基本情報
- 標準SMILES
FC(F)=C(F)Cl- InChIKey
UUAGAQFQZIEFAH-UHFFFAOYSA-N- 分子式
- C2ClF3
- 平均分子量
- 116.47 g/mol
- 単同位体質量
- 115.96406234
概要
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.
名称と識別子
- 優先名称
- Chlorotrifluoroethylene
- IUPAC
- 1-chloro-1,2,2-trifluoroethene
- 現地名
- 1,1,2-トリフルオロ-2-クロロエテン
- 英語名
- Chlorotrifluoroethylene
- 分子式
- C2ClF3
- 分子量
- 116.47
名称と別名
名称をさらに表示
データベース識別子
- CAS
79-38-9- PubChem CID
- 6594
- DTXSID
DTXSID3026485- UNII
- AF215GW34G
- EC Number
- 201-201-8
- Nikkaji
- J35.200D
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
- 3
- 回転可能結合数
- 0
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 72.9
実験および物理化学的性質
Chemical Classes
Toxic Gases & Vapors -> Other Toxic Gases & Vapors
Flammable agents - 4th degree
PFAS
PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
PFAS -> Other/unspecified
PFAS -> Fluoropolymers
PFAS -> Other/unspecified
Density
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
Boiling Point
-18 °F at 760 mmHg (USCG, 1999)
-18 °F
-27.8 °C
-28 °C
-27.8 °C @760 [mm Hg]
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.
Melting Point
-158.2 °C
-158 °C
-158.2 °C
物理化学的性質
- 融点
- 158 °C · −158 °C(lit.)
- 沸点
- 28.4 °C · −28.4 °C(lit.)
- 比重(密度)
- 1 · 1,305 g/cm3
- 蒸気密度
- 4.13 · 4.13 (vs air)
- 蒸気圧
- 612 kPa · 612kPa at 25℃
- 屈折率
- 1.38 · 1.3800
- 闪点
- -28 °C · -28°C
- 水溶解度
- 380 mg/L · 380mg/L at 28℃
- 比熱容量
- 0.72 J/ · Cp(gas): 0.72 J/(g·K), at 25℃
- Henry's Law Constant
- 3.2 · 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
- 1.65 · 1.65
- CAS データベース
- 79 · 79-38-9(CAS DataBase Reference)
- NISTの化学物質情報
- Ethene, chlorotrifluoro-(79-38-9)
- EPAの化学物質情報
- Chlorotrifluoroethylene (79-38-9)
化学的性質
化学的特性Colorless gas; faint ethereal odor. Decomposes in water.
安全と法規制
GHS分類
GHS Classification
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]
危険有害性情報
Hazards Identification
Toxic/poison by inhalation (TIH/PIH)
Toxic/poison by inhalation (TIH/PIH)
Regulatory Information
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.)
Fire Hazards
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.
Health Hazards
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.
Hazards Summary
Can cause frostbite; Inhalation can result in dizziness and nausea at lower concentrations and cardiac sensitization and CNS depression at higher concentrations; Liver and kidney injury may occur; Vapor can displace oxygen in a confined space and act as a simple asphyxiant; Decomposition products at temperatures >250 degrees C include hydrogen fluoride and phosgene; [CHEMINFO MSDS] Trifluorochloroethylene, stabilized (UN1082) has warning of explosive polymerization; [ERG 2016]
DOT ID and Guide
1082 119P
1082 119P
安全と保護具
Fire Fighting
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
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
· 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
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:
Exposure Control and Personal Protection
· 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].
Fire Fighting Procedures
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 dangerous; an 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.
Disposal Methods
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.
毒性情報
Interactions
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
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).
Signs and Symptoms
Dizziness. Nausea.
ON CONTACT WITH LIQUID: FROSTBITE.
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 halogenated; CFC-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 treatment; this 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 ppm; 1882 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.
法規制情報
DHS Chemicals of Interest (COI)
Trifluorochloroethylene
1
10000
66.67
500
Flammable chemical that can be released at a facility.
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- KV0525000
- ridadr
- UN 1082 (TRIFLUOROCHLORO- ETHYLENE, STABILIZED (REFRIGERANT GAS R 1113))
- 毒性
- LD50 oral in mouse: 268mg/kg
- hs_code
- 2903779010
- risk_code
- 12-20/22
- hazard_code
- F+,Xn,T,F
- hazard_note
- Flammable/Toxic
- safety_code
- 16-38
- hazard_class
- 2.3
- 有毒物質データの
- 79-38-9(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
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
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.
用途と製造
Uses
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.
U.S. Production
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.
Methods of Manufacturing
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.
General Manufacturing Information
Plastics Material and Resin Manufacturing
Ethene, 1-chloro-1,2,2-trifluoro-: ACTIVE
Selection of plastic films for food packaging.
1,1,2-TRIFLUORO-1-BROMO-2-CHLOROETHANE WAS DEHYDROBROMINATED TO FORM TOXIC TRIFLUOROCHLOROETHYLENE WHEN THE FLUOROCARBON ANESTHETIC WAS USED IN CONJUNCTION WITH SODA LIME IN ANESTHESIA.
応用分野
解説1-クロロ-1,2,2-トリフルオロエテン.1,2-ジクロロ-1,1,2-トリフルオロエタンの脱塩化水素,あるいはトリクロロトリフルオロエタンの亜鉛または水素による脱塩素により製造する.融点-168.1 ℃,沸点-27.9 ℃.臨界温度105.8 ℃.臨界圧41.4 kg cm-2.燃焼範囲16~34体積%(空気中).レドックス触媒法やエマルション重合による高重合体は,形成加工性がテフロンよりすぐれたフッ素樹脂として有用であり,エテンとの共重合体は,耐熱,耐衝撃性にすぐれている.低重合体は,潤滑油,グリースとして用いられる.取り扱いには耐爆設備を使用する.
用途レドックス触媒法エマルジョン重合による高重合体は成形加工性がテフロンよりすぐれたフッ素樹脂として有用、低重合体は潤滑油、グリース、ワックスとして用いられる。エチレンとの交互共重合体は耐熱、耐ストレスクラッキング性、耐衝撃性がすぐれたフッ素樹脂となる。
使用Intermediate, monomer for chlorotrifluoroethylene resins.
一般的な説明Chlorotrifluoroethylene is a colorless gas with a faint ethereal odor. Chlorotrifluoroethylene is shipped as a liquefied gas under its vapor pressure. Chlorotrifluoroethylene 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.
調製方法
製造方法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.
純化方法Scrub it with 10% KOH solution, then 10% H2SO4 solution to remove inhibitors, dry and pass it through silica gel. It is stabilized with ~1% tributylamine. Use brass equipment. [Beilstein 1 III 646.] TOXIC GAS.
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