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Method for preparing 4-hexene-3-ketone by 4-hydroxy-3-hexanone hydration

A technology of hexanone and hydroxyl, applied in the field of producing 4-hexen-3-one, which can solve the problems of poor catalyst activity, high reaction temperature, and low space velocity

Inactive Publication Date: 2013-04-10
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The technical problem to be solved by the present invention is that there are problems of high reaction temperature, low space velocity and poor catalyst activity in the prior art, and a new method for producing 4-hexen-3-one by dehydration of 4-hydroxyl-3-hexanone is provided. Methods

Method used

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  • Method for preparing 4-hexene-3-ketone by 4-hydroxy-3-hexanone hydration
  • Method for preparing 4-hexene-3-ketone by 4-hydroxy-3-hexanone hydration

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] by SiO 2 : Al 2 o 3 :OH - :Cl - :H 2 O=1:0.017:0.2:0.1:30. Weigh each material, dissolve sodium aluminate in distilled water, add dropwise silica sol, stir for 1 hour, add dropwise sodium chloride aqueous solution, stir for 1 hour, add dropwise sodium hydroxide aqueous solution, and continue stirring for 5 hours. The resulting mixture was crystallized under hydrothermal conditions at 100°C for 10 hours, then crystallized under hydrothermal conditions at 170°C for 24 hours, washed, filtered and dried, then exchanged with ammonium, dried and calcined to obtain the catalyst. XRD spectrum see figure 1 , SEM photo see figure 2 .

[0019] The performance evaluation of the catalyst was carried out on a fixed-bed reaction device at normal pressure. A stainless steel reactor with an inner diameter of 10 mm was used. The loading amount of the catalyst was 10 ml, the reaction temperature was 350 °C, and the liquid space velocity was 1 hour. -1 , reacted under normal pres...

Embodiment 2

[0021] by SiO 2 : Al 2 o 3 :OH - :Cl - :H 2 O=1:0.01:0.25:0.2:41. Weigh each material, dissolve aluminum sulfate in distilled water, add dropwise silica sol, stir for 1 hour, add dropwise potassium chloride aqueous solution, stir for 1 hour, add dropwise potassium hydroxide aqueous solution, and continue stirring for 5 hours. The resulting mixture was crystallized under hydrothermal conditions of 90°C for 12 hours, and then crystallized under hydrothermal conditions of 180°C for 40 hours, washed, filtered, dried, exchanged with ammonium, dried, and roasted to obtain the catalyst. The grain size was 2.1 microns.

[0022] Catalyst performance evaluation is the same as [Example 1]. The reaction conditions and reaction results are shown in Table 1.

Embodiment 3

[0024] by SiO 2 : Al 2 o 3 :OH - :Cl - :H 2 O=1:0.03:0.28:0.4:60. Weigh each material, dissolve aluminum nitrate in distilled water, add dropwise silica sol, stir for 1 hour, add dropwise potassium chloride aqueous solution, stir for 1 hour, add dropwise potassium hydroxide aqueous solution, and continue stirring for 5 hours. The resulting mixture was crystallized under hydrothermal conditions of 80°C for 12 hours, and then crystallized under hydrothermal conditions of 150°C for 50 hours, washed, filtered and dried, then exchanged with ammonium, dried and calcined to obtain the catalyst. The grain size is 1.8 microns.

[0025] Catalyst performance evaluation is the same as [Example 1]. The reaction conditions and reaction results are shown in Table 1.

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Abstract

The invention relates to a method for preparing 4-hexene-3-ketone by 4-hydroxy-3-hexanone hydration, which mainly solves the problems of low activity of a catalyst, high reaction temperature, and low space velocity in the prior art. Aiming at well solving the problems, the method adopts the technical scheme that the 4-hydroxy-3-hexanone is used as a raw material, and the reaction raw material comes into contact with an ZSM-5 catalyst to generate the 4-hexene-3-ketone when the reaction temperature is 200 to 400 DEG C and the liquid weight hourly space velocity is 0.5 to 15 h<-1> relative to the 4-hydroxy-3-hexanone; and the ZSM-5 catalyst is prepared by the following method of mixing a silicon source, an aluminum source, an alkaline source, a salt source and water, wherein the reaction mixture has a molar ratio of SiO2:Al2O3:OH<->:Cl<->:H2O=1:0.0025-0.05:0.1-0.6:0.05-0.5:20-200; crystallizing the mixture for 2 to 24 hours at the temperature of 60 to 120 DEG C, and crystallizing for 2 to 72 h at the temperature of 140 to 200 DEG C; and carrying out separating, washing, drying, ammonium exchange and sintering on the product, so as to obtain the catalyst. The method can be used for the industrial production of the 4-hexene-3-ketone prepared by the 4-hydroxy-3-hexanone.

Description

technical field [0001] The invention relates to a method for producing 4-hexen-3-one by dehydration of 4-hydroxyl-3-hexanone. Background technique [0002] 4-Hexen-3-one (CAS: 2497-21-4) is a unique spice (China GB 2760-2007), which is mainly used to prepare food flavors such as Laomu, butter, and horseradish, and has a wide range of uses. [0003] The dehydration reaction of hydroxyl compounds is a reaction in which the hydroxyl and hydrogen atoms on two adjacent atoms in the reactant molecule are removed in the form of water in the presence of a catalyst. Since the oxygen atom of the hydroxyl group contains a lone pair of electrons, it can interact with the proton (H + ) to form oxonium ions, which become strong electron-withdrawing groups due to the positive charges on the oxygen atoms, making the C-O bond easy to dissociate. The whole dehydration reaction includes: generating protonated oxonium salt (R-OH 2 + ), the oxonium salt slowly dissociates into a carbanion, a...

Claims

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Application Information

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IPC IPC(8): C07C49/203C07C45/66B01J29/40
Inventor 李亚男金照生
Owner CHINA PETROLEUM & CHEM CORP
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