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Name: Andrew K.
Status:  educator
Age: 30s
Location: N/A
Country: N/A
Date: 5/4/2004


Question:
In the mid-19th century, the first synthetic dyes were treated (the aniline dye mauveine was discovered accidentally by Perkins and subsequently various aniline dyes were mass-produced), which would evolutionize the textile and printing dye industries. This in turn had a radical effect on printmaking in Japan when the aniline dyes were imported from Britain and Germany, and largely replaced traditional organic inks used in woodblock prints.

In order to better understand the printmaking process of the time, and the conservation of prints from this period, we want to know about the solubilities of mauveine (aniline purple) and fugitive fuschein (aniline red) dyes.

(1) In what solvent(s), other than water and alcohols, are aniline purple and aniline red MOST soluble ?

(2) Is there a common solvent in which both aniline purple and aniline red are INSOLUBLE ?


Replies:
Google search turned up two interesting sites for your info:

http://encyclopedia.thefreedictionary.com/mauveine

http://www.ch.ic.ac.uk/motm/perkin.html

It is interesting that Mauveine Purple structure was not definitive until 1994. The chemical identity of Aniline Red is tricky to find there seem to be several dyes that carry that label. The probably one is Alizirine red, but the search term uncovered other structures with the name "aniline red".

Regarding solubility, Mauveine Purple is soluble in ethanol according to the first web site above. It should also be soluble in chloroform, methylene chloride, n-methyl pyrrolidone, pyrrolidone, acetone, and toluene. The four nitrogen groups may make it soluble in acid, say HCL, and it could be fractionally precipitated by adding base, e.g. NaOH or ammonia. As the pH increases, the dye should precipitate out. Ethanol, acetone, and pyrrolidone are compatible with water so if you want to dissolve the dye and precipitate it, you could dissolve it in one of these solvents and add water dropwise with stirring. As more water is added the dye will become less soluble in the mixed solvent and begin to precipitate out.

Which solvent(s) you use depends upon what you want to do with the dye subsequently.

Vince Calder



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