Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 09:17, 21 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit		Latest revision as of 02:01, 17 December 2024 edit undoArthurfragoso (talk | contribs)Extended confirmed users2,076 edits Fixes image on dark mode
(418 intermediate revisions by more than 100 users not shown)
Line 1:		Line 1:
			{{redirect|Di-clo|the anti-inflammatory drug trade named Diclo|Diclofenac}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 396340185
			| verifiedrevid = 409133414
	| ImageFileL1 = Dichloromethane.svg
			| ImageFileL1 = Dichloromethane molecular structure.svg
	| ImageSizeL1 = 100px
	| ImageFileR1 = Dichloromethane-3D-vdW.png		| ImageFileR1 = Dichloromethane-3D-vdW.png
			| ImageClassL1 = skin-invert
	| ImageSizeR1 = 120px
			| ImageFile2 = Sample of dichloromethane.jpg
	| IUPACName = Dichloromethane
			| ImageSize2 = 200px
	| OtherNames = Methylene chloride, methylene dichloride, Solmethine, Narkotil, Solaesthin, Di-clo, Freon 30, R-30, DCM, UN 1593, MDC
			| PIN = Dichloromethane
			| OtherNames = Methylene bichloride; Methylene chloride gas; Methylene dichloride; Solmethine; Narkotil; Solaesthin; Di-clo; Refrigerant-30; Freon-30; R-30; DCM; MDC
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 13:		Line 16:
	| UNII = 588X2YUY0A		| UNII = 588X2YUY0A
	| InChIKey = YMWUJEATGCHHMB-UHFFFAOYAG		| InChIKey = YMWUJEATGCHHMB-UHFFFAOYAG
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 45967		| ChEMBL = 45967
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 25:		Line 29:
	| InChI = 1/CH2Cl2/c2-1-3/h1H2		| InChI = 1/CH2Cl2/c2-1-3/h1H2
	| RTECS = PA8050000		| RTECS = PA8050000
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 15767		| ChEBI = 15767
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D02330		| KEGG = D02330
			| UNNumber = 1593
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=1 | H=2 | Cl=2
	| Formula = CH<sub>2</sub>Cl<sub>2</sub>
	| MolarMass = 84.93 g/mol
	| Appearance = Colorless liquid		| Appearance = Colorless liquid
			| Odor = Faint, ]-like<ref name=PGCH/>
	| Density = 1.33 g/cm<sup>3</sup>, liquid
			| Density = 1.3266 g/cm<sup>3</sup> (20 °C)<ref name=b92>{{RubberBible92nd|page=3.164}}</ref>
	| MeltingPtC = -96.7
			| MeltingPtC = −96.7
	| BoilingPtC = 39.6		| BoilingPtC = 39.6
			| BoilingPt_notes = <br> decomposes at 720&nbsp;°C<ref name=chemister /><br> {{convert|39.75|C|F K}}<br> at 760 mmHg<ref name=pubchem />
	| Solubility = 13 g/L at 20 °C
			| Solubility = 25.6 g/L (15 °C)<br> 17.5 g/L (25 °C)<br> 15.8 g/L (30 °C)<br> 5.2 g/L (60 °C)<ref name=chemister>. chemister.ru</ref>
	| VaporPressure = 47 kPa at 20 °C
			| VaporPressure = 0.13 kPa (−70.5 °C)<br> 2 kPa (−40 °C)<br> 19.3 kPa (0 °C)<br> 57.3 kPa (25 °C)<ref name=nist>{{nist|name=Methylene chloride|id=C75092|accessdate=2014-05-26|mask=FFFF|units=SI}}</ref><br> 79.99 kPa (35 °C)<ref name=chemister />
			| RefractIndex = 1.4244 (20 °C)<ref name=pubchem>{{PubChemLink|6344}}</ref><ref name="sigma" />
			| Viscosity = 0.43 cP (20 °C)<ref name=pubchem /><br> 0.413 cP (25 °C)
			| SolubleOther = Miscible in ], ], ], ], ], ], ]
			| HenryConstant = 3.25 L·atm/mol<ref name=pubchem />
			| MagSus = −46.6·10<sup>−6</sup> cm<sup>3</sup>/mol
			| LogP = 1.19<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/75-09-2_401673.html|title=Dichloromethane_msds}}</ref>
	}}		}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Structure
			| Dipole = 1.6 D
	| MainHazards = Harmful ('''Xn'''), ]
			}}
			| Section4 = {{Chembox Thermochemistry
			| HeatCapacity = 102.3 J/(mol·K)<ref name=nist />
			| Entropy = 174.5 J/(mol·K)<ref name=nist />
			| DeltaHf = −124.3 kJ/mol<ref name=nist />
			| DeltaHc = -454.0 kJ/mol (from standard enthalpies of formation)<ref name=nist />
			}}
			| Section5 =
			| Section6 =
			| Section7 = {{Chembox Hazards
			| MainHazards =
			| GHSPictograms = {{GHS07}} {{GHS08}}
			| GHS_ref = <ref name="sigma">{{Sigma-Aldrich|id=644501|name=Dichloromethane|accessdate=2014-05-26}}</ref>
			| GHSSignalWord = Warning
			| HPhrases = {{H-phrases|315|319|335|336|351|373}}
			| PPhrases = {{P-phrases|261|281|305+351+338}}
	| NFPA-H = 2		| NFPA-H = 2
	| NFPA-F = 1		| NFPA-F = 1
	| NFPA-R = 0		| NFPA-R = 0
	| NFPA-O =		| NFPA-S =
			| FlashPt = None, but can form flammable vapor-air mixtures above ≈100 °C<ref>{{cite web |url=http://www.hse.gov.uk/research/rrpdf/rr982.pdf |title=Real time measurement of dichloromethane containing mixtures |publisher=Health & Safety Laboratory |access-date=5 August 2015}}</ref>
	| RPhrases = {{R40}}
			| AutoignitionPtC = 556
	| SPhrases = {{S23}} {{S24/25}} {{S36/37}}
			| PEL = 25 ppm over 8 hours (time-weighted average), 125 ppm over 15 minutes (])<ref name=PGCH/><ref name=Hazard/>
	| FlashPt = None
			| IDLH = Ca <ref name=PGCH/>
	| Autoignition = 556 °C
			| REL = Ca<ref name=PGCH/>
			| LD50 = 1.25 g/kg (rats, oral)<br> 2 g/kg (rabbits, oral)<ref name=chemister />
			| ExploLimits = 13%-23%<ref name=PGCH/>
			| EyeHazard = Irritant
			| LC50 = 24,929 ppm (rat, 30&nbsp;])<br/>14,400 ppm (mouse, 7&nbsp;])<ref name=IDLH>{{IDLH|75092|methylene chloride}}</ref>
			| LCLo = 5000 ppm (guinea pig, 2&nbsp;h)<br/>10,000 ppm (rabbit, 7&nbsp;h)<br/>12,295 ppm (cat, 4.5&nbsp;h)<br/>14,108 ppm (dog, 7&nbsp;h)<ref name=IDLH/>
	}}		}}
			|Section8={{Chembox Legal status
			| legal_AU =
			| legal_BR = B1
			| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
			| legal_US =
			| legal_UK =
			| legal_UN =
			}}
	}}		}}
			'''Dichloromethane''' ('''DCM''', '''methylene chloride''', or '''methylene bichloride''') is an ] with the ] {{chem2|]]2]2}}. This colorless, ] liquid with a ]-like, sweet odor is widely used as a ]. Although it is not ] with water, it is slightly ], and miscible with many organic ]s.<ref name=Ullmann>Rossberg, M. ''et al.'' (2006) "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a06_233.pub2}}.</ref>
	] of dichloromethane showing complicated overlapping ] of mid IR absorption features.]]
			==Occurrence==
	'''Dichloromethane''' (DCM or methylene chloride) is an ] with the ] ]]<sub>2</sub>]<sub>2</sub>. This colorless, volatile liquid with a moderately sweet aroma is widely used as a ]. More than 500,000 tons were produced in 1991. Although it is not ] with water, it is miscible with many organic ]s.<ref name=Ullmann>M. Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a06_233.pub2}}</ref> It was first prepared in 1840 by the ] ] ], who isolated it from a mixture of ] and ] that had been exposed to ].
			Natural sources of dichloromethane include oceanic sources, ], wetlands, and volcanoes.<ref name=Gribble>{{cite book | author = Gribble, Gordon W. | title = Naturally Occurring Organohalogen Compounds |date=2009 | publisher = Springer|isbn=978-3211993248}}</ref> However, the majority of dichloromethane in the environment is the result of industrial emissions.<ref name=Gribble/>
	==Production==		==Production==
	Dichloromethane is produced by ] either methyl chloride or methane with chlorine gas at 400&ndash;500&nbsp;°C. At these temperatures, both methane and methyl chloride undergo a series of reactions producing progressively more chlorinated products.<ref name=Ullmann/>		DCM is produced by ] either ] or ] with chlorine gas at 400–500&nbsp;°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.<ref name=Ullmann/>
	:] + ] → ] + ]		:{{chem2|] + ] → ] + ]}}
			:{{chem2|CH3Cl + Cl2 → CH2Cl2 + HCl}}
	:CH<sub>3</sub>Cl + Cl<sub>2</sub> → CH<sub>2</sub>Cl<sub>2</sub> + HCl
	:CH<sub>2</sub>Cl<sub>2</sub> + Cl<sub>2</sub> → ] + HCl		:{{chem2|CH2Cl2 + Cl2 → ] + HCl}}
	:CHCl<sub>3</sub> + Cl<sub>2</sub> → ] + HCl		:{{chem2|CHCl3 + Cl2 → ] + HCl}}
	The output of these processes is a mixture of ], dichloromethane, ], and ]. These compounds are separated by ].		The output of these processes is a mixture of chloromethane, dichloromethane, ], and ] as well as hydrogen chloride as a byproduct. These compounds are separated by ].
			DCM was first prepared in 1839 by the French chemist ] (1810–1878), who isolated it from a mixture of ] and ] that had been exposed to ].<ref>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: (Second part. On the action of chlorine on the hydrochloric ether of methanol ), pages 377–380. Regnault gives dichloromethane the name ''éther hydrochlorique monochloruré'' (monochlorinated hydrochloric ether). Note: Regnault gives the empirical formula for dichloromethane as C<sub>2</sub>H<sub>4</sub>Cl<sub>4</sub> because during that era, chemists used incorrect atomic masses.<br>
			Reprinted in German in:
			* {{cite journal | last1 = Regnault | first1 = V. | title = Ueber die Einwirkung des Chlors auf die Chlorwasserstoffäther des Alkohols und Holzgeistes und über mehrere Punkte der Aethertheorie | journal = Annalen der Chemie und Pharmacie | volume = 33 | issue = 3 | pages = 310–334 | year = 1840 | doi = 10.1002/jlac.18400330306 | url = https://books.google.com/books?id=4Uw9AAAAcAAJ&pg=PA310 }} See p. 328.
			*{{cite journal | last1 = Regnault | first1 = V. | title = Ueber die Wirkung des Chlors auf den Chlorwasserstoffäther des Alkohols und des Holzgeistes, so wie über mehrere Puncte der Aethertheorie | journal = Journal für Praktische Chemie | volume = 19 | pages = 193–218 | year = 1840 | doi = 10.1002/prac.18400190134 | url = https://zenodo.org/record/1427780 }} See p. 210.</ref>
	==Uses==		==Uses==
			DCM's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes.<ref name=Ullmann/> In the ], it is used to ] ] and ] as well as to prepare extracts of ] and other ]s.<ref>{{cite web|url=http://oehha.ca.gov/media/downloads/pesticides/report/dcm.pdf |title=Dichloromethane |date=September 2000 |publisher=] |access-date=June 5, 2016 |author=Office of Environmental Health Hazard Assessment |work=Public Health Goals for Chemicals in Drinking Water }}{{dead link|date=December 2016 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref>{{cite web |last1=James2014-04-09T00:00:00+01:00 |first1=Emily |title=Dichloromethane |url=https://www.chemistryworld.com/podcasts/dichloromethane/7254.article |website=Chemistry World |language=en}}</ref> Its volatility has led to its use as an ] and as a ] for ]s.
	Dichloromethane's volatility and ability to dissolve a wide range of organic compounds makes it a useful solvent for many chemical processes. Concerns about its health effects have led to a search for alternatives in many of these applications.<ref name=Ullmann/>
			===Specialized uses===
	It is widely used as a ] and a ]. In the ], it has been used to ] ] and ] as well as to prepare extracts of ] and other ]s.<ref>{{cite web|author = Office of Environmental Health Hazard Assessment|publisher = ]|month = September|year = 2000|work = Public Health Goals for Chemicals in Drinking Water|title = Dichloromethane|url = http://www.oehha.ca.gov/water/phg/pdf/dcm.pdf}}</ref> Its volatility has led to its use as an ] and as a ] for ] ]s.
			] of dichloromethane showing complicated overlapping ] of mid IR absorption features]]
			The chemical compound's low ] allows the chemical to function in a ] that can extract mechanical energy from small temperature differences. An example of a DCM heat engine is the ]. The toy works at room temperature.<ref name="perelman">{{cite book |last=Perelman |first=Yakov |url=https://archive.org/details/PhysicsForEntertainmentBook2 |title=Physics for Entertainment |date=1972 |publisher=Hyperion Books |isbn=978-1401309213 |volume=2 |pages=175–178 |orig-year=1936}} </ref> It is also used as the fluid in ] displays and holiday ]s 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.
			DCM chemically welds certain plastics. For example, it is used to seal the casing of electric meters. Often sold as a main component of ]s, it is also used extensively by ] hobbyists for joining plastic components together. It is commonly referred to as "Di-clo".
	====Specialized uses====
	Dichloromethane chemically welds certain plastics; for example, it is used to seal the casing of electric meters. Often sold as a main component of ]s, it is also used extensively by ] hobbyists for joining plastic components together — it is commonly referred to as "Di-clo."
	It is also used in the garment printing industry for removal of heat-sealed garment transfers, and its volatility is exploited in novelty items — ]s, ]s, and ] displays.		It is used in the garment printing industry for removal of heat-sealed garment transfers.
	Dichloromethane is used within the material testing field of ]; specifically it is used during the testing of bituminous materials as a solvent to separate the binder from the aggregate of an ] or ] to allow the testing of the materials.<ref>{{cite book|author = ]|title = The Shell Bitumen Handbook|url = http://books.google.com/?id=bA1tIkRJL8kC&pg=PA277&lpg=PA277&dq=aliquot+bitumen+solvent+methylene+chloride|isbn = 9780727732200|date = 2003-09-25}}</ref>		DCM is used in the material testing field of ]; specifically it is used during the testing of bituminous materials as a solvent to separate the binder from the aggregate of an ] or ] to allow the testing of the materials.<ref>{{cite book|author = Shell Bitumen|title = The Shell Bitumen Handbook|url = https://books.google.com/books?id=bA1tIkRJL8kC&pg=PA277|isbn = 978-0-7277-3220-0|date = 2003-09-25| publisher=Thomas Telford |author-link = Royal Dutch Shell}}</ref>
			Dichloromethane extract of '']'', a seaweed ] for cattle, has been found to reduce their ] by 79%.<ref>{{cite journal|title=Identification of bioactives from the red seaweed ''Asparagopsis taxiformis'' that promote antimethanogenic activity in vitro|first1=Lorenna |last1=Machado|first2=Marie |last2=Magnusson|first3=Nicholas |last3=Paul|first4=Nigel |last4=Tomkins|year=2016|journal=Journal of Applied Phycology|volume=28|issue=5|pages=3117–3126|doi=10.1007/s10811-016-0830-7|doi-access=free|bibcode=2016JAPco..28.3117M }}</ref>
			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 ] as a safer alternative.
			==Chemical reactions==
			Dichloromethane is widely used as a solvent in part because it is relatively inert. It does participate in reactions with certain strong nucleophiles however. ] deprotonates DCM:<ref>{{cite journal |doi=10.1021/om50005a008|title=Homologation of boronic esters to .alpha.-chloro boronic esters |year=1983 |last1=Matteson |first1=Donald S. |last2=Majumdar |first2=Debesh |journal=Organometallics |volume=2 |issue=11 |pages=1529–1535 }}</ref>
			:{{Chem2|H2CCl2 + RLi -> HCCl2Li + RH}}
			] reacts with methylene chloride to give ]:{{cn|date=May 2024}}
			:{{chem2|CH2Cl2 + CH3Li -> CHCl + CH4 + LiCl}}
			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.<ref>{{Cite journal |last1=Mills |first1=John E. |last2=Maryanoff |first2=Cynthia A. |last3=Cosgrove |first3=Robin M. |last4=Scott |first4=Lorraine |last5=McComsey |first5=David F. |title=The Reaction of Amines with Methylene Chloride. A Brief Review |date=1984 |url=http://www.tandfonline.com/doi/abs/10.1080/00304948409356172 |journal=Organic Preparations and Procedures International |language=en |volume=16 |issue=2 |pages=97–114 |doi=10.1080/00304948409356172 |issn=0030-4948}}</ref> Tertiary amines can react with DCM to form quaternary chloromethyl chloride salts via the ].<ref>{{Cite journal |last1=Dunlap |first1=Lee E. |last2=Olson |first2=David E. |date=2018-05-31 |title=Reaction of N , N -Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions |journal=ACS Omega |language=en |volume=3 |issue=5 |pages=4968–4973 |doi=10.1021/acsomega.8b00507 |issn=2470-1343 |pmc=5981293 |pmid=29876537}}</ref> 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 ]s.<ref>{{Cite journal |last1=Mills |first1=John E. |last2=Maryanoff |first2=Cynthia A. |last3=McComsey |first3=David F. |last4=Stanzione |first4=Robin C. |last5=Scott |first5=Lorraine |date=1987 |title=Reaction of amines with methylene chloride. Evidence for rapid aminal formation from N-methylenepyrrolidinium chloride and pyrrolidine |url=https://pubs.acs.org/doi/abs/10.1021/jo00385a038 |journal=The Journal of Organic Chemistry |language=en |volume=52 |issue=9 |pages=1857–1859 |doi=10.1021/jo00385a038 |issn=0022-3263}}</ref> At increased temperatures, ]s including ], react with DCM to form methylene bispyridinium dichlorides.<ref>{{Cite journal |last1=Rudine |first1=Alexander B. |last2=Walter |first2=Michael G. |last3=Wamser |first3=Carl C. |date=2010-06-18 |title=Reaction of Dichloromethane with Pyridine Derivatives under Ambient Conditions |url=https://pubs.acs.org/doi/10.1021/jo100276m |journal=The Journal of Organic Chemistry |language=en |volume=75 |issue=12 |pages=4292–4295 |doi=10.1021/jo100276m |pmid=20469919 |issn=0022-3263}}</ref> ] and related reagents used in peptide coupling react with DCM in the presence of ], forming ]s.<ref>{{Cite journal |last1=Ji |first1=Jian-guo |last2=Zhang |first2=De-yi |last3=Ye |first3=Yun-hua |last4=Xing |first4=Qi-yi |date=1998 |title=Studies on the reactions of HOBt, HOOBt, HOSu with dichloroalkane solvents |url=https://linkinghub.elsevier.com/retrieve/pii/S0040403998014063 |journal=Tetrahedron Letters |language=en |volume=39 |issue=36 |pages=6515–6516 |doi=10.1016/S0040-4039(98)01406-3}}</ref>
	==Toxicity==		==Toxicity==
	Dichloromethane is the least ] of the simple chlorohydrocarbons, but it is not without its health risks as its high ] makes it an acute inhalation hazard.<ref>{{cite journal|author = Rioux JP, Myers RA|title = Methylene chloride poisoning: a paradigmatic review|journal = J Emerg Med|volume = 6|issue = 3|pages = 227–238|year = 1988|pmid = 3049777|doi = 10.1016/0736-4679(88)90330-7}}</ref> Dichloromethane is also metabolized by the body to ] potentially leading to ].<ref>{{cite journal|author = Fagin J, Bradley J, Williams D|title = Carbon monoxide poisoning secondary to inhaling methylene chloride|journal = Br Med J|volume = 281|issue = 6253|pages = 1461|year = 1980|pmid = 7437838|doi = 10.1136/bmj.281.6253.1461|pmc = 1714874}}</ref> Acute exposure by inhalation has resulted in optic neuropathy<ref>{{cite journal|author = Kobayashi A, Ando A, Tagami N, Kitagawa M, Kawai E, Akioka M, Arai E, Nakatani T, Nakano S, Matsui Y, Matsumura M|title = Severe optic neuropathy caused by dichloromethane inhalation|journal = J Ocul Pharmacol and Ther|volume = 24|issue = 6|pages = 607–612|year = 2008|pmid = 19049266|doi = 10.1089/jop.2007.0100}}</ref> and hepatitis.<ref>{{cite journal|author = Cordes DH, Brown WD, Quinn KM|title = Chemically induced hepatitis after inhaling organic solvents|journal = West J Med|volume = 148|issue = 4|pages = 458–460|year = 1988|pmid = 3388849|pmc = 1026148}}</ref> Prolonged skin contact can result in the dichloromethane dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns.<ref>{{cite journal|author = Wells G, Waldron H|title = Methylene chloride burns|journal = Br J Ind Med|volume = 41|issue = 3|pages = 420|year = 1984|pmid = 6743591|pmc = 1009322}}</ref>		Serious health risks are associated with DCM, despite being one of the least ] simple ]. Its high ] makes it an inhalation hazard.<ref>{{cite journal |vauthors=Rioux JP, Myers RA | title = Methylene chloride poisoning: a paradigmatic review | journal = J Emerg Med | volume = 6 | issue = 3 | pages = 227–238 | year = 1988 | pmid = 3049777 | doi = 10.1016/0736-4679(88)90330-7 }}</ref><ref>{{cite journal|author = CDC |title = Fatal Exposure to Methylene Chloride Among Bathtub Refinishers — United States, 2000–2011 |journal = MMWR|volume = 61|issue = 7|pages = 119–122|year = 2012|pmid = 22357403 |url=https://www.cdc.gov/mmwr/preview/mmwrhtml/mm6107a2.htm}}</ref> It can also be absorbed through the skin.<ref name=PGCH/><ref name=NIOSHblog>{{cite web |url = http://blogs.cdc.gov/niosh-science-blog/2013/02/04/bathtub-refinishing/ |title = Dangers of Bathtub Refinishing |date = 4 February 2013 |first = Ronald M. |last = Hall |access-date = 21 January 2015 |publisher = National Institute for Occupational Safety and Health}}</ref>
			Symptoms of acute overexposure to dichloromethane via inhalation include difficulty concentrating, ], ], ], ]s, numbness, weakness, and irritation of the ] and ]s. More severe consequences can include ], ], ], and death.<ref name=PGCH>{{PGCH|0414}}</ref><ref name=NIOSHblog/>
			DCM is also metabolized to ] potentially leading to ].<ref>{{cite journal |vauthors=Fagin J, Bradley J, Williams D | title = Carbon monoxide poisoning secondary to inhaling methylene chloride | journal = Br Med J | volume = 281 | issue = 6253 | pages = 1461 | year = 1980 | pmid = 7437838 | pmc = 1714874 | doi = 10.1136/bmj.281.6253.1461 }}</ref> Acute exposure by inhalation has resulted in ]<ref>{{cite journal |vauthors=Kobayashi A, Ando A, Tagami N, Kitagawa M, Kawai E, Akioka M, Arai E, Nakatani T, Nakano S, Matsui Y, Matsumura M | title = Severe optic neuropathy caused by dichloromethane inhalation | journal = J Ocul Pharmacol and Ther | volume = 24 | issue = 6 | pages = 607–612 | year = 2008 | pmid = 19049266 | doi = 10.1089/jop.2007.0100 }}</ref> and ].<ref>{{cite journal |vauthors=Cordes DH, Brown WD, Quinn KM | title = Chemically induced hepatitis after inhaling organic solvents | journal = West J Med | volume = 148 | issue = 4 | pages = 458–460 | year = 1988 | pmid = 3388849 | pmc = 1026148 }}</ref> Prolonged skin contact can result in DCM dissolving some of the ] in skin, resulting in skin irritation or ].<ref>{{cite journal |vauthors=Wells GG, Waldron HA | title = Methylene chloride burns | journal = Br J Ind Med | volume = 41 | issue = 3 | pages = 420 | year = 1984 | pmid = 6743591 | pmc = 1009322 | doi = 10.1136/oem.41.3.420 }}</ref>
	It may be ]ic, as it has been linked to ] of the ], ], and ] in laboratory animals.<ref name="USDHHS">{{cite web|author=USDHHS|title=Toxicological Profile for Methylene Chloride|url=http://www.atsdr.cdc.gov/toxprofiles/tp14.pdf|accessdate=2006-09-10|format=PDF}}</ref> Dichloromethane crosses the placenta. ] toxicity in women who are exposed to it during ], however, has not been proven.<ref>{{cite journal|author = Bell B, Franks P, Hildreth N, Melius J|title = Methylene chloride exposure and birthweight in Monroe County, New York|journal = Environ Res|volume = 55|issue = 1|pages = 31–9|year = 1991|pmid = 1855488|doi = 10.1016/S0013-9351(05)80138-0}}</ref> In animal experiments, it was fetotoxic at doses that were maternally toxic but no ] effects were seen.<ref name="USDHHS"/>
			It may be ]ic, as it has been linked to ] of the ], ], and ] in laboratory animals.<ref name="USDHHS">{{cite web|author=USDHHS|title=Toxicological Profile for Methylene Chloride|url=http://www.atsdr.cdc.gov/toxprofiles/tp14.pdf|access-date=2006-09-10}}</ref> Other animal studies showed ] and ]. Research is not yet clear as to what levels may be carcinogenic to humans.<ref name=PGCH/><ref name=NIOSHblog/> DCM crosses the ] but ] toxicity in women who are exposed to it during ] has not been proven.<ref>{{cite journal |vauthors=Bell BP, Franks P, Hildreth N, Melius J | title = Methylene chloride exposure and birthweight in Monroe County, New York | journal = Environ Res | volume = 55 | issue = 1 | pages = 31–9 | year = 1991 | pmid = 1855488 | doi = 10.1016/S0013-9351(05)80138-0 | bibcode = 1991ER.....55...31B }}</ref> In animal experiments, it was fetotoxic at doses that were maternally toxic but no ] effects were seen.<ref name="USDHHS"/>
	In many countries, products containing dichloromethane must carry labels warning of its health risks.
			In people with pre-existing heart problems, exposure to DCM can cause ] and/or ]s, sometimes without any other symptoms of overexposure.<ref name=NIOSHblog/> People with existing ], ], or ] problems may worsen after exposure to methylene chloride.<ref name=Hazard/>
	In the European Union, the European Parliament voted in 2009 to ban the use of dichloromethane in paint-strippers for consumers and many professionals.<ref>{{cite web|url=http://www.europarl.europa.eu/news/expert/infopress_page/064-46096-012-01-03-911-20090113IPR46095-12-01-2009-2009-false/default_en.htm|title=Dichloromethane to be banned in paint-strippers|date=2009-01-14|accessdate=2009-01-15}}</ref> The ban took effect in December 2010.{{Citation needed|date=August 2010}}
			===Regulation===
			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.<ref name="Ullmann" /><ref>{{cite web |title=Summary of Regulations Controlling Air Emissions from Paint Stripping and Miscellaneous Surface Coating Operations |work=] |date=April 2008 |publisher=US Environmental Protection Agency |url=http://www.epa.gov/ttn/atw/area/paint_stripb.pdf |archive-url=https://web.archive.org/web/20161123143224/https://www3.epa.gov/ttn/atw/area/paint_stripb.pdf |archive-date=2016-11-23}}</ref>
			In the ], the ] (SCOEL) recommends an ] for DCM of 100&nbsp;ppm (8-hour time-weighted average) and a ] of 200&nbsp;ppm for a 15-minute period.<ref>{{cite report |url=https://echa.europa.eu/documents/10162/35144386/099_dichloromethane_oel_en.pdf |title=Recommendation from the Scientific Committee on Occupational Exposure Limits for methylene chloride (dichloromethane) |date=June 2009 |website=] |access-date=2023-09-07}}</ref> The ] voted in 2009 to ban the use of DCM in paint-strippers for consumers and many professionals,<ref name="EUban">{{cite web |url=https://www.paintsquare.com/news/view/?7328 |title=EU Banning Most DCM Paint Strippers |author=<!--Not stated--> |date=2012-03-09 |website=PaintSquare News |access-date=2023-09-07}}</ref> with the ban taking effect in December 2010.<ref>{{cite web |url=http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2010:086:0007:0012:EN:PDF |title=COMMISSION REGULATION (EU) No 276/2010 (Official Journal of the European Union, L 86/7) |date=2010-04-01 |access-date=2012-02-07}}</ref>
			In February 2013, the US ] (OSHA) and the ] 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.<ref name=Hazard>{{cite web |url = http://www.osha.gov/dts/hazardalerts/methylene_chloride_hazard_alert.html |title = Methylene Chloride Hazards for Bathtub Refinishers |work = OSHA-NIOSH Hazard Alert 2013-110 |publisher = OSHA and NIOSH |access-date = 22 January 2015}}</ref><ref name=NIOSHblog/><ref name="quicktake020113">, February 1, 2013;</ref> OSHA has since then issued a DCM standard.<ref name="oshastandard">. Occupational Safety & Health Administration. osha.gov</ref>
			On March 15, 2019, the US ] (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.<ref>{{cite web|url= https://www.epa.gov/newsreleases/epa-proposes-ban-all-consumer-most-industrial-and-commercial-uses-methylene-chloride|title=EPA Proposes Ban on All Consumer, Most Industrial and Commercial Uses of Methylene Chloride to Protect Public Health|date=2023-04-20}}</ref> 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.<ref>{{cite web|url= https://www.epa.gov/newsreleases/biden-harris-administration-finalizes-ban-most-uses-methylene-chloride-protecting|title=Biden-Harris Administration Finalizes Ban on Most Uses of Methylene Chloride, Protecting Workers and Communities from Fatal Exposure |date=2024-04-30}}</ref>
			==Environmental effects==
			) in the lower atmosphere (]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in ].]]
			Dichloromethane is not classified as an ozone-depleting substance by the ].<ref>{{cite web|url=https://www.epa.gov/ozone-layer-protection/ozone-depleting-substances|author=United States Environmental Protection Agency|title=Ozone-Depleting Substances|date=2015-07-17|access-date=April 20, 2018}}</ref> The US ] does not regulate dichloromethane as an ].<ref>{{cite web|url=https://nepis.epa.gov/Exe/tiff2png.cgi/50000S6R.PNG?-r+75+-g+7+D%3A%5CZYFILES%5CINDEX%20DATA%5C95THRU99%5CTIFF%5C00000344%5C50000S6R.TIF|author=United States Environmental Protection Agency|title=Questions and Answers on Ozone-Depleting Solvents and Their Substitutes|date=October 1995|access-date=April 20, 2018}}</ref> 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.<ref>{{cite web|url=https://public-old.wmo.int/en/resources/library/scientific-assessment-of-ozone-depletion-2018|archive-url=https://web.archive.org/web/20231218174345/https://public-old.wmo.int/en/resources/library/scientific-assessment-of-ozone-depletion-2018|url-status=dead|archive-date=December 18, 2023|author=World Meteorological Organization, United Nations Environmental Program|title=Scientific Assessment of Ozone Depletion: 2018|date=15 April 2020 }}</ref> Atmospheric abundances of dichloromethane have been increasing in recent years.
			==See also==
			*]
			*]
			*]
			*]
			*]
			*]
	==References==		==References==
	{{Reflist}}		{{reflist|30em}}
	==External links==		==External links==
			{{Commons category|Dichloromethane}}
	* {{ICSC|0058|00}}		* {{ICSC|0058|00}}
	* {{PGCH|0414}}		* {{PGCH|0414}}
	*		*
			*
	*
	*
	*		*
	*		*
			*
			*
	{{Halomethanes}}		{{Halomethanes}}
			{{GABAAR PAMs}}
			{{Authority control}}
	]
			]
	]		]
	]		]
Line 106:		Line 196:
	]		]
	]		]
	]		]
			]
			]
	]
			]
	]
			]
	]
			]
	]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]