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Process for preparing a sulphonic acid anhydride

A technology of sulfonic acid anhydride and sulfonic acid, applied in the preparation of acid anhydride, the preparation of symmetrical or mixed anhydride, the preparation of "anhydridetriflique", and the field of trifluoromethanesulfonic anhydride, which can solve the problems of difficulty and cost of phosphoric acid

Active Publication Date: 2009-08-26
RHODIA OPERATIONS SAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The dehydration reaction between two molecules of sulfonic acid works well, but the amount of phosphoric acid and the difficulty in choosing a suitable solvent make this operation particularly difficult and costly, especially with regard to stirring, which has to be carried out in a particularly aggressive medium

Method used

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  • Process for preparing a sulphonic acid anhydride
  • Process for preparing a sulphonic acid anhydride
  • Process for preparing a sulphonic acid anhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0123] Preparation of trifluoromethanesulfonic anhydride

[0124] A 250 ml reactor was used which was heated with a double jacket and equipped with a central mechanical stirrer, dropping funnel and elbow which was cooled to 15°C via a) a dry ice trap b) a wash bottle containing sodium hydroxide solution and Feed to collector in atmosphere.

[0125] 73 g of RO constituting the "pied" of the reaction mixture were charged; trichloromethylbenzoyl chloride used was equilibrated in a molar ratio of 20 / 80 with its pseudochloride tautomeric form.

[0126] The primer was heated to 120°C.

[0127] Using a dropping funnel, 157 g of trifluoromethanesulfonic acid was gradually added over 3 hours, keeping the temperature of the reaction mass at 115°C to 135°C.

[0128] Evolution of HCl was observed from the beginning of the addition and crude TAA condensed after about 15 minutes.

[0129] The HCl stream was converted to organic vapor by condensation in a dry ice trap.

[0130] After the...

Embodiment 2 and 3

[0138] Comparative test A-O

[0139] A series of qualitative experiments were performed to demonstrate the effect of the type of reagent used.

[0140] Before detailing the examples and experiments, a description of the apparatus used and the protocols followed will be provided.

[0141] device used

[0142] The device used is Temperature gradient oven (Glass Oven B 580).

[0143] It is in the form of a tubular glass furnace into which a single-necked reaction flask is introduced, which is connected to two receiving flasks.

[0144] The above-mentioned whole is linked together and can be rotated by a motor.

[0145] The light products of the reaction were trapped at the outlet by dry ice into two receiving flasks.

[0146] Visually monitor for possible gas emissions with a bubble meter.

[0147] operating procedures

[0148] Reagents were weighed (max weight 10 g) in reaction vials in a fume hood.

[0149] The molar ratio between sulfonic acid and reagent is sho...

Embodiment 2

[0175] In this example, the sulfonic acid used is trifluoromethanesulfonic acid, and the reagent used is a compound having at least one gem-dichloro carbon atom involved in the tautomerization of the pseudoacyl chloride.

[0176] The results are shown in Table (IV).

[0177] Table (IV)

[0178] Test label

[0179] The recovered distillate was analyzed by fluorine NMR spectroscopy. It consists essentially of trifluoromethanesulfonic anhydride.

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Abstract

The present invention relates to a process for preparing a sulphonic acid anhydride, and more particularly to the preparation of triflic anhydride. The process for preparing a sulphonic acid anhydride according to the invention is characterized in that it comprises reacting a sulphonic acid or a mixture of two sulphonic acids with a reactant exhibiting pseudo acid halide tautomerism with at least one carbon atom which is involved in the tautomerism bearing two halogen atoms.

Description

technical field [0001] The present invention relates to a process for the preparation of sulfonic anhydrides. [0002] It involves the preparation of symmetrical or mixed anhydrides. [0003] More specifically, it relates to the preparation of anhydrides derived from superacide sulfoniques. [0004] More specifically, the present invention relates to the preparation of trifluoromethanesulfonic anhydride, also known as "anhydridetriflique". Background technique [0005] Sulfonic acid superacids, ie those with a Hammett constant of at least 12, advantageously at least 13, are increasingly being used as synthetic intermediates, especially for the formation of particularly reactive leaving groups. [0006] These sulfonic superacids are generally sulfonic acids in which the sulfur bears a fluorinated functionality, usually with a difluoromethylene unit linking the sulfur of the sulfonic acid functionality to the rest of the acid molecule. group. [0007] To graft these sulfon...

Claims

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Application Information

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IPC IPC(8): C07C303/00C07C309/06
CPCC07C303/00C07C309/00
Inventor B·贝森
Owner RHODIA OPERATIONS SAS
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