(Z)-1,3,3,3-tetrafluoroprop-1-ene

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

Procedure: WO 2008/054781 describes a preparation of HFO-1234yf by reaction of 2,3-dichloro-1,1,1-trifluoropropane (HFC-243db) in the presence of HF over a catalyst, in particular 98/2 Cr/Co. The reaction products comprise HFO-1234yf and 2-chloro-3,3,3-trifluoro-1-propene (HCFO-1233xf), the latter product being predominant; the other products 1-chloro-3,3,3-trifluoro-1-propene (HCFO-1233zd) and also 1,1,1,2,2-pentafluoropropane (HFC-245cb) and 1,3,3,3-tetrafluoro-1-propene (HFO-1234ze) are also formed. A higher temperature favors the production of the 1233zd isomer. The starting material, 2,3-dichloro-1,1,1-trifluoropropane (HFC-243db), is indicated as being obtained by chlorination of trifluoro-1-propene (TFP).

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

Procedure: WO 2008/054781 describes a preparation of HFO-1234yf by reaction of 2,3-dichloro-1,1,1-trifluoropropane (HFC-243db) in the presence of HF over a catalyst, in particular 98/2 Cr/Co. The reaction products comprise HFO-1234yf and 2-chloro-3,3,3-trifluoro-1-propene (HCFO-1233xf), the latter product being predominant; the other products 1-chloro-3,3,3-trifluoro-1-propene (HCFO-1233zd) and also 1,1,1,2,2-pentafluoropropane (HFC-245cb) and 1,3,3,3-tetrafluoro-1-propene (HFO-1234ze) are also formed. A higher temperature favors the production of the 1233zd isomer. The starting material, 2,3-dichloro-1,1,1-trifluoropropane (HFC-243db), is indicated as being obtained by chlorination of trifluoro-1-propene (TFP).

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

Procedure: Under nitrogen, into a quartz tube equipped with a dry-ice condenser was added anhydrous methanol (20 g, 0.62 mol) and di-tertiarybutylperoxide (.79 g, 0.003 mol). The quartz tube was placed in a Rayonet UV photochemical reactor and HFC 1234zc, CF3CH═CFH (5 g, 0.044 mol) was added drop-wise via a dry-ice condenser (−78° C.) over a period of ˜1 hour while being irradiated at (UV wavelength) 254 nm. After complete addition, the reaction mixture was irradiated for ˜1 hour. The reaction mixture was concentrated under reduced pressure. The residue was extracted in diethyl ether (˜50 mL), washed with 20 mL aq. Na2SO3 (20%) and brine (10 mL). The ether layer was then concentrated to afford 7 g of the crude material. Distillation of this material under reduced pressure (24-28 mm Hg) afforded CF3CH2CFHCH2OH (2.7g) as a colorless liquid; yield=42% based on HFC 1234 zc. Boiling point, 58° C./24 mm Hg. GC-MS: m/e at 146 (C4H6F4O) for M+; 19 F and 1H NMR spectra are consistent with the structure. 19 F NMR (CDCl3)δ=−64.6 (3F, m), −191.2 (1F, m) ppm; 1H NMR (CDCl3)δ=2.2 (1H, br), 2.4(1H, m), 2.6 (1H, m), 3.7-3.9 (2H, m), 4.9 (1H, dm) ppm. Under nitrogen, into a quartz tube equipped with a dry-ice condenser was added drop-wise via a dry-ice condenser (−78° C.) over a period of ˜1 hour while being irradiated at (UV wavelength) 254 nm After complete addition the reaction mixture was irradiated for ˜1 hour The reaction mixture was concentrated under reduced pressure The residue was extracted in diethyl ether (˜50 mL) washed with 20 mL aq. Na2SO3 (20%) and brine (10 mL) The ether layer was then concentrated to afford 7 g of the crude material Distillation of this material under reduced pressure (24-28 mm Hg)

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

Procedure: WO 2008/054781 describes a preparation of HFO-1234yf by reaction of 2,3-dichloro-1,1,1-trifluoropropane (HFC-243db) in the presence of HF over a catalyst, in particular 98/2 Cr/Co. The reaction products comprise HFO-1234yf and 2-chloro-3,3,3-trifluoro-1-propene (HCFO-1233xf), the latter product being predominant; the other products 1-chloro-3,3,3-trifluoro-1-propene (HCFO-1233zd) and also 1,1,1,2,2-pentafluoropropane (HFC-245cb) and 1,3,3,3-tetrafluoro-1-propene (HFO-1234ze) are also formed. A higher temperature favors the production of the 1233zd isomer. The starting material, 2,3-dichloro-1,1,1-trifluoropropane (HFC-243db), is indicated as being obtained by chlorination of trifluoro-1-propene (TFP).