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Veratraldehyde preparation method

A technology of veratraldehyde and vanillin, which is applied in the field of preparation of veratraldehyde, can solve the problems of residues, environmental pollution, and inapplicability to industrial production, and achieve the effects of flat yield, environmental friendliness, and simple operation

Inactive Publication Date: 2016-06-01
SHANGHAI AIPU VEGETABLE TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The current main synthesis method of veratraldehyde is to use vanillin as the starting material, react with dimethyl sulfate under the action of a strong base, and because dimethyl sulfate is a highly toxic drug, LD 50 It is 440mg / kg, which is very unsafe during production and use, which is not conducive to industrial production, and there will be residues in the reaction process, which will pollute the environment. In the face of increasingly severe environmental problems, this method is obviously not suitable for industrial production.

Method used

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Experimental program
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Effect test

Embodiment 1

[0012] In the 1000ml three-necked flask equipped with stirring, condenser, thermometer, add 50.6 grams of vanillin, 300 grams of dimethyl carbonate (dimethyl carbonate: vanillin weight ratio is 5.93:1), 46 grams of potassium carbonate and 53.6 gram of tetrabutylammonium bromide (tetrabutylammonium bromide:vanillin weight ratio is 1.06:1), reflux reaction for about 40 hours (about 88 ℃), cooling, add 200ml of clear water to dissolve the solid in the bottle, After decanting, the layers were separated, the aqueous layer was extracted once with toluene, the extract was combined with the upper layer, and washed three times with 200ml salt water until the pH value was neutral. After the solvent was recovered, it was distilled under reduced pressure to obtain 52.32 grams of veratraldehyde with a content of 99.2%, the yield is 94.68%.

Embodiment 2

[0014] In the 1000ml there-necked flask equipped with a condenser, a thermometer adds 50.6 gram of vanillin, 150 gram of dimethyl carbonate (dimethyl carbonate: vanillin weight ratio is 2.96:1), 36.8 gram of potassium carbonate and 43 gram of tetrabutylammonium bromide, reflux for about 30 hours (about 88°C), cool, add 200ml of water to dissolve the solid in the bottle, pour it out and separate the layers, extract the water layer with toluene once, and combine the extract with the upper layer , washed three times with 200ml salt water, washed to a neutral pH value, after recovering the solvent, distilled under reduced pressure to obtain 46.2 grams of veratraldehyde, the content was 99.1%, and the yield was 83.6%.

Embodiment 3

[0016] In the 1000ml there-necked flask equipped with stirring, condenser, thermometer, add 50.6 grams of vanillin, 450 grams of dimethyl carbonate (dimethyl carbonate: vanillin weight ratio is 8.89:1), 55.25 grams of potassium carbonate and 64.4 gram of tetrabutylammonium bromide, reflux for about 50 hours (about 88°C), cool down, add 200ml of clear water to dissolve the solid in the bottle, pour it out and separate the layers, extract the water layer once with toluene, and combine the extract with the upper layer , washed three times with 200ml salt water, washed to a neutral pH value, after recovery of the solvent, vacuum distillation to obtain 50.71 grams of veratraldehyde, the content is 99.12%, and the yield is 91.77%.

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Abstract

The invention relates to a veratraldehyde preparation method. The method is characterized in that under alkaline condition, vanillin and dimethyl carbonate are subjected to a phase-transfer catalytic reaction, a reaction equation is shown in a specification, wherein, a weight ratio of a phase-transfer catalyst to vanillin is 0.85:1 to 1.27:1, a weight ratio of dimethyl carbonate to vanillin is 2.96:1 to 8.89:1, content of the obtained veratraldehyde is 97-99%, the phase-transfer catalyst can be tetrabutylammonium chloride, tetrabutylammonium bromide, polyethylene glycol, and benzyltrimethylammonium chloride, alkali selects potash, sodium carbonate or sodium acetate, the reaction temperature is 20-120 DEG C, and reaction time is 10-100 hours. Compared with a traditional method, the method has the advantages of no toxicity and environmental protection, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a new preparation method of veratraldehyde. Background technique [0002] Veratraldehyde naturally exists in essential oils such as straight citronella oil in a small amount. Veratraldehyde has the aroma of natural vanilla bean and jasmonal, and its appearance is white crystals. Melting point is 42-45°C, boiling point is 281-285°C, FEMA number is 3091, CASNo.120-14-9. [0003] Veratraldehyde is an important synthetic fragrance, which can be widely used in food flavors, and can also be used in daily chemical flavors in a small amount. It is also an important organic intermediate, widely used in the synthesis of medicines and pesticides, such as: hydrochloric acid Synthesis of prazosin, veratramine, lichuanbei and other drugs. [0004] The current main synthesis method of veratraldehyde is to use vanillin as the starting material, react with dimethyl sulfate under the action of strong alkali, and because dimethyl sulfate is a h...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/64
Inventor 王磊王慧辰张爱华
Owner SHANGHAI AIPU VEGETABLE TECH
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