Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2000-05-26
2001-07-17
Richter, Johann (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S411000
Reexamination Certificate
active
06262312
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a process for producing 1,1,1-trifluoroacetone that is useful as an intermediate of pharmaceuticals and agricultural chemicals, or as a reagent for introducing fluorine-containing groups.
1,1,1-trifluoroacetone is known to be obtained by various methods. It is described in J. Chem. Soc. (Lond.) 1956, 835 that 1,1,1-trifluoroacetone is synthesized by a Grignard reaction between trifluoroacetic acid and magnesium methyliodide. This Grignard reaction must be conducted in an anhydrous state. In addition, it is also described in Tetrahedron, 20, 2163 (1964) that trifluoroacetone can be synthesized by decarbonating trifluoroacetoethyl acetate in sulfuric acid. It is described in Tetrahedron Lett. Vol. 24 (No. 5), 507-510, 1983 that difluoromethylketones are obtained at considerably high yield as a result of reducing chlorodifluoroketones, which are represented by CF
2
ClC(═O)R (wherein R is a group not containing halogen) by zinc and methanol in tetrahydrofuran.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a process for easily producing 1,1,1-trifluoroacetone from a raw material, which is easily available, such as a chlorofluorinated acetone.
According to the present invention, there is provided a process for producing 1,1,1-trifluoroacetone. This process includes reacting a halogenated acetone with a metal in the presence of a proton donor. This halogenated acetone is represented by the general formula (1):
where X represents a chlorine atom, bromine atom or iodine atom, and n represents an integer from 1 to 3.
According to the present invention, it is possible to obtain 1,1,1-trifluoroacetone by the above-mentioned simple procedure from the halogenated acetone, which is easily available.
REFERENCES:
patent: 4060555 (1977-11-01), Peterson et al.
patent: 5093532 (1992-03-01), Baasner et al.
patent: 5481029 (1996-01-01), Braun et al.
Sykes et al., “a New Synthesis of Fluoro-ketones”, J. Chem. Soc., pp. 835-839 (1956).
Burdon et al., “the sodium-Promoted claisen Ester Condensations of Ethyl Perfluoroalkanecarboxylates”, Tetrahedron, vol. 20, pp. 2163-2166 (1964).
Yamana et al., “A Convenient Synthesis of 2,2-Difluoro Enol Silyl Ethers from Chlorodifluoromethyl Ketones”, & Tetrahedron, vol. 24, No. 5 p 507-510 (1983).
Central Glass Company Limited
Crowell & Moring , L.L.P.
Richter Johann
Witherspoon Sikarl A.
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