Process for preparing aliphatic fluorofomates

Details Process for preparing aliphatic fluorofomates Process for preparing aliphatic fluorofomates

2005-02-22

2005-02-22

Killos, Paul J. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

06858751

ABSTRACT:
A method for the production of aliphatic fluoroformates, wherein carbonyl fluoride is made to react with aliphatic alcohol in the presence of sodium fluoride in ether at a temperature of −20° to 50° C. The method is carried out using carbonyl fluoride obtained by reacting phosgene with surplus powdered sodium fluoride, whereby the grains thereof have a specific surface of 0.1 m2/g or more and/or an average diameter of 20 μm or less, at a temperature ranging from 25° to 120° C. The method enables unstable fluoroformates such as tertiobutyl to be obtained with excellent yields.

REFERENCES:
patent: 3088975 (1963-05-01), Fawcett et al.
patent: 4612143 (1986-09-01), Piteau et al.
patent: 1214009 (1970-11-01), None
patent: 1216639 (1970-12-01), None
“An Efficient and Convenient Synthesis of Fluoroformates and Carbamoyl Fluorides”, Cuomo, et al, J. Org. Chem., vol. 44, No. 6, 1979, p. 1016.
“Alpha Fluorinated Ethers II Alkyl Fluoroalkyl Ethers”, Aldrich et al., J. Org. Chem., vol. 29, No. 1, 1964, pp 11-15.
“The Chemistry of Carbonyl Fluoride. I. The Fluorination of Organic Compounds”, Fawcett et al, J. Amer. Chem. Soc., vol. 84, No. 22, 1962, pp. 4275-4286.
“Useful Syntheses of Fluoroformates and l-Alkenyl Carbonates”, Vu Anh Dang, Penn. State Univ., 1986, Thesis.

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