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Preparation method for vanillylamine hydrochloride

A technology of vanillin amine hydrochloride and composite catalyst, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of amino hydroxyl compounds, etc., can solve the problems of low yield, high risk, high investment, etc. High efficiency, low cost, good purity

Inactive Publication Date: 2017-02-01
HENAN CHEM IND RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Utilizing the method of the present invention to prepare vanillin amine hydrochloride can solve the problem of low yield in the direct reductive amination method of vanillin amine hydrochloride with ammonium formate in the prior art, high pressure reaction, high risk, and precious metal as catalyst Disadvantages such as higher investment

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  • Preparation method for vanillylamine hydrochloride
  • Preparation method for vanillylamine hydrochloride
  • Preparation method for vanillylamine hydrochloride

Examples

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Effect test

Embodiment 1

[0036] The preparation method of vanillin amine hydrochloride of the present invention, the detailed steps of this preparation method are as follows:

[0037] a. Using 3-methoxy-4-hydroxybenzaldehyde oxime as raw material and ethanol as solvent; first, add 133.6g (0.80mol) of 3-methoxy-4-hydroxybenzaldehyde oxime into a device equipped with a stirrer and a thermometer Then add 1400mL of ethanol and 13.0g of aluminum-zinc-nickel composite catalyst into a 2L three-necked flask, pass hydrogen under normal pressure for protection, heat up to 40°C, and react at this temperature for 8h;

[0038] b. Filtrate after the reaction (the obtained filter residue is unreacted composite catalyst, which is recovered and recycled), add 70mL of hydrochloric acid with a mass percentage concentration of 30% to the obtained filtrate, adjust the pH value of the filtrate to 1, and precipitate white crystals , filtered the separated white crystals, and obtained 136.8 g of vanillin amine hydrochloride ...

Embodiment 2

[0046] The preparation method of vanillin amine hydrochloride of the present invention, the detailed steps of this preparation method are as follows:

[0047]a. Using 3-methoxy-4-hydroxybenzaldehyde oxime as raw material and ethanol as solvent; first, add 133.6g (0.80mol) of 3-methoxy-4-hydroxybenzaldehyde oxime into a device equipped with a stirrer and a thermometer In a 2L three-necked flask, add 1400mL ethanol and 13.0g aluminum-zinc-nickel composite catalyst, pass hydrogen gas under normal pressure for protection, heat up to 50°C, and react at this temperature for 7h;

[0048] b. Filtrate after the reaction (the obtained filter residue is unreacted composite catalyst, which is recovered and recycled), add 70mL of hydrochloric acid with a mass percentage concentration of 30% to the obtained filtrate, adjust the pH value of the filtrate to 1, and precipitate white crystals , filtered the precipitated white crystals, and obtained 134.4 g of vanillinamine hydrochloride finishe...

Embodiment 3

[0056] The preparation method of vanillin amine hydrochloride of the present invention, the detailed steps of this preparation method are as follows:

[0057] a. Using 3-methoxy-4-hydroxybenzaldehyde oxime as raw material and ethanol as solvent; first, add 133.6g (0.80mol) of 3-methoxy-4-hydroxybenzaldehyde oxime into a device equipped with a stirrer and a thermometer In a 2L three-neck flask, add 1500mL ethanol and 20.0g aluminum-zinc-nickel composite catalyst, pass hydrogen gas under normal pressure for protection, heat up to 60°C, and react at this temperature for 6h;

[0058] b. Filtrate after the reaction (the obtained filter residue is unreacted composite catalyst, which is recovered and recycled), add 70mL of hydrochloric acid with a mass percentage concentration of 30% to the obtained filtrate, adjust the pH value of the filtrate to 1, and precipitate white crystals , filtered the separated white crystals, and obtained 132.1 g of vanillin amine hydrochloride finished p...

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Abstract

The invention discloses a preparation method for vanillylamine hydrochloride. The preparation method comprises the following steps: adding 3-methoxy-4-hydroxybenzaldehyde oxime into a reaction container, then adding alcohol and a composite catalyst, introducing hydrogen under a normal pressure condition for protection and carrying out heating for a reaction; and carrying out filtering after the reaction, adding hydrochloric acid with mass percentage concentration of 30% into a filtrate, adjusting the pH value of the filtrate to 1, filtering out a precipitated white crystal and carrying out vacuum drying so as to obtain finished vanillylamine hydrochloride. The method provided by the invention is simple in operation process, low in cost, high in yield, low in reaction conditions, high in product purity and environment-friendly. The method can overcome the disadvantages that a direct reduction and amination method for production of vanillylamine hydrochloride from ammonium formate has low yield, usage of a high-pressure reaction leads to great danger, usage of precious metals as catalysts results in high investment and the like in the prior art.

Description

[0001] 1. Technical field: [0002] The invention belongs to the technical field of fine organic synthesis, and in particular relates to a method for preparing vanillin amine hydrochloride by using an aluminum-zinc-nickel composite catalyst as a catalyst. [0003] 2. Background technology: [0004] The chemical name of vanillin amine hydrochloride is 3-methoxy-4-hydroxybenzylamine hydrochloride, which is a key intermediate for the synthesis of natural capsaicinoids and their analogs. Capsaicin has multiple uses; 1. Police riot control, capsaicin has a strong irritant, and personnel will experience severe eye pain, tearing, coughing, sneezing, chest pain and other symptoms after contact. Its vapor or fine powder is highly irritating to eyes and upper respiratory tract. And because of the characteristics of low stimulation valve, rapid onset and disappearance of symptoms, high safety ratio, and multiple ways of release, it has been widely used in police riot control; 2. It has a...

Claims

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Application Information

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IPC IPC(8): C07C213/02C07C217/58B01J23/80
CPCC07C213/02B01J21/02B01J23/06B01J23/755B01J23/80B01J35/19C07C217/58Y02P20/584
Inventor 刘菲于景民刘玉霞柴勇利赵胜勇崔炳春张辰李明王大陆
Owner HENAN CHEM IND RES INST
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