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Chlortrifluorethylen
CTFE · R1113 · 1-Chloro-1,2,2-trifluoroethene · cfe · C2F3Cl · CHLOROTRIFLUOROETHENE · 1-Chloro-1,2,2-trifluoroethylene · CFCl
Identifikatoren & physikalische Daten
| CAS No. | 79-38-9 |
|---|---|
| Summenformel | C2ClF3 |
| Durchschnittliche Molmasse | 116,47 g/mol |
| Monoisotopische Masse | 115,96406234 g/mol |
| SMILES | FC(F)=C(F)Cl |
| InChIKey | UUAGAQFQZIEFAH-UHFFFAOYSA-N |
| PubChem CID | 6594 |
| EC No. | 201-201-8 |
| DTXSID | DTXSID3026485 |
| Lokaler Name | Chlortrifluorethylen |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 6 |
| Formalladung | 0 |
| Komplexität | 72,9 |
| Stoffklassen | Toxic Gases & Vapors -> Other Toxic Gases & VaporsFlammable agents - 4th degree |
| PFAS | PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008PFAS -> Other/unspecifiedPFAS -> Fluoropolymers |
| SpringerMaterials Properties | Coriolis coupling |
| Geruch | Faint etheral odor |
| Dichte | 1.307 at 68 °F (USCG, 1999) - Denser than waterwill sink1.54 g/cu cm at -60 °CDensity: 1.305 (liquid) at 20 °CRelative density (water = 1): 1.31.54 @ 60°C1,305 g/cm3 |
| Color/Form | Colorless gas |
| Löslichkeit | Soluble in benzene, chloroform380mg/L at 28℃ |
| Flammpunkt | -27.8 °C-28°C |
| Siedepunkt | -18 °F at 760 mmHg (USCG, 1999)-27.8 °C-28 °C-27.8 °C @760 [mm Hg]−28.4 °C(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /fluorine/ and /chlorine/.At higher temperatures (>250 °C) decomposition products may include hydrofluoric acid and carbonyl halides such as phosgene. |
| Schmelzpunkt | -158.2 °C-158 °C−158 °C(lit.) |
| Dampfdichte | Relative vapor density (air = 1): 4.024.13 (vs air) |
| Dampfdruck | 612kPa at 25℃ |
| Brechungsindex | 1.3800 |
| Spezifische Wärmekapazität | Cp(gas): 0.72 J/(g·K), at 25℃ |
| Henry-Konstante | 3.2×10-5 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | InChI=1S/C2ClF3/c3-1(4)2(5)6 |
| InChIKey | UUAGAQFQZIEFAH-UHFFFAOYSA-N |
| SMILES | C(/Cl)(\F)=C(\F)/F |
| LogP (Verteilungskoeffizient) | 1.65 |
| CAS Datenbank | 79-38-9(CAS DataBase Reference) |
| NIST chemische Informationen | Ethene, chlorotrifluoro-(79-38-9) |
| EPA chemische Informationen | Chlorotrifluoroethylene (79-38-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH220 (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.H220: Extremely flammable gas [Danger Flammable gases] |
|---|---|
| Hazards Identification | Toxic/poison by inhalation (TIH/PIH) |
| Regulatorische Informationen | 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/13752Chlorotrifluorethylene: HSNO Approval: HSR006726 Approved with controlsThe 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-Kennzeichnung | Poison Gas Flammable Gas |
| Brandgefahren | Special Hazards of Combustion Products: Toxic hydrogen chloride and hydrogen fluoride gases are formed.· Flammablemay be ignited by heat, sparks or flames.Flammable. Gas/air mixtures are explosive. |
| Brandpotenzial | Very dangerous fire hazard when exposed to heat, flames (sparks), or oxidizers. |
| Gesundheitsgefahren | Inhalation causes dizziness, nausea, vomitingliver 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)· TOXICmay be fatal if inhaled or absorbed through skin. Some may cause severe skin burns and eye damage. |
| Gefahrenübersicht | Can cause frostbiteInhalation can result in dizziness and nausea at lower concentrations and cardiac sensitization and CNS depression at higher concentrationsLiver and kidney injury may occurVapor can displace oxygen in a confined space and act as a simple asphyxiantDecomposition products at temperatures >250 degrees C include hydrogen fluoride and phosgene[CHEMINFO MSDS] Trifluorochloroethylene, stabilized (UN1082) has warning of explosive polymerization[ERG 2016] |
| DOT-Nummer und Handbuch | 1082 119P |
| Reaktive Gruppe | Halogenated Organic Compounds |
| UN-Einstufung | UN Hazard Class: 2.3UN Subsidiary Risks: 2.1 |
| Special Reports | Clayton JWToxicology of the fluoro alkenes Review and research needsEnviron Health Perspect (21): 255 (1977). Review of the toxicology of fluoroalkenes. |
| Reactivity Alerts | Highly Flammable |
| Brandbekämpfung | Excerpt from ERG Guide 119 [Gases - Toxic - Flammablepolymerization hazard]:Shut off supplyif 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. |
| Erste-Hilfe-Maßnahmen | 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. |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | Call a physician after all exposures to this compoundit is more toxic than most of the closely related propellant gases.General First Aid: |
| Sichere Lagerung | Fireproof. Cool. |
| Expositionsschutz und Persönliche Schutzausrüstung | · 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]. |
| Brandbekämpfungsverfahren | For fires involving flammable gases, the best procedure is to stop the flow of the gas before attempting extinguishment of the fire. To extinguish the fire while allowing continued flow of the gas is extremely dangerousan explosive cloud of gas/air mixture may be created that, if ignited, may cause far more damage than the original fire. Extinguishing the flame using carbon dioxide or dry chemical may be desirable to allow immediate access to valves to shut off the flow of gas, but this must be done carefully. In many cases, it will be preferable to allow continued burning, while protecting exposures with water spray, until the flow of gas can be stopped.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Trifluorochloroethylene, stabilized/Wear positive pressure self-contained breathing apparatus. /Trifluorochloroethylene, stabilized/Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-half (1/2) mile radius. /Trifluorochloroethylene, stabilized/Shut off supply ... extinguish with water spray, alcohol-resistant foam, dry powder, carbon dioxide. |
| Lagerbedingungen | Fireproof. Cool. |
| Reinigungsverfahren | Ventilation. Remove all ignition sources. Remove vapor with fine water spray. Personal protection: self-contained breathing apparatus. |
| Freisetung ohne Brand | Excerpt from ERG Guide 119 [Gases - Toxic - Flammablepolymerization hazard]: |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Verschüttetes entsorgen | Ventilation. Remove all ignition sources. Remove vapour with fine water spray. Personal protection: self-contained breathing apparatus. |
| Wechselwirkungen | 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. |
| Umweltverhalten | 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 productthe 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). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation. |
| Signs and Symptoms | Dizziness. Nausea.ON CONTACT WITH LIQUID: FROSTBITE. |
| Effluent Concentrations | Chlorotrifluoroethylene 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). |
| ICSC Environmental Data | Avoid release to the environment because of its impact on the ozone layer. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of chlorotrifluoroethylene can be estimated to be 95(SRC). According to a classification scheme(2), this estimated Koc value suggests that chlorotrifluoroethylene is expected to have high mobility in soil. Chlorotrifluoroethylene is believed to be more mobile than 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) as it is less halogenatedCFC-113 has a retardation factor of approximately 10 in a sand and gravel aquifer with an organic carbon content of 0.06%(3). |
| Artificial Pollution Sources | Chlorotrifluoroethylene's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC). The transformation of trichlorotriflurorethane (CFC-113) in the environment is believed to occur via reductive dechlorination to form 1,2-dichloro-1,2,2-trifluoroethane and then, through elimination, chlorotrifluoroethylene(2).Chlorotrifluoroethylene was found to be a biodegradation product of trichlorotrifluoroethane in an investigation of natural attenuation potential of peat and sewage sludge from a Dutch halogen-contaminated industrial site(1). In groundwater studies of the Gloucester landfill project in Ontario, Canada, trichlorotrifluoroethylene is biotransformed via reductive dechlorination to form chlorotrifluoroethylene(2). |
| Environmental Bioconcentration | An estimated BCF of 6 was calculated in fish for chlorotrifluoroethylene(SRC), using an estimated log Kow of 1.65(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for chlorotrifluoroethylene is estimated as 0.31 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that chlorotrifluoroethylene is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4 days(SRC). Chlorotrifluoroethylene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Chlorotrifluoroethylene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 4.59X10+3 mm Hg(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ 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./LABORATORY ANIMALS: Acute Exposure/ The glutathione and cysteine conjugates of the nephrotoxin chlorotrifluoroethene, S-(2-chloro-1,1,2-trifluoroethyl)glutathione (CTFG) and S-(2-chloro-1,1,2-trifluoroethyl)cysteine (CTFC), are potent nephrotoxins in male rats. Morphological changes in the kidneys were observed 1.5 hr after giving 100 umol/kg of CTFG (i.v.), and severe damage to the proximal tubules was evident 24 hr after treatmentthis dose of CTFG caused a 100-fold increase in urine glucose excretion, a 10-fold increase in urine protein excretion and a 4-fold increase in blood urea nitrogen concentrations 24 hr after administration. Administration of 50 umol/kg of CTFG or 100 umol/kg of CTFC produced similar lesions and increases in urine glucose excretion rates and blood urea nitrogen concentrations. Administration of 10 umol/kg of CTFG produced no discernable effect on the kidneys. CTFG and CTFC did not alter plasma glucose concentrations or plasma glutamate-pyruvate transaminase activities. CTFG and CTFC produced time- and dose-dependent loses of cell viability in isolated rat renal tubular cells. The toxicity of CTFG to isolated renal tubular cells was prevented by the gamma-glutamyltransferase inhibitor AT-125, and the toxicity of CTFC and CTFG to isolated cells was prevented by aminooxyacetic acid, an inhibitor of pyridoxal phosphate-dependent enzymes. Moreover, S-(2-chloro-1,1,2-trifluoroethyl)-DL-alpha-methylcysteine, which cannot be metabolized by pyridoxal phosphate-dependent enzymes, was not toxic to isolated renal tubular cells. The data presented support the hypothesis that the nephrotoxicity of chlorotrifluoroethene is due to the enzymatic formation of a glutathione conjugate, which is metabolized to the ultimate nephrotoxin by the sequential action of renal gamma-glutamyltransferase, cysteinylglycine dipeptidase and cysteine conjugate beta-lyase./LABORATORY ANIMALS: Acute Exposure/ The role of cytochrome P450 activity in the nephrotoxicity of chlorotrifluoroethylene (CTFE)... was investigated in the male rat. Hepatic cytochrome P450 1A1 and principally P450 2B1/2 were induced by beta-naphthoflavone and phenobarbital, respectively. Nephrotoxicity was evaluated by investigating urine biochemical parameters, kidney histochemistry and histopathological modifications. ... CTFE ... induces severe nephrotoxicity in rats after 4 hr of exposure to 200 ... ppm ... . Compared with controls, activity levels of gamma-glutamyltranspeptidase (gamma GT), aspartate aminotransferase (AST), alkaline phosphatase (ALP) and N-acetyl-beta-D-glucosaminidase (NAG) in 24-hr urine were increased similarly, but urinary excretion of glucose, proteins and beta2-microglobulin (beta2-m) and serum urea and creatinine levels were increased. Histopathological and histochemical examinations of kidney sections of CTFE- ...-exposed rats revealed cellular necrosis and tubular lesions 24 hr after exposure. Beta-naphthoflavone-pretreated rats were afforded some protection against the nephrotoxicity of CTFE ... . Phenobarbital ... afforded some protection against CTFE nephrotoxicity. ... Cytochrome P450 1A1 is implicated in CTFE ... metabolism and one or several cytochromes induced by phenobarbital are implicated in CTFE metabolism. The P450 cytochromes involved in CTFE ... metabolism probably constitute detoxication metabolic pathways.../LABORATORY ANIMALS: Acute Exposure/ Male Fischer-344 rats were exposed via inhalation to a sublethal concentration (395 ppm +/- 33 ppm1882 mg/cu m) of the nephrotoxin chlorotrifluoroethylene (CTFEl for 4 hr/day for 5 consecutive days. Within 1 day after the first exposure, rats exhibited diuresis, increased water intake, decreased urine osmolality, increased urinary lactic dehydrogenase activity and increased plasma creatinine and urea nitrogen. When animals were exposed repeatedly, values for these parameters declined or returned to control levels during the exposure sequence in a manner comparable to rats receiving the single exposure. By the third day post exposure, coagulative necrosis involving primarily the pars recta, but extending to the pars convoluta, of the proximal tubule was present. Regeneration was apparent by the third day of exposure, and additional necrosis was minimal despite further exposures. Daily levels of urinary inorganic fluoride, an index of chlorotrifluoroethylene metabolism, were increased to 3-6 umol/24 hr/rat during the exposure sequence which coincided with a brief elevation in serum fluoride at the end of each exposure. Adaptation to chlorotrifluoroethylene is evident either through changes in the metabolism or disposition of chlorotrifluoroethylene or from a refractive property of the regenerating tissue to chlorotrifluoroethylene.For more Non-Human Toxicity Excerpts (Complete) data for Chlorotrifluoroethylene (24 total), please visit the HSDB record page. |
| DHS Chemicals of Interest (COI) | Trifluorochloroethylene11000066.67500Flammable chemical that can be released at a facility. |
| Landesrichtlinien für Trinkwasser | (NH) NEW HAMPSHIRE 5.0 ug/L |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1082 (TRIFLUOROCHLORO- ETHYLENE, STABILIZED (REFRIGERANT GAS R 1113)) |
| Zollcode | 2903779010 |
| RTECS-Nr. | KV0525000 |
| R-Sätze (R) | 12-20/22 |
| Toxizität | LD50 oral in mouse: 268mg/kg |
| Gefahrensymbole | F+,Xn,T,F |
| hazard_note | Flammable/Toxic |
| Sicherheitshinweise (S) | 16-38 |
| Gefahrenklasse | 2.3 |
| Gefahrstoffdaten | 79-38-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Intermediate, monomer for chlorotrifluoroethylene resins.
Herstellung & Synthese
synthetische
Chlorotrifluoroethylene 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.