Mauveine: The First Industrial Organic Fine-Chemical

Whilst the origin of the modern industrial revolution is often traced to the Ironbridge Gorge northwest of Birmingham in the UK, less credit is given to one of the birthplaces of the modern organic chemical industry. William Henry Perkin, who at the age of 18 had accidentally produced the first ever synthetic dye (aniline purple, better known as mauveine), set up a factory on the banks of the Grand Union Canal in 1857 to produce it. This small dyeworks was located on a 6-acre site just south of the Black Horse public House, in Greenford, West London. This pub survives to this day, and remains a "local" for the pharmaceutical giant, Glaxo Wellcome, which has its world headquarters nearby.

At the Royal Exhibition of 1862, Queen Victoria made an appearance in a silk gown dyed with mauveine. In the Imperial College chemistry archives, there is a sample of silk (approx 5 x 10 cm in size) dyed with a batch of the original dye synthesised in the 1850s, and a "penny lilac" postage stamp originally thought to have been dyed with the same compound. Curiously, the "correct" structure for the compound was only finally put to rest as late as 1994 (appropriately enough, in a journal named after Perkin himself). This turns out to be a mixture of the compound shown and one other containing one more methyl group (click on the button on the right to see location of the extra methyl group ).

The new colour fell of of fashion in the late 1860s, but out of one of the world's first chemistry "R&D" laboratories, Perkin discovered two new dyes, Britannia Violet and Perkin's Green (the water in the nearby Grand Union Canal was said to have turned a different colour every week- depending on what dyes were being made at the time). In 1869, Perkin synthesised the vivid natural red dye called Alizarin (known chemically as sodium 9,10-dihydro-3,4-dihydroxy-9,10-dioxoanthracene-2-sulfonate). The German company BASF reputedly beat him to the patenting process by one day! Perkin and BASF came to an agreement over the manufacturing processes, but the heyday of synthetic dye manufacturing in Greenford was now waning, and in 1874, Perkin sold his dyeworks to Brooke, Simpson and Spiller. It continued operation under its new owners only until 1876, when it was sold the tar makers Burt, Boulton and Haywood, the dye operations of which joined the British Alizarine Company. This in turn became part of ICI in 1931, and in more modern times became known as Zeneca, a company which can claim to be the successor of Perkin. Nowadays in Manchester, there remains a significant collection of interesting chemicals and other Perkin artefacts. Parts of the original buildings survived until the centenary celebrations in 1957, and the last traces were demolished as recently as 1976. Nowadays, the site of the laboratory for Perkin's dyeworks serves as a distribution point for millions of loaves of bread and rolls for West London.

There is an interesting chemical postscript to the story of Mauveine. Essentially, its synthesis was remarkable because it was based on a one-pot transformation of a simple (mixture) of aromatic anilines, which are simple organic bases. Such bases are peculiarly prone to producing intriguing products in apparently simple reactions. Scorpionine was made recently in Charles Rees' group (appropriately enough Charles is wearing a bow tie dyed with mauveine) from the reaction of S2Cl2 with di-isopropyl ethyl amine. Another simple base (DABCO, or di-aza-[2.2.2]bicyclo-octane) reacts with Bromine to give a very odd compound containing linear chains of 7 bromine ions, the chain having an overall charge of 3-. Both Scorpionine and the DABCO/Br2 adduct are highly coloured, just like mauveine.

Photographs of the Dyeworks site, the Black Horse Pub, and surroundings:

Approximately the site of Perkin's factory Front view of the Black Horse pub, showing typical flower baskets View of GlaxoWellcome Site from Horsenden Hill, looking west
View of the City of London from Horsenden Hill, looking east The Bread distribution centre, site of Perkins R&D Labs.

Further Reading:

  1. The paper in which the correct structure was finally reported; O. Meth-Cohn and M. Smith, J. Chem. Soc., Perkin Transactions 1, 1994, 5.
  2. For a general account of the chemical history, see O. Meth-Cohn and A. S. Travis, Chemistry in Britain, 1995, 31, 547.
  3. Anthony S. Travis "The rainbow makers: the origins of the synthetic dyestuffs industry in Western Europe". Bethlehem: Lehigh UP, 1983.
  4. Henry S. Rzepa, Molecules, 1998, 3, 94-99.

Acknowledgements

I am particularly grateful to Dr Peter Morris of the Science Museum, London, for very helpful comments and corrections on the above history. Many original Perkin samples are in the Science Museum archives, including a large sample of the original mauveine.
(c) H. S. Rzepa, 1995, 1998.