1,2-ジクロロエチレン

1,2-Dichloroethylene

HCID 10900CAS 540-59-0

基本情報

標準SMILES
ClC=CCl
InChIKey
KFUSEUYYWQURPO-UHFFFAOYSA-N
分子式
C2H2Cl2
平均分子量
96.94 g/mol
単同位体質量
95.95335542

概要

1, 2-Dichloroethene, also called 1, 2-dichloroethylene, is a highly flammable, colorless liquid with a sharp, harsh odor. It is used to produce solvents and in chemical mixtures. You can smell very small amounts of 1, 2-dichloroethene in air (about 17 parts of 1, 2-dichloroethene per million parts of air [17 ppm]). There are two forms of 1, 2-dichloroethene; one is called cis-1, 2-dichloroethene and the other is called trans-1,2-di-chloroethene. Sometimes both forms are present as a mixture.

名称と識別子

優先名称
1,2-Dichloroethylene
IUPAC
1,2-dichloroethene
現地名
1,2-ジクロロエチレン
英語名
1,2-Dichloroethylene
分子式
C2H2Cl2
分子量
96.94

名称と別名

1,2-Dichloroethylene1,2-Dichloroethene540-59-0Ethene, 1,2-dichloro-DioformAcetylene dichloridesym-Dichloroethylene1,2-Dichlor-aethenDichloro-1,2-ethyleneDTXSID8024991Ethylene, 1,2-dichloro-NCI-C56031
名称をさらに表示
1,2-ジクロロエチレン二塩化アセチレン1,2ジクロロエチレン1,2-ジクロロエチレン(unspecified isomers)ジクロロエチレン(Z)-1,2-DichloroetheneDichloroethyleneDichloroethylenesResidual Solvent Class 2 - 1,2-DichloroetheneDichloracetylene1,2-DICHLORETHENE
XU9RUA6YUTDTXCID304991CHEBI:18882RefChem:718651,2-DICHLOROETHYLENE (MIXED ISOMERS)208-750-21,2-DICHLOROETHYLENE, (MIXED ISOMERS)1,2-DICHLOROETHYLENE (MIXTURE OF CIS AND TRANS)

データベース識別子

CAS
540-59-0
PubChem CID
10900
DTXSID
DTXSID8024991
ChEMBL
CHEMBL1385560
EC Number
208-750-2

物性

構造計算による物性

XLogP
1.9
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
4

実験および物理化学的性質

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Chlorinated Aliphatics
SpringerMaterials PropertiesCorrosion
LogP · 2 件

log Kow = 1.86

2

Odor · 4 件

Ethereal, slightly acrid

Pleasant

Sweet, slightly irritating chloroform-like odor

... Slightly acrid, chloroform-like odor

Density · 6 件

1.27 at 77 °F (USCG, 1999) - Denser than water; will sink

Approximately 1.28

Relative density (water = 1): 1.28

1.27

~1.28 No temp

(77 °F): 1.27

物理化学的性質

融点
57 °C · −57 °C(lit.)
沸点
48 · 48-60 °C(lit.)
比重(密度)
1.265 g/mL · 1.265 g/mL at 25 °C(lit.)
蒸気圧
5.32 psi · 5.32 psi ( 20 °C)
屈折率
20 · n20/D 1.447(lit.)
闪点
43 °F · 43 °F
化学的性質 · 1 件

化学的特性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. The Odor Threshold in air is 17 ppm. sym-isomer:

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 4 件

Chemical: Ethene, 1,2-dichloro-

Ethene, 1,2-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethene, 1,2-dichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

1,2-Dichloroethylene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelFlammable Liquid
Fire Hazards · 3 件

Special Hazards of Combustion Products: Phosgene and hydrogen chloride fumes may form in fires.

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire Potential · 2 件

Flammable liquid.

Highly flammable ... .

Health Hazards · 2 件

Inhalation causes nausea, vomiting, weakness, tremor, epigastric cramps, central nervous depression. Contact with liquid causes irritation of eyes and (on prolonged contact) skin. Ingestion causes slight depression to deep narcosis. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 2 件

1, 2-Dichloroethene, also called 1, 2-dichloroethylene, is a highly flammable, colorless liquid with a sharp, harsh odor. It is used to produce solvents and in chemical mixtures. You can smell very small amounts of 1, 2-dichloroethene in air (about 17 parts of 1, 2-dichloroethene per million parts of air [17 ppm]). There are two forms of 1, 2-dichloroethene; one is called cis-1, 2-dichloroethene and the other is called trans-1,2-di-chloroethene. Sometimes both forms are present as a mixture.

Liver injury observed in acute animal toxicology studies; [ACGIH] A skin, eye, and respiratory tract irritant; Inhalation of high concentrations may cause CNS effects; [ICSC]1,2-Dichloroethylene (UN1150) has warning of explosive polymerization; [ERG 2016] See trans-1,2-Dichloroethylene and cis-1,2-Dichloroethylene.

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents Not to Be Used: Water may be ineffective.

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Well closed. See Chemical Dangers.
Firefighting HazardsVapors are heavier than air and may travel to a source of ignition and flash back. ... Closed containers may rupture violently when heated.

毒性情報

Toxicological InformationCDC-ATSDR Toxicological Profile
Treatment · 1 件

Following inhalation exposure, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of seizures, administer a benzodiazepine IV. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes in case of eye exposure. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (T36)

Interactions · 1 件

Inhalation studies were conducted to determine the potential subchronic toxicity of a mixture of trans-1,2-dichloroethylene (70%), cis-1,2-dichloroethylene (5%), and perfluorobutylethylene (25%). Groups of rats were exposed to 0, 400, 2000, or 8000 ppm concentrations of the mixture vapor 6 hr/day, 5 days/wk, for a total of 20 exposures. Subgroups of rats were further observed during a 1-month recovery period. Functional observational battery (FOB) and motor activity (MA) behavioral tests were conducted prior to initiation of the exposures, during exposure wk 4, and after a 1-month post-exposure recovery period. Clinical pathology evaluations were conducted at the end of the exposure period and after a 1-month recovery period. At the end of the 4-wk exposure period, tissues from rats were collected, histologically processed, and evaluated by light microscopy. Test substance-related, biologically significant decreased body weights and body weight gains occurred in male and female rats exposed to 8000 ppm. In addition, test substance-related, statistically significant decreases in food consumption and/or food efficiency were observed in male rats exposed to 8000 ppm. During exposures to 8000 ppm, some rats exhibited tremors and ataxia. Usually tremors and ataxia were observed within 1 hr after initiation of the daily exposure period and were observed during each exposure day. Tremors were also observed during 1 exposure day in the 2000 ppm animals. In addition to the tremors and ataxia, rats exposed to 2000 ppm or 8000 ppm had a diminished and/or no alerting response to a sharp, sound stimulus during each of the daily exposure periods. These effects were transient since no clinical observations of compromised neurological function were detected when the rats were evaluated upon return to the animal room following exposure. Daily reoccurrence of this apparently acute effect in the 8000 ppm group did not produce enduring neurological changes since there were no test substance-related effects on FOB parameters or on MA conducted the day following the last exposure or during the recovery period. In addition, there were no toxicologically significant changes in hematology, clinical chemistry, or urinalysis parameters in either males or females for any exposure concentration; and there were no test substance-related gross or microscopic morphological changes in males or females administered any exposure concentration. Under the conditions of the study, the no-observed-effect level (NOEL) was 400 ppm in males and females based on clinical signs of toxicity during exposure to 2000 or 8000 ppm. /Mixture of trans-1,2-dichloroethylene (70%), cis-1,2-dichloroethylene (5%), and perfluorobutylethylene (25%)/

Target Organs · 2 件

Dermal (Skin), Immunological (Immune System), Ocular (Eyes)

Eyes, respiratory system, central nervous system

Health Effects · 1 件

Breathing trans-1,2-DCE can cause sever liver and kidney damages, pulmonary capillary hyperemia, as well as alveolar septal distention; depression of the central nervous sustem can occur; moderate iritis and conjunctivitis can follow eye exposure; dermatitis and irritation of mucous membranes can follow dermal exposure. Symptoms associated with lethal oral doses included decreased activity, ataxia, suppressed or total loss of righting reflex, and depressed respiration. (L585)

Ecotoxicity Values · 3 件

LC50; Species: Lepomis macrochirus (Bluegill) Young of Year, weight 0.32-1.2 g; Conditions: freshwater, static, 21-23 °C, pH 6.5-7.9, hardness 32-48 mg/L CaCO3, alkalinity 28-34 mg/L CaCO3, conductivity 93-190 umhos/cm, dissolved oxygen 0.3-9.7 mg/L; Concentration: 165000 uM for 24 hr /> or = 80% purity/

LC50; Species: Lepomis macrochirus (Bluegill) Young of Year, weight 0.32-1.2 g; Conditions: freshwater, static, 21-23 °C, pH 6.5-7.9, hardness 32-48 mg/L CaCO3, alkalinity 28-34 mg/L CaCO3, conductivity 93-190 umhos/cm, dissolved oxygen 0.3-9.7 mg/L; Concentration: 140000 ug/L for 96 hr (95% confidence interval: 120000-160000 ug/L) /> or = 80% purity/

LC50; Species: Eisenia fetida (Earthworm) adult, weight 300-500 mg; dermal 286 ug/sq cm for 48 hr (95% confidence interval: 264-308 ug/sq cm) /> or =98% purity/

法規制情報

FDA Requirements1,2-Dichloroethylene (mixed isomers) is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 1 件

U079; As stipulated in 40 CFR 261.33, when trans-1,2-dichloroethylene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). /Trans-1,2-Dichloroethylene/

TSCA Requirements · 2 件

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 3/11/94; Reporting date: 5/10/94.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Dichloroethylene is included on this list. Effective date: 3/11/94; Sunset date: 6/30/98.

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b). /trans-1,2-Dichloroethylene/

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations.
State Drinking Water Standards(FL) FLORIDA 70 ug/L

安全データ

OEB
A
OEL
TWA: 200 ppm (790 mg/m3)
wgk
2
IDLA
1,000 ppm
tsca
TSCA listed
rtecs
KV9360000

化学と産業

薬理情報

Metabolism/Metabolites · 5 件

Numerous xenobiotics are known to be bioactivated and to covalently bind to proteins, but the resulting amino acid adducts are unknown. In this study, the amino acid adducts of 12 (14)C-labeled aliphatic halides were examined after formation in an in vitro rat hepatic microsomal system. After exhaustive solvent extraction of the polypeptide microsomal protein, the amino acid adducts were isolated by Pronase digestion, followed by filtration through a 500 mol-wt exclusion membrane. 1,2-Dichloroethylene had a single major amino acid adduct. ...

1,2-Dichloroethene is metabolized in the liver, by hepatic microsomal cytochrome P-450, to form dichloroethanol and dichloroacetic acid.

Incubation of rat liver microsomes with 1,2-dichloroethylene caused a fall in microsomal cytochrome p450 content (as determined by measuring the oxidation of reduced nicotinamide adenine dinucleotide at 340 nm), without affecting other microsomal enzymes. The decrease in cytochrome p450 occurred only in the presence of reduced nicotinamide adenine dinucleotide, suggesting that the dichloroethylene must be metabolized to exert its destructive action. The loss of cytochrome p450 was probably due to destruction of heme, since the fall in cytochrome p450 was always accompanied by a parallel decrease in microsomal heme content.

Metabolism of 1,2-DCE is initially catalyzed by hepatic CYP450 ... . Studies suggest that the metabolism of 1,2-DCE involves epoxidation of the ethylene double-bond, forming dichlorinated epoxides, which can undergo a nonenzymatic rearrangement and produce several metabolites. Following rearrangement of the intermediate epoxide, reduction of the resulting dichloroacetaldehyde to dichloroethanol may be catalyzed by alcohol dehydrogenase (ADH). Studies ... provide evidence that dichloroacetaldehyde is the predominant metabolite of CYP450, which is extensively converted to dichloroethanol and dichloroacetate by dehydrogenases present in hepatocytes. Oxidative dechlorination of the minor metabolite, dichloroacetic acid (DCA), to glyoxylate is catalyzed by glutathione S-transferase zeta (GSTZ).

Metabolism of trans-1,2-dichloroethene is initially catalyzed by hepatic microsomal cytochrome P-450. This metabolism is believed to involve epoxidation of the ethylene double bond, forming dichlorinated epoxides. Dichlorinated epoxides, in turn, can undergo a non-enzymatic rearrangement. Studies on the metabolism of 1,2-dichloroethene by hepatic microsomes and hepatocytes provide evidence to suggest that dichloroacetaldehyde is the predominant metabolite of microsomal cytochrome P-450 and that it, in turn, is extensively converted to dichloroethanol and dichloroacetate by cytosolic and/or mitochondrial aldehyde and alcohol dehydrogenases present in hepatocytes. (L585)

Absorption, Distribution and Excretion · 2 件

1,2-Dichloroethene appears to be absorbed quickly by the lungs. One study reported that approximately 75% of the inhaled chemical was absorbed through the lungs in humans.

1,2-DCE is largely excreted through the lungs.

用途と製造

Uses · 6 件

Used as a solvent and chemical intermediate; [ACGIH] Used as a refrigerant, degreaser, dry cleaning agent, and solvent for perfumes, adhesives, lacquers, oils, and resins; [HSDB] Only the trans isomer is commercially available in the US--used for precision cleaning of electronic components and a small amount used as a blowing agent for specialty foams; [EPA Toxicological Review, 2010]

Metal Degreasing [Category: Clean]

1,2-Dichloroethylenes can be used as solvent for waxes, resins, lacquers, and thermoplastics; for the extraction of oil and fats from fish and meat; for vapor degreasing, as surface cleaning agent; for the extraction of rubber, as foam blowing additive; as refrigerant; in the manufacture of pharmaceuticals, and as source of HCl in silicone etching. /1,2-Dichloroethylenes/

... /Used/ as a refrigerant, in the manufacture of pharmaceuticals and artificial pearls, and in the extraction of oils and fats from fish and meat.

Solvent for fats, phenol, camphor, etc. Intermediate in synthesis of chlorinated solvents and compounds.

1,2-DCE is used as a direct solvent for perfumes, dyes, gums and waxes, oils, lacquers, thermoplastics, phenols, and camphor; as a chemical intermediate for chlorinated compounds; as an agent in retarding fermentation. 1,2-DCE is used as a low-temperature solvent for heat-sensitive substances in the extraction of caffeine, fats, and natural rubber. It is also used in organic synthesis for polymers and telomers, in addition to miscellaneous application as a dry cleaning solvent, cleaning solution for printed circuit boards, food packaging adhesives, and germicidal fumigants.

U.S. Production · 5 件

2023: <50,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#494]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Ethene, 1,2-dichloro-. Aggregated National Production Volume: 10 to < 50 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethene, 1,2-dichloro-. National Production Volume: Withheld.

Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1,2-Dichloroethylene.

Methods of Manufacturing · 4 件

In the thermal dehydrochlorination of 1,1,2-trichloroethane, the 1,2-dichloroethylenes are obtained together with the 1,1-isomer. With increasing temperature, formation of the 1,2-isomers increases. The trans isomer is preferentially formed. With catalysts, the individual ratios can be varied to some extent. /1,2-Dichloroethylenes/

Preparation: Bordner, United States of America patent 2504919 (1950 to Du Pont).

1,2-Dichloroethylene can be produced by direct chlorination of acetylene at 40 °C.

Reduction of 1,1,2,2-tetrachloroethane with steam over an iron catalyst

Formulations/Preparations · 2 件

Grades: Technical, as cis, trans, and mixture of both.

97% pure

Use ClassificationChemical Classes -> Volatile organic compounds
General Manufacturing Information · 4 件

Ethene, 1,2-dichloro-: ACTIVE

1,2-Dichloroethylene exists as symmetrical, cis- 60%, and trans- 40%.

Trans-isomer is more widely used in industry than either the cis-isomer or the commercial mixture.

Because of the relatively low demand for 1,2-dichloroethylenes they are not deliberately produced in large quantities. They occur as byproducts in some processes, such as the production of vinyl chloride, trichloroethylene, and tetrachloroethylene and can be withdrawn and purified if required. /1,2-Dichloroethylenes/

応用分野 · 4 件

解説① 1,2-ジクロロエチレンClCH=CHCl.この化合物のことを誤って二塩化エチレンということがあるが,二塩化エチレンは飽和化合物で,まったく別の化合物であるから,混同してはいけない.② 1,1-ジクロロエチレンCH2=CCl2.塩化ビニリデンの別名.

説明Acetylene dichloride is a colourless liquid (usually a mixture of the cis and trans isomers) with a slightly acrid, chloroform-like odour. Acetylene dichloride is a chemical used mainly in the production of perfumes, dyes, and thermoplastics. The type and severity of symptoms varies depending on the amount of chemical involved and the nature of the exposure. It is incompatible with strong oxidisers, strong alkalis, potassium hydroxide, and copper. Acetylene dichloride is highly flammable and in a fire gives off irritating or toxic fumes/gases. (Acetylene dichloride usually contains inhibitors to prevent polymerisation.)

使用1,2-Dichloroethylene is used as a solvent for organic materials and as an intermediate in the synthesis of other chlorinated compounds; it may be produced by the chlorination of acetylene but is often produced as a by-product in the manufacture of other chlorinated compounds.

一般的な説明A clear colorless liquid with ether-like odor. Mixture of cis and trans isomers. Flashpoint 36 - 43° F. Denser than water and insoluble in water. Vapors heavier than air.

調製方法

純化方法Shake it successively with conc H2SO4, water, aqueous NaHCO3 and water. Dry it with MgSO4 and fractionally distil it to separate the cis-and trans-isomers. [Beilstein 1 IV 707-709.]

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