Names | |||
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IUPAC name Trifluoromethane | |||
Other names | |||
Identifiers | |||
3D model (JSmol) | |||
Abbreviations | HFC 23, R-23, FE-13, UN 1984 | ||
ChEBI | |||
ChemSpider | |||
ECHA InfoCard | 100.000.794 | ||
EC Number |
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PubChem CID | |||
RTECS number |
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UNII | |||
CompTox Dashboard (EPA) | |||
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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 | ||
Henry's law constant (kH) | 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: [1] | |||
Warning | |||
H280 | |||
P403 | |||
NFPA 704 (fire diamond) | |||
Flash point | Non-flammable | ||
Related compounds | |||
Related compounds |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Fluoroform, or trifluoromethane, is the chemical compound with the formula CHF3. It is a hydrofluorocarbon as well as being a part 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. [2]
About 20 million kg per year are produced industrially as both a by-product of and precursor to the manufacture of Teflon. [2] It is produced by reaction of chloroform with HF: [3]
It is also generated biologically in small amounts apparently by decarboxylation of trifluoroacetic acid. [4]
Fluoroform was first obtained by Maurice Meslans in the violent reaction of iodoform with dry silver fluoride in 1894. [5] The reaction was improved by Otto Ruff by substitution of silver fluoride by a mixture of mercury fluoride and calcium fluoride. [6] 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. [6]
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.
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. [7]
Fluoroform is a precursor of the Ruppert-Prakash reagent CF3Si(CH3)3, which is a source of the nucleophilic CF−3 anion. [8] [9]
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. [10] The atmospheric lifetime is 270 years. [10]
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. [11]
However, research in 2024 strongly indicates that the HFC-23 emission decrease is much less than has been reported and does not meet the internationaly agreed Kigali Amendment of 2020. [12] [13]
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. [14] [15] [16] 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. [17]
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 density (ρc) | 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 |
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.
The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.
Bromotrifluoromethane, commonly referred to by the code numbers Halon 1301, R13B1, Halon 13B1 or BTM, is an organic halide with the chemical formula CBrF3. It is used for gaseous fire suppression as a far less toxic alternative to bromochloromethane.
Iodoform is the organoiodine compound with the chemical formula CHI3. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.
In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens. Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride.
Hydrofluorocarbons (HFCs) are synthetic organic compounds that contain fluorine and hydrogen atoms, and are the most common type of organofluorine compounds. Most are gases at room temperature and pressure. They are frequently used in air conditioning and as refrigerants; R-134a (1,1,1,2-tetrafluoroethane) is one of the most commonly used HFC refrigerants. In order to aid the recovery of the stratospheric ozone layer, HFCs were adopted to replace the more potent chlorofluorocarbons (CFCs), which were phased out from use by the Montreal Protocol, and hydrochlorofluorocarbons (HCFCs) which are presently being phased out. HFCs replaced older chlorofluorocarbons such as R-12 and hydrochlorofluorocarbons such as R-21. HFCs are also used in insulating foams, aerosol propellants, as solvents and for fire protection.
Fluoromethane, also known as methyl fluoride, Freon 41, Halocarbon-41 and HFC-41, is a non-toxic, liquefiable, and flammable gas at standard temperature and pressure. It is made of carbon, hydrogen, and fluorine. The name stems from the fact that it is methane (CH4) with a fluorine atom substituted for one of the hydrogen atoms. It is used in semiconductor manufacturing processes as an etching gas in plasma etch reactors.
Bromoform is an organic compound with the chemical formula CHBr3. It is a colorless liquid at room temperature, with a high refractive index and a very high density. Its sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. It is a brominated organic solvent. Currently its main use is as a laboratory reagent. It is very slightly soluble in water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.
In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane are replaced by halogen atoms. Trihalomethanes with all the same halogen atoms are called haloforms. Many trihalomethanes find uses in industry as solvents or refrigerants. Some THMs are also environmental pollutants, and a few are considered carcinogenic.
The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation.
Tetrafluoromethane, also known as carbon tetrafluoride or R-14, is the simplest perfluorocarbon (CF4). As its IUPAC name indicates, tetrafluoromethane is the perfluorinated counterpart to the hydrocarbon methane. It can also be classified as a haloalkane or halomethane. Tetrafluoromethane is a useful refrigerant but also a potent greenhouse gas. It has a very high bond strength due to the nature of the carbon–fluorine bond.
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.
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.
Organofluorine chemistry describes the chemistry of organofluorine compounds, organic compounds that contain a carbon–fluorine bond. Organofluorine compounds find diverse applications ranging from oil and water repellents to pharmaceuticals, refrigerants, and reagents in catalysis. In addition to these applications, some organofluorine compounds are pollutants because of their contributions to ozone depletion, global warming, bioaccumulation, and toxicity. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.
Fluorine is a chemical element; it has symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as pale yellow diatomic gas. Fluorine is extremely reactive as it reacts with all other elements except for the light inert gases. It is highly toxic.
In chemistry, the haloform reaction is a chemical reaction in which a haloform is produced by the exhaustive halogenation of an acetyl group, in the presence of a base. The reaction can be used to transform acetyl groups into carboxyl groups or to produce chloroform, bromoform, or iodoform. Note that fluoroform can't be prepared in this way.
Hydrofluoroolefins (HFOs) are unsaturated organic compounds composed of hydrogen, fluorine and carbon. These organofluorine compounds are of interest as refrigerants. Unlike traditional hydrofluorocarbons (HFCs) and chlorofluorocarbons (CFCs), which are saturated, HFOs are olefins, otherwise known as alkenes.
Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib, and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.
Alan K. Brisdon is a British chemist and a Senior Lecturer in the Department of Chemistry at The University of Manchester. His research in general is based on fluorine chemistry, including on HCFCs, fluorine-containing organometallic systems, fluorophosphines and fluorine-containing materials, such as ionic liquids and fluorographenes.