Просмотр кода страницы Английская Википедия:1,1,2-Trichloro-1,2,2-trifluoroethane

{{Английская Википедия/Панель перехода}}
{{chembox
| Watchedfields  = changed
| verifiedrevid  = 477201671
| ImageFileL1    = 1,1,2-Trichloro-1,2,2-trifluoroethane skeletal.svg
| ImageFileR1    = 1,1,2-Trichloro-1,2,2-trifluoroethane 3D.png
| PIN            = 1,1,2-Trichloro-1,2,2-trifluoroethane
| OtherNames     = Arklone P<br>CFC-113<br>Freon 113<br>Frigen 113 TR<br> Freon TF<br> Valclene<br> 1,1,2-trichlorotrifluoroethane
| Section1       = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6188
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0739N04X3A
| InChI = 1/C2Cl3F3/c3-1(4,6)2(5,7)8
| InChIKey = AJDIZQLSFPQPEY-UHFFFAOYAE
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 478511
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2Cl3F3/c3-1(4,6)2(5,7)8
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AJDIZQLSFPQPEY-UHFFFAOYSA-N
| CASNo=76-13-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem=6428
| SMILES = ClC(F)(F)C(Cl)(Cl)F
}}
| Section2       = {{Chembox Properties
| Formula={{chem2|CClF2CCl2F}}
| C=2|Cl=3|F=3
| Appearance=Colorless liquid
| Odor = like [[carbon tetrachloride]]<ref name=PGCH/>
| Density=1.56 g/mL
| MeltingPtC=-35
| BoilingPtC=47.7
| Solubility=170 mg/L
| VaporPressure = 285 mmHg (20 °C)<ref name=PGCH/>
| ThermalConductivity = 0.0729 W m<sup>−1</sup> K<sup>−1</sup> (300 K)<ref>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.</ref>
  }}
| Section3       = {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
| PEL = TWA 1000 ppm (7600 mg/m{{sup|3}})<ref name=PGCH>{{PGCH|0632}}</ref>
| IDLH = 2000 ppm<ref name=PGCH/>
| REL = TWA 1000 ppm (7600 mg/m{{sup|3}}) ST 1250 ppm (9500 mg/m{{sup|3}})<ref name=PGCH/> 
| LCLo = 250,000 ppm (mouse, 1.5 hr)<br/>87,000 (rat, 6 hr)<ref>{{IDLH|76131|1,1,2-Trichloro-1,2,2-trifluoroethane}}</ref>
  }}
| Section7       = {{Chembox Hazards
| GHS_ref= <ref>[https://www.fishersci.com/store/msds?partNumber=T1781&productDescription=1+1+2-TRICHLORO-1+2+2-TRIFLUOR&vendorId=VN00033897&countryCode=US&language=en Safety Data Sheet] fishersci.com</ref>
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| PPhrases = 
| HPhrases = 
|ExternalSDS = https://datasheets.scbt.com/sc-251541.pdf
|NFPA-H = 3
|NFPA-F = 0
|NFPA-R = 1
|FlashPt = 
}}
}}
'''1,1,2-Trichloro-1,2,2-trifluoroethane''', also called '''trichlorotrifluoroethane''' or '''CFC-113''', is a [[chlorofluorocarbon]]. It has the formula {{chem2|Cl2FC\sCClF2}}. This colorless, volatile liquid is a versatile solvent.<ref name=Ull>{{Ullmann|first1=Günter |last1=Siegemund|first2=Werner|last2=Schwertfeger|first3=Andrew|last3= Feiring|first4=Bruce|last4=Smart|first5=Fred |last5=Behr|first6=Herward|last6=Vogel|first7=Blaine|last7=McKusick|title=Fluorine Compounds, Organic|year=2002|doi=10.1002/14356007.a11_349}}</ref>

==Production==
CFC-113 can be prepared from [[hexachloroethane]] and [[hydrofluoric acid]]:<ref>[http://aei.pitt.edu/38825/1/A3821.pdf Social and Economic Implications of Controlling the Use of Chlorofluorocarbons in the EEC] pitt.edu</ref>
:<chem>C2Cl6  +  3HF -> CF2Cl-CFCl2 +  3HCl  </chem>
This reaction may require catalysts such as  [[antimony]], [[chromium]], [[iron]] and [[alumina]] at high temperatures.<ref>Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V11 507 (1994)</ref>

Another synthesis method uses HF on [[tetrachloroethylene]] instead.<ref>Robert D. Ashford:  Ashford's Dictionary of Industrial Chemicals , p. 1131. 2nd Edition. Wavelength Publications, 2001</ref>

==Atmospheric reactions==
[[File:CFC-113 mm.png|thumb|left|CFC-113 measured by the Advanced Global Atmospheric Gases Experiment ([http://agage.mit.edu/ AGAGE]) in the lower atmosphere ([[troposphere]]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in [[Parts-per notation|parts-per-trillion]].]]
[[File:Hats f113 global.png|thumb|left|upright=1.0|Atmospheric concentration of CFC-113 since year 1992.]]
CFC-113 is a very unreactive chlorofluorocarbon. It remains in the [[Atmosphere of Earth|atmosphere]] about 90 years,<ref>{{cite web |url=http://www.globalchange.umich.edu/globalchange2/current/lectures/climate_change/the_science.htm |title=Global Change 2: Climate Change |publisher=[[University of Michigan]] |date=January 4, 2006 |access-date=2008-05-28 |archive-url=https://web.archive.org/web/20080420150554/http://www.globalchange.umich.edu/globalchange2/current/lectures/climate_change/the_science.htm |archive-date=2008-04-20 |url-status=dead }}</ref> sufficiently long that it will cycle out of the [[troposphere]] and into the [[stratosphere]]. In the stratosphere, CFC-113 can be broken up by [[ultraviolet radiation]] (where sunlight in the 190-225&nbsp;nm (UV) range), generating chlorine radicals (Cl•), which initiate degradation of ozone requiring only a few minutes:<ref>{{cite journal | author = Molina, Mario J. | title = Role of chlorine in the stratospheric chemistry | journal = Pure and Applied Chemistry | volume = 68 | issue = 9 | pages = 1749–1756 | year = 1996 | doi=10.1351/pac199668091749| s2cid = 22107229 | doi-access = free }}</ref><ref>{{Cite web | url=http://www.ciesin.org/TG?OZ/prodcfcs.html | title=Guides &#124; SEDAC}}</ref>
:{{chem2|CClF2CCl2F → C2F3Cl2 + Cl•}}
:{{chem2|Cl• + O3 → ClO• + O2}}
This reaction is followed by:
:{{chem2|ClO• + O → Cl• + O2}}
The process regenerates Cl• to destroy more {{chem2|O3}}. The Cl• will destroy an average of 100,000 {{chem2|O3}} molecules during its atmospheric lifetime of 1–2 years. In some parts of the world, these reactions have significantly thinned the Earth's natural stratospheric ozone layer that shields the biosphere against solar UV radiation; increased UV levels at the surface can cause skin cancer or even blindness.<ref name=Columbia/>

==Uses==
CFC-113 was one of the most heavily produced CFCs. In 1989, an estimated 250,000 tons were produced.<ref name=Ull/> It has been used as a cleaning agent for electrical and electronic components.<ref name=Columbia>{{cite encyclopedia | year = 2008 | title = Chlorofluorocarbons | encyclopedia = [[Columbia Encyclopedia]] | url = http://www.encyclopedia.com/doc/1E1-chlorofl.html | access-date = 2008-05-28 }}</ref> CFC-113’s low flammability and low toxicity made it ideal for use as a cleaner for delicate electrical equipment, fabrics, and metals. It would not harm the product it was cleaning, ignite with a spark or react with other chemicals.<ref>{{Cite web|url=https://sedac.ciesin.columbia.edu/guides?OZ/prodcfcs.html|title=Guides &#124; SEDAC|website=sedac.ciesin.columbia.edu}}</ref> It was used as a [[dry-cleaning]] solvent, introduced by [[DuPont|Du Pont]] in March 1961 as "'''Valclene'''"<ref>''Coin-Op'' 1961-04: Vol 2 Iss 4 [https://archive.org/details/sim_american-coin-op_1961-04_2_4/page/61/mode/1up P. 61] </ref>and was also marketed as the "solvent of the future" by [[Imperial Chemical Industries]] in the 1970s under the tradename ''Arklone''. Others from this series were ''Perklone'' ([[Tetrachloroethylene]]), ''Triklone'' ([[Trichloroethylene]]), ''Methoklone'' ([[Dichloromethane]]) and ''Genklene'' ([[1,1,1-Trichloroethane]]).<ref>Industrial Finishing and Surface Coatings. (1973). UK: Wheatland journals, Limited.</ref><ref>Morrison, R. D., Murphy, B. L. (2013). Chlorinated Solvents: A Forensic Evaluation. Royal Society of Chemistry</ref>

CFC-113 is one of the three most popular CFCs, along with CFC-11 and CFC-12.<ref>{{cite book | last = Zumdahl | first = Steven | title = Chemical Principles | publisher = [[D. C. Heath and Company|D. C. Heath]] | location = [[Lexington, Massachusetts|Lexington]] | year = 1995 | isbn = 978-0-669-39321-7 | url-access = registration | url = https://archive.org/details/chemicalprincip100zumd }}</ref>



CFC-113 in laboratory analytics has been replaced by other solvents.<ref>{{Cite web |url=http://www.norden.org/pub/ebook/2003-516.pdf |title=Use of Ozone Depleting Substances in Laboratories. TemaNord 516/2003 |access-date=2008-05-06 |archive-url=https://web.archive.org/web/20080227052412/http://www.norden.org/pub/ebook/2003-516.pdf |archive-date=2008-02-27 |url-status=dead }}</ref>

Reduction of CFC-113 with zinc gives [[chlorotrifluoroethylene]]:<ref name=Ull/>
:{{chem2|CFCl2\sCClF2 + Zn → CClF\dCF2 + ZnCl2}}

==Dangers==
Aside from its immense environmental impacts, Freon 113, like most chlorofluoroalkanes, forms phosgene gas when exposed to a naked flame.<ref>{{cite web |title=False Alarms: The Legacy of Phosgene Gas |url=https://hvacrschool.com/phosgene-gas/ |website=HVAC School |access-date=9 May 2022}}</ref>

==See also==
*[[1,1,1-Trichloro-2,2,2-trifluoroethane]]

==References==
{{reflist}}
{{Fluorine compounds}}

{{DEFAULTSORT:Trichloro-1, 2, 2-trifluoroethane, 1, 1, 2-}}
[[Category:Organofluorides]]
[[Category:Chlorofluorocarbons]]
[[Category:Greenhouse gases]]
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