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

From Wikipedia, the free encyclopedia
1,1,2-Trichloro-1,2,2-trifluoroethane
Names
Preferred IUPAC name
1,1,2-Trichloro-1,2,2-trifluoroethane
Other names
Arklone P
CFC-113
Freon 113
Frigen 113 TR
Freon TF
Valclene
1,1,2-trichlorotrifluoroethane
TCTFE
Solvent 113
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.000.852Edit this at Wikidata
UNII
  • InChI=1S/C2Cl3F3/c3-1(4,6)2(5,7)8 checkY
    Key: AJDIZQLSFPQPEY-UHFFFAOYSA-N checkY
  • InChI=1/C2Cl3F3/c3-1(4,6)2(5,7)8
    Key: AJDIZQLSFPQPEY-UHFFFAOYAE
  • ClC(F)(F)C(Cl)(Cl)F
Properties
CClF2CCl2F
Molar mass187.37 g·mol−1
AppearanceColorless liquid
Odorlikecarbon tetrachloride[1]
Density1.56 g/mL
Melting point−35 °C (−31 °F; 238 K)
Boiling point47.7 °C (117.9 °F; 320.8 K)
170 mg/L
Vapor pressure285 mmHg (20 °C)[1]
Thermal conductivity0.0729 W m−1 K−1 (300 K)[2]
Hazards
Lethal dose or concentration (LD, LC):
250,000 ppm (mouse, 1.5 hr)
87,000 (rat, 6 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1000 ppm (7600 mg/m3)[1]
REL (Recommended)
TWA 1000 ppm (7600 mg/m3) ST 1250 ppm (9500 mg/m3)[1]
IDLH (Immediate danger)
2000 ppm[1]
Hazards
GHS labelling:[4]
GHS07: Exclamation markGHS09: Environmental hazard
Warning
NFPA 704 (fire diamond)
Safety data sheet (SDS)https://datasheets.scbt.com/sc-251541.pdf
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

1,1,2-Trichloro-1,2,2-trifluoroethane, also called simplytrichlorotrifluoroethane (often abbreviated asTCTFE) orCFC-113, is achlorofluorocarbon. It has the formulaCl2FC−CClF2. This colorless, volatile liquid was a versatile solvent[5] used in various precise cleaning operations until it was phased out due its impact on the ozone layer.

Production

[edit]

CFC-113 can be prepared fromhexachloroethane andhydrofluoric acid:[6]

C2Cl6 + 3 HF → CF2Cl−CFCl2 + 3 HCl

This reaction may require catalysts such asantimony,chromium,iron andalumina at high temperatures.[7]

Another synthesis method uses HF ontetrachloroethylene instead.[8] Industrial production of CFC-113 began in the early 1940s.[9]

Uses

[edit]

CFC-113 was one of the three most popular CFCs, along withCFC-11 andCFC-12.[10] In 1989, an estimated 250,000 tons were produced.[5] It has been used as a cleaning agent for electrical and electronic components.[11] CFC-113’s low flammability and low toxicity made it ideal for use as a cleaner for delicate electrical-electronic equipment such asprinted circuit boards, fabrics, and metals. It would not harm the product it was cleaning, ignite with a spark or react with other chemicals.[12]

It was used as adry-cleaning solvent, as an alternative to perchloroethylene, introduced byDuPont in March 1961 as "Valclene"[13] (former designated trade name was "Fasclene"[14] but it was later changed toValclene in the same year for legal reasons)[15][16] and was also marketed as the "solvent of the future" byImperial Chemical Industries in the 1970s under the tradename "Arklone". Others from this series werePerklone (Tetrachloroethylene),Triklone (Trichloroethylene),Methoklone (Dichloromethane) andGenklene (1,1,1-Trichloroethane).[17][18] Its use in dry-cleaning peaked around 1971, and dry-cleaners using CFC-113 were known asValclenerías in Spanish.[19] In 1986, 489 dry-cleaning facilities (about 2.2% of 21,787 dry-cleaning facilities) in the US were using CFC-113 as their main solvent.[20] It was seen as the perfect dry-cleaning solvent until its environmental effects were discovered.

CFC-113 in laboratory analytics and industry has been replaced by other solvents.[21]

Reduction of CFC-113 with zinc giveschlorotrifluoroethylene:[5]

CFCl2−CClF2 + Zn → CClF=CF2 + ZnCl2

Hazards

[edit]

When inhaled in large concentrations, trichlorotrifluoroethane can cause loss of consciousness.

CFC-113 measured by the Advanced Global Atmospheric Gases Experiment (AGAGE) in the lower atmosphere (troposphere) at stations around the world. Abundances are given as pollution free monthly mean mole fractions inparts-per-trillion.
Atmospheric concentration of CFC-113 since year 1992.

CFC-113 is a very unreactive chlorofluorocarbon. It may remain in theatmosphere up to 90 years,[22] sufficiently long that it will cycle out of thetroposphere and into thestratosphere. In the stratosphere, CFC-113 can be broken up byultraviolet radiation (UV, sunlight in the 190-225 nm range), generating chlorine radicals (Cl•), which initiate degradation of ozone requiring only a few minutes:[23][24]

CClF2CCl2F → C2F3Cl2 + Cl•
Cl• + O3 → ClO• + O2

This reaction is followed by:

ClO• + O → Cl• + O2

The process regenerates Cl• to destroy moreO3. The Cl• will destroy an average of 100,000O3 molecules during its atmospheric lifetime of 1–2 years.[11]

Aside from its immense environmental impacts, trichlorotrifluoroethane, like most chlorofluoroalkanes, formsphosgene gas when exposed to a naked flame.[25]

See also

[edit]

References

[edit]
  1. ^abcdeNIOSH Pocket Guide to Chemical Hazards."#0632".National Institute for Occupational Safety and Health (NIOSH).
  2. ^Touloukian, Y.S., Liley, P.E., and Saxena, S.C. Thermophysical properties of matter - the TPRC data series. Volume 3. Thermal conductivity - nonmetallic liquids and gases. Data book. 1970.
  3. ^"1,1,2-Trichloro-1,2,2-trifluoroethane".Immediately Dangerous to Life or Health Concentrations.National Institute for Occupational Safety and Health.
  4. ^Safety Data Sheet fishersci.com
  5. ^abcSiegemund, Günter; Schwertfeger, Werner; Feiring, Andrew; Smart, Bruce; Behr, Fred; Vogel, Herward; McKusick, Blaine (2002). "Fluorine Compounds, Organic".Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.doi:10.1002/14356007.a11_349.ISBN 978-3-527-30673-2.
  6. ^Social and Economic Implications of Controlling the Use of Chlorofluorocarbons in the EEC pitt.edu
  7. ^Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V11 507 (1994)
  8. ^Robert D. Ashford: Ashford's Dictionary of Industrial Chemicals, p. 1131. 2nd Edition. Wavelength Publications, 2001
  9. ^Use and application of CFC-11, CFC-12, CFC-113 and SF6 as environmental tracers of groundwater residence time: A review Geoscience Frontiers Volume 10, Issue 5, September 2019, Pages 1643-1652; L.A. Chambers, D.C. Gooddy, A.M. Binley
  10. ^Zumdahl, Steven (1995).Chemical Principles.Lexington:D. C. Heath.ISBN 978-0-669-39321-7.
  11. ^ab"Chlorofluorocarbons".Columbia Encyclopedia. 2008. Retrieved2008-05-28.
  12. ^"Guides | SEDAC".sedac.ciesin.columbia.edu.
  13. ^Coin-Op 1961-04: Vol 2 Iss 4P. 61
  14. ^Fast Dry Cleaner Ready - New York Times (March 27, 1961)
  15. ^DuPont Fluid Renamed - Oil, Paint and Drug Reporter Vol 179 Iss 14 page 60
  16. ^Perchloroethylene Cleaner: It Will Not Cleaned Out - Oil, Paint and Drug Reporter 1961-04-24: Vol 179 Iss 17 page 5
  17. ^Industrial Finishing and Surface Coatings. (1973). UK: Wheatland journals, Limited.
  18. ^Morrison, R. D., Murphy, B. L. (2013). Chlorinated Solvents: A Forensic Evaluation. Royal Society of Chemistry
  19. ^En busca del disolvente perfecto (In the search of the perfect solvent) - La Tintoteria (2010) page 14
  20. ^A Chronology of Historical Developments in Drycleaning (November 2007)
  21. ^"Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003"(PDF). Archived fromthe original(PDF) on 2008-02-27. Retrieved2008-05-06.
  22. ^"Global Change 2: Climate Change".University of Michigan. January 4, 2006. Archived fromthe original on 2008-04-20. Retrieved2008-05-28.
  23. ^Molina, Mario J. (1996)."Role of chlorine in the stratospheric chemistry".Pure and Applied Chemistry.68 (9):1749–1756.doi:10.1351/pac199668091749.S2CID 22107229.
  24. ^"Guides | SEDAC".
  25. ^"False Alarms: The Legacy of Phosgene Gas".HVAC School. Retrieved9 May 2022.
Salts and covalent derivatives of thefluoride ion
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LiFBeF2BF
BF3
B2F4
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CF4
CxFy
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NF3
FN3
N2F2
NF
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NF2
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+NO3
OF2
O2F2
OF
O3F2
O4F2
?OF4
F2Ne
NaFMgF2AlF
AlF3
SiF4P2F4
PF3
PF5
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S2F2
SF2
S2F4
SF3
SF4
S2F10
SF6
+SO4
ClF
ClF3
ClF5
?ArF2
?ArF4
KFCaF
CaF2
ScF3TiF2
TiF3
TiF4
VF2
VF3
VF4
VF5
CrF2
CrF3
CrF4
CrF5
?CrF6
MnF2
MnF3
MnF4
?MnF5
FeF2
FeF3
FeF4
CoF2
CoF3
CoF4
NiF2
NiF3
NiF4
CuF
CuF2
?CuF3
ZnF2GaF2
GaF3
GeF2
GeF4
AsF3
AsF5
Se2F2
SeF4
SeF6
+SeO3
BrF
BrF3
BrF5
KrF2
?KrF4
?KrF6
RbFSrF
SrF2
YF3ZrF2
ZrF3
ZrF4
NbF4
NbF5
MoF4
MoF5
MoF6
TcF4
TcF
5

TcF6
RuF3
RuF
4

RuF5
RuF6
RhF3
RhF4
RhF5
RhF6
PdF2
Pd[PdF6]
PdF4
?PdF6
Ag2F
AgF
AgF2
AgF3
CdF2InF
InF3
SnF2
SnF4
SbF3
SbF5
TeF4
?Te2F10
TeF6
+TeO3
IF
IF3
IF5
IF7
+IO3
XeF2
XeF4
XeF6
?XeF8
CsFBaF2 LuF3HfF4TaF5WF4
WF5
WF6
ReF4
ReF5
ReF6
ReF7
OsF4
OsF5
OsF6
?OsF
7

?OsF
8
IrF2
IrF3
IrF4
IrF5
IrF6
PtF2
Pt[PtF6]
PtF4
PtF5
PtF6
AuF
AuF3
Au2F10
?AuF6
AuF5•F2
Hg2F2
HgF2
?HgF4
TlF
TlF3
PbF2
PbF4
BiF3
BiF5
PoF2
PoF4
PoF6
AtF
?AtF3
?AtF5
RnF2
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6
FrFRaF2 LrF3RfDbSgBhHsMtDsRgCnNhFlMcLvTsOg
LaF3CeF3
CeF4
PrF3
PrF4
NdF2
NdF3
NdF4
PmF3SmF
SmF2
SmF3
EuF2
EuF3
GdF3TbF3
TbF4
DyF2
DyF3
DyF4
HoF3ErF3TmF2
TmF3
YbF2
YbF3
AcF3ThF2
ThF3
ThF4
PaF4
PaF5
UF3
UF4
UF5
UF6
NpF3
NpF4
NpF5
NpF6
PuF3
PuF4
PuF5
PuF6
AmF2
AmF3
AmF4
?AmF6
CmF3
CmF4
 ?CmF6
BkF3
BkF
4
CfF3
CfF4
EsF3
EsF4
?EsF6
FmMdF3No
PF6,AsF6,SbF6 compounds
AlF2−5,AlF3−6 compounds
chlorides, bromides, iodides
and pseudohalogenides
SiF2−6,GeF2−6 compounds
Oxyfluorides
Organofluorides
with transition metal,
lanthanide, actinide, ammonium
nitric acids
bifluorides
thionyl, phosphoryl,
and iodosyl
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