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Method for preparing electronic 2,2'-binaphthol

An electronic-grade, binaphthol technology, applied in the field of compound preparation, can solve problems such as product yield, quality and cost are difficult to meet, product purity is difficult to reach electronic level, unfavorable to occupational health and labor protection, etc., to achieve production The effect of good environment, easy operation and low equipment requirements

Inactive Publication Date: 2018-05-29
YWK CHEM TAICANG
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Problems solved by technology

[0003] The synthetic method of 2,2'-binaphthol mainly contains two kinds of liquid phase method and solid phase method, and wherein solid phase method is to put 2-naphthol and iron trichloride hexahydrate into ball mill and grind reaction, and this method is to The control requirements of reaction equipment and reaction temperature are relatively strict, so far it cannot be industrialized
[0004] At present, the industrial production of 2,2'-binaphthol mainly adopts the liquid phase method, "Synthesis and Resolution Organic Synthesis Experiment of Improved 1,1'-Binaphthol" ("University Chemistry", No. 28 Volume No. 5, October, 2013), there are related records, but there are following disadvantages in this method: (a) need to pulverize and sieve the raw material 2-naphthol to about 200 mesh to promote the reaction thoroughly, while conventional The 2-naphthol industrial product is in the form of flakes or blocks, and 2-naphthol is highly volatile, and its solid crushing process has caused pollution and deterioration of the production environment, which is not conducive to occupational health and labor protection; (a) the product’s The purity is difficult to meet the requirements of the electronic level; (3) the amount of catalyst ferric chloride is large, the catalytic performance is not high, and there are many by-products, which is especially unfavorable for the recovery and reuse of waste water
[0005] In fact, the preparation of 2,2'-binaphthol with the existing technology, its product yield, quality and cost are all difficult to meet the requirements of foreign customers and high-demand electronic chemicals. Therefore, it is necessary to develop The reaction system is simple, the operation is convenient, the cost is low, and the new preparation method of green environmental protection

Method used

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  • Method for preparing electronic 2,2'-binaphthol

Examples

Experimental program
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Effect test

Embodiment 1

[0038] A preparation method of electronic grade 2,2'-binaphthol, the specific steps are as follows:

[0039] In a 250mL four-necked flask, equipped with a thermometer, an electric stirrer, and a reflux condenser, dissolve 7.2g of 2-naphthol and 0.72g of a phase transfer catalyst (TBAB) in 9.5g of methanol, and stir Heat up to 70°C to dissolve, then add 130.0g of 17.6% ferric chloride aqueous solution and 0.96g of 30% hydrogen peroxide in batches under heat preservation conditions, and heat at 70°C for 1 hour.

[0040] The reaction progress of the mixed solution is monitored, and when the high-performance liquid chromatography monitors that the 2-naphthol content is less than or equal to 3.0%, the reaction is stopped. Then 8.0 g of 1,2-dichloroethane was added, and the reaction was continued to stir at 60°C for 30 minutes, cooled to crystallize, filtered, washed, and dried to obtain 6.58 g of 2,2'-binaphthol with a yield of 92.0%.

[0041] Product YI value is measured as 3.5 b...

Embodiment 2～4

[0043] Examples 2-4 all basically adopt the following preparation method of electronic grade 2,2'-binaphthol, the specific steps are as follows, the difference is that the phase transfer catalysts added in Examples 2-4 are different, and the dosage is also different. As shown in Table 1:

[0044] In a 250mL four-neck flask equipped with a thermometer, an electric stirrer, and a reflux condenser, dissolve 7.2g of 2-naphthol and a phase transfer catalyst in 9.5g of methanol, heat up to 70°C under stirring to dissolve, and then Add 76.70g mass concentration in batches of 17.6% ferric chloride aqueous solution and 30% hydrogen peroxide (the amount of hydrogen peroxide in Examples 2-4 is different, see Table 1 respectively;) 70°C insulation reaction for 1 hour.

[0045] The reaction progress of the mixed solution is monitored, and when the high-performance liquid chromatography monitors that the 2-naphthol content is less than or equal to 3.0%, the reaction is stopped. Then add 8....

Embodiment 5

[0049] A preparation method of electronic grade 2,2'-binaphthol, the specific steps are as follows:

[0050] In a 250mL four-necked bottle, equipped with a thermometer, an electric stirrer, and a reflux condenser, add 9.5g of methanol, 14.4g of 2-naphthol, and 0.72g of sodium dodecylbenzenesulfonate, and heat up to 70°C under stirring to dissolve. Then, 114.9 g of ferric chloride aqueous solution with a mass concentration of 23.5% and 2.83 g of hydrogen peroxide with a mass concentration of 30% were added in batches under heat preservation conditions, and the reaction was carried out at 75° C. for 1 hour.

[0051] The reaction progress of the mixed solution is monitored, and when the high-performance liquid chromatography monitors that the 2-naphthol content is less than or equal to 3.0%, the reaction is stopped. Then add 12.0 g of toluene, continue to stir and react at 70°C for 30 min, cool down to crystallize, filter, wash, and dry to obtain 12.87 g of 2,2'-binaphthol with a...

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Abstract

The invention discloses a method for preparing electronic 2,2'-binaphthol. The method comprises the following steps: under the action of a phase transfer catalyst and / or a surfactant, enabling 2-naphthol to react with a ferric trichloride solution and hydrogen peroxide, and finally performing reaction treatment with a water insoluble organic solvent, thereby obtaining an electron-grade product, namely 2,2'-binaphthol. Compared with the prior art, the method has the advantages that (1) the method has the advantages of a small amount of wastes of a solid-phase method and reaction balance, easiness in operation and low equipment requirements of a liquid-phase method; (2) the reaction efficiency is high, and a small amount of ferric chloride is used; (3) a product yield is high, and the highest product yield is up to 95%; (4) the product purity is improved, and electron-grade high requirements of electronic chemicals on raw materials are met; (5) a good production environment can be made,the working intensity is low, a small amount of wastewater is generated, and wastewater with ferrous ions can be oxidized and recycled.

Description

technical field [0001] The invention relates to the preparation of compounds, in particular to a preparation method of electronic grade 2,2'-binaphthol. Background technique [0002] 2,2'-Binaphthalene-2,2'-diol (BINOL or BINOL for short) is a typical chiral compound, which is used to prepare chiral reagent (R)-(+)-BINOL after resolution And (S)-(-)-BINOL, while (R)-(+)-BINOL or (S)-(-)-BINOL is a chiral inducer and resolution agent (such as the resolution of omeprazole) At the same time, it is also a raw material for the synthesis of chiral catalyst ligands such as widely used BINAP and chiral crown ethers, and now 2,2'-binaphthol is used as a raw material for the synthesis of electronic chemicals such as liquid crystals and optical films. Its demand is expanding rapidly, and the market prospect is broad, and the raw materials used in electronic chemicals have higher requirements on the purity of raw materials. [0003] The synthetic method of 2,2'-binaphthol mainly conta...

Claims

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Application Information

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IPC IPC(8): C07C37/11C07C39/14
CPCC07C37/11C07C39/14
Inventor 浜田申一浜田智子唐成见
Owner YWK CHEM TAICANG
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