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Volume 38, 1905
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Experimental.

The anilides and toluidides described in the present paper were prepared by the following method: A mixture of from 1 to 3 grams of the fatty acid and the equivalent amount of aniline or paratoluidine was sealed in a tube and heated to 150°–180° for eight hours. In no case was any pressure observed in the tube after cooling. The product obtained in this manner was treated several times with dilute hydro-

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chloric acid to separate any uncombined base. After this the impure substance, which if it had first separated as an oil had in most cases now become solid, was washed with water and crystallized from dilute alcohol. Usually three crystallizations were sufficient to obtain a compound of constant melting-point. The yield was in general 50–80 per cent. The purified compound was then analysed by determining the percentage of nitrogen by the ordinary method of Dumas.

The following are the details of the experiments:—

Nonylanilide: C15H28ON; white crystals; M.P., 57°. On analysis, 0·2140 gram gave 11·7 c.c. N at 23°, and 768 mm. N = 6·3 per cent., (calc.) 6 per cent.

Decanilide: C16H25ON; white crystals; M.P., 61°. On analysis, 0·1098 gram gave 5·7 c.c. N at 22°, and 758 mm. N = 5·9 per cent., (calc.) 5·7 per cent.

Undecylanilide: C17H27ON; white crystals; M.P., 64°. On analysis, 0·1968 gram gave 9·6 c.c N at 23°, and 768 mm. N = 5·6 per cent., (calc.) 5·3 per cent.

Lauranilide: C18H29ON; light-yellowish crystals resembling lauric acid; M.P., 68°. On analysis, 0·3376 gram gave 14·6 c.c. N at 20°, and 770 mm. N =5·1 per cent., (calc.) 5·0 per cent.

Butyroparatoluidide: C11H15ON; white crystals; M.P., 74°. On analysis, 0·1502 gram gave 10·3 c.c. N at 23°, and 764 mm. N = 8·0 per cent., (calc.) 7·8 per cent.

Valeroparatoluidide: C12H17ON; white crystals; M.P., 72°. On analysis, 0·1474 gram gave 9·6 c.c. N at 19°, and 750 mm. N = 7·5 per cent., (calc.) 7·3 per cent.

Hexoparatoluidide: C18H19ON; white crystals; M.P., 75°. On analysis, 0·2194 gram gave 13·4 c.c. N at 22°, and 754 mm. N = 7·0 per cent., (calc.) 6·8 per cent.

Heptoparatoluidide: C14H21ON; white crystals; M.P., 80 per cent. On analysis, 0·2560 gram gave 14·2 c.c. N at 22°, and 756 mm. N = 6·3 per cent., (calc.) 6·4 per cent.

Octoparatoluidide: C15H23ON. Separated as a brown oil, which crystallized only after several weeks. After four recrystallizations a small quantity of the compound, melting constantly at 59°, was obtained. The amount was insufficient for analysis. The small yield in this case is probably due to the fact that it is extremely difficult to prepare octoic acid in a pure state.

Nonylparatoluidide: C16H25ON; white waxy crystals; M.P., 81°. On analysis, 0 1962 gram gave 9·8 c.c. N at 21°, and 754 mm. N = 5·7 per cent., (calc.) 5·7 per cent.

Decoparatoluidide: C17H27; whitish crystals; M.P.,

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80°. On analysis, 0·1646 gram gave 8 0 c.c. N at 23°, and 756 mm. N = 5·5 per cent., (calc.) 5·3 per cent.

Undecylparatoluidide: C18H29ON; waxy white crystals; M.P., 67°. On analysis, 0·1924 gram gave 8·5 c.c. N at 23°, and 758 mm. N = 5·0 per cent, (calc.) 5·0 per cent.

Lauroparatoluidide: C19H31ON; yellowish crystals; M.P., 81°. On analysis, 0·2780 gram gave 12·1 c.c. N at 22°, and 756 mm. N = 5·0 per cent., (calc.) 4·8 per cent.

Myristoparatoluidide: C21H35ON; waxy white crystals; M.P., 93°. On analysis, 0·2042 gram gave 7·6 c.c. N at 21°, and 760 mm. N = 4·35 per cent., (calc.) 4·4 per cent.

Palmitoparatoluidide: C23H89ON; yellowish crystals; M.P., 96°. On analysis, 0·2618 gram gave 9·2 c.c. N at 21°, and 764 mm. N = 4·1 per cent., (calc.) 4·05 per cent.

Stearoparatoluidide : C25H48ON; after six crystallizations from absolute alcohol the compound melted at 90°. On analysis, 0·2710 gram gave 9·0 c.c. N at 22°, and 764 mm. N =3·9 per cent., (calc.) 3·75 per cent.