Dimethyl Sulfate → Methyl perfluorobutyl ether

A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser was charged with anhydrous cesium fluoride (27.4 g, 0.18 mole), anhydrous diethylene glycol dimethyl ether (258 g, hereinafter diglyme), and dimethyl sulfate (22.7 g, 0.18 mole). Perfluorocyclohexanone (50 g, 0.18 mole) was then added dropwise to the resulting stirred mixture, and stirring was continued for 18 hours after the addition. Water (approximately 200 ml) was added to the resulting mixture, and the lower fluorochemical phase of the mixture was separated from the upper phase and washed once with saturated aqueous sodium chloride solution. Since the fluorochemical phase still contained about 12% diglyme, water was added to it, and the resulting product was azeotropically distilled to yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which was free of diglyme. The product identity was confirmed by IR, GCMS, and 1H and 19F NMR.

1. customA 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser
2. stirringstirring
3. additionafter the addition
4. customthe lower fluorochemical phase of the mixture was separated from the upper phase
5. washwashed once with saturated aqueous sodium chloride solution
6. additionSince the fluorochemical phase still contained about 12% diglyme, water was added to it
7. distillationthe resulting product was azeotropically distilled
8. customto yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which

ORD record

ord-ea8459e4dffb4d92b86b315d0dd58102

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06380149B2