The Geometric Isomerism of the Linolenic Acids. Elaidolinolenic Acid<sup>1</sup>

Kass, J. P.; Nichols, Joseph; Burr, George O.

doi:10.1021/ja01849a047

Cited by 19 publications

(4 citation statements)

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“…A simplified interpretation of the 1,4diene mechanism for the polymerization of the conjugated trienoic acids is presented, Ethyl elaidolinolenate was prepared according to the procedure of Kass et al (9). The iodine number was 244.1; n3£, 1.4634; d\°, 0.8775.…”

Section: Esters Of Isomeric Fatty Acidsmentioning

confidence: 99%

Polymerization of Drying Oils

Cowan¹,

Wheeler²,

Teeter³

et al. 1942

Ind. Eng. Chem.

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Section: Esters Of Isomeric Fatty Acidsmentioning

confidence: 99%

Polymerization of Drying Oils

Cowan¹,

Wheeler²,

Teeter³

et al. 1942

Ind. Eng. Chem.

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“…Comparison of the hexabromide numbers of debromination and crystallization linolenic acids as obtained by the authors' procedure indicates that an even greater degree of isomerization occurs during the debromination of a-hexabromostearic acid than suggested by Brown and co-workers (6). Confirmation of the higher hexabromide number of natural linolenic acid thus further requires the modification of Rollett's conclusion (9) of the formation in equal proportion of four pairs of isomeric hexabromides from that unsaturated acid, his fundamentally correct hypothesis having been based on the observation of the fortuitous behavior of the nonhomogeneous debrominEftion linolenic acid (4). Final solution of the exact degrees of isomerization and proportions of bromides formed awaits the unquestionable purification of linolenic acid to proved identity with the natural form and the development of a method for the determination of true hexabromide numbers, since the present study may be claimed to have brought out only correct minimal values, having disregarded such effects noted by Steele and Washburn (11) as the increased hexabromide numbers observed in the presence of traces of alcohol or acetone in the solvent.…”

Section: Discussionmentioning

confidence: 92%

Study of Hexabromide Number

Kass¹,

Roy²,

Burr³

1947

Anal. Chem.

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“…29-30°C.) was prepared according to Kass, Nichols, and Burr (12). The a-and /3-eleostearic acids were isolated from tung oil (18).…”

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A Monolayer Study of the Isomerism of Unsaturated and Oxy Fatty Acids.

Schneider¹,

Holman²,

Burr³

1949

J. Phys. Chem.

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Monomolecular films of fatty acids on water solutions have been studied extensively and have been found to show properties related to the molecular structure of the fatty acids (1). The force-area curves of monolayers indicate the apparent cross-sectional area of the molecules in the film, and their shapes differ one from the other dependent upon intermolecular forces, which in turn are an expression of the molecular structure. Studies of monolayers of some unsaturated fatty acids have been made (1, 3, 9, 16), but a systematic comparison of the monolayers of isomers of unsaturated fatty acids, including conjugated and nonconjugated polyunsaturated acids, has hitherto not been carried oui. Such a study of isomers of unsaturated acids could conceivably give more information as to the effects of isomerism upon the packing of molecules in a monolayer and, conversely, could perhaps offer evidence regarding the structure of tarty acids whose structure is not definitely known.Inasmuch as a group of oxy fatty acids were available for study, it .-eemed also of interest, as a basis for the study of the oxidation of unsaturated fatty acids in monolayers, that the force-area curves of these be investigated. Some of these substances also afford further opportunity for the study of the effect of isomerism upon monolayer characteristics. EXPERIMENTAL Monolayers were spread on Ay 100 sulfuric acid containing 0.12 per cent hydroquinone in a Langmuir hydrophil balance supplied by the Central Scientific Company. The films were spread from dilute solutions of the fatty acids in redistilled petroleum ether (b.p. 45°C.) except in the cases of /3-licanic acid, diketostearic acid, and rieinelaidic acid, for which redistilled c.p. thiophene-free benzene was used as solvent. The solutions were expelled onto the water surface from a calibrated 0.5-ml. syringe having a stationary back-stop. All experiments were run at room temperature, and with each substance tested, a sample of stearic acid was run as a standard. The limiting areas were corrected assuming that• of stearic acid to be 24.4 A.', as found by Nutting and Harkins (201 -The experimental data are taken from a thesis submitted to the Graduate School of the University of Minnesota by V. Lorraine Schneider in partial fulfillment of the requirements for the degree of Master of Science in 1946.

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The Geometric Isomerism of the Linolenic Acids. Elaidolinolenic Acid¹

Cited by 19 publications

References 0 publications

Polymerization of Drying Oils

Polymerization of Drying Oils

Study of Hexabromide Number

A Monolayer Study of the Isomerism of Unsaturated and Oxy Fatty Acids.

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The Geometric Isomerism of the Linolenic Acids. Elaidolinolenic Acid1

Cited by 19 publications

References 0 publications

Polymerization of Drying Oils

Polymerization of Drying Oils

Study of Hexabromide Number

A Monolayer Study of the Isomerism of Unsaturated and Oxy Fatty Acids.

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Product

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The Geometric Isomerism of the Linolenic Acids. Elaidolinolenic Acid¹