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Dichloromethane
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<h2 id="occurrence">Occurrence</h2> <p>Natural sources of dichloromethane include oceanic sources, <a href="/facts/Macroalgae/thLwLBk8">macroalgae</a>, wetlands, and volcanoes.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> However, the majority of dichloromethane in the environment is the result of industrial emissions.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> </p> <h2 id="production">Production</h2> <p>DCM is produced by <a href="/facts/Chemical_reaction/GpqWlKrz">treating</a> either <a href="/facts/Chloromethane/DvmeEgDS">chloromethane</a> or <a href="/facts/Methane/kBHneYnh">methane</a> with chlorine gas at 400–500 °C. At these temperatures, both methane and chloromethane undergo a series of reactions producing progressively more chlorinated products. In this way, an estimated 400,000 tons were produced in the US, Europe, and Japan in 1993.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <a href="/facts/Methane/kBHneYnh">CH4</a> + <a href="/facts/Chlorine/y27UwYBM">Cl2</a> → <a href="/facts/Chloromethane/DvmeEgDS">CH3Cl</a> + <a href="/facts/Hydrogen_chloride/7Wzkhomd">HCl</a> CH3Cl + Cl2 → CH2Cl2 + HCl CH2Cl2 + Cl2 → <a href="/facts/Chloroform/gvzuJMXa">CHCl3</a> + HCl CHCl3 + Cl2 → <a href="/facts/Carbon_tetrachloride/S2ekjT0E">CCl4</a> + HCl <p>The output of these processes is a mixture of chloromethane, dichloromethane, <a href="/facts/Chloroform/gvzuJMXa">chloroform</a>, and <a href="/facts/Carbon_tetrachloride/S2ekjT0E">carbon tetrachloride</a> as well as hydrogen chloride as a byproduct. These compounds are separated by <a href="/facts/Distillation/plDvUMxn">distillation</a>. </p><p>DCM was first prepared in 1839 by the French chemist <a href="/facts/Henri_Victor_Regnault/24Mz0XDX">Henri Victor Regnault</a> (1810–1878), who isolated it from a mixture of <a href="/facts/Chloromethane/DvmeEgDS">chloromethane</a> and <a href="/facts/Chlorine/y27UwYBM">chlorine</a> that had been exposed to <a href="/facts/Sunlight/WPkJRC7s">sunlight</a>.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="uses">Uses</h2> <p>DCM's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> In the <a href="/facts/Food_industry/1JPhss6V">food industry</a>, it is used to <a href="/facts/Decaffeination/NvBxbYaS">decaffeinate</a> <a href="/facts/Coffee/Q4Ko2C7I">coffee</a> and <a href="/facts/Tea/oDQhcyrc">tea</a> as well as to prepare extracts of <a href="/facts/Hops/mBRf6xGx">hops</a> and other <a href="/facts/Flavoring/sGR38zXy">flavourings</a>.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a><a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a> Its volatility has led to its use as an <a href="/facts/Aerosol_spray/8SfNdfYs">aerosol spray propellant</a> and as a <a href="/facts/Blowing_agent/T6JxAzVX">blowing agent</a> for <a href="/facts/Polyurethane_foam/BxeD6S09">polyurethane foams</a>. </p> <h3>Specialized uses</h3> <p>The chemical compound's low <a href="/facts/Boiling_point/E2BK9QoS">boiling point</a> allows the chemical to function in a <a href="/facts/Heat_engine/t1gq4r5d">heat engine</a> that can extract mechanical energy from small temperature differences. An example of a DCM heat engine is the <a href="/facts/Drinking_bird/enCpUKGg">drinking bird</a>. The toy works at room temperature.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a> It is also used as the fluid in <a href="/facts/Jukebox/Wd7KHzrk">jukebox</a> displays and holiday <a href="/facts/Bubble_light/5Ub4DMwn">bubble lights</a> that have a colored bubbling tube above a lamp as a source of heat and a small amount of rock salt to provide thermal mass and a nucleation site for the phase changing solvent. </p><p>DCM chemically welds certain plastics. For example, it is used to seal the casing of electric meters. Often sold as a main component of <a href="/facts/Plastic_welding_adhesive/2ndqGfhN">plastic welding adhesives</a>, it is also used extensively by <a href="/facts/Model_building/JU7rhSf4">model building</a> hobbyists for joining plastic components together. It is commonly referred to as "Di-clo". </p><p>It is used in the garment printing industry for removal of heat-sealed garment transfers. </p><p>DCM is used in the material testing field of <a href="/facts/Civil_engineering/avh5kEq2">civil engineering</a>; specifically it is used during the testing of bituminous materials as a solvent to separate the binder from the aggregate of an <a href="/facts/Bitumen/tW6EqphW">asphalt</a> or <a href="/facts/Macadam/vJjhVgzw">macadam</a> to allow the testing of the materials.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a> </p><p>Dichloromethane extract of <i><a href="/facts/Asparagopsis_taxiformis/EUKpGeHX">Asparagopsis taxiformis</a></i>, a seaweed <a href="/facts/Fodder/b4Hw0Lq0">fodder</a> for cattle, has been found to reduce their <a href="/facts/Methane_emissions/IrclnYfB">methane emissions</a> by 79%.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a> </p><p>It has been used as the principal component of various paint and lacquer strippers, although its use is now restricted in the EU and many such products now use <a href="/facts/Benzyl_alcohol/rsY1Jqr4">benzyl alcohol</a> as a safer alternative. </p> <h2 id="chemical-reactions">Chemical reactions</h2> <p>Dichloromethane is widely used as a solvent in part because it is relatively inert. It does participate in reactions with certain strong nucleophiles however. <a href="/facts/Tert-butyllithium/qokAzb3U">Tert-butyllithium</a> deprotonates DCM:<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> </p> H2CCl2 + RLi → HCCl2Li + RH <p><a href="/facts/Methyllithium/Fo5UzmsP">Methyllithium</a> reacts with methylene chloride to give <a href="/facts/Chlorocarbene/fPh0ee4n">chlorocarbene</a>: </p> CH2Cl2 + CH3Li → CHCl + CH4 + LiCl <p>Although DCM is a common solvent in organic chemistry laboratories and is commonly assumed to be inert, it does react with some amines and triazoles.<a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> Tertiary amines can react with DCM to form quaternary chloromethyl chloride salts via the <a href="/facts/Menshutkin_reaction/G5HYqsbs">Menshutkin reaction</a>.<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> Secondary amines can react with DCM to yield an equilibrium of iminium chlorides and chloromethyl chlorides, which can react with a second equivalent of the secondary amine to form <a href="/facts/Aminal/eAWdDkIn">aminals</a>.<a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> At increased temperatures, <a href="/facts/Pyridine/X817hCch">pyridines</a> including <a href="/facts/4-Dimethylaminopyridine/cP9W5tqt">DMAP</a>, react with DCM to form methylene bispyridinium dichlorides.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> <a href="/facts/Hydroxybenzotriazole/heGstL97">Hydroxybenzotriazole</a> and related reagents used in peptide coupling react with DCM in the presence of <a href="/facts/Triethylamine/6DjzaGGv">triethylamine</a>, forming <a href="/facts/Acetal/DuwXfBMz">acetals</a>.<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> </p> <h2 id="toxicity">Toxicity</h2> <p>Serious health risks are associated with DCM, despite being one of the least <a href="/facts/Toxic/qa96rs60">toxic</a> simple chlorohydrocarbons. Its high <a href="/facts/Volatility_(chemistry)/90r3ep6w">volatility</a> makes it an inhalation hazard.<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a><a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> It can also be absorbed through the skin.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a><a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a> Symptoms of acute overexposure to dichloromethane via inhalation include difficulty concentrating, <a href="/facts/Dizziness/eI8UvmS5">dizziness</a>, <a href="/facts/Fatigue_(medical)/C2oo4Hvg">fatigue</a>, <a href="/facts/Nausea/dyhkcbeD">nausea</a>, <a href="/facts/Headache/mdmmC9DP">headaches</a>, numbness, weakness, and irritation of the <a href="/facts/Upper_respiratory_tract/nnG9UEmr">upper respiratory tract</a> and <a href="/facts/Eye/h3lbYU55">eyes</a>. More severe consequences can include <a href="/facts/Suffocation/bahl3DJf">suffocation</a>, <a href="/facts/Loss_of_consciousness/SS240v32">loss of consciousness</a>, <a href="/facts/Coma/N9oQ7g7R">coma</a>, and death.<a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a><a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a> </p><p>DCM is also metabolized to <a href="/facts/Carbon_monoxide/CKuLtEMJ">carbon monoxide</a> potentially leading to <a href="/facts/Carbon_monoxide_poisoning/UyjKzy4W">carbon monoxide poisoning</a>.<a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> Acute exposure by inhalation has resulted in <a href="/facts/Optic_neuropathy/AqJo91bQ">optic neuropathy</a><a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> and <a href="/facts/Hepatitis/FIN87T5e">hepatitis</a>.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> Prolonged skin contact can result in DCM dissolving some of the <a href="/facts/Adipose_tissue/PxxedB6e">fatty tissues</a> in skin, resulting in skin irritation or <a href="/facts/Chemical_burns/GycBJMJo">chemical burns</a>.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> </p><p>It may be <a href="/facts/Carcinogen/soH8Y9CE">carcinogenic</a>, as it has been linked to <a href="/facts/Cancer/PVW6n1D0">cancer</a> of the <a href="/facts/Lung_cancer/LHLdR454">lungs</a>, <a href="/facts/Liver_cancer/a7N4vD4L">liver</a>, and <a href="/facts/Pancreatic_cancer/6h9GIInW">pancreas</a> in laboratory animals.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> Other animal studies showed <a href="/facts/Breast_cancer/6hME580v">breast cancer</a> and <a href="/facts/Salivary_gland_cancer/VgKBrsHW">salivary gland cancer</a>. Research is not yet clear as to what levels may be carcinogenic to humans.<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a><a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> DCM crosses the <a href="/facts/Placenta/7XUoks1b">placenta</a> but <a href="/facts/Fetal/evocHd0Y">fetal</a> toxicity in women who are exposed to it during <a href="/facts/Pregnancy/vEKYGpep">pregnancy</a> has not been proven.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a> In animal experiments, it was fetotoxic at doses that were maternally toxic but no <a href="/facts/Teratology/j4BN6lsB">teratogenic</a> effects were seen.<a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> </p><p>In people with pre-existing heart problems, exposure to DCM can cause <a href="/facts/Heart_arrhythmia/ooEpr46Q">abnormal heart rhythms</a> and/or <a href="/facts/Heart_attack/xoGw0qcG">heart attacks</a>, sometimes without any other symptoms of overexposure.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> People with existing <a href="/facts/Liver/Rtp4Fk2b">liver</a>, <a href="/facts/Nervous_system/CDxRKU2U">nervous system</a>, or <a href="/facts/Skin/4havlLzG">skin</a> problems may worsen after exposure to methylene chloride.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> </p> <h3>Regulation</h3> <p>In many countries, products containing DCM must carry labels warning of its health risks. Concerns about its health effects have led to a search for alternatives in many of its applications.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a><a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> </p><p>In the <a href="/facts/European_Union/6GYcR8qM">European Union</a>, the <a href="/facts/Scientific_Committee_on_Occupational_Exposure_Limit_Values/8lsYqeoe">Scientific Committee on Occupational Exposure Limit Values</a> (SCOEL) recommends an <a href="/facts/Occupational_exposure_limit/chpTx5og">occupational exposure limit</a> for DCM of 100 ppm (8-hour time-weighted average) and a <a href="/facts/Short-term_exposure_limit/RHSQtE4z">short-term exposure limit</a> of 200 ppm for a 15-minute period.<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> The <a href="/facts/European_Parliament/H9WLUd1r">European Parliament</a> voted in 2009 to ban the use of DCM in paint-strippers for consumers and many professionals,<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> with the ban taking effect in December 2010.<a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a> </p><p>In February 2013, the US <a href="/facts/Occupational_Safety_and_Health_Administration/dCGbW5Ax">Occupational Safety and Health Administration</a> (OSHA) and the <a href="/facts/National_Institute_for_Occupational_Safety_and_Health/5WjdDNMN">National Institute for Occupational Safety and Health</a> warned that at least 14 bathtub refinishers have died since 2000 from DCM exposure. These workers had been working alone, in poorly ventilated bathrooms, with inadequate or no respiratory protection, and no training about the hazards of DCM.<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a><a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a><a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a> OSHA has since then issued a DCM standard.<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a> </p><p>On March 15, 2019, the US <a href="/facts/United_States_Environmental_Protection_Agency/ghI985SI">Environmental Protection Agency</a> (EPA) issued a final rule to prohibit the manufacture (including importing and exporting), processing, and distribution of DCM in all paint removers for consumer use, effective in 180 days. However, it does not affect other products containing DCM, including many consumer products not intended for paint removal. On April 20, 2023, the EPA proposed a widespread ban on the production of DCM with some exceptions for military and industrial uses.<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a> On April 30, 2024, the EPA finalized a ban on most commercial uses of DCM, which mainly banned its application for stripping paint and degreasing surfaces but allowed for some remaining commercial applications, such as chemical production.<a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a> </p> <h2 id="environmental-effects">Environmental effects</h2> <p>Dichloromethane is not classified as an ozone-depleting substance by the <a href="/facts/Montreal_Protocol/Hmf70BQK">Montreal Protocol</a>.<a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a> The US <a href="/facts/Clean_Air_Act_(United_States)/zfdgfHjP">Clean Air Act</a> does not regulate dichloromethane as an <a href="/facts/Ozone_depletion/ssGWpcx3">ozone depleter</a>.<a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a> Dichloromethane has been classified as a very short-lived substance (VSLS). Despite their short atmospheric lifetimes of less than 0.5 year, VSLSs can contribute to stratospheric ozone depletion, particularly if emitted in regions where rapid transport to the stratosphere occurs.<a class="footnote-ref" id="fnref:48" href="#fn:48"><sup>48</sup></a> Atmospheric abundances of dichloromethane have been increasing in recent years. </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/Deuterated_dichloromethane/f5L7UVnn">Deuterated dichloromethane</a></li> <li><a href="/facts/Chloromethane/DvmeEgDS">Chloromethane</a></li> <li><a href="/facts/Trichloromethane/gvzuJMXa">Trichloromethane</a></li> <li><a href="/facts/Tetrachloromethane/S2ekjT0E">Tetrachloromethane</a></li> <li><a href="/facts/List_of_organic_compounds/68klBjhN">List of organic compounds</a></li> <li><a href="/facts/Carbon_monoxide-releasing_molecules/L6h7AKXx">Carbon monoxide-releasing molecules</a></li></ul> <h2 id="external-links">External links</h2> Wikimedia Commons has media related to Dichloromethane. <ul><li><a href="https://www.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0058&p_version=2">International Chemical Safety Card 0058</a></li> <li>NIOSH Pocket Guide to Chemical Hazards. <a href="https://www.cdc.gov/niosh/npg/npgd0414.html">"#0414"</a>. <a href="/facts/National_Institute_for_Occupational_Safety_and_Health/5WjdDNMN">National Institute for Occupational Safety and Health</a> (NIOSH).</li> <li><a href="http://www.npi.gov.au/substances/dichloromethane/index.html">National Pollutant Inventory – Dichloromethane Fact Sheet</a></li> <li><a href="https://web.archive.org/web/20121014171614/http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr306.pdf">Dichloromethane at National Toxicology Program</a></li> <li><a href="http://www.inchem.org/documents/iarc/vol71/004-dichloromethane.html">IARC Summaries & Evaluations Vol. 71 (1999)</a></li> <li><a href="http://www.hc-sc.gc.ca/ewh-semt/alt_formats/hecs-sesc/pdf/pubs/contaminants/psl1-lsp1/dichloromethane/dichloromethane-eng.pdf">Canadian Environmental Protection Act Priority Substances List Assessment Report</a></li> <li><a href="http://www.colby.edu/chemistry/cmp/cmp.html">Organic Compounds Database</a></li> <li><a href="http://www.chlorinated-solvents.eu">Sustainable uses and Industry recommendations</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Rossberg, M. et al. (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Gribble, Gordon W. (2009). Naturally Occurring Organohalogen Compounds. Springer. ISBN 978-3211993248. <a href="978-3211993248" target="_blank">978-3211993248</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Gribble, Gordon W. (2009). Naturally Occurring Organohalogen Compounds. Springer. ISBN 978-3211993248. <a href="978-3211993248" target="_blank">978-3211993248</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Rossberg, M. et al. (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Regnault, V. (1839) "De l'action du chlore sur les éthers hydrochloriques de l'alcool et de l'esprit de bois, et de plusieurs points de la théorie des éthers" (On the action of chlorine on the hydrochloric ethers of ethanol and methanol, and on several points of the theory of ethers), Annales de chimie et physique, series 2, 71 : 353–431; see especially: "Seconde partie. De l'action du chlore sur l'éther hydrochlorique de l'esprit de bois" (Second part. On the action of chlorine on the hydrochloric ether of methanol [i.e., chloromethane]), pages 377–380. Regnault gives dichloromethane the name éther hydrochlorique monochloruré (monochlorinated hydrochloric ether). Note: Regnault gives the empirical formula for dichloromethane as C2H4Cl4 because during that era, chemists used incorrect atomic masses. Reprinted in German in: Regnault, V. (1840). "Ueber die Einwirkung des Chlors auf die Chlorwasserstoffäther des Alkohols und Holzgeistes und über mehrere Punkte der Aethertheorie". Annalen der Chemie und Pharmacie. 33 (3): 310–334. doi:10.1002/jlac.18400330306. See p. 328. Regnault, V. (1840). "Ueber die Wirkung des Chlors auf den Chlorwasserstoffäther des Alkohols und des Holzgeistes, so wie über mehrere Puncte der Aethertheorie". Journal für Praktische Chemie. 19: 193–218. doi:10.1002/prac.18400190134. See p. 210. <a href="https://archive.today/20131023140514/http://babel.hathitrust.org/cgi/pt?id=nyp.33433062741982;view=1up;seq=385" target="_blank">https://archive.today/20131023140514/http://babel.hathitrust.org/cgi/pt?id=nyp.33433062741982;view=1up;seq=385</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Rossberg, M. et al. (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Office of Environmental Health Hazard Assessment (September 2000). "Dichloromethane" (PDF). Public Health Goals for Chemicals in Drinking Water. California Environmental Protection Agency. 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