Catalyst for synthesizing 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propanol and preparation and application of catalyst

A technology of hydroxyphenyl and di-tert-butyl, which is applied in the field of catalysts for the synthesis of 3-propanol, can solve problems such as poor activity, carbon-carbon bond breakage of aromatic alcohols, and harsh reaction conditions, and achieve high conversion rate and high conversion rate and selectivity, the effect of excellent selectivity

Active Publication Date: 2020-06-05
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, according to investigations and studies, it has been found that there is currently no efficient synthesis of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate methyl ester at home and abroad. Related technology of hydroxyphenyl) propanol
This is because 3-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl propionate has three functional groups (respectively two tert-butyl groups and a hydroxyl group) on the benzene ring, wherein the The hydroxyl group has an electron-withdrawing effect, which can easily cause the carbon-carbon bond breakage of the product aromatic alcohol obtained during the hydrogenation reaction of the aromatic ester; in addition, there are two tert-butyl groups at the 3 and 5 positions, which form a steric hindrance during the reaction, so that Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate has poor activity and harsh reaction conditions for synthesizing corresponding alcohols

Method used

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  • Catalyst for synthesizing 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propanol and preparation and application of catalyst
  • Catalyst for synthesizing 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propanol and preparation and application of catalyst

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preparation example Construction

[0048] Catalyst for the synthesis of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanol by hydrogenation of methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate A preparation method comprising the steps of:

[0049] (1), take the soluble salt of the active component of formula quantity and the soluble salt of auxiliary agent precursor and dissolve in the solvent to obtain the salt solution;

[0050] (2), take the carrier of formula quantity and join in the saline solution of step (1), mix evenly, obtain mixed solution;

[0051] (3), drying the mixed solution of step (2) at room temperature for 5-120 hours;

[0052] (4), drying the product obtained in step (3) at 80-150°C for 2-60 hours;

[0053] (5), the product obtained in step (4) is roasted for 2 to 38 hours at 200 to 1000° C.;

[0054] (6), add the product obtained in step (5) into a solution containing cetyltrimethylammonium bromide, ammonia, 3-aminophenol, and formaldehyde, and stir at room temperature for 10 to 36 hours...

Embodiment 1

[0059] At room temperature, 3.8 g of copper nitrate and 0.2 g of palladium nitrate were dissolved in 10 mL of deionized water, and 10 g of silica carrier was weighed and placed in the above salt solution. Dry at room temperature for 24 hours, transfer to a blast dryer and dry at 100°C for 4 hours. Then the obtained product was baked at 500°C for 10 h in a muffle furnace. Get 0.5g of the resulting product and place it in a mixed solution containing 0.2g cetyltrimethylammonium bromide, 0.5ml ammonia water (25wt%), 0.1g 3-aminophenol, and 0.11ml formaldehyde, stir at room temperature for 18h, then heat up Stir at 100°C for 5h. After centrifugation, a solid product was obtained and dried at 120°C for 3 hours. The obtained catalyst is Cu-Pd / SiO 2 .

[0060] Take 0.5g of the above catalyst and place it in a high-temperature reduction furnace to activate the catalyst. The activation conditions are as follows: temperature is 300°C, pressure is 0.1MPa, reducing gas is hydrogen, and...

Embodiment 2

[0062] At room temperature, 3.8 g of copper nitrate and 0.2 g of chloroplatinic acid were dissolved in 10 mL of deionized water, and 10 g of silica carrier was weighed and placed in the above salt solution. Dry at room temperature for 24 hours, transfer to a blast dryer and dry at 100°C for 4 hours. Then the obtained product was baked at 500°C for 10 h in a muffle furnace. Get 0.5g of the resulting product and place it in a mixed solution containing 0.2g cetyltrimethylammonium bromide, 0.5ml ammonia water (25wt%), 0.1g 3-aminophenol, and 0.11ml formaldehyde, stir at room temperature for 18h, then heat up Stir at 100°C for 5h. After centrifugation, a solid product was obtained and dried at 120°C for 3 hours. The obtained catalyst is Cu-Pt / SiO 2 .

[0063] Take 0.5g of the above catalyst and place it in a high-temperature reduction furnace to activate the catalyst. The activation conditions are as follows: temperature is 300°C, pressure is 0.1MPa, reducing gas is hydrogen, a...

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Abstract

The invention discloses a catalyst. The main active component is one or two of Cu and Ni, the auxiliary agent is one or more simple substances or oxides of Au, Pt, Ru, Al, Re, B, Mg, Rh, Ir, Mn, La, Pd, Ag, Li, Cr and Ce, and the carrier is one or more of activated carbon, silicon oxide, aluminum oxide, graphite, a molecular sieve, diatomite and a carbon nanotube. The invention also discloses a preparation method and an application thereof. The catalyst provided by the invention has a high conversion rate and selectivity and excellent activity, stability and other properties. According to themethod, the 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propanol is prepared by hydrogenating the methyl 3-(3, 5-di-tert-butyl-4-hydroxyphenyl)propionate for the first time, and the purposes of high conversion rate and selectivity can be achieved under mild conditions through the prepared catalyst.

Description

technical field [0001] The invention relates to the technical field of compound synthesis, in particular to a catalyst for the synthesis of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanol and its preparation and application. Background technique [0002] 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanol, the molecular structure is as follows: [0003] [0004] As an important organic intermediate, 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanol is widely used in pharmaceutical synthesis. Data Voprosy meditsinskoi khimii, 1992, 38 (1): 46-48. Studies have shown that 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propanol plays an obvious role in the study of cholesterol-lowering specific drugs . At present, 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propanol is mainly extracted from plants, which is inefficient and expensive. Methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate, as an excellent intermediate of hindered phenolic antioxidants, has been extensively studied at home and abroad....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/06B01J27/24B01J23/89B01J23/83B01J23/889C07C37/00C07C39/11
CPCB01J31/069B01J27/24B01J23/8926B01J23/83B01J23/8892C07C37/002C07C39/11
Inventor 陈兴坤丁云杰翁高翔杜中南
Owner ZHEJIANG NORMAL UNIVERSITY
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