Method for preparing lilial key intermediate namely tert-butylphenol-alpha-methylbenzene acrolein

A technology of methacrolein and p-tert-butyl, which is applied in the field of preparation of p-tert-butyl-α-methylphenylacrolein, the key intermediate of lilial, can solve the problem of difficult to realize large-scale industrial production and increase industrialization Problems such as manufacturing cost and low conversion rate of TBB can achieve the effect of easy realization of industrial production, avoiding reaction hot spots and improving conversion rate

Active Publication Date: 2018-10-16
SUQIAN COSMOS CHEM
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  • Summary
  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

The method reported in the prior art has the problems of low conversion rate of TBB, or poor selectivity and low yield of DHL, which increases the cost of industrialized manufacturing, produces more by-products and pollutes the environment
Green chem.2005, 7, 224-229 introduced the synthesis of DHL with ionic liquid as a solvent and piperidine as a catalyst. The conversion rate of raw material TBB is as high as 99%, but the selectivity of DHL is only 84%
Moreover, this method is difficult to achieve industrial scale production due to the use of expensive ionic liquids as solvents

Method used

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  • Method for preparing lilial key intermediate namely tert-butylphenol-alpha-methylbenzene acrolein
  • Method for preparing lilial key intermediate namely tert-butylphenol-alpha-methylbenzene acrolein
  • Method for preparing lilial key intermediate namely tert-butylphenol-alpha-methylbenzene acrolein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Under nitrogen protection, add 47kg of propionaldehyde and 70.5kg of anhydrous methanol into a dry and clean batching kettle, stir and mix at room temperature to obtain 117.5kg of propionaldehyde methanol solution, which is ready for use.

[0051] Main reaction stage:

[0052] Under the protection of nitrogen, add 110.5kg of p-tert-butylbenzaldehyde (TBB), 75kg of anhydrous methanol and 3kg of potassium hydroxide into a dry and clean condensation kettle, start stirring, control the temperature of the kettle at 20°C, and add 99kg of Prepared propionaldehyde methanol solution. During the dropwise addition process, the temperature of the kettle was always controlled at 20°C, and crystal DHL was gradually precipitated as the reaction progressed. After the dropwise addition was completed, the reaction was incubated for 1 h.

[0053] Reaction finishes, and 3.2kg acetic acid is added dropwise, to neutralize catalyst potassium hydroxide. Sampling, GC results: TBB 9.55%, DHL ...

Embodiment 2

[0059] Reaction condition is identical with embodiment 1, difference only is: increase propionaldehyde total amount, make the mol ratio of main reaction stage propionaldehyde and TBB be 1.05: 1;

Embodiment 3

[0061] Reaction condition is identical with embodiment 1, difference only is: increase propionaldehyde total amount, make the mol ratio of main reaction stage propionaldehyde and TBB be 1.10: 1;

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Abstract

The invention discloses a method for preparing a lilial key intermediate namely tert-butylphenol-alpha-methylbenzene acrolein. The method includes: at a set low temperature, adding propionaldehyde into p-tertbutyl benzaldehyde solution, and performing reaction under the catalytic action of potassium hydroxide; after reaction is finished, filtering to obtain a solid product namely tert-butylphenol-alpha-methylbenzene acrolein. By propionaldehyde dilution, low-temperature reaction crystallization, two-stage condensation reaction and the like, current situations including low raw material conversion rate, low yield and low purity in application of a tert-butylphenol-alpha-methylbenzene acrolein synthesis process are changed fundamentally, and the problem of low lilial quality is solved. The method has advantages of simplicity in operation, easiness in control and convenience in industrial production.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a preparation method of p-tert-butyl-alpha-methylphenylacrylaldehyde, a key intermediate of lilial. Background technique [0002] Lilial is one of the most productive varieties of synthetic fragrances. It is liquid under normal conditions and has a boiling point of 279°C. It has floral fragrances such as lily of the valley, lily lilac, and rabbit ear grass. Its aroma is pure, soft and elegant, and is deeply loved by perfumers. teacher welcome. Lilial is widely used in medium and high-grade cosmetic essences and soap essences, and is usually used in the deployment of lily of the valley, jasmine, oriental and floral essences. Lilial plays an irreplaceable role in the application of flavors and fragrances, and plays a decisive role in the deployment of flavors. Lilial is the main synthetic raw material for the production of fenpropimorph, fenpropidin and other pesticides. Due to the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/74C07C47/232
CPCC07C45/74C07C47/232
Inventor 刘启发王中孝钟世强
Owner SUQIAN COSMOS CHEM
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