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Mauveine, also known as aniline purple and Perkin's mauve, was one of the first synthetic
dyes Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy (DyE song), Fantasy" from his first album ''Taki 183 (album), Taki 183''. This video became popular, attracting ...
. It was discovered serendipitously by William Henry Perkin in 1856 while he was attempting to synthesise the phytochemical
quinine Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to ''Plasmodium falciparum'' that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal leg ...
for the treatment of
malaria Malaria is a Mosquito-borne disease, mosquito-borne infectious disease that affects vertebrates and ''Anopheles'' mosquitoes. Human malaria causes Signs and symptoms, symptoms that typically include fever, Fatigue (medical), fatigue, vomitin ...
. It is also among the first chemical dyes to have been mass-produced.


Chemistry

Mauveine is a mixture of four related
aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
compounds differing in number and placement of
methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...
s. Its
organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...
involves dissolving
aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
, ''p''-toluidine, and ''o''-toluidine in
sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...
and water in a roughly 1:1:2 ratio, then adding
potassium dichromate Potassium dichromate is the inorganic compound with the formula . An orange solid, it is used in diverse laboratory and industrial applications. As with all hexavalent chromium compounds, it is chronically harmful to health. It is a crystalline ...
. ''Mauveine A'' () incorporates 2 molecules of
aniline Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
, one of ''p''-toluidine, and one of ''o''-toluidine. ''Mauveine B'' () incorporates one molecule each of aniline, ''p''-toluidine, and two of ''o''-toluidine. In 1879, Perkin showed mauveine B related to
safranine Safranin (Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endos ...
s by
oxidative Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
/ reductive loss of the ''p''-tolyl group. In fact,
safranine Safranin (Safranin O or basic red 2) is a biological stain used in histology and cytology. Safranin is used as a counterstain in some staining protocols, colouring cell nuclei red. This is the classic counterstain in both Gram stains and endos ...
is a 2,8-dimethyl phenazinium salt, whereas the parasafranine produced by Perkin is presumed to be the 1,8- (or 2,9-) dimethyl
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
. The molecular structure of mauveine proved difficult to determine, finally being identified in 1994. 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. File:Mauveine a skeletal org.svg,
Skeletal formula The skeletal formula, line-angle formula, bond-line formula or shorthand formula of an organic compound is a type of minimalist structural formula representing a molecule's Atom, atoms, structural isomer, bonds and some details of its molecular ...
of mauveine A File:Mauveine b skeletal org.svg, Skeletal formula of mauveine B File:Mauveine b2 skeletal org.svg, Skeletal formula of mauveine B2 File:Mauveine c skeletal org.svg, Skeletal formula of mauveine C
In 2008, additional mauveines and pseudomauveines were discovered, bringing the total number of these compounds up to 12. In 2015 a crystal structure was reported for the first time.


History

In 1856, William Henry Perkin, then age 18, was given a challenge by his professor,
August Wilhelm von Hofmann August Wilhelm von Hofmann (8 April 18185 May 1892) was a German chemist who made considerable contributions to organic chemistry. His research on aniline helped lay the basis of the aniline-dye industry, and his research on coal tar laid the g ...
, to synthesize
quinine Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to ''Plasmodium falciparum'' that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal leg ...
. In one attempt, Perkin
oxidized Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
aniline using
potassium dichromate Potassium dichromate is the inorganic compound with the formula . An orange solid, it is used in diverse laboratory and industrial applications. As with all hexavalent chromium compounds, it is chronically harmful to health. It is a crystalline ...
, whose
toluidine There are three isomers of toluidine, which are organic compounds discovered and named by James Sheridan Muspratt and August Wilhelm von Hofmann in 1845. These isomers are O-Toluidine, ''o''-toluidine, ''m''-toluidine, and ''p''-toluidine, with the ...
impurities reacted with the aniline and yielded a black solid, suggesting a "failed" organic synthesis. Cleaning the flask with alcohol, Perkin noticed
purple Purple is a color similar in appearance to violet light. In the RYB color model historically used in the arts, purple is a secondary color created by combining red and blue pigments. In the CMYK color model used in modern printing, purple is ...
portions of the solution. Suitable as a dye of
silk Silk is a natural fiber, natural protein fiber, some forms of which can be weaving, woven into textiles. The protein fiber of silk is composed mainly of fibroin and is most commonly produced by certain insect larvae to form cocoon (silk), c ...
and other
textile Textile is an Hyponymy and hypernymy, umbrella term that includes various Fiber, fiber-based materials, including fibers, yarns, Staple (textiles)#Filament fiber, filaments, Thread (yarn), threads, and different types of #Fabric, fabric. ...
s, it was
patent A patent is a type of intellectual property that gives its owner the legal right to exclude others from making, using, or selling an invention for a limited period of time in exchange for publishing an sufficiency of disclosure, enabling discl ...
ed by Perkin, who the next year opened a dyeworks mass-producing it at
Greenford Greenford () is a large town in the London Borough of Ealing in West London, Greater London, London, England, lying west from Charing Cross. It has a population of 46,787 inhabitants. Greenford is served by Greenford station, Greenford Stati ...
on the banks of the
Grand Union Canal The Grand Union Canal in England is part of the Canals of the United Kingdom, British canal system. It is the principal navigable waterway between London and the Midlands. Starting in London, one arm runs to Leicester and another to Birmi ...
in Middlesex. It was originally called ''aniline purple''. In 1859, it was named ''
mauve Mauve ( ; ) is a pale purple color named after the mallow flower (French: ). The first use of the word ''mauve'' as a color was in 1796–1798 according to the ''Oxford English Dictionary'', but its use seems to have been rare before 1859. ...
'' in England via the French name for the mallow flower, and chemists later called it mauveine. Between 1859 and 1861, mauve became a fashion must have. The weekly journal ''
All the Year Round ''All the Year Round'' was a British weekly literary magazine founded and owned by Charles Dickens, published between 1859 and 1895 throughout the United Kingdom. Edited by Dickens, it was the direct successor to his previous publication '' Ho ...
'' described women wearing the colour as "all flying countryward, like so many migrating birds of purple paradise". ''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 heymay be checked.” 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''. Laborers in the aniline dye industry were later found to be at increased risk of bladder cancer, specifically
transitional cell carcinoma Transitional cell carcinoma is a type of cancer that arises from the transitional epithelium, a tissue lining the inner surface of these hollow organs. It typically occurs in the urothelium of the urinary system; in that case, it is also called ...
, yet by the 1950s, the synthetic dye industry had helped transform medicine, including cancer treatment.D J Th Wagener, ''The History of Oncology'' (Houten: Springer, 2009)
pp 150–1


References


Further reading

*


External links


Perkin anniversary website
sup> {{Webarchive, url=https://web.archive.org/web/20061111102500/http://www.rsc.org/Chemsoc/Activities/Perkin/index.asp , date=2006-11-11 * Rotatable 3D models of mauveine ar

using
Jmol Jmol is computer software for molecular modelling of chemical structures in 3 dimensions. It is an open-source Java viewer for chemical structures in 3D. The name originated from ''Jva (the programming language) + olcules, and also the m ...
Azin dyes English inventions History of chemistry Organic chemistry Shades of violet Phenazines Quaternary ammonium compounds Chemical mixtures 1856 introductions