Method for preparing fatty boric acid by utilizing isopropoxyboric acid pinacol ester

A technology of isopropoxyboric acid and propoxyboronic acid, which is applied in the field of preparing aliphatic boric acid from isopropoxyboronic acid pinacol ester, can solve the problems of restricting industrial production, potential safety hazards, harsh temperature conditions, etc. Flammable by-products, easy operation, avoiding the effect of cryogenic low temperature

Inactive Publication Date: 2013-07-03
DALIAN NETCHEM CHIRAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, spontaneous combustion of trimethylboron and triethylborane is easily produced during the reaction, which is easy to cause fire
So this method has the following disadvantages: harsh temperature conditions, low yield, and the corresponding pyrophoric gas of trimethylborane or triethylborane is easy to be produced in the process of acidification, which causes fire and has potential safety hazards. A fatal shortcoming limits industrial production

Method used

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  • Method for preparing fatty boric acid by utilizing isopropoxyboric acid pinacol ester

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Into a mechanically stirred 1L four-neck flask, under the protection of argon, add 74.4g of isopropoxy borate pinacol ester (0.40mol, 1eq), and put 200g of methylmagnesium chloride in tetrahydrofuran solution (2.0mmol / g, 0.40mol, 1eq), temperature controlled at -5 ~ 0 ℃ drop Grignard reagent, 3h after the drop, the temperature was raised to 20 ~ 25 ℃ for 2h reaction. After the reaction is completed, the temperature is controlled at 20-30°C, and 312g (1mol, 2.5eq) of 25% potassium bifluoride aqueous solution is added dropwise, and stirred at 20-30°C for 2-3 hours after dropping. Add 20 g of silica gel, and continue stirring at 20-30°C for 2-3 hours. After filtration, the filtrate was separated into layers, the aqueous layer was extracted with MTBE (200g×6), and the organic layers were combined. Concentrate the organic layer to obtain a crude product, add 40g ethyl acetate to redissolve, filter out insolubles, concentrate the filtrate, beat with 30g n-hexane, filter, an...

Embodiment 2

[0021] Into a mechanically stirred 1L four-neck flask, under argon protection, add 70.7g of isopropoxy borate pinacol ester (0.38mol, 1eq), and put 200g of ethylmagnesium chloride in tetrahydrofuran solution (1.9mmol / g, 0.38mol, 1eq), temperature controlled at -5 ~ 0 ℃ drop Grignard reagent, 2h after the drop, the temperature was raised to 20 ~ 25 ℃ for 2h reaction. After the reaction is completed, 296.4 g (0.95 mol, 2.5 eq) of 25% potassium bifluoride aqueous solution is added dropwise at a temperature of 20-30°C, and stirred at 20-30°C for 2-3 hours after dropping. Add 20 g of silica gel, and continue stirring at 20-30°C for 2-3 hours. After filtration, the filtrate was separated into layers, the aqueous layer was extracted with MTBE (180g×4), and the organic layers were combined. Concentrate the organic layer to obtain a crude product, add 35g of ethyl acetate to redissolve, filter out insolubles, concentrate the filtrate, beat with 28g of n-hexane, filter, and dry to obt...

Embodiment 3

[0023] In a mechanically stirred 1L four-neck flask, under argon protection, add 89.3g of isopropoxy borate pinacol ester (0.48mol, 1eq), and put 240g of isobutylmagnesium chloride in tetrahydrofuran solution (2.0mmol / g, 0.48mol, 1eq), temperature controlled at -5 ~ 0 ℃ drop Grignard reagent, 2h after the drop, the temperature was raised to 20 ~ 25 ℃ for 2h. After the reaction is completed, control the temperature at 20-30°C, add dropwise 374.4g (1.2mol, 2.5eq) of 25% potassium bifluoride aqueous solution, and stir at 20-30°C for 2-3 hours after dropping. Add 20 g of silica gel, and continue stirring at 20-30°C for 2-3 hours. After filtration, the filtrate was separated into layers, the aqueous layer was extracted with MTBE (200g×4), and the organic layers were combined. Concentrate the organic layer to obtain crude product, add 40g ethyl acetate to redissolve, filter out insoluble matter, concentrate the filtrate, 31g n-hexane beating, filter, dry to obtain 29.0g of white p...

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Abstract

The invention discloses a method for preparing fatty boric acid by utilizing isopropoxyboric acid pinacol ester. The method comprises the steps of adding a Grignard reagent dropwise in isopropoxyboric acid pinacol ester under the temperature condition of subzero 5 DEG C to 0 DEG C, stirring for 1-2 hours at the room temperature, adding a potassium bifluoride aqueous solution dropwise into a reaction liquid, stirring for 2-3 hours at the room temperature, adding silica gel, stirring for 2-3 hours at the room temperature, filtering, and extracting a water layer by an organic solvent A; adding an organic solvent B into an organic layer, filtering again, adding a nonpolar hydrocarbon solvent into the filtrate for pulping, and filtering to obtain organic boric acid. The method has the advantages of simplicity and convenience in operation, safety, environmental protection, lower cost and higher yield, is an appropriate method for preparing fatty boric acid, and is suitable for the industrial production; and further, the raw materials are easy to obtain.

Description

technical field [0001] The invention relates to the technical field of chemical product synthesis, in particular to a method for preparing fatty boric acid with isopropoxy boric acid pinacol ester. Background technique [0002] For small molecule aliphatic boric acids such as methyl boric acid, ethyl boric acid, etc., usually use Grignard reagent or lithium reagent and borate (usually trimethyl borate or isopropyl borate) at about -78 ° C Reaction under low temperature conditions, acidification and purification to obtain the product. However, trimethylboron and triethylborane are prone to spontaneous combustion during the reaction process, which can easily cause fire. So this method has the following disadvantages: harsh temperature conditions, low yield, and the corresponding pyrophoric gas of trimethylborane or triethylborane is easy to be produced in the process of acidification, which causes fire and has potential safety hazards. A fatal shortcoming has limited industr...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 刘启宾于双
Owner DALIAN NETCHEM CHIRAL TECH
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