Preparation method of catalyst and application of catalyst in preparation of β-isophorone

A technology of isophorone and catalyst, applied in the field of catalyst, can solve the problems of equipment corrosion by strong basic catalyst, low purity of β-isophorone, complicated post-treatment process, etc., so as to reduce the generation of heavy components , the effect of improving the reaction selectivity and the simple preparation method

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

[0004] In view of the complex operation of the above-mentioned isomerization reaction, a large amount of research has been carried out on the catalyst in the prior art, in order to expect to improve the reaction yield:
[0005] U.S. Patent No. 4010205A uses triethanolamine as a catalyst for reactive distillation, and the reaction solution is washed with tartaric acid and brine to obtain β-isophorone; the disadvantage of this technical solution is that the purity of the obtained β-isophorone is relatively low and the The processing process is complex;
[0006] U.S. patents US5907065A and US6005147A use Co 3 o 4 , CaO, Fe 3 o 4 The oxide is used as a catalyst, and the isomerization reaction is carried out by vacuum distillation, and the purity of the obtained β-isophorone can reach more than 97%, but there are many by-products in the reaction and the space-time yield is low;
[0007] Chinese patents CN1288882 and CN1292374 use alkaline hydroxide (KOH, NaOH, etc.) as a catalyst to produce β-isophorone through isomerization reaction, although this technical scheme can obtain β-isophorone with higher purity , but the strong alkaline catalyst will seriously corrode the equipment;
This method also faces problems such as many by-products, low space-time yield, and serious equipment corrosion.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 10g glycine, 100g β-cyclodextrin, 30g DCC, 400mL dichloroethane were added to the 1L reaction flask in turn, stirred at 50°C for 7h, the reaction solution was directly filtered, the filter cake was rinsed with ethanol, and a vacuum drying oven (60°C, 2KPa ) drying to obtain 108 g of glycine-modified esterified β-cyclodextrin. The obtained esterified modified cyclodextrin was transferred to a three-necked flask, 108 g of benzaldehyde and 400 mL of ethanol were added in sequence, stirred at 60 °C for 2 h, the reaction solution was directly filtered, and dried in a vacuum drying oven (60 °C, 2KPa) to obtain 119 g Glycine-based Schiff base-modified β-cyclodextrin, denoted as catalyst A.

[0041] Add α-isophorone containing 0.01 wt% catalyst A to the column kettle of a plate column reactor with 10 plates, and carry out refining at 150 ° C, absolute pressure of 0.01 MPa, and reflux ratio of 1:1. Distillation reaction, isomerization reaction occurs.

Embodiment 2

[0043] Add 10g alanine, 200g β-cyclodextrin, 10g DIC, 400mL dichloroethane to the 1L reaction flask in turn, stir at 20°C for 10h, the reaction solution is directly filtered, the filter cake is rinsed with ethanol, and the vacuum drying oven (60°C) , 2KPa) drying to obtain 208g of alanine-modified esterified β-cyclodextrin. The obtained esterified modified cyclodextrin was transferred to a three-necked flask, 416 g of benzaldehyde and 400 mL of ethanol were added in sequence, stirred at 20 °C for 10 h, the reaction solution was directly filtered, and dried in a vacuum drying oven (60 °C, 2KPa) to obtain 217.9 g Alanine-based Schiff base-modified β-cyclodextrin, denoted as catalyst B.

[0044] Add α-isophorone containing 0.1 wt% catalyst B to the column kettle of the plate column reactor with 25 plates, and carry out refining at 180 ° C, absolute pressure of 0.05 MPa, and reflux ratio of 30:1. Distillation reaction, isomerization reaction occurs.

Embodiment 3

[0046]10g serine, 10g β-cyclodextrin, 50g EDCI, 400mL dichloroethane were added to the 1L reaction flask in turn, stirred at 70°C for 5h, the reaction solution was directly filtered, the filter cake was rinsed with ethanol, and a vacuum drying oven (60°C, 2KPa ) and drying to obtain 19.5 g of serine-modified esterified β-cyclodextrin. Transfer the obtained esterified modified cyclodextrin into a three-necked flask, add 195 g of benzaldehyde and 400 mL of ethanol in turn, stir at 70 °C for 0.5 h, filter the reaction solution directly, and dry in a vacuum drying oven (60 °C, 2KPa) to obtain 27.8 g of serine-based Schiff base-modified beta-cyclodextrin, designated as catalyst C.

[0047] Add α-isophorone containing 0.5wt% catalyst C to the column reactor of the plate column reactor with 30 plates, and carry out refining under the conditions of 220 ° C, absolute pressure of 0.1 MPa, and reflux ratio of 3:1. Distillation reaction, isomerization reaction occurs.

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Abstract

The invention provides a preparation method of a catalyst and application of the catalyst in the preparation of β-isophorone. The preparation method of the catalyst comprises: 1) esterifying β-cyclodextrin and amino acid to obtain amino acid-modified esterified β-cyclodextrin; 2) generating amino acid-modified esterified β-cyclodextrin and aromatic aldehyde A Schiff base reaction is performed to obtain a Schiff base modified esterification β-cyclodextrin catalyst. The present invention also provides a method for preparing β-isophorone by isomerizing α-isophorone under the catalysis of the Schiff base-modified esterified β-cyclodextrin prepared by the above method method. The catalyst prepared by the method of the invention has high selectivity and high yield for the reaction of α-isophorone isomerization to β-isophorone, is not easy to produce by-products, has simple operation, strong industrial applicability, and is suitable for equipment. Corrosion free.

Description

technical field [0001] The invention relates to a cyclodextrin modified catalyst, in particular to a preparation method of a cyclodextrin modified catalyst and the application of the catalyst in the preparation of beta-isophorone, belonging to the technical field of catalysts. Background technique [0002] β-Isophorone (3,5,5-trimethylcyclohex-3-en-1-one) is an important intermediate in the synthesis of vitamin E, carotenoids, astaxanthin and various spices, and is an important intermediate in the synthesis of vitamin E, carotenoids, astaxanthin and various spices. The main raw material for the synthesis of tea ketone (2,6,6-trimethyl-2-cyclohexene-1,4-dione, KIP). [0003] The conventional preparation method of β-isophorone is to use α-isophorone (3,5,5-trimethylcyclohex-2-en-1-one) as raw material, through isomerization under the action of catalyst. chemical reaction is obtained. α-isophorone and β-isophorone are a pair of isomers, and the formation of β-isophorone invol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/06C07C49/603C07C45/67C07C45/82
CPCB01J31/065C07C45/67C07C45/82C07C49/603Y02P20/10
Inventor 刘英瑞鹿宝华宋明焱张涛吕英东郭劲资李莉宋军伟孙犀璨杨宗龙刘齐兴
Owner WANHUA CHEM GRP CO LTD
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