The Unexpected and Incredible Discovery of Mauveine and It’s Synthesis Moriah Stark Cumberland University 1 Cumberland Square, Lebanon, TN 37087

Introduction Results and Discussion Uses of Mauveine Mauveine was the first successful synthetic organic dye. It was When in the same place The thriving period of the mauveine dye was short and ended by accidentally discovered by William H. Perkin in 1856 while as pseudo-mauveine, the mid-1860s. The only exception was its use for printing attempting to synthesize a drug to fight malaria. 1 Mauveine mauveines A and B can be stamps, where in the 1860s they had greater control over the was the first synthetic dye to be commercially used which used to trace the configuration of the starting materials which are hydrocarbons. began the synthetic dye industry. 4 It was initially called Tyrian original methods of Perkin’s The initial configuration of mauveine was formerly identified from Purple which was linked with the color obtained from the Mauveine. 1 In step 2 of samples taken from museum collections and can still be found in Mediterranean sea snail, Murex brandaris. 1 Mauveine is a figure 4, the final products the United Kingdom Victorian postage stamps. 1 Other things purple color, but when the salt in mauveine is heated it were separated and dyed with mauveine include dresses, especially silk dresses, turns to a blue color. 2 Mauveine distinguished after an acid letters, stamps, photographs and a silver tea set. 6 treatment of the tert- Is made with a blend of more than Figure 3: These are the chemical structures 3 thirteen different methyl derivatives butylated material. of different mauvines and what was used in 1 (C24 to C28) of 7-amino-5-phenyl- Mauveine A and mauveine their synthesis. 3-(phenylamino) phenazine- B have been formulated by a mixture of pure N-tert-butyl-p- 5-ium compounds, these are Figure 1: This is the original toluidine/aniline/o-toluidine which was oxidized then removed the different because of the number piece of fabric that was dyed tert-butyl group by catalyzing it with acid. 3 of methyl groups they have, which with mauveine.5 fluctuate from none to four. 1 Mauveine can be found in several forms which include Mauveine A, Mauveine B, and Pseudo- mauveine. 1 The scientists who have attempted to recreate Perkin’s authentic mauveine have failed. They followed Figure 5: Three used postage stamps dyed with mauveine. 6 Perkin’s method which oxidized aniline/o-toluidine/p-toluidine + mixtures with K2Cr2O7/H /H2O. When following this method, the color yielded was a blue shade of mauveine rather than the red shade of mauveine that was first exhibited. 3 To find a Conclusions solution to this problem, one scientist decided to examine By examining different methods of making mauveine using either different methods of making mauveine using either N-phenyl- N-phenyl-p-phenylenediamine or N-alkyl-p-toluidines they found p-phenylenediamine or N-alkyl-p-toluidines then compared the that it stains silk a red mauve shade, which matches the original colors of silk dyed with those results and silk dyed with silk stained with Perkins 1862 authentic mauveine. 3 authentic mauveine. 3 References Experimental 1. Cova, T., Pais, A., & Melo, J. (2017, July 28). Reconstructing the historical synthesis of mauveine from Perkin and Caro: Procedure and details. Retrieved October 13, 2020, from A scientist used two new methods to https://www.nature.com/articles/s41598-017-07239-z 2. Plater, M. J., & Raab, A. (2015). Studies on a Modern Method of Preparing Authentic Mauveine. Journal synthesize mauvine in order to try to of Chemical Research, 39(3), 180-183. doi:10.3184/174751915x14253099516627 get the results closer to authentic 3. Perkin, W. H. “On Mauve or Aniline-Purple.” Proceedings of the Royal Society of London, vol. 13, 1863, Figure 2: The top spot on the pp. 170–176. JSTOR, www.jstor.org/stable/112025. Accessed 13 Oct. 2020. mauveine. The results from this trial 4. Plater, M. John. “The Synthesis of Mauveine a and Mauveine B from N-Tert-Butyl-p-Toluidine.” Journal of left is mauveine B, the lower Figure 4: This is the two-step synthesis of mauveine Chemical Research, vol. 38, no. 3, Mar. 2014, pp. 163–168, doi:10.3184/174751914X13912601347455. are shown in figure 2. spot on the left is mauveine A, A and mauveine B. 3 5. Plater, J., Dr. (2019, November 10). The mystery of the Victorian purple dye. Retrieved October 15, 2020, and the spots on the right are from https://researchoutreach.org/articles/mystery-victorian-purple-dye/ 3 6. Plater, M. John, and Andrea Raab. “Mauveine and the Mauve Shade Six Pence Stamp.” Journal of made by Pekin’s method. Chemical Research, vol. 40, no. 11, Nov. 2016, pp. 648–651, doi:10.3184/174751916X14725625519561.