Method for preparing amyl cyclopentenone through organic solvent-free isomerization in methyl dihydrojasmonate synthesis

A technology of methyl dihydrojasmonate and pentylcyclopentenone, applied in the field of organic synthesis, can solve problems such as increased cost of hazardous waste treatment, unfavorable economic and environmental sustainable development, etc. Cost saving and moisture reduction effect

Inactive Publication Date: 2019-12-20
HUAIAN WAN BANG SPICE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Wherein strong acid isomerization reaction, the technology that adopts at present is to use xylene as solvent, take p-toluenesulfonic acid as acid catalyst, acetic anhydride as auxiliary catalyst, pentylene cyclopentanone isomerization generates pentyl cyclopentenone, in

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 2500kg of p-toluenesulfonic acid and 300kg of acetic anhydride into the reaction kettle, stir evenly, and heat to 120±2°C, stir for 5 minutes to stabilize, add 12.5kg of pentylene cyclopentanone dropwise at a rate of 1250kg / min, dropwise During the process, keep the reaction temperature at 118-122°C. After the dropwise addition, keep stirring at 118-122°C for 2-4 hours. After the reaction, cool down and adjust the pH of the reaction solution to 7.5- 9. Stand for stratification, remove the lower layer of water, the upper oil phase is the crude product of pentylcyclopentenone, go to rectification to obtain the finished product of pentylcyclopentenone, and obtain 2298g of the finished product of pentylcyclopentenone with a purity of 94.1 %, the yield is 86.5%.

Embodiment 2

[0020] Add 2500kg of p-toluenesulfonic acid and 250kg of acetic anhydride into the reaction kettle, stir evenly, and heat to 120±2°C, stir for 5 minutes to stabilize, add 10kg of pentylene cyclopentanone dropwise, the dropping speed is 1250kg / min, the dropping process During the process, keep the reaction temperature at 118-122°C. After the dropwise addition, keep stirring at 118-122°C for 2-4 hours. After the reaction, cool down and adjust the pH of the reaction solution to 7.5-9 with 10%-13% sodium carbonate solution. , stand for stratification, separate to the water in the lower layer, the upper oil phase is the crude product of pentylcyclopentenone, go to rectification to obtain the finished product of pentylcyclopentenone, and obtain 2329g of the finished product of pentylcyclopentenone with a purity of 93.6% , and the yield was 87.2%.

Embodiment 3

[0022] Add 2500kg of p-toluenesulfonic acid and 375kg of acetic anhydride into the reaction kettle, stir evenly, and heat to 120±2°C, stir for 5 minutes to stabilize, add 15kg of pentylene cyclopentanone dropwise, the dropping speed is 1250kg / min, the dropping process During the process, keep the reaction temperature at 118-122°C. After the dropwise addition, keep stirring at 118-122°C for 2-4 hours. After the reaction, cool down and adjust the pH of the reaction solution to 7.5-9 with 10%-13% sodium carbonate solution. , stand for stratification, separate to the lower layer of water, the upper oil phase is the crude product of pentylcyclopentenone, go to rectification to obtain the finished product of pentylcyclopentenone, and obtain 2294g of the finished product of pentylcyclopentenone with a purity of 94.5% , and the yield was 86.7%.

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Abstract

The invention discloses a method for preparing amyl cyclopentenone through organic solvent-free isomerization in methyl dihydrojasmonate synthesis. The method comprises: stirring and mixing p-toluenesulfonic acid and acetic anhydride in a reactor, heating to a temperature of 120 +/-2 DEG C while stirring, adding pentylidene cyclopentanone in a dropwise manner, carrying out thermal insulation stirring for 2-4 h at a temperature of 118-122 DEG C after the adding, cooling after the reaction is finished, regulating the pH value of the reaction solution to 7.5-9 by using a sodium carbonate solution, and carrying out standing layering to obtain an oil phase, wherein the oil phase is crude amyl cyclopentenone. According to the present invention, during the isomerization, no organic solvent is used so as to achieve clean and environmentally-friendly production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the synthesis of perfume compounds, in particular to a method for preparing amylcyclopentenone without organic solvent isomerization in the synthesis of methyl dihydrojasmonate. Background technique [0002] Jasmine fragrance compounds have been studied for decades, but with the increasing demand for such compounds, the progress of their industrialization has been far from meeting the needs. Methyl Dihydrojasmonate (MethylDihydrojasmonate, MDJ) belongs to jasmone compound, is one of the important jasmine spices of artificial synthesis, has not found the related report that it exists in natural spices up to now, because its price is relatively low, application It has a wide range, so it is an important spice variety in the modern spice industry. Its appearance is colorless or light yellow transparent liquid, its chemical properties are relatively stable, it has the advant...

Claims

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Application Information

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IPC IPC(8): C07C45/67C07C45/82C07C49/597
CPCC07C45/67C07C45/82C07C2601/10C07C49/597
Inventor 李向前孙学剑张坚赵成进李瀛张鹏飞
Owner HUAIAN WAN BANG SPICE IND CO LTD
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