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Methods of preparing fluorinated carboxylic acids and their salts

A technology for fluorinating carboxylic acids and carboxylic acids, which is applied in chemical instruments and methods, preparation of carboxylate salts, preparation of organic compounds, etc., and can solve problems such as low yield and expensive reagents

Inactive Publication Date: 2012-07-11
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these reactions can be performed on an industrial scale with good yields, these methods are not advisable to perform on a large scale due to, among other things, concerns about heavy metal handling, low yields, high temperatures and the use of expensive reagents

Method used

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  • Methods of preparing fluorinated carboxylic acids and their salts
  • Methods of preparing fluorinated carboxylic acids and their salts
  • Methods of preparing fluorinated carboxylic acids and their salts

Examples

Experimental program
Comparison scheme
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Embodiment

[0122] The following is a summary of specific embodiments of the invention:

[0123] 1. A method for the preparation of highly fluorinated carboxylic acids and salts thereof, which comprises making a highly fluorinated alcohol of general formula (A):

[0124] A-CH 2 -OH

[0125] contacting at least one first oxidizing agent and at least one second oxidizing agent to generate a highly fluorinated carboxylic acid or salt thereof of general formula (A1):

[0126] A-COO - m +

[0127] where M + Represents a cation and wherein A in formulas (A) and (A1) is the same and represents a residue:

[0128] Rf-[O] p -CX"Y" -[O] m -CX'Y'-[O] n -CXY-

[0129] wherein Rf represents a fluorinated alkyl residue which may or may not contain one or more catenary oxygen atoms, p, m and n are 1 or 0 independently of each other, X, X', X", Y, Y' and Y" independently of each other is H, F, CF 3 or C 2 f 5 , with the proviso that X, X', X", Y, Y', and Y" are not all H, and wherein said a...

example

[0194] The following examples further describe the preparation of compositions of the present invention. The particular materials and amounts thereof, as well as other conditions and details, recited in these examples should not be construed to unduly limit this invention. All materials are commercially available, for example, from Sigma-Aldrich Chemical Company (Milwaukee, Wisconsin) or are known to those skilled in the art unless otherwise stated or apparent.

[0195] These abbreviations are used in the following examples: eq = equivalent, g = gram, M = mole, min = minute, mol = mole; mmol = millimole, hr = hour, mL = milliliter, mmHg = millimeter of mercury, L = liter , wt = weight, FTIR = Fourier transform infrared spectroscopy, NMR = nuclear magnetic resonance and GC-MS = gas chromatography-mass spectrometry.

[0196] The resulting samples were analyzed by proton or fluorine NMR as follows unless otherwise stated. Peaks in NMR were integrated. The peak areas believed t...

example 1

[0218] To a mixture of 92.8 g of 5.25 wt % sodium hypochlorite solution (65.4 mmol, 2.5 eq) and 2.09 g (52.3 mmol, 2 eq) of sodium hydroxide was added 10.0 g (26.2 mmol, 1 eq) of 2,2,3-trifluoro-3 -(1,1,2,2,3,3-hexafluoro-3-trifluoromethoxypropoxy)propan-1-ol, 0.0573g (0.366mmol, 0.014eq) TEMPO and 0.716g (1.30 mmol, 0.05eq) a mixture of tetra-n-octylammonium bromide. The mixture was stirred and heated to 40°C for about 2 hours. In an attempt to extract the fluorinated carboxylic acids while retaining tetra-n-octylammonium bromide, the following procedure was performed. The reaction mixture was cooled and washed with a 50:50 methyl tert-butyl ether / hexane mixture. The organic phase was acidified with 8.0 mL of 12M hydrochloric acid solution. The mixture was extracted with methyl tert-butyl ether, the organic phase was washed with water, filtered and concentrated to give 8.5 g of crude product.

[0219] pass 1 H NMR and 19 As determined by F NMR, the crude product contain...

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Abstract

A method for preparing fluorinated carboxylic acids and theirs salts is described comprising subjecting a fluorinated alcohol of the general formula (A): A-CH2-OH to at least one first and at least one second oxidizing agent to produce a highly fluorinated carboxylic acid or their salts of the general formula (B): A-COO M+, wherein M+ represents a cation and wherein A in formulas (A) and (B) is the same and A represents the residue: Rf-[0]p-CX"Y"-[0]m-CX'Y'-[0]n-CXY- wherein Rf represents a fluorinated alkyl residue which may or may not contain one or more catenary oxygen atoms, p, m and n are independently from each other either 1 or O, X, X', X", Y, Y' and Y" are independently from each other H, F, CF3, or C2F5 with the proviso that not all of X, X', X", Y, Y' and Y" are H; or A represents the residue: R-CFX- wherein X and R are independently selected from a hydrogen, a halogen, or an alkyl, alkenyl, cycloalkyl, or aryl residue, which may or may not contain one or more fluorine atoms and which may or may not contain one or more catenary oxygen atoms; wherein said at least one first oxidizing agent is a compound that can be converted, by action of the second oxidizing agent, into a reactive species capable of oxidizing the fluorinated alcohol.

Description

[0001] priority document [0002] This application claims priority to US Provisional Patent Application No. 61 / 254229 and UK Application No. 0918616.4, both filed October 23, 2009, both of which are incorporated herein in their entirety. technical field [0003] The present invention relates to a method for preparing fluorinated carboxylic acids and salts thereof. Background technique [0004] Fluorinated carboxylic acids have been used as synthetic intermediates in the preparation of industrial and specialty chemicals and as emulsifiers or dispersants in polymer preparation such as polymerization of fluorinated monomers. In the past, low molecular weight perfluorocarboxylic acids of the general formula CF3-(CF2)n-COO-M+, where M+ represents a cation and n represents an integer between 4 and 8, have been used in the polymerization of fluorinated monomers . However, alternative fluorinated emulsifiers have received attention for various reasons. Fluorinated polyether carb...

Claims

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Application Information

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IPC IPC(8): C07C51/27C07C53/18C07C53/21C07C59/135C07C59/125C25B3/23
CPCC07C51/27C07C53/21C07C59/135
Inventor 克劳斯·辛策丹尼斯·E·沃格尔米格尔·A·格拉约兰塔·伊格纳托夫斯卡格尔德-沃尔克·罗切塔勒奥列格·夏伊绍科夫金·M·沃格尔蒂尔曼·C·兹普利斯
Owner 3M INNOVATIVE PROPERTIES CO
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