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Continuous preparation method of DL-muscone

A technology of muskone and continuous chromatography, which is applied in the field of continuous preparation of DL-musketone, can solve the problems of low reactor capacity, difficulty in low-cost production, and large amount of solvent usage, and achieve high process stability, continuous production, and high-quality products. The effect of high yield

Active Publication Date: 2018-06-22
INST OF CHEM ENG GUANGDONG ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In summary, the existing process route for synthesizing DL-muskone from hexadecanedione still has disadvantages such as low yield, excessive solvent usage, and low reactor capacity, making it difficult to achieve large-scale and low-cost production. Production

Method used

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  • Continuous preparation method of DL-muscone

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preparation example Construction

[0026] A continuous preparation method of DL-Muscone, comprising the following steps:

[0027] 1) Dissolve 2,15-hexadecanedione III in an aprotic solvent, then react continuously in a fixed-bed cyclization reactor, and cyclize under the action of a cyclization catalyst to generate 3-methylcyclopentacene Ketone analog II;

[0028]

[0029] 2) After the 3-methylcyclopentacenone analog II is desolvated, it is dissolved in a protic solvent, and then reacted continuously with hydrogen in a fixed-bed hydrogenation reactor under the action of a hydrogenation catalyst to obtain the formula Muscone shown in Ι;

[0030]

[0031] 3) Precipitate the product obtained in step 2) and carry out continuous chromatographic separation, the product solution containing DL-musketone undergoes desolventization to obtain the DL-muscarone product, and the component containing 2,15-hexadecanedione is decolorized Return to step 1) for use after purification.

[0032] In the present invention, 2...

Embodiment l

[0046]2,15-hexadecanedione III is dissolved in dichloroethane (the weight ratio of dichloroethane to 2,15-hexadecanedione is 10:1), and then passed through a fixed-bed cyclization reactor continuous response. The ring closure catalyst is SiO 2 supported nano ZrO 2 , the weight hourly space velocity of 2,15-hexadecanedione on the catalyst is 0.01h -1 . The catalyst bed temperature is 300°C, and the vacuum degree is 0.06MPa.

[0047] Precipitate the 3-methylcyclopentacenone analog II obtained after cyclization, then dissolve it in absolute ethanol and react continuously with hydrogen in a fixed-bed hydrogenation reactor, ethanol and 3-methylcyclopentacenone The weight ratio of pentacenone is 10:1. The hydrogenation catalyst is palladium supported on activated carbon, the palladium load is 1%, and the weight hourly space velocity (calculated as 3-methylcyclopentacenone analogue) is 0.01h -1 . The reaction temperature is 90° C., and the hydrogen pressure is 3 MPa.

[0048]...

Embodiment 2

[0050] 2,15-hexadecanedione III was dissolved in chloroform (the weight ratio of chloroform to 2,15-hexadecanedione was 4:1), and then reacted continuously in a fixed-bed cyclization reactor. The ring closure catalyst is Al 2 o 3 supported nano ZrO 2 , the weight hourly space velocity of 2,15-hexadecanedione on the catalyst is 0.1h -1 . The catalyst bed temperature is 280°C, and the vacuum degree is 0.07MPa.

[0051] The 3-methylcyclopentacenone analog II obtained after cyclization is desolvated, then dissolved in anhydrous methanol and continuously reacted with hydrogen in a fixed-bed hydrogenation reactor, methanol and 3-methylcyclopentacenone The weight ratio of pentacenone analogs is 5:1. The hydrogenation catalyst is palladium supported on activated carbon, the palladium load is 2%, and the weight hourly space velocity (calculated as 3-methylcyclopentacenone analogue) is 0.2h -1 . The reaction temperature is 60° C., and the hydrogen pressure is 2.5 MPa.

[0052] T...

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Abstract

The invention discloses a continuous preparation method of DL-muscone. The preparation method comprises the following steps: 1) dissolving 2,15-hexadecanedione diketone in an aprotic solvent, then carrying out a continuous reaction in a fixed-bed cyclization reactor for generating a 3-methylcyclopentanone analogue under the action of a cyclization catalyst; 2) carrying out desolvation on the 3-methylcyclopentanone analogue, dissolving the obtained product in a protic solvent, then carrying out a continuous reaction with hydrogen in a fixed-bed hydrogenation reactor under the action of a hydrogenation catalyst to obtain muscone; and 3) carrying out desolvation on the product obtained in the step 2), carrying out continuous chromatographic separation, and carrying out desolvation on the product liquid containing the DL-muscone to obtain the DL-muscone product. The method for preparing the DL-muscone provided by the invention has high process stability and high product yield, continuous production of the DL-muscone can be realized, the production cost is greatly reduced, and the effective capacity of a device is improved.

Description

technical field [0001] The invention relates to a continuous preparation method of DL-muskone. Background technique [0002] DL-Muskone (chemical name 3-methylcyclopentadecone, CAS No. 541-91-3) is the main active ingredient of natural musk, with a content of about 0.1-2% in natural musk. Natural musk is a precious natural fragrance that can be obtained from the pollen and roots of animals such as male musk deer and civet cats and plants such as ambrette, and its natural sources are rare. The medicinal value of musk is even greater, and its pharmacology and efficacy have been listed as top grade in my country’s earliest medical classics, Shen Nong’s Herbal Classic, Er Ya, and Dong Yi Bao Jian, accounting for about 20% of Chinese Pharmacopoeia. Chinese patent medicines are equipped with musk. [0003] Natural musk resources are extremely limited and expensive (more than 400,000 yuan / kg), but the demand is strong, so the artificial synthesis of muskone has important social si...

Claims

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Application Information

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IPC IPC(8): C07C45/62C07C49/385C07C45/79
CPCC07B2200/07C07C45/62C07C45/66C07C45/79C07C49/385C07C49/587
Inventor 王飞麦裕良高敏杰戴永强张磊苏瑜
Owner INST OF CHEM ENG GUANGDONG ACAD OF SCI
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