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Environmentally friendly hydrolysis process of Grignard reaction metal organic product

A metal-organic and Grignard reaction technology, applied in organic chemistry, hydrolysis preparation, magnesium sulfate, etc., can solve the problems of high cost, adverse effect of Grignard reaction yield, etc., and achieve the effect of zero waste water discharge

Active Publication Date: 2020-04-28
SHANGYU NHU BIOCHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the traditional process currently used not only requires complex and high-cost water removal procedures to ensure that the solvent reaches a sufficiently low moisture content, but also it is difficult to reduce the moisture in the solvent to below 200ppm, thereby affecting the Grignard reaction. Yield has a certain adverse effect

Method used

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  • Environmentally friendly hydrolysis process of Grignard reaction metal organic product
  • Environmentally friendly hydrolysis process of Grignard reaction metal organic product
  • Environmentally friendly hydrolysis process of Grignard reaction metal organic product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The metal organic product obtained by the Grignard reaction is called dichloromagnesium condensate for short, and the structure is as follows:

[0039]

[0040] Add 55.81g (0.315mol) pyridine hydrogen sulfate solid to the four-neck reactor, add 100ml ether solution and stir to cool down to about 10℃, then add the Grignard reaction dropwise to obtain the 0.75mol / L dichloromagnesium condensate 300ml of ether solution (containing 0.225mol of bischloromagnesium condensate), drip it in about 20 minutes, and then continue to stir for 90 minutes to stop the hydrolysis reaction. Add excess magnesium hydroxide to complete the reaction of excess pyridine hydrogen sulfate, and then filter to obtain 65 g of white solid and 394 ml of ether solution of the condensate product.

[0041] The solid is washed with 100ml of pure ether to remove a small amount of condensate. The washing liquid can be used as the solvent for the next pyridine bisulfate solid dissolution; the solids are mainly mag...

Embodiment 2

[0049] The metal-organic product obtained by the Grignard reaction is referred to as bis-bromomagnesium condensate, and the structure is as follows:

[0050]

[0051] Add 53.82g (0.21mol) of pyridine sulfate solid to the four-neck reactor, add 100ml of methyltetrahydrofuran solution and stir to cool down to about -20℃, then add the Grignard reaction dropwise to obtain a 1mol / L bisbromomagnesium condensate 200ml of methyl tetrahydrofuran solution (containing 0.2mol of bis-bromomagnesium condensate), drip in about 90 minutes, and then continue to stir for 20 minutes to stop the hydrolysis reaction. Adding excess magnesium hydroxide to complete the reaction of excess pyridine hydrogen bromide, and then filtering to obtain 65.5 g of white solid and 295 ml of methyl tetrahydrofuran solution as a condensate product.

[0052] The solid is washed with 100ml pure methyltetrahydrofuran to remove a small amount of condensate. The washing liquid can be used as the solvent for the next pyridine...

Embodiment 3

[0060] The metal organic product obtained by the Grignard reaction is trityl magnesium bromide, the structure is as follows:

[0061]

[0062] Add 52.2g (0.3mol) of 3-methylpyridine hydrobromide solid to the four-neck reactor, add 100ml of tetrahydrofuran solution and stir and raise the temperature to about 50℃, then add the Grignard reaction to obtain a concentration of 2.5mol / L. 100ml of tetrahydrofuran solution of benzylmagnesium bromide (containing 0.25mol of tritylmagnesium bromide), drip it in about 60min, and then continue to stir for 30min before stopping the hydrolysis reaction. Excessive magnesium hydroxide was added to completely react the excess 3-methylpyridine hydrobromide, and then filtered to obtain 51 g of white solid and 220 ml of triphenylmethane tetrahydrofuran solution.

[0063] The solid is washed with 100ml pure tetrahydrofuran to remove a small amount of triphenylmethane. The washing liquid can be used as the solvent for the next 3-methylpyridine hydrobromid...

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Abstract

The invention discloses an environmentally friendly hydrolysis process of a Grignard reaction metal organic product. The process specifically comprises the following steps: 1) adding a metered pyridine salt into a reactor, slowly adding an ether solution of a metal organic matter, and continuously reacting for a period of time until the reaction is complete after dropwise adding to obtain an alcohol hydrolysate and metal inorganic salt mixture; 2) filtering or centrifugally separating the obtained mixture to obtain an ether solution of an alcohol hydrolysate and a corresponding metal inorganicsalt solid, and washing the solid salt with an ether solvent; and 3) further treating the obtained solid salt and recycling, and distilling and rectifying the obtained ether solution of the alcohol hydrolysate to recover the ether solvent and pyridine organic matters in the ether solution. According to the process, pyridine acidic salt is used for replacing an acidic aqueous solution, so that thetreatment can be achieved without further introducing water into a reaction system, and the problems of wastewater discharge and solvent treatment are effectively solved.

Description

Technical field [0001] The invention relates to a post-treatment process of Grignard reaction, in particular to a green hydrolysis process of metal organic products of the Grignard reaction. Background technique [0002] Grignard reagent is an important metal organic compound with general formula RMgX, which has been widely used in organic synthesis. The Grignard reaction of Grignard reagents with ketones, aldehydes, esters and other substances can obtain corresponding alcohol metal organic substances, and various alcohol substances can be obtained through hydrolysis reaction. [0003] At present, the hydrolysis method for obtaining alcohol metal organic compounds by Grignard reaction is generally an acid aqueous solution hydrolysis process. Chinese patent 201611262269.2 discloses a method and device for continuous hydrolysis and neutralization of vitamin A intermediate double Grignard condensate, wherein the acid water is sulfuric acid, hydrochloric acid, phosphoric acid or ammon...

Claims

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Application Information

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IPC IPC(8): C07C29/09C07C33/14C01F5/40
CPCC01F5/40C07C29/09C07C2601/16C07C33/14
Inventor 郑兆祥陈梦桥何仕炜巫阳波单国红陈淳
Owner SHANGYU NHU BIOCHEM IND
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