Preparation method of 1, 1, 1-tris (4-hydroxyphenyl) ethane

A technology of hydroxyphenyl and hydroxyacetophenone, applied in the first field, can solve the problems of high price of 3-mercaptopropanesulfonic acid sodium salt, inability to effectively recycle, inability to completely remove, etc., to save the cost of three wastes treatment and product yield The effect of high rate and less side effects

Pending Publication Date: 2022-01-18
烟台海川化学制品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Route 3: US 20060173222 (AdilMinoo Dhalla, Raina Gupta, Gurram Kishan, Yongcheng Li, V.Ramanarayanan), the process uses phenol and acetylacetone as raw materials, uses 3-mercaptopropanesulfonate sodium and ion exchange resin as catalysts, 75 ° C Under reaction 22h obtains 1,1,1,-three (4-hydroxyphenyl) ethane, the price of 3-mercaptopropanesulfonic acid sodium salt used in this reaction is higher, and can not effectively recycle, and causes synthesis cost higher
In addition, a large amount of bisphenol A will also be produced in the reaction, which cannot be completely removed in the later stage, thus affecting the purity of the product

Method used

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  • Preparation method of 1, 1, 1-tris (4-hydroxyphenyl) ethane
  • Preparation method of 1, 1, 1-tris (4-hydroxyphenyl) ethane
  • Preparation method of 1, 1, 1-tris (4-hydroxyphenyl) ethane

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Embodiment 1

[0031] Dissolve titanium sulfate solution in distilled water, add polyethylene glycol solution with a mass fraction of 1% to 2%, add ZSM-5 molecular sieve and stir evenly, then gradually add ammonia water dropwise under strong stirring, form a precipitate and put it in an ice water bath Aging; washing and suction filtration, drying the filter cake at 100°C, grinding it into powder, immersing in 1mol / L sulfuric acid solution for 12 hours, filtering, drying the filter cake at 100°C for 3 hours, and then roasting at 500°C for 5 hours to obtain the solid superacid Scat05.

Embodiment 2

[0033] Weigh 54.4g 4-hydroxyacetophenone, 108.8g dichloroethane, 112.8g phenol, 5g solid acid catalyst SO 4 2- / TiO 2 Add it to a 1000ml three-neck flask, and feed it with a dry and stable nitrogen flow. After the reaction system was raised to an internal temperature of 60°C, it was kept warm for 14 hours and filtered to obtain an orange-yellow solid powder; after methanol was added to filter and recover the solid acid catalyst, after decolorization by activated carbon and sodium borohydride, 39.6 g of off-white powder was obtained by adding water to precipitate 1,1,1 ,-tris(4-hydroxyphenyl)ethane.

[0034] HPLC detected 96.8%, and the yield was 32.3%.

Embodiment 3

[0036] Weigh 54.4g of 4-hydroxyacetophenone, 163.2g of dichloroethane, 225.6g of phenol, and 5g of solid acid catalyst Scat05 into a 1000ml three-necked flask, and pass through a dry and stable nitrogen flow. After the reaction system was raised to an internal temperature of 50°C, it was kept warm for 7 hours, and then filtered to obtain an orange-yellow solid powder; after methanol was added to filter and recover the solid acid catalyst, after decolorization by activated carbon and sodium borohydride, 98.8 g of off-white powder was obtained by adding water to precipitate 1,1,1 ,-tris(4-hydroxyphenyl)ethane. The HPLC detection is 99.59%, and the yield is 80.62%.

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Abstract

The invention relates to a preparation method of 1, 1, 1-tris (4-hydroxyphenyl) ethane, and the method comprises the following steps: taking phenol and 4-hydroxyacetophenone as raw materials, adding a water-carrying agent and a precipitating agent into a system before reaction, and taking solid superacid as a catalyst, and performing reacting and recrystallizing to obtain the 1, 1, 1-tris (4-hydroxyphenyl) ethane, wherein the solid superacid is a novel solid superacid Scat05 obtained by introducing a ZSM-5 molecular sieve into SO42-/TiO2. The precipitation agent and the water-carrying agent are added in advance, so that the reaction is carried out in a positive direction. The novel solid superacid Scat05 can effectively accelerate the reaction progress, is small in corrosion to equipment, is not easy to cause side reaction, and can be effectively separated from a product for recycling after reaction, so that the production cost and the three-waste treatment cost are saved. The operation process is simple and safe, the product yield is high, the production period is short, and the method is suitable for industrial application.

Description

technical field [0001] The invention relates to a preparation method of 1,1,1,-tris(4-hydroxyphenyl)ethane, which belongs to the technical field of organic chemical synthesis methods. Background technique [0002] 1,1,1,-tris(4-hydroxyphenyl)ethane is an important trifunctional phenolic compound. It can be used as a branching agent or crosslinking agent for polycarbonate, and the branched siloxane-based polycarbonate made of it has better fluidity, thermal stability and more Low hygroscopicity. It can also be used to polymerize to form cross-linked polycarbonate or copolymerize with other compounds to form polycarbonate. The thermal stability temperature of cross-linked polycarbonate in air is as high as 350°C, and the glass transition temperature reaches 205°C. At the same time, 1,1,1,-tris(4-hydroxyphenyl)ethane is also an important chemical intermediate, which reacts with diphenyl(4-bromomethylphenyl)phosphine to form a phosphorus-containing dendritic compounds, have b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/20C07C39/16B01J29/40B01J27/053
CPCC07C37/20B01J29/40B01J27/053C07C39/16
Inventor 张钊李军赵青山李宏洋王文涛王建忠张维维
Owner 烟台海川化学制品有限公司
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