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==History== In 1839, the German apothecary [[Eduard Simon]] isolated a volatile liquid from the resin (called ''storax'' or ''styrax'' (Latin)) of the American sweetgum tree (''[[Liquidambar styraciflua]]''). He called the liquid "styrol" (now called styrene).<ref>Simon, E. (1839) [https://babel.hathitrust.org/cgi/pt?id=uva.x002457910;view=1up;seq=277 "Ueber den flüssigen Storax (Styrax liquidus)"] (On liquid storax (Styrax liquidus), ''Annalen der Chemie'', '''31''' : 265–277. From p. 268: ''"Das flüchtige Oel, für welches ich den Namen ''Styrol'' vorschlage, … "'' (The volatile oil, for which I suggest the name "styrol", … )</ref><ref>For further details of the history of styrene, see: F. W. Semmler, ''Die ätherischen Öle nach ihren chemischen Bestandteilen unter Berücksichtigung der geschichtlichen Entwicklung'' [The volatile liquids according to their chemical components with regard to historical development], vol. 4 (Leipzig, Germany, Veit & Co., 1907), § 327. Styrol, [https://books.google.com/books?id=nA9aAAAAYAAJ&pg=PA24 pp. 24-28.] {{webarchive |url=https://web.archive.org/web/20180501152357/https://books.google.com/books?id=nA9aAAAAYAAJ&pg=PA24 |date=1 May 2018}}</ref> He also noticed that when styrol was exposed to air, light, or heat, it gradually transformed into a hard, rubber-like substance, which he called "styrol oxide".<ref>(Simon, 1839), p. 268. From p. 268: ''"Für den festen Rückstand würde der Name Styroloxyd passen."'' (For the solid residue, the name "styrol oxide" would fit.)</ref> By 1845, the German chemist [[August Wilhelm von Hofmann]] and his student [[John Buddle Blyth]] had determined styrene's [[empirical formula]]: C<sub>8</sub>H<sub>8</sub>.<ref> See: * {{cite journal |last1=Blyth |first1=John |last2=Hofmann |first2=Aug. Wilhelm |title=On styrole, and some of the products of its decomposition |journal=Memoirs and Proceedings of the Chemical Society of London |date=1845a |volume=2 |pages=334–358 |url=https://books.google.com/books?id=7yFbAAAAYAAJ&pg=PA334 |url-status=live |archive-url=https://web.archive.org/web/20180501152357/https://books.google.com/books?id=7yFbAAAAYAAJ&lpg=PA334&pg=PA334 |archive-date=1 May 2018|doi=10.1039/mp8430200334}}; see p. 339. * Reprinted in: {{cite journal |last1=Blyth |first1=John |last2=Hofmann |first2=Aug. Wilhelm |title=On styrole, and some of the products of its decomposition |journal=Philosophical Magazine |date=August 1845b |volume=27 |issue=178 |pages=97–121 |url=https://babel.hathitrust.org/cgi/pt?id=umn.319510006140796;view=1up;seq=117 |series=3rd series |doi=10.1080/14786444508645234}}; see p. 102. * German translation: {{cite journal |last1=Blyth |first1=John |last2=Hofmann |first2=Aug. Wilh. |title=Ueber das Styrol und einige seiner Zersetzungsproducte |journal=Annalen der Chemie und Pharmacie |date=1845c |volume=53 |issue=3 |pages=289–329 |url=https://books.google.com/books?id=A8MwAAAAYAAJ&pg=PA289 |trans-title=On styrol and some of its decomposition products |language=de |doi=10.1002/jlac.18450530302}}; see p. 297. * Note that Blyth and Hofmann state the empirical formula of styrene as C<sub>16</sub>H<sub>8</sub> because at that time, some chemists used the wrong atomic mass for carbon (6 instead of 12).</ref> They had also determined that Simon's "styrol oxide"—which they renamed "metastyrol"—had the same [[empirical formula]] as styrene.<ref>(Blyth and Hofmann, 1845a), p. 348. From p. 348: "Analysis as well as synthesis has equally proved that styrol and the vitreous mass (for which we propose the name of metastyrol) possess the same constitution per cent."</ref> Furthermore, they could obtain styrene by [[Dry distillation|dry-distilling]] "metastyrol".<ref>(Blyth and Hofmann, 1845a), p. 350</ref> In 1865, the German chemist [[Emil Erlenmeyer]] found that styrene could form a [[Dimer (chemistry)|dimer]],<ref>Erlenmeyer, Emil (1865) [https://babel.hathitrust.org/cgi/pt?id=uva.x002457969;view=1up;seq=134 "Ueber Distyrol, ein neues Polymere des Styrols"] (On distyrol, a new polymer of styrol), ''Annalen der Chemie'', '''135''' : 122–123.</ref> and in 1866 the French chemist [[Marcelin Berthelot]] stated that "metastyrol" was a [[polymer]] of styrene (i.e. [[polystyrene]]).<ref>Berthelot, M. (1866) [https://archive.org/stream/bulletin27frangoog#page/n295/mode/2up "Sur les caractères de la benzine et du styrolène, comparés avec ceux des autres carbures d'hydrogène"] (On the characters of [[benzene]] and styrene, compared with those of other hydrocarbons), ''Bulletin de la Société Chimique de Paris'', 2nd series, '''6''' : 289–298. From p. 294: ''"On sait que le styrolène chauffé en vase scellé à 200°, pendant quelques heures, se change en un polymère résineux (métastyrol), et que ce polymère, distillé brusquement, reproduit le styrolène."'' (One knows that styrene [when] heated in a sealed vessel at 200 °C, for several hours, is changed into a resinous polymer (metastyrol), and that this polymer, [when] distilled abruptly, reproduces styrene.)</ref> Meanwhile, other chemists had been investigating another component of storax, namely, [[cinnamic acid]]. They had found that cinnamic acid could be [[decarboxylated]] to form "cinnamene" (or "cinnamol"), which appeared to be styrene. In 1845, French chemist [[Emil Kopp]] suggested that the two compounds were identical,<ref>Kopp, E. (1845), [http://gallica.bnf.fr/ark:/12148/bpt6k6449135m/f38.item.zoom "Recherches sur l'acide cinnamique et sur le cinnamène"] {{webarchive |url=https://web.archive.org/web/20161108062615/http://gallica.bnf.fr/ark:/12148/bpt6k6449135m/f38.item.zoom |date=8 November 2016}} (Investigations of cinnamic acid and cinnamen), ''Comptes rendus'', '''21''' : 1376–1380. From p. 1380: ''"Je pense qu'il faudra désormais remplacer le mot de styrol par celui de cinnamène, et le métastyrol par le métacinnamène."'' (I think that henceforth one will have to replace the word "styrol" with that of "cinnamène", and "metastyrol" with "metacinnamène".)</ref> and in 1866, Erlenmeyer suggested that both "cinnamol" and styrene might be vinylbenzene.<ref>Erlenmeyer, Emil (1866) [https://babel.hathitrust.org/cgi/pt?id=uva.x002457970;view=1up;seq=339 "Studien über die s.g. aromatischen Säuren"] (Studies of the so-called aromatic acids), ''Annalen der Chemie'', '''137''' : 327–359; [https://babel.hathitrust.org/cgi/pt?id=uva.x002457970;view=1up;seq=365 see p. 353.]</ref> However, the styrene that was obtained from cinnamic acid seemed different from the styrene that was obtained by distilling storax resin: the latter was [[Optical rotation|optically active]].<ref>{{cite journal |last1=Berthelot |first1=Marcellin |title=Sur les états isomériques du styrolène |journal=Annales de Chimie et de Physique |date=1867 |volume=12 |pages=159–161 |url=https://babel.hathitrust.org/cgi/pt?id=uva.x002489147;view=1up;seq=165 |series=4th series |trans-title=On the isomeric states of styrene |language=fr}} From p. 160: ''"1° Le carbure des cinnamates est privé de pouvoir rotatoire, tandis que le carbure du styrax dévie de 3 degrés la teinte de passage (l = 100 mm)."'' (1. The carbon [atom] of cinnamates is bereft of rotary power [i.e., the ability to rotate polarized light], whereas the carbon of styrax deflects by 3 degrees the neutral tint [i.e., the relative orientation of the polarized quartz plates at which the light through the polarimeter appears colorless] (length = 100 mm). [For further details about 19th century polarimeters, see: {{cite book |last1=Spottiswode |first1=William |title=Polarisation of Light |date=1883 |publisher=[[Macmillan and Co.]] |location=London |pages=51–52 |edition=4th |url=https://archive.org/stream/polarisationofli00spotrich |access-date=15 September 2016 |archive-url=https://web.archive.org/web/20100910214825/http://www.archive.org/stream/polarisationofli00spotrich#page/52/mode/2up/ |archive-date=10 September 2010 |url-status=dead}}])</ref> Eventually, in 1876, the Dutch chemist [[Jacobus Henricus van 't Hoff|van 't Hoff]] resolved the ambiguity: the optical activity of the styrene that was obtained by distilling storax resin was due to a contaminant.<ref>van 't Hoff, J. H. (1876) [https://babel.hathitrust.org/cgi/pt?id=uiug.30112025695146;view=1up;seq=13 "Die Identität von Styrol und Cinnamol, ein neuer Körper aus Styrax"] (The identity of styrol and cinnamol, a new substance from styrax), ''Berichte der deutschen chemischen Gesellschaft'', '''9''' : 5-6.</ref>
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