Editing Chloroform (section)

==Production==
Industrially, chloroform is produced by heating a mixture of [[chlorine]] and either [[methyl chloride]] ({{chem2|CH3Cl}}) or [[methane]] ({{chem2|CH4}}).<ref name=Ullmann/> At 400–500&nbsp;°C, [[free radical halogenation]] occurs, converting these precursors to progressively more chlorinated compounds:
:{{chem2|CH4 + [[Chlorine|Cl2]] → CH3Cl + [[Hydrogen chloride|HCl]]}}
:{{chem2|CH3Cl + Cl2 → [[Dichloromethane|CH2Cl2]] + HCl}}
:{{chem2|CH2Cl2 + Cl2 → CHCl3 + HCl}}

Chloroform undergoes further chlorination to yield [[carbon tetrachloride]] ({{chem2|CCl4}}):
:{{chem2|CHCl3 + Cl2 → CCl4 + HCl}}

The output of this process is a mixture of the four chloromethanes: [[chloromethane]], [[methylene chloride]] (dichloromethane), trichloromethane (chloroform), and tetrachloromethane (carbon tetrachloride). These can then be separated by [[distillation]].<ref name=Ullmann/>

Chloroform may also be produced on a small scale via the [[haloform reaction]] between [[acetone]] and [[sodium hypochlorite]]:
:{{chem2|3 NaOCl + (CH3)2CO → CHCl3 + 2 [[Sodium hydroxide|NaOH]] + [[Sodium acetate|CH3COONa]]}}

===Deuterochloroform===
{{Main|Deuterated chloroform}}
[[Deuterated chloroform]] is an [[isotopologue]] of chloroform with a single [[deuterium]] atom. {{chem2|CDCl3}} is a common solvent used in [[NMR spectroscopy]]. Deuterochloroform is produced by the reaction of [[hexachloroacetone]] with [[heavy water]].<ref>{{cite journal |last1=Paulsen |first1=P. J. |last2=Cooke |first2=W. D. |title=Preparation of Deuterated Solvents for Nuclear Magnetic Resonance Spectrometry. |journal=Analytical Chemistry |date=1 September 1963 |volume=35 |issue=10 |page=1560 |doi=10.1021/ac60203a072}}</ref> The haloform process is now obsolete for production of ordinary chloroform. Deuterochloroform can also be prepared by reacting [[sodium deuteroxide]] with [[chloral hydrate]].<ref>{{cite journal|doi=10.1021/ja01314a058|title=Chloroform-d (Deuteriochloroform)1|journal=Journal of the American Chemical Society|volume=57|issue=11|pages=2236–2237|year=1935|last1=Breuer|first1=F. W.}}</ref><ref>{{cite journal|doi=10.1021/jo01030a526|title=A Convenient Preparation of Chloroform-d1|journal=The Journal of Organic Chemistry|volume=29|issue=7|pages=2045–2046|year=1964|last1=Kluger|first1=Ronald}}</ref>

===Inadvertent formation of chloroform===
The haloform reaction can also occur inadvertently in domestic settings. Sodium hypochlorite solution ([[chlorine bleach]]) mixed with common household liquids such as [[acetone]], [[methyl ethyl ketone]], [[ethanol]], or [[isopropyl alcohol]] can produce some chloroform, in addition to other compounds, such as [[chloroacetone]] or [[dichloroacetone]].{{citation needed|date=November 2020}}