Methyl perfluorooctanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The beta-diketones which are used in carrying out this invention can be prepared by perfluoroacylation of appropriate ketones by esters or acid chlorides of perfluorocarboxylic acids, as in the reaction of methyl perfluorocaprylate with methyl tertiary butyl ketone to make 1-perfluoroheptyl-3 tertiary butyl-1,3 propanedione. Or a methyl perfluoroalkyl ketone can be acylated by an appropriate carboxylic derivative, as in the reaction of methyl phenylacetate with methyl perfluoropentyl ketone to give 1-perfluoropentyl-3-phenyl-1,3-propanedione; or in order to have two perfluorinated groups in the eventual isoxazoline, a methyl ketone containing also a perfluoroalkyl group can be acylated by an ester of a perfluorinated carboxylic acid, as when methyl perfluorocaprylate is reacted with methyl perfluoroheptyl ketone to produce 1,3-di(perfluoroheptyl)-1,3-propanedione.

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

Procedure: C7F15C(O)N(CH3)C2H4OH was prepared by combining n-C7F15CO2CH3 (85 grams) and CH3NHCH2CH2OH (16.5 grams) in THF (50 grams) at 50° C. Progress of the reaction was monitered by GC and FTIR spectra. The isolated yield was 76.4% of C7F15C(O)N(CH3)C2H4OH. (b.p.: 110–125° C./1.5–3 mmHg). C7F15C(O)N(CH3)C2H4OH was prepared at 50° C

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 3-1, four-necked, round-bottomed flask equipped with stirrer, thermometer, reflux condenser with bubble counter and inlet gas-tube, is charged with 745 g (1.74 mol) of methyl perfluorooctanoate and 1.5 l tetrahydrofurane. A stream of ammonia is passed from a pressure tank into the stirring solution. The ammonia feed rate is such that a negligible amount of gas is observed exiting the reactor as observed in the bubble counter. Temperature of the mixture increases to 40-50° C. Ammonium supply is continued until the temperature begins to decrease and an increasing volume of gas is observed exiting the reactor in the bubble counter . . . . After ending of ammonium supply, the mixture is left to stand for 12 hr. Solvent is removed under reduced pressure, yielding 712 g p perfluorooctanoic acid amide (99%), mp 136-137° C. A 3-1, four-necked, round-bottomed flask equipped with stirrer thermometer, reflux condenser with bubble counter and inlet gas-tube the mixture is left Solvent is removed under reduced pressure

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

Procedure: A 2-1, four-necked, round-bottomed flask equipped with stirrer, addition funnel, thermometer and reflux condenser, is charged with 828 g (2 mol) of dried perfluorooctanoic acid, 160 g (5 mol) of methanol. The mixture is stirred and 50 ml concentrated sulfuric acid is added dropwise. Then the mixture is heated to reflux for 4 hr. At the end of the reflux period the mixture is cooled to room temperature and poured into 2 l cold water. After separation of the phases, the lower organic phase is washed with water till pH neutral and dried over CaCl2. Distillation of the crude gives 762 g (89%) of methyl perfluorooctanoate, bp 160° C. A 2-1, four-necked, round-bottomed flask equipped with stirrer, addition funnel thermometer and reflux condenser Then the mixture is heated to reflux for 4 hr After separation of the phases the lower organic phase is washed with water till pH neutral and dried over CaCl2 Distillation of the crude