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Dichlorodifluoromethane

From Wikipedia, the free encyclopedia
Dichlorodifluoromethane
Names
Preferred IUPAC name
Dichlorodi(fluoro)methane
Other names
  • Dichlorodifluoromethane
  • Carbon dichloride difluoride
  • Dichloro-difluoro-methane
  • Difluorodichloromethane
  • Freon 12
  • R-12
  • CFC-12
  • P-12
  • Propellant 12
  • Halon 122
  • Arcton 6
  • Arcton 12
  • E940
  • Fluorocarbon 12
  • Genetron 12
  • Refrigerant 12
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard100.000.813Edit this at Wikidata
EC Number
  • 200-893-9
E numberE940(glazing agents, ...)
KEGG
RTECS number
  • PA8200000
UNII
UN number1028
  • InChI=1S/CCl2F2/c2-1(3,4)5 checkY
    Key: PXBRQCKWGAHEHS-UHFFFAOYSA-N checkY
  • InChI=1/CCl2F2/c2-1(3,4)5
    Key: PXBRQCKWGAHEHS-UHFFFAOYAX
  • ClC(Cl)(F)F
Properties
CCl2F2
Molar mass120.91 g·mol−1
AppearanceColorless gas
Odorether-like at very high concentrations
Density1.486 g/cm3 (−29.8 °C (−21.6 °F))
Melting point−157.7 °C (−251.9 °F; 115.5 K)
Boiling point−29.8 °C (−21.6 °F; 243.3 K)
0.286 g/L at 20 °C (68 °F)
Solubility in alcohol, ether, benzene, acetic acidSoluble
logP2.16
Vapor pressure568 kPa (20 °C (68 °F))
0.0025 mol kg−1 bar−1
−52.2·10−6 cm3/mol
Thermal conductivity0.0097 W/(m·K) (300 K)[1]
Structure
Tetrahedral
0.51D[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H336,H420
P261,P271,P304+P340,P319,P403+P233,P405,P410+P403,P501,P502
NFPA 704 (fire diamond)
Flash pointNon-flammable[3]
Lethal dose or concentration (LD, LC):
760,000 ppm (mouse, 30 min)
800,000 ppm (rabbit, 30 min)
800,000 ppm (guinea pig, 30 min)
600,000 ppm (rat, 2h)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 1000 ppm (4950 mg/m3)[3]
REL (Recommended)
TWA 1000 ppm (4950 mg/m3)[3]
IDLH (Immediate danger)
15000 ppm[3]
Supplementary data page
Dichlorodifluoromethane (data page)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Dichlorodifluoromethane (R-12) is a colorless gas popularly known by thegenericized brand nameFreon (asFreon-12). It is achlorofluorocarbonhalomethane (CFC) used as arefrigerant andaerosol spray propellant. In compliance with theMontreal Protocol, its manufacture was banned in developed countries (non-article 5 countries) in 1996, and in developing countries (Article 5 countries) in 2010 out of concerns about its damaging effect on theozone layer.[5] Its only allowed usage is as afire retardant in submarines and aircraft. It issoluble in manyorganicsolvents. R-12 cylinders are colored white.

Preparation

[edit]

It can be prepared by reactingcarbon tetrachloride withhydrogen fluoride in the presence of acatalytic amount ofantimony pentachloride:

CCl4 + 2HF → CCl2F2 + 2HCl

This reaction can also producetrichlorofluoromethane (CCl3F),chlorotrifluoromethane (CClF3) andtetrafluoromethane (CF4).[6]

History

[edit]

Charles F. Kettering, vice president of General Motors Research Corporation, was seeking a refrigerant replacement that would be colorless, odorless, tasteless, nontoxic, and nonflammable. He assembled a team that includedThomas Midgley Jr.,Albert Leon Henne, and Robert McNary. From 1930 to 1935, they developed dichlorodifluoromethane (CCl2F2 or R12),trichlorofluoromethane (CCl3F or R11),chlorodifluoromethane (CHClF2 or R22),trichlorotrifluoroethane (CCl2FCClF2 or R113), anddichlorotetrafluoroethane (CClF2CClF2 or R114), throughKinetic Chemicals which was a joint venture betweenDuPont andGeneral Motors.[7]

Use as an aerosol

[edit]

The use of chlorofluorocarbons as aerosols in medicine, such asUSP-approvedsalbutamol, has been phased out by theU.S. Food and Drug Administration. A different propellant known ashydrofluoroalkane, or HFA, which was not known to harm the environment, was chosen to replace it.[8] That being said it still listed on the FDA's approved food additive list.

CAS Reg. No. (or other ID)*:75-71-8

Environmental Effects

[edit]

R-12 has the highest ozone depletion potential among chlorocarbons due to the presence of 2 chlorine atoms in the molecule.R-12 also has intense global warming potential (GWP) with the 20yr, 100yr and 500yr GWP being 11400, 11200 and 5100 times greater thanCO2.[9]

Retrofitting

[edit]

R-12 was used in most refrigeration and vehicle air conditioning applications prior to 1994 before being replaced by1,1,1,2-tetrafluoroethane (R-134a), which has an insignificantozone depletion potential. Automobile manufacturers began phasing in R-134a around 1993[citation needed]. When older units leak or require repair involving removal of the refrigerant,retrofitment to a refrigerant other than R-12 (most commonly R-134a) is required in some jurisdictions. The United States does not require such conversion. Retrofitment requires a system flush and a new filter/dryer or accumulator, and may also involve the installation of new seals and/or hoses made of materials compatible with the refrigerant being installed. Mineral oil used with R-12 is not compatible with R-134a. Some oils designed for conversion to R-134a are advertised as compatible with residual R-12 mineral oil. Illegal replacements for R-12 include highly flammable hydrocarbon blends such asHC-12a, the flammability of which has caused injuries and deaths.[10][11]

Dangers

[edit]

Aside from its environmental impacts, R12, like most chlorofluoroalkanes, formsphosgene gas when exposed to a naked flame.[12]

Properties

[edit]

Table of thermal and physical properties of saturated liquid refrigerant 12:[13][14]

Temperature (°C)Density (kg/m3)Specific heat (kJ/kg K)Kinematic viscosity (m2/s)Conductivity (W/m K)Thermal diffusivity (m2/s)Prandtl NumberBulk modulus (K−1)
−501546.750.8753.10×10−70.0675.01×10−16.22.63×10−3
−401518.710.88472.79×10−70.0695.14×10−15.4
−301489.560.89562.53×10−70.0695.26×10−14.8
−201460.570.90732.35×10−70.0715.39×10−14.4
−101429.490.92032.21×10−70.0735.50×10−14
01397.450.93452.14×10−70.0735.57×10−13.8
101364.30.94962.03×10−70.0735.60×10−13.6
201330.180.96591.98×10−70.0735.60×10−13.5
301295.10.98351.94×10−70.0715.60×10−13.5
401257.131.00191.91×10−70.0695.55×10−13.5
501215.961.02161.90×10−70.0675.45×10−13.5

Gallery

[edit]
  • CFC-12 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 in parts-per-trillion.
    CFC-12 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.
  • Hemispheric and global mean CFC-12 concentrations (NOAA/ESRL)
    Hemispheric and global mean CFC-12 concentrations (NOAA/ESRL)
  • Time-series of atmospheric concentrations of CFC-12 (Walker et al., 2000)
    Time-series of atmospheric concentrations of CFC-12 (Walkeret al., 2000)
  • 1990s sea surface CFC-12 concentration
    1990s sea surface CFC-12 concentration
  • 1990s CFC-12 oceanic vertical inventory
    1990s CFC-12 oceanic vertical inventory
  • CFC-12, CFC-11, H-1211 and SF6 vertical profiles
    CFC-12, CFC-11, H-1211 and SF6 vertical profiles

References

[edit]
  1. ^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.
  2. ^Khristenko, Sergei V.; Maslov, Alexander I. and Viatcheslav P. Shevelko;Molecules and Their Spectroscopic Properties, p. 74ISBN 3642719481.
  3. ^abcdNIOSH Pocket Guide to Chemical Hazards."#0192".National Institute for Occupational Safety and Health (NIOSH).
  4. ^"Dichlorodifluoromethane".Immediately Dangerous to Life or Health Concentrations (IDLH).National Institute for Occupational Safety and Health (NIOSH).
  5. ^"1:Update on Ozone-Depleting Substances (ODSs) and Other Gases of Interest to the Montreal Protocol".Scientific assessment of ozone depletion: 2018(PDF) (Global Ozone Research and Monitoring Project–Report No. 58 ed.). Geneva, Switzerland: World Meteorological Organization. 2018. p. 1.10.ISBN 978-1-7329317-1-8. Retrieved22 November 2020.
  6. ^Greenwood, Norman N.; Earnshaw, Alan (1997).Chemistry of the Elements (2nd ed.).Butterworth-Heinemann. p. 304.ISBN 978-0-08-037941-8.
  7. ^Plunkett, Roy J. (1986).High Performance Polymers: Their Origin and Development. Elsevier Science Publishing Co., Inc. pp. 261–262.ISBN 978-94-011-7073-4.
  8. ^"Asthma inhaler replacements coming to Pa. - Pittsburgh Tribune-Review". 16 February 2007. Archived fromthe original on 16 February 2007. Retrieved26 April 2022.
  9. ^"IPCC Sixth Assessment Report - The Physical Science Basis - Chapter 7 Supplementary Material Table 7"(PDF). Archived fromthe original(PDF) on 30 June 2024. Retrieved1 November 2024.
  10. ^"Se cumplen 13 años de la Tragedia de la Cresta".Ensegundos.com.pa. 23 October 2019.
  11. ^"Victims of the La Cresta tragedy were remembered".M.metrolibra.com. Retrieved26 April 2022.
  12. ^"False Alarms: The Legacy of Phosgene Gas".HVAC School. 4 January 2021. Retrieved9 May 2022.
  13. ^Holman, Jack P. (2002).Heat Transfer (9th ed.). New York, NY: McGraw-Hill Companies, Inc. pp. 600–606.ISBN 9780072406559.
  14. ^Incropera 1 Dewitt 2 Bergman 3 Lavigne 4, Frank P. 1 David P. 2 Theodore L. 3 Adrienne S. 4 (2007).Fundamentals of Heat and Mass Transfer (6th ed.). Hoboken, NJ: John Wiley and Sons, Inc. pp. 941–950.ISBN 9780471457282.{{cite book}}: CS1 maint: numeric names: authors list (link)

External links

[edit]


Salts and covalent derivatives of thefluoride ion
HF?HeF2
LiFBeF2BF
BF3
B2F4
+BO3
CF4
CxFy
+CO3
NF3
FN3
N2F2
NF
N2F4
NF2
?NF5
+N
+NO3
OF2
O2F2
OF
O3F2
O4F2
?OF4
F2Ne
NaFMgF2AlF
AlF3
SiF4P2F4
PF3
PF5
+PO4
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
?RnF
4

?RnF
6
FrFRaF2 LrF3RfDbSgBhHsMtDsRgCnNhFlMcLvTsOg
LaF3CeF3
CeF4
PrF3
PrF4
NdF2
NdF3
NdF4
PmF3SmF
SmF2
SmF3
EuF2
EuF3
GdF3TbF3
TbF4
DyF2
DyF3
DyF4
HoF3ErF3TmF2
TmF3
YbF2
YbF3
AcF3ThF3
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
FmMdNo
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
Unsubstituted
Monosubstituted
Disubstituted
Trisubstituted
Tetrasubstituted
*Chiral compound.
Authority control databases: NationalEdit this at Wikidata
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