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Mauveine

May 02, 2024

Mauveine, also known as aniline purple and Perkin's mauve, was one of the first synthetic dyes.[1][2] It was discovered serendipitously by William Henry Perkin in 1856 while he was attempting to synthesise the phytochemical quinine for the treatment of malaria.[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 edit

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.[6]

Mauveine A (C26H23N+4X−) incorporates 2 molecules of aniline, one of p-toluidine, and one of o-toluidine. Mauveine B (C27H25N+4X−) incorporates one molecule each of aniline, p-toluidine, and two of o-toluidine. In 1879, Perkin showed mauveine B related to safranines by oxidative/reductive loss of the p-tolyl group.[7] In fact, safranine is a 2,8-dimethyl phenazinium salt, whereas the parasafranine produced by Perkin is presumed[8] to be the 1,8- (or 2,9-) dimethyl isomer.

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, and mauveine C, which has one more p-methyl group than mauveine A.[10]

  •  
    Skeletal formula of 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 edit

 
Professor Charles Rees—wearing a bow tie dyed with an original sample of mauveine—holding an RSC journal 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 synthesize quinine. 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 of the Grand Union Canal in Middlesex.[13] It was originally called aniline purple. In 1859, it was named mauve in England via the French name for the mallow flower, and chemists later called it mauveine.[14] Between 1859 and 1861, mauve became a fashion must have. The weekly journal All the Year Round described women wearing the colour as "all flying countryward, like so many migrating birds of purple paradise".[15] Punch magazine published 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 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 and lydin.[19]

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

References edit

  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. JSTOR 3105760. S2CID 112031120.
  3. ^ St. Clair, Kassia (2016). The Secret Lives of Colour. London: John Murray. p. 21. ISBN 9781473630819. OCLC 936144129.
  4. ^ Hicks, Jan (2017-08-25). "William Henry Perkin and the world's first synthetic dye". Science and Industry Museum blog. Retrieved 2019-10-07.
  5. ^ "The color purple: How an accidental discovery changed fashion forever". CNN. 12 March 2018.
  6. ^ A Microscale Synthesis of Mauve Scaccia, Rhonda L.; Coughlin, David; Ball, David W. J. Chem. Educ. 1998 75 769 Abstract
  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.uk Link
  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. PMID 17579759.
  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. PMID 18671308.
  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. ISBN 0-19-861393-8. perkins tyrian.purple.
  15. ^ Garfield, Simon (2000-09-21). "Simon Garfield on mauve". The Guardian. ISSN 0261-3077. Retrieved 2020-05-27.
  16. ^ Blakemore, Erin. "How Malaria Gave Us Mauve". Smithsonian Magazine. Retrieved 2020-05-27.
  17. ^ Jackson, Shelley. "Colors / Mauve | Shelley Jackson". cabinetmagazine.org. Retrieved 2020-05-27.
  18. ^ "Day dress | V&A Search the Collections". V and A Collections. 2020-05-27. Retrieved 2020-05-27.
  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. PMC 1569142. PMID 6339220.
  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 edit

  • Simon Garfield (2002). Mauve: How One Man Invented a Color That Changed the World. W. W. Norton & Company. ISBN 978-0393323139.

External links edit

  • Perkin anniversary website 2006-11-11 at the Wayback Machine
  • Rotatable 3D models of mauveine are available using Jmol

May 02, 2024
mauveine, also, known, aniline, purple, perkin, mauve, first, synthetic, dyes, discovered, serendipitously, william, henry, perkin, 1856, while, attempting, synthesise, phytochemical, quinine, treatment, malaria, also, among, first, chemical, dyes, have, been,. Mauveine also known as aniline purple and Perkin s mauve was one of the first synthetic dyes 1 2 It was discovered serendipitously by William Henry Perkin in 1856 while he was attempting to synthesise the phytochemical quinine for the treatment of malaria 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 Contents 1 Chemistry 2 History 3 References 4 Further reading 5 External linksChemistry editMauveine 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 6 Mauveine A C26H23N 4 X incorporates 2 molecules of aniline one of p toluidine and one of o toluidine Mauveine B C27H25N 4 X incorporates one molecule each of aniline p toluidine and two of o toluidine In 1879 Perkin showed mauveine B related to safranines by oxidative reductive loss of the p tolyl group 7 In fact safranine is a 2 8 dimethyl phenazinium salt whereas the parasafranine produced by Perkin is presumed 8 to be the 1 8 or 2 9 dimethyl isomer 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 and mauveine C which has one more p methyl group than mauveine A 10 nbsp Skeletal formula of mauveine A nbsp Skeletal formula of mauveine B nbsp Skeletal formula of mauveine B2 nbsp 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 edit nbsp Professor Charles Rees wearing a bow tie dyed with an original sample of mauveine holding an RSC journal 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 synthesize quinine 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 of the Grand Union Canal in Middlesex 13 It was originally called aniline purple In 1859 it was named mauve in England via the French name for the mallow flower and chemists later called it mauveine 14 Between 1859 and 1861 mauve became a fashion must have The weekly journal All the Year Round described women wearing the colour as all flying countryward like so many migrating birds of purple paradise 15 Punch magazine published 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 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 and lydin 19 Laborers in the aniline dye industry were later found to be at increased risk of bladder cancer specifically transitional cell carcinoma yet by the 1950s the synthetic dye industry had helped transform medicine including cancer treatment 20 21 22 References edit Hubner 2006 History 150 Years of mauveine Chemie in unserer Zeit 40 4 274 275 doi 10 1002 ciuz 200690054 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 S2CID 112031120 St Clair Kassia 2016 The Secret Lives of Colour London John Murray p 21 ISBN 9781473630819 OCLC 936144129 Hicks Jan 2017 08 25 William Henry Perkin and the world s first synthetic dye Science and Industry Museum blog Retrieved 2019 10 07 The color purple How an accidental discovery changed fashion forever CNN 12 March 2018 A Microscale Synthesis of Mauve Scaccia Rhonda L Coughlin David Ball David W J Chem Educ 1998 75 769 Abstract Perkin W H January 1879 On mauveine and allied colouring matters J Chem Soc Trans 1879 717 732 doi 10 1039 CT8793500717 Website source ch ic ac uk Link 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 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 PMID 17579759 Sousa Micaela M Melo Maria J Parola A Jorge Morris Peter J T Rzepa Henry S De Melo J Sergio 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 PMID 18671308 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 Google Earth location Download Matthew H C G Howard Harrison Brian 2004 Oxford Dictionary of National Biography In Association with the British Academy Oxford University Press ISBN 0 19 861393 8 perkins tyrian purple Garfield Simon 2000 09 21 Simon Garfield on mauve The Guardian ISSN 0261 3077 Retrieved 2020 05 27 Blakemore Erin How Malaria Gave Us Mauve Smithsonian Magazine Retrieved 2020 05 27 Jackson Shelley Colors Mauve Shelley Jackson cabinetmagazine org Retrieved 2020 05 27 Day dress V amp A Search the Collections V and A Collections 2020 05 27 Retrieved 2020 05 27 Leffmann Henry William Beam 1901 Select Methods in Food Analysis Philadelphia P Blakiston s Son amp Co p 77 perkins tyrian purple 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 PMC 1569142 PMID 6339220 John E Lesch The First Miracle Drugs How the Sulfa Drugs Transformed Medicine New York Oxford University Press 2007 pp 202 3 D J Th Wagener The History of Oncology Houten Springer 2009 pp 150 1 Further reading editSimon Garfield 2002 Mauve How One Man Invented a Color That Changed the World W W Norton amp Company ISBN 978 0393323139 External links editPerkin anniversary websiteArchived 2006 11 11 at the Wayback Machine Rotatable 3D models of mauveine are available using Jmol Retrieved from https en wikipedia org w index php title Mauveine amp oldid 1210234292, wikipedia, wiki, book, books, library,

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