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Electrochemical fluorination (ECF), or electrofluorination, is a foundational organofluorine chemistry method for the preparation of fluorocarbon-based organofluorine compounds. [1] The general approach represents an application of electrosynthesis .
As fluorine is itself manufactured by the electrolysis of hydrogen fluoride, ECF is a rather more direct route to fluorocarbons. The process proceeds at low voltage (5 – 6 V) so that free fluorine is not liberated. The choice of substrate is restricted as ideally it should be soluble in hydrogen fluoride.
Hydrogen fluoride is typically produced by the reaction between sulfuric acid and pure grades of the mineral fluorite: [14] CaF 2 + H 2 SO 4 → 2 HF + CaSO 4 About 20% of manufactured HF is a byproduct of fertilizer production, which generates hexafluorosilicic acid .
Hydrogen bonding amongst HF molecules gives rise to high viscosity in the liquid phase and lower than expected pressure in the gas phase. Hydrogen fluoride does not boil until 20 °C in contrast to the heavier hydrogen halides which boil between −85 °C and −35 °C (−120 °F and –30 °F).
ECF is an electrolysis method whereby the precursor of octanesulfonyl fluoride is electrolyzed in a solution of hydrogen fluoride to give perfluorooctanesulfonyl fluoride. This production method also results in shorter chain perfluoroalkyl substances being formed.
Attack of the hydroxyl group of the substrate on sulfur and elimination of hydrogen fluoride lead to an alkoxyaminosulfur difluoride intermediate. Nucleophilic attack by fluoride, either by an S N 1 [5] or S N 2 [6] pathway, leads to the product. Although clean configurational inversion has been observed in a number of chiral alcohols ...
Fluoroantimonic acid is a mixture of hydrogen fluoride and antimony pentafluoride, containing various cations and anions (the simplest being H 2 F + and SbF − 6).This mixture is a superacid stronger than pure sulfuric acid, by many orders of magnitude, according to its Hammett acidity function.
Fluorocarbons with few C–F bonds behave similarly to the parent hydrocarbons, but their reactivity can be altered significantly.For example, both uracil and 5-fluorouracil are colourless, high-melting crystalline solids, but the latter is a potent anti-cancer drug.