Mauveine
Encyclopedia
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
purple
Purple
Purple is a range of hues of color occurring between red and blue, and is classified as a secondary color as the colors are required to create the shade....
and Perkin's mauve, was the first synthetic organic chemical
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
dye
Dye
A dye is a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and requires a mordant to improve the fastness of the dye on the fiber....
.
Its chemical name is
3-amino-2,±9-dimethyl-5-phenyl-7-(p-tolylamino)phenazinium acetate. The formula is C26H23N4+X− (mauveine A) and C27H25N4+X− (mauveine B, see below).
History
Mauveine was discovered serendipitouslySerendipity
Serendipity means a "happy accident" or "pleasant surprise"; specifically, the accident of finding something good or useful without looking for it. The word has been voted as one of the ten English words hardest to translate in June 2004 by a British translation company. However, due to its...
in 1856 by 18-year-old William Henry Perkin, who was trying to synthesize the anti-malaria
Malaria
Malaria is a mosquito-borne infectious disease of humans and other animals caused by eukaryotic protists of the genus Plasmodium. The disease results from the multiplication of Plasmodium parasites within red blood cells, causing symptoms that typically include fever and headache, in severe cases...
drug quinine
Quinine total synthesis
In total synthesis, the Quinine total synthesis describes the efforts in synthesis of quinine over a 150 year period. The development of synthetic quinine is considered a milestone in organic chemistry although it has never been produced industrially as a substitute for natural occurring quinine...
as a challenge from his professor, August Wilhelm von Hofmann
August Wilhelm von Hofmann
August Wilhelm von Hofmann was a German chemist.-Biography:Hofmann was born at Gießen, Grand Duchy of Hesse. Not intending originally to devote himself to physical science, he first took up the study of law and philology at Göttingen. But he then turned to chemistry, and studied under Justus von...
. In one of his attempts, Perkin oxidized aniline using potassium dichromate. Under these conditions, the aniline reacted with toluidine
Toluidine
There are three isomers of toluidine, which are organic compounds. These isomers are o-toluidine, m-toluidine, and p-toluidine. The o- stands for ortho- , m- stands for meta- , and p- stands for para-...
impurities in it to produce a black solid, a fairly common result in "failed" organic syntheses. While trying to clean out his flask, Perkin discovered that some component of the black solid dissolved in alcohol to give a purple-colored solution, which proved to be an effective dye for silk
Silk
Silk is a natural protein fiber, some forms of which can be woven into textiles. The best-known type of silk is obtained from the cocoons of the larvae of the mulberry silkworm Bombyx mori reared in captivity...
and other textile
Textile
A textile or cloth is a flexible woven material consisting of a network of natural or artificial fibres often referred to as thread or yarn. Yarn is produced by spinning raw fibres of wool, flax, cotton, or other material to produce long strands...
s.
Perkin patent
Patent
A patent is a form of intellectual property. It consists of a set of exclusive rights granted by a sovereign state to an inventor or their assignee for a limited period of time in exchange for the public disclosure of an invention....
ed the new dye, and the following year he opened a dyeworks at Greenford
Greenford
Greenford is a large suburb in the London Borough of Ealing in west London, UK. It was historically an ancient parish in the former county of Middlesex. The most prominent landmarks in the suburb are the A40, a major dual-carriageway; Horsenden Hill, above sea level; the small Parish Church of...
on the banks of the Grand Union Canal
Grand Union Canal
The Grand Union Canal in England is part of the British canal system. Its main line connects London and Birmingham, stretching for 137 miles with 166 locks...
in London
London
London is the capital city of :England and the :United Kingdom, the largest metropolitan area in the United Kingdom, and the largest urban zone in the European Union by most measures. Located on the River Thames, London has been a major settlement for two millennia, its history going back to its...
to mass-produce it. It was originally manufactured under the name of aniline purple or Tyrian purple
Tyrian purple
Tyrian purple , also known as royal purple, imperial purple or imperial dye, is a purple-red natural dye, which is extracted from sea snails, and which was possibly first produced by the ancient Phoenicians...
, also the name of an ancient mollusk-derived natural dye
Natural dye
Natural dyes are dyes or colorants derived from plants, invertebrates, or minerals. The majority of natural dyes are vegetable dyes from plant sources – roots, berries, bark, leaves, and wood — and other organic sources such as fungi and lichens....
. The name mauve
Mauve
Mauve is a pale lavender-lilac color, one of many in the range of purples. The color mauve is named after the mallow flower....
was given to it in England in early 1859, from the French name for the mallow
Malva
Malva is a genus of about 25–30 species of herbaceous annual, biennial, and perennial plants in the family Malvaceae , one of several closely related genera in the family to bear the common English name mallow. The genus is widespread throughout the temperate, subtropical and tropical regions of...
flower, and chemists later called it mauveine. Mauve became highly fashionable in 1862 when Queen Victoria
Victoria of the United Kingdom
Victoria was the monarch of the United Kingdom of Great Britain and Ireland from 20 June 1837 until her death. From 1 May 1876, she used the additional title of Empress of India....
appeared at the Royal Exhibition in a mauve silk gown. Mauve fell out of fashion
Fashion
Fashion, a general term for a currently popular style or practice, especially in clothing, foot wear, or accessories. Fashion references to anything that is the current trend in look and dress up of a person...
in the late 1860s to newer synthetic colors, but not before making Perkin's fortune and launching the synthetic chemical industry
Chemical industry
The chemical industry comprises the companies that produce industrial chemicals. Central to the modern world economy, it converts raw materials into more than 70,000 different products.-Products:...
. The U.S. National Association of Confectioners included mauvein among permitted food colorings as of the early 20th century, with a variety of equivalent names: rosolan, violet paste, chrome violet, anilin violet, anilin purple, Perkins violet, indisin, phenamin, purpurin, tyralin, Tyrian purple, and lydin. Later work on chemical dyes led to the (accidental) development of sulfonamides
Sulfonamide (medicine)
Sulfonamide or sulphonamide is the basis of several groups of drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g., the anticonvulsant sultiame...
and modern chemotherapy
Chemotherapy
Chemotherapy is the treatment of cancer with an antineoplastic drug or with a combination of such drugs into a standardized treatment regimen....
. The color of this dye may be familiar due to its widespread use in spirit duplicator
Spirit duplicator
A spirit duplicator was a low-volume printing method used mainly by schools and churches. It was also used by members of science fiction fandom and early comic book fandom to produce fanzines...
(trade name
Trade name
A trade name, also known as a trading name or a business name, is the name which a business trades under for commercial purposes, although its registered, legal name, used for contracts and other formal situations, may be another....
Ditto) printing machines, popular during the mid-20th century.
Chemical analysis
A modern-day laboratory procedure for the organic synthesisOrganic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
of mauveine consists of dissolving a mixture of aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
, p-toluidine and o-toluidine in sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
and water (large excess poor solubility) in roughly a 1:1:2 ratio followed by addition of potassium dichromate.
The actual molecular structure of mauveine proved difficult to determine and was not known with certainty until 1994.
It is actually a mixture of four related aromatic
Aromaticity
In organic chemistry, Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. The earliest use of the term was in an article by August...
compounds, which differ only in the number and placement of methyl groups. A is built up from 2 molecules of aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
, one of p-toluidine and one of o-toluidine whereas B incorporates aniline, p-toluidine and o-toluidine one molecule each. As Perkin showed in 1879, mauveine B is related to the safranines by oxidative/reductive
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
loss of the p-tolyl group. In fact, safranine itself is a 2,8-dimethyl phenazinium
Phenazine
Phenazine , also called azophenylene, dibenzo-p-diazine, dibenzopyrazine, and acridizine, is a dibenzo annulated pyrazine and the parent substance of many dyestuffs, such as the eurhodines, toluylene red, indulines and safranines.-Synthesis:A classic method for the synthesis of phenazine is the...
salt, whereas the parasafranine produced by Perkin must be presumed to be the 1,8-(or 2,9) dimethyl isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
.
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
of mauveine B with methyl on different aryl group). The list of components was further extended to 12 (+pseudomauveine) in 2008.
Medical associations
Aniline dye is associated with transitional cell carcinomaTransitional cell carcinoma
Transitional cell carcinoma is a type of cancer that typically occurs in the urinary system: the kidney, urinary bladder, and accessory organs. It is the most common type of bladder cancer and cancer of the ureter, urethra, and urachus...
.
External links
- Perkin anniversary website
- Rotatable 3D models of mauveine are available using JmolJmolJmol is an open-source Java viewer for chemical structures in 3D,that does not require 3D acceleration plugins.Jmol returns a 3D representation of a molecule that may be used as a teaching tool, or for research e.g...