Fatty oxazolines and imidazolines

Fatty acids are converted, almost quantitatively, into oxazolines by reaction with 2‐methyl‐2‐aminopropanol. These oxazolines are of high purity. They can be reacted further with paraformaldehyde to yield a mixture of mono‐ andbis‐methylol derivatives in the α‐position. Heating causes dehydration to form α‐methylene oxazolines, which on hydrolysis provide good overall yields of α‐alkylacrylic acids. Substituted anilides of the acrylic acids possess substantial antibacterial properties against Gram‐positive microorganisms. The reaction of two moles of fatty acid with one of diethylenetriamine yields a primary amine with the structure of RCON(CH2CH2NH2)CH2CH2NHCOR, instead of a secondary amine as reported in the literature. Imidazoline is also formed. Removal of water by vacuum results in almost quantitative ring closure. The unquaternized imidazolines are highly unstable to hydrolysis and will revert to the above diamido amine at room temperature. Open‐chain compounds are more water repellent than the imidazolines. Repellency of the saturated fatty acid derivatives increases with increasing molecular weight. Unsaturation decreases repellency, particularly for thecis derivative, whereas thetrans derivative (from elaidic acid) possesses better repellent properties. Branching of the alkyl chains is also detrimental to water repellency. Application of repellents to soil dramatically reduces water absorption and seed germination.