Mauveine

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Letter from Perkin's son, with a sample of dyed silk

Mauveine, also known as aniline purple and Perkin's mauve, was the first synthetic organic chemical dye,[1][2] discovered serendipitously in 1856. Its chemical name is 3-amino-2,±9-dimethyl-5-phenyl-7-(p-tolylamino)phenazinium acetate.

Chemistry

Mauveine is a mixture of four, related aromatic compounds differing in number and placement of methyl groups. Its organic synthesis involves dissolving aniline, p-toluidine, and o-toluidine in sulfuric acid and water in a roughly 1:1:2 ratio, then adding potassium dichromate.[3]

Mauveine A (C26H23N4+X−) incorporates 2 molecules of aniline, one of p-toluidine, and one of o-toluidine. Mauveine B (C27H25N4+X−) incorporates one molecule each of aniline, p-toluidine, and o-toluidine. In 1879, Perkin showed mauveine B related to safranines by oxidative/reductive loss of the p-tolyl group.[4] (In fact, safranine is a 2,8-dimethyl phenazinium salt, whereas the parasafranine produced by Perkin is presumed[5] to be the 1,8-(or 2,9) dimethyl isomer.)

Difficult to determine, mauveine's molecular structure was identified in 1994.[6] In 2007, two more were isolated and identified: mauveine B2 (an isomer of mauveine B with methyl on different aryl group) and mauveine C (an additional p-methyl group on mauveine A).[7]

  • skeletal formula of mauveine A
  • skeletal formula of mauveine B
  • skeletal formula of mauveine B2
  • skeletal formula of mauveine C

In 2008, the mauveine list grew to twelve (including pseudomauveine).[8]

Professor Charles Rees—wearing bow tie dyed with original sample of mauveine—holding RSC journal named after Perkin

History

In 1856, William Henry Perkin, age 18, given a challenge by his professor, August Wilhelm von Hofmann, sought to synthesize quinine, the anti-malaria drug. In one attempt, Perkin oxidized aniline using potassium dichromate, whose toluidine impurities reacted with the aniline and yielded a black solid—suggesting a "failed" organic synthesis. Cleaning the flask with alcohol, Perkin noticed purple portions of the solution.

Suitable as a dye of silk and other textiles, it was patented by Perkin, who the next year opened a dyeworks mass-producing it at Greenford on the banks[9] of the Grand Union Canal in London. It was originally called aniline purple or Tyrian purple, the name of an ancient natural dye derived from mollusks.[10] By 1859, it attained the name mauve in England via the French name for the mallow flower, and chemists later called it mauveine.[10] Mauve came into great vogue when in 1862 Queen Victoria appeared at the Great Exhibition in a mauve silk gown—dyed with mauveine. By 1870, its great demand succumbed to newer synthetic colors in the synthetic dye industry launched by mauveine.

In the early 20th century, the U.S. National Association of Confectioners permitted mauveine as a food coloring with a variety of equivalent names: rosolan, violet paste, chrome violet, anilin violet, anilin purple, Perkin's violet, indisin, phenamin, purpurin, tyralin, Tyrian purple, and lydin.[11] Mid-20th century, it was used widely in the spirit duplicator printing machines, popular via the trade name Ditto.

Laborers in the aniline dye industry were later found at increased risk of bladder cancer, specifically transitional cell carcinoma,[12] yet by the 1950s, the synthetic dye industry helped transform medicine,[13] including cancer treatment.[14] (See "Aniline", section "History".)

References

  1. ↑ Hubner K (2006). "History – 150 Years of mauveine". Chemie in unserer Zeit 40 (4): 274–275. doi:10.1002/ciuz.200690054. 
  2. ↑ Anthony S. Travis (1990). "Perkin’s Mauve: Ancestor of the Organic Chemical Industry". Technology and Culture 31 (1): 51–82. doi:10.2307/3105760. JSTOR 3105760. 
  3. ↑ A Microscale Synthesis of Mauve Scaccia, Rhonda L.; Coughlin, David; Ball, David W. J. Chem. Educ. 1998 75 769 Abstract
  4. ↑ W. H. Perkin, "On mauveine and allied colouring matters", J. Chem. Soc. Trans., 1879, 717–732. DOI: 10.1039/CT8793500717.
  5. ↑ Website source: ch.ic.ac.uk Link
  6. ↑ O. Meth-Cohn, M. Smith, "What did W. H. Perkin actually make when he oxidised aniline to obtain mauveine?", J. Chem. Soc. Perkin 1, 1994, 5–7. DOI: 10.1039/P19940000005.
  7. ↑ Revisiting Perkin's dye(s): The spectroscopy and photophysics of two new mauveine compounds (B2 and C) J. Seixas de Melo, S. Takato, M. Sousa, M. J. Melo and A. J. Parola Chem. Commun., 2007, 2624–26,doi:10.1039/b618926a
  8. ↑ A Study in Mauve: Unveiling Perkin!s Dye in Historic Samples, M. M. Sousa, M. J. Melo, A. J. Parola, P. J. T. Morris, H. S. Rzepa, and J. S. Seixas de Melo Chem. Eur. J., 2008, 14, 8507– 8513, doi:10.1002/chem.200800718
  9. ↑ Google Earth location: Download
  10. ↑ 10.0 10.1 Matthew,, H.C.G.; Brian Howard Harrison (2004). Oxford Dictionary of National Biography: In Association with the British Academy. Oxford University Press. ISBN 0-19-861393-8. 
  11. ↑ Leffmann, Henry; William Beam (1901). Select Methods in Food Analysis. Philadelphia: P. Blakiston's Son & Co. 
  12. ↑ Cartwright, R.A. (1983). "Historical and modern epidemiological studies on populations exposed to N-substituted aryl compounds". Environmental Health Perspectives 49: 13–19. PMC 1569142. PMID 6339220. 
  13. ↑ John E Lesch, The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine (New York: Oxford University Press, 2007), pp 202–3.
  14. ↑ D J Th Wagener, The History of Oncology (Houten: Springer, 2009), pp 150–1.

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