Copying Nature: Synthetic Alizarin
摘要
Since prehistoric and ancient times, plants of the Rubiaceae family have been used worldwide for textile dyeing. Their rhizomes and roots contain various anthraquinone glycosides and red anthraquinone dyes, for example alizarin and purpurin, pseudopurpurin, munjistin and rubiadin. Dyer’s madder (Rubia tinctorum L.) is the most prominent plant of this family, used throughout the world, primarily for dyeing textiles. A crucial moment in the history of alizarin was the epoch-making discovery in 1868 by Carl Graebe and Carl Theodore Liebermann that alizarin was a derivative of anthracene. They isolated the substance anthracene, determined its chemical structure and developed a way to synthesise Alizarin from coal tar by bromination. The synthesis of Alizarin, which was still not suitable for industrial production, was published in 1869 in the German academic journal Berichte der deutschen chemischen Gesellschaft zu Berlin, so firms started looking for a suitable production process. In May 1869, BASF and William Henry Perkin independently discovered the same synthesis, the sulfonation of anthraquinone, but the BASF group filed their patent one day earlier (25 June 1869) than Perkin in London. After the discovery of synthetic Alizarin, the use of madder and garancine declined. In the 1870s the price of Alizarin dropped dramatically and the result was that the garancine factories gradually closed their doors. Within little more than a decade, madder plantations were forced to give up operations and many disappeared.