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A kind of technology that adopts catalytic oxidation method to synthesize vanillin

A technology of catalytic oxidation and vanillin, applied in fermentation and other directions, can solve the problems of unstable product quality and low yield of the process route, and achieve the effects of easy amplification, simple process operation and simple reaction steps.

Active Publication Date: 2018-01-30
BOTON SHANGHAI BIOLOGICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Of course, there are still deficiencies in the current biosynthesis method for preparing vanillin, such as "Preparation Process for Aryl Carbonyl Compounds from Alkenes" (US6331655, U.S. Patent) and "A Method for Preparing Vanillin" (Chinese Patent, CN102367222) respectively adopt lipase and hemoglobin as biocatalysts, catalyze hydrogen peroxide to oxidize isoeugenol to prepare vanillin, although the reaction steps are simple, the conditions are mild, and the time is short, but due to the low yield (40-55%) of the process route, the product Unstable quality and other shortcomings, it is difficult to scale up industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 1. In a 100ml three-neck flask, add isoeugenol (0.1mol, 16.4g), lipase Novozyme 435 (0.16g), under stirring, add diethyl oxalate (0.15mol, 22g) dropwise at 25 degrees to dissolve The addition of urea hydrogen peroxide (0.15mol, 14.1 grams) was completed within 2 hours, and the temperature was kept at 35 degrees for 10 hours of reaction.

[0024] 2. Filtration, separation and recovery of urea and enzyme catalyst. The filtrate was diluted with sulfuric acid aqueous solution, then neutralized by adding saturated sodium bicarbonate solution dropwise, and then washed with sodium periodate.

[0025] 3. Filtrate, add toluene to the filtrate for extraction, recover the toluene from the extract, and crystallize the crude product with edible alcohol to obtain 10.3 g of white needle-like crystals, with a yield of 68%.

Embodiment 2

[0027] 1. In a 100ml three-necked flask, add isoeugenol (0.1mol, 16.4g), lipase (0.5g), under stirring, add oxalic acid (0.15mol, 13.5g) at 15 degrees, and then add the Urea hydrogen oxide (0.15mol, 14.1 grams), 2.82 grams each time, the temperature was kept at 15 degrees, the addition was completed within 2.5 hours, the temperature was kept at 30 degrees, and the reaction was carried out for 24 hours.

[0028] 2. Filtration, separation and recovery of urea and enzyme catalyst. The filtrate was diluted with aqueous citric acid solution, then neutralized by adding saturated potassium bicarbonate solution dropwise, and then washed with sodium periodate.

[0029] 3. Filtrate, add butyl acetate to the filtrate for extraction, recover butyl acetate from the extract, and crystallize the crude product with edible alcohol to obtain 10.9 g of white needle-shaped crystals, with a yield of 72%.

Embodiment 3

[0031] 1. In a 100ml three-necked flask, add isoeugenol (0.1mol, 16.4g), lipase (0.4g), under stirring, add malonic acid (0.075mol, 7.8g) at 20 degrees, and add in 5 times Urea hydrogen peroxide (0.15mol, 14.1 grams), 2.82 grams each time, the temperature was kept at 20 degrees, the addition was completed within 2.5 hours, the temperature was kept at about 20 degrees, and the reaction was carried out for 24 hours.

[0032] 2. Filtration, separation and recovery of urea and enzyme catalyst. The filtrate was diluted with sulfuric acid aqueous solution, then neutralized by adding saturated potassium carbonate solution dropwise, and then washed with sodium periodate.

[0033] 3. Filtrate, add toluene to the filtrate for extraction, recover the toluene from the extract, and crystallize the crude product with edible alcohol to obtain 10.3 g of white needle-like crystals, with a yield of 68%.

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PUM

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Abstract

A process for synthesizing vanillin by catalytic oxidation, the process comprising the following steps: 1) adding isoeugenol, lipase, dibasic acid or dibasic acid derivatives into a reactor, stirring, and controlling the temperature in the reactor 15-35 degrees, add urea hydrogen peroxide, heat up to 15-40 degrees, continue to stir the reaction for 8-24h, filter, separate and recover the filtrate, and obtain the filtrate; 2) the filtrate in step 1) is diluted with acid solution, and Neutralize with liquid, wash with sodium periodate, then extract with organic solvent, recrystallize with edible alcohol at a mass concentration of 30-95%, and dry to obtain vanillin. The vanillin yield of the method can reach 75%, the reaction steps are simple, the conditions are mild, the catalytic specificity is strong, by-products are not easily produced, the product yield is high, the method is friendly to the environment and can be easily scaled up.

Description

technical field [0001] The invention relates to a process for synthesizing vanillin by a catalytic oxidation method, in particular to an enzyme-catalyzed oxidation method. Background technique [0002] Vanillin (Vanillin), also known as vanillin, vanillin, etc., is the main component of vanillin beans, the chemical name is 3-methoxy-4-hydroxybenzaldehyde, the relative molecular weight is 152.1, and the appearance is white To light yellow needle-like crystal or powder, showing the unique aroma of vanilla orchid pods, slightly sweet. Vanillin is one of the largest and most widely used spices in the world. Widely used in chocolate, ice cream, candy and other foods as well as cigarettes, beverages and high-end cosmetics. It can not only be used as a flavor enhancer, but also as a preservative, fresh-keeping agent, antioxidant, flavoring agent or fixative in food, among which beverages, candies, pastries, biscuits, bread and roasted seeds and nuts are mostly used in food, and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P7/24
CPCC12P7/24
Inventor 李斌彭春睿刘旭石化兵
Owner BOTON SHANGHAI BIOLOGICAL TECH CO LTD