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.     

Homo-and copolymers of vinyl esters,acrylates, and methacrylates of some derivatives of fatty acids

Vinyl esters of some undecylenic acid derivatives and acrylates and methacrylates of undecyl and undecylenyl alcohols, which may be considered as derivaties of castor oil, have been polymerized and copolymerized with vinyl chloride to provide a variety of new polymers. The acrylate and the methacrylate of undecylenyl alcohol have been epoxidized to yield two new polymerizable monomers of potential usefulness as crosslinking agents in finished copolymers.     

Long-chain fatty acids containing ether linkage. I. The antibacterial and fungicidal activities of some new β-alkyloxypropionic acids and their methyl esters

β-Alkoxypropionic acids and their methyl esters were made with alkoxy groups ranging from C₄H₉O to C₁₈H₃₅O: R-O-CH₂CH₂COOH (CH₃). Methyl esters and acids were also made with one and with two oxyethylene groups between the alkoxy group and the propionic acid group: RO (CH₂ CH₂ O) n-CH₂CH₂ COOH(CH₃). The compounds were tested againstStaphylococcus aureus and againstPenicillium for growth inhibition. The optimum size of the alkoxy group appears to be R=C₁₂H₂₅. Oxyethylene groups enhanced the activity againstS. aureus, but had relatively little effect againstPenicillium.     

Studies on the fungicidal properties of some organo-tin compounds

The results of an investigation into the fungicidal properties of some bi-functional organo-tin compounds containing mono- and dithiocarbamate ligands are reported. These experiments were conducted against a number of soil and plant pathogenic fungi. While all the compounds examined proved to be powerful fungicides, differences at the concentration levels tested were not sufficiently significant to relate degree of toxicity to ligand structure. Comparison between the fungicidal activity of the di-and triphenyl-tin compounds is in agreement with earlier observations that the latter are more toxic than the former.     

Nitrogenous derivatives of cyclic fatty acids

A number of nitrogenous derivatives of cyclized acids derived from C-18, triene-containing fatty acid sources, were prepared. Mixed amides (mp 33C), nitriles (fp −25C), and amines (fp −34C), prepared from the hydrogenated cyclic acids, have uniquely low mp for fat-derived substances of their mol wt. Compatibility with synthetic resins and solubility in organic solvents of the mixed amides are high compared to common fatty-amide mixtures. The nitriles and morpholides are compatible with polyvinyl chloride and may have potential as plasticizers for it. The hydrogenated cyclic fatty acid amines have an approximate fp of −34C. The diethanolamides, ethenoxylated amides, and quaternary amines were prepared and their surface-active properties compared with similar fat-derived substances. Presented at AOCS meeting in St. Louis, Mo., 1961. A laboratory of the Northern Utilization Research and Development Division, Agricultural Research Service, U.S.D.A.     

New applications for fatty acids and derivatives

The early development of the American fatty acid industry during 1900–1920 is usually associated with the use of stearic acid in candles for lighting purposes. Today, the use of stearic acid in candle manufacture continues; the volume consumed for this application is not small, but the use is for ornamental, decorative or festival purposes, only incidentally for emergency lighting purposes. When one consideres that most condles consist of 10–20% stearic acid, which improves among other things, the appearance, burning qualities and stiffness of the candle, the volume consumed is appreciable. More than that, the growth rate in this use is impressive. In 1965, it has been estimated that the volume of double-pressed stearic acid that found its wya into candles was 3.5 million pounds. Today (1979) it is conservatively estimated that from 10–12 million pounds are utilized for this purpose. Innovations, such as the development of driples candles, achieved by the incorporation of a somewhat larger proportion of stearic acid to the external wax coat, are now possible uses. Concrete and asphalt are examples of much-used large tonnage materials of construction which have disadvantages in use that can be at least partially or significantly improved through the incorporation of stearic acid or certain other fatty chemicals. An excellent example of the tailor-making of fatty acid derivatives to satisfy an almost desperate need is provided by the development of derivatives suited for the retardation of water evaporation from reservoirs in arid areas. In 1966 it was estimated that the evaporation from large lakes and reservoirs in 17 western states was equivalent to 14 million acre feet, an amount which could ordinarily supply 84 million people annually. The design of water insoluble long chain organic compounds with a hydrophilic group at one terminal position gives products capable of forming monomolecular films which are uniquely suited to solve this problem. Fatty alcohol ethoxylates are only one approach among several. Paper presented at Short Course by S. Eng, Glyco Chemicals, Inc., Painesville, Ohio Representatives of A. Gross Candle Co. (Linden, NJ), Faroy, Inc. (Houston, Texas) and Old Harbor, Inc. (Hyanis Port, MA) supplied part of the information used in this paper.     

Branched chain fatty acids and sulfonated derivatives

Several 2-alkyl fatty acids containing 18–21 carbon atoms, were synthesized by tertiary butyl peroxide catalyzed addition of linear aliphatic carboxylic acids to normal terminal olefins. The products obtained in 35–70% yields were purified by fractional distillation. The acids were sulfonated with sulfur trioxide dioxane adduct and isolated as the disodium salts in 60–80% yields.

$$ \begin{gathered} R - CH_2 CO_2 H + R'CH = CH_2 \xrightarrow[{125 - 160C}]{{Perioxide}}R'CH_2 CH_2 - CH(R)CO_2 H \hfill \\ R' - CH_2 CH_2 CH(R)CO_2 H + SO_3 \xrightarrow{{CCl_4 }}R'CH_2 CH_2 C(SO_3 H)(R)CO_2 H \hfill \\ \end{gathered} $$     

Solubilities of fatty acids and derivatives in acetone

Summary An improved “synthetic” method of determining solubilities has been described which combines simplicity with accuracy. Saturated fatty acids with even numbers of carbons from C₆ to C₁₈ and oleic, linoleic, and linolenic acids, their methyl esters, their simple triglycerides and their corresponding alcohols have been prepared in purified form. The solubilities in acetone of their most stable forms have been determined from ordinary room temperatures down to about −70°C. or to temperatures where they are only slightly soluble. The precipitation of unstable polymorphs from solutions was observed in the case of palmityl alcohol. Hormel Institute Publication No. 159, a report of work done under contract with the U. S. Department of Agriculture and authorized by the Research and Marketing Act of 1946. The contract has been supervised by the Eastern Utilization Research Branch of the Agricultural Research Service.     

Physical properties of fatty acids

Summary The chemical composition, molecular configuration, and crystal structure of fatty acid molecules contribute to the more than twenty distinct physical properties associated with this class of organic compounds. This discussion will be limited to only a few of these fatty acid properties and will include melting and solidification phenomena, vapor pressure-boiling point relationships and solubility behavior of fatty acids.     

Preparation and properties of some polyglycerol esters of short and medium chain length fatty acids

Mono- and diesters of the short and medium chain acids were prepared with polyglycerols and compared with their corresponding mono- and diglycerides. The physical and chemical properties of such partial esters of polyglycerols, particularly with respect to their oil, water and solvent solubility are given. Polyglycerol esters become more hydrophilic as the molecular weight of the polyol increases. Polyglycerol esters become less hydrophilic as the length of the aliphatic chain of the acid used in esterification is increased. Polyglycerol esters of such short and medium chain fatty acids show promise in applications where surface activity and emulsification, solubilization of oil and water systems is desired. Presented at the AOCS Meeting, New York, October 1968.     

Cyclopinolenic acids: Synthesis,derivatives and thermal properties

The two isomeric cyclopinolenic acids (CP-1 and CP-2), components of distilled tall oil, have been synthesized by means of an intramolecular Diels-Alder reaction of isomers of 5,10,12-octadecatrienoic esters, themselves synthesized in a stereocontrolled manner. The 5cis,10-trans,12trans isomer cyclizes at 200°C to a 1:3 mixture of esters of CP-1 and CP-2. At 200°C, the 5cis,10trans,12cis isomer is unreactive, but at 240°C it gives the same CP-1 + CP-2 ester mixture, presumably by way of prior isomerization to the 5cis,10trans,12trans isomer. A subambient thermal study of CP-1 and CP-2 and their derivatives shows that the compounds, excluding CP-1, lack crystalline structures or melting points, and display glass transitions only, below −80°C for esters and below −50°C for the carboxylic acids.     

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.     

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.     

Component fatty acids of some cruciferae oils

Summary The oils from yellow mustard seed (Brassica alba), black mustard seed (Brassica nigra) of Indian origin, and rapeseed (Brassica Compestris) of unknown origin have been analyzed for their fatty acid composition without preliminary resolution of fatty acids by lead-salt-alcohol or fractional crystallization methods. The results compare very favorably with those determined by other recently developed methods. It may be concluded therefore that this method can be favorably employed for the determination of fatty acid composition of fats containing higher unsaturated acids. Confirmatory evidence has been obtained for the presence of eicosenoic acid in rapeseed oil. The nature and amount of fatty acids of yellow mustard seed oil of Indian origin do not differ in any significant manner from those of other cruciferous seed oils. The present analysis of black mustard seed oil reveals a higher amount of linolenic acid, and the presence of a C₂₀ monoethenoid acid, not heretofore reported. Contribution No. 708 from the Department of Chemistry, University of Pittsburgh. Presented in part at the Spring meeting of the American Oil Chemists’ Society, held in New Orleans, La., May, 1948. Baliga and Hilditch’s paper. “The Component Acids of Rapeseed Oil” (J. Soc. Chem. Ind.67, 258–262 (1948).