This section is from the book "Alcohol, Its Production, Properties, Chemistry, And Industrial Applications", by Charles Simmonds. Also available from Amazon: Alcohol: Its Production, Properties, Chemistry, And Industrial Applications.
This is produced by heating equimolecular quantities of aniline hydrochloride and ethyl alcohol to 180° in an autoclave, as with the corresponding methyl compound. On cooling, the ethylaniline hydrochloride formed crystallises out, and can thus be separated.
1 Compt. rend., 1918, 168, 467-469. 2 Ibid., 564-566.
Ethylaniline boils at 206° and its sp. gr. at 15°/15° is 0.964. It has not much technical application.
Diethylaniline, C6H5N(C2H5)2, is obtained by heating the requisite proportions of aniline hydrochloride and alcohol under pressure, but is not readily procured completely free from the monoethyl compound. It is a liquid, boiling at 2165°, and of specific gravity 0939 at 15°/15°.
By treatment with nitric acid it yields p-nitrosodiethylaniline, from which pure diethylaniline may be obtained together with nitrosophenol by heating with dilute sodium hydroxide solution. Diethylaniline is used for the production of the dyestuffs brilliant green, patent blue V, and ethyl purple 6 B.
Ethylbenzylaniline, C6H5N(C2H5) CH1C6H5 - This is a liquid, boiling at 285-286° under 710 mm. pressure; it is used in the preparation of the dyestuffs known as light green SF, patent blue A, and xylene blue AS. It may be prepared by boiling a mixture of ethylaniline (1 part) and benzyl chloride (2 parts) under a reflux condenser for four hours, the product being then fractionated to remove excess of benzyl chloride and ethylaniline (Stebbins).1
 
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