Editing Chloroform (section)

==History==
Chloroform was synthesized independently by several investigators {{Circa|1831}}:
*Moldenhawer, a German pharmacist from [[Frankfurt an der Oder]], appears to have produced chloroform in 1830 by mixing [[chlorinated lime#Chlorine-based bleaches|chlorinated lime]] with [[ethanol]]; however, he mistook it for ''Chloräther'' (chloric ether, [[1,2-dichloroethane]]).<ref>{{cite journal|last=Moldenhawer|date=1830|url=https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222|title=Verfahren den Spiritus von dem Fuselöl auf leichte Weise zu befreien|trans-title=Procedure for freeing ethanol of fusel oil in an easy way|journal=Magazin für Pharmacie|volume=8|issue=31|pages=222–227|access-date=6 May 2016|archive-date=29 July 2020|archive-url=https://web.archive.org/web/20200729120000/https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222|url-status=live}}</ref><ref>{{cite journal|last1=Defalque|first1=Ray J.|last2=Wright|first2=A. J. |title=Was chloroform produced before 1831?|journal=Anesthesiology|volume=92|issue=1|pages=290–291|pmid=10638939|year=2000|doi=10.1097/00000542-200001000-00060|doi-access=free}}</ref>
*[[Samuel Guthrie (physician)|Samuel Guthrie]], a U.S. physician from [[Sackets Harbor, New York]], also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol, and noted its [[Anesthetic|anaesthetic]] properties; however, he also believed that he had prepared chloric ether.<ref>{{cite journal|last=Guthrie|first=Samuel|year=1832|url=https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64|title=New mode of preparing a spirituous solution of chloric ether|journal=The American Journal of Science and Arts|volume=21|pages=64–65 and 405–408|access-date=6 May 2016|archive-date=29 July 2020|archive-url=https://web.archive.org/web/20200729135541/https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64|url-status=live}}</ref><ref>{{cite book|last=Guthrie|first=Ossian|date=1887|url=https://archive.org/details/39002011125375.med.yale.edu|page=[https://archive.org/details/39002011125375.med.yale.edu/page/n43 1]|title=Memoirs of Dr. Samuel Guthrie, and the History of the Discovery of Chloroform|location=Chicago|publisher=George K. Hazlitt & Co.}}</ref><ref>{{cite book|last=Stratmann|first=Linda|date=2003|title=Chloroform: The Quest for Oblivion|location=Stroud|publisher=Sutton Publishing|chapter-url=https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30|chapter=Chapter 2|isbn=978-0-7524-9931-4|access-date=6 May 2016|archive-date=29 July 2020|archive-url=https://web.archive.org/web/20200729120316/https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30|url-status=live}}</ref>
*[[Justus von Liebig]] carried out the [[Bond cleavage|alkaline cleavage]] of [[chloral]]. Liebig incorrectly states that the [[empirical formula]] of chloroform was {{chem2|C2Cl5}} and named it "''Chlorkohlenstoff''" ("carbon chloride").<ref>{{cite journal|last=Liebig|first=Justus von|url=https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462|doi=10.1002/andp.18310991111|title=Ueber die Zersetzung des Alkohols durch Chlor|journal=Annalen der Physik und Chemie|volume=99|issue=11|page=444|trans-title=On the decomposition of alcohol by chlorine|year=1831|bibcode=1831AnP....99..444L|access-date=6 May 2016|archive-date=10 May 2017|archive-url=https://web.archive.org/web/20170510154137/https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462|url-status=live}}</ref><ref>{{cite journal|last=Liebig |first=Justus von |url=https://babel.hathitrust.org/cgi/pt?id=wu.89048351662&view=1up&seq=861 |year=1832|title=Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen|journal=Annalen der Physik und Chemie |volume=100 |issue=2 |pages=243–295 |trans-title=On the compounds which arise by the reaction of chlorine with alcohol [ethanol], ether [diethyl ether], oil-forming gas [ethylene], and spirit of vinegar [acetone] |doi=10.1002/andp.18321000206|bibcode=1832AnP...100..243L }}<br />On pages 259–265, Liebig describes ''Chlorkohlenstoff'' ("carbon chloride", chloroform), but on p. 264, Liebig incorrectly states that the [[empirical formula]] of chloroform is C<sub>2</sub>Cl<sub>5</sub>.</ref>
*[[Eugène Soubeiran]] obtained the compound by the action of [[chlorine bleach]] on both [[ethanol]] and [[acetone]].<ref>{{cite journal |last=Soubeiran |first=Eugène |date=1831 |url=https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115 |title=Recherches sur quelques combinaisons du chlore |trans-title=Investigations into some compounds of chlorine |journal=Annales de Chimie et de Physique |series=Série 2 |volume=48 |pages=113–157 |access-date=6 May 2016 |archive-date=10 May 2017 |archive-url=https://web.archive.org/web/20170510154147/https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115 |url-status=live }}
*Reprinted in {{cite journal |last=Soubeiran |first=Eugène |date=1831 |url=https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657 |title=Recherches sur quelques combinaisons du chlore |trans-title=Investigations on some compounds of chlorine |journal=Journal de Pharmacie et des Sciences Accessoires |volume=17 |pages=657–672 |access-date=6 May 2016 |archive-date=29 July 2020 |archive-url=https://web.archive.org/web/20200729112744/https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657 |url-status=live }}
*Reprinted in {{cite journal |last=Soubeiran |first=Eugène |date=1832 |url=https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1 |title=Suite des recherches sur quelques combinaisons du chlore |trans-title=Continuation of investigations on some compounds of chlorine |journal=Journal de Pharmacie et des Sciences Accessoires |volume=18 |pages=1–24 |access-date=6 May 2016 |archive-date=29 July 2020 |archive-url=https://web.archive.org/web/20200729121309/https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1 |url-status=live }}</ref>

In 1834, French chemist [[Jean-Baptiste Dumas]] determined chloroform's empirical formula and named it:<ref>{{cite journal|last=Dumas |first=J.-B. |date=1834 |title=Récherches rélative à l'action du chlore sur l'alcool |trans-title=Experiments regarding the action of chlorine on alcohol |journal=L'Institut, Journal Général des Sociétés et Travaux Scientifiques de la France et de l'Étranger |volume=2 |pages=106–108 and 112–115}}
*Reprinted in {{cite journal|url=https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668|title=Untersuchung über die Wirkung des Chlors auf den Alkohol|journal=Annalen der Physik und Chemie|volume=107|issue=42|pages=657–673|trans-title=Investigation of the action of chlorine on alcohol|doi=10.1002/andp.18341074202|bibcode=1834AnP...107..657D|year=1834|last1=Dumas|first1=J.-B.|access-date=12 May 2016|archive-date=10 May 2017|archive-url=https://web.archive.org/web/20170510152609/https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668|url-status=live}}<br />On p. 653, Dumas states chloroform's empirical formula:
::''"Es scheint mir also erweisen, dass die von mir analysirte Substance, … zur Formel hat: {{chem2|C2H2Cl6}}."'' (Thus it seems to me to show that the substance [that was] analyzed by me … has as [its empirical] formula: {{chem2|C2H2Cl6}}.) [Note: The coefficients of his empirical formula must be halved.]
:Dumas then notes that chloroform's simple [[empirical formula]] resembles that of [[formic acid]]. Furthermore, if chloroform is boiled with [[potassium hydroxide]], one of the products is [[potassium formate]]. On p. 654, Dumas names chloroform: 
::''"Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen."'' (This caused me to bestow this substance with the name "chloroform" [i.e., formyl chloride or chloride of formic acid].)
*Reprinted in {{cite journal |doi=10.1002/jlac.18350160213 |url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542 |title=Ueber die Wirkung des Chlors auf den Alkohol |journal=Annalen der Pharmacie |volume=16 |issue=2 |pages=164–171 |trans-title=On the action of chlorine on alcohol |year=1835 |last1=Dumas |first1=J.-B. |access-date=12 May 2016 |archive-date=10 May 2017 |archive-url=https://web.archive.org/web/20170510152601/https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542 |url-status=live }}</ref> "''Es scheint mir also erweisen, dass die von mir analysirte Substanz, … zur Formel hat: C<sub>2</sub>H<sub>2</sub>Cl<sub>6</sub>.''" (Thus it seems to me to show that the substance I analyzed … has as [its empirical] formula: C<sub>2</sub>H<sub>2</sub>Cl<sub>6</sub>.). [Note: The coefficients of his empirical formula should be halved.] ... "''Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen.''" (This had caused me to impose the name "chloroform" upon this substance [i.e., formyl chloride or chloride of formic acid].)

In 1835, Dumas prepared the substance by alkaline cleavage of [[trichloroacetic acid]]. 

In 1842, [[Robert Mortimer Glover]] in London discovered the anaesthetic qualities of chloroform on laboratory animals.<ref name=pdf1>{{cite journal|pmid=15023112|url=http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf|year=2004|last1=Defalque|first1=R. J.|title=The short, tragic life of Robert M. Glover|journal=Anaesthesia|volume=59|issue=4|pages=394–400|last2=Wright|first2=A. J.|doi=10.1111/j.1365-2044.2004.03671.x|s2cid=46428403|url-status=live|archive-url=https://web.archive.org/web/20160309080158/http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf|archive-date=9 March 2016|doi-access=free}}</ref>

In 1847, Scottish obstetrician [[James Y. Simpson]] was the first to demonstrate the anaesthetic properties of chloroform (provided by local pharmacist [[William Flockhart]] of Duncan, Flockhart and company,<ref name="Gordon2002" />) in humans, and helped to popularize the drug for use in medicine.<ref name=eb>{{cite encyclopedia|title=Sir James Young Simpson|url=https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet|encyclopedia=Encyclopædia Britannica|access-date=23 August 2013|url-status=live|archive-url=https://web.archive.org/web/20130727130133/https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet|archive-date=27 July 2013}}</ref> 

By the 1850s, chloroform was being produced on a commercial basis. In Britain, about 750,000 doses a week were being produced by 1895,<ref>{{Cite journal|last=Worling|first=P.M.|date=1998|title=Duncan and Flockhart: the Story of Two Men and a Pharmacy|journal=Pharmaceutical Historian|volume=28|issue=2|pages=28–33|pmid=11620310}}</ref> using the Liebig procedure, which retained its importance until the 1960s. Today, chloroform – along with [[dichloromethane]] – is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane.<ref name="Ullmann"/>