Is there such a thing as a dye that can stain both oil and water? In other words, does anyone know of an amphiphilic dye? Maybe a surfactant that is also a pretty shade of blue? Or maybe turn one color in oil, but another in water, but stain both well?

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    $\begingroup$ Perhaps not a direct answer to your question, but I would imagine that anionic, water-soluble dyes could be transferred into organic solvents by use of a phase-transfer catalyst. $\endgroup$
    – Greg E.
    Dec 20, 2013 at 5:26
  • $\begingroup$ A napthalimide made with a PEO oligomer amine might split the difference in Day-Glo, doi:10.1016/j.jphotochem.2010.09.002 $\endgroup$
    – Uncle Al
    Mar 13, 2014 at 0:52

1 Answer 1


The diazo dye (1), known as Solvent Yellow 124 or Somalia Yellow is soluble in aliphatic hydrocarbons. In the European Community, it is used to mark low-taxed diesel fuel (for heating purposes). In order to prevent its use in cars, samples are acidified. This results in acetal cleavage and protonation of the diazo-fragment, yielding the red, water-soluble iminoquinone species (2)

solvent-yellow-124 hydrolysis and protonation

Since this is probably not exactly what you wanted, what about dyes that exist in a neutral and a zwitterionic form, depending on the polarity of the solvent?

brooker' merocyanine: neutral and zwitterionic form

Brooker's merocyanine is one of the most prominent examples and show strong solvatochromism, i.e. the colour changes with the polarity of the solvent


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