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1,2-dichloroethane

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1,2-dichloroethane
Name1,2-dichloroethane
Othernamesethylene dichloride; EDC
FormulaC2H4Cl2
Molar mass98.96 g·mol−1
Density1.253 g·cm−3 (20 °C)
Melting point−35.7 °C
Boiling point83.5 °C
Solubility8 g·L−1 (20 °C)

1,2-dichloroethane is a colorless, oily liquid historically produced and traded worldwide as a key organic compound intermediate and solvent used in large-scale chemical industry processes. It is industrially significant as a precursor to vinyl chloride, with production, transport, and use subject to multinational regulation and workplace occupational safety frameworks. Due to its volatility, persistence under some conditions, and health effects, it is closely monitored by agencies and appears in environmental assessments linked to major industrial accidents and remediation programs.

Chemical properties

1,2-dichloroethane is a saturated halocarbon with a vicinal dichloro substitution on an ethane backbone; its molecular structure yields modest polarity and a refractive index useful in physical property characterization by techniques employed at institutions like National Institute of Standards and Technology and laboratories supporting United States Environmental Protection Agency methods. The compound exhibits moderate solubility in water, a high density relative to water, and a vapor pressure that governs behavior in atmospheric transport studied in collaborations involving NASA and environmental observatories such as European Space Agency-supported monitoring networks. Thermochemical data including enthalpy and Gibbs energy are reported in compilations by bodies such as the International Union of Pure and Applied Chemistry and are used in process design by firms like BASF and Dow Chemical Company.

Production and synthesis

Industrial production historically relied on chlorination of ethylene in the presence of catalysts and radical initiators, a route developed in early 20th‑century chemical manufacture alongside processes refined by companies such as Union Carbide and later implemented by multinational corporations including Shell plc and ExxonMobil. Alternative synthesis routes include hydrochlorination of acetylene under conditions investigated by academic groups at universities like Massachusetts Institute of Technology and Imperial College London and oxychlorination processes that recycle chlorine in integrated plants operated by conglomerates such as DuPont. Large petrochemical complexes in regions like the Gulf Coast (United States) and Rhineland historically shaped global trade flows, with feedstock supply chains tied to producers such as Saudi Aramco and Rosneft.

Applications and uses

Major use is as a feedstock for production of vinyl chloride monomer and subsequently polyvinyl chloride, a chain of manufacture central to manufacturers such as Ineos and Formosa Plastics, supplying products for sectors represented by corporations like Toyota and Siemens. It has been employed as a solvent in degreasing and extraction operations in facilities run by firms including General Electric and Boeing, and in formulations for pharmaceutical intermediate manufacture at companies such as Pfizer and Roche. Historically, it served as a fumigant and component of refrigerant blends inspected by agencies like the World Health Organization and regulated under international agreements similar in impact to the Stockholm Convention and Basel Convention on hazardous chemicals.

Environmental fate and toxicity

Environmental behavior includes volatilization, limited aqueous hydrolysis, and biodegradation pathways studied by researchers affiliated with University of California, Berkeley, ETH Zurich, and national laboratories including Lawrence Berkeley National Laboratory. It is classified by many regulators as a probable human carcinogen based on toxicological evaluations by bodies such as the International Agency for Research on Cancer and has been the subject of epidemiological study in cohorts overseen by institutions like Centers for Disease Control and Prevention and National Institutes of Health. Contamination at industrial sites has led to remediation actions guided by frameworks from the United States Environmental Protection Agency and the European Environment Agency, with plume dynamics modeled using software developed in collaboration with agencies like USGS.

Occupational safety and regulation

Occupational exposure limits and controls are promulgated by agencies such as Occupational Safety and Health Administration and European Chemicals Agency, with recommended exposure limits informed by research from centers including Harvard T.H. Chan School of Public Health and Johns Hopkins Bloomberg School of Public Health. Personal protective equipment, engineering controls, and emergency response procedures are specified in standards set by National Fire Protection Association and adhered to in industrial sites operated by corporations like Chevron and BP. International trade and transport are regulated under instruments administered by organizations such as the International Maritime Organization and International Labour Organization.

Analytical detection and monitoring

Detection in air, water, and soil typically employs headspace gas chromatography coupled with mass spectrometry, techniques standardized in methods from laboratories like National Institute for Occupational Safety and Health and validated by collaborative studies involving European Commission reference laboratories. Environmental monitoring programs run by Environment Canada, Australian Department of Agriculture, Water and the Environment, and municipal agencies in cities like London and New York City integrate ambient sampling with analytical protocols accredited against standards from International Organization for Standardization. Biomonitoring for occupational health uses blood and breath analysis with platforms developed in academic centers including Karolinska Institutet and University of Toronto.

Category:Chloroalkanes