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2-Fluoroethanol was originally synthesized by treating 2-chloroethanol with potassium fluoride, in a simple Finkelstein reaction. [5] The product has a lower boiling point that the starting material and may be conveniently isolated by distillation.
Aerobic biotransformation pathways of 8:2 FTOH in soil [10] The fluorotelomer alcohols 6:2 FTOH and 8:2 FTOH have been found to be estrogenic. [11] 10:2 fluorotelomer alcohol (10:2 FTOH) The atmospheric oxidation of fluorotelomer alcohols can also result in anthropogenic perfluorinated carboxylic acids. [12]
Pentafluorophenol is the organofluorine compound (specifically a fluoroalcohol) with the formula C 6 F 5 OH. This is the perfluorinated analogue of phenol. It is a white solid that melts just above room temperature, and smells of phenol. With a pK a of 5.5, it is one of the most acidic phenols.
Nonafluoro-tert-butyl alcohol (IUPAC name: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol) is a fluoroalcohol. It is the perfluorinated analog of tert-butyl alcohol. Notably, as a consequence of its electron withdrawing fluorine substituents, it is very acidic for an alcohol, with a pK a value of 5.4, similar to that of a carboxylic acid.
Hexafluoro-propan-2-ol is a speciality solvent for organic synthesis, particularly for reactions involving oxidations and strong electrophiles. For example, HFIP enhances the reactivity of hydrogen peroxide as applied to Baeyer-Villiger oxidation of cyclic ketones. [ 1 ]
Other biologically synthesized organofluorines include ω-fluoro fatty acids, fluoroacetone, and 2-fluorocitrate which are all believed to be biosynthesized in biochemical pathways from the intermediate fluoroacetaldehyde. [26] Adenosyl-fluoride synthase is an enzyme capable of biologically synthesizing the carbon–fluorine bond. [28]
The Ziegler alcohol synthesis involves oligomerization of ethylene using triethylaluminium followed by oxidation. [2] The triethylaluminium is produced by action of aluminium, ethylene, and hydrogen gas. In the production process, two-thirds of the triethylaluminium produced is recycled back into the reactor, and only one-third is used to ...