Wikipedia

Mauveine

Mauveine,also known asaniline purpleandPerkin's mauve,was one of the first syntheticdyes.[1][2]It was discoveredserendipitouslybyWilliam Henry Perkinin 1856 while he was attempting to synthesise the phytochemicalquininefor the treatment ofmalaria.[3]It is also among the first chemical dyes to have been mass-produced.[4][5]

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

Chemistry

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Mauveine is a mixture of four relatedaromaticcompounds differing in number and placement ofmethyl groups.Itsorganic synthesisinvolves dissolvinganiline,p-toluidine,ando-toluidineinsulfuric acidand water in a roughly 1:1:2 ratio, then addingpotassium dichromate.[6]

Mauveine A(C26H23N+4X−) incorporates 2 molecules ofaniline,one ofp-toluidine, and one ofo-toluidine.Mauveine B(C27H25N+4X−) incorporates one molecule each of aniline,p-toluidine, and two ofo-toluidine. In 1879, Perkin showed mauveine B related tosafraninesbyoxidative/reductiveloss of thep-tolyl group.[7]In fact,safranineis a 2,8-dimethylphenaziniumsalt, whereas theparasafranineproduced by Perkin is presumed[8]to be the 1,8- (or 2,9-) dimethylisomer.

The molecular structure of mauveine proved difficult to determine, finally being identified in 1994.[9]In 2007, two more were isolated and identified:mauveine B2,an isomer of mauveine B with methyl on different aryl group, andmauveine C,which has one morep-methyl group than mauveine A.[10]

  • Skeletal formulaof mauveine A
  • Skeletal formula of mauveine B
  • Skeletal formula of mauveine B2
  • Skeletal formula of mauveine C

In 2008, additional mauveines and pseudomauveines were discovered, bringing the total number of these compounds up to 12.[11]In 2015 a crystal structure was reported for the first time.[12]

History

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ProfessorCharles Rees—wearing a bow tie dyed with an original sample of mauveine—holding anRSCjournal named after Perkin

Mauveine#8D029B
#8D029B

In 1856,William Henry Perkin,then age 18, was given a challenge by his professor,August Wilhelm von Hofmann,to synthesizequinine.In one attempt, Perkinoxidizedaniline usingpotassium dichromate,whosetoluidineimpurities reacted with the aniline and yielded a black solid, suggesting a "failed" organic synthesis. Cleaning the flask with alcohol, Perkin noticedpurpleportions of the solution.

Suitable as a dye ofsilkand othertextiles,it waspatentedby Perkin, who the next year opened a dyeworks mass-producing it atGreenfordon the banks of theGrand Union CanalinMiddlesex.[13]It was originally calledaniline purple.In 1859, it was namedmauvein England via the French name for themallowflower, and chemists later called it mauveine.[14]Between 1859 and 1861, mauve became a fashion must have. The weekly journalAll the Year Rounddescribed women wearing the colour as "all flying countryward, like so many migrating birds of purple paradise".[15]Punchmagazinepublished cartoons poking fun at the huge popularity of the colour “The Mauve Measles are spreading to so serious an extent that it is high time to consider by what means [they] may be checked.”[16][17][18]

By 1870, demand succumbed to newer synthetic colors in thesynthetic dyeindustry 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,purpurinandlydin.[19]

Laborers in the aniline dye industry were later found to be at increased risk of bladder cancer, specificallytransitional cell carcinoma,yet by the 1950s, the synthetic dye industry hadhelped transform medicine,including cancer treatment.[20][21][22]

References

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  1. ^Hubner (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.JSTOR3105760.S2CID112031120.
  3. ^St. Clair, Kassia (2016).The Secret Lives of Colour.London: John Murray. p. 21.ISBN9781473630819.OCLC936144129.
  4. ^Hicks, Jan (2017-08-25)."William Henry Perkin and the world's first synthetic dye".Science and Industry Museum blog.Retrieved2019-10-07.
  5. ^"The color purple: How an accidental discovery changed fashion forever".CNN. 12 March 2018.
  6. ^A Microscale Synthesis of MauveScaccia, Rhonda L.; Coughlin, David; Ball, David W.J. Chem. Educ.199875 769Abstract
  7. ^Perkin, W. H.(January 1879)."On mauveine and allied colouring matters".J. Chem. Soc. Trans.1879:717–732.doi:10.1039/CT8793500717.
  8. ^Website source: ch.ic.ac.ukLink
  9. ^Meth-Cohn, O.; Smith, M. (1994). "What did W. H. Perkin actually make when he oxidised aniline to obtain mauveine?".Journal of the Chemical Society, Perkin Transactions 1.1994:5–7.doi:10.1039/P19940000005.
  10. ^Seixas De Melo, J.; Takato, S.; Sousa, M.; Melo, M. J.; Parola, A. J. (2007). "Revisiting Perkin's dye(s): The spectroscopy and photophysics of two new mauveine compounds (B2 and C)".Chemical Communications(25):2624–6.doi:10.1039/b618926a.PMID17579759.
  11. ^Sousa, Micaela M.; Melo, Maria J.; Parola, A. Jorge; Morris, Peter J. T.; Rzepa, Henry S.; De Melo, J. Sérgio Seixas (2008). "A Study in Mauve: Unveiling Perkin's Dye in Historic Samples".Chemistry - A European Journal.14(28):8507–8513.doi:10.1002/chem.200800718.hdl:10316/8229.PMID18671308.
  12. ^Plater, M. John; Harrison, William T. A.; Rzepa, Henry S. (2015)."Syntheses and Structures of Pseudo-Mauveine Picrate and 3-Phenylamino-5-(2-Methylphenyl)-7-Amino-8-Methylphenazinium Picrate Ethanol Mono-Solvate: The First Crystal Structures of a Mauveine Chromophore and a Synthetic Derivative".Journal of Chemical Research.39(12):711–718.doi:10.3184/174751915X14474318419130.hdl:2164/5423.
  13. ^Google Earth location:Download
  14. ^Matthew, H.C.G.; Howard Harrison, Brian (2004).Oxford Dictionary of National Biography: In Association with the British Academy.Oxford University Press.ISBN0-19-861393-8.perkins tyrian.purple.
  15. ^Garfield, Simon (2000-09-21)."Simon Garfield on mauve".The Guardian.ISSN0261-3077.Retrieved2020-05-27.
  16. ^Blakemore, Erin."How Malaria Gave Us Mauve".Smithsonian Magazine.Retrieved2020-05-27.
  17. ^Jackson, Shelley."Colors / Mauve | Shelley Jackson".cabinetmagazine.org.Retrieved2020-05-27.
  18. ^"Day dress | V&A Search the Collections".V and A Collections.2020-05-27.Retrieved2020-05-27.
  19. ^Leffmann, Henry; William Beam (1901).Select Methods in Food Analysis.Philadelphia: P. Blakiston's Son & Co. p.77.perkins tyrian.purple.
  20. ^Cartwright, R.A. (1983)."Historical and modern epidemiological studies on populations exposed to N-substituted aryl compounds".Environmental Health Perspectives.49:13–19.doi:10.1289/ehp.834913.PMC1569142.PMID6339220.
  21. ^John E Lesch,The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine(New York: Oxford University Press, 2007),pp 202–3
  22. ^D J Th Wagener,The History of Oncology(Houten: Springer, 2009),pp 150–1.

Further reading

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