Chemistry:Azuline

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Azuline is a coal-tar blue dye that became popular for colouring silk in 1861. It was one of the first synthetic dyes.[1] The name was a combination of "azure" and "aniline". A variant of the name was "Azurine". The word was introduced as a colour term about the same time as "mauve" and "magenta", but it has not survived in the English language.[2]

The dye is made from phenol, first oxidising it with oxalic acid and sulfuric acid to make a red substance called rosolic acid. By treating this with ammonia, a dye called red coralline or péonine was made. When reacted with aniline, the blue azuline was produced. This was invented by Jules Persoz in Paris. A company in Lyon called Guinon, Marnas & Bonnet bought the process and established a patent.[3] In 1862 azuline was selling for 450 francs per kilogram.[4]

Chemists at first did not know the structure of the molecules in the coal tar dyes including azuline.[5]

Use of azuline was superseded by aniline blue.[6]

Properties

As a solid, azuline has a metallic appearance with a copper red colour. It hardly dissolves in water, but does dissolve in alcohol. In alcohol it has a strong blue colour, but still has a red tinge.[7] The dye is colourfast, resisting fading by light.[5] Sulfuric acid solution gives a red solution. Iodine destroys the substance. Ammonium sulfide reduces the colour to pale yellowish-brown.[8]

References

  1. "The New Blue Dye "Azuline"". The Chemical News 3 (73): 255. 27 April 1861. https://books.google.com/books?id=D-w3AQAAIAAJ&pg=PA255. 
  2. Blaszczyk, Regina Lee; Spiekermann, Uwe (2017) (in en). Bright Modernity: Color, Commerce, and Consumer Culture. Springer. ISBN 9783319507453. https://books.google.com/books?id=-qUyDwAAQBAJ&pg=PA101. 
  3. Gaudillière, J. (1998) (in en). The Invisible Industrialist: Manufacture and the Construction of Scientific Knowledge. Springer. pp. 128–129. ISBN 9781349264438. https://books.google.com/books?id=AyaxCwAAQBAJ&pg=PA129. 
  4. Morris, Peter J.T.; Travis, Anthony S. (November 1992). "A History of the International Dyestuff Industry". http://colorantshistory.org/HistoryInternationalDyeIndustry.html. Retrieved 30 January 2018.  Originally in American Dyestuff Reporter vol 81 no 11
  5. 5.0 5.1 Reinhardt, Carsten; Travis, Anthony S. (2013) (in en). Heinrich Caro and the Creation of Modern Chemical Industry. Springer Science & Business Media. p. 116. ISBN 9789401593533. https://books.google.com/books?id=NgzwCAAAQBAJ&pg=PA116. 
  6. REIMANN, M. (1868) (in en). ANILINE AND ITS DERIVATIVES. J. Wiley and son. p. 148. https://archive.org/details/onanilineandits00lairgoog. 
  7. "Dye-stuffs". https://www2.cs.arizona.edu/patterns/weaving/articles/ce2_dyes.pdf. Retrieved 30 January 2018. 
  8. Perkin, W. H. (1862). "XIX. On colouring matters derived from coal tar". Quarterly Journal of the Chemical Society of London 14 (1): 230. doi:10.1039/qj8621400230. https://zenodo.org/record/1429763.