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. It is a colourless
liquid
Liquid is a state of matter with a definite volume but no fixed shape. Liquids adapt to the shape of their container and are nearly incompressible, maintaining their volume even under pressure. The density of a liquid is usually close to th ...
with a
chloroform
Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...
-like
odour
An odor (American English) or odour (English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is a smell or a scent caused by one or more volatilized ...
. 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. It is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). Vinyl chloride is a ...
, which is used to make
polyvinyl chloride
Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of ...
(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
A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
. It forms
azeotrope
An azeotrope () or a constant heating point mixture is a mixture of two or more liquids whose proportions cannot be changed by simple distillation.Moore, Walter J. ''Physical Chemistry'', 3rd e Prentice-Hall 1962, pp. 140–142 This happens beca ...
s with many other
solvent
A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...
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 (), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas,
ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...
) and
chlorine
Chlorine is a chemical element; it has Symbol (chemistry), 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 ...
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. "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 (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...
,
Western Europe
Western Europe is the western region of Europe. The region's extent varies depending on context.
The concept of "the West" appeared in Europe in juxtaposition to "the East" and originally applied to the Western half of the ancient Mediterranean ...
, and
Japan
Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea ...
. 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
Copper(II) chloride, also known as cupric chloride, is an inorganic compound with the chemical formula . The monoclinic crystal system, monoclinic yellowish-brown anhydrous form slowly absorbs moisture to form the orthorhombic blue-green hydrate, ...
-catalysed
oxychlorination of ethylene:
: +
Uses
Vinyl chloride production
Approximately 95% of the world's production of 1,2-dichloroethane is used 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. It is an important industrial chemical chiefly used to produce the polymer polyvinyl chloride (PVC). Vinyl chloride is a ...
monomer
A monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or two- or three-dimensional network in a process called polymerization.
Classification
Chemis ...
(VCM) with
hydrogen chloride
The Chemical compound, compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hyd ...
as a byproduct. VCM is the precursor to
polyvinyl chloride
Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons of ...
.
:
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 this use has phased out 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, bacteria, bacterium, or plant, as well as the effect o ...
. As a useful 'building block' reagent, it is used as an intermediate in the production of diverse organic compounds such as
ethylenediamine
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately ...
and higher
ethyleneamines.
In the laboratory it is occasionally used as a source of
chlorine
Chlorine is a chemical element; it has Symbol (chemistry), 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 ...
, with elimination of ethene and chloride.
Via several steps, 1,2-dichloroethane is a precursor to
1,1,1-trichloroethane. Historically, before leaded petrol was phased out, chloroethanes were used as an additive in petrol to prevent lead buildup in engines.
Safety
1,2-Dichloroethane is highly
flammable
A combustible material is a material that can burn (i.e., sustain a flame) in air under certain conditions. A material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort ...
and releases
hydrochloric acid
Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...
when combusted:
: +
It is also
toxic
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 subst ...
(especially by inhalation due to its high
vapour pressure
Vapor pressure or equilibrium vapor pressure is the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phases (solid or liquid) at a given temperature in a closed system. The equilibrium vapor pressure is an indicat ...
) and possibly
carcinogen
A carcinogen () is any agent that promotes the development of cancer. Carcinogens can include synthetic chemicals, naturally occurring substances, physical agents such as ionizing and non-ionizing radiation, and biologic agents such as viruse ...
ic. Its high
solubility
In chemistry, solubility is the ability of a chemical substance, substance, the solute, to form a solution (chemistry), solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form su ...
and 50-year
half-life Half-life is a mathematical and scientific description of exponential or gradual decay.
Half-life, half life or halflife may also refer to:
Film
* Half-Life (film), ''Half-Life'' (film), a 2008 independent film by Jennifer Phang
* ''Half Life: ...
in
anoxic
Anoxia means a total depletion in the level of oxygen, an extreme form of hypoxia or "low oxygen". The terms anoxia and hypoxia are used in various contexts:
* Anoxic waters, sea water, fresh water or groundwater that are depleted of dissolved ox ...
aquifer
An aquifer is an underground layer of water-bearing material, consisting of permeability (Earth sciences), permeable or fractured rock, or of unconsolidated materials (gravel, sand, or silt). Aquifers vary greatly in their characteristics. The s ...
s 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 in mycoremediation, and plants in phytoremediation), living or dead, is employed for removing environmental pollutants from air, wate ...
. 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
China, officially the People's Republic of China (PRC), is a country in East Asia. With population of China, a population exceeding 1.4 billion, it is the list of countries by population (United Nations), second-most populous country after ...
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 with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water
Water is an inorganic compound with the c ...
are possible substitutes as solvents.
Dichloroethane is unstable in the presence of
aluminium
Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...
and, when moist, with
zinc
Zinc is a chemical element; it has symbol Zn and atomic number 30. It 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 periodic tabl ...
and
iron
Iron is a chemical element; it has symbol Fe () and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, forming much of Earth's o ...
.
References
External links
Gezelschap der Hollandsche ScheikundigenMerck 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-
IARC Group 2B carcinogens
Organochloride insecticides
Chloroalkanes
Plastics
Halogenated solvents
Fuel additives