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Method for sulphonylation of hydroxylated organic compound

An organic compound, hydroxylation technology, used in the trifluoromethanesulfonylation of 2, hydroxylated organic compounds, those containing perfluorinated aliphatic chains, perfluorinated aliphatic alcohols, and can solve high pollution, etc. question

Inactive Publication Date: 2013-10-30
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The disadvantage of this method is that it results in highly polluting emissions due to the presence of large amounts of ammonium salts

Method used

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  • Method for sulphonylation of hydroxylated organic compound
  • Method for sulphonylation of hydroxylated organic compound
  • Method for sulphonylation of hydroxylated organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 6

[0100] Example 6 concerns the sulfonylation of ethanol in the presence of a heterogeneous base.

[0101] Examples 7-10 are comparative tests in which the base is a nitrogen-containing organic base.

Embodiment 11

[0102] Example 11 concerns the sulfonylation of ethanol with trifluoromethanesulfonyl chloride in the presence of a heterogeneous base.

[0103] In the examples, the following abbreviations represent:

[0104] -TFE: trifluoroethanol,

[0105] -TFSBr: trifluoromethanesulfonyl bromide (bromure de triflyle),

[0106] -TFSC1: trifluoromethanesulfonyl chloride (chlorure de triflyle),

[0107] -ACN: Acetonitrile

[0108] -MCB: monochlorobenzene

[0109] -ODCB: o-dichlorobenzene.

[0110] Trichloromethanesulfonyl bromide or trichloromethanesulfonyl chloride (CF 3 SO 2 Br or CF 3 SO 2 The conversion (TT) of Cl) corresponds to the ratio of the moles of trichloromethanesulfonyl bromide or trichloromethanesulfonyl chloride converted to the moles of trichloromethanesulfonyl bromide or trichloromethanesulfonyl chloride introduced.

[0111] TfOTFE yield (RR TfOTFE ) corresponds to the ratio of the number of moles of TfOTFE formed to the number of moles of trichloromethanesulfonyl ...

Embodiment 1-5

[0115] The following were introduced into a 150 ml glass reactor under nitrogen:

[0116] -K 2 CO 3 : 7g (50.14mmol)

[0117] -TFE: 3.2g (32mmol)

[0118] - Solvent: 7 g.

[0119] The resulting heterogeneous medium is brought under stirring to the temperature T mentioned in the following table (I) and then added with TFE (3.2 g, 32 mmol) or TFSBr (7 g, 32 mmol) diluted with solvent (7 g).

[0120]After the addition, the reaction medium is kept at the temperature T' mentioned in table (I) for the time t', and is then passed through 19 F NMR quantitatively measures the reactants and the products obtained.

[0121] The results obtained are reported in Table (I).

[0122] Table (I)

[0123]

[0124] ＊ = Calculated relative to TFSBr

[0125] Example 6

[0126] The following were introduced into a 150 ml glass reactor under nitrogen:

[0127] -K 2 CO 3 : 7g (50.14mmol)

[0128] -EtOH: 3.2g (32mmol)

[0129] -ODCB: 25g.

[0130] The resulting heterogeneous medium ...

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Abstract

The subject of the present invention is a method for the sulphonylation of a hydroxylated organic compound. The invention relates more particularly to a method for the trifluoromethanesulphonylation of a hydroxylated organic compound. The invention is especially intended for perfluorinated aliphatic hydroxylated compounds. The method of the invention for the sulphonylation of a hydroxylated organic compound is characterized in that it comprises reacting said compound with a sulphonylation agent in an organic medium and in the presence of a heterogeneous inorganic base.

Description

technical field [0001] This invention relates to a process for the sulfonylation of hydroxylated organic compounds. [0002] The present invention more particularly relates to a process for the triflation of hydroxylated organic compounds. [0003] The present invention is especially directed to hydroxylated compounds of the aliphatic type, and especially those comprising perfluorinated aliphatic chains. [0004] The invention preferably applies to perfluorinated aliphatic alcohols, especially 2,2,2-trifluoroethanol. Background technique [0005] According to FR-A-1470669 known, by 2,2,2-trifluoroethanol and trifluoromethanesulfonyl chloride (CF 3 SO 2 Cl) in the presence of a base such as triethylamine and in an organic solvent (which is dichloromethane) to prepare trifluoroethyl trifluoromethanesulfonate (CF 3 SO 3 CH 2 CF 3 ). [0006] A disadvantage of this method is that it results in highly polluting emissions due to the presence of large amounts of ammonium sa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/28C07C309/65
CPCC07C303/28C07C309/65
Inventor F·梅茨
Owner RHODIA OPERATIONS SAS