1-bromo-1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same reactor as in Example 1 was used. Into the flask was placed 200 ml (747 mM) of perfluorooctyl iodide (PFOI), which was then heated at 160° C. and irradiated with a 400-W high-pressure mercury lamp. After the reaction mixture started to reflux, 54.5 ml (1.07M) of bromine was added dropwise to the mixture at a rate of 0.4 ml/min over a period of about 2 hours. The resulting IBr was drawn off at a suitable time through the IBr withdrawing Dimroth condenser. The reaction was continued for 3 hours, and the reaction mixture was thereafter cooled and washed with a 5% aqueous solution (200 ml) of sodium hydroxide, giving 349.0 g (93.6% in yield) of perfluorooctyl bromide. to reflux the reaction mixture was thereafter cooled washed with a 5% aqueous solution (200 ml) of sodium hydroxide

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same reactor as in Example 1 was used. Into the flask was placed 200 ml (747 mM) of perfluorooctyl iodide (PFOI), which was then heated at 160° C. and irradiated with a 400-W high-pressure mercury lamp. After the reaction mixture started to reflux, 54.5 ml (1.07M) of bromine was added dropwise to the mixture at a rate of 0.4 ml/min over a period of about 2 hours. The resulting IBr was drawn off at a suitable time through the IBr withdrawing Dimroth condenser. The reaction was continued for 3 hours, and the reaction mixture was thereafter cooled and washed with a 5% aqueous solution (200 ml) of sodium hydroxide, giving 349.0 g (93.6% in yield) of perfluorooctyl bromide. to reflux the reaction mixture was thereafter cooled washed with a 5% aqueous solution (200 ml) of sodium hydroxide

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

Procedure: With reference to FIG. 1, and H-shaped tube equipped with a Dimroth condenser and a Dimroth condenser having an IBr withdrawing cock was attached to a 500-ml four-necked flask. Into the flask were placed 200 ml (747 mM) of perfluorooctyl iodide (PFOI) and 5.0 ml (97.1 mM) of bomine, and the mixture was heated at 150° to 155° C. and irradiated with a 500-W visible light lamp. After the reaction mixture started to reflux, 49.5 ml (972 mM) of bromine was added dropwise to the mixture at a rate of 0.2 ml/min over a period of about 4 hours. The resulting IBr was drawn off at a suitable time through the IBr withdrawing Dimroth condenser. The reaction was continued for 5 hours, and the reaction mixture was thereafter cooled and washed with a 5% aqueous solution (200 ml) of sodium hydroxide to obtain 344.9 g (92.5% in yield) of perfluorooctyl bromide. With reference to FIG. 1, and H-shaped tube equipped with a Dimroth condenser was attached to a 500-ml four-necked flask the mixture was heated at 150° to 155° C. irradiated with a 500-W visible light lamp to reflux the reaction mixture was thereafter cooled washed with a 5% aqueous solution (200 ml) of sodium hydroxide

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

Procedure: With reference to FIG. 1, and H-shaped tube equipped with a Dimroth condenser and a Dimroth condenser having an IBr withdrawing cock was attached to a 500-ml four-necked flask. Into the flask were placed 200 ml (747 mM) of perfluorooctyl iodide (PFOI) and 5.0 ml (97.1 mM) of bomine, and the mixture was heated at 150° to 155° C. and irradiated with a 500-W visible light lamp. After the reaction mixture started to reflux, 49.5 ml (972 mM) of bromine was added dropwise to the mixture at a rate of 0.2 ml/min over a period of about 4 hours. The resulting IBr was drawn off at a suitable time through the IBr withdrawing Dimroth condenser. The reaction was continued for 5 hours, and the reaction mixture was thereafter cooled and washed with a 5% aqueous solution (200 ml) of sodium hydroxide to obtain 344.9 g (92.5% in yield) of perfluorooctyl bromide. With reference to FIG. 1, and H-shaped tube equipped with a Dimroth condenser was attached to a 500-ml four-necked flask the mixture was heated at 150° to 155° C. irradiated with a 500-W visible light lamp to reflux the reaction mixture was thereafter cooled washed with a 5% aqueous solution (200 ml) of sodium hydroxide

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

Procedure: Perfluorononanoic acid 100 g (0.215 mole), bromine 21.0 g (0.129 mole) and Freon 113 (500 ml) were mixed in the plastic reactor. The mixture was treated with fluorine in the same manner as described in Example 1. Approximately 1.7 fold excess fluorine was used, producing 92 grams of perfluorooctyl bromide (86% yield). Thus, using approximately half the amount of bromine as used in Example 1 produced a lower yield of the perfluoroalkyl halide.

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

Procedure: Perfluorononanoic acid 100 g (0.215 mole), bromine 21.0 g (0.129 mole) and Freon 113 (500 ml) were mixed in the plastic reactor. The mixture was treated with fluorine in the same manner as described in Example 1. Approximately 1.7 fold excess fluorine was used, producing 92 grams of perfluorooctyl bromide (86% yield). Thus, using approximately half the amount of bromine as used in Example 1 produced a lower yield of the perfluoroalkyl halide.

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Perfluorononanoic acid 100 g (0.215 mole), bromine 41 g (0.258 mole) and Freon 113 (500 ml) were mixed in a 2-liter Teflon plastic bottle. This plastic reactor was equipped with a Teflon-coated magnetic stir bar, inlet and outlet tubes made of Teflon-FEP, and a thermocouple coated with Teflon-FEP. The outlet tube was connected to a condensor which was chilled with an ethylene glycol-water mixture. The acid solution was warmed to 30 ° C. through agitation while the reactor was purged of air by flushing it with an inert gas, such as nitrogen, through the inlet tube; The nitrogen flow was terminated and fluorine gas was bubbled into the mixture at 30 cc/min. The fluorine, supplied by Air Products, was used without further purification. The fluorine flow rate was controlled with a Monel needle valve and monitored with a Hastings mass flow transducer. Despite an exothermic reaction occurring immediately, the reaction temperature was kept at 30°-40° C. throughout the reactor by external cooling. The fluorine flow was maintained until the color of the solution turned from deep red to light yellow. Approximately 2.2 fold excess of fluorine (based on the initial amount of acid used) was required to produce this result. After the fluorine gas was terminated, the reactor was again purged with nitrogen and the mixture was carefully poured into water. The organic precipitate was washed with water containing a small amount of sodium thiosulfite, and then dried over magnesium sulfate. Fractional distillation of the precipitate produced 100 grams of perfluorooctyl bromide (97% yield) having a boiling point between 142°-144° C. This plastic reactor was equipped with a Teflon-coated magnetic stir bar, inlet and outlet tubes was purged of air by flushing it with an inert gas The nitrogen flow was terminated fluorine gas was bubbled into the mixture at 30 cc/min was used without further purification Despite an exothermic reaction was kept at 30°-40° C. throughout the reactor by external cooling to produce this result After the fluorine gas was terminated the reactor was again purged with nitrogen the mixture was carefully poured into water The organic precipitate was washed with water containing a small amount of sodium thiosulfite dried over magnesium sulfate Fractional distillation of the precipitate

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

Procedure: The protocol of Example 1 was repeated to form four additional emulsions, except that in successive emulsions, the fluorocarbon was perfluorooctyl bromide containing 1%, 2%, 5%, and 10% perfluorodecyl bromide (w/w), respectively. to form four additional emulsions

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

Procedure: 13.0 g (0.09 mol) of finely ground copper bromide of the formula CuBr are put into a bomb tube of capacity 25 cm3 and made of glass, and are subjected to a temperature of 200° C. under a pressure of 10 Pa for 4 hours, in order to remove residual water. After the bomb tube has cooled to room temperature, anhydrous nitrogen is passed into it and 16.4 g (0.03 mol) of perfluorooctyl iodide are added, and the bomb tube is sealed by fusion and shaken for 50 hours at 240° to 250° C. 3 mol of bromide ions are employed per mol of bound iodine atom. When the reaction is complete, the bomb tube is opened and the organofluorine products are distilled out of the bomb tube by heating at 200° C. This gives 12.8 g of distillate which, according to analysis by gas chromatography is composed of 97.7% by weight of perfluorooctyl bromide; 1.9% by weight of unreacted perfluorooctyl iodide and 0.3% by weight of CF3 (CF2)7H. This corresponds to a yield of 83.5% of perfluorooctyl bromide, relative to perfluorooctyl iodide employed. to remove residual water are added the bomb tube is sealed by fusion the organofluorine products are distilled out of the bomb tube by heating at 200° C

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

Procedure: A tobramycin sulfate dry powder composition is prepared according to the following procedure. Sterile Water for Irrigation (SWFI) is heated above the gel to liquid crystal temperature (about 80° C.) of disteroyl phosphatidylcholine (DSPC). DSPC and calcium chloride dihydrate are then added to the heated water. The resulting lipid dispersion is mixed in an UltraTurrax T-50 (IKA Labortechnik) at 8,000 rpm for 5 min. Perfluorooctyl bromide (PFOB) is then added dropwise (15 ml/min) to the lipid dispersion under mixing. After the addition is complete the resulting PFOB-in-water emulsion is mixed for an additional 10 min at 10,000 rpm. Emulsification in the UltraTurrax produces droplets in the micron-size range. Tobramycin sulfate is then dissolved in the continuous phase of the emulsion and the resulting dispersion is used as the feedstock for spray drying. The feedstock is then spray dried to obtain a dry powder formulation having the composition set forth in Table 1 below. A tobramycin sulfate dry powder composition is prepared The resulting lipid dispersion is mixed in an UltraTurrax T-50 (IKA Labortechnik) at 8,000 rpm for 5 min under mixing After the addition is mixed for an additional 10 min at 10,000 rpm Emulsification in the UltraTurrax produces droplets in the micron-size range drying The feedstock is then spray dried to obtain a dry powder formulation