Continuous preparation method of high-selectivity alpha-ionone

A technology of pseudo-ionone and ionone, applied in the field of fragrance chemistry and fine chemicals, can solve the problems of low production efficiency, high price of organic acid, high production cost, etc., and achieve the goal of improving production efficiency, high catalytic efficiency and cost Effect

Inactive Publication Date: 2020-07-28
SHANDONG NHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the organic acid is added in this scheme, there will be a part of the inorganic base catalyst to neutralize the condensation reaction. After the cyclization reaction, an alkali needs to be added to neutralize the organic acid. On the one hand, the price of the organic acid is high, and it cannot be applied mechanically, resulting in high production costs. The two acid-base neutralization reactions release a large amount of heat, which is not conducive to the control of the reaction temperature and produces a large amount of waste salt
[0007] At present, the industrial synthesis of α-ionone mainly uses about 85% phosphoric acid a

Method used

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  • Continuous preparation method of high-selectivity alpha-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 A continuous preparation method of highly selective α-ionone

[0044] Include the following steps:

[0045] The catalysts used include concentrated sulfuric acid and isovaleric acid, which are respectively marked as catalyst 1 and catalyst 2; the catalyst auxiliary agent used is benzyltriethylammonium chloride.

[0046] Weigh 36 kg of isovaleric acid and 3.6 kg of benzyltriethylammonium chloride, add them into a stirring tank and stir evenly; then slowly add 36 kg of concentrated sulfuric acid with a mass percentage of 85% to obtain a catalyst system.

[0047] The catalyst system is passed through the low-temperature tank to control the temperature of the kettle at -2°C-2°C (the low-temperature tank and the jacket of the stirred tank are connected by pipelines to form a loop), and the stirring is continued to prevent local overheating.

[0048] The solvent used was toluene.

[0049] Weigh 72 kg of industrial-grade toluene and 36 kg of pseudoionone, and add t...

Embodiment 2

[0060] Example 2 A continuous preparation method of highly selective α-ionone

[0061] Same as the preparation method of Example 1, only change the catalyst, auxiliary agent, solvent, material proportion and reaction conditions, carry out the preparation method of embodiment 2-6; The catalyst, auxiliary agent, solvent, material used in embodiment 1-6 The proportioning ratio is shown in Table 1, and the reaction conditions used in Examples 1-6 are specifically shown in Table 2; the ionone finished product obtained after the reaction of Examples 1-6 is detected by gas chromatography, and the α-ionone of the reaction product is obtained. content, post-processing to obtain the total ketone yield, specifically as shown in Table 3;

[0062] Table 1 Embodiment 1-6 reaction material composition and material proportion

[0063]

[0064] The reaction condition of table 2 embodiment 1-6

[0065]

[0066] Table 3 The α-ionone content and total ketone yield of the reaction product ...

Embodiment 7

[0069] Example 7 A continuous preparation method of highly selective α-ionone

[0070] (1) Preparing the catalyst system

[0071] The catalysts used include methanesulfonic acid and isovaleric acid, which are respectively marked as catalyst 1 and catalyst 2; the catalyst auxiliary agent used is benzyltriethylammonium chloride; the solvent used is toluene. The mass percent content of the methanesulfonic acid is 99%.

[0072] Weigh 36 kg of isovaleric acid and 3.6 kg of benzyltriethylammonium chloride, add them into a stirring tank, and stir for 5 minutes at a stirring rate of 200 r / min. Then slowly add 36 kg of methanesulfonic acid with a mass percent content of 99% to obtain a catalyst system.

[0073] (2) Reaction material pretreatment

[0074] The catalyst system is passed through the low-temperature tank to control the temperature of the kettle at -2°C-2°C (the low-temperature tank and the jacket of the stirred tank are connected by pipelines to form a loop), and the sti...

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Abstract

The invention provides a continuous preparation method of high-selectivity alpha-ionone, pseudoionone is taken as a raw material, alpha-ionone is prepared under the condition of a catalyst system, thecatalyst system comprises a catalyst 1, a catalyst 2 and an auxiliary agent, the catalyst 1 is concentrated sulfuric acid or methanesulfonic acid, and the catalyst 2 is liquid organic carboxylic acid. Pseudoionone, a solvent and a catalyst system are uniformly mixed in a static mixer, then enter a pipeline reactor and react in the pipeline reactor, then the reaction liquid is discharged from an outlet of the pipeline reactor and enters a quenching stirring kettle to be quenched, and the reaction is ended. The synthesis process provided by the invention has the advantages of high catalytic efficiency, short reaction time, high alpha ionone content, continuous application of the catalyst and less three wastes, realizes continuous reaction, greatly saves the reaction time, operation and device cost, meets the requirements of green chemistry, and is suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of fragrance chemistry and fine chemicals, and in particular relates to a continuous preparation method of highly selective α-ionone. Background technique [0002] Ionone, chemical name: 4-(2,6,6-trimethyl-2-cycloocten-1-yl)-3-buten-2-one, is widely used in the perfume industry and pharmaceutical industry , it has two common isomers, namely α-ionone and β-ionone. Among them, α-ionone has a strong violet aroma and a little warm woody aroma. It is widely used in daily chemical toiletries and cosmetics, and is also used in a small amount in the food industry. And β-ionone is an important intermediate in the synthesis of vitamin A, mainly used in the pharmaceutical industry. [0003] Using pseudo-ionone as raw material and using acid as catalyst, this process was first proposed by Hibbert et al. in 1924. On this basis, after nearly a hundred years of research by generations of scientific and technological work...

Claims

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Application Information

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IPC IPC(8): C07C45/67C07C49/21C07C45/78B01J31/04
CPCB01J31/04B01J2231/52C07C45/67C07C45/78C07C2601/14C07C49/21
Inventor 刘正良马啸方万军李聪聪籍晓飞樊国涛谢坤
Owner SHANDONG NHU PHARMA
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