V-Ethylaniline

Other catalysts that can be used are boron trifluoride (5), copper—chromium oxides (6), phosphoric acid (7), and siUca-alurnina (8). Under similar conditions, ethanol yields /V-ethylaniline [103-69-5] and /V,/V-diethylaniline [91-66-7] (9,10). 

The normal boiling point of /V-ethylaniline is 204°C. Therefore, steam distillation makes possible the distillation of /V-ethylaniline at atmospheric pressure at a temperature of 99.15°C instead of its normal boiling point of 204°C. Commercial appHcations of steam distillation include the fractionation of cmde tall oil (qv) (84), the distilling of turpentine (see Terpenoids), and certain essential oils (see Oils, essential). A detailed calculation of steam distiUation of turpentine has been reported (85). 

A chiral hydride complex, tentatively assumed to be 86, prepared by partially reacting LAH with (- )-N-methylephedrine (1 equivalent) and /V-ethylaniline (2 equivalents) was found to reduce 2-acetyl-5,8-dimethoxy-3,4-dihydronaphtha-lene (87) quantitatively to the (- )-carbinol (88) with 92% e.e. (94,95). Carbinol 88, which was obtained optically pure by recrystallization, could be converted to (/ )-(-)-2-acetyl-5,8-dimethoxy-l,2,3,4-tetrahydro-2-naphthol (89). The lat-... 

The industrial source of indole has been tsolatinn from coal-tar distillate. Several patents for the manufacture of indole have been issued with aniline and ethylene glycol, aniline and ethylene oxide. 2-ethylaniline. and /V-ethylaniline as the starling materials. 

Figure 4.9 The dependence of yields and selectivity of /V-ethylaniline dehydrogenation on conditional contact time (a) 600 °C and (b) 640 °C (1 benzonitrile 2 selectivity and 3 side product yield).

Modification of LAH with (-)-)V-methylephedrine (14) and )V-ethylaniline affords another chiral reducing agent (50). " A variety of aromatic ketones are reduced by (SO) to (S)-carbinols in high optical yields (Scheme 8). Acyclic a,3-unsaturated ketones are also reduced to (S)-carbinols with high selectivity (76-92% ee), but cyclic enones are reduced with only moderate selectivity. 

New processes include synthesis of /V-alkylated anilines from olefins and aniline in an inert solvent with at least one catalyst from a range that includes alkali metal alcoholates, alkaline earth metal alcoholates, alkali metal amides and alkaline earth amides36. The uses for /V,/V-dimethylaniline (11) include in the manufacture of polyester resins, sulfur recovery (in copper refining), insecticides and fungicides, dyes, pharmaceuticals, explosives, rubber products, specialty isocyanates and petroleum additives. The /V-ethylaniline (26) is a dye intermediate and rubber additive, and is used for bum control in explosives, while /V,/V-diclhylaniline is used in production of polyester resins, pharmaceuticals, diazo prints (lithographic), and dyes, and as a petroleum additive37. 

Nitration of p-nitroaniline (15b), or reacting picric acid with phosphorus pentachloride, yields trinitrochlorobenzene, which on amination affords 2,4,6-trinitroaniline, the explosive picramide. Phosgenation of /V-ethylaniline (26) gives a substituted urea used as a stabilizer for explosives. Diphenylamine (8) is used as a stabilizer, for nitrocellulose explosives as well as for celluloid, and also as a solid rocket propellant. Ethylaniline 26 is employed in the manufacture of centralite, a stabilizer in smokeless powder. Other uses for 15b, the largest volume nitroaniline, include in the production of dyes, antioxidants and pharmaceuticals. 

ETHYLANILINE or V-ETHYLANILINE (103-69-5) Combustible liquid (flash point 185°F/85°C). Decomposes on contact with sunlight or air. Reacts violently with strong oxidizers, strong acids, acid fumes, nitric acid, with risk of fire, explosion, and possible formation of toxic vapors of aniline and oxides of nitrogen. 

The effect of the substitution on the reactivity of the monomer was studied in more detail recently [231]. The electrooxidation of a selection of N-alkyl-substituted (V-ethyl- and A7,V-dimethyl-) and ring-substituted (o-, m-, p-methyl-, o-ethyl-) aniline derivatives at no glass electrodes was investigated using UV-vis spectroscopy in sim (further details follow). With V-ethylaniline, well defined absorbance peaks of an intermediate and an end product were observed after an anodic potential step (Fig. 17). Conversion of the electrogenerated intermediate into an end product... 

Fig. 17. UV- s spectra obtained after different time intervals (as indicated in minutes) after a potential step to rhe — +1.2 V in solutions that contained 100 (top), 20 (middle), and 1 (bottom) of V-ethylaniline. For further experimental details, see [231].

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