Trichlorofluoromethane

Last updated
Trichlorofluoromethane
Trichlorofluoromethane-2D.svg
Trichlorofluoromethane-3D-vdW.png
Names
Preferred IUPAC name
Trichloro(fluoro)methane
Other names
Trichlorofluoromethane
Fluorotrichloromethane
Fluorochloroform
Freon 11
CFC 11
R 11
Arcton 9
Freon 11A
Freon 11B
Freon HE
Freon MF
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.812 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-892-3
PubChem CID
RTECS number
  • PB6125000
UNII
  • InChI=1S/CCl3F/c2-1(3,4)5 Yes check.svgY
    Key: CYRMSUTZVYGINF-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CCl3F/c2-1(3,4)5
  • C(F)(Cl)(Cl)Cl
  • ClC(Cl)(Cl)F
Properties
CCl3F
Molar mass 137.36 g·mol−1
AppearanceColorless liquid/gas
Odor nearly odorless [1]
Density 1.494 g/cm3
Melting point −110.48 °C (−166.86 °F; 162.67 K)
Boiling point 23.77 °C (74.79 °F; 296.92 K)
1.1 g/L (at 20 °C)
log P 2.53
Vapor pressure 89 kPa at 20 °C
131 kPa at 30 °C
Thermal conductivity 0.0079 W m−1 K−1 (gas at 300 K, ignoring pressure dependence) [2] [ verification needed ]
Hazards
GHS labelling: [3]
GHS-pictogram-exclam.svg
Warning
H420
P502
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
26,200 ppm (rat, 4 hr)
100,000 ppm (rat, 20 min)
100,000 ppm (rat, 2 hr) [4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1000 ppm (5600 mg/m3) [1]
REL (Recommended)
C 1000 ppm (5600 mg/m3) [1]
IDLH (Immediate danger)
2000 ppm [1]
Safety data sheet (SDS) ICSC 0047
Supplementary data page
Trichlorofluoromethane (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Trichlorofluoromethane, also called freon-11, CFC-11, or R-11, is a chlorofluorocarbon (CFC). It is a colorless, faintly ethereal, and sweetish-smelling liquid that boils around room temperature. [5] CFC-11 is a Class 1 ozone-depleting substance which damages Earth's protective stratospheric ozone layer. [6] R-11 is not flammable at ambient temperature and pressure but it can become very combustible if heated and ignited by a strong ignition source.

Contents

Historical use

Trichlorofluoromethane was first widely used as a refrigerant. Because of its high boiling point compared to most refrigerants, it can be used in systems with a low operating pressure, making the mechanical design of such systems less demanding than that of higher-pressure refrigerants R-12 or R-22.

Trichlorofluoromethane is used as a reference compound for fluorine-19 NMR studies.

Trichlorofluoromethane was formerly used in the drinking bird novelty, largely because it has a boiling point of 23.77 °C (74.79 °F). The replacement, dichloromethane, boiling point 39.6 °C (103.3 °F), requires a higher ambient temperature to work.

Prior to the knowledge of the ozone depletion potential of chlorine in refrigerants and other possible harmful effects on the environment, trichlorofluoromethane was sometimes used as a cleaning/rinsing agent for low-pressure systems. [7]

Production

Trichlorofluoromethane can be obtained by reacting carbon tetrachloride with hydrogen fluoride at 435 °C and 70 atm, producing a mixture of trichlorofluoromethane, tetrafluoromethane and dichlorodifluoromethane in a ratio of 77:18:5. The reaction can also be carried out in the presence of antimony(III) chloride or antimony(V) chloride: [8]

CCl4 + HF → CCl3F + CF4 + CCl2F2

Trichlorofluoromethane is also formed as one of the byproducts when graphite reacts with chlorine and hydrogen fluoride at 500 °C. [8]

Sodium hexafluorosilicate under pressure at 270 °C, titanium(IV) fluoride, chlorine trifluoride, cobalt(III) fluoride, iodine pentafluoride, and bromine trifluoride are also suitable fluorinating agents for carbon tetrachloride. [8] [9]

CCl4 + Na2SiF6 → CCl3F + CCl2F2 + CCl3F + NaCl + SiF4
CCl4 + BrF3 → BrF + CCl2F2 + CCl3F

Trichlorofluoromethane was included in the production moratorium in the Montreal Protocol of 1987. It is assigned an ozone depletion potential of 1.0, and U.S. production was ended on January 1, 1996. [6]

Regulatory challenges

In 2018, the atmospheric concentration of CFC-11 was noted by researchers to be declining more slowly than expected, [10] [11] and it subsequently emerged that it remains in widespread use as a blowing agent for polyurethane foam insulation in the construction industry of China. [12] In 2021, researchers announced that emissions declined by 20,000 U.S. tons from 2018 to 2019, which mostly reversed the previous spike in emissions. [13] In 2022, the European Commission announced an updated regulation that mandates the recovery and prevention of emissions of CFC-11 blowing agents from foam insulation in demolition waste, which is still emitted at significant scale. [14]

Dangers

R11, like most chlorofluorocarbons, forms phosgene gas when exposed to a naked flame. [15]

Use in Planetary Astrophysics

Because trichlorofluoromethane is one of the easiest to detect chlorofluorocarbons produced by anthropogenic activity, it is has been used in attempting to detect industrial pollution in the atmospheres of earth-like exoplanets. [16]

See also

Related Research Articles

<span class="mw-page-title-main">Ozone depletion</span> Atmospheric phenomenon

Ozone depletion consists of two related events observed since the late 1970s: a steady lowering of about four percent in the total amount of ozone in Earth's atmosphere, and a much larger springtime decrease in stratospheric ozone around Earth's polar regions. The latter phenomenon is referred to as the ozone hole. There are also springtime polar tropospheric ozone depletion events in addition to these stratospheric events.

<span class="mw-page-title-main">Chlorofluorocarbon</span> Class of organic compounds

Chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) are fully or partly halogenated hydrocarbons that contain carbon (C), hydrogen (H), chlorine (Cl), and fluorine (F), produced as volatile derivatives of methane, ethane, and propane.

<span class="mw-page-title-main">Carbon tetrachloride</span> Carbon compound

Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a non-flammable, dense, colourless liquid with a "sweet" chloroform-like odour that can be detected at low levels. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, an anthelmintic and a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal.

Chloromethane, also called methyl chloride, Refrigerant-40, R-40 or HCC 40, is an organic compound with the chemical formula CH3Cl. One of the haloalkanes, it is a colorless, sweet-smelling, flammable gas. Methyl chloride is a crucial reagent in industrial chemistry, although it is rarely present in consumer products, and was formerly utilized as a refrigerant. Most chloromethane is biogenic.

<span class="mw-page-title-main">Refrigerant</span> Substance in a refrigeration cycle

A refrigerant is a working fluid used in cooling, heating or reverse cooling and heating of air conditioning systems and heat pumps where they undergo a repeated phase transition from a liquid to a gas and back again. Refrigerants are heavily regulated because of their toxicity and flammability and the contribution of CFC and HCFC refrigerants to ozone depletion and that of HFC refrigerants to climate change.

<span class="mw-page-title-main">Halomethane</span> Halogen compounds derived from methane

Halomethane compounds are derivatives of methane with one or more of the hydrogen atoms replaced with halogen atoms. Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably as refrigerants, solvents, propellants, and fumigants. Many, including the chlorofluorocarbons, have attracted wide attention because they become active when exposed to ultraviolet light found at high altitudes and destroy the Earth's protective ozone layer.

<span class="mw-page-title-main">Methyl formate</span> Chemical compound

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.

Dichlorodifluoromethane (R-12) is a colorless gas popularly known by the genericized brand name Freon. It is a chlorofluorocarbon halomethane (CFC) used as a refrigerant and aerosol spray propellant. In compliance with the Montreal Protocol, its manufacture was banned in developed countries in 1996, and in developing countries in 2010 out of concerns about its damaging effect on the ozone layer. Its only allowed usage is as a fire retardant in submarines and aircraft. It is soluble in many organic solvents. R-12 cylinders are colored white.

1,1,1,2-Tetrafluoroethane (also known as norflurane (INN), R-134a, Klea 134a, Freon 134a, Forane 134a, Genetron 134a, Green Gas, Florasol 134a, Suva 134a, HFA-134a, or HFC-134a) is a hydrofluorocarbon (HFC) and haloalkane refrigerant with thermodynamic properties similar to R-12 (dichlorodifluoromethane) but with insignificant ozone depletion potential and a lower 100-year global warming potential (1,430, compared to R-12's GWP of 10,900). It has the formula CF3CH2F and a boiling point of −26.3 °C (−15.34 °F) at atmospheric pressure. R-134a cylinders are colored light blue. A phaseout and transition to HFO-1234yf and other refrigerants, with GWPs similar to CO2, began in 2012 within the automotive market.

<span class="mw-page-title-main">Chlorodifluoromethane</span> Chemical propellant and refrigerant

Chlorodifluoromethane or difluoromonochloromethane is a hydrochlorofluorocarbon (HCFC). This colorless gas is better known as HCFC-22, or R-22, or CHClF
2. It was commonly used as a propellant and refrigerant. These applications were phased out under the Montreal Protocol in developed countries in 2020 due to the compound's ozone depletion potential (ODP) and high global warming potential (GWP), and in developing countries this process will be completed by 2030. R-22 is a versatile intermediate in industrial organofluorine chemistry, e.g. as a precursor to tetrafluoroethylene.

<span class="mw-page-title-main">Nitrogen trifluoride</span> Chemical compound

Nitrogen trifluoride is the inorganic compound with the formula. It is a colorless, non-flammable, toxic gas with a slightly musty odor. In contrast with ammonia, it is nonbasic. It finds increasing use within the manufacturing of flat-panel displays, photovoltaics, LEDs and other microelectronics. NF
3 is a greenhouse gas, with a global warming potential (GWP) 17,200 times greater than that of CO
2 when compared over a 100-year period.

1,2-Dichlorotetrafluoroethane, or R-114, also known as cryofluorane (INN), is a chlorofluorocarbon (CFC) with the molecular formula ClF2CCF2Cl. Its primary use has been as a refrigerant. It is a non-flammable gas with a sweetish, chloroform-like odor with the critical point occurring at 145.6 °C and 3.26 MPa. When pressurized or cooled, it is a colorless liquid. It is listed on the Intergovernmental Panel on Climate Change's list of ozone depleting chemicals, and is classified as a Montreal Protocol Class I, group 1 ozone depleting substance.

Chlorotrifluoromethane, R-13, CFC-13, or Freon 13, is a non-flammable, non-corrosive, nontoxic chlorofluorocarbon (CFC) and also a mixed halomethane. It is a man-made substance used primarily as a refrigerant. When released into the environment, CFC-13 has a high ozone depletion potential, and long atmospheric lifetime. Only a few other greenhouse gases surpass CFC-13 in global warming potential (GWP). The IPCC AR5 reported that CFC-13's atmospheric lifetime was 640 years.

<span class="mw-page-title-main">Dichlorofluoromethane</span> Chemical compound

Dichlorofluoromethane or Freon 21 or R 21 is a halomethane or hydrochlorofluorocarbon with the formula CHCl2F. It is a colorless and odorless gas. It is produced by fluorination of chloroform using a catalyst such as antimony trifluoride:

<span class="mw-page-title-main">Chloropentafluoroethane</span> Chemical compound

Chloropentafluoroethane is a chlorofluorocarbon (CFC) once used as a refrigerant and also known as R-115 and CFC-115. Its production and consumption has been banned since 1 January 1996 under the Montreal Protocol because of its high ozone depletion potential and very long lifetime when released into the environment. CFC-115 is also a potent greenhouse gas.

1,1,2-Trichloro-1,2,2-trifluoroethane, also called trichlorotrifluoroethane or CFC-113, is a chlorofluorocarbon. It has the formula Cl2FC−CClF2. This colorless, volatile liquid is a versatile solvent.

<span class="mw-page-title-main">1,1-Dichloro-1-fluoroethane</span> Chemical compound

1,1-Dichloro-1-fluoroethane is a haloalkane with the formula C
2H
3Cl
2F. It is one of the three isomers of dichlorofluoroethane. It belongs to the hydrochlorofluorocarbon (HCFC) family of man-made compounds that contribute significantly to both ozone depletion and global warming when released into the environment.

<span class="mw-page-title-main">1-Chloro-1,1-difluoroethane</span> Chemical compound

1-Chloro-1,1-difluoroethane (HCFC-142b) is a haloalkane with the chemical formula CH3CClF2. It belongs to the hydrochlorofluorocarbon (HCFC) family of man-made compounds that contribute significantly to both ozone depletion and global warming when released into the environment. It is primarily used as a refrigerant where it is also known as R-142b and by trade names including Freon-142b.

<span class="mw-page-title-main">Tetrachloro-1,1-difluoroethane</span> Chemical compound

Tetrachloro-1,1-difluoroethane or 1,1,1,2-tetrachloro-2,2-difluoroethane, Freon 112a, R-112a, or CFC-112a is an asymmetric chlorofluorocarbon isomer of tetrachloro-1,1-difluoroethane with formula CClF2CCl3. It contains ethane substituted by four chlorine atoms and two fluorine atoms. With a boiling point of 91.5°C it is the freon with second highest boiling point.

<span class="mw-page-title-main">1,1-Dichlorotetrafluoroethane</span> Chemical compound

1,1-Dichlorotetrafluoroethane is a chlorofluorocarbon also known as CFC-114a or R114a by American Society of Heating, Refrigerating, and Air Conditioning Engineers. It has two chlorine atoms on one carbon atom and none on the other. It is one of two isomers of dichlorotetrafluoroethane, the other being 1,2-dichlorotetrafluoroethane, also known as CFC-114.

References

  1. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0290". 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. ↑ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ↑ "Fluorotrichloromethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ↑ Siegemund, 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. 1 2 "International Treaties and Cooperation about the Protection of the Stratospheric Ozone Layer". U.S. Environmental Protection Agency. 15 July 2015. Retrieved 2021-02-14.
  7. ↑ "R-10 ,R-11 ,R-12 GASES - ملتقى التبريد والتكييف HVACafe". ملتقى التبريد والتكييف HVACafe (in Arabic). 2017-05-25. Archived from the original on 2018-05-18. Retrieved 2018-05-18.
  8. 1 2 3 Katritzky, Alan R.; Gilchrist, Thomas L.; Meth-Cohn, Otto; Rees, Charles Wayne (1995), Comprehensive Organic Functional Group Transformations, Elsevier, p. 220, ISBN   978-0-08-042704-1 – via Google Books
  9. ↑ Banks, A.A.; Emeléus, H.J.; Haszeldine, R. N.; Kerrigan, V. (December 1948). "443. The reaction of bromine trifluoride and iodine pentafluoride with carbon tetrachloride, tetrabromide, and tetraiodide and with tetraiodoethylene". Journal of the Chemical Society : 2188–2190. doi:10.1039/JR9480002188.
  10. ↑ Montzka SA, Dutton GS, Yu P, et al. (2018). "An unexpected and persistent increase in global emissions of ozone-depleting CFC-11". Nature. 557 (7705). Springer Nature: 413–417. Bibcode:2018Natur.557..413M. doi:10.1038/s41586-018-0106-2. hdl: 1983/fd5eaf00-34b1-4689-9f23-410a54182b61 . PMID   29769666. S2CID   21705434.
  11. ↑ Johnson, Scott (5 May 2018). "It seems someone is producing a banned ozone-depleting chemical again". Ars Technica. Retrieved 18 October 2018. Decline of CFC-11 has slowed in recent years, pointing to a renewed source
  12. ↑ McGrath, Matt (9 July 2018). "China 'home foam' gas key to ozone mystery". BBC News . Retrieved 9 July 2018.
  13. ↑ Chu, Jennifer (2021-02-10). "Reductions in CFC-11 emissions put ozone recovery back on track". MIT News .
  14. ↑ "Proposal for a regulation of the european parliament and the council on substances that deplete the ozone layer" (PDF). European Commission. European Commission-DG Environment. 2022-05-04. Retrieved 24 November 2022.
  15. ↑ Orr, Bryan (4 January 2021). "False Alarms: The Legacy of Phosgene Gas". HVAC School. Retrieved 9 May 2022.
  16. ↑ Lin, Henry W.; Abad, Gonzalo Gonzalez; Loeb, Abraham (2014-08-12). "Detecting industrial pollution in the atmospheres of earth-like exoplanets". The Astrophysical Journal. 792 (1): L7. arXiv: 1406.3025 . doi:10.1088/2041-8205/792/1/L7. ISSN   2041-8213.
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