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High-yield vanillin synthesis process

A synthesis process and vanillin technology are applied in the field of vanillin synthesis technology and high-yield vanillin synthesis technology, which can solve problems such as unsatisfactory yield, difficulty in separation and purification, and achieve less by-products and strong reference Significance, effect of mild reaction conditions

Active Publication Date: 2021-05-21
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the overall yield is still not ideal enough, only reaching 76%. In addition, the biggest problem of this method is to generate more than 20% of ortho-vanillin, and the boiling points of vanillin and ortho-vanillin are not much different, and vanillin It is a heat-sensitive material, which will cause greater difficulties in the later separation and purification

Method used

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  • High-yield vanillin synthesis process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]In a three-mouth flask with a thermometer, 17.5 g of pyridine, 300 g of tetrahydrofuran was added, and 20 g was slowly added 20 g from 98% concentrated sulfuric acid to the reaction system at 0 ° C to obtain a pyridine complex, and the elemental analysis is as follows: C37.49%, H 3.78%, N 8.74%, O 29.97%, S 20.02%. Then, 50 g of a cew pony phenol was added dropwise, and then the reaction was added after 15 min and then added a small amount of water and purified to give the product 1. 50 g of a compound 1 was dissolved in a solution of 120 g of ethanol, and 171.5 g 40% sodium hydroxide solution and 71.6 g of trichloromethane were added thereto, and the heated to 70 ° C, and the reaction was reacted under this condition, and purified to obtain Compound 2. Element analysis is as follows: C 41.38%, H 3.47%, O 41.34%, S13.81%, and the nuclear magnetic results are as follows:1H NMR (600MHz, CDCL3: Δ2.0 (1H), 3.83 (3H), 5.35 (1H), 7.27 (1H), 7.73 (1H), 9.88 (1H). 40 g of 50 g of Comp...

Embodiment 2

[0048]In a three-mouth flask with a thermometer, 41.2 g of 2-methylpyridine, 300 g of toluene was added, and 112 g of 70% concentrated sulfuric acid was slowly added dropwise to the reaction system at 0 ° C ice bath conditions to obtain a pyrix sulfonic acid complex. Elemental analysis is as follows: C41.37%, H 4.63%, N 8.04%, O 27.55%, S 18.41%. Then, 50 g of cewulphenol was added dropwise, and then the reaction was added after 50 min and then added a small amount of water and purified to obtain Compound 1. 50 g of compound 1 was dissolved in a 120 g of aqueous methanol solution, and 220.5 g 40% sodium hydroxide solution was added thereto and 114.6 g of trichloromethane, heated to 50 ° C, and reacted under this condition for 12 h, separated purification to obtain Compound 2. 40 g of 50 g of Compound 2 was dissolved in 200 g of water, stirred with a small amount of 30% dilute sulfuric acid to pH to 2.5, 50 min, and a gray oily liquid was precipitated, and a certain amount of acetate...

Embodiment 3

[0050]In a three-mouth flask with a thermometer, 51.5 g of 3-methylpyridine, 300 g of tetrahydrofuran was added. Under -10 ° C, 79.5 g 50% concentrated sulfuric acid was slowly added dropwise to obtain a pyrix sulfonate complex. Elemental analysis is as follows: C41.37%, H 4.63%, N 8.04%, O 27.55%, S 18.41%. Then, 50 g of a cew pony phenol was added dropwise, and after the addition was added, it was added after 40 min and then added a small amount of water, and purified to obtain Compound 1. 50 g of compound 1 was dissolved in 120 g of an aqueous solution of ethanol, and 196 g 40% sodium hydroxide solution and 86 g of chloroform were added thereto, and heated to 60 ° C, and the reaction was reacted under this condition, and purified to obtain Compound 2. 40 g of 50 g of Compound 2 was dissolved in 200 g of water, and stirred at a small amount of 30% dilute sulfate to pH to 1.5, 30 min, and a gray oily liquid was precipitated, and a certain amount of tare acetate was added to the oil...

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Abstract

The invention provides a high-yield vanillin synthesis process which comprises the following steps: 1) mixing guaiacol, alkyl pyridine and a sulfonating agent to prepare a product 1; 2) adding the product 1 and an inorganic base into a reactor, dropwise adding a formylation reagent, and reacting to obtain a product 2; and 3) dissolving the product 2 in a solvent, adding an acid, heating, stirring, cooling, and purifying to obtain the target product vanillin. The route provided by the invention has the outstanding advantages of fewer byproducts, high synthesis yield, mild reaction conditions and the like, also solves the problem of low sulfonation para-position yield, and has stronger reference significance.

Description

Technical field[0001]The present invention relates to a vanillin synthesis process, and more particularly to a high yield with a thromella synthesis process, which belongs to the field of organic synthesis.Background technique[0002]Vinyllain is also known as vanillice, is currently the largest edible synthetic fragrance in the world, with an annual consumption of approximately 28,000 tons. The acquisition of Viangland is mainly natural extraction, chemical synthesis, and three types of biological fermentation. Among them, chemical synthesis is the broadest channel of Vinyllain. The manufacturing method can be divided into a cerium phenolic method, a phenol method, lignin method, pine cypress, butum phenolic, hydroxybenzal aldehyde method, yellow Verne method, etc. The healing pollen is a mainstream of the vanosin synthesis process due to its low price, and has gradually become the mainstream of the vanosin synthesis process. Currently more than 90% of the Vinyllandin manufacturers u...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/65C07C47/58
CPCC07C45/65C07C303/22C07C303/06C07C47/58C07C309/44C07C309/42
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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