Chloroethane

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Chloroethane
Skeletal formula of chloroethane Chloroethane-skeletal.svg
Skeletal formula of chloroethane
Skeletal formula of chloroethane with stereo bonds Chloroethane-2D.svg
Skeletal formula of chloroethane with stereo bonds
Chloroethane-3D-vdW.png
Names
Preferred IUPAC name
Chloroethane
Other names
Ethyl chloride, Monochloroethane, Chlorene, Muriatic ether, EtCl, UN 1037, Hydrochloric Ether, Chelen, Kelene [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.755 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
RTECS number
  • KH7525000
UNII
  • InChI=1S/C2H5Cl/c1-2-3/h2H2,1H3 Yes check.svgY
    Key: HRYZWHHZPQKTII-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H5Cl/c1-2-3/h2H2,1H3
    Key: HRYZWHHZPQKTII-UHFFFAOYAJ
  • ClCC
Properties
C2H5Cl
Molar mass 64.51 g·mol−1
AppearanceColorless gas
Odor Pungent, ethereal [2]
Density 0.921 g/cm3 (0-4 °C) [3]
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 [4]
0.447 g/100 mL (0 °C)
0.574 g/100 mL (20 °C) [5] [4]
Solubility Soluble in alcohol, ether [6]
Solubility in ethanol 48.3 g/100 g (21 °C) [4]
Vapor pressure 8.4 kPa (-40 °C)
62.3 kPa (0 °C) [7]
134.6 kPa (20 °C) [2]
11.1 L·atm/mol (24 °C) [2]
1.3676 (20 °C)
1.001 (25 °C) [2]
Viscosity 0.279 cP (10 °C) [2]
Structure
2.06 D
Thermochemistry
104.3 J/mol·K [4]
Std molar
entropy (S⦵298)
275.7 J/mol·K [4]
-137 kJ/mol [4] [7]
-59.3 kJ/mol [4]
Pharmacology
N01BX01 ( WHO )
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-silhouette.svg [3]
Danger
H220, H280, H351, H412 [3]
P210, P273, P281, P410+P403 [3]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
4
2
Flash point −43 °C (−45 °F; 230 K)
open cup [5]
−50 °C (−58 °F; 223 K)
closed cup [3] [6]
494 to 519 °C (921 to 966 °F; 767 to 792 K) [4] [6]
Explosive limits 3.8%-15.4% [8]
Lethal dose or concentration (LD, LC):
59,701 ppm (rat, 2 hr)
54,478 ppm (mouse, 2 hr)
[9]
40,000 ppm (guinea pig, 45 min) [9]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1000 ppm (2600 mg/m3) [8]
REL (Recommended)
Handle with caution in the workplace. [8]
IDLH (Immediate danger)
3800 ppm [8]
Legal status
Related compounds
Related haloalkanes
1,1-dichloroethane

1,2-dichloroethane
1,1,1-trichloroethane
1,1,2-trichloroethane
bromoethane
chloromethane

Contents

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor. [11]

Ethyl chloride was first synthesised by Basil Valentine by reacting ethanol and hydrochloric acid in 1440. [11] Glauber made it in 1648 by reacting ethanol and zinc chloride. [11]

Production

Chloroethane is produced by hydrochlorination of ethylene: [11]

C2H4 + HCl → C2H5Cl

At various times in the past, chloroethane has also been produced from ethanol and hydrochloric acid, from ethane and chlorine, or from ethanol and phosphorus trichloride, but these routes are no longer economical. Some chloroethane is generated as a byproduct of polyvinyl chloride production.

Uses

Chloroethane is an inexpensive ethylating agent. It reacts with aluminium metal to give ethylaluminium sesquichloride, a precursor to polymers and other useful organoaluminium compounds. [12] Chloroethane is used to convert cellulose to ethylcellulose, a thickening agent and binder in paints, cosmetics, and similar products.

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.

Obsolete 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. [11]

Niche uses

Bottle of compressed EtCl for anaesthesia Bottle of Aethylum chloratum pro narcosi.JPG
Bottle of compressed EtCl for anaesthesia

Chloroethane has a low boiling point, so when applied topically, the heat absorbed by the boiling liquid produces a deep and rapid chill. When sprayed on the skin, this chill has a mild anesthetic effect, which can be useful when removing splinters or incising abscesses in a clinical setting. Chloroethane was standard equipment in casualty wards.[ when? ] It was commonly used to induce general anaesthesia before continuing with di-ethyl ether, which has a much slower uptake.[ citation needed ] 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; if the tooth is still alive this should be sensed by the patient as mild discomfort that subsides when the wad is removed.[ citation needed ]

Recreational drug

Chloroethane is a recreational inhalant drug, although it should not be confused with a duster or canned air, which is composed of fluorinated low-weight hydrocarbons such as tetrafluoromethane, chlorodifluoromethane or another similar gas.

In Brazil, it is a major component of a traditional (though illegal) drug taken during Carnaval, known locally as "lança-perfume" [13] (lit. perfume launcher or sprayer).

Safety

The vapor is flammable and narcotic, which requires care.[ citation needed ]

Monochloroethane 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; most commercially available handheld containers contain 30% per volume of concentrated vapors that 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 roused 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 their side. This constitutes a medical emergency and requires prompt action. It is advised to move the victim to clear air and administer 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. Singer Darius Campbell Danesh died of "toxic effects of chloroethane" as well as suffocation. [14]

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.

While chloroethane is not classified as carcinogenic to humans specifically, [15] It is still used in medicine as a local anesthetic. [16]

Related Research Articles

Chloroform, or trichloromethane, is an organic compound with the formula CHCl3 and a common solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to refrigerants and in turn, PTFE. Chloroform is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. Chloroform was used as an anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">Tetrachloroethylene</span> Chemical compound in very wide use

Tetrachloroethylene, also known under the systematic name tetrachloroethene, or perchloroethylene, and abbreviations such as "perc" (or "PERC"), and "PCE", is a chlorocarbon with the formula Cl2C=CCl2. It is a colorless liquid widely used for dry cleaning of fabrics, hence it is sometimes called "dry-cleaning fluid". It also has its uses as an effective automotive brake cleaner. It has a mild sweet odor, similar to the smell of chloroform, detectable by most people at a concentration of 1 part per million (1 ppm).

<span class="mw-page-title-main">Dichloromethane</span> Chemical compound

Dichloromethane is an organochlorine compound with the formula CH2Cl2. This colorless, volatile liquid with a chloroform-like, sweet odor is widely used as a solvent. Although it is not miscible with water, it is slightly polar, and miscible with many organic solvents.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.

<span class="mw-page-title-main">Vinyl chloride</span> Chemical compound

Vinyl chloride is an organochloride with the formula H2C=CHCl. It is also called vinyl chloride monomer (VCM) or chloroethene. This colorless compound is an important industrial chemical chiefly used to produce the polymer, poly(vinyl chloride) (PVC). Vinyl chloride monomer is among the top twenty largest petrochemicals (petroleum-derived chemicals) in world production. The United States remains the largest vinyl chloride manufacturing region because of its low-production-cost position in chlorine and ethylene raw materials. China is also a large manufacturer and one of the largest consumers of vinyl chloride. Vinyl chloride is a flammable gas that has a sweet odor and is carcinogenic. It can be formed in the environment when soil organisms break down chlorinated solvents. Vinyl chloride that is released by industries or formed by the breakdown of other chlorinated chemicals can enter the air and drinking water supplies. Vinyl chloride is a common contaminant found near landfills. Before the 1970s, vinyl chloride was used as an aerosol propellant and refrigerant.

<span class="mw-page-title-main">1,1,1-Trichloroethane</span> Chemical compound

The organic compound 1,1,1-trichloroethane, also known as methyl chloroform and chlorothene, is a chloroalkane with the chemical formula CH3CCl3. It is an isomer of 1,1,2-trichloroethane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Protocol as an ozone-depleting substance and its use is being rapidly phased out.

<span class="mw-page-title-main">Trichloroethylene</span> Chemical compound

Trichloroethylene (TCE) is a halocarbon with the formula C2HCl3, commonly used as an industrial degreasing solvent. It is a clear, colourless, non-flammable, volatile liquid with a chloroform-like pleasant mild smell. The IUPAC name is trichloroethene. Industrial abbreviations include TCE, trichlor, Trike, Tricky and tri. It should not be confused with the similar 1,1,1-trichloroethane, which is commonly known as chlorothene.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene is an aromatic organic compound with the chemical formula C6H5Cl. This colorless, flammable liquid is a common solvent and a widely used intermediate in the manufacture of other chemicals.

The chemical compound 1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a chlorinated hydrocarbon. It is a colourless liquid with a chloroform-like odour. The most common use of 1,2-dichloroethane is in the production of vinyl chloride, which is used to make polyvinyl chloride (PVC) pipes, furniture and automobile upholstery, wall coverings, housewares, and automobile parts. 1,2-Dichloroethane is also used generally as an intermediate for other organic chemical compounds, and as a solvent. It forms azeotropes with many other solvents, including water and other chlorocarbons.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

1,1-Dichloroethene, commonly called 1,1-dichloroethylene or vinylidene chloride or 1,1-DCE, is an organochloride with the molecular formula C2H2Cl2. It is a colorless liquid with a sharp odor. Like most chlorocarbons, it is poorly soluble in water, but soluble in organic solvents. 1,1-DCE was the precursor to the original clingwrap, Saran, for food, but this application has been phased out.

1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.

<span class="mw-page-title-main">1,1,2,2-Tetrachloroethane</span> Chemical compound

1,1,2,2-tetrachloroethane (TeCA), also known by the brand names Bonoform, Cellon and Westron, is an organic compound. It is colorless liquid and has a sweet odor. It is used as an industrial solvent and as a separation agent. TeCA is toxic and it can be inhaled, consumed or absorbed through the skin. After exposure, nausea, dizziness or even liver damage may occur.

<span class="mw-page-title-main">Hexachlorobutadiene</span> Chemical compound

Hexachlorobutadiene, (often abbreviated as "HCBD") Cl2C=C(Cl)C(Cl)=CCl2, is a colorless liquid at room temperature that has an odor similar to that of turpentine. It is a chlorinated aliphatic diene with niche applications but is most commonly used as a solvent for other chlorine-containing compounds. Structurally, it has a 1,3-butadiene core, but fully substituted with chlorine atoms.

<span class="mw-page-title-main">Perchloromethyl mercaptan</span> Chemical compound

Perchloromethyl mercaptan is the organosulfur compound with the formula CCl3SCl. It is mainly used as an intermediate for the synthesis of dyes and fungicides (captan, folpet). It is a colorless oil, although commercial samples are yellowish. It is insoluble in water but soluble in organic solvents. It has a foul, unbearable, acrid odor. Perchloromethyl mercaptan is the original name. The systematic name is trichloromethanesulfenyl chloride, because the compound is a sulfenyl chloride, not a mercaptan.

References

  1. ↑ Helbing, H. (1895). Modern materia medica for pharmacists, medical men, and students. USA: Lehn & Fink.
  2. 1 2 3 4 5 CID 6337 from PubChem
  3. 1 2 3 4 5 Sigma-Aldrich Co., Chloroethane. Retrieved on 2014-05-26.
  4. 1 2 3 4 5 6 7 8 "Chloroethane".
  5. 1 2 "Summary of Emissions Associated with Sources of Ethyl Chloride". nepis.epa.gov. National Service Center for Environmental Publications (NSCEP). Retrieved 2014-05-26.
  6. 1 2 3 "Material Safety Data Sheet" (PDF). www.mathesongas.com. Matheson Tri-Gas, Inc. Retrieved 2014-05-26.
  7. 1 2 Ethyl chloride in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD) (retrieved 2014-05-26)
  8. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0267". National Institute for Occupational Safety and Health (NIOSH).
  9. 1 2 "Ethyl chloride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  10. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  11. 1 2 3 4 5 Rossberg, M.; Lendle, W.; Pfleiderer, G.; Tögel, A.; Dreher, E. L.; Langer, E.; Rassaerts, H.; Kleinschmidt, P.; Strack (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a06_233.pub2.
  12. ↑ Krause, M.J.; Orlandi, F.; Saurage, A.T.; Zietz, Jr., J.R. (2000). "Aluminum Compounds". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_543.
  13. ↑ Melnick, Meredith (2 December 2010). "What's Lança-Perfume? The Drug from Rio's Bust You've Never Heard of". Time.
  14. ↑ "Darius Campbell Danesh died of inhalation of chloroethane". TheGuardian.com . 10 September 2022.
  15. ↑ Chloroethane, IARC
  16. ↑ "Chloroethane".
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