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A kind of vanillin synthesis catalyst and preparation method thereof

A catalyst and a technology for vanillin, applied in the field of vanillin synthesis catalyst and its preparation and preparation, can solve the problems of low vanillin yield, reduced reaction time, over-oxidation and the like, achieve simple process, improve production efficiency and Yield, the effect of improving yield

Active Publication Date: 2022-04-22
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The glyoxylic acid method has the following problems: 1. The selectivity of the condensation reaction is low, and a large number of ortho by-products and di-condensation by-products are generated, and the condensation by-products are difficult to recover, resulting in high COD of wastewater; 2. The mainstream oxidation process is still Using copper oxide as an oxidant, although it has a high yield, the reaction rate is slow, and a large amount of copper oxide needs to be added to participate in the reaction, and a large amount of cuprous oxide is produced by-product, which brings great harm to the filtration and regeneration of the oxidant in the later stage. many inconveniences
This process route is simple, directly oxidize after recovering guaiacol under acidic conditions, which not only reduces the consumption of lye, but also can obtain vanillin in one step of oxidation, but the biggest disadvantage is that vanillin is unstable Further reaction under the conditions, resulting in lower yield of vanillin
Chinese patent CN102260150A discloses a high-efficiency oxidation method for mandelic acid aqueous solution. A self-priming reactor is used to feed oxygen, which effectively reduces the reaction time and realizes catalyst recycling. However, it is difficult to control the reaction end point and prone to insufficient oxidation or excessive oxidation. The problem

Method used

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  • A kind of vanillin synthesis catalyst and preparation method thereof
  • A kind of vanillin synthesis catalyst and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Catalyst preparation:

[0031] Pour pyridine and tetrahydrofuran solvents into a water-free and oxygen-free airtight three-neck flask, and slowly add butyllithium solution dropwise to the reaction system at -100°C. Quickly add trimethyltin chloride solution to the mixture, raise the temperature to 80°C for 6 hours, separate and purify to obtain the product 1. The added molar ratio of pyridine, trimethyltin chloride, and butyllithium is 1:1:1.

[0032] The product 1 was dissolved in toluene solution, 2-bromo-4sulfonic acid pyridine was added thereto, heated to 60°C and refluxed for 12 hours, and the product 2 was obtained by separation and purification. The added molar ratio of the 2-bromo-4sulfonic acid pyridine to the product 1 is 2:1. Product 2 is carried out proton nuclear magnetic resonance spectrum analysis, and the results are as follows: 1 H NMR (600MHz, CDCl 3 ): δ2.0(2H), 7.79(2H), 7.82(1H), 8.69(2H), 9.04(2H), 9.17(2H).

[0033] Mix product 2 and ferrous ...

Embodiment 2

[0035] Catalyst preparation:

[0036] Inject 4-picoline and tetrahydrofuran solvent into a water-free and oxygen-free airtight three-neck flask, slowly add butyllithium solution dropwise to the reaction system at -80°C, after the dropwise addition, raise to room temperature and continue the reaction for 3h , quickly added trimethyltin chloride solution to the reaction bottle, raised the temperature to 50°C for 8 hours, and separated and purified to obtain product 1. The molar ratio of 4-picoline, trimethyltin chloride and butyllithium is 1:1:2

[0037] The product 1 was dissolved in toluene solution, 2-bromo-3-methyl-4-sulfonic acid pyridine was added thereto, heated to 200° C. for reflux reaction for 12 hours, and the product 2 was obtained by separation and purification. The added molar ratio of the 2-bromo-3-methyl-4sulfonic acid pyridine to the product 1 is 5:1. Product 2 is carried out proton nuclear magnetic resonance spectrum analysis, and the results are as follows: ...

Embodiment 3

[0040] Catalyst preparation:

[0041]Inject 4-ethylpyridine and tetrahydrofuran solvent into a water-free and oxygen-free airtight three-neck flask, slowly add butyllithium solution dropwise to the reaction system at -50°C, after the dropwise addition, raise to room temperature and continue the reaction for 3h , quickly added trimethyltin chloride solution to the reaction flask, raised the temperature to 30°C for 12 hours, and separated and purified to obtain product 1. The added molar ratio of 4-ethylpyridine, trimethyltin chloride, and butyllithium is 1:2:2

[0042] The product 1 was dissolved in toluene solution, 2-bromo-4sulfonic acid-5-picoline was added thereto, heated to 80° C. and refluxed for 12 hours, and the product 2 was obtained by separation and purification. The added molar ratio of the 2-bromo-4sulfonic acid-5-picoline to the product 1 is 2.5:1. Product 2 is carried out proton nuclear magnetic resonance spectrum analysis, and the results are as follows: 1 H ...

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Abstract

The invention provides a vanillin synthesis catalyst and a preparation method thereof. The catalyst is a coordination compound with the following structural expression: the preparation method of the catalyst comprises: 1) adding butyllithium dropwise to an alkylpyridine In, add trimethyltin chloride again, react to obtain product 1; 2) mix product 1, 2-bromo-4-sulfonic acid pyridine compound, catalyst, react to obtain product 2; 3) ferrous iron Compound and product 2 are mixed and stirred in a solvent to prepare the catalyst. By synthesizing an iron ligand catalyst and applying it to the synthesis process of vanillin glyoxylic acid method, the invention can greatly improve the yield of oxidation reaction and condensation reaction, thereby improving the production efficiency and yield of vanillin , has the advantages of simple process and no additional introduction of unnecessary impurities, and is suitable for a wide range of industrial applications.

Description

technical field [0001] The invention relates to a preparation method, in particular to a vanillin synthesis catalyst and a preparation method thereof, belonging to the technical field of catalysts. Background technique [0002] Vanillin, commonly known as vanillin, chemically named 3-methoxy-4-hydroxybenzaldehyde, has the unique aroma of vanilla, usually white or light yellow crystalline powder, and is the largest synthetic fragrance in the world. The global annual production capacity is about 30,000 tons. At present, more than 80% of vanillin is synthesized by glyoxylic acid route, which includes the steps of glyoxylic acid condensation, mandelic acid oxidation and acidification decarboxylation. The glyoxylic acid method has the following problems: 1. The selectivity of the condensation reaction is low, and a large number of ortho by-products and di-condensation by-products are generated, and the condensation by-products are difficult to recover, resulting in high COD of w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J31/22C07D213/71C07C51/367C07C65/21C07C45/67C07C47/58
CPCC07C51/367C07C45/676B01J31/1815C07D213/71B01J2531/842B01J2531/0241B01J2231/4205B01J2231/70C07C65/21C07C47/58
Inventor 丁大康付松林建东冯民昌王锐李俊平黎源
Owner WANHUA CHEM GRP CO LTD
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