Piperonal preparation method

A technology of piperonal and glyoxylic acid, applied in the field of medicine and chemical industry, can solve the problems of deep yarn-dyed weaving, low decarboxylation efficiency, easy to produce carbonization, etc.

Inactive Publication Date: 2017-09-29
江西科美香料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing synthetic technology of piperonal usually uses sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid etc. as decarboxylation agent, wherein, phosphoric acid is done decarboxylation agent, even if heated for a long time, decarboxylation efficiency is also very low; Use hydrochloric acid to do decarboxylation agent, require concentration hi...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In a three-neck flask, add 1.5g of water, 10g of glyoxylic acid (40%), and 10g of sulfuric acid under stirring, cool down to 0-5°C, slowly add 6g of piperonylcycline dropwise, keep the reaction for 5 hours, and add 80mL of water to dilute , and suction filtered to obtain 3,4-dimethoxymandelic acid and dilute sulfuric acid mother liquor;

[0014] In a three-neck flask, add 70% dilute sulfuric acid mother liquor, 3,4-dimethoxymandelic acid and 80ml of methylene chloride, add 18mL of 3% dilute nitric acid dropwise at 20°C, after the addition is complete, heat up to 40°C, After reacting for 3 hours, the temperature was lowered to separate the layers, the water layer was separated, the oil layer was washed with water until neutral, and the solvent was evaporated to constant weight under reduced pressure to obtain 6 g of piperonal, with a yield of 81%.

Embodiment 2

[0016] In a three-necked flask, add 1.6g of water, 10.5g of glyoxylic acid, and 10.5g of sulfuric acid under stirring, cool down to 0-5°C, slowly add 6g of piperonylcycline dropwise, and keep it warm for 7 hours, add 90mL of water to dilute, and pump Filter to obtain 3,4-dimethoxymandelic acid and dilute sulfuric acid mother liquor;

[0017] In a three-neck flask, add 50% dilute sulfuric acid mother liquor, 3,4-dimethoxymandelic acid and 80 mL of dichloromethane, add 19 mL of 3% dilute nitric acid dropwise at 20°C, after the addition is complete, heat up to 40°C, After reacting for 3 hours, the temperature was lowered to separate the layers, the water layer was separated, the oil layer was washed with water until neutral, and the solvent was evaporated to constant weight under reduced pressure to obtain 6.2 g of piperonal, with a yield of 84%.

Embodiment 3

[0019] In a three-necked flask, add 1.7g of water, 11g of glyoxylic acid, and 11g of sulfuric acid under stirring, cool down to 0-5°C, slowly add 6g of piperonylcycline dropwise, and keep it warm for 8 hours, dilute with 100mL of water, and filter with suction. Obtain 3,4-dimethoxymandelic acid and dilute sulfuric acid mother liquor;

[0020] In a three-necked flask, add 30% dilute sulfuric acid mother liquor, 3,4-dimethoxymandelic acid and 80 mL of dichloromethane, add 20 mL of 3% dilute nitric acid dropwise at 20°C, after the addition is complete, heat up to 40°C, React for 3 hours, lower the temperature, separate the layers, remove the water layer, wash the oil layer with water until neutral, and evaporate the solvent to constant weight under reduced pressure to obtain 6.4 g of piperonal, with a yield of 87%.

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PUM

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Abstract

The invention relates to a preparation method of piperonal. The specific steps are: mix water, glyoxylic acid and sulfuric acid in proportion, add piperonyl cyclocyclone dropwise at a temperature of 0-5°C, stir at a high speed for 5-8 hours, add After diluting with 80-100ml of water, filter with suction to obtain solid 3,4-dimethoxymandelic acid, and the filtrate is the mother liquor containing dilute sulfuric acid; the mass ratio of water, glyoxylic acid, and sulfuric acid is 1.5-1.7:10- 11:10‑11; take 30%‑70% dilute sulfuric acid mother liquor, add solid 3,4‑dimethoxymandelic acid to it, then add 80 mL of dichloromethane, add 3% dilute nitric acid 18‑1 dropwise at 20°C 20mL, heated, and reacted for 1-3 hours until the reaction was complete; layers were separated, washed, concentrated and distilled under reduced pressure to obtain the product piperonal.

Description

technical field [0001] The invention relates to a preparation method of piperonal, which belongs to the field of medicine and chemical industry. Background technique [0002] Piperonal, also known as jasmonal, is widely used in various daily cosmetic flavors and food flavors, and is also widely used in medicine, pesticides, electroplating and other industries. [0003] The existing synthetic technology of piperonal usually uses sulfuric acid, hydrochloric acid, phosphoric acid, nitric acid etc. as decarboxylation agent, wherein, phosphoric acid is done decarboxylation agent, even if heated for a long time, decarboxylation efficiency is also very low; Use hydrochloric acid to do decarboxylation agent, require concentration higher, but High-concentration hydrochloric acid is highly volatile and inconvenient for large-scale production; high-concentration sulfuric acid has a better decarboxylation effect, but it is prone to carbonization and darker dyed fabrics; as a decarboxyla...

Claims

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Application Information

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IPC IPC(8): C07D317/54
CPCC07D317/54
Inventor 徐兵夏铁红夏铁平夏荣良符庆强陈国勇夏治海
Owner 江西科美香料有限公司
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