The

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

1,2-dichloroethane, commonly known as ethylene dichloride (EDC), is a

chlorinated hydrocarbon An organochloride, organochlorine compound, chlorocarbon, or chlorinated hydrocarbon is an organic compound containing at least one covalently bonded atom of chlorine. The chloroalkane class (alkanes with one or more hydrogens substituted by chlo ...

. 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 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 polyvinyl chloride (PVC ...

, 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 compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon chemical bond, bonds. Due to carbon's ability to Catenation, catenate (form chains with other carbon atoms), millions of organic c ...

s, and as a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

. It forms

azeotrope An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be altered or changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This ...

s with many other

s, including water (at a boiling point of ) and other chlorocarbons.

History

In 1794, physician Jan Rudolph Deiman, merchant Adriaan Paets van Troostwijk, chemist Anthoni Lauwerenburg, and botanist Nicolaas Bondt, under the name of Society of Dutch Chemists ( nl, Gezelschap der Hollandsche Scheikundigen), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and

chlorine Chlorine is a chemical element with the symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate between them. Chlorine i ...

gas. Although the ''Gezelschap'' in practice did not do much in-depth scientific research, they and their publications were highly regarded. Part of that acknowledgement is that 1,2-dichloroethane was called "Dutch oil" in old chemistry. This is also the origin of the archaic term "olefiant gas" (oil-making gas) for ethylene, for in this reaction it is ethylene that makes the Dutch oil. And "olefiant gas" is the etymological origin of the modern term "olefins", the family of hydrocarbons of which ethylene is the first member.

Production

Nearly 20 million tons of 1,2-dichloroethane are produced annually in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territori ...

Western Europe Western Europe is the western region of Europe. The region's countries and territories vary depending on context. The concept of "the West" appeared in Europe in juxtaposition to "the East" and originally applied to the ancient Mediterranean ...

, and Japan. Production is primarily achieved through the iron(III) chloride- catalysed reaction of ethylene and chlorine: : ( Δ''H''^⊖_r = −218 kJ/mol) 1,2-dichloroethane is also generated by the copper(II) chloride-catalysed oxychlorination of ethylene: : +

Uses

Vinyl chloride monomer (VCM) production

Approximately 95% of the world's production of 1,2-dichloroethane is used in the production of

monomer In chemistry, a monomer ( ; '' mono-'', "one" + ''-mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification ...

(VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride. : The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above.

Other uses

1,2-Dichloroethane has been used as degreaser and paint remover but is now banned from use due to its

toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subs ...

and possible carcinogenity. As a useful 'building block' reagent, it is used as an intermediate in the production of diverse organic compounds such as ethylenediamine. In the laboratory it is occasionally used as a source of

, with elimination of ethene and chloride. Via several steps, 1,2-dichloroethane is a precursor to

1,1,1-trichloroethane The organic compound 1,1,1-trichloroethane, also known as methyl chloroform, is a chloroalkane. This colorless, sweet-smelling liquid was once produced industrially in large quantities for use as a solvent. It is regulated by the Montreal Prot ...

, which is used in

dry cleaning Dry cleaning is any cleaning process for clothing and textiles using a solvent other than water. Dry cleaning still involves liquid, but clothes are instead soaked in a water-free liquid solvent. Tetrachloroethylene (perchloroethylene), known i ...

. Historically, before leaded petrol was phased out, 1,2-dichloroethane was used as an anti-knock additive in petrol as a scavenging agent to prevent lead buildup.

Safety

1,2-Dichloroethane is highly flammable and releases

hydrochloric acid Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbol ...

when combusted: : + It is also toxic (especially by inhalation due to its high

vapour pressure Vapor pressure (or vapour pressure in English-speaking countries other than the US; see spelling differences) or equilibrium vapor pressure is defined as the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phase ...

) and possibly carcinogenic. Its high

solubility In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solub ...

and 50-year half-life in anoxic aquifers make it a perennial pollutant and health risk that is very expensive to treat conventionally, requiring a method of

bioremediation Bioremediation broadly refers to any process wherein a biological system (typically bacteria, microalgae, fungi, and plants), living or dead, is employed for removing environmental pollutants from air, water, soil, flue gasses, industrial effluent ...

. While the chemical is not used in consumer products manufactured in the U.S., a case was reported in 2009 of molded plastic consumer products (toys and holiday decorations) from China that released 1,2-dichloroethane into homes at levels high enough to produce cancer risk. Substitutes are recommended and will vary according to application. Dioxolane and

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) a ...

are possible substitutes as solvents.

Dichloroethane Dichloroethane can refer to either of two isomeric organochlorides with the molecular formula C2H4Cl2: * 1,1-Dichloroethane (ethylidene chloride) * 1,2-Dichloroethane The chemical compound 1,2-dichloroethane, commonly known as ethylene dichlori ...

is unstable in the presence of aluminium metal and, when moist, with

zinc Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodi ...

and

iron Iron () is a chemical element with Symbol (chemistry), symbol Fe (from la, Wikt:ferrum, ferrum) and atomic number 26. It is a metal that belongs to the first transition series and group 8 element, group 8 of the periodic table. It is, Abundanc ...

References

External links

Gezelschap der Hollandsche Scheikundigen

Merck Chemicals database

* ttp://www.epa.gov/ttn/chief/le/ethyldi.pdf Locating and estimating air emissions from sources of ethylene dichloride, EPA report EPA-450/4-84-007d, March 1984 {{DEFAULTSORT:Dichloroethane, 1, 2- Hazardous air pollutants IARC Group 2B carcinogens Organochloride insecticides Chloroalkanes Plastics Halogenated solvents Fuel additives