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AssigneeMassachusetts Institute of Technology
InventorsRichard J. Lagow, James L. Adcock, Norma J. Maraschin
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An apparatus and process useful in direct fluorination of a variety of compositions, as well as the fluorinated compositions themselves, are disclosed. The apparatus comprises a cryogenic zone reactor, such as a packed column reactor, suitably divided into a plurality of independently controllable cryogenic temperature zones. Means are also provided to introduce a reactant to be fluorinated as well as to introduce a mixture of fluorine gas and an inert gas. New fluorinated compounds are also disclosed. These include: perfluoro-2-methoxyethyl ether; perfluoro-1,4-dioxane; perfluoro-2,5-diketohexane; perfluorohexamethylethane; and monohydropentadecafluoroadamantane. Additionally, new syntheses for trifluoroacetic acid, a commercially significant bulk chemical, are disclosed. One synthesis comprises producing perfluorooethyl acetate by direct fluorination using a cryogenic zone reactor, followed by hydrolysis of perfluoroethyl acetate. Two moles of the acid are produced for each mole of ester. A second synthesis comprises fluorinating an acyl chloride followed by hydrolysis of the resulting acyl fluoride.
A process for synthesizing trifluoroacetic acid comprising:
A direct fluorination process for producing trifluoroacetic acid, comprising:
A cryogenic direct fluorination process comprising contacting, at a first fluorination site, a source of elemental fluorine and ethyl acetate at a temperature below the condensation point of said ethyl acetate and in the presence of a fluorination surface capable of removing heat generated during fluorination whereby said ethyl acetate is partially fluorinated, warming said first fluorination site to a temperature at which said partially fluorinated ethyl acetate volatilizes whereby it is volatilized and passes to a fresh fluorination site, lowering the temperature of said fresh fluorination site below the condensation point of said partially fluorinated ethyl acetate and contacting the partially fluorinated ethyl acetate, at said fresh site, with a source of elemental fluorine in the presence of a fluorination surface capable of removing heat generated during fluorination, repeating the warming, condensation and contacting step until said ethyl acetate is perfluorinated to produce perfluoroethyl acetate and subsequently hydrolyzing said perfluoroethyl acetate to produce trifluoroacetic acid.
Dependencies are inferred from the claim text.