Hexafluoroisopropanol, commonly abbreviated HFIP is the organic compound with the formula (CF₃)₂CHOH. This fluorinated alcohol finds use as solvent for polymer systems. It appears as a colorless, volatile liquid that is characterized by a strong, pungent odor. As a solvent hexafluoro-2-propanol exhibits strong hydrogen bonding properties enabling it to dissolve substances that serve as hydrogen-bond acceptors, such as amides and ethers. Hexafluoro-2-propanol is also a polar compound, transparent to UV light with high density, low viscosity and low refractive index.

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Production

Hexafluoro-2-propanol is prepared from hexafluoropropylene via hexafluoroacetone, which is reduced by catalytic hydrogenation or by hydride reagents.^[1]

(CF₃)₂CO + H₂ → (CF₃)₂CHOH

Uses

Hexafluoro-2-propanol is a specialty solvent in organic synthesis^[2]^[3] due to its properties which make it especially useful to solubilize a wide range of polymers, including those that are not soluble in the most common organic solvents: such as polyamides, polyacrylonitriles, polyacetals, polyesters (e.g. polyglycolide), and polyketones. Because of its acidity (pK_a = 9.3), it can be used as acid in volatile buffers for ion pair HPLC - mass spectrometry of nucleic acids.^[4] It has also found use in biochemistry to solubilize peptides. Industrially hexafluoro-2-propanol is used as an intermediate for pharmaceuticals (anesthetics) and agrochemicals or as a solvent and cleaner in electronics.

Safety

Hexafluoro-2-propanol is a corrosive and is therefore destructive to tissues of the mucous membranes, upper respiratory tract, skin and eyes, resulting in burns or ulceration. Overexposure by inhalation may result in spasm, inflammation, chemical pneumonitis and larynx, bronchi or pulmonary edema. In case of contact with eyes corneal and conjunctival ulceration or blindness may result. Hexafluoro-2-propanol is not considered carcinogenic, but the effects of a chronic exposure are unknown.

References

Notes

^ Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.
^ Review: Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. Synthesis, 2004,(1), pp. 18-29.
^ Review: Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis , Synthesis 2007, pp. 2925-2943
^ Apffel, A.; Chakel, J.A.; Fischer, S.; Lichtenwalter, K.; Hancock, W.S., Analysis of oligonucleotides by HPLC-electrospray ionization mass spectrometry. Anal. Chem, 1997,(69), pp. 1320-1325.

Sources

Radlick, Phillip C (1982-02-02). Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom. United States Patent 4,314,087. Retrieved on 2006-10-18.

Cheminal, Bernard; H. Mathais and M. Thomarat (1987-03-03). Process for the synthesis of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoroisopropanol. United States Patent 4,647,706. Retrieved on 2006-10-18.

Hexafluoroisopropanol datasheet. DuPont. Retrieved on 2006-10-18.

Categories: Organofluorides | Halogenated solvents | Alcohols

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Hexafluoro-2-propanol