Mauveine, also known asaniline purple andPerkin's mauve, was one of the first syntheticdyes.[1][2] It was discoveredserendipitously byWilliam Henry Perkin in 1856 while he was attempting to synthesise the phytochemicalquinine for the treatment ofmalaria.[3] It is also among the first chemical dyes to have been mass-produced.[4][5]
Mauveine is a mixture of four relatedaromatic compounds differing in number and placement ofmethyl groups. Itsorganic synthesis involves dissolvinganiline,p-toluidine, ando-toluidine insulfuric acid and 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 tosafranines byoxidative/reductive loss of thep-tolyl group.[7] In fact,safranine is a 2,8-dimethylphenazinium salt, whereas theparasafranine produced 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]
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]
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In 1856,William Henry Perkin, then age 18, was given a challenge by his professor,August Wilhelm von Hofmann, to synthesizequinine. In one attempt, Perkinoxidized aniline usingpotassium dichromate, whosetoluidine impurities reacted with the aniline and yielded a black solid, suggesting a "failed" organic synthesis. Cleaning the flask with alcohol, Perkin noticedpurple portions of the solution.
Suitable as a dye ofsilk and othertextiles, it waspatented by Perkin, who the next year opened a dyeworks mass-producing it atGreenford on the banks of theGrand Union Canal inMiddlesex.[13] It was originally calledaniline purple. In 1859, it was namedmauve in England via the French name for themallow flower, and chemists later called it mauveine.[14] Between 1859 and 1861, mauve became a fashion must have. The weekly journalAll 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 thesynthetic 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 andlydin.[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]
perkins tyrian.purple.
perkins tyrian.purple.