Browse Prior Art Database

3,4, 4, 4-Tetrafluorobutan-2-One

IP.com Disclosure Number: IPCOM000097385D
Original Publication Date: 1962-Nov-01
Included in the Prior Art Database: 2005-Mar-07
Document File: 2 page(s) / 14K

Publishing Venue

IBM

Related People

Schumaker, R: AUTHOR [+2]

Abstract

This trifluoroketone, having the formula (Image Omitted) is prepared by hydrolysis and decarboxylation of diethyl (Alpha, Beta, Beta, Beta -tetrafluoropropionyl)-malonate. See page 8, this issue. By stripping HF from the molecule it is possible to produce methyltrifluorovinyl ketone, (Image Omitted) which should be polymerizable to a depolymerizable polymer which would be useful as a photographic film (decomposing upon exposure to light into the gaseous monomer).

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3,4, 4, 4-Tetrafluorobutan-2-One

This trifluoroketone, having the formula

(Image Omitted)

is prepared by hydrolysis and decarboxylation of diethyl (Alpha, Beta, Beta, Beta- tetrafluoropropionyl)-malonate. See page 8, this issue. By stripping HF from the molecule it is possible to produce methyltrifluorovinyl ketone,

(Image Omitted)

which should be polymerizable to a depolymerizable polymer which would be useful as a photographic film (decomposing upon exposure to light into the gaseous monomer).

Preparation of this tetrafluoroketone is as follows:

Diethyi (Alpha, Beta, Beta, Beta -tetrafluoropropionyl)-malonate (102 g, 0. 35 mole) was dissolved in 200 g propionic acid containing 3 g concentrated sulfuric acid. The solution was slowly refluxed through a 40 cm x 2 cm Vigreaux column. The top of the column was connected to a distillation head and to a dry ice- acetone trap. All the distillate boiling below 90 degrees C was collected. When the temperature rose above 90 degrees C (about three hours), the solution was cooled to approximately 50 degrees C and 50 ml 10% sulfuric acid was added and the distillation was continued until the head temperature again rose above 90 degrees C. The wet distillate was extracted with 2-50 ml portions of n-butyl ether. The organic solution was dried over anhydrous sulfate and distilled. A clear colorless product, b.p. 69 to 70 degrees C, nD 1.3136. The yield was 39 g (77%). A sample of the ketone was converted to the 2, 4-dinitrophen...