1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane

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

Procedure: The present invention also relates to the discovery of azeotropic or azeotrope-like compositions of effective amounts of C4F9 OCH3 and methanol, ethanol, isopropanol, n-heptane, t-DCE, c-DCE, or acetone; C4F9OCH3, n-heptane and methanol, ethanol or isopropanol; C4F9OCH3, t-DCE and methanol, ethanol or isopropanol; C4F9OCH3, c-DCE and methanol or ethanol; C4F9OCH3, acetone and methanol, ethanol, or isopropanol; C4F9OCH3, HFC-43-10mee and methanol to form an azeotropic or azeotrope-like composition.

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

Procedure: 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. A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser stirring after the addition the lower fluorochemical phase of the mixture was separated from the upper phase washed once with saturated aqueous sodium chloride solution Since the fluorochemical phase still contained about 12% diglyme, water was added to it the resulting product was azeotropically distilled to yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which

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

Procedure: GLC at the conclusion of the addition showed the following C4F9OCH3(5%), C4F9OCH2Cl (65%) and C4F9OCHCl2 HCl2 (29%) and C4F9OCCl3 (0.2%). The reaction solution was washed first with dilute aqueous potassium hydroxide, and then with water, and distilled using a 40-plate perforated plate column to yield C4F9OCH2Cl, b.p.=87° C. and C4F9OCHCl2, b.p.=96° C. in purifies of about 99%. GLC at the conclusion of the addition The reaction solution was washed first with dilute aqueous potassium hydroxide with water, and distilled

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

Procedure: This compound is available from 3M Company, St. Paul, Minn. as NOVEC™ HFE-7100 engineering fluid, which is an isomeric mixture of approximately 60% (CF3)2CFCF2OCH3 and approximately 40% CF3CF2CF2CF2OCH3.

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

Procedure: This compound is available from 3M Company, St. Paul, Minn. as NOVEC™ HFE-7100 engineering fluid, which is an isomeric mixture of approximately 60% (CF3)2CFCF2OCH3 and approximately 40% CF3CF2CF2CF2OCH3.

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

Procedure: This compound is available from 3M Company, St. Paul, Minn. as NOVEC™ HFE-7100 engineering fluid, which is an isomeric mixture of approximately 60% (CF3)2CFCF2OCH3 and approximately 40% CF3CF2CF2CF2OCH3.

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

Procedure: 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. A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser stirring after the addition the lower fluorochemical phase of the mixture was separated from the upper phase washed once with saturated aqueous sodium chloride solution Since the fluorochemical phase still contained about 12% diglyme, water was added to it the resulting product was azeotropically distilled to yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which

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

Procedure: 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. A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser stirring after the addition the lower fluorochemical phase of the mixture was separated from the upper phase washed once with saturated aqueous sodium chloride solution Since the fluorochemical phase still contained about 12% diglyme, water was added to it the resulting product was azeotropically distilled to yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which

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

Procedure: 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. A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser stirring after the addition the lower fluorochemical phase of the mixture was separated from the upper phase washed once with saturated aqueous sodium chloride solution Since the fluorochemical phase still contained about 12% diglyme, water was added to it the resulting product was azeotropically distilled to yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which

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

Procedure: 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. A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser stirring after the addition the lower fluorochemical phase of the mixture was separated from the upper phase washed once with saturated aqueous sodium chloride solution Since the fluorochemical phase still contained about 12% diglyme, water was added to it the resulting product was azeotropically distilled to yield 32.8 g of c-C6F11OCH3 (b.p.=100° C.), which

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

Procedure: 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), 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. A 500 ml, 3-necked round bottom flask equipped with an overhead stirrer, an addition funnel, and a condenser stirring after the addition the lower fluorochemical phase of the mixture was separated from the upper phase washed once with saturated aqueous sodium chloride solution Since the fluorochemical phase still contained about 12% diglyme, water was added to it the resulting product was azeotropically distilled to yield 32.8 g of c

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

Procedure: The present invention also relates to the discovery of azeotropic or azeotrope-like compositions of effective amounts of C4F9 OCH3 and methanol, ethanol, isopropanol, n-heptane, t-DCE, c-DCE, or acetone; C4F9OCH3, n-heptane and methanol, ethanol or isopropanol; C4F9OCH3, t-DCE and methanol, ethanol or isopropanol; C4F9OCH3, c-DCE and methanol or ethanol; C4F9OCH3, acetone and methanol, ethanol, or isopropanol; C4F9OCH3, HFC-43-10mee and methanol to form an azeotropic or azeotrope-like composition.