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Method for preparing p-hydroxy phenyl ethyl ketone

A technology for p-hydroxyacetophenone and phenyl acetate, which is applied in the field of preparing p-hydroxyacetophenone, can solve the problems of difficult reaction control, long reaction time, troublesome post-processing, etc., and achieves easy automatic control, stable reaction, and product yield. High rate and purity effect

Inactive Publication Date: 2019-02-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 1) Using batch (kettle) reaction method, the reaction is difficult to control, the reaction time is long, the selectivity is poor, and the yield is low
[0004] 2) Using a large excess of anhydrous Lewis acid catalyst, the post-processing is troublesome and not environmentally friendly
[0005] 3) Batch type (kettle type) reaction has a large amount of material in the online reaction, and the reagents such as anhydrous aluminum trichloride used are easily decomposed when exposed to water and air, and are easy to flush or even explode, posing a great safety hazard

Method used

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  • Method for preparing p-hydroxy phenyl ethyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add phenyl acetate (13.6kg, 100mol) into the first storage tank A, dissolve it with chloroform until it is clear, and accurately adjust the volume to 25 L to make a solution with a concentration of phenyl acetate of 4.0 mol / L, stir well and seal it for later use. Add aluminum trichloride (20 kg, 150 mol) into the second storage tank B, dissolve it with chloroform until it is clear, and accurately adjust the volume to 200 L to make a solution with a concentration of aluminum trichloride of 0.75 mol / L and seal it for use .

[0025] The materials in the first storage tank A and the second storage tank B are transported through the first metering pump P1 and the second metering pump P2 respectively, and enter the mixer T for mixing, and the mixed raw material liquid continuously enters the tubular reactor for Fries rearrangement Reaction (the inner diameter of the pipeline is 0.31 cm, the length of the pipeline is 50m, and the molar flow ratio of phenyl acetate: aluminum t...

Embodiment 2

[0027] Add phenyl acetate (13.6kg, 100mol) into the first storage tank A, dissolve it with nitromethane until it is clear, and accurately adjust the volume to 25L to make a solution with a phenyl acetate concentration of 4.0 mol / L, stir well and seal it stand-by. Add aluminum trichloride (20 kg, 150 mol) into the second storage tank B, dissolve it with nitromethane until it is clear, and accurately adjust the volume to 200 L to make a solution with a concentration of aluminum trichloride of 0.75 mol / L and seal it stand-by.

[0028] The materials in the first storage tank A and the second storage tank B are transported through the first metering pump P1 and the second metering pump P2 respectively, and enter the mixer T for mixing, and the mixed raw material liquid continuously enters the tubular reactor for Fries rearrangement Reaction (the inner diameter of the pipeline is 0.31 cm, the length of the pipeline is 50m, and the molar flow ratio of phenyl acetate: aluminum trichl...

Embodiment 3

[0031] Add phenyl acetate (13.6kg, 100mol) into the first storage tank A, dissolve it with chlorobenzene until it is clear, and accurately adjust the volume to 25 L to make a solution with a concentration of phenyl acetate of 4.0 mol / L, stir well and seal it stand-by. Add aluminum trichloride (20 kg, 150 mol) into the second storage tank B, dissolve it with chlorobenzene until it is clear, and accurately adjust the volume to 200 L to make a solution with a concentration of aluminum trichloride of 0.75 mol / L. use.

[0032] The materials in the first storage tank A and the second storage tank B are transported through the first metering pump P1 and the second metering pump P2 respectively, and enter the mixer T for mixing, and the mixed raw material liquid continuously enters the tubular reactor for Fries rearrangement Reaction (the inner diameter of the pipeline is 0.31 cm, the length of the pipeline is 50m, and the molar flow ratio of phenyl acetate: aluminum trichloride is c...

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Abstract

The invention discloses a method for preparing p-hydroxy phenyl ethyl ketone. The method comprises steps as follows: phenyl acetate represented as formula (I) and Lewis acid are dispersed in an organic solvent, a mixed raw material solution is subjected to a Fries rearrangement reaction in a tubular reactor, the solution obtained after the reaction is subjected to aftertreatment, and p-hydroxy phenyl ethyl ketone represented as formula (II) is prepared; the reaction formula of the Fries rearrangement reaction is shown in the description. With the adoption of a mode of tubular reaction similarto plug flow, backmixing of the materials in the tubular reaction is almost avoided, mass and heat transfer efficiency is high, side reactions are obviously reduced, reaction selectivity is good, 2-hydroxyacetophenone as a rearrangement byproduct is obviously reduced, and product yield and purity are both higher.

Description

technical field [0001] The invention relates to a method for preparing p-hydroxyacetophenone. Background technique [0002] 4-Hydroxyacetophenone is widely used in medicine, chemical industry, pesticide and other fields. 4-Hydroxyacetophenone is one of the active ingredients of Chinese herbal medicine Capillaris, which has choleretic effect. It can be used clinically to treat cholecystitis, hepatitis or liver damage, and can also As a raw material for the synthesis of other drugs such as antipyretic and analgesic paracetamol, it can also be used in the production of flavors and fragrances. It is reported in the literature that the synthetic method of p-hydroxyacetophenone mainly uses phenyl acetate as a raw material, and is prepared through Fries rearrangement reaction under acid catalysis (J. Mol. Cat. A.: Chemical, 2002, 182-183, 137-141 ; Synlett, 2012, 23, 1927-1930; Tetrahedron, 2011, 67, 641-649; J. Chem. S°C., 1958, 2926-9). Prepare p-hydroxyacetophenone with this m...

Claims

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Application Information

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IPC IPC(8): C07C45/54C07C49/825
CPCC07C45/54C07C49/825
Inventor 金灿孙彬苏为科
Owner ZHEJIANG UNIV OF TECH
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