Chlortrifluorethylen

Chlorotrifluoroethylene

HCID 6594CAS 79-38-9

Grundinformationen

Standard-SMILES
FC(F)=C(F)Cl
InChIKey
UUAGAQFQZIEFAH-UHFFFAOYSA-N
Summenformel
C2ClF3
Durchschnittliche Molmasse
116,47 g/mol
Monoisotopische Masse
115,96406234

Überblick

Trifluorochloroethylene is a colorless gas with a faint ethereal odor. It is shipped as a liquefied gas under its vapor pressure. It is very toxic by inhalation and is easily ignited. The vapors are heavier than air and a flame can flash back to the source of leak very easily. This leak can either be a liquid or vapor leak. The vapors can asphyxiate by the displacement of air. Contact with the liquid can cause frostbite. Under prolonged exposure to intense heat or fire the containers may violently rupture and rocket, or the material may polymerize with possible container rupture.

Namen und Bezeichner

Bevorzugter Name
Chlorotrifluoroethylene
IUPAC
1-chloro-1,2,2-trifluoroethene
Lokaler Name
Chlortrifluorethylen
Englischer Name
Chlorotrifluoroethylene
Summenformel
C2ClF3
Molmasse
116.47

Namen und Synonyme

CHLOROTRIFLUOROETHYLENE79-38-9ChlorotrifluoroetheneTritheneDaiflonTrifluorochloroethyleneFluoroplast 3CTFETrifluorovinyl chlorideEthene, chlorotrifluoro-Genetron 1113Monochlorotrifluoroethylene
Weitere Namen anzeigen
R11131-Chloro-1,2,2-trifluoroethenecfeC2F3ClCFClFC-1113
Ethylene, chlorotrifluoro-TrifluorchlorethylenChlortrifluoraethylenTrifluoromonochloroethyleneEthylene, trifluorochloro-1,1,2-Trifluoro-2-chloroethylene2-Chloro-1,1,2-trifluoroethylene1-Chloro-1,2,2-trifluoroethylene

Datenbank-Bezeichner

CAS
79-38-9
PubChem CID
6594
DTXSID
DTXSID3026485
UNII
AF215GW34G
EC Number
201-201-8
Nikkaji
J35.200D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,9
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
6

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Flammable agents - 4th degree

PFAS · 4 Einträge

PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

PFAS -> Other/unspecified

PFAS -> Fluoropolymers

PFAS -> Other/unspecified

SpringerMaterials PropertiesCoriolis coupling
OdorFaint etheral odor
Density · 5 Einträge

1.307 at 68 °F (USCG, 1999) - Denser than water; will sink

1.54 g/cu cm at -60 °C

Density: 1.305 (liquid) at 20 °C

Relative density (water = 1): 1.3

1.54 @ 60°C

Color/FormColorless gas

Physikochemische Eigenschaften

Schmelzpunkt
158 °C · −158 °C(lit.)
Siedepunkt
28.4 °C · −28.4 °C(lit.)
Dichte
1 · 1,305 g/cm3
Dampfdichte
4.13 · 4.13 (vs air)
Dampfdruck
612 kPa · 612kPa at 25℃
Brechungsindex
1.38 · 1.3800

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H220 (89.2%): Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P261, P264, P270, P271, P280, P301+P316, P304+P340, P316, P321, P330, P377, P381, P403, P403+P233, P405, P410+P403, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 139 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H220: Extremely flammable gas [Danger Flammable gases]

Gefahrenhinweise

Hazards Identification · 2 Einträge

Toxic/poison by inhalation (TIH/PIH)

Toxic/poison by inhalation (TIH/PIH)

Regulatory Information · 5 Einträge

Chemical: Ethene, chlorotrifluoro-

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

Status: Active Update: 06-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13752

Chlorotrifluorethylene: HSNO Approval: HSR006726 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.)

DOT LabelPoison Gas Flammable Gas
Fire Hazards · 4 Einträge

Special Hazards of Combustion Products: Toxic hydrogen chloride and hydrogen fluoride gases are formed.

· Flammable; may be ignited by heat, sparks or flames.

· Flammable; may be ignited by heat, sparks or flames.

Flammable. Gas/air mixtures are explosive.

Fire PotentialVery dangerous fire hazard when exposed to heat, flames (sparks), or oxidizers.
Health Hazards · 3 Einträge

Inhalation causes dizziness, nausea, vomiting; liver and kidney injury may develop after several hours and cause jaundice and necrosis of the kidney. Contact with liquid causes frostbite of eyes and possibly of skin. (USCG, 1999)

· TOXIC; may be fatal if inhaled or absorbed through skin. Some may cause severe skin burns and eye damage.

· TOXIC; may be fatal if inhaled or absorbed through skin. Some may cause severe skin burns and eye damage.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 119 [Gases - Toxic - Flammable; polymerization hazard]:

Shut off supply; if not possible and no risk to surroundings, let the fire burn itself out. In other cases extinguish with water spray, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep cylinder cool by spraying with water. Combat fire from a sheltered position.

First Aid Measures · 3 Einträge

Fresh air, rest.

ON FROSTBITE: rinse with plenty of water, do NOT remove clothes.

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

Accidental Release Measures · 4 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.

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

· 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 Einträge

Call a physician after all exposures to this compound; it is more toxic than most of the closely related propellant gases.

General First Aid:

General First Aid:

Safe StorageFireproof. Cool.
Exposure Control and Personal Protection · 3 Einträge

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

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

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Toxikologische Informationen

Interactions · 1 Eintrag

The effect of isoflurane on the anaerobic metabolism of halothane to chlorodifluoroethene (CDE) and chlorotrifluoroethane (CTE) was studied with microsomes of guinea pig liver. The Km values for chlorotrifluoroethane formation were 1204.74, 553.75, 521.14, 560.67, and 711.05 uM at 0 mM, 0.12 mM, 0.29 mM, 0.58 mM and 1.16 mM isoflurane, respectively. In contrast, the Vmax values for chlorodifluoroethene and chlorotrifluoethane formation at these isoflurane concentrations were not significantly different than in the control groups. The production of chlorodifluoroethene and chlorotrifluoroethane was significantly increased by isoflurane, at concentrations up to 0.58 mM.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 95(SRC), determined from a structure estimation method(2), indicates that chlorotrifluoroethylene is expected to have high mobility in soil(SRC). Volatilization of chlorotrifluoroethylene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.31 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Chlorotrifluoroethylene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.59X10+3 mm Hg at 25 °C(4). Biodegradation data in soil were not available(SRC,2010).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 95(SRC), determined from a structure estimation method(2), indicates that chlorotrifluoroethylene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.31 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 6(SRC), from an estimated log Kow of 1.65(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2010).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorotrifluoroethylene, which has a vapor pressure of 4.59X10+3 mm Hg at 25 °C(2), is expected to exist solely as a gas in the ambient atmosphere. Gas-phase chlorotrifluoroethylene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.5 days(SRC), calculated from its rate constant of 7.0X10-12 cu cm/molecule-sec at 25 °C(3). The rate constant for the vapor-phase reaction of chlorotrifluoroethylene with ozone has been estimated as 0.002X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). This corresponds to an atmospheric half-life of about 720 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(5). The chlorine-atom initiated oxidation of chlorotrifluoroethylene in the atmosphere gives CClF2CF(O) as the major product; the quantum yield of oxidation for this reaction is >1000 relative to the quantum yield for olefin(6). A rate constant of 2.7X10-11 cm cu/mol sec is reported for the reaction of chlorotrifluoroethylene with atomic oxygen(7). Chlorotrifluoroethylene does not contain chromophores that absorb at wavelengths >290 nm(8), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation.
Signs and Symptoms · 2 Einträge

Dizziness. Nausea.

ON CONTACT WITH LIQUID: FROSTBITE.

Effluent ConcentrationsChlorotrifluoroethylene was detected, not quantified in a groundwater sample near the Gloucester landfill, used for disposal of organic chemicals from the Government's laboratories in Ottawa, in Ontario Canada(1).

Regulatorische Informationen

DHS Chemicals of Interest (COI) · 6 Einträge

Trifluorochloroethylene

1

10000

66.67

500

Flammable chemical that can be released at a facility.

State Drinking Water Guidelines(NH) NEW HAMPSHIRE 5.0 ug/L

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 1082 (TRIFLUOROCHLORO- ETHYLENE, STABILIZED (REFRIGERANT GAS R 1113))
hs_code
2903779010
RTECS-Nr.
KV0525000
risk_code
12-20/22

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 5 Einträge

Two metabolites of CTFE were identified as potent nephrotoxins in male rats, S-(2-chloro-1,1,2-trifluoroethyl)glutathione (CTFG) and S-(2-chloro-1,1,2-trifluoroethyl)cysteine (CTFC). In this investigation both CTFG and CTFC were synthesized and given to the male rats at dose levels of 50 umol/kg of CTFG or 100 umol of CTFC. It was concluded that the metabolites of CTFE are the active nephrotoxins, not CTFE.

This study describes in vivo bioactivation of CTFE which proceeds as follows: hepatic glutathione S-conjugate formation, peptidase-catalyzed metabolism of the glutathione S-conjugates to the corresponding cysteine S-conjugates, uptake of cysteine S-conjugates by the kidneys, and renal cysteine conjugate beta-lyase-catalyzed beta-elimination of a thiol. The CTFE conjugate was shown to be capable of acylating renal proteins using (19)F NMR.

Since halogenated vinyl cysteine conjugates are known to be potent nephrotoxicants, chlorotrifluoroethylene was studied for its ability to be metabolically activated to the cysteine conjugate. This was shown not to occur in a biological system. However, if a glutathione adduct of chlorotrifluoroethylene is synthesized, this adduct was shown to degrade non-enzymatically to form the cysteine conjugate. Thus, incubation of chlorotrifluoroethylene with a renal cortex brush border preparation high in C-S lyase did not result in the formation of pyruvate, indicating the lack of ability of a renal preparation to directly activate chlorotrifluoroethylene presumably because of the inability to form the glutathione adduct.

Chlorotrifluoroethylene, a substrate for glutathione S-transferase activity in rat hepatic cytosolic and microsomal fractions, was investigated, wherein the rates of reaction were determined by measuring glutathione disappearance, at 5-15 or 35-70 nmol/min/mg of cytosolic or microsomal protein, respectively. A product of the cytosol-catalyzed reaction between chlorotrifluoroethylene and glutathione was S-(2-chloro-1,1,2-trifluoroethyl)glutathione. The glutathione S-transferase-catalyzed addition reaction with a halogenated olefin may be of toxicological significance.

For more Metabolism/Metabolites (Complete) data for Chlorotrifluoroethylene (9 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 1 Eintrag

After exposure of rabbits to trifluorochloroethylene at 0.1%, the alveolar absorption rate was 5.80%. Trifluorochloroethylene was detected in blood and urine. The kidney, bone, and lung had the highest distribution among various organs examined.

Verwendung und Herstellung

Uses · 6 Einträge

Used to make chlorotrifluoroethylene resins (Kel-F, Halar); Used in the synthesis of lubricants, plastics, elastomers, and other chemical products; [HSDB]

Intermediate; monomer for chlorotrifluoroethylene resins

Chloro trifluoroethylene is polymerized to produce Kel-F /extremely chemically inert material/

Chloro trifluoroethylene is used extensively in the synthesis of high performance lubricants, plastics and elastomers

Bromination of chlorotrifluoroethylene is the convenient way to prepare bromotrifluoroethylene with high yield

Chlorotrifluoroethylene is a starting material for homopolymers and copolymers the latter are commercially available under the trade name Halar (Allied). Chlorotrifluoroethylene is an intermediate in the production of the inhalation anesthetic halothane. An addition product of chlorotrifluoroethylene with diethylamine,(2-chloro-1,1,2-trifluoroethyl)-diethylamine, is used as a fluorinating agent to replace hydroxyl groups in steroids and carbohydrates with fluorine. Chlorotrifluoroethylene is used in telomerization with carbon tetrachloride or chloroform for use as inert fluids, hydraulic fluids, or lubricants.

ImpuritiesTrichloroethylene, 1.0%, Chlorodifluoroethylene 0.05%
U.S. Production · 4 Einträge

2023: 10,000,000 - <50,000,000 lb

Ethene, chlorotrifluoro- 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 volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4177]

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

Industry UsesMonomers
Methods of Manufacturing · 1 Eintrag

Chlorotrifluoroethylene is produced commercially by dechlorination of 1,1,2-trichloro-1,2,2-trifluoroethane, with zinc in methanol. An alternative route is dechlorination in the gas phase, eg, on an aluminum fluoride-nickel phosphate catalyst; this catalyst is highly stable.

Formulations/PreparationsGRADES: Technical, 99.0%

Anwendungen

VerwendenIntermediate, monomer for chlorotrifluoroethylene resins.

Darstellung · 1 Eintrag

synthetischeChlorotrifluoroethylene is prepared from ethylene by the following route:Ethylene is treated with an excess of chlorine at 300-350C in the presence of activated charcoal to give hexachloroethane. This product is then treated with hydrogen fluoride in the presence of antimony pentachloride to yield trichlorotrifluoroethane. Dechlorination in the liquid phase with zinc dust and ethanol results in the formation of chlorotrifluoroethylene which is washed with water to remove alcohol, dried and distilled under pressure.

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