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Preparation method of muscone

A technology of musk ketone and ketal is applied in the field of preparation of musk ketone, which can solve the problems of complicated preparation process, high cost, limitation of industrial mass production of musk ketone, etc., and achieve the effects of simple process and low cost.

Active Publication Date: 2018-01-19
江西凡生实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing method for preparing muscone has complicated process, high cost and cumbersome preparation process, which limits the industrial mass production of muscone

Method used

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  • Preparation method of muscone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] see figure 1 , a preparation method of muscone, wherein, comprises the steps:

[0028] (1) Preparation of the first ketal compound attached to the polystyrene resin:

[0029] In a 50L glass reactor equipped with a thermometer, a mechanical stirrer, and a water separator, add 2kg of polystyrene resin-loaded 1,2-diol (I), the second preset mass (1.28kg or 1.38kg) of 3 -Methyldiketene (II), 20L of toluene and the first catalyst of the third preset mass (4.4g or 7.3g), stirring and heating to 40°C-140°C, and reacting for the first preset time (2~20h ) and cooled to room temperature, filtered to obtain the first ketal compound loaded on polystyrene resin, wherein the first ketal compound is 2,6-dimethyl-octadeca-2,17-diene-8- Ketal or 9-methylheptadeca-1,16-diene-7-ketal.

[0030] Among them, the structural characteristics of the 1,2-diol (k is an integer from 4 to 18) carried by the polystyrene resin are:

[0031]

[0032] The chain length of the 1,2-diol and polysty...

Embodiment 2

[0047] (1) Preparation of 2,6-dimethyl-octadeca-2,17-diene-8-ketal supported on polystyrene resin (shown below, k=9):

[0048]

[0049] In a 50L glass reactor equipped with a thermometer, a mechanical stirrer and a water separator, add 2kg of 1,2-diol and 1.28kg of 2,6-diol with a degree of substitution of 0.73mol / kg polystyrene resin Methyl-octadec-2,17-dien-8-one, 20 L of toluene and 7.3 g of pyridinium p-toluenesulfonate. Heating to reflux and separating water for 10h under stirring conditions. After being cooled to room temperature, filter, and the filtrate obtained by filtering is used mechanically in the next reaction, and the polystyrene resin is washed 3 times with dichloromethane (10 liters each time), and is used in the next step.

[0050] (2) Preparation of 3-methylcyclopenta-6-ene ketal attached to polystyrene resin:

[0051]

[0052] In a 50L glass reactor equipped with a thermometer, mechanical stirring and a reflux condenser, add the 2,6-dimethyl-octadec...

Embodiment 3

[0060] (1) Resin preparation of 9-methylheptadeca-1,16-diene-7-ketal attached to polystyrene resin (as shown below, k=13):

[0061]

[0062] In a 50L glass reactor equipped with a thermometer, a mechanical stirrer and a water separator, add 2kg of 1,2-diol carried by polystyrene resin with a degree of substitution of 0.87mol / kg, 1.38kg of 9-methyl Heptadeca-1, 16-dien-7-one, 20 L of toluene and 4.4 g of pyridinium p-toluenesulfonate were heated under reflux to separate water for 15 hours while stirring. Filter after cooling to room temperature, and use the filtrate obtained by the filtration for the next reaction. The polystyrene resin is washed 3 times with dichloromethane (10 liters each time), and it will be used in the next step.

[0063] (2) Preparation of 3-methylcyclopenta-9-ene ketal attached to polystyrene resin:

[0064]

[0065] In a 50L glass reactor equipped with a thermometer, mechanical stirring and a reflux condenser, add the 9-methylheptadeca-1,16-diene...

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Abstract

The invention relates to a preparation method of muscone, which includes the steps of: 1) adding 1,2-diol supported on polystyrene resin, 3-methyl dienone, methylbenzene and pyridinium p-toluenesulfonate, stirring and heating the materials, cooling the materials to room temperature, and filtering the materials to produce a first ketal compound; 2) adding a first solvent and a catalyst, performingheating reflux until the reaction is finished, cooling a reaction product to room temperature and filtering the reaction product to produce a second ketal compound; 3) adding a first solvent and an acid solution, stirring the mixture until the reaction is finished, cooling a reaction product to room temperature, washing the reaction product to separate a first organic layer, and performing normalpressure recovery to the solvent in the first organic layer to collect a first ketene compound; 4) adding an alcohol solution and a metal catalyst into a reaction bottle, repeatedly replacing gas in the reaction bottle with N2 and H2, and performing a reaction at normal temperature and under normal pressure, and when the reaction is finished, performing filtration and pressure reduced rectification to obtain the muscone. The preparation method is simple in technical process and low in cost, and allows industrial large-scale production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of muscone. Background technique [0002] Muscone (3-methylcyclopentadione) is an important fragrance, which mainly exists in natural musk. Natural musk is the dry secretion in the male sac of musk deer, musk deer or musk deer. The source is very rare, so the natural muskone in it is even rarer. Therefore, chemists have been working on finding efficient and low-cost preparation methods. [0003] At present, the synthetic methods of muscone mainly include the ring expansion method of cyclic ketone and the ring closure method. Specifically, (1) cyclic ketone ring expansion method: since cyclododecanone is a cheap and easy-to-obtain by-product of the petroleum industry, it was first used as a raw material for the ring expansion method by Firmenich Laboratory. After decades of development, the ring expansion method has been able to simplify and shor...

Claims

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Application Information

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IPC IPC(8): C07C45/62C07C49/385C08F8/48C08F12/08
Inventor 方国华
Owner 江西凡生实业有限公司
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