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Method for industrially preparing phenethyl resorcinol based on H2SO4-SiO2 solid acid catalyst

A technology of phenethyl resorcinol and solid acid catalyst, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry and other directions, can solve the problems of oxidative discoloration, corrosion of stainless steel equipment, limited application, etc., and achieve the reaction time Short, avoid strong corrosive effect, low cost of preparation

Inactive Publication Date: 2019-03-29
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that sulfuric acid has oxidative discoloration to the product, severe corrosion to stainless steel equipment, and environmental protection wastewater discharge requirements limit its application

Method used

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  • Method for industrially preparing phenethyl resorcinol based on H2SO4-SiO2 solid acid catalyst
  • Method for industrially preparing phenethyl resorcinol based on H2SO4-SiO2 solid acid catalyst
  • Method for industrially preparing phenethyl resorcinol based on H2SO4-SiO2 solid acid catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 is based on H 2 SO 4 -SiO 2 The method suitable for industrial preparation of phenylethyl resorcinol of solid acid catalyst

[0026] process such as figure 1 As shown, the method is as follows:

[0027] (1) Add 50L of toluene to the reactor, start stirring, add 31.7kg (288mol) of resorcinol (mw: 110.11), 0.15kg of catalyst solid acid H 2 SO 4 -SiO 2 (by mass ratio H 2 SO 4 :SiO2 2 =1:1), after airtight, vacuumize, nitrogen replacement 3 times, under the protection of nitrogen, raise the temperature of the reactor to 95°C, after the temperature is stable, slowly drop 15kg (144mol) of styrene, control the feeding time 1.5 -2 hours, heat preservation reaction for 3 hours, the liquid phase detection reaction is complete, the reaction is stopped, and the yield is 84%.

[0028] (2) Add 10 liters of toluene to the product obtained in step (1), and reclaim the solid acid H by hot filtration 2 SO 4 -SiO 2 Catalyst, set aside, the filtrate was slowly cooled...

Embodiment 2

[0033] (1) The parameters of the design "three factors and two levels" reaction conditions are shown in Table 1, the method is the same as in Example 1, and the results are shown in Table 2.

[0034] Table 1

[0035] level factor

Resorcinol:styrene molar ratio

solid acid H 2 SO 4 -SiO 2 Addition mass%

temperature reflex

1

1:1

0.5

65

2

2.5:1

5

110

[0036] Table 2

[0037]

[0038] As can be seen from Table 1 and Table 2, through the "three factors and two levels" orthogonal experimental design, the priority order of key reaction conditions is: resorcinol: styrene molar ratio > solid acid H 2 SO 4 -SiO 2 Addition amount>reaction temperature.

Embodiment 3

[0040] (1) Add 50L of toluene to the reactor, start stirring, add 39.6kg (360mol) of resorcinol (mw: 110.11), 0.45kg of catalyst solid acid H 2 SO 4 -SiO 2 (by mass ratio H 2 SO 4 :SiO2 2 =1:1), after airtight, vacuumize, nitrogen replacement 3 times, under the protection of nitrogen, the reaction kettle is heated up to 95 ℃, after the temperature is stable, slowly drop 15kg (144mol) of styrene (mw: 104.15) , control the feeding time for 1.5-2 hours, and keep the temperature for 3 hours to react. After the liquid phase detection, the reaction is complete, the yield is 89%, and the reaction is stopped.

[0041] (2) Add 10 liters of toluene to the reaction solution, reclaim the solid acid H by hot filtration 2 SO 4 -SiO 2 Catalyst, the filtrate was slowly cooled to 0°C under stirring conditions, solid resorcinol was precipitated, filtered, and the solid resorcinol was washed and recovered with 12 liters (6 liters×2 times) of toluene for subsequent use. Concentrate the fi...

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Abstract

The invention discloses a method for industrially preparing phenethyl resorcinol based on an H2SO4-SiO2 solid acid catalyst. The phenylethyl resorcinol is synthesized in one step under the catalysis of the high-efficiency solid acid H2SO4-SiO2. The method can be applied to industrial production to achieve high-efficiency production of the phenethyl resorcinol, and can recycle and reuse a resorcinol raw material and an organic solvent under the condition of meeting the advantages of the high-efficiency catalyst in order to achieve the purposes of simplifying the process route and reducing the environmental protection pressure.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and specifically relates to the use of solid acid H 2 SO 4 -SiO 2 As a catalyst, a method for synthesizing phenylethyl resorcinol in one step. Background technique [0002] As a new type of whitening agent, phenylethyl resorcinol is widely used in various whitening, freckle, and anti-aging products. It has become a powerful whitening ingredient in high-end international cosmetics. Its mechanism of action is a tyrosinase inhibitor. It can effectively inhibit the synthesis of melanin by B16 melanoma cells, and its in vitro activity is 210 times that of kojic acid and 32 times that of arbutin. At the same time, phenylethyl resorcinol is also an excellent antioxidant. [0003] At present, the commonly used high-efficiency catalyst for the preparation of phenylethyl (cumyl) phenols is sulfuric acid, and other catalysts such as minerals, activated clay, ion exchange resins, and zeolites replace ino...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/11C07C39/15
CPCC07C37/11C07C39/15
Inventor 周云鹏张秋实
Owner LIAONING UNIVERSITY
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