Preparation method for 4-biphenyl methyl glycidyl ether

Abstract

A preparation method for a 4-biphenyl methyl glycidyl ether, comprising: uniformly mixing 4-biphenylmethanol, epichlorohydrin and a catalyst at 10-15℃; adding solid sodium hydroxide in batches within 1-2 h, and after the sodium hydroxide is added, heating to 25-35℃ for reaction for 12 h; when the concentration of an organic solvent is less than 5%, first adding ionized water and stirring for 30 min to separate out an organic phase, and then using deionized water to wash the organic phase twice; and at 70℃ or below, first carrying out reduced pressure distillation to recover the epichlorohydrin in the organic phase, and then carrying out reduced pressure distillation to obtain the 4-biphenyl methyl glycidyl ether. According to the prepared 4-biphenyl methyl glycidyl ether, the raw materials are easily obtained, the cost is low, the conditions are mild, the process is simple and convenient, and the yield and purity of the obtained product are high, wherein the purity reaches 98.3% or more and the yield can reach 86.5% or more. The present invention relates to the field of organic synthesis.

Description

A preparation method of 4-biphenylmethyl glycidyl ether Technical Field

[0001] The invention relates to the field of organic synthesis, and in particular to a method for preparing 4-biphenylmethyl glycidyl ether. Background Art

[0002] In recent years, with the rapid development of smart phones, the demand for various electronic materials has also increased day by day. Since epoxy resin cured products have good chemical stability, electrical insulation, corrosion resistance, adhesion and mechanical strength, they are widely used in the fields of chemical industry, electronics, electrical appliances, water conservancy, transportation and aerospace. An important use of epoxy resin in the electrical and electronic industry is as a packaging material for semiconductor electronic devices. Due to the rapid development of the electronics and electrical appliance industries, technological updates are very rapid, so the epoxy resin materials supporting them are faced with the problem of high performance. 4-Biphenylmethyl glycidyl ether is a resin material monomer with good performance, and the annual demand at home and abroad is also increasing rapidly. At present, there are few public literature reports on the synthesis of 4-biphenylmethyl glycidyl ether. The present invention provides a 4-biphenylmethyl glycidyl ether and a preparation method thereof. Summary of the Invention

[0003] In response to the above technical problems, the present invention provides a 4-biphenylmethyl glycidyl ether and a preparation method thereof. The method comprises the following steps:

[0004] S1: Evenly mix 4-biphenylmethanol, epichlorohydrin, and the catalyst at 10°C to 15°C, and add solid sodium hydroxide in batches within 1 to 2 hours;

[0005] S2: After adding sodium hydroxide, heat to 25-35°C and react for 12 hours. When the organic solvent concentration is less than 5%, add deionized water and stir for 30 minutes to precipitate the organic phase. Then wash the organic phase twice with deionized water. At below 70°, first recover the epichlorohydrin in the organic phase by vacuum distillation, and then vacuum distill off 4-diphenylmethyl glycidyl ether.

[0006] Furthermore, the molar ratio of the 4-biphenylmethanol, epichlorohydrin, and sodium hydroxide is 1:4-6:1-2, and the amount of the catalyst is 1%-5% of the weight of the 4-biphenylmethanol.

[0007] Furthermore, the amount of deionized water added each time is 1.5 to 2 times the weight of 4-biphenylmethanol.

[0008] Furthermore, the catalyst includes one or more of tetrabutylammonium bromide, benzyltriethylammonium chloride, tetrabutylammonium chloride, and polyethylene glycol.

[0009] Beneficial effects of the present invention:

[0010] The 4-biphenylmethyl glycidyl ether prepared by the present invention has readily available, low-cost raw materials, mild conditions, and a simple process. The resulting product has high yield and purity, and without further purification, the purity reaches over 98.3% and the yield can reach over 86.5%. This method is the first patent document in China reporting a synthesis technology for 4-biphenylmethyl glycidyl ether, indicating a feasible technical direction for the future industrial large-scale production of 4-biphenylmethyl glycidyl ether, providing good guidance and enlightenment, and has great prospects for industrial application. BRIEF DESCRIPTION OF THE DRAWINGS

[0011] FIG1 is a schematic diagram of the synthesis pathway of 4-biphenylmethyl glycidyl ether of the present invention. DETAILED DESCRIPTION

[0012] If the specific conditions are not specified in the examples, the experiments were carried out under conventional conditions or the conditions recommended by the manufacturer. If the manufacturer of the reagents or instruments is not specified, they are all conventional products that can be purchased commercially. The molecular structure of 4-biphenylmethyl glycidyl ether is:

[0013]

[0014] Example 1:

[0015] 4-Biphenylmethanol (184g, 1.0mol), epichlorohydrin (370.0g, 4.0mol), and catalyst tetrabutylammonium bromide (1.84g) were mixed uniformly, cooled to 10 degrees Celsius with stirring, and sodium hydroxide (40g, 1.0mol) was slowly added in batches. The temperature was controlled at 10-15 degrees Celsius. The sodium hydroxide was added in batches within 1 hour. After the addition, the temperature was raised to 25 degrees Celsius and the reaction was carried out for 12 hours. When the organic solvent concentration was less than 0.5%, 276g of deionized water was added and stirred for 30 minutes to precipitate the organic phase. The organic phase was washed twice with 276g of deionized water and the organic phase was collected. The organic phase was first decompressed and distilled at 7800Pa to recover epichlorohydrin below 70°C, and then 4-biphenylmethyl glycidyl ether was distilled off under high vacuum at 40Pa. The main distillate was about 210g (yield: 86.5%, purity: 98.3%).

[0016] Example 2:

[0017] 4-Biphenylmethanol (184g, 1.0mol), epichlorohydrin (462.5g, 5.0mol), and catalyst tetrabutylammonium bromide (5.5g) were mixed uniformly, cooled to 10 degrees under stirring, and sodium hydroxide (48g, 1.2mol) was slowly added in batches. The temperature was controlled at 10-15 degrees. The addition was completed in about 1.5 hours. After the addition, the temperature was raised to 25 degrees and the reaction was carried out for 12 hours. Sampling was tested. When the organic solvent concentration was less than 0.5%, 300g of deionized water was added and stirred for 30 minutes to precipitate the organic phase. The organic phase was washed twice with 300g of deionized water and the organic phase was collected. The organic phase was first reduced pressure at 8200Pa and distilled to recover epichlorohydrin below 770℃, and then 4-biphenylmethyl glycidyl ether was distilled off under high vacuum at 40Pa. About 210g of the main distillate was collected (yield: 87.4%, purity: 99.6%).

[0018] Example 3:

[0019] 4-Biphenylmethanol (184g, 1.0mol), epichlorohydrin (555g, 6mol), and catalyst tetrabutylammonium bromide (9.2g) were mixed evenly, cooled to 10 degrees with stirring, and sodium hydroxide (80g, 2mol) was slowly added in batches. The temperature was controlled at 10-15 degrees. The addition was completed in about 2 hours. After the addition, the temperature was raised to 35 degrees and the reaction was carried out for 12 hours. Sampling was tested. When the organic solvent concentration was less than 0.5%, 368g of deionized water was added and stirred for 30 minutes to precipitate the organic phase. The organic phase was washed twice with 368g of deionized water and the organic phase was collected. The organic phase was first reduced in pressure at 8000Pa and distilled to recover epichlorohydrin at below 70°C, and then 4-biphenylmethyl glycidyl ether was distilled out under high vacuum at 40Pa. The main distillate was about 215g (yield: 92.1%, purity: 99.4%).

[0020] Example 4:

[0021] 4-Biphenylmethanol (500g, 2.72mol), epichlorohydrin (1250g, 13.51mol), and catalyst tetrabutylammonium bromide (15g) were mixed uniformly, cooled to 10 degrees under stirring, and sodium hydroxide (130.4g, 3.26mol) was slowly added in batches. The temperature was controlled at 10-15 degrees. The addition was completed in about 1.5 hours. After the addition, the temperature was raised to 25 degrees and the reaction was carried out for 12 hours. Sampling was performed for detection. When the organic solvent concentration was less than 0.5%, 750g of deionized water was added and stirred for 30 minutes to precipitate the organic phase. The organic phase was washed twice with 750g of deionized water and the organic phase was collected. The organic phase was first decompressed and distilled at 8000Pa to recover epichlorohydrin below 70°C, and then 4-biphenylmethyl glycidyl ether was distilled off under high vacuum at 40Pa. The main distillate was about 598g (yield: 91.6%, purity: 99.6%).

[0022] Example 5:

[0023] 4-Biphenylmethanol (5kg, 27.2mol), epichlorohydrin (12.5kg, 135.1mol), and catalyst tetrabutylammonium bromide (150g) were mixed uniformly, cooled to 10 degrees Celsius with stirring, and sodium hydroxide (1.3kg, 32.5mol) was slowly added in batches. The temperature was controlled at 10-15 degrees Celsius and the addition was completed in about 1.5 hours. After the addition, the temperature was raised to 25 degrees Celsius and the reaction was carried out for 12 hours. Sampling was performed for detection. When the organic solvent concentration was less than 0.5%, 7.5g of deionized water was added and stirred for 30 minutes to precipitate the organic phase. The organic phase was washed twice with 7.5kg of deionized water and the organic phase was collected. The organic phase was first decompressed and distilled at 8000Pa to recover epichlorohydrin below 70°C, and then 4-biphenylmethyl glycidyl ether was distilled off under high vacuum at 40Pa. The main distillate was about 6.05kg (yield: 92.6% and purity: 99.6%).

[0024] The above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit the same. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein. However, these modifications or replacements do not deviate the essence of the corresponding technical solutions from the spirit and scope of the technical solutions of the various embodiments of the present invention.

Claims

1. A method for preparing 4-biphenylmethyl glycidyl ether, characterized in that: The following steps are involved: S1: At 10℃~15℃, evenly mix 4-biphenylmethanol, epichlorohydrin and catalyst, and add solid sodium hydroxide in batches within 1~2h; S2: After adding sodium hydroxide, heat to 25-35°C and react for 12 hours. When the concentration of the organic solvent is less than 5%, add deionized water and stir for 30 minutes to precipitate the organic phase. Wash the organic phase twice with deionized water. At below 70°, first recover the epichlorohydrin in the organic phase by vacuum distillation, and then vacuum distill off 4-biphenylmethyl glycidyl ether.

2. The method for preparing 4-biphenylmethyl glycidyl ether according to claim 1, wherein: The molar ratio of 4-biphenylmethanol, epichlorohydrin and sodium hydroxide is 1:4-6:1-2, and the amount of the catalyst is 1%-5% of the weight of 4-biphenylmethanol.

3. The method for preparing 4-biphenylmethyl glycidyl ether as claimed in claim 1, characterized in that: The amount of deionized water added each time is 1.5 to 2 times the weight of 4-biphenylmethanol.

4. The method for preparing 4-biphenylmethyl glycidyl ether according to claim 1, wherein: The catalyst includes one or more of tetrabutylammonium bromide, benzyltriethylammonium chloride, tetrabutylammonium chloride and polyethylene glycol.

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