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A kind of preparation method of azoin compounds

The technology of a compound and acetoin is applied in the field of preparation of acetoin compounds, can solve the problems of unstable catalyst thiazole salt, influence the yield of acetoin and the like, and achieves the effects of easy control of reaction conditions, less impurities and less poisoning

Active Publication Date: 2019-06-11
濮阳天源生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The Chinese invention patent with application number 200910310247.2 uses paraldehyde as the raw material and thiazole salt as the catalyst to catalyze the synthesis of acetoin in a self-generating pressure reactor by the "one-pot cooking" method, but the reaction environment is alkaline, and the catalyst thiazole The salt is also unstable, thus affecting the yield of acetoin

Method used

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  • A kind of preparation method of azoin compounds
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  • A kind of preparation method of azoin compounds

Examples

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Effect test

Embodiment 1

[0023] A preparation method of acetoin compounds, the steps are: step 1: under stirring conditions, add aldehydes and catalysts with a weight ratio of (100-200): 1 to the reaction kettle, the aldehydes are acetaldehyde, propionaldehyde or Butyraldehyde, the reaction temperature is controlled at 70-120°C, the reaction pressure is 0.4-0.8MPa, the reaction time is 0.5-5h, and the reaction solution is obtained; Step 2: The reaction solution in step 1 is subjected to vacuum distillation, and the distillation temperature is collected at 80 The distillate between ~160°C is the azoin compound, and the atoin compound is acetoin, propioin or butyroin.

[0024] Above-mentioned catalyst is 1-n-butylbenzimidazole hydrochloride, and its structural formula is The preparation steps of the catalyst are as follows: put benzimidazole, chlorobutane and acetonitrile with a weight ratio of 1:(1~5):(2~20) in a three-necked flask, heat to reflux, the reflux temperature is 80°C, and reflux The time ...

Embodiment 2

[0027] (1) Preparation of catalyst

[0028] Get 36g of benzimidazole, 108g of chlorobutane and 360g of acetonitrile in a three-necked flask, the weight ratio of benzimidazole, chlorobutane and acetonitrile is 1:3:10, heat to reflux, and the reflux temperature is 100°C , Reflux 10h, obtain catalyst crude material, then catalyst crude material is through centrifugation, washing, drying the 1-n-butylbenzimidazole hydrochloride that obtains 143g, and its proton nuclear magnetic resonance spectrum is: 1 H NMR (CDCl 3 ):0.90(t,J=7.4Hz,3H),1.31(m,2H),1.74(m,2H),4.04(t,J=7.5Hz,2H),7.22(m,2H),7.59(m ,2H), 8.26(s,1H).

[0029] The reaction equation for preparing the catalyst is:

[0030]

[0031] (2) Preparation of Acetoin

[0032] Under stirring condition, add the acetaldehyde of 500g and the 1-n-butylbenzimidazole hydrochloride of 2.5g in reactor, the weight ratio of acetaldehyde and 1-n-butylbenzimidazole hydrochloride is 200: 1. The reaction temperature is controlled at 80°C...

Embodiment 3

[0036] (1) Preparation of catalyst

[0037] Get 36g of benzimidazole, 108g of chlorobutane and 360g of acetonitrile in a three-necked flask, the weight ratio of benzimidazole, chlorobutane and acetonitrile is 1:3:10, heat to reflux, and the reflux temperature is 100°C , Reflux 10h, obtain catalyst crude material, then catalyst crude material is through centrifugation, washing, drying the 1-n-butylbenzimidazole hydrochloride that obtains 143g, and its proton nuclear magnetic resonance spectrum is: 1 H NMR (CDCl 3 ):0.90(t,J=7.4Hz,3H),1.31(m,2H),1.74(m,2H),4.04(t,J=7.5Hz,2H),7.22(m,2H),7.59(m ,2H), 8.26(s,1H).

[0038] The reaction equation for preparing the catalyst is:

[0039]

[0040] (2) Preparation of Propionin

[0041] Under stirring condition, add the N-butylbenzimidazole hydrochloride of 500g propionaldehyde and 3.5g in the reactor, the weight ratio of propionaldehyde and 1-n-butylbenzimidazole hydrochloride is 143:1 , the reaction temperature is controlled at 1...

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Abstract

The invention relates to a preparation method of acyloin compounds, and belongs to the field of fine chemical industry. A new catalyst 1-n butyl benzimidazole hydrochloride is provided for synthesis of the acyloin compounds, and the products have the advantages of good quality and less side reactions; deficiencies existed in the prior art are overcome.

Description

technical field [0001] The invention belongs to the field of fine chemicals, and in particular relates to a preparation method of azoin compounds. Background technique [0002] Azoin condensation reaction products are usually important spices and their intermediates, pesticides and pharmaceutical intermediates, such as widely used spice compounds acetoin, propioin, butyroin, etc. are usually prepared by azoin condensation reaction. [0003] Acetoin, also known as 3-hydroxy-2-butanone, structural formula Colorless or pale yellow liquid with a creamy aroma. Traditional preparation methods include: ① Extraction from natural products such as cream, cocoa, strawberry, etc., but the yield is extremely low and the extraction is difficult; Fungi such as Penicillium act on sugarcane juice to obtain acetoin, but this method has low yield, high cost and small scale; ③ chemical synthesis method, using 2,3-butanedione as raw material to reduce and prepare acetoin, but the yield And p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/45C07C49/17B01J31/02
CPCB01J31/0244C07C45/45C07C49/17
Inventor 郑大刚李鹏毅杨河峰蔡存现文教刚吕孝永
Owner 濮阳天源生物科技有限公司
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