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Method for producing hydratropic aldehyde

A production method, the technology of solanum aldehyde, applied in the production field of solanum aldehyde, can solve the problems of unfavorable industrial production, instability of peracetic acid, harsh reaction conditions, etc., and achieve the effect of low cost, few reaction steps and mild reaction

Inactive Publication Date: 2011-11-23
ZHEJIANG XINHUA CHEM
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Rivero et al. (Rivero I.A.Org.Prep.Proced.Int., 1993,24,363) proposed to prepare solanaldehyde by oxidation of 2-methylphenylethanol. Although the yield is high, the reaction conditions are harsh and the raw materials are special , not conducive to industrial production
Chen Wanzhi etc. (Chen Wanzhi, Chemical Journal of Universities, 1993,14,1265) utilize various rhodium chelates as catalyst to prepare Solanum aldehyde by hydroformylation of styrene, which is a new synthetic method, but the cost is higher
Guo Tingqiao et al. (Guo Tingqiao, Fine Chemical Industry, 2001, 18, 34) etc. used α-methylstyrene as raw material and peracetic acid as epoxidation reagent to prepare 2-phenylpropylene oxide. Solanum aldehyde is constructed. This method has the advantages of few steps, cheap raw materials, low cost, and high yield. However, peracetic acid is unstable, easy to decompose, and difficult to store, so it is not an ideal oxidant.
Shi Zhen et al. (Shi Zhen, Chemical Journal of Chinese Universities, 2001, 22, 1352) added benzimidazolidine salt and α-phenylethylmagnesium bromide to generate benzimidazolidine intermediate, and then hydrolyzed it under acidic conditions. Solanum aldehyde can be obtained. This method has the advantages of high yield, good product purity, and easy operation. However, this method is only in the laboratory research stage, and a large amount of research work needs to be carried out if it is really applied to actual production.

Method used

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  • Method for producing hydratropic aldehyde
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  • Method for producing hydratropic aldehyde

Examples

Experimental program
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Effect test

Embodiment 1

[0022] In a 2L three-necked flask equipped with a thermometer, stirring, dropping funnel and condensation column, add 800g of toluene, 180g of α-methylstyrene, and 650g of sodium percarbonate, stir vigorously, raise the temperature to 55°C, and slowly drop in acetic anhydride 300g, continue the reflux reaction after the dropwise addition, follow the reaction by chromatography, until the complete conversion of α-methylstyrene, the reaction time is about 25 to 30 hours, filter off the solid inorganic matter, wash to remove the residual peroxide, and recover the solvent Rectifying to obtain 2-phenylpropylene oxide with a content of ≥98%, and the yield is 90-95%.

[0023] In a 500ml three-neck flask equipped with a thermometer, stirring, dropping funnel, and condensation column, add 200g of toluene, stir and raise the temperature to 130°C, and slowly add 120g of the above-prepared 2-phenylpropylene oxide dropwise. Continue the reflux reaction, follow the reaction by chromatography...

Embodiment 2

[0025] In a 2L three-neck flask equipped with a thermometer, stirring, dropping funnel, and condensation column, add 1000 g of dichloromethane, 140 g of α-methylstyrene, 600 g of sodium percarbonate, and 8 g of triethylbenzyl ammonium chloride. Stir, raise the temperature to 45°C, slowly add 200g of acetic anhydride dropwise, continue the reflux reaction after the dropwise addition, follow the reaction by chromatography, until the complete conversion of α-methylstyrene, the reaction time is about 18 to 22 hours, filter off the solid inorganic matter, Washing with water to remove the residual peroxide, recovering the solvent and rectifying to obtain 2-phenylpropylene oxide with a content of ≥98% and a yield of 85-90%.

[0026] In a 500ml three-neck flask equipped with a thermometer, stirring, dropping funnel and condensation column, add 200g of benzene and 2g of zinc chloride, stir and raise the temperature to 60°C, and slowly drop in 140g of the above-prepared 2-phenylpropylene...

Embodiment 3

[0028] In a 500ml three-neck flask equipped with a thermometer, stirring, dropping funnel, and condensation column, add 200g of benzene, 40g of α-methylstyrene, 150g of sodium percarbonate, and 6g of polyethylene glycol 600, stir vigorously, and heat up to 42°C , slowly drop 60g of acetic anhydride, continue to reflux reaction after the dropwise addition, follow the reaction by chromatography, until the complete conversion of α-methylstyrene, the reaction time is about 15 to 20 hours, filter off the solid inorganic matter, wash with water to remove the residual excess Oxides, recovering the solvent and rectifying to obtain 2-phenylpropylene oxide with a content of ≥98%, and the yield is 90-95%.

[0029] In a 500ml three-neck flask equipped with a thermometer, stirring, dropping funnel and condensation column, add 200g of benzene, 2g of zinc bromide, stir and raise the temperature to 80°C, and slowly drop in 140g of the above-prepared 2-phenylpropylene oxide , continue the refl...

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Abstract

The invention discloses a process for producing an organically synthetic spice, in particular relates to a process for producing hydratropic aldehyde serving as an organic spice, and belongs to the technical field of chemical engineering. The process comprises the following steps of: performing epoxidation on alpha-methyl styrene serving as a raw material by taking peroxides such as sodium percarbonate and the like as epoxidation reagents in the presence of acetic anhydride, a solvent and a phase transfer catalyst to obtain 2-phenylpropylene oxide; and performing isomerization reaction on the prepared 2-phenylpropylene oxide in the presence of a catalyst and a solvent to obtain the hydratropic aldehyde. The invention provides a simple and convenient method for synthesizing the hydratropic aldehyde and has the advantages of low cost, mild reaction, a few reaction steps, safe and simple operation, high yield, high product purity, good industrial prospect and the like.

Description

technical field [0001] The invention relates to a method for producing organically synthesized perfume, in particular to a method for producing solanaldehyde as an organic perfume; it belongs to the technical field of chemical industry. technical background [0002] The chemical name of Solanum aldehyde is 2-phenylpropionaldehyde, the English name is: Hydratropic aldehyde or 2-Phenylpropionalaldehyde, the CAS registration number is [93-53-8], and the chemical structural formula is: [0003] [0004] Solanal is a precious spice and an important chemical raw material, widely used in spices, medicine, fuel and pesticide industries. During the industrial production method of Solanum aldehyde, acetophenone and ethyl monochloroacetate are used as raw materials and synthesized according to the Darzens method. Acetophenone and ethyl monochloroacetate are prepared under the action of a strong base to produce methyl phenyl glycidic acid ester. The ester is saponified, neutralized,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/228C07C45/58
Inventor 刘承伟王卫明应登宇谢自强兰昭洪陈宏
Owner ZHEJIANG XINHUA CHEM
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