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Chlorotrifluoroethylene

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Name

Chlorotrifluoroethylene

EINECS 201-201-8
CAS No. 79-38-9 Density 1.411 g/cm3
PSA 0.00000 LogP 2.26030
Solubility 380mg/L at 28℃ Melting Point -158 °C(lit.)
Formula C2ClF3 Boiling Point -28 °C
Molecular Weight 116.47 Flash Point -28°C
Transport Information UN 1082 Appearance colorless gas with a faint ethereal odor
Safety 16-38 Risk Codes 12-20/22
Molecular Structure Molecular Structure of 79-38-9 (Chlorotrifluoroethylene) Hazard Symbols HighlyF+,HarmfulXn,ToxicT,FlammableF
Synonyms

Ethylene, chlorotrifluoro- (8CI);1-Chloro-1,2,2-trifluoroethene;2-Chloro-1,1,2-trifluoroethylene;CFC 1113;Chlorotrifluoroethene;F 1113;Genetron 1113;Monochlorotrifluoroethylene;R 1113;Trifluoromonochloroethylene;Trifluorovinyl chloride;Trithene;Ethene,chlorotrifluoro- (9CI);

Article Data 93

Chlorotrifluoroethylene Synthetic route

76-13-1

1,1,2-Trichloro-1,2,2-trifluoroethane

79-38-9

Chlorotrifluoroethylene

Conditions
ConditionsYield
With potassium zinc trihydride at 250 - 320℃; under 7500.75 Torr; for 5h; Temperature; Pressure; Inert atmosphere; Large scale;99.22%
With ammonium chloride; zinc(II) chloride In methanol; water electrochemical process;90%
With zinc(II) chloride; zinc In ethanol at 50℃; for 3h; Dehalogenation;75%
76-13-1

1,1,2-Trichloro-1,2,2-trifluoroethane

A

354-23-4

1,2-dichloro-1,2,2-trifluoroethane

B

79-38-9

Chlorotrifluoroethylene

C

359-11-5

1,1,2-trifluoroethylene

Conditions
ConditionsYield
With hydrogen; silica gel; nickel at 450℃; under 760 Torr; Title compound not separated from byproducts;A n/a
B 95.8%
C n/a
bismuth(III) chloride; silica gel; palladium at 250℃; Yield given. Yields of byproduct given;
With hydrogen; silica gel; nickel at 450℃; under 760 Torr; Product distribution; other supported Ni catalysts and metal oxides;
bismuth(III) chloride; silica gel; palladium at 250℃; under 760 Torr; Product distribution; other catalysts and modifier; variation of condition: selectivity;
354-61-0

1,2-dichloro-1,2,2-trifluoro-1-iodoethane

79-38-9

Chlorotrifluoroethylene

Conditions
ConditionsYield
With zinc In dichloromethane; ethyl acetate at 0 - 20℃; for 2h;93%
With hexaethylphosphoric triamide In benzonitrile ice-salt bath;92%
With 1,4-dioxane; zinc
With zinc In dichloromethane; acetic anhydride for 3h; Ambient temperature;
374-48-1

(2-chloro tetrafluoro ethyl) trichloro silane

79-38-9

Chlorotrifluoroethylene

Conditions
ConditionsYield
In neat (no solvent) byproducts: SiFCl3, SiF2Cl2, SiFCl3; pyrolysis at 220°C, 15 hours;;90%
In neat (no solvent) byproducts: SiFCl3, SiF2Cl2, SiFCl3; pyrolysis at 220°C, 15 hours;;90%
at 220℃;
662-06-6

(2,2-dichloro trifluoro ethyl) trichloro silane

A

79-38-9

Chlorotrifluoroethylene

B

1842-05-3

1,1-dichloro-1,2-difluoroethane

Conditions
ConditionsYield
With sodium hydroxide; water hydrolysis at 25°C, 30 minutes;;A 13%
B 87%
With NaOH; H2O hydrolysis at 25°C, 30 minutes;;A 13%
B 87%
2106-94-7

1-bromo-1,2-dichloro-1,2,2-trifluoro-ethane

79-38-9

Chlorotrifluoroethylene

Conditions
ConditionsYield
With hexaethylphosphoric triamide In benzonitrile other perhalogenated alkanes;80%
With hexaethylphosphoric triamide In benzonitrile ice-salt bath;80%
354-51-8

1,2-dibromo-1-chloro-1,2,2-trifluoroethane

79-38-9

Chlorotrifluoroethylene

Conditions
ConditionsYield
With hexaethylphosphoric triamide In benzonitrile ice-salt bath;78%
354-61-0

1,2-dichloro-1,2,2-trifluoro-1-iodoethane

677-69-0

perfluoroisopropyl iodide

A

431-89-0

1,1,1,2,3,3,3-Heptafluoropropane

B

79-38-9

Chlorotrifluoroethylene

C

354-96-1

perfluoro(2,3-dimethylbutane)

D

375-45-1

perfluoro-1,2,3,4-tetrachlorobutane

Conditions
ConditionsYield
With acetic anhydride; zinc In dichloromethane at 40℃;A n/a
B n/a
C 47%
D 47%
354-61-0

1,2-dichloro-1,2,2-trifluoro-1-iodoethane

677-69-0

perfluoroisopropyl iodide

A

431-89-0

1,1,1,2,3,3,3-Heptafluoropropane

B

79-38-9

Chlorotrifluoroethylene

C

354-96-1

perfluoro(2,3-dimethylbutane)

D

375-45-1

perfluoro-1,2,3,4-tetrachlorobutane

E

1173181-83-3

C5Cl2F10

Conditions
ConditionsYield
With acetic anhydride; zinc In dichloromethane at 40℃;A n/a
B n/a
C 27%
D 28%
E 40%
With acetic anhydride; zinc In dichloromethane at 50℃;A n/a
B n/a
C 31%
D 32%
E 30%
13709-36-9

xenon difluoride

726203-09-4

1-chlorodifluoroethenyldifluoroborane

A

76-15-3

Chloropentafluoroethane

B

79-38-9

Chlorotrifluoroethylene

C

726203-15-2

1-chloro-2,2-difluoroethenylxenon(II) tetrafluoroborate

D

7637-07-2

boron trifluoride

Conditions
ConditionsYield
In further solvent(s) soln. of CF2=CClBF2 in 1,1,1,3,3-pentafluoropropane cooled to -65°C and XeF2 added in small portions within 6 min; stirring stopped after2 h; mother liquor decanted; precipitate separated and dried in vacuum at -60°C;A n/a
B n/a
C 19%
D n/a

Chlorotrifluoroethylene Consensus Reports

Reported in EPA TSCA Inventory.

Chlorotrifluoroethylene Standards and Recommendations

DOT Classification:  2.1; Label: Flammable Gas

Chlorotrifluoroethylene Specification

The IUPAC name of Chlorotrifluoroethylene is 1-chloro-1,2,2-trifluoroethene. With the CAS registry number 79-38-9, it is also named as  1,1,2-Trifluoro-2-chloroethylene. The product's categorie is refrigerant. It is a colorless gas with a faint ethereal odor. And it is shipped as a liquefied gas under its vapor pressure. Additionally, Chlorotrifluoroethylene is highly toxic. And under prolonged exposure to intense heat or fire, the containers may violently rupture and rocket, or the material may polymerize with possible container rupture.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.16; (4)ACD/LogD (pH 7.4): 2.16; (5)ACD/BCF (pH 5.5): 25.96; (6)ACD/BCF (pH 7.4): 25.96; (7)ACD/KOC (pH 5.5): 358.05; (8)ACD/KOC (pH 7.4): 358.05; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)Index of Refraction: 1.32; (12)Molar Refractivity: 16.39 cm3; (13)Molar Volume: 82.4 cm3; (14)Polarizability: 6.5×10-24 cm3; (15)Surface Tension: 13.5 dyne/cm; (16)Enthalpy of Vaporization: 21.99 kJ/mol; (17)Vapour Pressure: 3940 mmHg at 25°C; (18)Exact Mass: 115.964062; (19)MonoIsotopic Mass: 115.964062; (20)Heavy Atom Count: 6; (21)Complexity: 72.9.

Preparation of Chlorotrifluoroethylene: It is derived from the dechlorination of trifluorotrichloroethane. Generally, using zinc powder as dechlorination agent and methanol as solvent. The reaction temperature is 50-150 °C, the reaction pressure is 2.08MPa, and the reaction time is 3-4s. Consumption of raw materials is fixed: trifluorotrichloroethane 1830 kg / t, methanol (> 95%) 1080kg / t, zinc (> 95%) 840kg / t.

Uses of Chlorotrifluoroethylene: It can be polymerised to produce the plastic ECTFE. And it is used as raw material of fluorine plastic, fluorine rubber, refrigerant, CFCs oil and halothane anesthetic. Additionally, it reacts methanol to get (2-chloro-1,1,2-trifluoro-ethyl)-methyl ether. This reaction needs reagent KOH-solution at temperature of -80 °C.

 

When you are using this chemical, please be cautious about it as the following:
It is extremely flammable, so people should keep it away from sources of ignition. And it is harmful by inhalation and if swallowed. Inhalation causes dizziness, nausea, vomiting; liver and kidney injury may develop after several hours and cause jaundice and necrosis of the kidney. In case of insufficient ventilation, wear suitable respiratory equipment.

People can use the following data to convert to the molecule structure.
1. SMILES:F/C(F)=C(/Cl)F
2. InChI:InChI=1/C2ClF3/c3-1(4)2(5)6
3. InChIKey:UUAGAQFQZIEFAH-UHFFFAOYAH

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC50 inhalation 4300mg/m3/4H (4300mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(5), Pg. 36, 1977.
mouse LC50 inhalation 3000ppm/7H (3000ppm)   Acta Biologica et Medica Germanica. Vol. 21, Pg. 377, 1968.
mouse LD50 intraperitoneal 175mg/kg (175mg/kg)   Acta Biologica et Medica Germanica. Vol. 21, Pg. 377, 1968.
mouse LD50 oral 268mg/kg (268mg/kg)   Acta Biologica et Medica Germanica. Vol. 21, Pg. 377, 1968.
rat LC50 inhalation 1000ppm/4H (1000ppm) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

GASTROINTESTINAL: OTHER CHANGES
Fluorine Chemistry Reviews. Vol. 1, Pg. 197, 1967.

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