Perfluorotributylamine

Source: Wikipedia, the free encyclopedia.
Perfluorotributylamine
Names
Preferred IUPAC name
1,1,2,2,3,3,4,4,4-Nonafluoro-N,N-bis(nonafluorobutyl)butan-1-amine
Other names
Fluorinert
Identifiers
3D model (
JSmol
)
Abbreviations PFTBA
ChEBI
ChemSpider
ECHA InfoCard
 100.005.659 Edit this at Wikidata
UNII
  • InChI=1S/C12F27N/c13-1(14,7(25,26)27)4(19,20)10(34,35)40(11(36,37)5(21,22)2(15,16)8(28,29)30)12(38,39)6(23,24)3(17,18)9(31,32)33
    Key: RVZRBWKZFJCCIB-UHFFFAOYSA-N
  • InChI=1/C12F27N/c13-1(14,7(25,26)27)4(19,20)10(34,35)40(11(36,37)5(21,22)2(15,16)8(28,29)30)12(38,39)6(23,24)3(17,18)9(31,32)33
    Key: RVZRBWKZFJCCIB-UHFFFAOYAW
  • C(C(C(F)(F)F)(F)F)(C(N(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F
Properties
N(CF2CF2CF2CF3)3
Molar mass 671.096 g·mol−1
Appearance colorless liquid
Density 1.884 g/mL
Melting point −50 °C (−58 °F; 223 K)
Boiling point 178 °C (352 °F; 451 K)
Insoluble
Solubility in methanol and isopropyl alcohol Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Perfluorotributylamine (PFTBA), also referred to as FC43, is an

butyl groups connected to one nitrogen atom, in which all of the hydrogen atoms are replaced with fluorine atoms. The compound is produced for the electronics industry, along with other perfluoroalkylamines. The high degree of fluorination significantly reduces the basicity of the central amine due to electron-withdrawing effects.[1]

Preparation

It is prepared by electrofluorination of tributylamine using hydrogen fluoride as solvent and source of fluorine:[2]

N(CH2CH2CH2CH3)3 + 27 HF → N(CF2CF2CF2CF3)3 + 27 H2

Uses

The compound has two commercial uses. It is used as an ingredient in

Fluosol, artificial blood. This application exploits the high solubility of oxygen and carbon dioxide in the solvent, as well as the low viscosity and toxicity.[3] It is also a component of Fluorinert coolant liquids. CPUs of some computers are immersed in this liquid to facilitate cooling.[2]

Niche

The compound is used as a calibrant

atomic mass units
.

Safety

Fluorofluids are generally of very low toxicity, so much that they have been evaluated as synthetic blood.[2]

Environmental impact

It is a greenhouse gas with warming properties more than 7,000 times that of carbon dioxide over a 100-year period,[5][6] and, as such, is one of the most potent greenhouse gasses ever discovered.[7] Its concentration in the atmosphere is approximately 0.18 parts per trillion. The compound can persist in the atmosphere for up to 500 years. Sulfur hexafluoride, however, has a GWP of 23,900,[8] which would make it much more powerful.

See also

References

  1. ^ "Tuning basicity | Cambridge MedChem Consulting". www.cambridgemedchemconsulting.com. Retrieved 2020-08-11.
  2. ^
    ISBN 978-0-471-23896-6
    .
  3. S2CID 38969204
    .
  4. ISBN 978-0-9882761-0-9, [1]
    ., Nov. 2012.
  5. S2CID 130690897
    .
  6. ^ Goldenberg, Suzanne (10 December 2013). "Newly discovered greenhouse gas '7,000 times more powerful than CO2'". The Guardian. Retrieved 11 December 2013.
  7. ^ Goldenberg, Suzanne (11 December 2013). "Newly Discovered Greenhouse Gas "7,000 Times More Powerful than CO2"". Mother Jones. Retrieved 12 December 2013.
  8. ^ "2.10.2 Direct Global Warming Potentials". Intergovernmental Panel on Climate Change. 2007. Retrieved 22 February 2013.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Perfluorotributylamine&oldid=1206264748"