Editing Methanol (section)

==History==<!-- This section is linked from [[Methyl group]] -->
In their [[embalming]] process, the [[ancient Egyptians]] used a mixture of substances, including methanol, which they obtained from the [[pyrolysis]] of wood. Pure methanol, however, was first isolated in 1661 by [[Robert Boyle]], when he produced it via the distillation of [[buxus]] (boxwood).<ref>Boyle discusses the distillation of liquids from the wood of the box shrub in: Robert Boyle, ''The Sceptical Chymist'' (London, England: J. Cadwell, 1661), [https://archive.org/stream/scepticalchymis00BoylA#page/192/mode/2up/ pp. 192–195].</ref> It later became known as "pyroxylic spirit". In 1834, the French chemists [[Jean-Baptiste Dumas]] and [[Eugene Peligot]] determined its elemental composition.<ref name=Dumas>A report on methanol to the French Academy of Sciences by J. Dumas and E. Péligot began during the Academy's meeting of 27 October 1834 and finished during the meeting of 3 November 1834. See: ''Procès-verbaux des séances de l'Académie'', '''10''' : 600–601. Available on: [http://gallica.bnf.fr/ark:/12148/bpt6k33037/f606.image Gallica] {{Webarchive|url=https://web.archive.org/web/20150425033225/http://gallica.bnf.fr/ark:/12148/bpt6k33037/f606.image |date=25 April 2015}}. The complete report appears in: J. Dumas and E. Péligot (1835) [{{google books |plainurl=y |id=xSs8oDQV4uYC&|page=44}} "Mémoire sur l'espirit de bois et sur les divers composés ethérés qui en proviennent"] (Memoir on spirit of wood and on the various ethereal compounds that derive therefrom), ''Annales de chimie et de physique'', '''58''' : 5–74; from [{{google books |plainurl=y |id=94c5AAAAcAAJ|page=9}} page 9]: ''Nous donnerons le nom de ''méthylène'' (1) à un radical ... (1) Μεθυ, vin, et υλη, bois; c'est-à-dire vin ou liqueur spiritueuse du bois.'' (We will give the name methylene (1) to a radical ... (1) ''methy'', wine, and ''hulē'', wood; that is, wine or spirit of wood.)</ref>

They also introduced the word "methylène" to organic chemistry, forming it from [[Greek language|Greek]] ''[[wiktionary:μέθυ#Ancient Greek|methy]]'' = "alcoholic liquid" + ''[[wiktionary:ὕλη#Ancient Greek|hȳlē]]'' = "forest, wood, timber, material". "Methylène" designated a [[Radical theory|"radical"]] that was about 14% hydrogen by weight and contained one carbon atom. This would be {{chem2|CH2}}, but at the time carbon was thought to have an [[atomic weight]] only six times that of hydrogen, so they gave the formula as CH.<ref name=Dumas/> They then called wood alcohol (l'esprit de bois) "bihydrate de méthylène" (bihydrate because they thought the formula was {{chem2|C4H8O4}} or {{chem2|(CH)4(H2O)2}}). The term "methyl" was derived in about 1840 by [[back-formation]] from "methylene", and was then applied to describe "methyl alcohol". This was shortened to "methanol" in 1892 by the [[IUPAC nomenclature|International Conference on Chemical Nomenclature]].<ref>For a report on the International Conference on Chemical Nomenclature that was held in April 1892 in Geneva, Switzerland, see:
* {{cite journal|doi=10.1038/046056c0|url={{google books |plainurl=y |id=LHkCAAAAIAAJ|page=5}}|title=The International Conference on Chemical Nomenclature|journal=Nature|volume=46|issue=1177|pages=56–9|last=Armstrong|first= Henry E|year=1892|bibcode=1892Natur..46...56A|doi-access=free}}
* Armstrong's report is reprinted with the resolutions in English in: {{cite journal|author= Armstrong, Henry |year=1892|url={{google books |plainurl=y |id=RogMAQAAIAAJ|page=398}}|title=The International Conference on Chemical Nomenclature|journal=The Journal of Analytical and Applied Chemistry|volume=6|issue=1177|pages=390–400|quote=p. 398: 15. The alcohols and the phenols are named after the hydrocarbon from which they derive, terminated with the suffix ''ol'' (ex. pentanol, pentenol, etc.). |bibcode=1892Natur..46...56A|doi=10.1038/046056c0|doi-access=free}}</ref> The [[suffix (linguistics)|suffix]] [[-yl]], which, in [[organic chemistry]], forms names of [[carbon]] groups, is from the word ''methyl''.

French chemist [[Paul Sabatier (chemist)|Paul Sabatier]] presented the first [[Sabatier reaction|process]] that could be used to produce methanol synthetically in 1905. This process suggested that carbon dioxide and hydrogen could be reacted to produce methanol.<ref name=":1" /> German chemists [[Alwin Mittasch]] and Mathias Pier, working for [[BASF|Badische-Anilin & Soda-Fabrik]] (BASF), developed a means to convert [[syngas|synthesis gas]] (a mixture of [[carbon monoxide]], [[carbon dioxide]], and [[hydrogen]]) into methanol and received a patent. According to Bozzano and Manenti, BASF's process was first utilized in [[Leuna]], Germany in 1923. Operating conditions consisted of "high" temperatures (between 300 and 400&nbsp;°C) and pressures (between 250 and 350 atm) with a [[zinc oxide|zinc]]/[[chromium(III) oxide|chromium oxide]] catalyst.<ref name=":10" />

US patent 1,569,775 was applied for on 4 September 1924 and issued on 12 January 1926 to BASF;<ref>{{patent|US|1569775}}</ref>  the process used a [[chromium(III) oxide|chromium]] and [[manganese oxide]] [[catalyst]] with extremely vigorous conditions: pressures ranging from 50 to 220 [[atmosphere (unit)|atm]], and temperatures up to 450&nbsp;°C. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures. The modern low pressure methanol (LPM) process was developed by [[Imperial Chemical Industries|ICI]] in the late 1960s with the technology patent long since expired.<ref>{{patent|US|3326956}}</ref>

During [[World War II]], methanol was used as a fuel in several German military rocket designs, under the name [[List of stoffs|M-Stoff]], and in a roughly 50/50 mixture with [[hydrazine]], known as [[C-Stoff]].

The use of methanol as a motor fuel received attention during the [[1970s energy crisis|oil crises of the 1970s]]. By the mid-1990s, over 20,000 methanol [[flexible fuel vehicle]]s (FFVs) capable of operating on methanol or gasoline were introduced in the US. In addition, low levels of methanol were blended in gasoline fuels sold in Europe during much of the 1980s and early-1990s. Automakers stopped building methanol FFVs by the late-1990s, switching their attention to ethanol-fueled vehicles. While the methanol FFV program was a technical success, rising methanol pricing in the mid- to late-1990s during a period of slumping gasoline pump prices diminished interest in [[methanol fuel]]s.<ref>{{cite book|author1=Halderman, James D. |author2=Martin, Tony |title=Hybrid and alternative fuel vehicles|url={{google books |plainurl=y |id=LqgeAQAAIAAJ}}|year=2009|publisher=Pearson/Prentice Hall|isbn=978-0-13-504414-8}}</ref>

In the early 1970s, a process was developed by [[Mobil]] for [[Methanol to gasoline|producing gasoline]] fuel from methanol.<ref>{{cite web |url=https://ihsmarkit.com/pdf/RP282_toc_173824110917062932.pdf |title=Methanol to Gasoline: A Private Report by the Process Economics Program |author=Ronald Smith |date=1 December 2011 |access-date=4 December 2019 |archive-date=4 December 2019 |archive-url=https://web.archive.org/web/20191204144549/https://ihsmarkit.com/pdf/RP282_toc_173824110917062932.pdf |url-status=live}}</ref>

Between the 1960s and 1980s methanol emerged as a precursor to the feedstock chemicals acetic acid and [[acetic anhydride]]. These processes include the [[Monsanto acetic acid synthesis]], [[Cativa process]], and [[Monsanto process#Tennessee Eastman acetic anhydride process|Tennessee Eastman acetic anhydride process]].