Trifluoroiodomethane

Last updated
Trifluoroiodomethane
Trifluoroiodomethane.png
Trifluoroiodomethane-3D-vdW.png
Names
Preferred IUPAC name
Trifluoro(iodo)methane
Other names
Trifluoroiodomethane
Iodotrifluoromethane
Monoiodotrifluoromethane
Trifluoromethyl iodide
Perfluoromethyl iodide
Freon 13T1
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.286 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-014-5
PubChem CID
RTECS number
  • PB6975000
UNII
  • InChI=1S/CF3I/c2-1(3,4)5 Yes check.svgY
    Key: VPAYJEUHKVESSD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CF3I/c2-1(3,4)5
  • FC(F)(F)I
Properties
CF3I
Molar mass 195.91 g/mol
AppearanceColorless odorless gas
Density 2.5485 g/cm3 at -78.5 °C
2.3608 g/cm3 at -32.5 °C
Melting point −110 °C (−166 °F; 163 K)
Boiling point −22.5 °C (−8.5 °F; 250.7 K)
Slightly
Vapor pressure 541 kPa
Hazards
GHS labelling:
GHS-pictogram-silhouette.svg
Warning
H341
P201, P202, P281, P308+P313, P405, P501
Supplementary data page
Trifluoroiodomethane (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 ?)

Trifluoroiodomethane, also referred to as trifluoromethyl iodide is a halomethane with the formula CF3I. It is an experimental alternative to Halon 1301 (CBrF3) in unoccupied areas. [1] It would be used as a gaseous fire suppression flooding agent for in-flight aircraft and electronic equipment fires.

Contents

Chemistry

It is used in the rhodium-catalyzed α-trifluoromethylation of α,β-unsaturated ketones. [2]

It can be used as a new generation fire extinguishing agent to replace Halon in fire protection systems. [3] The mechanism of extinguishing fires for CF3I is active and primarily based on interruption of the chain reaction in the combustion area of the flame by so-called "negative" catalytic action. [4] It is also used as an eco-friendly insulation gas to replace SF6 in electrical power industry. [5]

In the presence of sunlight or at temperatures above 100 °C it can react with water, forming hazardous by-products such as hydrogen fluoride (HF), hydrogen iodide (HI) and carbonyl fluoride (COF2).[ citation needed ]

Environmental effects

Trifluoroiodomethane contains carbon, fluorine, and iodine atoms. Although iodine is several hundred times more efficient at destroying stratospheric ozone than chlorine, experiments have shown that because the weak C-I bond breaks easily under the influence of water (owing to the electron-attracting fluorine atoms), trifluoroiodomethane has an ozone depleting potential less than one-thousandth that of Halon 1301 (0.008-0.01). Its atmospheric lifetime, at less than 1 month, is less than 1 percent that of Halon 1301, and less even than hydrogen chloride formed from volcanoes.

There is, however, still the problem of the C-F bonds absorbing in the atmospheric window. [6] However, the IPCC has calculated the 100-year global warming potential of trifluoroiodomethane to be 0.4 (i.e., 40% of that of CO2). [7]

Related Research Articles

<span class="mw-page-title-main">Bromine</span> Chemical element, symbol Br and atomic number 35

Bromine is a chemical element; it has symbol Br and atomic number 35. It is a volatile red-brown liquid at room temperature that evaporates readily to form a similarly coloured vapour. Its properties are intermediate between those of chlorine and iodine. Isolated independently by two chemists, Carl Jacob Löwig and Antoine Jérôme Balard, its name was derived from the Ancient Greek βρῶμος (bromos) meaning "stench", referring to its sharp and pungent smell.

<span class="mw-page-title-main">Halogen</span> Group of chemical elements

The halogens are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group 17.

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

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">Fluorocarbon</span> Class of chemical compounds

Fluorocarbons are chemical compounds with carbon-fluorine bonds. Compounds that contain many C-F bonds often have distinctive properties, e.g., enhanced stability, volatility, and hydrophobicity. Several fluorocarbons and their derivatives are commercial polymers, refrigerants, drugs, and anesthetics.

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

Bromochlorodifluoromethane (BCF), also referred to by the code numbers Halon 1211 and Freon 12B1, is a haloalkane with the chemical formula CF2ClBr. It is used for fire suppression, especially for expensive equipment or items that could be damaged by the residue from other types of extinguishers. It is stored as a liquid under pressure and vaporizes when discharged to suppress fires. The use of halons, including Halon 1211, has decreased over time due to their adverse impact on the ozone layer. Alternatives have been developed to mitigate environmental concerns while still providing effective fire suppression capabilities.

Bromotrifluoromethane, commonly known as 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.

<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.

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. CFC-11 is a Class 1 ozone-depleting substance which damages Earth's protective stratospheric ozone layer.

Dioxygen difluoride is a compound of fluorine and oxygen with the molecular formula O2F2. It can exist as an orange-colored solid which melts into a red liquid at −163 °C (110 K). It is an extremely strong oxidant and decomposes into oxygen and fluorine even at −160 °C (113 K) at a rate of 4% per dayits lifetime at room temperature is thus extremely short. Dioxygen difluoride reacts vigorously with nearly every chemical it encounters (including ordinary ice) leading to its onomatopoeic nickname FOOF (a play on its chemical structure and its explosive tendencies).

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 with C3v symmetry. Fluoroform is used in diverse applications in organic synthesis. It is not an ozone depleter but is a greenhouse gas.

<span class="mw-page-title-main">1,1,1,2,3,3,3-Heptafluoropropane</span> Chemical compound

1,1,1,2,3,3,3-Heptafluoropropane, also called heptafluoropropane, HFC-227ea, HFC-227 or FM-200, as well as apaflurane (INN), is a colourless, odourless gaseous halocarbon commonly used as a gaseous fire suppression agent.

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.

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

Dibromodifluoromethane is a mixed halomethane. It is a colorless non-flammable liquid. Along with Halons 1211, 2402, and 1301, it is one of the most effective fire extinguishers, however, it is also very toxic. It is a class I ozone depleting substance (ODS).

<span class="mw-page-title-main">Fire extinguisher</span> Active fire protection device

A fire extinguisher is a handheld active fire protection device usually filled with a dry or wet chemical used to extinguish or control small fires, often in emergencies. It is not intended for use on an out-of-control fire, such as one which has reached the ceiling, endangers the user, or otherwise requires the equipment, personnel, resources or expertise of a fire brigade. Typically, a fire extinguisher consists of a hand-held cylindrical pressure vessel containing an agent that can be discharged to extinguish a fire. Fire extinguishers manufactured with non-cylindrical pressure vessels also exist but are less common.

<span class="mw-page-title-main">Automatic fire suppression</span> Automatic Emergency Systems

Automatic fire suppression systems control and extinguish fires without human intervention. Examples of automatic systems include fire sprinkler system, gaseous fire suppression, and condensed aerosol fire suppression. When fires are extinguished in the early stages loss of life is minimal since 93% of all fire-related deaths occur once the fire has progressed beyond the early stages.

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

Perfluorobutane (PFB) is an inert, high-density colorless gas. It is a simple fluorocarbon with a n-butane skeleton and all the hydrogen atoms replaced with fluorine atoms.

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

Pentafluoroethane is a fluorocarbon with the formula CF3CHF2. Pentafluoroethane is currently used as a refrigerant (known as R-125) and also used as a fire suppression agent in fire suppression systems.

<span class="mw-page-title-main">Condensed aerosol fire suppression</span> Particle-based form of fire extinction

Condensed aerosol fire suppression is a particle-based method of fire extinction. It is similar to but not identical to dry chemical fire extinction methods, using an innovative pyrogenic, condensed aerosol fire suppressant. It is a highly effective fire suppression method for class A, B, C, E and F. Some aerosol-generating compounds produce a corrosive by-product that may damage electronic equipment, although later generations lower the effect.

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

Thiophosphoryl fluoride is an inorganic molecular gas with formula PSF3 containing phosphorus, sulfur and fluorine. It spontaneously ignites in air and burns with a cool flame. The discoverers were able to have flames around their hands without discomfort, and called it "probably one of the coldest flames known". The gas was discovered in 1888.

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.

References

  1. Vitali, Juan. "Halon Substitute Protects Aircrews and the Ozone Layer". www.afrlhorizons.com. Archived from the original on 11 July 2007. Retrieved 2017-09-06.
  2. "Trifluoroiodomethane 171441". Sigma-Aldrich. Retrieved 2017-09-06.
  3. "Fire extinguishing agents trifluoroiodomethane/CF3I". beijingyuji. Retrieved 2018-09-20.[ unreliable source? ]
  4. "CFI rim seal fire protection for floating roof tanks" (PDF). 2018-09-20.
  5. Katagiri, H.; Kasuya, H.; Mizoguchi, H.; Yanabu, S. (October 2008). "Investigation of the Performance of CF3I Gas as a Possible Substitute for SF6". IEEE Transactions on Dielectrics and Electrical Insulation . 15 (5): 1424–1429. doi:10.1109/TDEI.2008.4656252. S2CID   21905295.
  6. Shimanouchi, T. (July 1977). "Tables of molecular vibrational frequencies. Consolidated volume II". Journal of Physical and Chemical Reference Data. 6 (3): 993–1102. Bibcode:1977JPCRD...6..993S. doi:10.1063/1.555560.
  7. Ramfjord, Birgit (2012-03-05). "Listing of GWP Values as per Report IPCC WG1 AR4" (PDF). Swedish Defence Materiel Administration. Archived from the original (PDF) on 13 March 2016. Retrieved 7 September 2017.

Further reading