1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane

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

Procedure: Solvency tests with 50% by volume 4-bromo-3-chloro-3,4,4-trifluorobutene and 50% by volume ethyl nonafluorobutyl ether were performed. The solvency characteristics of these mixtures matched or exceeded that of CFC-113 with Krytox and Jet Lube. The solvency of the individual components was inferior to that of CFC-113 toward Krytox and Jet Lube, illustrating the effectiveness of using mixtures as taught by this invention. Similarly, mixtures of 4-bromo-3,3,4,4-trifluorobutene and methyl nonafluorobutyl ether produced solvency characteristic that met or exceeded those of CFC-113.

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

Procedure: Using essentially the procedure as in Example 1, a mixture of perfluorobutyric acid fluorides (3.77 g with acyl fluoride content of 81%, 14 mmol), KF (1.02 g ,17 mmol), the ethoxyisobutene (4.56 g with purity 88%, 0.18 mmol) in 8.33 g diglyme was agitated at room temperature for four days. The reactor was vented to yield 0.67 g liquid which comprised (GC %): 88% starting acyl fluorides mixture and 8% C4F9OC2H5. The reaction solution remaining in the reactor was vacuum distilled to yield 3.0 g of a mixture which comprised (GC %): 75% C4F9OC2H5, 1.5% C2H5C(CF3)2C(O)F and 7.6% starting vinyl ether. After decarboxylation by treatment with triethylamine, the remaining diglyme solution yielded 1.45 g CF3CH2CF3 (purity 98% contaminated with 1.5% C4F9OC2H5 and 0.5% (CF3)CC2H5C(O)F). Triethylamine recovery gave 2.5 g organic liquid material with b.p. up to 101° C., consisting of (GC %): 2.5% CF3CH2CF3, 42% triethylamine, 9% starting vinyl ether and 29% diglyme. Calculated yields were: C4F9OC2H5, 72% on the consumed acid fluoride mixture, CF3CH2CF3, 75% on consumed vinyl ether.

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

Procedure: Using essentially the procedure as in Example 1, a mixture of perfluorobutyric acid fluorides (3.77 g with acyl fluoride content of 81%, 14 mmol), KF (1.02 g ,17 mmol), the ethoxyisobutene (4.56 g with purity 88%, 0.18 mmol) in 8.33 g diglyme was agitated at room temperature for four days. The reactor was vented to yield 0.67 g liquid which comprised (GC %): 88% starting acyl fluorides mixture and 8% C4F9OC2H5. The reaction solution remaining in the reactor was vacuum distilled to yield 3.0 g of a mixture which comprised (GC %): 75% C4F9OC2H5, 1.5% C2H5C(CF3)2C(O)F and 7.6% starting vinyl ether. After decarboxylation by treatment with triethylamine, the remaining diglyme solution yielded 1.45 g CF3CH2CF3 (purity 98% contaminated with 1.5% C4F9OC2H5 and 0.5% (CF3)CC2H5C(O)F). Triethylamine recovery gave 2.5 g organic liquid material with b.p. up to 101° C., consisting of (GC %): 2.5% CF3CH2CF3, 42% triethylamine, 9% starting vinyl ether and 29% diglyme. Calculated yields were: C4F9OC2H5, 72% on the consumed acid fluoride mixture, CF3CH2CF3, 75% on consumed vinyl ether.

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

Procedure: Using essentially the procedure as in Example 1, a mixture of perfluorobutyric acid fluorides (3.77 g with acyl fluoride content of 81%, 14 mmol), KF (1.02 g ,17 mmol), the ethoxyisobutene (4.56 g with purity 88%, 0.18 mmol) in 8.33 g diglyme was agitated at room temperature for four days. The reactor was vented to yield 0.67 g liquid which comprised (GC %): 88% starting acyl fluorides mixture and 8% C4F9OC2H5. The reaction solution remaining in the reactor was vacuum distilled to yield 3.0 g of a mixture which comprised (GC %): 75% C4F9OC2H5, 1.5% C2H5C(CF3)2C(O)F and 7.6% starting vinyl ether. After decarboxylation by treatment with triethylamine, the remaining diglyme solution yielded 1.45 g CF3CH2CF3 (purity 98% contaminated with 1.5% C4F9OC2H5 and 0.5% (CF3)CC2H5C(O)F). Triethylamine recovery gave 2.5 g organic liquid material with b.p. up to 101° C., consisting of (GC %): 2.5% CF3CH2CF3, 42% triethylamine, 9% starting vinyl ether and 29% diglyme. Calculated yields were: C4F9OC2H5, 72% on the consumed acid fluoride mixture, CF3CH2CF3, 75% on consumed vinyl ether.

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

Procedure: Solvency tests with 50% by volume 4-bromo-3-chloro-3,4,4-trifluorobutene and 50% by volume ethyl nonafluorobutyl ether were performed. The solvency characteristics of these mixtures matched or exceeded that of CFC-113 with Krytox and Jet Lube. The solvency of the individual components was inferior to that of CFC-113 toward Krytox and Jet Lube, illustrating the effectiveness of using mixtures as taught by this invention. Similarly, mixtures of 4-bromo-3,3,4,4-trifluorobutene and methyl nonafluorobutyl ether produced solvency characteristic that met or exceeded those of CFC-113.

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

Procedure: Solvency tests with 50% by volume 4-bromo-3-chloro-3,4,4-trifluorobutene and 50% by volume ethyl nonafluorobutyl ether were performed. The solvency characteristics of these mixtures matched or exceeded that of CFC-113 with Krytox and Jet Lube. The solvency of the individual components was inferior to that of CFC-113 toward Krytox and Jet Lube, illustrating the effectiveness of using mixtures as taught by this invention. Similarly, mixtures of 4-bromo-3,3,4,4-trifluorobutene and methyl nonafluorobutyl ether produced solvency characteristic that met or exceeded those of CFC-113.

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

Procedure: Solvency tests with 50% by volume 4-bromo-3-chloro-3,4,4-trifluorobutene and 50% by volume ethyl nonafluorobutyl ether were performed. The solvency characteristics of these mixtures matched or exceeded that of CFC-113 with Krytox and Jet Lube. The solvency of the individual components was inferior to that of CFC-113 toward Krytox and Jet Lube, illustrating the effectiveness of using mixtures as taught by this invention. Similarly, mixtures of 4-bromo-3,3,4,4-trifluorobutene and methyl nonafluorobutyl ether produced solvency characteristic that met or exceeded those of CFC-113.

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

Procedure: Solvency tests with 50% by volume 4-bromo-3-chloro-3,4,4-trifluorobutene and 50% by volume ethyl nonafluorobutyl ether were performed. The solvency characteristics of these mixtures matched or exceeded that of CFC-113with Krytox and Jet Lube. The solvency of the individual components was inferior to that of CFC-113toward Krytox and Jet Lube, illustrating the effectiveness of using mixtures as taught by this invention. Similarly, mixtures of 4-bromo-3,3,4,4-trifluorobutene and methyl nonafluorobutyl ether produced solvency characteristic that met or exceeded those of CFC-113.

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

Procedure: Using essentially the procedure as in Example 1, a mixture of perfluorobutyric acid fluorides (3.77 g with acyl fluoride content of 81%, 14 mmol), KF (1.02 g ,17 mmol), the ethoxyisobutene (4.56 g with purity 88%, 0.18 mmol) in 8.33 g diglyme was agitated at room temperature for four days. The reactor was vented to yield 0.67 g liquid which comprised (GC %): 88% starting acyl fluorides mixture and 8% C4F9OC2H5. The reaction solution remaining in the reactor was vacuum distilled to yield 3.0 g of a mixture which comprised (GC %): 75% C4F9OC2H5, 1.5% C2H5C(CF3)2C(O)F and 7.6% starting vinyl ether. After decarboxylation by treatment with triethylamine, the remaining diglyme solution yielded 1.45 g CF3CH2CF3 (purity 98% contaminated with 1.5% C4F9OC2H5 and 0.5% (CF3)CC2H5C(O)F). Triethylamine recovery gave 2.5 g organic liquid material with b.p. up to 101° C., consisting of (GC %): 2.5% CF3CH2CF3, 42% triethylamine, 9% starting vinyl ether and 29% diglyme. Calculated yields were: C4F9OC2H5, 72% on the consumed acid fluoride mixture, CF3CH2CF3, 75% on consumed vinyl ether.