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A kind of method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone

A technology for oxoisophorone and isophorone, which is applied in the field of catalytic oxidation of β-isophorone to prepare 4-oxoisophorone, can solve the problem that the catalyst is difficult to recycle, the catalyst structure is complex, and the post-treatment Process difficulties and other problems, to achieve the effect of inhibiting transformation and the formation of multimers, improving the probability of contact and effective collision, and maintaining stable catalytic activity

Active Publication Date: 2022-07-12
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest disadvantage of this method is that the reaction is prone to produce o-KIP, an ortho-oxidation by-product, which has similar physical properties to KIP, so it is quite difficult to separate it from the product.
Patent CN1865210 discloses a method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone with arginine as the main structure of the Schiff base complex as a catalyst, although the conversion rate and selectivity of the method are relatively high High, but there is also the problem of complex catalyst structure and difficult preparation
[0007] In addition, as catalysts, transition metal complexes are homogeneous in the reaction process, so it is difficult to recycle the catalyst after the reaction, and it brings difficulties to the post-processing process.
[0008] To sum up, in the existing patented technology of oxidizing β-isophorone to prepare 4-oxoisophorone, there are still defects such as poor reaction selectivity, harsh process conditions, complex catalyst preparation and inability to recycle.

Method used

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  • A kind of method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone
  • A kind of method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone
  • A kind of method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone

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Experimental program
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Effect test

Embodiment 1

[0049] The walnut shells were baked at 120°C to constant weight, crushed and passed through a 160-mesh sieve. The activator adopts the mass fraction of 40% H 3 PO 4 , add 300g of activator to 50g of walnut shell powder, mix and stand for 20h, then dry the mixture at 120℃, and then put it into a tube furnace for high temperature pyrolysis at 550℃ for 1h (nitrogen protection). After cooling to room temperature, the activated carbon was taken out and washed to neutrality. Dry the activated carbon, pulverize it after cooling, pass through a 200-mesh sieve, and put it in a desiccator for later use.

[0050] Weigh 4g Nano Y 2 O 3 , 4g nano ZrO 2 and 50g carrier W-AC were ground in an agate mortar for 30min, transferred into a beaker, added with 300g pure water and stirred for 1h to fully mix the active components and the carrier. The mixed sample after stirring was ultrasonically shaken at a frequency of 100 Hz and 25° C. for 2 h to further fully mix the sample. The samples w...

Embodiment 2

[0053] Adjust W-AC carrier, Y 2 O 3 , ZrO 2 , MgCl 2 The dosages are respectively 50g, 10g, 10g and 0.32g, and the remaining conditions refer to Example 1 to prepare catalyst b. XPS analysis of its composition as W-AC carrier: Y 2 O 3 : ZrO 2 : MgCl 2 =100.20.0:20.0:0.5 (mass ratio).

Embodiment 3

[0055] A reactor equipped with a six-blade turbine high-speed stirring paddle is used as the reactor. 1382g of beta-isophorone, 1658g of acetonitrile, 34.55g of catalyst a, and 41.46g of hydroquinone were added successively to the reactor; electric heating and mechanical stirring were turned on, the temperature of the reaction solution was heated to 30° C., and 2429g 35% was added dropwise. The hydrogen peroxide solution was added dropwise for 8h, and the reaction was continued for 2h. After the reaction, gas chromatography analysis showed that the conversion rate of β-isophorone of the raw material was 99.57%, the selectivity of α-IP was 0.51%, the selectivity of o-KIP was 2.68%, the selectivity of multimers was 1.75%, and the selectivity of KIP was 1.75%. 94.95%, KIP yield 94.54%.

[0056] The reaction solution was filtered, and the catalyst was washed with acetonitrile, dried, and applied in accordance with the conditions of implementation 3. The results are shown in Tabl...

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Abstract

The invention discloses a method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone. The method adopts walnut shell-based activated carbon (W-AC) to support yttria-zirconia-metal halide (M m X n ‑Y 2 O 3 ‑ZrO 2 / W‑AC) as a catalyst. The method comprises the following steps: β-isophorone is subjected to oxidation reaction with hydrogen peroxide in the presence of a solvent, a catalyst and a co-catalyst to obtain 4-oxoisophorone. The method has mild reaction conditions, simple process, high β-isophorone conversion rate and product selectivity, little environmental pollution, and can solve the problem of unrecoverable catalyst.

Description

technical field [0001] The invention belongs to the field of organic intermediate synthesis, in particular to a method for preparing 4-oxoisophorone by catalytic oxidation of β-isophorone. Background technique [0002] 4-Oxoisophorone (KIP for short) is an important organic intermediate, which can be used in the preparation of food flavorings and fragrances, as well as in the synthesis of cosmetics. In addition, 4-oxoisophorone is also an important intermediate in the synthesis of vitamins and carotenoids. [0003] There have been many known methods for the oxidation of β-isophorone to 4-oxoisophorone for a long time. [0004] Described in US4046813A a kind of in the presence of pyridine, using a kind of acetylacetone complex of lead, vanadium, iron, cobalt, manganese etc. as catalyst, catalyzing oxygen oxidation β-isophorone to prepare 4-oxoisophorone keto method. Although this method has a conversion rate of about 100%, there will be conversion of β-IP to α-IP during th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/28C07C49/603B01J31/02B01J27/135
CPCC07C45/28B01J31/0202B01J27/135C07C2601/16B01J2231/70C07C49/603Y02P20/584
Inventor 张弈宇张涛刘英瑞吕英东沈宏强郭劲资宋军伟程晓波杨宗龙黎源
Owner WANHUA CHEM GRP CO LTD