Novel alkyl perfluoroalkene ethers

a technology of alkyl perfluoroalkene and ether, which is applied in the preparation of ethers, detergent compositions, organic chemistry, etc., can solve the problems that chlorine-containing compounds such as cfc compounds are considered to be detrimental to the earth's ozone layer

Inactive Publication Date: 2011-11-17
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0132]Benefits, other advantages, and solutions to problems have been described above with regard to specific embodiments. However, the benefits, advantages, solutions to problems, and any feature(s) that may cause any benefit, advantage, or solution to occur or become more pronounced are not to be construed as a critical, required, or essential feature of any or all the claims.
[0133]It is to be appreciated that certain features are, for clarity, described herein in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features that are, for brevity, described in the context of a single embodiment, may also be provided separately or in any subcombination. Further, reference to values stated in ranges include each and every value within that range.

Problems solved by technology

However, chlorine-containing compounds such as CFC compounds are considered to be detrimental to the Earth's ozone layer.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0100]Example 1 Demonstrates the Reaction of Methanol with perfluorohept-3-ene

[0101]A 250-mL, 3-neck RB flask was set up with overhead mechanical stirring, reflux condenser, heating mantle, and Claisen with thermocouple well and 50-mL addition funnel. 200 g (125 mL, ˜0.57 moles) of perfluorohept-3-ene and 37.7 g (0.67-moles) of powdered KOH were added to the flask. 18.3 g (0.57-moles) of methanol was slowly added with the addition funnel. There was a small exothermic reaction. After stirring for 30-minutes, a small amount of water (˜20-mL) was added through the condenser and there was a significant exothermic reaction that increased the temperature to between 60 and 70° C.

[0102]After stirring for 2-hours, the reaction mixture was flash distilled under vacuum (100-mmHg) into a dry ice cooled flask. The crude distillate was further separated from water in a 250-mL separatory funnel and dried over magnesium sulfate. Spinning band distillation resulted in a ˜60-mL forerun that boiled pr...

example 2

[0103]Example 2 Demonstrates the Reaction of Methanol with perfluorohept-3-ene

[0104]A second reaction of methanol with perfluorohept-3-ene was done in essentially the same manner as in Example 1. 200-g (125 mL, ˜0.57 moles) of perfluorohept-3-ene, 35.3-g (0.63-moles) of powdered KOH, 20-mL of water, and approximately ˜1-g of Aliquat® 336 were added to the flask. There was an immediate and substantial exothermic reaction with addition of methanol that increased the temperature to between 60 and 70° C. After addition, stirring and heating to between 60 and 70° C. were continued for 2 hours. After cooling to near ambient temperature, the reaction mixture was poured into a separatory funnel. There was a significant amount of precipitated salts remaining in the upper aqueous layer. The bottom layer (˜120-mL) was isolated and dried over magnesium sulfate.

example 3

[0105]Reaction of Methanol with perfluorohept-3-ene

[0106]A third reaction of methanol with perfluorohept-3-ene was done in essentially the same manner as in Example 1. 200-g (125 mL, ˜0.57 moles) of perfluorohept-3-ene, 78.3-g (0.63 moles) of 45% aqueous KOH, and 1-g of Aliquat® 336 were added to a 500-mL flask. There was an immediate and substantial exothermic reaction with addition of methanol that increased the temperature to between 60 and 70° C. After addition, stirring and heating to between 60 and 70° C. were continued for 2 hours. After cooling to near ambient temperature, the reaction mixture was poured into a separatory funnel. There were no precipitated salts remaining in the aqueous layer. The bottom layer (˜120-mL) was isolated and dried over magnesium sulfate.

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Abstract

Disclosed are compositions comprising a compound having the formula CF3(CF2)xCF═CFCF(OR)(CF2)yCF3, wherein R is CH3 or C2H5or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3. Also disclosed are unsaturated fluoroethers selected from the group consisting of CF3(CF2)xCF═CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)═CFCF2(CF2)yCF3, CF3CF═CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF═C(OR)CF2(CF2)yCF3, and mixtures thereof, wherein R can be either CH3, C2H5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3. Also disclosed herein are novel methods of making a composition comprising at least one of the compounds described.

Description

CROSS REFERENCE(S) TO RELATED APPLICATION(S) [0001]This application is a continuation of pending U.S. application Ser. No. 12 / 701,802, filed Feb. 8, 2010, which claims the benefit of priority of U.S. Provisional Applications 61 / 152,803, filed Feb. 16, 2009, and 61 / 287,275, filed Dec. 17, 2009.BACKGROUND INFORMATION [0002]1. Field of the Disclosure[0003]This invention relates to cleaning compositions comprising unsaturated fluorocarbon ethers, and methods of their manufacture. The invention further relates to use of said cleaning compositions in methods to clean, degrease, deflux, dewater, and deposit fluorolubricant. The invention further relates to novel unsaturated fluorocarbon ethers and their use as cleaning compositions and in the methods listed above.[0004]2. Description of the Related Art[0005]Chlorofluorocarbon (CFC) compounds have been used extensively in the area of semiconductor manufacture to clean surfaces such as magnetic disk media. However, chlorine-containing compou...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C41/06
CPCC11D7/5018C07C43/17
Inventor BARTELT, JOAN ELLENLOUSENBERG, ROBERT D.
Owner EI DU PONT DE NEMOURS & CO
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