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Method for synthesizing o-vanillin through utilizing 5-aldehyde vanillin

A technology of aldehyde-based vanillin and ortho-vanillin, which is applied in the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problem of high cost, reduce solid waste emissions, and improve economic benefits Effect

Inactive Publication Date: 2013-06-12
JIAXING ZHONGHUA CHEM
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  • Summary
  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

Although there is also a synthetic method for ortho-vanillin, because of its high cost, its main source is obtained by recycling the by-products during the production of vanillin

Method used

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  • Method for synthesizing o-vanillin through utilizing 5-aldehyde vanillin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] In the 1000ml glass there-necked flask, add 200 grams of vanillin by-product solid waste, which contains 5-formyl vanillin (nuclear magnetic spectrum see figure 1 ) about 65%, vanillin 10%. Adding ethanol with a mass ratio of 1: 3.5, heating and dissolving, stirring and cooling to crystallize, and obtaining 105 grams of 5-formyl vanillin after filtration and drying, with a purity of 90% (Note: 5-formyl vanillin contains 5% vanillin Lansu), yield 69%. Add the above-mentioned 5-formyl vanillin and 0.11 g of 10% palladium / carbon catalyst into a 250ml three-necked flask equipped with magnetic stirring and a thermometer, heat to dissolve, turn on magnetic stirring and vacuum, adjust the vacuum to 1-4KPa to control the reaction temperature at Reflux at 180-210° C. for 1-2 hours to carry out catalytic dealdehydeization, and 83 grams of the mixture was obtained from the discharge, with an ortho-vanillin content of 72.1% (note: by-product content of 17% vanillin and 10.8% guaia...

Embodiment 2

[0019] Add 300 grams of vanillin by-product solid waste into a 500 ml glass three-necked flask, which contains about 65% of 5-formyl vanillin and about 10% of vanillin. Direct heating and rectification gave 220 g of 5-formyl vanillin with a purity of 87% (note: 5-formyl vanillin contains 13% vanillin), and a yield of 98%. Add the above-mentioned 5-formyl vanillin and 0.22 g of 10% palladium / carbon catalyst into a 250ml three-neck flask equipped with magnetic stirring and a thermometer, heat to dissolve, turn on magnetic stirring and vacuum, adjust the vacuum to 3-6KPa to control the reaction temperature at Reflux at 200-230° C. for 1-2 hours to carry out catalytic dealdehydeization, and 170 grams of the mixture is obtained from the discharge, and the content of ortho vanillin is 70% (note: the content of by-products is 19% vanillin and 10.8% guaiacol), The conversion rate of ortho-vanillin was 62%. After the distillation, an appropriate amount of ethanol is added to dissolve,...

Embodiment 3

[0021] Add 300 grams of vanillin by-product solid waste into a 500 ml glass three-neck flask, which contains about 50% of 5-formyl vanillin and about 20% of vanillin. Direct heating and distillation gave 200 g of 5-formyl vanillin with a purity of 70% (note: 5-formyl vanillin contains 30% vanillin) and a yield of 93%. Add the above-mentioned 5-formyl vanillin and 0.4 g of platinum / carbon catalyst to a 250ml three-necked flask equipped with magnetic stirring and a thermometer, heat to dissolve, turn on magnetic stirring and vacuum, adjust the vacuum to 5-7KPa to control the reaction temperature at 210- Reflux at 250° C. for 1 to 2 hours to carry out catalytic dealdehydeization, and 120 grams of the mixture obtained from the discharge, the content of ortho-vanillin is 53.1% (note: the by-product content of vanillin is 36.5% and guaiacol 10.3%), and the ortho-vanillin content is 53.1%. The pandan conversion rate was 45.5%. After the distillation, an appropriate amount of ethanol...

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Abstract

The invention discloses a method for converting 5-aldehyde vanillin to o-vanillin. The method is characterized in that a byproduct 5-aldehyde vanillin generated in the vanillin production process through crystallization, distillation or rectification, separation and recovery undergoes catalytic aldehyde removal under a reduced pressure condition to convert to o-vanillin, vanillin and guaiacol. The method realizes the reduction of the discharge of solid wastes, realizes the recycle of the solid wastes generated in the production of vanillin through a glyoxylic acid method, and improves the economic benefit.

Description

technical field [0001] The invention relates to a preparation method of utilizing 5-formyl vanillin, a by-product in the production process of vanillin, and converting it into ortho vanillin. Background technique [0002] O-vanillin [o-vanillin] is an isomer of vanillin, scientific name 2-hydroxy-3-methoxybenzaldehyde, yellow-green needle-like crystal or crystalline powder, melting point 40~ 42°C, boiling point 265.5°C. It can be used as an intermediate in organic synthesis, such as a raw material for the synthesis of berberine. Although vicinal vanillin also has a synthetic method, because of its high cost, its main source is obtained by recycling the by-products during the production of vanillin. Because the proportion of ortho-vanillin in the production process of vanillin is only about 2%, its source is limited, and its selling price is higher than that of vanillin at present. It is very meaningful to find a suitable synthesis method of ortho-vanillin. [0003] Durin...

Claims

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Application Information

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IPC IPC(8): C07C47/58C07C45/67
Inventor 方建业杜德祥梁丽军毛海舫
Owner JIAXING ZHONGHUA CHEM
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