1,1,2,2-Tetrachloroethane

HCID 6591CAS 25322-20-7

Grundinformationen

Standard-SMILES
ClC(Cl)C(Cl)Cl
InChIKey
QPFMBZIOSGYJDE-UHFFFAOYSA-N
Summenformel
C2H2Cl4
Durchschnittliche Molmasse
167,8 g/mol
Monoisotopische Masse
165,89106078

Überblick

1,1,2,2-Tetrachloroethane is a manufactured, colorless, dense liquid that does not burn easily. It is volatile and has a sweet odor. In the past, it was used in large amounts to produce other chemicals, as an industrial solvent to clean and degrease metals, and as an ingredient in paints and pesticides. Commercial production of 1,1,2,2-tetrachloroethane for these uses has stopped in the United States. It presently is used only as a chemical intermediate in the production of other chemicals.

Namen und Bezeichner

Bevorzugter Name
1,1,2,2-Tetrachloroethane
IUPAC
1,1,2,2-tetrachloroethane
Englischer Name
1,1,2,2-Tetrach loroethane
Summenformel
C2H2Cl4
Molmasse
167.84928

Namen und Synonyme

1,1,2,2-TETRACHLOROETHANE79-34-5s-TetrachloroethaneAcetylene tetrachloridesym-TetrachloroethaneBonoformCellonEthane, 1,1,2,2-tetrachloro-WestronTetrachlorethane1,1,2,2-Tetrachlorethane1,1,2,2-Tetrachloraethan
Weitere Namen anzeigen
TCE (ambiguous)1,1-Dichloro-2,2-dichloroethaneTetrachlorure d'acetyleneRCRA waste number U209NCI-C03554DTXSID70213181,1,2,2-Tetracloroetano1,1,2,2-Czterochloroetan

Datenbank-Bezeichner

CAS
25322-20-7、630-20-6、79-34-5
PubChem CID
6591
DTXSID
DTXSID7021318
ChEMBL
CHEMBL47258
ChEBI
CHEBI:36026
UNII
1L6BI049XV
EC Number
201-197-8
Nikkaji
J43.353E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,4
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
1
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 4 Einträge

Hazardous Air Pollutants (HAPs)

Urban Hazardous Air Pollutants (HAPs) - EPA specified greatest potential health threat in urban areas

Carcinogens

Volatile Organic Compound (VOC)

SolventsSolvents -> Chlorinated Aliphatics
SpringerMaterials PropertiesBoiling point
PesticidesPesticide -> EPA IRIS
LogP · 3 Einträge

log Kow = 2.39

2.39

2.39

Odor · 3 Einträge

Sweetish suffocating chloroform-like odor

Pungent, chloroform-like odor

Sweetish odor

Physikochemische Eigenschaften

Schmelzpunkt
-43 °C · -43 °C
Siedepunkt
147 °C · 147 °C
Dichte
1.59 · 1.59
Dampfdichte
5.8 · 5.8 (vs air)
Dampfdruck
10.7 hPa · 10.7 hPa at 20°C
Aggregatzustand
Liquid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H310: Fatal in contact with skin [Danger Acute toxicity, dermal]

P260, P262, P264, P270, P271, P273, P280, P284, P302+P352, P304+P340, P316, P320, P321, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H302 (16.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P317, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Ethane, 1,1,2,2-tetrachloro-

Hazard Traits - Carcinogenicity; Cardiovascular Toxicity; Hepatotoxicity and Digestive System Toxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Ocular Toxicity; Respiratory Toxicity

Ethane, 1,1,2,2-tetrachloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,1,2,2-tetrachloro- 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)

Restricted substance: 1,1,2,2-Tetrachloroethane

Ethane, 1,1,2,2-tetrachloro-: HSNO Approval: HSR001524 Approved with controls

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.)

Other Safety InformationIMAP assessments - Ethane, 1,1,2,2-tetrachloro-: Environment tier I assessment
DOT Label · 2 Einträge

Poison

Poison

Fire Hazards · 4 Einträge

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Special Hazards of Combustion Products: Irritating hydrogen chloride vapor may form in fire. (USCG, 1999)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire Potential1,1,2,2-Tetrachloroethane itself does not burn.
Health Hazards · 3 Einträge

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Compound is a powerful narcotic and liver poison; may also cause changes in blood composition and neurological disturbances. Repeated exposure by inhalation can be fatal. Ingestion causes vomiting, diarrhea, severe mucosal injury, liver necrosis, cyanosis, unconsciousness, loss of reflexes, and death. Contact with eyes causes irritation and lachrymation. Can be absorbed through the skin and may produce severe skin lesions. (USCG, 1999)

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

Sicherheit und Schutzausrüstung

Fire Fighting · 3 Einträge

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 Einträge

Fresh air, rest. Artificial respiration may be needed. Refer immediately for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2 Einträge

· 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.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

First Aid · 4 Einträge

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

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 StorageSeparated from strong bases, alkali metals and food and feedstuffs. Well closed. Cool. Keep in the dark. Ventilation along the floor. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Exposure Control and Personal Protection · 2 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

1.0 [ppm]

Toxikologische Informationen

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden1,1,2,2-Tetrachloroethane was detected in the adipose tissue, liver and lungs of humans(1). 1,1,2,2-Tetrachloroethane was detected but not quantified in human blood(2).
Treatment · 1 Eintrag

There is no specific treatment for trichloroethane poisoning. Gastric lavage is recommended after oral exposure. Protect airway by placement in Trendelenburg and left lateral decubitus position or by endotracheal intubation. Control any seizures first. In case of seizures following ingestion, administer a benzodiazepine IV. Following inhalation, 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. After eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurs through dermal contact, remove contaminated clothing and wash exposed area thoroughly with soap and water. In any case, a physician may need to examine the area if irritation or pain persists. (T36)

Cancer Sites · 2 Einträge

Hepatic

[in animals: liver tumors]

Interactions · 4 Einträge

Dolichols are long-chain polyprenols containing 14-22 isoprene units, present in mammalian tissues as free dolichol (Free-Dol), fatty acyl dolichyl esters (Dol-FA), and dolichyl phosphate (Dol-P). The hepatic level of Dol-P seems to be a rate-limiting factor for glycosylation processes. Previous studies from our laboratory demonstrated the susceptibility of the dolichol molecule to undergo radical attacks. Since the toxicity of 1,1,2,2-tetrachloroethane (TTCE)is dependent on the free-radical production during hepatic biotransformation, it was of interest to determine whether this haloalkane might affect glycosylation mechanisms by changing dolichol levels and distribution in rat liver microsomes and Golgi apparatus (GA). Male Sprague-Dawley rats received a single dose of TTCE (574 mg/kg bw) and were then sacrificed at different times (5, 15, 30, or 60 min). In the TTCE-treated rats both serum aspartate aminotransferase (AST) and alanine aminotransferase (ALT) activities and hepatic triglycerides (TG) were significantly higher than control, while microsomal glucose 6-phosphatase (G6Pase) activity was decreased. In total microsomes Dol-P levels considered rate-limiting for the biosynthesis of the N-glycosylated proteins were significantly lower than in the control group 15 min after TTCE treatment. In normal rat liver, F1 secretory fraction of CA is 60-fold enriched in total dolichol content with respect to microsomes. In this compartment the total dolichol content, essential for the increase in membrane fluidity and permeability required for glycoprotein maturation and secretion, decreased significantly 5 min after TTCE treatment. Our results suggest that TTCE may affect dolichol functions in rat liver.

Alcohol, an inducer of cytochrome P-450 form IIEl, increased the metabolism of 1,1,2,2-tetrachloroethane and intensified the effects of 1,1,2,2-tetrachloroethane in rats. This indicates that humans who consume alcohol may be at increased risk for toxic effects from 1,1,2,2-tetrachloroethane. This is also the case for several other chlorinated aliphatic hydrocarbons. However, although alcohol combined with 1,1,2,2-tetrachloroethane increased the relative weight of the testes in rats, it did not alter the effects of 1,1,2,2- tetrachloroethane on the histopathology or function in the liver, nor was there damage to the kidneys, spleen, adrenals, brain, or thyroid.

In efforts to find treatments for acute-duration 1,1,2,2-tetrachloroethane poisoning, various substances have been tested to determine if they altered the toxicity of 1,1,2,2-tetrachloroethane in rats. The survival times were increased when 1,1,2,2-tetrachloroethane was administered with castor oil, but decreased when administered orally with milk. Survival time was also decreased when 1,1,2,2-tetrachloroethane was given with mineral oil or with paraffin.

Acetone pretreatment did not increase the severity of liver injury in rats given 1,1,2,2-tetrachloroethane. Additionally, rats given 1,1,2,2-tetrachloroethane in addition to 1,1-dichloroethylene or tetrachloroethylene exhibited a decrease in hepatotoxicity from animals given 1,1-dichloroethylene or tetrachloroethylene alone.

Target Organs · 3 Einträge

Hepatic (Liver), Neurological (Nervous System)

Hepatic

Skin, liver, kidneys, central nervous system, gastrointestinal tract

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

U209; As stipulated in 40 CFR 261.33, when 1,1,2,2-tetrachloroethane 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).

Atmospheric Standards · 2 Einträge

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Tetrachloroethanes are produced, as an intermediate or a final product, by process units covered under this subpart. /Tetrachloroethanes/

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 1,1,2,2-Tetrachloroethane is included on this list.

CERCLA Reportable Quantities · 1 Eintrag

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 100 lb or 45.4 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).

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. /Chlorinated ethanes/
State Drinking Water Standards · 2 Einträge

(CA) CALIFORNIA 1 ug/L

(NJ) NEW JERSEY 1 ug/L

State Drinking Water Guidelines · 5 Einträge

(AZ) ARIZONA 0.17 ug/L

(CT) CONNECTICUT 28 ug/L

(FL) FLORIDA 1 ug/L

(ME) 1.8 ug/L

For more State Drinking Water Guidelines (Complete) data for 1,1,2,2-TETRACHLOROETHANE (6 total), please visit the HSDB record page.

Sicherheitsdaten

ridadr
UN 1702
hazard_class
6.1
packing_group
II

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 6 Einträge

The biotransformation of 1,1,2,2-tetrachloroethane is complex; dichloroacetic acid has been identified as the major urinary metabolite, along with trichloroethanol and trichloroacetic acid. The formation of the latter two metabolites was suggested to be due to reductive biotransformation of 1,1,2,2-tetrachloroethane to give trichloroethene, which may be further oxidized to chloral hydrate by cytochrome p450. Trichloroethanol and trichloroacetic acid are formed from chloral hydrate by reduction and respiratory oxidation and are major urinary metabolites of trichloroethene. Hydroxylation of 1,1,2,2-tetrachloroethane, yielding dichloroacetyl chloride, is the predominant pathway to dichloroacetic acid

Tetrachloroethane when admin for 8 hr as vapor at 200 ppm to rats & mice, produced fujiwara reaction-positive urinary metabolites, trichloroacetic acid, trichloroethanol & total trichloro cmpd in yields consistent with their vapor pressure & ease of metabolic conversion.

Incubation of 1,2-(14)C-labeled 1,1,2,2-tetrachloroethane with a reconstituted monooxygenase system or with intact rat liver microsomes led to the formation of a metabolite capable of binding covalently to proteins and other nucleophiles. The enzyme system responsible for metabolizing tetrachloroethane to both soluble and covalently bound metabolites was induced by phenobarbital or xylene but not by beta-naphthoflavone treatment. The results are consistent with a scheme whereby 1,1,2,2-tetrachloroethane is metabolized by cytochrome P450 to dichloroacetyl chloride, which can bind covalently to various nucleophiles or hydrolyze to dichloroacetic acid.

... 1,1,2,2-Tetrachloroethane appears to be metabolized by hepatic nuclear cytochrome P450, and ... converted to chlorinated metabolites after incubation with hepatic nuclei and an NADPH-generating system plus EDTA, with the omission of any component eliminating metabolite production.

For more Metabolism/Metabolites (Complete) data for 1,1,2,2-TETRACHLOROETHANE (6 total), please visit the HSDB record page.

1,1,2,2-tetrachloroethane appears to be distributed throughout the body, but may selectively accumulate to a degree in certain cells and tissues. Because it is a volatile, lipophilic molecule of small molecular size that appears to be readily absorbed from the respiratory and gastrointestinal tracts, passive diffusion is the most likely mechanism of absorption. The metabolism of 1,1,2,2-tetrachloroethane proceeds via multiple pathways. The predominant pathway appears to involve production of dichloroacetic acid, formed as an initial metabolite via stagewise hydrolytic cleavage of 1,1,2,2-tetrachloroethane, or by cytochrome P450-based oxidation of 1,1,2,2-tetrachloroethane. Dichloroacetic acid has been identified as the major urinary metabolite. Dichloroacetic acid can be further metabolized to glyoxylic acid, formic acid, and carbon dioxide, with carbon dioxide a potential major component of the end products. Other pathways involve the formation of trichloroethylene or tetrachloroethylene as initial metabolites, with subsequent reactions yielding trichloroethanol, trichloroacetic acid, and oxalic acid as important end products. Metabolism of 1,1,2,2-tetrachloroethane is generally extensive, with 68% or more of a total administered dose found as metabolites. Following absorption into the body, 1,1,2,2-tetrachloroethane is eliminated mainly as metabolites in the urine and as carbon dioxide and unchanged compound in expired air. (L336)

Absorption, Distribution and Excretion · 5 Einträge

1,1,2,2-Tetrachloroethane is readily absorbed following inhalation, ingestion, and dermal exposure and rapidly distributed in tissue compartments by passive processes. Respiration is the route of excretion for non-transformed 1,1,2,2-tetrachlororethane, volatile metabolites and terminal metabolite CO(2). Most of the metabolites are excreted by the urinary route but also by the feces and skin. In mice, urinary metabolites represent about 1/3 of the absorbed dose.

Half of a dose of (14)C-labeled 1,1,2,2-tetrachloroethane (0.21-0.32 g/kg, ip) was expired from mouse as labeled CO2 within 3 days & 28% excreted in urine.

About 97% of inhaled 1,1,2,2-tetrachloroethane was retained in the /human/ lung 1 hr after exposure ... .

Following oral administration, 1,1,2,2-Tetrachloroethane (TCE) is readily absorbed in the GI tract and apparently readily excreted by the lungs.

For more Absorption, Distribution and Excretion (Complete) data for 1,1,2,2-TETRACHLOROETHANE (9 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

The production of 1,1,2,2-tetrachloroethane as an end-product has decreased significantly in the United States. It was also used as a solvent, in cleaning and degreasing metals, in paint removers, varnishes and lacquers, in photographic films, as an extractant for oils and fats, and in pesticides.

Used in synthesis of organic chemicals; used in the past as a solvent for degreasing and extracting; [ACGIH] Used as a nonflammable solvent for fats, oils, waxes, resins, cellulose acetate, rubber, copal, phosphorus, and sulfur, as a solvent in certain types of Friedel-Crafts reactions or phthalic anhydride condensations, to make paints, varnishes, rust removers, trichloroethylene, and other chlorinated hydrocarbons with two carbon atoms, in soil sterilization, weed killer, and insecticide formulations, in the determination of theobromine in cacao, as immersion fluid in crystallography, and to produce pathological changes in gastrointestinal tract, liver, and kidneys in the laboratory; [Merck Index] Other uses include alcohol denaturant, fumigant, dry cleaning agent, in photographic film, cement, and to make artificial silk, leather, and pearls; [NTP] Currently only produced and consumed on site in closed systems for the synthesis of other chlorinated hydrocarbons; [Reference #1]

Not found in any pesticide products registered in the US; [NPIRS]

Metal Degreasing [Category: Clean]

For 1,1,2,2-tetrachloroethane (USEPA/OPP Pesticide Code: 078601) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Nonflammable solvent for fats, oils, waxes, resins, cellulose acetate, rubber, copal, phosphorus, sulfur. As solvent in certain types of Friedel-Crafts reactions or phthalic anhydride condensations. In the manufacture of paint, varnish, and rust removers. In soil sterilization and weed killer and insecticide formulations. In the determination of theobromine in cacao. As immersion fluid in crystallography. In the biological laboratory to produce pathological changes in gastrointestinal tract, liver and kidneys. Intermediate in the manufacture of trichloroethylene and other chlorinated hydrocarbons having two carbon atoms.

Impurities/SRP/: 1,1,1,2-Tetrachloroethane is an impurity found in technical grade 1,1,2,2-tetrachloroethane.
U.S. Imports(1985) 6.11X10+7 g
U.S. Production · 5 Einträge

2023: 2,500,000 - <4,000,000 lb

Production figures for 1,1,2,2-tetrachloroethane cannot be estimated.

Ethane, 1,1,2,2-tetrachloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Ethane, 1,1,2,2-tetrachloro-. Aggregated National Production Volume: 1 to < 10 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: Ethane, 1,1,2,2-tetrachloro-. National Production Volume: Withheld.

Industry UsesIntermediate
Methods of Manufacturing · 5 Einträge

Manufactured by catalytic addition of chlorine to acetylene; ... by chlorination of ethylene; ... by catalytic chlorination of ethane; ... by chlorination of 1,2-dichloroethane.

Chlorination or oxychlorination of ethylene.

Produced by direct chlorination or oxychlorination utilizing ethylene as feedstock. In most cases, 1,1,2,2-tetrachloroethane is not isolated, but immediately thermally cracked at 454 °C to give the desired trichloroethylene and tetrachloroethylene products. ... High purity 1,1,2,2- tetrachloroethane is made by chlorinating acetylene.

Industrial processes for the production of 1,1,2,2-tetrachloroethane consist of two main routes: 1. Addition of chlorine to acetylene /and/ ... 2. Liquid-phase chlorination of ethylene or 1,2-dichloroethane.

The liquid-phase chlorination of vinyl chloride or 1,1,2-trichloroethane in the presence of AlCl3 as catalyst yields 1,1,2,2-tetrachloroethane with high selectivity.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
河南多贝化工有限公司0370-6999054 17550096163 · [email protected]

Zugehörige Reaktionen

103

Verknüpfte Notizen

Wird geladen…