Pentachloroethane

Pentachloroethane
Names
Preferred IUPAC name
Pentachloroethane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.842 Edit this at Wikidata
EC Number
  • 200-925-1
KEGG
RTECS number
  • KI6300000
UNII
UN number 1669
  • InChI=1S/C2HCl5/c3-1(4)2(5,6)7/h1H
    Key: BNIXVQGCZULYKV-UHFFFAOYSA-N
  • InChI=1/C2HCl5/c3-1(4)2(5,6)7/h1H
    Key: BNIXVQGCZULYKV-UHFFFAOYAS
  • C(C(Cl)(Cl)Cl)(Cl)Cl
Properties
C2HCl5
Molar mass 202.09 g mol−1
Appearance Colorless liquid
Odor Sweetish, chloroform-like
Density 1.68 g cm−3
Melting point −29 °C (−20 °F; 244 K)
Boiling point 162 °C (324 °F; 435 K)
0.05% (20°C)[1]
Vapor pressure 3 mmHg (20°C)[1]
-99.1·10−6 cm3/mol
Hazards
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Danger
H351, H372, H411
P201, P202, P260, P264, P270, P273, P281, P308+P313, P314, P391, P405, P501
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 Handle with care in the workplace[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentachloroethane is a chemical compound of chlorine, hydrogen, and carbon with the chemical formula C2HCl5. It is a colourless non-flammable liquid that is used as a solvent for oil and grease, in metal cleaning, and in the separation of coal from impurities.

Production and uses

Victor Regnault obtained Pentachloroethane from chlorination of various chlorinated ethanes in 1839.[2]

Pentachloroethane can be obtained by chlorination of trichloroethylene and ethylene-catalysed chlorination of 1,2-dichloroethane.[3] Pentachloroethane can also be obtained by the reaction of acetylene and chlorine, catalysed by aluminium chloride and antimony trichloride.[4] It can be made as a byproduct of tetrachloroethylene production.

Pentachloroethane has limited uses as a solvent for oils and grease (especially in metal cleaning), in soil sterilisation, to remove impurities in coal and as a desiccant agent for wood. It was formerly used as a dry-cleaning solvent for a short time. It is rarely used since there are safer and more economical alternatives such as tetrachloroethylene.

It can be used as a precursor to tetrachloroethylene.[5] Activated carbon-catalysed reaction of pentachloroethane and calcium chloride gives tetrachloroethylene by dehydrochlorination.

Safety

Although it is not flammable, pentachloroethane can oxidise to give phosgene and trichloroacetyl chloride in presence of oxygen at high temperatures. Pentachloroethane is not biodegradable and it can be toxic to aquatic life. It is toxic for humans.[citation needed]

References

  1. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0482". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Quadrichlorinated Hydrochloric Ether in Gmelin, L., Hand-book of Chemistry
  3. ^ NLM Hazardous Substances Data Bank entry for [ ]
  4. ^ Jian, Panming; He, Yongzhi. Method for producing pentachloroethane using acetylene and chlorine. 2018. CN 108546228 A
  5. ^ Sittig's Handbook of Toxic and Hazardous Chemicals and Carcinogens, p. 2067, ISBN 1-4377-7869-0.