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Trifluoroacetic acid in a beaker. TFA is the precursor to many other fluorinated compounds such as trifluoroacetic anhydride, trifluoroperacetic acid, and 2,2,2-trifluoroethanol. [4] It is a reagent used in organic synthesis because of a combination of convenient properties: volatility, solubility in organic solvents, and its strength as an ...
Trifluoroperacetic acid (trifluoroperoxyacetic acid, TFPAA) is an organofluorine compound, the peroxy acid analog of trifluoroacetic acid, with the condensed structural formula CF 3 COOOH . [ Note 1 ] It is a strong oxidizing agent for organic oxidation reactions, such as in Baeyer–Villiger oxidations of ketones . [ 1 ]
Trifluoroacetic acid is a widely employed acid, used for example in the synthesis of peptides.Its esters are useful in analytical chemistry. Longer-chain perfluoroalkyl carboxylic acids, e.g. with five to nine carbons, are useful fluorosurfactants and emulsifiers used in the production of polytetrafluoroethylene (Teflon) and related fluoropolymers.
Trifluoroacetic anhydride was originally prepared by the dehydration of trifluoroacetic acid with phosphorus pentoxide. [2] The dehydration might also be carried out with excess α-halogenated acid chlorides. For example, with dichloroacetyl chloride: [3] 2 CF 3 COOH + Cl 2 CHCOCl → (CF 3 CO) 2 O + Cl 2 CHCOOH + HCl
With a pK a of 0.23 for trifluoroacetic acid, the trifluoroacetate ion is an extremely weak base compared to acetic acid, which has a pK a of 4.76. This is due to the electron-withdrawing effect of the three fluorine atoms adjacent the carboxylate group.
Trifluoroethanol is produced industrially by hydrogenation or the hydride reduction of derivatives of trifluoroacetic acid, such as the esters or acyl chloride. [1]TFE can also be prepared by hydrogenolysis of compounds of generic formula CF 3 −CHOH−OR (where R is hydrogen or an alkyl group containing from one to eight carbon atoms), in the presence of a palladium containing catalyst ...
The compound can be prepared by reaction of iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid in a method analogous to the synthesis of (diacetoxyiodo)benzene: [1] It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid: [2]
The trifluoroacetic acid then forms trifluoroacetate (TFA), a salt of trifluoroacetic acid, in water and on the ground. Due to its high polarity and low degradability, it is difficult to remove TFA from drinking water (ICPR 2019).
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