Cyclic hydrofluoroether compounds and processes for their preparation and use
A technology for compounds and hydrofluoroethers, applied in the field of preparing partially fluorinated ether compounds, can solve problems such as incompatibility, and achieve cost-saving effects
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[0060] Preparation of hydrofluoroether compounds
[0061] The hydrofluoroether compounds (HFE) of the present invention can be prepared by alkylation of fluorine-containing alkoxides via fluorine-containing ketones (more specifically, having: (a) branched fluoroalkyl groups) A carbonyl or perfluoroalkylcarbonyl end group, and (b) an intervening linear or branched perfluoroalkylene segment of the fluorinated diketone, the branched fluoroalkylcarbonyl or perfluoroalkylcarbonyl The end group optionally comprises at least one catenary heteroatom selected from a divalent ether oxygen atom and a trivalent nitrogen atom) with anhydrous alkali metal fluoride (such as potassium fluoride or cesium fluoride) or anhydrous silver fluoride ( It is preferably prepared by reacting in an anhydrous polar aprotic solvent). Preferably, the perfluoroalkylene segment has two or three catenary atoms. See, for example, the preparations described in French Patent Publication No. 2,287,432 and Germ...
example
[0142] Objects and advantages of this invention are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit this invention. These examples are illustrative only, and are not intended to limit the scope of the appended claims.
[0143] All parts, percentages, ratios, etc. in the examples, as well as in the remainder of the specification, are by weight unless otherwise indicated. Solvents and other reagents used were purchased from Aldrich Chemical Company, St. Louis, Missouri unless otherwise indicated.
[0144] In the following examples, a diastereomeric mixture is obtained due to the presence of two (or more) optical centers in the molecule. These diastereomers have boiling points very close to each other and therefore diastereomers cannot be separated by distillation. In some cases, however, such diastereomers are readily separ...
example 1
[0177] Example 1: Preparation of 2-ethoxy-3,3,4,4-tetrafluoro-2,5-bis(1,2,2,2-tetrafluoro-1-trifluoromethane Ethyl)tetrahydrofuran
[0178]
[0179] A 500 mL round bottom flask equipped with an overhead stirrer, heating mantle, thermocouple temperature controller, nitrogen bubbler, and condenser was charged with 32.3 g (0.56 mol) of spray-dried potassium fluoride, 104 g of anhydrous Glyme, 12.7 g (0.014 mol) Adogen TM 464 phase transfer catalyst, 89.1 grams (0.58 moles) of diethyl sulfate and 220 grams (0.445 moles) of 98.3% purity dodecafluoro-2,7-trifluoromethyl-3,6-octanedione. The flask was maintained at 54°C for 16 hours and then allowed to cool down. After cooling to 25°C, 50 grams (0.40 moles) of aqueous potassium hydroxide ((45% in water) and 75 grams of water were added to the flask. The resulting solution was heated to 80°C and maintained for 4 hours, and the resulting solution was separated by steam distillation. The obtained crude product was washed twice...
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