Perfluorotributylamine Explained

Perfluorotributylamine (PFTBA), also referred to as FC43, is an organic compound with the chemical formula . It is a colorless liquid. A molecule of this chemical compound consists of three 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:

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.[2] It is also a component of Fluorinert coolant liquids. CPUs of some computers are immersed in this liquid to facilitate cooling.

Niche

The compound is used as a calibrant[3] in gas chromatography when the analytical technique uses mass spectrometry as a detector to identify and quantify chemical compounds in gases or liquids. When undergoing ionization in the mass spectrometer, the compound decomposes in a repeatable pattern to form fragments of specific masses, which can be used to tune the mass response and accuracy of the mass spectrometer. Most commonly used ions are those with approximate mass of 69, 131, 219, 414 and 502 atomic mass units.

Safety

Fluorofluids are generally of very low toxicity, so much that they have been evaluated as synthetic blood.[4]

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

Notes and References

  1. Web site: Tuning basicity Cambridge MedChem Consulting. 2020-08-11. www.cambridgemedchemconsulting.com.
  2. Garrelts . J. C. . Fluosol: An oxygen-delivery fluid for use in percutaneous transluminal coronary angioplasty . DICP: The Annals of Pharmacotherapy . 24 . 11 . 1105–1112 . 1990 . 10.1177/106002809002401116 . 2275237. 38969204.
  3. Dunnivant, Frank and Ginsbach, Jake. "Gas Chromatography, Liquid Chromatography, Capillary Electrophoresis – Mass Spectroscopy – A Basic Introduction", Chapter 7,, http://people.whitman.edu/~dunnivfm/C_MS_Ebook/CH7/7_2.html., Nov. 2012.
  4. Encyclopedia: Fluoroethers and Fluoroamines . Michael G. Costello . Richard M. Flynn . John G. Owens . 2001. Wiley-VCH. Weinstein. Kirk-Othmer Encyclopedia of Chemical Technology. 10.1002/0471238961.0612211506122514.a01.pub2. 978-0-471-23896-6.
  5. Hong . A. C. . Young . C. J. . Hurley . M. D. . Wallington . T. J. . Mabury . S. A. . Perfluorotributylamine: A novel long-lived greenhouse gas . 10.1002/2013GL058010 . Geophysical Research Letters . 6010–6015. 2013 . 40. 22 . 2013GeoRL..40.6010H . 130690897 .
  6. Web site: Newly discovered greenhouse gas '7,000 times more powerful than CO2' . . 10 December 2013 . 11 December 2013 . Goldenberg, Suzanne.
  7. Web site: Newly Discovered Greenhouse Gas "7,000 Times More Powerful than CO2" . . 11 December 2013 . 12 December 2013 . Goldenberg, Suzanne.
  8. Web site: 2.10.2 Direct Global Warming Potentials . 2007 . Intergovernmental Panel on Climate Change . 22 February 2013.