Aniline purple, development

The next milestone in the development of organic synthesis was the preparation of the first synthetic dye, mauveine (aniline purple) by Perkin in 1856 Perkin, 1856, 1862). This is generally regarded as the first industrial organic synthesis. It is also a remarkable example of serendipity. Perkin s goal was the synthesis of the antimalarial drug quinine by oxidation of N-allyl toluidine (Fig. 2.4). 

The foundation of the synthetic dye industry is universally attributed to William Henry Perkin on account of his discovery in 1856 of a purple dye which he originally gave the name Aniline Purple, but which was later to become known as Mauveine. Perkin was a young enthusiastic British organic chemist who was carrying out research aimed not initially at synthetic dyes but rather at developing a synthetic route to quinine, the antimalarial drug. His objective in one particular set of experiments was... 

With the influence of an artist friend interested in painting and dyes, he started to develop aniline purple (Tyrian purple) production, which he patented in 1856 and set up a factory for. The dyestuff industry soon flourished. In 1859, Emanuel Verguin prepared the important dye fuschine, which was subsequently produced in Basel. In 1869, Perkin patented the synthesis of the natural dye alizarin, at the same time as Caro, Lieberman, and Graebe did so in Germany. Later, moreover, Perkin prepared alizarin from anthracene, which had been... 

Among the first attempts to synthesise quinine, though unsuccessful, is the one by William Henry Perkin (1838-1907), an 18-year-old student at the Royal College of Chemistry in London. While the constitution of quinine was stiU rmknown, Perkin thought it would be possible to produce this alkaloid by oxidising N-allyl toluidine. Instead, he prepared accidentally aniline purple, which became better known as mauveine, the first industrial dyestuff and a cornerstone for the development of the chemical industry. 

Aniline is a purple dye that has the distinction of being the first synthetic dye ever made. It was developed in Germany at the end of the 19th century and its manufacture led to the development of the entire synthetic chemical and pharmaceutical industry that we know today. It is used as a dye and also as a stage in the synthesis of other dyes and chemicals. Unfortunately, both aniline and its derivatives, such as monomethyl-analine and dimethylaniline, are toxic. 

Certain molluscs Purpura lapillus, P. hcemastoma, and various species of Murex), when crushed and exposed to sunlight, develop a purple dyestuff which was highly prized by the ancients. According to Schunck [84] the dyestuff, punicine, is insoluble in water, alcohol, and ether, slightly soluble in benzene and glacial acetic acid, and easily soluble in aniline and concentrated sulphuric acid [85]. It sublimes with partial decomposition in leaflets, which have a metallic lustre. 

Mauve (also mauveine) may refer to a number of purple compounds based on aniline dyestuffs - so-called coal tar colours -which became available in the second half of the nineteenth century. The name mauve also refers specifically to the dye developed by William Henry Perkin in 1856. Perkin initially called this Tyrian purple (. v.) as this would enhance its value however, his detractors preferred to call it purple sludge (Garfield, 2000). 

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