Chloroethane

Chloroethane

Names
IUPAC name Chloroethane
Other names Ethyl chloride, Monochloroethane, Chlorene, Muriatic ether, EtCl, UN 1037, Hydrochloric ether
Identifiers
ATC code	N01BX01
CAS Registry Number	75-00-3 Y
ChEBI	CHEBI:47554 Y
ChEMBL	ChEMBL46058 Y
ChemSpider	6097 Y
InChI InChI=1S/C2H5Cl/c1-2-3/h2H2,1H3 Y Key: HRYZWHHZPQKTII-UHFFFAOYSA-N Y InChI=1/C2H5Cl/c1-2-3/h2H2,1H3 Key: HRYZWHHZPQKTII-UHFFFAOYAJ
Jmol-3D images	Image
KEGG	D04088 Y
PubChem	6337
RTECS number	KH7525000
SMILES ClCC
UNII	46U771ERWK Y
Properties
Molecular formula	C2H5Cl
Molar mass	64.51 g·mol−1
Appearance	Colorless gas
Odor	Pungent, ethereal[1]
Density	0.921 g/cm3 (0-4 °C)[2] 0.8898 g/cm3 (25 °C)
Melting point	−138.7 °C (−217.7 °F; 134.5 K)
Boiling point	12.27 °C (54.09 °F; 285.42 K) decomposes at 510 °C[3]
Solubility in water	0.447 g/100 mL (0 °C) 0.574 g/100 mL (20 °C)[4][3]
Solubility	Soluble in alcohol, ether[5]
Solubility in ethanol	48.3 g/100 g (21 °C)[3]
Vapor pressure	8.4 kPa (-40 °C) 62.3 kPa (0 °C)[6] 134.6 kPa (20 °C)[1]
Henry's law constant (kH)	11.1 L·atm/mol (24 °C)[1]
Refractive index (nD)	1.3676 (20 °C) 1.001 (25 °C)[1]
Viscosity	0.279 cP (10 °C)[1]
Structure
Dipole moment	2.06 D
Thermochemistry
Specific heat capacity (C)	104.3 J/mol·K[3]
Std molar entropy (So298)	190.8 J/mol·K[3]
Std enthalpy of formation (ΔfHo298)	-137 kJ/mol[6][3]
Gibbs free energy (ΔfG˚)	-59.3 kJ/mol[3]
Hazards
Main hazards	Flammable
GHS pictograms	[2]
GHS signal word	Danger
GHS hazard statements	H220, H280, H351, H412[2]
GHS precautionary statements	P210, P273, P281, P410+403[2]
EU classification	F+ Xn
R-phrases	R12, R40, R52/53
S-phrases	S9, S16, S33, S36/37, S61
NFPA 704	4 2 2
Flash point	−43 °C (−45 °F; 230 K) open cup[4] −50 °C (−58 °F; 223 K) closed cup[5][2]
Autoignition temperature	494 to 519 °C (921 to 966 °F; 767 to 792 K)[3][5]
Explosive limits	3.8%-15.4%[7]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 1000 ppm (2600 mg/m3)[7]
REL (Recommended)	Handle with caution in the workplace.[7]
IDLH (Immediate danger)	3800 ppm[7]
Related compounds
Related haloalkanes	1,1-dichloroethane 1,2-dichloroethane 1,1,1-trichloroethane 1,1,2-trichloroethane bromoethane chloromethane
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Chloroethane or monochloroethane, commonly known by its old name ethyl chloride, is a chemical compound with chemical formula C
2H
5Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.

Production

Chloroethane is produced by hydrochlorination of ethene:

C₂H₄ + HCl → C₂H₅Cl

At various times in the past, chloroethane has also been produced from ethanol and hydrochloric acid, or from ethane and chlorine, but these routes are no longer economical. Some chloroethane is generated as a byproduct of polyvinyl chloride production. Should demand for chloroethane continue to fall to the point where making it for its own sake is not economical, this may become the leading source of the chemical.

Uses

Beginning in 1922 and continuing through most of the 20th century, the major use of chloroethane was to produce tetraethyllead (TEL), an anti-knock additive for gasoline. TEL has been or is being phased out in most of the industrialized world, and the demand for chloroethane has fallen sharply. It also reacts with aluminium metal to give ethylaluminium sesquichloride, a precursor to polymers and other useful organoaluminium compounds.^[8]

Like other chlorinated hydrocarbons, chloroethane has been used as a refrigerant, an aerosol spray propellant, an anesthetic, and a blowing agent for foam packaging. For a time it was used as a promoter chemical in the aluminium chloride catalyzed process to produce ethylbenzene, the precursor for styrene monomer. At present though, it is not widely used in any of these roles.

The only remaining industrially important use of chloroethane is in treating cellulose to make ethylcellulose, a thickening agent and binder in paints, cosmetics, and similar products.

Chloroethane is supplied as a liquid in a spray bottle propelled by its own vapor pressure. It acts as a mild topical anesthetic by its chilling effect when sprayed on skin, such as when removing splinters in a clinical setting. The heat absorbed by the boiling liquid on tissues produces a deep and rapid chill, but since the boiling point is well above the freezing point of water, it presents no danger of frostbite. The vapor is flammable and narcotic, which requires care.

Chloroethane is a recreational inhalant drug, although it should not be confused with "Duster", a term used to describe "canned air", a term used to describe fluorinated low weight hydrocarbon, such as tetrafluorethane, chlorodifluoromethane or another similar gas. Similar to poppers, ethyl chloride is used as an inhalant (huffed) during sexual activity, primarily by gay men. In Brazil, it is a traditional (though illegal) drug taken during Carnaval parades, known as "lança-perfume".^{[9]reference does not define lança-perfume}{cn}

In dentistry, chloroethane is used as one of the means of diagnosing a 'dead tooth', i.e. one in which the pulp has died. A small amount of the substance is placed on the suspect tooth using a cotton wad. Chloroethane's low boiling point creates a localised chilling effect. If the tooth is still alive this should be sensed by the patient as mild discomfort that subsides when the wad is removed.

Safety

Chloroethane is the least toxic of the chloroethanes. Like other chlorinated hydrocarbons, it is a central nervous system depressant, albeit a less potent one than many similar compounds. People breathing its vapors at less than 1% concentration in air usually experience no symptoms. At concentrations of 3% to 5%, victims usually exhibit symptoms similar to those of alcohol intoxication. Breathing its vapors at >15% concentration is often fatal but most commercially available handheld containers contain a total of 30% per volume of concentrated vapors which naturally disperse in the outside air.

If exposed to concentrations higher than 6% to 8% victims often exhibit shallow breathing, loss of consciousnesses, and depressed heart-rate. They can be aroused with physical contact or loud noise. At this point removal from the area of exposure is advised to restore consciousness. The long-term effects of exposure over a period of 4 or more hours will cause side effects similar to alcoholic hang-over with dehydration, dizziness, loss of clear vision and temporary loss of consciousness, which can last an hour or more. If no longer exposed to the gas, a victim will return to normal health quickly. This can be helped with intake of extra fluids, vitamins, and sugars.

Toxic over-exposure starts at 9% to 12% concentrations, the heart rate drops further, the victim may have more shallow breathing or stop all together, they do not respond to any outside stimulation and may begin to involuntarily gasp, belch or vomit, which can lead to aspiration if the victim is not turned on his side. This constitutes a medical emergency and requires prompt action. It is advised to move the victim to clear air and administrator forced breathing for them to purge the lungs of the toxic fumes. If the victim recovers quickly enough, hospitalization may not be required, but will require a medical examination to ensure that no organ damage has occurred.

At >12% concentration, the victim's heart, lungs and kidneys begin to fail. Immediate CPR followed by medical support measures may be required to prevent fatal kidney, lung and heart failure.

Studies on the effects of chronic ethyl chloride exposure in animals have given inconsistent results, and no data exists for its long-term effects on humans. Some studies have reported that prolonged exposure can produce liver or kidney damage, or uterine cancer in mice, but these data have been difficult to reproduce.

Chloroethane is not classifiable as to its carcinogenicity to humans (Group 3).^[10]

Recent information suggests carcinogenic potential; it has been designated as ACGIH category A3, Confirmed Animal Carcinogen with Unknown Relevance to Humans. As a result, the State of California has incorporated it into Proposition 65 as a known carcinogen. Nonetheless, it is still used in medicine as a local anesthetic.

References

External links

Wikimedia Commons has media related to Chloroethane.

• International Chemical Safety Card 0132
• "NIOSH Pocket Guide to Chemical Hazards #0267". National Institute for Occupational Safety and Health (NIOSH). 
• IARC Monograph "Chloroethane."
• Ethyl chloride in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov
• National Pollutant Inventory - Chloroethane