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Method for preparing 3-methylcrotonaldehyde from isopentenyl alcohol through catalytic oxidation with gold catalyst

A technology for preparing prenylal and gold catalysts from prenol, which is applied in chemical instruments and methods, metal/metal oxide/metal hydroxide catalysts, physical/chemical process catalysts, etc., and can solve serious environmental pollution, The catalyst is expensive, and the separation of chromium-containing catalysts is difficult, etc.

Active Publication Date: 2019-03-05
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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  • Method for preparing 3-methylcrotonaldehyde from isopentenyl alcohol through catalytic oxidation with gold catalyst
  • Method for preparing 3-methylcrotonaldehyde from isopentenyl alcohol through catalytic oxidation with gold catalyst

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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] Catalyst preparation: prepare nano-gold particles with a particle size of about 2.0nm by colloidal method, then load the gold colloid on the modified alumina carrier under the condition of stirring, filter and wash, and vacuum-dry. Baking at 350 degrees in air for 4 hours to remove ligands. A series of nano-gold catalysts with different loads were obtained. The loading of gold is 0.1%-5%.

Embodiment 2

[0013] 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 sodium-modified alumina-supported gold catalyst with a filling volume of 1 ml and an enol flow rate of 0.05 ml / min. The air flow rate was 24ml / min, and the reaction temperature was 250°C. Before the reaction, prenol is preheated through a 180-degree preheating furnace and then passes through the reactor. Utilize gas chromatography after the reaction to carry out product qualitative and quantitative analysis (Table 1), can see that the addition of sodium can improve the selectivity of product from the table, when sodium content is 1.5%, the selectivity of product is the highest is 99.4%.

Embodiment 3

[0015] Catalytic conversion experiment: Prenyl alcohol oxidation experiment was carried out in a stainless steel tube reactor with an inner diameter of 6 mm. The catalyst was a magnesium-modified alumina-supported gold catalyst with a filling volume of 1 ml and an enol flow rate of 0.05 ml / min. The air flow rate was 24ml / min, and the reaction temperature was 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 (Table 2). It can be seen that the modification of magnesium can also improve the selectivity of prenaldehyde, and the product selectivity can reach up to 99.2%.

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Abstract

The invention provides a method for preparing 3-methylcrotonaldehyde from isopentenyl alcohol through catalytic oxidation with a supported gold catalyst. The catalyst is an Al2O3 supported gold catalyst. The alumina support of the catalyst is modified by Na, Mg, K, Cs and other alkali metals, and the supported gold is used as an active component, wherein gold is a main active component, and the gold support percentage is 0.1-5%, and alkali metal and alkaline-earth metal oxides are used as an aid, and the content of the aid is 0.01-2%. The catalyst is used for preparing 3-methyl-2-buten-1-al (3-methylcrotonaldehyde) from 3-methyl-2-buten-1-ol (isopentenyl alcohol) through oxidative dehydrogenation. The oxidative dehydrogenation of 3-methyl-2-buten-1-ol can be achieved at lower temperature,and the selectivity of the product 3-methylcrotonaldehyde is up to 99%.

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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IPC IPC(8): C07C45/38C07C47/21B01J23/66
CPCB01J23/66C07C45/38C07C47/21
Inventor 黄家辉张军营洪峰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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