Provided is a method of manufacturing octafluorocyclopentene by bringing 1-chloroheptafluorocyclopentene into contact with an alkali metal fluoride. The manufacturing method includes a feedstock heating step of heating 1-chloroheptafluorocyclopentene to not lower than 40 C. and not higher than 55 C. and a fluorination step of maintaining a suspension containing a polar aprotic solvent and an alkali metal fluoride at 85 C. or higher while supplying heated 1-chloroheptafluorocyclopentene into the suspension and performing fluorination thereof to obtain octafluorocyclopentene.

Provided is a manufacturing method in which 1-chloroheptafluorocyclopentene is brought into contact with an alkali metal fluoride to obtain octafluorocyclopentene. The manufacturing method includes a fluorination step of maintaining, at 85 C. or higher, a suspension containing an alkali metal fluoride suspended in a mixed solvent including a polar aprotic solvent and a glycol ether having a higher boiling point than the polar aprotic solvent while supplying 1-chloroheptafluoropentene into the suspension and performing fluorination thereof to obtain octafluorocyclopentene.

Provided is a manufacturing method in which 1-chloroheptafluorocyclopentene is brought into contact with an alkali metal fluoride to obtain octafluorocyclopentene. The manufacturing method includes a fluorination step of maintaining, at 85 C. or higher, a suspension containing an alkali metal fluoride suspended in a mixed solvent including a polar aprotic solvent and a glycol ether having a higher boiling point than the polar aprotic solvent while supplying 1-chloroheptafluoropentene into the suspension and performing fluorination thereof to obtain octafluorocyclopentene.

A manufacturing method of 1-chloro-3,3,3-trifluoropropene (1233zd) is provided. This manufacturing method includes a reaction in which a halogenated hydrocarbon compound having a carbon number of 3 and represented by a general formula (1) is heated:

CF.sub.aCl.sub.3-aCH.sub.2CHF.sub.bCl.sub.2-b(1)

In the formula, a is an integer from 0 to 2, b is 1 or 2 when a=0, b is 0 or 1 when a=1, and b is 0 when a=2.

A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100 C. and 450 C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.

A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100 C. and 450 C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.

The present invention relates to a method for preparing a polyinsaturated perfluorinated compound B from a polyinsaturated perhalogenated compound D having the formula C.sub.nX.sub.2(nm+1), in which X is independently selected from one of the halogens, F, Cl, Br or I, provided at least one X is not fluorine; n is the number of carbon atoms and is at least higher than or equal to 4, m is the number of double carbon-carbon bonds and is higher than or equal to 2, wherein the method comprises a step in which compound D is fluorinated in the presence of a fluorinating agent of general formula AF.sub.p, in which A is hydrogen, an alkali metal or an alkaline earth metal, and p is 1 or 2, and in the presence of an aprotic organic polar solvent; the method being carried out with a molar ratio of AF.sub.p to compound D of less than 1.45*2(nm+1).

The present invention relates to a method for preparing a polyinsaturated perfluorinated compound B from a polyinsaturated perhalogenated compound D having the formula C.sub.nX.sub.2(nm+1), in which X is independently selected from one of the halogens, F, Cl, Br or I, provided at least one X is not fluorine; n is the number of carbon atoms and is at least higher than or equal to 4, m is the number of double carbon-carbon bonds and is higher than or equal to 2, wherein the method comprises a step in which compound D is fluorinated in the presence of a fluorinating agent of general formula AF.sub.p, in which A is hydrogen, an alkali metal or an alkaline earth metal, and p is 1 or 2, and in the presence of an aprotic organic polar solvent; the method being carried out with a molar ratio of AF.sub.p to compound D of less than 1.45*2(nm+1).

A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropopene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100 C. and 450 C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.

A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropopene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100 C. and 450 C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.