1,2-Dichloroethane

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1,2-Dichloroethane
1,2-Dichloroethane 1,2-dichloroethane.svg
1,2-Dichloroethane
1,2-Dichloroethane 1,2-dichloroethane-3D-vdW.png
1,2-Dichloroethane
Names
Preferred IUPAC name
1,2-Dichloroethane
Other names
Ethylene dichloride
Ethylene chloride
1,2-DCA
1,2-DCE
DCE [1]
Ethane dichloride
Dutch liquid, Dutch oil
Freon 150
Identifiers
3D model (JSmol)
3DMet
605264
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.145 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-458-1
49272
KEGG
PubChem CID
RTECS number
  • KI0525000
UNII
  • InChI=1S/C2H4Cl2/c3-1-2-4/h1-2H2 Yes check.svgY
    Key: WSLDOOZREJYCGB-UHFFFAOYSA-N Yes check.svgY
  • ClCCCl
Properties
C2H4Cl2
Molar mass 98.95 g·mol−1
AppearanceColorless liquid
Odor characteristic, pleasant chloroform-like odor [2]
Density 1.253 g/cm3, liquid
Melting point −35 °C (−31 °F; 238 K)
Boiling point 84 °C (183 °F; 357 K)
0.87 g/100 mL (20 °C)
Viscosity 0.84  mPa·s at 20 °C
Structure
1.80  D
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic, flammable, carcinogenic
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H225, H302, H315, H319, H335, H350
P201, P202, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
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 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Flash point 13 °C (55 °F; 286 K)
Explosive limits 6.2–16% [2]
Lethal dose or concentration (LD, LC):
3000 ppm (guinea pig, 7  h)
1000 ppm (rat, 7 h) [3]
1217 ppm (mouse, 2 h)
1000 ppm (rat, 4 h)
3000 ppm (rabbit, 7 h) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 50 ppm C 100 ppm 200 ppm [5-minute maximum peak in any 3 hours] [2]
REL (Recommended)
Ca TWA 1 ppm (4 mg/m3) ST 2 ppm (8 mg/m3) [2]
IDLH (Immediate danger)
Ca [50 ppm] [2]
Related compounds
Related haloalkanes
Methyl chloride
Methylene chloride
1,1,1-Trichloroethane
Related compounds
 Ethylene
Chlorine
Vinyl chloride
Supplementary data page
1,2-Dichloroethane (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [4] 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 (at a boiling point of 70.5 °C or 158.9 °F or 343.6 K) and other chlorocarbons. [5]

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 (Dutch : Gezelschap der Hollandsche Scheikundigen), were the first to produce 1,2-dichloroethane from olefiant gas (oil-making gas, ethylene) and chlorine gas. [6] 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, Western Europe, and Japan. [7] Production is primarily achieved through the iron(III) chloride-catalysed reaction of ethylene and chlorine:

H2C=CH2 (g) + Cl2 (g) → ClC2H4Cl (l) (ΔH⊖r = −218 kJ/mol)

1,2-dichloroethane is also generated by the copper(II) chloride-catalysed oxychlorination of ethylene:

H2C=CH2 + 2 HCl + 1/2O2 → ClC2H4Cl + H2O

Uses

Vinyl chloride monomer (VCM) production

Approximately 95% of the world's production of 1,2-dichloroethane is used in the production of vinyl chloride monomer (VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride.

ClC2H4Cl → H2C=CHCl + HCl

The hydrogen chloride can be re-used in the production of more 1,2-dichloroethane via the oxychlorination route described above. [8]

Other uses

1,2-Dichloroethane has been used as degreaser and paint remover but is now banned from use due to its toxicity 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 and higher ethyleneamines. [9] In the laboratory it is occasionally used as a source of chlorine, 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. [10]

Safety

1,2-Dichloroethane is highly flammable [11] and releases hydrochloric acid when combusted:

ClC2H4Cl + 5/2O2 → 2 CO2 + H2O + 2 HCl

It is also toxic (especially by inhalation due to its high vapour pressure) and possibly carcinogenic. Its high solubility 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. [12] 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. [13] [14] Substitutes are recommended and will vary according to application. Dioxolane and toluene are possible substitutes as solvents. Dichloroethane is unstable in the presence of aluminium metal and, when moist, with zinc and iron.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Chlorine</span> Chemical element, symbol Cl and atomic number 17

Chlorine is a chemical element; it has 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 is a yellow-green gas at room temperature. It is an extremely reactive element and a strong oxidising agent: among the elements, it has the highest electron affinity and the third-highest electronegativity on the revised Pauling scale, behind only oxygen and fluorine.

The compound hydrogen chloride has the chemical formula HCl 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. Hydrogen chloride gas and hydrochloric acid are important in technology and industry. Hydrochloric acid, the aqueous solution of hydrogen chloride, is also commonly given the formula HCl.

<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", 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, sharp odor, detectable by most people at a concentration of 50 ppm.

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> Solvent, now banned for ozone depletion

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.

Iron(III) chloride describes the inorganic compounds with the formula FeCl3(H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated forms which are both hygroscopic. They feature iron in its +3 oxidation state. The anhydrous derivative is a Lewis acid, while all forms are mild oxidizing agents. It is used as a water cleaner and as an etchant for metals.

In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.

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

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds containing at least one covalently bonded atom of chlorine. The chloroalkane class includes common examples. The wide structural variety and divergent chemical properties of organochlorides lead to a broad range of names, applications, and properties. Organochlorine compounds have wide use in many applications, though some are of profound environmental concern, with TCDD being one of the most notorious.

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

Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

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

Sulfur dichloride is the chemical compound with the formula SCl2. This cherry-red liquid is the simplest sulfur chloride and one of the most common, and it is used as a precursor to organosulfur compounds. It is a highly corrosive and toxic substance, and it reacts on contact with water to form chlorine-containing acids.

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.

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.

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

Disulfur dichloride is the inorganic compound of sulfur and chlorine with the formula S2Cl2. It is an amber oily liquid.

<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.

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

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.

In chemistry, oxychlorination is a process for generating the equivalent of chlorine gas (Cl2) from hydrogen chloride and oxygen. This process is attractive industrially because hydrogen chloride is less expensive than chlorine.

References

  1. ↑ Staff writer. "Standard Abbreviations and Acronyms" (PDF). The Journal of Organic Chemistry. DCE: 1,2-dichloroethane
  2. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0271". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "Ethylene dichloride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ "Toxic Substances – 1,2-Dichloroethane". ATSDR. Retrieved 23 September 2015.
  5. ↑ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, Trevor Mann "Chlorinated Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry. 2006, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a06_233.pub2.
  6. ↑ Deimann, van Troostwyk, Bondt and Louwrenburgh (1795) "Ueber die Gasarten, welche man aus Verbindungen von starker Vitriolsäure und Alkohol erhält" (On the types of gases which one obtains from combinations of strong vitriolic acid and alcohol), Chemische Annalen ... , 2 : 195-205, 310-316, 430-440. The production and characterization of 1,2-dichloroethane appear on pages 200-202. The investigators were trying to detect the presence of carbon (Kohl) in ethylene (Luft, literally, "air") by adding chlorine (zündend Salzgas, literally, "burning gas from salt"). Instead of the expected soot, an oil (Oehl) formed.
  7. ↑ J.A. Field & R. Sierra-Alvarez (2004). "Biodegradability of chlorinated solvents and related chlorinated aliphatic compounds". Rev. Environ. Sci. Biotechnol. 3 (3): 185–254. doi:10.1007/s11157-004-4733-8. S2CID   36536985.
  8. ↑ "Ethylene Dichloride – Chemical Economics Handbook (CEH) – IHS Markit". ihs.com. Retrieved 8 April 2018.
  9. ↑ Srivasan Sridhar; Richard G. Carter (2001). "Diamines and Higher Amines, Aliphatic". Kirk-Othmer Encyclopedia of Chemical Technology. New York: John Wiley. doi:10.1002/0471238961.0409011303011820.a01.pub2. ISBN   9780471238966.
  10. ↑ Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics . 22 (25): 5154–5178. doi:10.1021/om030621b.
  11. ↑ "1,2-Dichoroethane MSDS." Mallinckrodt Chemicals. 19 May 2008. Web. <http://hazard.com/msds/mf/baker/baker/files/d2440.htm>.
  12. ↑ S. De Wildeman & W. Verstraete (25 March 2003). "The quest for microbial reductive dechlorination of C2 to C4 chloroalkanes is warranted". Appl. Microbiol. Biotechnol. 61 (2): 94–102. doi:10.1007/s00253-002-1174-6. PMID   12655450. S2CID   72921.
  13. ↑ "Toxic Christmas: Plastic Ornaments May Pollute Your Air". rodale.com. Archived from the original on 18 March 2012. Retrieved 8 April 2018.
  14. ↑ Doucette, WJ; Hall, AJ & Gorder, KA (Winter 2010). "Emissions of 1, 2-Dichloroethane from Holiday Decorations as a Source of Indoor Air Contamination". Ground Water Monitoring & Remediation. 30 (1): 67–73. CiteSeerX   10.1.1.1013.1487 . doi:10.1111/j.1745-6592.2009.01267.x. S2CID   96563330.
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