Liquid-phase fluorination

A method for replacing essentially all of the hydrogen atoms of a hydrogen-containing compound by liquid-phase fluorination, comprising the steps of:

• a) providing a fluorination reactor, wherein the reactor comprises a reaction vessel having means for agitating a liquid contained therein, means for introducing the hydrogen-containing compound into the liquid, means for introducing a gas into the liquid, means for removing a vaporized liquid from the reaction vessel operatively linked to means for condensing the vaporized liquid, and means for returning the condensed liquid to the reaction vessel;
• b) introducing fluorine gas into an inert liquid medium;
• c) directing the hydrogen-containing compound in the inert liquid medium in the reaction vessel to form a turbulent inert liquid medium so that the hydrogen-containing compound is dispersed or dissolved within the inert liquid medium;
• d) fluorinating the hydrogen-containing compound, the amount of fluorine gas being in excess of the stoichiometric amount necessary to replace the hydrogen atoms in the hydrogen-containing compound and wherein the fluorine gas is in a concentration low enough so that the vapor of the inert liquid medium and fluorine do not form a flammable mixture during fluorination;
• and
• e) continuing the fluorination reaction until essentially all of the hydrogen atoms of the hydrogen-containing compound are replaced with fluorine atoms without substantial concurrent oligomerization and/or polymerization of the hydrogen-containing compound.

A process for forming a perfluorinated organic compound which comprises the steps of:

• a) providing a reaction system comprising a reactor and a means for conveying a fluid through the reactor;
• b) conveying through the reactor a turbulent fluid comprising an organic compound, which can be fluorinated to from the perfluorinated organic compound, and an inert liquid medium;
• c) introducing fluorine gas into the turbulent fluid, the ratio of organic compound to fluorine being sufficient to obtain a chemical reaction between them;
• and
• d)fluorinating the organic compound in the turbulent fluid, wherein the fluorine gas is in a concentration low enough so that the vapor of the inert liquid medium and fluorine do not form a flammable mixture while fluorinating and for a time sufficient to yield the perfluorinated compound without substantial oligomerization and/or polymerization of the organic compound.

A fluorination method for replacing essentially all of the hydrogen atoms of a hydrogen-containing compound with fluorine atoms, comprising the steps of:

• a) introducing fluorine gas into an liquid medium, wherein a turbulent liquid medium is established, said liquid medium selected from the group consisting of a perfluorocarbon, chlorofluorocarbon, chlorofluoroether and a mixture of perfluoro(2-n-butyltetrahydrofuran) and perfluoro(2-n-propyltetrahydrofuran);
• b) introducing the hydrogen-containing compound into the turbulent liquid medium so that the hydrogen-containing compound is dissolved or dispersed within the turbulent liquid medium;
• c) fluorinating the hydrogen-containing compound present in the turbulent liquid medium under fluorination conditions, the fluorination conditions being sufficient to replace hydrogen atoms in the hydrogen-containing compound with fluorine atoms and the fluorine being diluted to a concentration low enough so that the vapor of the liquid medium and fluorine do not form a flammable mixture under fluorination conditions;
• and
• d) continuing the introduction of fluorine gas under the fluorination conditions until essentially all of the hydrogen atoms of the hydrogen-containing compound have been replaced with fluorine atoms without substantial oligomerization and/or polymerization of the hydrogen-containing compound.