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Dichloromethane



Dichloromethane
IUPAC name Dichloromethane
Other names Methylene chloride, methylene dichloride, Solmethine, Narkotil, Solaesthin, Di-clo, Freon 30, R-30, DCM, UN 1593, MDC
Identifiers
CAS number 75-09-2
PubChem 6344
EINECS number 200-838-9
KEGG C02271
ChEBI 15767
RTECS number PA8050000
SMILES C(Cl)Cl
InChI InChI=1/CH2Cl2/c2-1-3/h1H2
Properties
Molecular formula CH2Cl2
Molar mass 84.93 g/mol
Appearance Colorless liquid
Density 1.3255 g/cm³, liquid
Melting point

-96.7 °C (175.7 K)

Boiling point

39 °C (312.8 K)

Solubility in water 13 g/l at 20 °C
Vapor pressure 47 kPa at 20 ºC
Hazards
Main hazards Harmful (Xn), Carc. Cat. 2B
NFPA 704
0
2
0
 
R-phrases R40
S-phrases S23, S24/25, S36/37
Flash point None
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

 

Dichloromethane (DCM) or methylene chloride is the chemical compound with the formula CH2Cl2. It is a colorless, volatile liquid with a moderately sweet aroma. It is widely used as a solvent, the general view being that it is one of the less harmful of the chlorocarbons, and it is miscible with most organic solvents.

Dichloromethane 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.

Additional recommended knowledge

Contents

Production

Industrially, dichloromethane is produced by reacting 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.

CH4 + Cl2CH3Cl + HCl
CH3Cl + Cl2CH2Cl2 + HCl
CH2Cl2 + Cl2CHCl3 + HCl
CHCl3 + Cl2CCl4 + 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 an ideal solvent for many chemical processes. It is widely used as a paint stripper and a degreaser. In the food industry, it was previously used to decaffeinate coffee and to prepare extracts of hops and other flavorings, but most companies no longer use it.[1]. It is used to chemically weld certain plastics (for example, it is used to seal the casing of electric meters). Its volatility has led to its use as an aerosol spray propellant and as a blowing agent for polyurethane foams. It is also used as a fumigant pesticide for stored strawberries and grains. It is also the most common "active" component in Drinking Birds. Concerns about its health effects have led to a search for alternatives in many of these applications.

It is used in Christmas lights called bubble lights, in a sealed vial which bubbles when the incandescent light bulb below it is lit. Wurlitzer also used it in their 1940's "bubbler" style jukeboxes. The bubble tubes were up to 30 inches long and used resistors to provide the heat to boil the liquid in a small constricted chamber that had bits of rock and a special glass valve to concentrate the small bubbles into larger ones. It is still used today in their reproduction machines.

Often sold under the brand name of "EMA Plastic Weld" it is also used extensively in the modelmaking industry for joining plastic components together - it is commonly referred to as "Di-clo".

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. Dichloromethane is also metabolised by the body to carbon monoxide potentially leading to carbon monoxide poisoning.[2] Prolonged skin contact can result in the dichloromethane dissolving some of the fatty tissues in skin, resulting in skin irritation or chemical burns.[3]

It may be carcinogenic, as it has been linked to cancer of the lungs, liver, and pancreas in laboratory animals.[4] Dichloromethane crosses the placenta. Fetal toxicity in women who are exposed to it during pregnancy however has not been proven.[5] In animal experiments it was fetotoxic at doses that were maternally toxic but no teratogenic effects were seen.[4]

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

See also

  • Haloalkane
  • Halomethane

References

  1. ^ Office of Environmental Health Hazard Assessment (September 2000). Dichloromethane. Public Health Goals for Chemicals in Drinking Water. California Environmental Protection Agency.
  2. ^ Fagin J, Bradley J, Williams D (1980). "Carbon monoxide poisoning secondary to inhaling methylene chloride". Br Med J 281 (6253): 1461. PMID 7437838.
  3. ^ Wells G, Waldron H (1984). "Methylene chloride burns". Br J Ind Med 41 (3): 420. PMID 6743591.
  4. ^ a b USDHHS. Toxicological Profile for Methylene Chloride. Retrieved on 2006-09-10.
  5. ^ 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. PMID 1855488.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dichloromethane". A list of authors is available in Wikipedia.
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