Mauveine

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Mauveine

Mauveine, also known as aniline
Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
purple
Purple

Purple is a general term for the range of shades of color occurring between red and blue. It occurs by mixing the primary colors red and blue in varying proportions, with possibly a very small quantity of the third primary color ....
and Perkin's mauve, was the first synthetic organic

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
dye

Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
. 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).

eine was discovered serendipitously in 1856 by an 18-year old, William Henry Perkin, who was trying to synthesize the anti-malaria

Malaria

Malaria is a Vector -borne infectious disease caused by protozoan parasites. It is widespread in Tropics and subtropical regions, including parts of the Americas, Asia, and Africa....
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 offered by his professor, August Wilhelm von Hofmann.

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Encyclopedia

Organic chemistry

Dye

History

Mauveine was discovered serendipitously in 1856 by an 18-year old, William Henry Perkin, who was trying to synthesize the anti-malaria

Malaria

Quinine total synthesis

Potassium dichromate

Potassium dichromate, K2Cr2O7, is a common inorganic compound chemical reagent, most commonly used as an oxidizing agent in various laboratory and industrial applications....
. 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....
impurities in it to produce a black solid, a fairly common result in "failed" organic syntheses. However, 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 weaving into textiles. The best-known type of silk is obtained from Pupa#Cocoons made by the larvae of the mulberry silkworm Bombyx mori reared in captivity ....
and other textile

Textile

A textile is a flexible material consisting of a network of natural or artificial fibres often referred to as thread or yarn. Yarn is produced by Spinning raw wool fibres, linen, cotton, or other material on a spinning wheel to produce long strands known as yarn....
s.

Perkin patent

Patent

A patent is a set of exclusive rights granted by a state to an inventor or his assignee for a term of patent in exchange for a disclosure of an invention....
ed the new dye and the next year, he opened a dyeworks at Greenford

Greenford

Greenford, historically Greenford Magna, is a suburb in the London Borough of Ealing in west London, England. Greenford is one of the oldest recorded places in Ealing, first referred to in a legal document dated AD 845....
on the banks of the Grand Union Canal

Grand Union Canal

The Grand Union Canal in England is part of the Canals of Great Britain. Its main line connects London and Birmingham, stretching for 220 km with 166 Canal lock....
in London

London

London is the capital of both England and the United Kingdom, and the most populous municipality in the European Union. An important settlement for two millennia, History of London goes back to its founding by the Roman Empire....
in order 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 dye which was first produced by the ancient Phoenicians in the city of Tyre, Lebanon....
, also the name of an ancient mollusk-derived natural dye. The name mauve was given to it in England in early 1859, from the French name for the mallow

Mallow

Mallow or Mallows may refer to:Nature:* Malvaceae, family of plants; in particular the following genera:** Abelmoschus** Althaea ? Marsh mallow...
flower, and chemists later called it mauveine. Mauve

Mauve

Mauve is a pale lavender -lilac color, one of many in the range of purples.Mauve is more grey and more blue than a pale tint of magenta would be....
became highly fashionable in 1862 when Queen Victoria of the United Kingdom

Victoria of the United Kingdom

Victoria was from 20 June 1837 the Queen regnant of the United Kingdom of Great Britain and Ireland and from 1 May 1876 the first Empress of India of the British Raj until her death....
appeared at the Royal Exhibition in a mauve silk gown. Mauve fell out of fashion

Fashion

Fashion refers to the styles and customs prevalent at a given time. In its most common usage, "fashion" exemplifies the appearances of clothing, but the term encompasses more....
in the late 1860s to newer synthetic colors, but not before making Perkin's fortune and birthing the synthetic chemical industry

Chemical industry

The chemical industry comprises the companies that produce industrial chemicals. It is central to modern world economy, converting raw materials into more than 70,000 different 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 also led to the (accidental) development of modern chemotherapy

Chemotherapy

Chemotherapy, in its most general sense, refers to treatment of disease by chemicals that kill cells, specifically those of micro-organisms or cancer....
(see Sulfonamide

Sulfonamide (medicine)

File:Sulfonamide.pngFile:Hydrochlorothiazide-2D-skeletal.pngFile:Furosemide.svgThere are several sulfonamide-based groups of drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the Sulfonamide group....
).

The color of this dye may be familiar from its widespread use in spirit duplicator

Spirit duplicator

A spirit duplicator was a low-volume printing method used mainly by schools and churches. Sheets printed on a ditto machine were called ditto sheets, or just dittos....
(trade name Ditto) printing machines, popular during the mid-20th century.

Chemical analysis

A modern-day laboratory procedure for the organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
of mauveine consists of dissolving a mixture of aniline

Aniline

Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....
and water (large excess poor solubility) in roughly a 1:1:2 ratio followed by addition of potassium dichromate

Potassium dichromate

Potassium dichromate, K2Cr2O7, is a common inorganic compound chemical reagent, most commonly used as an oxidizing agent in various laboratory and industrial applications....
. The actual molecular structure of mauveine proved quite difficult to determine and was not known with certainty until 1994.

It is actually a mixture of four related aromatic

Aromaticity

Aromaticity is a chemical property in which a conjugated system ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone....
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 Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
, 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 describes all chemical reactions in which atoms have their oxidation number changed.This can be either a simple redox process such as the oxidation of carbon to yield carbon dioxide or the reduction of carbon by hydrogen to yield methane , or it can be a complex process such as the oxidation of sugar in the human body through a ser...
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 annulation pyrazine and the parent substance of many dyestuffs, such as the eurhodines, toluylene red, indulines and safranines....
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 formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
.

In 2007 two other mauveine components were isolated and identified, called mauveine C (an additional p-methyl group on mauveine A) and mauveine B2 (an isomer

Isomer

External links

Rotatable 3D models of mauveine are using Jmol
Jmol

Jmol is an open-source Java viewer for chemical structures in 3D computer graphics. Jmol returns a 3D representation of a molecule that may be used as a teaching tool, or for research e.g....