Fluoroform

Fluoroform
Names
IUPAC name
Trifluoromethane
Other names
Fluoroform, carbon trifluoride,[citation needed] methyl trifluoride, Fluoryl, Freon 23, Arcton 1
Identifiers
3D model (JSmol)
Abbreviations HFC 23, R-23, FE-13, UN 1984
ChEBI
ChemSpider
ECHA InfoCard 100.000.794 Edit this at Wikidata
EC Number
  • 200-872-4
RTECS number
  • PB6900000
UNII
  • InChI=1S/CHF3/c2-1(3)4/h1H checkY
    Key: XPDWGBQVDMORPB-UHFFFAOYSA-N checkY
  • InChI=1/CHF3/c2-1(3)4/h1H
    Key: XPDWGBQVDMORPB-UHFFFAOYAM
  • FC(F)F
Properties
CHF3
Molar mass 70.014 g·mol−1
Appearance Colorless gas
Density 2.946 kg/m3 (gas, 1 bar, 15 °C)
Melting point −155.2 °C (−247.4 °F; 118.0 K)
Boiling point −82.1 °C (−115.8 °F; 191.1 K)
1 g/l
Solubility in organic solvents Soluble
Vapor pressure 4.38 MPa at 20 °C
0.013 mol·kg−1·bar−1
Acidity (pKa) 25–28
Structure
Tetrahedral
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Nervous system depression
GHS labelling:
GHS04: Compressed Gas
Warning
H280
P403
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Flash point Non-flammable
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Fluoroform, or trifluoromethane, is the chemical compound with the formula CHF3. It is a hydrofluorocarbon as well as being apart of the haloforms, a class of compounds with the formula CHX3 (X = halogen) with C3v symmetry. Fluoroform is used in diverse applications in organic synthesis. It is not an ozone depleter but is a greenhouse gas.

Synthesis

About 20 million kg per year are produced industrially as both a by-product of and precursor to the manufacture of Teflon. It is produced by reaction of chloroform with HF:

CHCl3 + 3 HF → CHF3 + 3 HCl

It is also generated biologically in small amounts apparently by decarboxylation of trifluoroacetic acid.

Historical

Fluoroform was first obtained by Maurice Meslans in the violent reaction of iodoform with dry silver fluoride in 1894. The reaction was improved by Otto Ruff by substitution of silver fluoride by a mixture of mercury fluoride and calcium fluoride. The exchange reaction works with iodoform and bromoform, and the exchange of the first two halogen atoms by fluorine is vigorous. By changing to a two step process, first forming a bromodifluoromethane in the reaction of antimony trifluoride with bromoform and finishing the reaction with mercury fluoride the first efficient synthesis method was found by Henne.

Industrial applications

CHF3 is used in the semiconductor industry in plasma etching of silicon oxide and silicon nitride. Known as R-23 or HFC-23, it was also a useful refrigerant, sometimes as a replacement for chlorotrifluoromethane (CFC-13) and is a byproduct of its manufacture.

When used as a fire suppressant, the fluoroform carries the DuPont trade name, FE-13. CHF3 is recommended for this application because of its low toxicity, its low reactivity, and its high density. HFC-23 has been used in the past as a replacement for Halon 1301(CFC-13B1) in fire suppression systems as a total flooding gaseous fire suppression agent.

Organic chemistry

Fluoroform is weakly acidic with a pKa = 25–28 and quite inert. Attempted deprotonation results in defluorination to generate F and difluorocarbene (CF2). Some organocopper and organocadmium compounds have been developed as trifluoromethylation reagents.

Fluoroform is a precursor of the Ruppert-Prakash reagent CF3Si(CH3)3, which is a source of the nucleophilic CF3 anion.

Greenhouse gas

HFC-23 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.
Atmospheric concentration of HFC-23 vs. similar man-made gases (right graph), log scale.

CHF3 is a potent greenhouse gas. A ton of HFC-23 in the atmosphere has the same effect as 11,700 tons of carbon dioxide. This equivalency, also called a 100-yr global warming potential, is slightly larger at 14,800 for HFC-23. The atmospheric lifetime is 270 years.

HFC-23 was the most abundant HFC in the global atmosphere until around 2001, when the global mean concentration of HFC-134a (1,1,1,2-tetrafluoroethane), the chemical now used extensively in automobile air conditioners, surpassed those of HFC-23. Global emissions of HFC-23 have in the past been dominated by the inadvertent production and release during the manufacture of the refrigerant HCFC-22 (chlorodifluoromethane).

Substantial decreases in HFC-23 emissions by developed countries were reported from the 1990s to the 2000s: from 6-8 Gg/yr in the 1990s to 2.8 Gg/yr in 2007.

The UNFCCC Clean Development Mechanism provided funding and facilitated the destruction of HFC-23.

Developing countries have become the largest producers of HCFC-23 in recent years according to data compiled by the Ozone Secretariat of the World Meteorological Organization. Emissions of all HFCs are included in the UNFCCCs Kyoto Protocol. To mitigate its impact, CHF3 can be destroyed with electric plasma arc technologies or by high temperature incineration.

Additional physical properties

Property Value
Density (ρ) at -100 °C (liquid) 1.52 g/cm3
Density (ρ) at -82.1 °C (liquid) 1.431 g/cm3
Density (ρ) at -82.1 °C (gas) 4.57 kg/m3
Density (ρ) at 0 °C (gas) 2.86 kg/m3
Density (ρ) at 15 °C (gas) 2.99 kg/m3
Dipole moment 1.649 D
Critical pressure (pc) 4.816 MPa (48.16 bar)
Critical temperature (Tc) 25.7 °C (299 K)
Critical densityc) 7.52 mol/l
Compressibility factor (Z) 0.9913
Acentric factor (ω) 0.26414
Viscosity (η) at 25 °C 14.4 μPa.s (0.0144 cP)
Molar specific heat at constant volume (CV) 51.577 J.mol−1.K−1
Latent heat of vaporization (lb) 257.91 kJ.kg−1

This page was last updated at 2024-04-17 12:54 UTC. Update now. View original page.

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