Dichloromethane

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Dichloromethane
File:Dichloromethane.svg
File:Dichloromethane-3D-vdW.png
IUPAC name
Dichloromethane
Other names
Methylene chloride, methylene dichloride, Solmethine, Narkotil, Solaesthin, Di-clo, Freon 30, R-30, DCM, UN 1593, MDC
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 75-09-2 YesY
PubChem 6344
EC number 200-838-9
KEGG C02271
ChEBI 15767
RTECS number PA8050000
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InChI Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula CH2Cl2
Molar mass 84.93 g/mol
Appearance Colorless liquid
Density 1.3266 g/cm3, liquid
Melting point

-96.7 °C, 176 K, -142 °F

Boiling point

40 °C, 313 K, 104 °F

Solubility in water 13 g/L at 20 °C
Vapor pressure 47 kPa at 20 °C
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
R-phrases R40
S-phrases S23 S24/25 S36/37
NFPA 704
1
2
0
Flash point None
Autoignition
temperature 		556 °C
 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
File:Dichloromethane near IR spectrum.png
Near IR absorption spectrum of dichloromethane showing complicated overlapping overtones of mid IR absorption features.

Dichloromethane (DCM or methylene chloride) is an organic compound with the formula CH2Cl2. This colorless, volatile liquid with a moderately sweet aroma is widely used as a solvent. More than 500,000 tons were produced in 1991. Although it is not miscible with water, it is miscible with many organic solvents.[1] It was first prepared in 1840 by the French chemist Henri Victor Regnault, who isolated it from a mixture of chloromethane and chlorine that had been exposed to sunlight.

Production

Dichloromethane is produced by treating either methyl chloride or methane with chlorine gas at 400–500 °C. At these temperatures, both methane and methyl chloride undergo a series of reactions producing progressively more chlorinated products.[1]

CH4 + Cl2 → CH3Cl + HCl
CH3Cl + Cl2 → CH2Cl2 + HCl
CH2Cl2 + Cl2 → CHCl3 + HCl
CHCl3 + Cl2 → CCl4 + HCl

The output of these processes is a mixture of methyl chloride, dichloromethane, chloroform, and carbon tetrachloride. These compounds are separated by distillation.

Uses

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.[1]

It is widely used as a paint stripper and a degreaser. In the food industry, it has been used to decaffeinate coffee and tea as well as to prepare extracts of hops and other flavorings.[2] Its volatility has led to its use as an aerosol spray propellant and as a blowing agent for polyurethane foams.

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 plastic welding adhesives it is also used extensively in the model-making industry for joining plastic components together — it is commonly referred to as "Di-clo."

Also used in the garment printing industry for removal of heat-sealed garment transfers. Usually sold in cans with methanol as the propellant gas.[citation needed] Its volatility is exploited in novelty items — drinking birds, bubble lights, and jukebox displays.

Dichloromethane is used within the material testing field of civil engineering, specifically it is used during the testing of bituminous materials as a solvent to separate the binder from the aggregate of an asphalt or macadam to allow the testing of the materials.[3]

Toxicity

Dichloromethane is the least toxic of the simple chlorohydrocarbons, but it is not without its health risks as its high volatility makes it an acute inhalation hazard.[4] Dichloromethane is also metabolised by the body to carbon monoxide potentially leading to carbon monoxide poisoning.[5] Acute exposure by inhalation has resulted in optic neuropathy[6] and hepatitis.[7] Prolonged skin contact can result in the dichloromethane dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns.[8]

It may be carcinogenic, as it has been linked to cancer of the lungs, liver, and pancreas in laboratory animals.[9] Dichloromethane crosses the placenta. Fetal toxicity in women who are exposed to it during pregnancy however has not been proven.[10] In animal experiments it was fetotoxic at doses that were maternally toxic but no teratogenic effects were seen.[9]

In many countries products containing dichloromethane must carry labels warning of its health risks.

In the European Union, the European Parliament voted in 2009 to ban the use of dichloromethane in paint-strippers for consumers and many professionals.[11] The ban will take effect by December 2010.[citation needed]

References

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External links

Monosubstituted

CH3F · CH3Cl · CH3Br · CH3I

Disubstituted

CH2F2 · CH2ClF · CH2BrF · CH2FI · CH2Cl2 · CH2BrCl · CH2ClI · CH2Br2 · CH2BrI · CH2I2

Trisubstituted

CHF3 · CHClF2 · CHBrF2 · CHF2I · CHCl2F · C*HBrClF · C*HClFI · CHBr2F · C*HBrFI · CHFI2 · CHCl3 · CHBrCl2 · CHCl2I · CHBr2Cl · C*HBrClI · CHClI2 · CHBr3 · CHBr2I · CHBrI2 · CHI3

Tetrasubstituted

CF4 · CClF3 · CBrF3 · CF3I · CCl2F2 · CBrClF2 · CClF2I · CBr2F2 · CBrF2I · CF2I2 · CCl3F · CBrCl2F · CCl2FI · CBr2ClF · C*BrClFI · CClFI2 · CBr3F · CBr2FI · CBrFI2 · CFI3 · CCl4 · CBrCl3 · CCl3I · CBr2Cl2 · CBrCl2I · CCl2I2 · CBr3Cl · CBr2ClI · CBrClI2 · CClI3 · CBr4 · CBr3I · CBr2I2 · CBrI3 · CI4

ar:ثنائي كلورو الميثان

bs:Metilen hlorid cs:Dichlormethan da:Metylenklorid de:Dichlormethan et:Metüleenkloriid es:Cloruro de metileno fr:Dichlorométhane it:Diclorometano he:דיכלורומתאן lv:Metilēnhlorīds lb:Dichloromethan hu:Diklórmetán nl:Dichloormethaan ja:ジクロロメタン pl:Chlorek metylenu pt:Diclorometano ru:Дихлорметан fi:Dikloorimetaani sv:Diklormetan vi:Diclomêtan

zh:二氯甲烷
  1. ↑ 1.0 1.1 1.2 M. Rossberg et al. “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_233.pub2
  2. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  3. ↑ Shell Bitumen (2003-09-25). The Shell Bitumen Handbook. ISBN 9780727732200. 
  4. ↑ Rioux JP, Myers RA (1988). "Methylene chloride poisoning: a paradigmatic review". J Emerg Med. 6 (3): 227–238. doi:10.1016/0736-4679(88)90330-7. PMID 3049777. 
  5. ↑ Fagin J, Bradley J, Williams D (1980). "Carbon monoxide poisoning secondary to inhaling methylene chloride". Br Med J. 281 (6253): 1461. doi:10.1136/bmj.281.6253.1461. PMC 1714874 Freely accessible. PMID 7437838. 
  6. ↑ Kobayashi A, Ando A, Tagami N, Kitagawa M, Kawai E, Akioka M, Arai E, Nakatani T, Nakano S, Matsui Y, Matsumura M (2008). "Severe optic neuropathy caused by dichloromethane inhalation". J Ocul Pharmacol and Ther. 24 (6): 607–612. doi:10.1089/jop.2007.0100. PMID 19049266. 
  7. ↑ Cordes DH, Brown WD, Quinn KM (1988). "Chemically induced hepatitis after inhaling organic solvents". West J Med. 148 (4): 458–460. PMC 1026148 Freely accessible. PMID 3388849. 
  8. ↑ Wells G, Waldron H (1984). "Methylene chloride burns". Br J Ind Med. 41 (3): 420. PMC 1009322 Freely accessible. PMID 6743591. 
  9. ↑ 9.0 9.1 USDHHS. "Toxicological Profile for Methylene Chloride" (PDF). Retrieved 2006-09-10. 
  10. ↑ Bell B, Franks P, Hildreth N, Melius J (1991). "Methylene chloride exposure and birthweight in Monroe County, New York". Environ Res. 55 (1): 31–9. doi:10.1016/S0013-9351(05)80138-0. PMID 1855488. 
  11. ↑ "Dichloromethane to be banned in paint-strippers". 2009-01-14. Retrieved 2009-01-15. 
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