Method for preparing 4-hexene-3-ketone by carrying out dehydration on 4-hydroxy-3-hexanone

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

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

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Problems solved by technology

[0007] The technical problem to be solved by the present invention is the problems o...

Method used

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  • Method for preparing 4-hexene-3-ketone by carrying out dehydration on 4-hydroxy-3-hexanone
  • Method for preparing 4-hexene-3-ketone by carrying out dehydration on 4-hydroxy-3-hexanone
  • Method for preparing 4-hexene-3-ketone by carrying out dehydration on 4-hydroxy-3-hexanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] By 1SiO 2 : 0.01Al 2 O 3 : 0.41TEAOH: 0.31 Acetylacetone: 31.76H 2 O Weigh each material, dissolve sodium aluminate in distilled water, add tetraethylammonium hydroxide dropwise, stir for 1 hour, add ethyl orthosilicate dropwise, stir for 1 hour, add acetylacetone, stir for 1 hour , adjust pH=13.0 with 0.1N sodium hydroxide solution, and continue stirring for 5 hours. The obtained mixture was crystallized under hydrothermal conditions at 170° C. for 4 days, washed, filtered and dried. The obtained product had characteristic diffraction peaks of ZSM-5 and preferentially grew in the (010) direction (b-axis). XRD spectrum see figure 2 In curve 1, the relative intensities of (020), (040), (060) and (080) peaks in the diffraction spectrum are significantly increased, which is obviously due to the preferred orientation of ZSM-5 single crystal on the powder diffraction sample plate, its (0h0) The surface, that is, the cylindrical surface of the single crystal, is paralle...

Embodiment 2

[0023] By 1SiO 2 : 0.01Al 2 O 3 : 0.25TPAOH: 0.05 Sodium oxalate: 32.0H 2 O Weigh each material, dissolve sodium aluminate in distilled water, add tetrapropylammonium hydroxide dropwise, stir for 1 hour, add silica sol dropwise, stir for 1 hour, add sodium oxalate, stir for 1 hour, use 0.1 N sodium hydroxide solution was adjusted to pH=12.0 and stirring was continued for an additional 5 hours. The resulting mixture was crystallized under hydrothermal conditions at 200°C for 3 days, washed, filtered and dried. XRD spectrum see figure 2 Middle curve 2. The synthesized ZSM-5 zeolite raw powder was treated with 0.8 mol / L acetic acid at 70° C. for 5 hours for 4 consecutive times, wherein the weight ratio of the acid solution and the ZSM-5 zeolite was 9 to obtain HZSM-5, that is, the catalyst.

[0024] The performance of the catalyst was evaluated according to the steps of [Example 1]. The reaction conditions and reaction results are shown in Table 1.

Embodiment 3

[0026] By 1SiO 2: 0.02Al 2 O 3 : 0.23TEAOH: 0.278-hydroxyquinoline: 44.64H 2 O Weigh each material, dissolve aluminum triethoxide in distilled water, add tetraethylammonium hydroxide dropwise, stir for 1 hour, add silica sol dropwise, stir for 1 hour, add 8-hydroxyquinoline, stir for 1 hour , adjust pH=11.0 with 0.1N sodium hydroxide solution, and continue stirring for 5 hours. The resulting mixture was crystallized under hydrothermal conditions at 150°C for 6 days, washed, filtered and dried. XRD spectrum see figure 2 Middle curve 3. The synthesized ZSM-5 zeolite raw powder was treated with 0.8 mol / L acetic acid at 80° C. for 5 hours for 3 consecutive times, wherein the weight ratio of the acid solution and the ZSM-5 zeolite was 8, to obtain HZSM-5, that is, the catalyst.

[0027] The performance of the catalyst was evaluated according to the steps of [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 carrying out dehydration on 4-hydroxy-3-hexanone, mainly aiming at solving the problems of low catalyst activity, high reaction temperature and slow space velocity in the prior art. The catalyst used by the method is prepared by the following steps of: mixing a silicon source, an aluminium source, template agent R1, template agent R2 and water, and adjusting the pH of the reaction mixture to be 8-14 with inorganic base; in the reaction mixture, controlling the molar ratio between Al2O3 and SiO2 to be 0.003-0.05, controlling the molar ratio of R1 to SiO2 to be 0.1-2, controlling the molar ratio of H2O to SiO2 to be 10-100 and controlling the molar ratio of R2 to SiO2 to be 0.05-2; and carrying out hydrothermal crystallization on the mixture for 1-10 days at the temperature of 100-250 DEG C to obtain the catalyst, wherein R1 comprises at least one selected from tetramethyl ammonium hydroxide, tetraethyl ammonium hydroxide, tetrapropyl ammonium hydroxide or tetrabutyl ammonium hydroxide, and R2 comprises at least one selected from beta-diketone, beta-diketone salt, oxalic acid, oxalate, catechol or 8-hydroxyquinoline. The technical scheme better solves the problems, and can be used in 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 preparing 4-hexen-3-one by dehydration of 4-hydroxy-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 in the preparation of food flavors such as Laomu, butter, horseradish, etc., 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 the 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 + ) combine to form an oxonium ion, which becomes a strong electron withdrawing group due to the positive charge on the oxygen atom, which makes the C-O bond easy to dissociate. The entire dehydration reaction involves the formation of protonated oxonium salts (R-OH 2 + ), the oxonium salt ...

Claims

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Application Information

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