Editing Ethanol (section)

== History ==
{{Further|Liquor}}<!--
[[File:Alcohol flame.jpg|thumb|upright|Ethanol being used as fuel for a burner]]-->

The fermentation of sugar into ethanol is one of the earliest [[biotechnology|biotechnologies]] employed by humans. Ethanol has historically been identified variously as spirit of wine or ardent spirits,<ref>{{Cite book | last=Ottley | first=William Campbell | url=https://books.google.com/books?id=wYcwvwyk2RAC | title=A dictionary of chemistry and of mineralogy as connected with it | date=1826 | publisher=Murray | language=en}}</ref> and as [[aqua vitae]] or aqua vita. The intoxicating effects of its consumption have been known since ancient times. Ethanol has been used by humans since prehistory as the intoxicating ingredient of alcoholic beverages. Dried residue on 9,000-year-old pottery found in China suggests that [[Neolithic]] people consumed alcoholic beverages.<ref name="Roach">{{cite journal | vauthors=Roach J | date=18 July 2005 | url=http://news.nationalgeographic.com/news/2005/07/0718_050718_ancientbeer.html | archive-url=https://web.archive.org/web/20050722030635/http://news.nationalgeographic.com/news/2005/07/0718_050718_ancientbeer.html | url-status=dead | archive-date=22 July 2005 | title=9,000-Year-Old Beer Re-Created From Chinese Recipe | journal=National Geographic News | access-date=3 September 2007}}</ref>

The inflammable nature of the exhalations of wine was already known to ancient natural philosophers such as [[Aristotle]] (384–322 BCE), [[Theophrastus]] ({{circa|371}}–287 BCE), and [[Pliny the Elder]] (23/24–79 CE).<ref>{{harvnb|Berthelot|Houdas|1893|loc=vol. I, p. 137}}.</ref> However, this did not immediately lead to the isolation of ethanol, despite the development of more advanced distillation techniques in second- and third-century [[Roman Egypt]].<ref>{{harvnb|Berthelot|Houdas|1893|loc=vol. I, pp. 138–139}}.</ref> An important recognition, first found in one of the writings attributed to [[Jabir ibn Hayyan|Jābir ibn Ḥayyān]] (ninth century CE), was that by [[Salt-effect distillation|adding salt]] to boiling wine, which increases the wine's [[relative volatility]], the flammability of the resulting vapors may be enhanced.<ref>{{cite book | last1=al-Hassan | first1=Ahmad Y. | author-link=Ahmad Y. al-Hassan | year=2009 | chapter=Alcohol and the Distillation of Wine in Arabic Sources from the 8th Century | title=Studies in al-Kimya': Critical Issues in Latin and Arabic Alchemy and Chemistry | location=Hildesheim | publisher=Georg Olms Verlag | pages=283–298}} (same content also available on [http://www.history-science-technology.com/notes/notes7.html the author's website] {{Webarchive|url=https://web.archive.org/web/20151229003135/http://www.history-science-technology.com/notes/notes7.html |date=29 December 2015 }}).</ref> The distillation of wine is attested in Arabic works attributed to [[Al-Kindi|al-Kindī]] ({{circa|801}}–873 CE) and to [[Al-Farabi|al-Fārābī]] ({{circa|872}}–950), and in the 28th book of [[Al-Zahrawi|al-Zahrāwī]]'s (Latin: Abulcasis, 936–1013) ''Kitāb al-Taṣrīf'' (later translated into Latin as ''Liber servatoris'').<ref>{{harvnb|al-Hassan|2009}} (same content also available on [http://www.history-science-technology.com/notes/notes7.html the author's website] {{Webarchive|url=https://web.archive.org/web/20151229003135/http://www.history-science-technology.com/notes/notes7.html |date=29 December 2015 }}); cf. {{harvnb|Berthelot|Houdas|1893|loc=vol. I, pp. 141, 143}}. Sometimes, sulfur was also added to the wine (see {{harvnb|Berthelot|Houdas|1893|loc=vol. I, p. 143}}).</ref> In the twelfth century, recipes for the production of ''aqua ardens'' ("burning water", i.e., ethanol) by distilling wine with salt started to appear in a number of Latin works, and by the end of the thirteenth century it had become a widely known substance among Western European chemists.<ref>{{harvnb|Multhauf|1966|pp=204–206}}.</ref>

The works of [[Taddeo Alderotti]] (1223–1296) describe a method for concentrating ethanol involving repeated fractional distillation through a water-cooled [[still]], by which an ethanol purity of 90% could be obtained.<ref>{{cite book | last1=Holmyard | first1=Eric John | author1-link=Eric John Holmyard | date=1957 | title=Alchemy | location=Harmondsworth | publisher=Penguin Books | isbn=978-0-486-26298-7}} pp. 51–52.</ref> The medicinal properties of ethanol were studied by [[Arnald of Villanova]] (1240–1311 CE) and [[John of Rupescissa]] ({{circa|1310}}–1366), the latter of whom regarded it as a life-preserving substance able to prevent all diseases (the ''aqua vitae'' or "water of life", also called by John the ''[[Aether (classical element)|quintessence]]'' of wine).<ref>{{cite book | last=Principe | first=Lawrence M. | author-link=Lawrence M. Principe | year=2013 | title=The Secrets of Alchemy | location=Chicago | publisher=The University of Chicago Press | isbn=978-0-226-10379-2}} pp. 69–71.</ref> In [[China]], archaeological evidence indicates that the true distillation of alcohol began during the [[Jin dynasty (1115–1234)|Jin]] (1115–1234) or [[Southern Song dynasty|Southern Song]] (1127–1279) dynasties.<ref name=haw>{{cite book | last=Haw | first=Stephen G. | name-list-style=vanc | author-link=Stephen G. Haw | title=Marco Polo in China | publisher=Routledge | year=2006 | isbn=978-1-134-27542-7 | chapter=Wine, women and poison | pages=147–148 | chapter-url={{google books | plainurl=y | id=DSfvfr8VQSEC | page=148}} | access-date=10 July 2016 | quote=The earliest possible period seems to be the Eastern Han dynasty... the most likely period for the beginning of true distillation of spirits for drinking in China is during the Jin and Southern Song dynasties}}</ref> A still has been found at an archaeological site in Qinglong, [[Hebei]], dating to the 12th century.<ref name="haw" /> In India, the true distillation of alcohol was introduced from the Middle East, and was in wide use in the [[Delhi Sultanate]] by the 14th century.<ref name="habib">{{cite book | last=Habib | first=Irfan | author-link=Irfan Habib | title=Economic History of Medieval India, 1200–1500 | url={{google books | plainurl=y | id=K8kO4J3mXUAC | page=55}} | year=2011 | publisher=Pearson Education India | isbn=978-81-317-2791-1 | pages=55–}}</ref>

In 1796, German-Russian chemist [[Johann Tobias Lowitz]] obtained pure ethanol by mixing partially purified ethanol (the alcohol-water azeotrope) with an excess of anhydrous alkali and then distilling the mixture over low heat.<ref>{{cite journal | last=Lowitz | first=T. | name-list-style=vanc | journal=Chemische Annalen für die Freunde der Naturlehre, Aerznengelartheit, Haushaltungskunde und Manufakturen | url={{google books | plainurl=y | id=Zws_AAAAcAAJ}} | year=1796 | title=Anzeige eines, zur volkommen Entwasserung des Weingeistes nothwendig zu beobachtenden, Handgriffs | language=de | trans-title=Report of a task that must be done for the complete dehydration of wine spirits [i.e., alcohol-water azeotrope]) | volume=1 | pages=195–204 | quote=See pp. 197–198: Lowitz dehydrated the azeotrope by mixing it with a 2:1 excess of anhydrous alkali and then distilling the mixture over low heat.}}</ref> French chemist [[Antoine Lavoisier]] described ethanol as a compound of carbon, hydrogen, and oxygen, and in 1807 [[Nicolas-Théodore de Saussure]] determined ethanol's chemical formula.<ref>{{cite EB1911|wstitle = Alcohol|volume=1|pages=525–527}}</ref><ref>{{cite journal | last=de Saussure | first=Théodore | name-list-style=vanc | journal=Journal de Physique, de Chimie, d'Histoire Naturelle et des Arts | url={{google books | plainurl=y | id=G-UPAAAAQAAJ | page=316}} | year=1807 | title=Mémoire sur la composition de l'alcohol et de l'éther sulfurique | volume=64 | pages=316–354}} In his 1807 paper, Saussure determined ethanol's composition only roughly; a more accurate analysis of ethanol appears on page 300 of his 1814 paper: {{cite journal | last=de Saussure | first=Théodore | journal=Annales de Chimie et de Physique | url={{google books | plainurl=y | id=ch8zAQAAMAAJ | page=273}} | year=1814 | pages=273–305 | title=Nouvelles observations sur la composition de l'alcool et de l'éther sulfurique | volume=89}}</ref> Fifty years later, [[Archibald Scott Couper]] published the structural formula of ethanol,  one of the first structural formulas determined.<ref name="Couper">{{cite journal | vauthors=Couper AS | year=1858 | title=On a new chemical theory | journal=Philosophical Magazine | format=online reprint | volume=16 | issue=104–116 | url=http://web.lemoyne.edu/~giunta/couper/couper.html | access-date=3 September 2007}}</ref>

Ethanol was first prepared synthetically in 1825 by [[Michael Faraday]]. He found that sulfuric acid could absorb large volumes of [[coal gas]].<ref>{{cite journal | vauthors=Faraday M | year=1825 | url=http://gallica.bnf.fr/ark:/12148/bpt6k559209/f473.image | title=On new compounds of carbon and hydrogen, and on certain other products obtained during the decomposition of oil by heat | journal=Philosophical Transactions of the Royal Society of London | volume=115 | pages=440–466 | doi=10.1098/rstl.1825.0022 | doi-access=free}} In a footnote on page 448, Faraday notes the action of sulfuric acid on coal gas and coal-gas distillate; specifically, "The [sulfuric] acid combines directly with carbon and hydrogen; and I find when [the resulting compound is] united with bases [it] forms a peculiar class of salts, somewhat resembling the sulphovinates [i.e., ethyl sulfates], but still different from them."</ref> He gave the resulting solution to [[Henry Hennell]], a British chemist, who found in 1826 that it contained "sulphovinic acid" (ethyl hydrogen sulfate).<ref>{{cite journal | vauthors=Hennell H | journal=Philosophical Transactions of the Royal Society of London | url={{google books | plainurl=y | id=f05FAAAAcAAJ | page=}} | year=1826 | title=On the mutual action of sulphuric acid and alcohol, with observations on the composition and properties of the resulting compound | volume=116 | pages=240–249 | doi=10.1098/rstl.1826.0021 | s2cid=98278290}} On page 248, Hennell mentions that Faraday gave him some sulfuric acid in which coal gas had dissolved and that he (Hennell) found that it contained "sulphovinic acid" (ethyl hydrogen sulfate).</ref> In 1828, Hennell and the French chemist [[Georges-Simon Serullas]] independently discovered that sulphovinic acid could be decomposed into ethanol.<ref name="Hennell">{{cite journal | vauthors=Hennell H | year=1828 | title=On the mutual action of sulfuric acid and alcohol, and on the nature of the process by which ether is formed | journal=Philosophical Transactions of the Royal Society of London | volume=118 | url={{google books | plainurl=y | id=X-9FAAAAMAAJ | page=365}} | doi=10.1098/rstl.1828.0021 | pages=365–371 | s2cid=98483646}} On page 368, Hennell produces ethanol from "sulfovinic acid" ([[Ethyl sulfate|ethyl hydrogen sulfate]]).</ref><ref>{{cite journal | last=Sérullas | first=Georges-Simon | editor-first1=Louis-Bernard | editor-last1=Guyton de Morveau | editor-first2=Joseph Louis | editor-last2=Gay-Lussac | editor-first3=François | editor-last3=Arago | editor4=Michel Eugène Chevreul | editor5=Marcellin Berthelot | editor6=Éleuthère Élie Nicolas Mascart | editor7=Albin Haller | name-list-style=vanc | journal=Annales de Chimie et de Physique | url={{google books | plainurl=y | id=ZxUAAAAAMAAJ | page=152}} | year=1828 | title=De l'action de l'acide sulfurique sur l'alcool, et des produits qui en résultent | volume=39 | pages=152–186}} On page 158, Sérullas mentions the production of alcohol from "sulfate acid d'hydrogène carboné" (hydrocarbon acid sulfate).</ref> Thus, in 1825 Faraday had unwittingly discovered that ethanol could be produced from ethylene (a component of coal gas) by [[Acid catalysis|acid-catalyzed]] hydration, a process similar to current industrial ethanol synthesis.<ref>In 1855, the French chemist [[Marcellin Berthelot]] confirmed Faraday's discovery by preparing ethanol from pure ethylene. {{cite journal | first=Marcellin | last=Berthelot | editor-first1=François | editor-last1=Arago | editor-first2=Joseph Louis | editor-last2=Gay-Lussac | name-list-style=vanc | journal=Annales de Chimie et de Physique | url={{google books | plainurl=y | id=1ClCAAAAcAAJ | page=385}} | year=1855 | title=Sur la formation de l'alcool au moyen du bicarbure d'hydrogène (On the formation of alcohol by means of ethylene) | volume=43 | pages=385–405}} (Note: The chemical formulas in Berthelot's paper are wrong because chemists at that time used the wrong atomic masses for the elements; e.g., carbon (6 instead of 12), oxygen (8 instead of 16), etc.)</ref>

Ethanol was used as lamp fuel in the U.S. as early as 1840, but a tax levied on industrial alcohol during the [[American Civil War|Civil War]] made this use uneconomical. The tax was repealed in 1906.<ref name="siegel">{{cite news | url=https://www.npr.org/templates/story/story.php?storyId=7426827 | title=Ethanol, Once Bypassed, Now Surging Ahead | last=Siegel | first=Robert | name-list-style=vanc | publisher=NPR | date=15 February 2007 | access-date=22 September 2007}}</ref> Use as an automotive fuel dates back to 1908, with the [[Ford Model T]] able to run on [[petrol]] (gasoline) or ethanol.<ref name="dipardo">{{cite web | url=http://www.eia.gov/oiaf/analysispaper/pdf/biomass.pdf | title=Outlook for Biomass Ethanol Production and Demand | publisher=United States Department of Energy | last=DiPardo | first=Joseph | name-list-style=vanc | access-date=22 September 2007 | url-status=dead | archive-url=https://web.archive.org/web/20150924050511/http://www.eia.gov/oiaf/analysispaper/pdf/biomass.pdf | archive-date=24 September 2015 | df=dmy-all}}</ref> It fuels some [[spirit lamps]].

Ethanol intended for industrial use is often produced from ethylene.<ref name="myers">{{Cite book | last1=Myers | first1=Richard L. | last2=Myers | first2=Rusty L. | name-list-style=vanc | title=The 100 most important chemical compounds: a reference guide | year=2007 | publisher=Greenwood Press | location=Westport, CN | isbn=978-0-313-33758-1 | page=122 | url={{google books | plainurl=y | id=0AnJU-hralEC | page=122}}}}</ref> Ethanol has widespread use as a solvent of substances intended for human contact or consumption, including scents, flavorings, colorings, and medicines. In chemistry, it is both a solvent and a feedstock for the synthesis of other products. It has a long history as a fuel for heat and light, and more recently as a fuel for internal combustion engines.