxidative effect, were also oxidized.     

Über den Einfluß von Sonnenblumen-Krankheiten auf das Samenöl und auf die Veränderungen der freien Fettsäuren

Influence of Sunflower Diseases on the Seed Oil and on Changes in Free Fatty Acids The relationships between the widespread sunflower diseases like peronospora, botrytis disease, etc. on reduction of yield as well as on the deterioration of the quality of oil were investigated. It can be seen from the results obtained that the damage caused by such diseases can be minimized by suitable measures like dressing of the seeds, appropriate nutrition, proper sequence of planting etc. However, the breeding of resistant varieties remains an important task. Promising results were obtained in this respect by the author on the basis of an artificial infection procedure carried out in pathological breeding grounds.     

Bestimmung von cyclischen Fettsäuren über eine Harnstoffsäule

Determination of Cyclic Fatty Acids on Urea Column Cyclic monomeric fatty acids (CFA) in the mixture of straight chain saturated and unsaturated fatty acids were determined after methylation (CFA-Me) as non-adducts on an urea column. The method gives quantitative results with mixtures containing 5% or more of cyclic fatty acids. The determination is easy and rapid.     

Über den Reaktionsmechanismus der Bildung von Fettsäure-methylestern

Reaction Mechanism in the Formation of Methyl Esters of Fatty Acids The studies showed that methyl esters of fatty acids are formed exclusively in the hydrolysis of fats under definite conditions of reaction. Methyl esters are formed within a few seconds by treating triglycerides with alkaline methanol in homogeneous phase. If mineral acids are used as catalysts, the formation of esters from fatty acids and methanol is very rapid even at low temperatures. The author has reported two rapid methods for preparation of methyl esters of fatty acids which are especially suited for esterification and gas chromatographic investigation of polyenoic fatty acids.     

Regioselektive C-H-Funktionalisierung von Fettsäuren und Fettsäuremethylestern

Regioselective C-H-Functionalization of Fatty Acids and their Methyl Esters Fatty acids and thier methyl esters can be chlorinated preferentially at the terminal methylene groups with N-alkylchloroamines in sulfuric acid. With capric acid and its methyl ester the optimal reaction conditions for the selective chlorination were elaborated and then transferred to longer fatty acids up to stearic acid. The influence of the solvent, the temperature and the nature of different chlorinating reagents on the selectivity was studies. The capillary GC/MS-analysis of the isomeric chlorinated fatty acids is described.     

Über die Darstellung isomerenfreier verzweigter Carbonsäuren

Preparation of Branched Carboxylic Acids Free from Isomers A method for the preparation of branched saturated and unsaturated carboxylic acids, free from isomers, from tertiary γ-lactones by means of alkyl aluminium chlorides is reported. Saturated branched carboxylic acids were obtained in high yields by the reaction with ethyl aluminium chloride, whereas the reaction with diethyl aluminium chloride yielded the unsaturated acids. Splitting of lactones with mixtures of both the ethyl aluminium chlorides gave mixtures of saturated and unsaturated acids. The structure of the unsaturated carboxylic acid was determined by hydrogenation, ozonolysis, iodine value and gas chromatography.     

Über lipotrophe Hefen auf der menschlichen Haut und deren Bedarf an bestimmten Fettsäuren

Lipotropic Yeasts of the Human Skin and their Requirement for Definite Fatty Acids Pityrosporum species can often be isolated from the skin. Their pathogenetic significance is disputed. P. orbiculare and P. ovale differ from each other by their requirement on fatty acids. Oleic acid can be utilized only by P. ovale, whereas myristoleic and palmitoleic acids only by P. ovale, whereas myristoleic and palmitoleic acids only by P. orbiculare. Within the genus P. ovale the individual varieties can be differentiated, for instance, one variety utilizes lauric, myristic, palmitic and stearic acids, another variety only the first three of the said acids and a third one, which utilizes only myristic acid. The different species are sensitive against antimycotica to variable extent.     

Über die Autoxydation gesättigter Fettsäuren IV: Sauerstoff-Verbrauch und Bildung von Peroxiden bei der Oxydation von Laurin- und Stearinsäure sowie ihrer Methylester

Autoxidation of Saturated Fatty Acids IV: Oxygen Consumption and the Formation of Peroxides in the Oxidation of Lauric and Stearic Acids and their Methyl Esters The investigation showed a reproducible course of oxygen uptake and peroxide formation. In the oxidation of free acids the oxygen uptake was considerably higher than the corresponding peroxide content. The amounts of peroxides determined are so small that secondary reactions may be assumed to occur at relative ease under the experimental conditions. The higher content of peroxide compounds in the oxidation of methyl esters compared to that in the oxidation of free acids indicated a hindrance of the subsequent reactions which are associated with the decomposition of the peroxides. The experiments showed that initially an unusually large part of the absorbed oxygen is consumed in the formation of peroxides. The formation of split products can therefore occur here only with great difficulty in contrast to the case of free acids.     

Über die Fettsäurezusammensetzung der Lipoide einiger Gewürze

Fatty Acid Composition of Lipids of Some Spices Fatty acid composition of lipids of ten fruit spices (pepper, pimento, red pepper, chillies, cumin-seed, coriander, celery, dill, cardamon and vanilla), one seed spice (nutmeg), one flower spice (clove), three herb spices (sage, origano, thyme), one leaf spice (laurel), one bark spice (cinnamon) and ginger was determined by gas chromatography after transesterification and compared with the known values. In the lipids of cardamon, vanilla, cinnamon, ginger and laurel, which have not been examined so far, palmitic, oleic and linoleic acids were found to predominate. In the lipids of pimento and clove which belong to the family of myrtaceae, C₁₈ fatty acids were predominant. Spices belonging to the family of labiates are characterized by a high linolenic acid content.     

Wasserstofferzeugung für die Hydrierung von Fetten und Fettsäuren

Production of Hydrogen for the Hydrogenation of Fats and Fatty Acids A process is described for the production of highly pure hydrogen from hydrocarbons, such as natural gas, liquefied gas and light petroleum. The process consists of following three steps: 1. Desulfurization of the starting material; 2. Conversion of hydrocarbons into permanent gases by splitting with steam at high temperatures; 3. Separation of other gases from hydrogen by adsorption. This process has been tested commercially. With increasing cost of transport, and owing to regulations for the transport of hydrogen, which are difficult to fulfil, the aforesaid process offers an attractive alternative to the consumer of hydrogen. Cost of investment, energy consumption and economy of the process are dealt with.     

Untersuchungen über die Struktur dimerer Fettsäuren V: Thermische und peroxidkatalysierte Dimerisierung von Linolensäure-methylester

Investigations on the Structure of Dimeric Fatty Acids V: Thermal and Peroxide-Catalyzed Dimerisation of Methyl Linolenate By heating methyl linolenate at 280° C in high vacuum 26% dimers resulted besides 2% hydrocarbons, 24% methyl esters of monocarboxylic acids, 46% polymers and methyl esters of dicarboxylic acids. The dimers comprise of mainly penta-, tetra-, tri- and bicyclic types. Dehydro dimers obtained by catalytic action of di-tert-butyl peroxide on methyl linolenate at 140° C were mainly of the acyclic type containing 6 double bonds.     

Einfluß der Konfiguration der Fettsäuren auf die Eigenschaften von Seife

Effect of Fatty Acid Configuration on the Properties of Soap The effect of configuration of the hydrophobic chain of fatty acids C₁₀–C₁₈ on the properties of their alkali salts was studied. Furthermore, the effect of temperature on critical micelle concentration (CMC) and on alteration of surface tension at CMC, as well as the effect of chain length of the hydrophobic part on CMC were determined. At the same time, the effect of double and cis-trans configuration on CMC was studied. Also the foaming ability of the individual soaps and foam stability as well as the stability of the soaps were investigated.