1,1,1,3,3-pentafluoropropane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The known methods of producing 1,1,1,3,3-pentafluoropropane are as follows. Carbon tetrachloride and vinylidene chloride are prepared and an addition reaction is triggered. The reaction product, 1,1,1,3,3,3-hexachloropropane, is fluorinated to produce 1,1,1,3,3-pentafluoro-3-chloropropane which is reduced with hydrogen to produce 1,1,1,3,3-pentafluoropropane (WO 95/04022). an addition reaction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A method of producing 1,1,1,3,3-pentafluoropropane which comprises reacting 1,1,1,2,2,3,3-heptachloropropane with an alkali metal hydroxide in the presence of a phase transfer catalyst to form 1,1,1,2,3,3-hexachloropropene; continuously reacting, at a constant pressure and in the liquid phase, 1,1,1,2,3,3-hexachloropropene with excess hydrogen fluoride in the presence of at least one of an antimony trihalogenide and an antimony pentahologenide while selectively removing 1,1,1,3,3-pentafluoro-2,3-dichloropropane as it is formed; and reacting gaseous 1,1,1,3,3-pentafluoro-2,3-dichloropropane with hydrogen in the presence of a noble metal catalyst.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A method of producing 1,1,1,3,3-pentafluoropropane which comprises reacting 1,1,1,2,2,3,3-heptachloropropane with an alkali metal hydroxide in the presence of a phase transfer catalyst to form 1,1,1,2,3,3-hexachloropropene; continuously reacting, at a constant pressure and in the liquid phase, 1,1,1,2,3,3-hexachloropropene with excess hydrogen fluoride in the presence of at least one of an antimony trihalogenide and an antimony pentahologenide while selectively removing 1,1,1,3,3-pentafluoro-2,3-dichloropropane as it is formed; and reacting gaseous 1,1,1,3,3-pentafluoro-2,3-dichloropropane with hydrogen in the presence of a noble metal catalyst.

Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The triphenylstannane derivative was prepared using a modified procedure of Brisdon (Chem. Commun. 2002, 2420-2421). Accordingly, 1,1,1,3,3-pentafluoropropane (2.0 g, 14.9 mmol) was condensed into a 500 mL three neck round bottom flask containing ether (20 mL) cooled to −15° C. The mixture was maintained below −10° C. while n-BuLi (2.5 M in hexanes, 16.08 mL, 40.2 mmol) was added. After the reaction was stirred for 10 minutes at −10° C., triphenyl tin chloride (5 g, 13.4 mmol) was added as a solution in ether, maintaining −10° C. The mixture was slowly warmed to room temperature and allowed to stir for an additional 4 hours. An excess of hexanes (300 mL) was added and then the settled mixture was filtered through Celite®. Concentration of the filtered solution in vacuo afforded a pale yellow solid which was purified by column chromatography (SiO2: ether/hexanes, 1:10) affording 5.2 g (78%) of the triphenylstannane derivative as an off white solid. The triphenylstannane derivative was prepared was added maintaining −10° C The mixture was slowly warmed to room temperature to stir for an additional 4 hours the settled mixture was filtered through Celite® Concentration of the filtered solution in vacuo afforded a pale yellow solid which was purified by column chromatography (SiO2: ether/hexanes, 1:10)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reactor described above was cooled and maintained at about 0° C. during the photochlorination reaction. Initially, the reactor was purged of air using nitrogen. Chlorine gas was then introduced to displace the nitrogen. Thereafter, 335 g (2.5 mol) of CF3CH2CHF2 (HFC-245fa) was charged to the reactor. A total of 208 g (2.9 mol) of chlorine gas was bubbled into the CF3CH2CHF2 over a period of about 24 hours while the reactants were being irradiated. At the end of the 24 hour period, GC analysis indicated a 96% conversion of HFC-245fa (retention time 1.9 min) to the desired product HCFC-235fa (retention time 2.1 min). The reaction mixture was washed with 100 mL of a cooled (about 2° C.) solution of aqueous sodium bisulfite (10 wt. %) and distilled (boiling point=26-28° C.) to afford 383 g CF3CH2CF2Cl (yield, 91%). Absent cooling of the wash solution, loss of product by vaporization has been observed due to a slight exotherm during the washing step. No multichlorinated products were detected. The reactor described above was cooled Initially, the reactor was purged of air Chlorine gas was then introduced were being irradiated At the end of the 24 hour period, GC analysis

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The known methods of producing 1,1,1,3,3-pentafluoropropane are as follows. Carbon tetrachloride and vinylidene chloride are prepared and an addition reaction is triggered. The reaction product, 1,1,1,3,3,3-hexachloropropane, is fluorinated to produce 1,1,1,3,3-pentafluoro-3-chloropropane which is reduced with hydrogen to produce 1,1,1,3,3-pentafluoropropane (WO 95/04022). an addition reaction