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Preparation method of 9-boron bicyclo (3,3,1)-nonane (9-BBN)

A technology of 9-BBN and nonane, which is applied in the field of preparation of 9-boronbicyclo-nonane, can solve the problems that the preparation method is not easy to realize industrialized large-scale production, and achieve the advantages of shortening the product synthesis cycle, good application prospects, and facilitating industrialization Effect

Inactive Publication Date: 2014-01-22
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yields of the preparation methods described in the literature are all lower than 90%, and the preparation methods are not easy to realize industrialized large-scale production

Method used

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  • Preparation method of 9-boron bicyclo (3,3,1)-nonane (9-BBN)
  • Preparation method of 9-boron bicyclo (3,3,1)-nonane (9-BBN)
  • Preparation method of 9-boron bicyclo (3,3,1)-nonane (9-BBN)

Examples

Experimental program
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Effect test

Embodiment example 1

[0031] Under the protection of nitrogen, add 10g of crushed 4A molecular sieve, 100ml of solvent tetrahydrofuran, 12.3ml of 1,5-cyclooctadiene and 0.23g of zirconium tetrachloride in a 250ml reaction flask equipped with a reflux device, and magnetically stir at room temperature for 1 hour to make The reactants are evenly mixed, and the reaction solvent and trace water in the raw materials are removed. Cool down to about 0℃, add 10ml of 10M / L borane dimethyl sulfide complex dropwise at a rate of 1 drop per second. After the dropwise addition is complete, heat and reflux for 4 hours, take samples, and detect the isomer 9-boron by GC Bicyclo(4,2,1)-nonane is completely converted into 9-boronbicyclo(3,3,1)-nonane, stop heating, cool the obtained product to 0℃, continue stirring, keep it for 3 hours, It was filtered under the protection of nitrogen to obtain 11.9 g of crystalline solid with a yield of 98.0%.

Embodiment example 2

[0033] Under the protection of nitrogen, add 10g of crushed 4A molecular sieve, 100ml of solvent tetrahydrofuran, 12.3ml of 1,5-cyclooctadiene and 0.23g of zirconium tetrachloride in a 500ml reaction flask equipped with a reflux device, and magnetically stir at room temperature for 1 hour to make The reactants are evenly mixed, and the reaction solvent and trace water in the raw materials are removed. Cool down to about 0°C, add 100ml of 1M / L borane dimethyl sulfide complex at a rate of 5 drops per second. After the addition is complete, heat and reflux for 4 hours, take samples, and detect the isomer 9-boron by GC Bicyclo(4,2,1)-nonane is completely converted into 9-boronbicyclo(3,3,1)-nonane, stop heating, cool the obtained product to 0℃, continue stirring, keep it for 3 hours, It was filtered under the protection of nitrogen to obtain 11.6 g of crystalline solid with a yield of 95.2%.

Embodiment example 3

[0035] Under the protection of nitrogen, add 10g of crushed 4A molecular sieve, 100ml of 1,4-dioxane solvent, 12.3ml of 1,5-cyclooctadiene and 1.1g of zirconium tetrachloride into a 500ml reaction flask equipped with a reflux device in sequence, at room temperature Magnetic stirring is applied for 1 hour to make the reactants mix uniformly and remove trace water in the reaction solvent and raw materials. Cool down to about 0℃, add 10ml of 10M / L borane dimethyl sulfide complex dropwise at a rate of 1 drop per second. After the dropwise addition is complete, heat and reflux for 4 hours, take samples, and detect the isomer 9-boron by GC Bicyclo(4,2,1)-nonane is completely converted into 9-boronbicyclo(3,3,1)-nonane, stop heating, cool the obtained product to 0℃, continue stirring, keep it for 3 hours, It was filtered under the protection of nitrogen to obtain 11.8 g of crystalline solid with a yield of 96.7%.

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Abstract

The invention provides a new synthesis method of 9-boron bicyclo (3,3,1)-nonane (9-BBN). 1,5-cyclooctadiene and borane are taken as raw materials, a reaction is carried out in a tetrahydrofuran solvent, and the 9-boron bicyclo (3,3,1)-nonane (9-BBN) is synthesized while yield is as high as 98%. The new synthesis method comprises the following steps of adding a smashed 4A molecular sieve, tetrahydrofuran, 1,5-cyclooctadiene and zirconium tetrachloride into a reaction flask, stirring for 1 hour, dropwise adding a dimethyl sulfide complex of borane at the temperature about 0 DEG C, carrying out a reflux reaction for 4 hours after dropwise addition is completed to obtain a product, cooling the obtained product to 0 DEG C and preserving heat for 3 hours, and filtering to obtain a 9-boron bicyclo (3,3,1)-nonane (9-BBN) solid product. The new synthesis method of the 9-boron bicyclo (3,3,1)-nonane (9-BBN) has the advantages of high yield, low cost, high product purity, easy operation, is beneficial to industrialization and has a good application prospect.

Description

【Technical Field】 [0001] The invention belongs to the field of fine chemicals, and relates to a method for preparing 9-boronbicyclo(3,3,1)-nonane. 【Background technique】 [0002] 9-borabicyclo(3,3,1)-nonane (9-borabicyclo[3.3.1]nonane) is abbreviated as 9-BBN, CAS (chemical substance registration number): 280-64-8, molecular formula: C 8 H 15 B, molecular weight: 122.02. The product is a crystalline solid with a melting point of 140-142°C and a boiling point of 195°C (1599.9Pa). It often exists in the form of dimerization. The dimer is also crystalline, with a melting point of 150-152°C. Compared with other borane reagents, 9-BBN has good thermal stability and stability. It does not change when heated at 200°C under nitrogen flow. It is also stable to oxygen in the air. It is stored in a bottle with air. Two months does not reduce the activity of boron atoms, but it is sensitive to water. Commercial 9-BBN is usually sold as a THF solution. [0003] The borohydride reaction is th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
Inventor 徐凤波张春来董建兰
Owner NANKAI UNIV
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