The Methylation of Para Aminophenol By Means of Formaldehyde

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It separates from solution in crystalline form, the color of the crystals de- pending upon the presence of impurities in the solution. The pure secondary base yields nearly white, or gray, minute needles, having a low solubility in cold water. When precipitation is effected from solution containing p-aminophenol, formation of the nitrosamine is noticeably delayed, due no doubt to the superior reactivity of the primary base. In such cases, also, tar- formation is almost invariable, and the nitro...samine separates as brown granular crystals. Under unfavorable conditions the separation of tar has been considerable, rendering purification of the nitro- samine, without considerable loss, impossible.
The nitrosamine is a somewhat unstable compound, and suf- fers serious decomposition, with darkening, if an attempt is made to dry it while moist with any trace of the acid mother- liquor, or to crystallize it from strong alcohol ; less extensive de- composition occurs if dilute alcohol is used. Rather oddly, the compound seems to be most satisfactorily crystallized from hot water, in which it is moderately soluble.


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