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Synthesis process of beta-damascenone

A synthesis process, the technology of Turkone, applied in the field of industrial production of β-Turkone, can solve the problems of high cost, complicated operation, and difficulty in industrial production, and achieve low raw material cost, high product purity, and low energy consumption Effect

Pending Publication Date: 2020-02-04
新乡市博源生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although there have been many reports on the research on the synthesis of β-turkone, the existing methods have problems such as high cost and complicated operation, and it is difficult to realize industrial production
At present, the research on the industrial production of β-turkone is almost blank

Method used

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  • Synthesis process of beta-damascenone
  • Synthesis process of beta-damascenone
  • Synthesis process of beta-damascenone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Synthesis of Diene to Prepare 1-(2,6,6,-Trimethylcyclohex-3-enyl)-ethanone

[0022] Add dichloromethane (200L) and anhydrous aluminum trichloride (319Kg, 2400mol) in the reaction kettle, stir well, add dropwise the dichloromethane of 4-methyl-3-penten-2-one (294Kg, 3000mol) Methane solution (150L), stirred for 2h, passed into 1,3-pentadiene, continued to stir the reaction, GC monitored the reaction, stopped the reaction when the content of 4-methyl-3-penten-2-one was lower than 1% . Ice water (400 L) was added to quench the reaction, and the layers were separated. The organic phase was washed with saturated aqueous sodium chloride solution, dichloromethane was recovered by distillation, and the remaining organic phase was sent to a rectification kettle for rectification to obtain 1-(2,6,6,-trimethylcyclohex-3-enyl )-ethanone (358Kg, yield 72%).

Embodiment 2

[0024] Preparation of 1-(2,6,6,-trimethylcyclohex-1-enyl)-ethanone by isomerization of olefins

[0025] Will SO 4 2- / ZrO 2 Solid superacid catalyst (7.9Kg, 36mol) packs diameter 0.16 meters, in the gas-phase reactor of 5 meters in length, under nitrogen purge, gas-phase reactor is heated to 300 ℃, then depressurizes and makes gas-phase reactor internal pressure be 45mmHg, use a quantitative pump to introduce 1-(2,6,6,-trimethylcyclohex-3-enyl)-ethanone (60Kg, 360mol) into the gas phase reactor at a speed of 7.5Kg / h, Continue to maintain the reaction at 300-380°C. After the reaction is over, the reaction gas enters the cooling tower to cool, and the cooled mixture is sent to the rectification kettle for rectification to obtain 1-(2,6,6,-trimethylcyclohexane -1-enyl)-ethanone (51 Kg, 85% yield, 99% conversion, 95% purity). SO 4 2- / ZrO 2 The solid superacid catalyst continues to be recycled 6 times.

[0026] Table 1 The impact of catalyst recycling on conversion and yie...

Embodiment 3

[0029] Preparation of β-Turkone by Aldol Condensation

[0030]Add ethylmagnesium bromide tetrahydrofuran solution (1.0M, 1800L) into the reaction kettle, pass frozen brine into the cooling jacket of the reaction kettle, wait until the reaction kettle is cooled to 0°C, add N-methylaniline tetrahydrofuran dropwise The solution (128.5Kg, 1200mol, 500L) was stirred evenly at 0°C, and 1-(2,6,6,-trimethylcyclohex-1-enyl)-ethanone (166Kg, 1000mol) was added. The temperature of the reactor was raised to room temperature, and the stirring reaction was continued for 5 h. Slowly add tetrahydrofuran solution (39.6Kg, 900mol, 300L) of acetaldehyde, GC monitors reaction, when the content of 1-(2,6,6,-trimethylcyclohex-1-enyl)-ethanone is lower than 1 %, add 10% hydrochloric acid solution (1000L), continue to stir the reaction for 1h, and stop the reaction. The layers were separated, and the aqueous phase was extracted with ethyl acetate (1000 L×2). The organic phases were combined and was...

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Abstract

The invention belongs to the technical field of chemical synthesis of perfume essences and in particular relates to a novel synthesis process for industrial production of beta-damascenone. The synthesis process comprises the following steps: by taking 1,3-pentadiene as a starting material, performing a Diels-Alder addition reaction on the 1,3-pentadiene with 4-methyl-3-pentene-2-one under catalysis of AlCl3 firstly so as to generate 1-(2,6,6,-trimethyl cyclohexyl-3-alkenyl)-butanone; under the catalysis of a solid super strong acid catalyst, performing olefin isomerization so as to obtain 1-(2,6,6,-trimethyl cyclohexyl-1-alkenyl)-butanone; and finally, performing a hydroxyaldehyde condensation reaction with acetaldehyde, so as to generate a target product, namely beta-damascenone. The synthesis process provided by the invention has the main advantages that the raw material cost is low, the energy consumption is low, a gas-phase reaction catalyzed by the solid super strong acid catalystis implemented in an olefin isomerization production process, the product purity is high, no reaction solvent is needed, a very small amount of wastewater or waste gas is generated, and in addition,the catalyst is good in reuse performance.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis of fragrance essence, and in particular relates to a new synthesis process for industrial production of β-turkone. Background technique [0002] β-Turkone (β-Damascone, Formula 1), also known as β-Damascone, is a precious daily spice and can also be used as a food spice (Standards for the use of food additives, GB 2760-2014) . Firmenich of Switzerland isolated and extracted β-turkone from Bulgarian rose oil (Rosa damascena Mill.) for the first time, and found that it has attractive rose fragrance and sweet fruity fragrance. Scientists such as Demole realized the first synthesis of β-turkone from β-ring citral (Demole, E.; Enggist, P.; Saeuberli, U.; Stoll, M.; Kovats, E. Helv. Chim. Acta 1970, 53, 541.). [0003] [0004] β-Turkone has many advantages such as pure aroma, elegant fragrance type, long-lasting fragrance, non-toxic, etc. It is mainly used in high-end cosmetics, precio...

Claims

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Application Information

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IPC IPC(8): C07C45/74C07C49/557
CPCC07C45/74C07C45/67C07C45/69C07C2601/16C07C49/557C07C49/543
Inventor 郭兴永王锦华
Owner 新乡市博源生物科技有限公司
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