A kind of method that catalyzes prenyl alcohol to prepare prenyl aldehyde

A technology for preparing prenylal and catalytic oxidation of prenol, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of expensive catalysts, low yield of prenal, Problems such as difficulty in separation of chromium-containing catalysts

Active Publication Date: 2021-11-09
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

And DE-2517859 reacts with copper as catalyst and can also obtain prenal, but selectivity is relatively poor
Platinum black can be used as the catalyzer of prenol oxidation equally, with platinum black as catalyzer, with hydrogen peroxide as oxygenant, can obtain the prenyl aldehyde yield of 91%, but this catalyst price is comparatively expensive (Chemical Communication (2007), 42;4399-4400)
Pyridinium chlorochromate can also be used to oxidize prenol to prepare prenal, but the yield of prenal in this catalytic process is low, and the separation of homogeneous chromium-containing catalysts is difficult, and the environmental pollution is serious

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Catalyst support preparation: modify the alumina support by the equal volume impregnation method to obtain a series of alumina supports modified by alkali metal or alkaline earth metal oxides: Na / Al 2 o 3 , Mg / Al 2 o 3 , K / Al 2 o 3 , Ca / Al 2 o 3 ,La / Al 2 o 3 ,Zn / Al 2 o 3 , etc., the loading of additives in the catalyst is 0.01% to 5%.

[0011] The preparation of the loading of the secondary active components of the catalyst: the modified alumina carrier is loaded with the secondary active components by the equal volume impregnation method to obtain a series of catalysts with copper, silver, nickel and palladium as the secondary active components. The loading amount of secondary active components in the medium is 0.5%-5%.

[0012] Catalyst preparation: The main active component gold was loaded by a modified impregnation method. Before loading, the pH of the gold solution was adjusted to about 8 with sodium carbonate solution. Then the modified carrier was ad...

Embodiment 2

[0014] Catalytic conversion experiment: The prenol oxidation experiment was carried out in a stainless steel tube reactor with an inner diameter of 6 mm. The catalyst was a gold-copper bimetallic catalyst supported by alumina. The filling volume was 1 ml, the enol flow rate was 0.05 ml / min, The flow rate is 24ml / min, and the reaction temperature is 250°C. Before the reaction, prenol is preheated through a 180-degree preheating furnace and then passes through the reactor. After the reaction, the qualitative and quantitative analysis of the product was carried out by gas chromatography. It can be seen from Table 1 that the addition of copper greatly improves the selectivity of the product. When the copper content is 1%, the selectivity of prenaldehyde is up to 96%.

Embodiment 3

[0016] Catalytic conversion experiment: The prenol oxidation experiment was carried out in a stainless steel tube reactor with an inner diameter of 6mm. The catalyst was a gold-silver bimetallic catalyst supported by alumina. The loading volume was 1ml, the enol flow rate was 0.05ml / min, and the air flow rate was 24ml / min, the reaction temperature is 250°C. Before the reaction, prenol is preheated through a 180-degree preheating furnace and then passes through the reactor. After the reaction, the qualitative and quantitative analysis of the product was carried out by gas chromatography. It was found that the addition of silver would slightly reduce the conversion rate of the reactant, but the selectivity of prenaldehyde was improved to a certain extent.

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Abstract

The invention provides a method for preparing prenal by catalyzing the oxidation of prenol by a supported gold catalyst. The catalyst is a gold catalyst supported by Al2O3 or a bimetallic catalyst composed of gold and cheap metals. The alumina carrier of the catalyst is modified by alkali metals such as Na, Mg, K, and Cs, and one or two of gold, palladium, silver, and copper are loaded as active components. Among them, gold is the main active component, and its loading percentage is 0.1%-5%, and the secondary active components such as silver and copper are loaded at 0.1%-2%. Catalyst is used for the reaction of 3-methyl-2-butene-1-aldehyde (prenyl aldehyde) by oxidative dehydrogenation of 3-methyl-2-butene-alcohol (prenyl alcohol), at lower temperature The oxidative dehydrogenation of 3-methyl-2-buten-alcohol can be realized under the following conditions, and the selectivity of its product prenaldehyde is as high as 98%.

Description

technical field [0001] The invention relates to a method for preparing prenyl aldehyde by catalyzing the oxidation of prenol by a gold catalyst. Background technique [0002] Prenaldehyde is an important pharmaceutical and fragrance intermediate. It can be used to produce citral, isophytol (the main intermediate of VE), vitamin A, carotenoid intermediate, rubber monomer, etc. At the same time, it can be used to produce spices such as damascenone. [0003] At present, there are mainly the following methods for industrially producing prenyl aldehyde: Prenyl alcohol is used as raw material to prepare prenyl aldehyde through catalytic oxidation. JP-60 / 246340 reported the oxidation of prenol to prenal with a supported silver and copper composite catalyst at high temperature, with a selectivity as high as 96%. And DE-2517859 reacts with copper as a catalyst and can also obtain prenal, but the selectivity is poor. Platinum black can be used as the catalyzer of prenol oxidation ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/38C07C47/21B01J23/89B01J23/66
CPCB01J23/66B01J23/8946C07C45/38C07C47/21
Inventor 黄家辉张军营洪峰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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