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Trans-1,2-Dichloroethylene, often abbreviated as trans-1,2-DCE or (E)-1,2-Dichloroethene, is a volatile, colorless organic compound with the chemical formula C₂H₂Cl₂.
Trans-1,2-Dichloroethylene is one of the two geometric isomers of 1,2-dichloroethylene, the other being the cis form, and is characterized by the chlorine atoms being positioned on opposite sides of the carbon-carbon double bond, which gives it distinct physical and chemical properties compared to the cis isomer.
Trans-1,2-Dichloroethylene has a sweet, chloroform-like odor, is moderately soluble in water, and is highly soluble in most organic solvents such as alcohols, ethers, and hydrocarbons.
CAS Number: 156-60-5
Molecular Formula: C2H2Cl2
Molecular Weight: 96.94
EINECS Number: 205-860-2
Synonyms: TRANS-1,2-DICHLOROETHYLENE, 156-60-5, trans-1,2-Dichloroethene, (E)-1,2-Dichloroethylene, 1,2-trans-Dichloroethylene, Ethene, 1,2-dichloro-, (1E)-, trans-Acetylene dichloride, Ethene, 1,2-dichloro-, (E)-, RCRA waste number U079, Ethylene, 1,2-dichloro-, (E)-, HCC 1130t, Ethylene, 1,2-dichloro-, trans-, R 1130t, NSC 60512, trans-1,2-DCE, CCRIS 2505, Dichloroethylene, trans-, HSDB 6361, 1,2-trans-Dichloroethene, 1,trans-2-Dichloroethene, EINECS 205-860-2, trans-Dichloroethene, trans-Di-1,2-Chloroethylene, BRN 1420761, Dichloroethylene-trans, CHEBI:29027, AI3-28786, (E)-CHCl=CHCl, 1,2-Dichloroethylene (trans), EC 205-860-2, 4-01-00-00709 (Beilstein Handbook Reference), transDichloroethylene, Ethene,1,2-dichloro, trans1,2Dichloroethene, (E)1,2Dichloroethene, 1,2-dichloro ethylene, 1,2transDichloroethylene, (E)1,2Dichloroethylene, RefChem:196314, 1,2Dichloroethene, trans, trans-1, 2-Dichloroethene, Ethene, 1,2dichloro, (E), Ethylene, 1,2dichloro, trans, trans-Di-1, 2-chloroethylene, Ethylene, 1,2dichloro, (E), Ethene, 1,2dichloro, (1E), cis or trans 1,2-Dichloroethene, 1,2-DICHLOROETHYLENE, (1E)-, Ethene, 1,2-dichloro-, (E)-(9CI), KFUSEUYYWQURPO-OWOJBTEDSA-N, (E)-1,2-Dichloroethene, trans-Dichloroethylene, 1,2-Dichloroethene, trans-, DTXSID7024031, MFCD00062942, 1,2-Dichloroethylene, mixture of cis and trans, (E)-1,2-Dichloroethene (stabilized with MEHQ), NSC-60512, 41799BI61U, C2H2Cl2, DTXCID704031, 1,2-Dichloroethylene, all isomers, CAS-156-60-5, RCRA waste no. U079, UNII-41799BI61U, 1,2-Dichloraethen, 15075-90-8, E-1,2-dichloroethene, Acetylene dichloride, trans-, SCHEMBL27927, WLN: G1U1G-T, (1E)-1,2-dichloroethylene, Ethene,2-dichloro-, (E)-, trans-1,2-Dichloroethene 100 microg/mL in Methanol, CHEMBL157026, Ethylene,2-dichloro-, (E)-, HCC-1130T, trans-1,2-Dichloroethylene, 98%, trans-1,2-Dichloroethylene, 99%, NSC60512, Tox21_200774, Tox21_202419, Tox21_303130, 1,2-DICHLOROETHYLENE, TRANS-, AKOS009031507, FD34631, R-1130T, NCGC00091531-02, NCGC00091531-03, NCGC00091531-04, NCGC00256973-01, NCGC00258328-01, NCGC00259968-01, CAS-540-59-0, ACETYLENE DICHLORIDE TRANS-FORM [MI], CS-0013984, D0368, NS00079504, EN300-19376, trans-1,2-Dichloroethene, analytical standard, C06791, EN300-366376, H11307, trans-1,2-Dichloroethylene, analytical standard, Q24716723, 1,2-DICHLOROETHYLENE;TRANS-SYM-ACETYLENEDICHLORIDE;TRANS-ACETYLENE DICHLORIDE;TRANS-1,2-DICHLOROETHENE;TRANS-1,2-DICHLOROETHYLENE;2-dichloro-(e)-ethylen;Acetylene dichloride, trans-;Dichloroethylene, trans-
Trans-1,2-Dichloroethylene exists in three isomers, sym-, cis-60% and trans-40%.
There are variations in toxicity between these two forms.
At room temperature, these chemicals are colorless liquids with a slightly acrid, ethereal odor.
Trans-1,2-Dichloroethylenes boiling point is relatively low, around 48–50°C, making it a volatile liquid at room temperature.
Trans-1,2-Dichloroethylene or 1,2-DCE is the name for a pair of organochlorine compounds with the molecular formula C2H2Cl2.
The two compounds are isomers, each being colorless liquids with a sweet odor.
Trans-1,2-Dichloroethylene can exist as either of two geometric isomers, cis-1,2-dichloroethene or trans-1,2-dichloroethene, but is often used as a mixture of the two.
They have modest solubility in water.
These compounds have some applications as a degreasing solvent.
In contrast to most cis-trans compounds, the Z isomer (cis) is more stable than the E isomer (trans) by 0.4 kcal/mol.
Trans-1,2-Dichloroethylene is classified as a halogenated alkene, meaning it contains a carbon-carbon double bond with halogen substitutions.
This structure makes it reactive in addition reactions, such as hydrogenation, halogenation, and polymerization, while being more stable than the cis isomer due to lower steric strain.
Trans-1,2-Dichloroethylenes stability and volatility allow it to act as a useful intermediate in chemical synthesis, particularly in the production of solvents, adhesives, coatings, and specialty polymers.
Trans-1,2-Dichloroethylene is often obtained as a purified isomer from industrial mixtures, which typically contain both cis and trans forms, and it is also commercially supplied stabilized with small amounts of inhibitors to prevent unwanted polymerization or decomposition during storage.
These compounds have "moderate oral toxicity to rats".
The dichloroethylene isomers occur in some polluted waters and soils, as the decomposition products of trichloroethylene.
Significant attention has been paid to their further degradation, e.g. by iron particles.
From an industrial perspective, Trans-1,2-Dichloroethylene is used as a solvent and chemical intermediate, valued for its ability to dissolve a wide variety of organic materials and participate in controlled chemical reactions.
Trans-1,2-Dichloroethylenes non-flammability under normal conditions and moderate chemical reactivity make it suitable for certain cleaning, degreasing, and extraction processes, although proper handling precautions are required due to its toxicity and environmental persistence.
Additionally, because it is a volatile organic compound (VOC), it readily evaporates into the atmosphere, where it can participate in photochemical reactions contributing to air pollution if released in large quantities.
Trans-1,2-Dichloroethylene is a versatile halogenated solvent and chemical intermediate that combines moderate chemical reactivity, volatility, and solubility in organic solvents, making it valuable in industrial and laboratory applications.
Its geometric configuration, physical properties, and chemical stability distinguish it from its cis isomer, while its toxicity and environmental considerations require careful storage, handling, and disposal.
Melting point: −57 °C(lit.)
Boiling point: 48-60 °C(lit.)
Density: 1.257 g/mL at 25 °C(lit.)
Vapor pressure: 5.32 psi (20 °C)
Refractive index: n20/D 1.447(lit.)
Flash point: 43 °F
Storage temp.: Refrigerator
Solubility: Miscible with acetone, ethanol, and ether and very soluble in benzene and chloroform (U.S. EPA, 1985)
Form: Liquid
Color: Clear colorless
Explosive limit: 12.8%
Water Solubility: Miscible with ethanol, ethyl ether, acetone, benzene and chloroform. Immiscible with water.
Merck: 14,92
BRN: 1420761
Henry's Law Constant: 10.12 at 30 °C (headspace-GC, Sanz et al., 1997)
Exposure limits: OSHA PEL: TWA 200 ppm (790 mg/m3); ACGIH TLV: TWA 200 ppm (adopted).
Dielectric constant: 2.27
Stability: Incompatible with oxidizing agents, bases. Stable, but may decompose on exposure to air, moisture or light. Highly flammable.
EPA Primary Drinking Water Standard: MCL:0.1, MCLG:0.1
LogP: 2.06
Trans-1,2-Dichloroethylene is a member of chloroethenes.
Trans-1,2-Dichloroethylene, the Z isomer, is obtainable by the controlled chlorination of acetylene: C2H2 + Cl2 → C2H2Cl2
Industrially both isomers arise as byproducts of the production of vinyl chloride, which is produced on a vast scale.
Unlike Trans-1,2-Dichloroethylene, the 1,2-dichloroethylene isomers do not polymerize.
Trans-1,2-Dichloroethylene has applications including electronics cleaning, precision cleaning, and certain metal cleaning applications.
Both isomers participate in Kumada coupling reactions.
Trans-1,2-Dichloroethylene participates in cycloaddition reactions.
Trans-1,2-Dichloroethylene reacts with alkalis, difluoromethylene, dihypofluorite, and nitrogen tetraoxide.
Contact with solid alkalis or their concentrated solutions will cause formation of chloroacetylene, which ignites in air.
Avoid contact with copper and copper alloys corrosive to metals unless an inhibitor has been added.
Oxidation in the presence of concentrated sulfuric acid or a free radical initiator gives chloroacetyl chloride via epoxide intermediates.
Trans-1,2-Dichloroethylene incompatible with organic peroxides.
In a methanogenic aquifer material, Trans-1,2-Dichloroethylene biodegraded to vinyl chloride.
Under anoxic conditions Trans-1,2-Dichloroethylene, when subjected to indigenous microbes in uncontaminated sediments, degraded to vinyl chloride.
Trans-1,2-Dichloroethylene showed slow to moderate degradation concomitant with the rate of volatilization in a static-culture flask-screening test (settled domestic wastewater inoculum) conducted at 25 °C.
At concentrations of 5 and 10 mg/L, percent losses after 4 wk of incubation were 95 and 93, respectively.
The amount lost due to volatilization was 26 to 33% after 10 d.
Trans-1,2-Dichloroethylene is a colorless liquid, with a sharp, harsh odor, and is highly flammable.
The primary uses for trans-1,2-dichloroethylene are as a solvent in processing and in formulations for cleaning and degreasing.
Trans-1,2-Dichloroethylene is a halogenated hydrocarbon and specifically a monochlorinated alkene derivative in which two chlorine atoms are attached to adjacent carbon atoms of a carbon-carbon double bond, but located on opposite sides, giving it the E (entgegen) geometric configuration.
This trans configuration reduces steric hindrance compared to its cis counterpart, resulting in slightly higher melting and boiling points and greater thermodynamic stability.
Trans-1,2-Dichloroethylenes chemical formula, C₂H₂Cl₂, and molecular weight of approximately 96.94 g/mol reflect its small, volatile, and reactive nature, which contributes to both its industrial usefulness and potential environmental and health hazards.
Physically, Trans-1,2-Dichloroethylene is a clear, colorless liquid with a mild, sweet, and chloroform-like odor, making it easily identifiable in laboratory and industrial settings.
Trans-1,2-Dichloroethylene has a low viscosity and low surface tension, which allows it to penetrate and dissolve a wide range of organic and some inorganic compounds, particularly oils, greases, waxes, and certain resins.
This solubility, combined with its moderate volatility, makes it particularly useful as a solvent for cleaning, degreasing, and extraction applications, where rapid evaporation without leaving residues is advantageous.
Trans-1,2-Dichloroethylene participates in electrophilic addition reactions due to its carbon-carbon double bond, including hydrogenation to ethylene dichloride derivatives, halogenation, hydrohalogenation, and polymerization reactions.
Its reactivity is slightly less than the cis isomer, which can be beneficial in industrial processes requiring controlled reactivity without rapid degradation.
Additionally, Trans-1,2-Dichloroethylene can act as a starting material or intermediate in the production of vinyl chloride, specialty plastics, adhesives, coatings, and other halogenated organic compounds.
From an environmental perspective, trans-1,2-Dichloroethylene is moderately persistent in water and soil and has low biodegradability, making accidental release a potential concern.
Its volatility contributes to its movement into the atmosphere, where it can participate in photochemical reactions leading to ground-level ozone formation, a consideration for regulatory controls on volatile organic compounds (VOCs).
trans-1,2-Dichloroethylene is a chemically versatile, industrially important halogenated alkene.
Its combination of solvent properties, moderate reactivity, stability relative to the cis isomer, and volatility makes it a widely used chemical in manufacturing, laboratory, and specialty chemical applications.
However, its toxicological profile, environmental persistence, and volatility require strict attention to safe handling, storage, and disposal practices.
Uses:
Trans-1,2-Dichloroethylene is used in the preparation of solvents and in chemical mixtures.
Trans-1,2-Dichloroethylene also acts as a synthetic agent and active constituent of perfumes.
Further, it is used for electronics cleaning, precision cleaning and metal cleaning activities.
Trans-1,2-Dichloroethylene may be used as an analytical reference standard for the determination of the analyte in water samples by gas chromatography (GC) based analytical techniques.
Solvent for fats, phenol, camphor, etc. Intermediate in synthesis of chlorinated solvents and compounds.
Trans-1,2-Dichloroethylene is widely used as a solvent in industrial processes due to its ability to dissolve a variety of organic materials, including oils, greases, waxes, and certain polymers.
Its low viscosity and rapid evaporation rate make it particularly suitable for cleaning, degreasing, and extraction applications, where residual-free drying is essential.
For example, Trans-1,2-Dichloroethylene is often employed in metal cleaning operations, precision instrument maintenance, and degreasing of machinery parts in automotive and electronics industries, where its volatility ensures that surfaces dry quickly without leaving a residue.
Trans-1,2-Dichloroethylene serves as a key intermediate in the production of various organic chemicals.
Trans-1,2-Dichloroethylene participates in electrophilic addition reactions and can be used to synthesize compounds such as vinyl chloride, which is a precursor for polyvinyl chloride (PVC) plastics.
Additionally, it is involved in the manufacture of specialty polymers, adhesives, coatings, and other halogenated compounds where controlled chlorination or halogenation is required.
Its reactivity combined with moderate stability allows chemists to carry out targeted transformations with predictable yields, making it a valuable reagent in industrial chemistry.
In laboratory settings, trans-1,2-Dichloroethylene is used as a solvent for analytical and research purposes, particularly in organic chemistry experiments.
Trans-1,2-Dichloroethylenes chemical properties allow it to dissolve poorly soluble compounds that cannot be effectively processed with water or less polar solvents.
Trans-1,2-Dichloroethylene is also used in chromatography, spectroscopy, and other analytical techniques where a clean, volatile organic solvent is required for sample preparation, extraction, or purification.
Due to its solvent properties and controlled reactivity, trans-1,2-Dichloroethylene is employed in precision cleaning applications in industries such as electronics, optics, and aerospace, where delicate components must be cleaned without leaving residues or causing corrosion.
Its low surface tension and rapid evaporation allow it to reach small crevices and complex geometries, ensuring thorough cleaning of intricate machinery and electronic assemblies.
Trans-1,2-Dichloroethylene is sometimes sold stabilized with inhibitors such as hydroquinone or MEHQ to prevent polymerization during storage and transport.
In this form, it is suitable as a feedstock for chemical manufacturing, where stable supply of the E-isomer is necessary for precise reactions in producing halogenated polymers, chlorinated solvents, and specialty chemicals.
Its moderate polarity and solvency make trans-1,2-Dichloroethylene useful in the formulation of coatings, paints, and extraction solvents.
In chemical processes where selective solubility is needed, it acts as a medium to dissolve organic compounds, resins, or oils without initiating unwanted reactions, allowing manufacturers to control reaction conditions or achieve uniform coatings on surfaces.
Safety Profile:
Moderately toxic by ingestion middly toxic by inhalation.
Human systemic effects by inhalation: sleep, hallucinations, and distorted perceptions.
Experimental reproductive effects, a skin and eye irritant.
Mutation data reported exposure to high vapor concentration can cause nausea, vomiting, weakness, tremor, and cramps.
Recovery is usually prompt following removal from exposure dermatitis may result from defatting action on skin.
Dangerous fire hazard when exposed to heat, flame, or oxidtzers.
Moderate explosion hazard in the form of vapor when exposed to flame. Violent reaction with difluoromethylene dihypofluorite.
Forms shock-sensitive explosive mixtures with dinitrogen tetraoxide reaction with solid caustic alkahes or their concentrated solutions produces chloracetylene gas that ignites spontaneously in air. Reacts violently with N2O4, KOH, Na, NaOH.
Moderate explosion hazard in the form of vapor when exposed to flame. Can react vigorously with oxidizing materials to fight fire, use water spray, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-.
Trans-1,2-Dichloroethylene is a toxic and volatile organic compound, and exposure can occur via inhalation, ingestion, or direct contact with the skin and eyes.
Inhalation of vapors can irritate the respiratory tract, causing symptoms such as coughing, throat irritation, dizziness, headache, nausea, and in high concentrations, central nervous system depression.
Chronic or prolonged inhalation may lead to more severe neurological effects, including fatigue, impaired coordination, and confusion.
Accidental ingestion can result in gastrointestinal distress, abdominal pain, and vomiting, and may pose systemic toxicity risks if sufficient quantities are consumed.
Skin contact may lead to mild irritation or dermatitis, while eye contact can cause pain, redness, and temporary irritation.
Trans-1,2-Dichloroethylene is highly flammable and can form explosive mixtures with air.
Its flash point is relatively low, and it can ignite if exposed to open flames, sparks, or high temperatures.
In the event of fire, decomposition can produce toxic gases, including hydrogen chloride, phosgene, and carbon monoxide, which are highly dangerous if inhaled.
Proper fire suppression techniques, such as using dry chemical extinguishers, carbon dioxide, or foam, are necessary, and exposure to smoke and fumes should be avoided.
