Pelargonic acid, 288 Table

The reactions of thionyl chloride and phosphorus halides, also in their polymer-modifled form, involve the formation of hydrogen halide and cannot, therefore, be applied without complications to acid sensitive compounds. The combination of triphenylphosphine and tetrachloromethane as reagent provides conditions under which, for instance, pelargonic acid can be converted to the acid chloride in good yield according to equation (5). ° This method has been recently applied to polymer-bound triphenylphos-phine. Table 2 lists some examples of acids treated in this manner. 

The peptide circulin, which was isolated from a culture of Bacillus circulans (431) should be placed in the polymyxin group. This antibiotic, active preferentially on Gram-negative bacteria (430) is a cyclic, basic heteromeric peptide, containing, as do polymyxins, L-a,7-diaminobutyric acid, threonine, and an optically active isomer of pelargonic acid which is probably (-b)6-methyloctanoic acid. In addition, circulin contains D-leucine (458). The composition (Table IX) of circulin is close to that of polymyxins A and E. However, this antibiotic, unlike polymyxin A, is inactivated by the enzyme lipase (458). Paper chromatography (173) distinguishes circulin from polymyxins A and E. 

Some of the more prominent carboxyhc acids that are not fat- or oil-based include acetic, acryUc, and olefin-based propionic, butyric/isobutyric, 2-ethylhexanoic, heptanoic, pelargonic, neopentanoic, and neodecanoic. Table 1 summarizes the production, pricing, and primary producers of these acids. 

Nonanoyl morpholide—pelargonic morpholide or EA 1778—is a fatty acid amide with a molecular weight of 227 and a boiling point of 120-130°C at 0.5 mm Hg (see Table 4-1). Classed as a pungent, because of Its pungent odor, It Is chemically related to alkaloids found In black pepper.1 3 4 it8 synthesis has been described by Rice et al.3... 

Vinyl caproate, caprylate, pelargonate, caprate, myristate, pahnitate, stearate, 10-hendecenoate (undecylenate) and oleate can be prepared in a similar manner, except that in the preparation of the pahnitate and stearate the fatty acids are added to a solution of mercuric acetate and sulfuric acid in vinyl acetate. Vinyl stearate is not redistilled, but the once-distilled product is recrystallized from acetone at 0° (3 ml. of acetone per gram of vinyl stearate). The amount of mercuric acetate employed was 2%, and the amount of 100% sulfuric acid was 0.3-0.4%, of the weight of the stearic acid. Average yields and properties of these vinyl esters are given in the table. 

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