Summary
The cis, trans isomers of the conjugated trienes present a difficult problem for complete determination of structure.
Several methods of attack have been outlined, and application of two of them have been made to α and β eleostearic acids, α and β licanic acids, and to pseudoeleostearic acid.
These results indicate the following structures: α eleostearic: cis‐9, trans‐11, trans‐13 β eleostearic: trans‐9, trans‐11, trans‐13 pseudoeleostearic: trans‐10, trans‐12, trans‐14 α licanic: 4‐keto, cis‐9, trans‐11, trans‐13 β licanic: 4‐keto, trans‐9, trans‐11, trans‐13
Summary
Debromination methyl linoleate has been polymerized at 290° and 300° for varying periods, and analysis has been made for monomer, dimer, trimer, normal, and conjugated linoleate.
The disappearance of normal linoleate follows a first order reaction rate with values of K=0.10 hr.−1 at 300° and 0.05 hr.−1 at 290°.
Polymerization of mixtures of normal and conjugated linoleate indicate that dimer may be formed by their reaction with each other.
The value for K, the first order reaction velocity constant for disappearance of normal linoleate, decreases to a limiting value on dilution with methyl stearate. This limiting value is about one‐fourth that obtained on undiluted linoleate.
The above facts are qualitatively explained by assuming that the mechanism of dimerization of normal linoleate is extensively: N»C relatively slow N+C→D relatively rapid.
Summary
Methyl eleostearate has been thermally cyclized in good yields, and a concentrate of the cyclic product has been prepared.
Using small amounts, a technique has been devised for a) aromatization of the resultant cyclohexadiene, b) oxidation to orthophthalic acid, and c) characterization of the acid as the anhydride and the imide.
The significance of cyclic fatty acids in industrial processes is discussed.
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