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Preparation method of vitamin A acetate

A technology of acetate and vitamins, applied in the direction of organic chemistry, etc., can solve the problems of low yield and high process safety risk, and achieve the effect of simplifying the reaction route, improving safety, and eliminating potential safety hazards

Active Publication Date: 2022-07-01
SHANGYU NHU BIOCHEM IND +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems of high process safety risk and low yield in the above-mentioned process, the present invention provides an improved preparation method of vitamin A acetate, which directly reacts 4-hydroxy-2-butanone with acetylene without going through The preparation and purification process of methyl ketene and cis-hexacarbon alcohol improves the safety of this process route and greatly improves the raw material utilization rate of 4-hydroxy-2-butanone

Method used

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  • Preparation method of vitamin A acetate
  • Preparation method of vitamin A acetate
  • Preparation method of vitamin A acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (1) Synthesis of compound (II)

[0039] The ether solution of ethynyl lithium (100 mL, 0.5 mol of ethynyl lithium) was pre-cooled to -15 °C, and the ether solution of 4-hydroxy-2-butanone (50 mL, 0.2 mol of 4-hydroxy-2-butanone) was slowly added dropwise. , 0.5h was added dropwise, and the reaction was continued at -15~-10℃ for 1h.

[0040] (2) Synthesis of compound (III)

[0041] The solid lithium amide (0.25mol) was put into the reaction solution obtained in step (1), and the reaction was stirred at -15 to -10° C. for 1.5 h. After the reaction was completed, 3-methyl-4-pentyne-1,3-diol ether solution (25mL, 0.07mol diol) was slowly added dropwise, the dropwise addition was completed in 0.5h, and the reaction was continued at -15~-10°C for 1.5 hours. h.

[0042] (3) Synthesis of compound (IV)

[0043] 2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde (0.2mol) was slowly added dropwise to step (2) In the obtained reaction solution, the dropwise add...

Embodiment 2

[0054] (1) Synthesis of compound (II)

[0055] The isopropyl ether solution of ethynyl lithium (100 mL, 0.5 mol ethynyl lithium) was pre-cooled to -10 °C, and 4-hydroxy-2-butanone isopropyl ether solution (50 mL, 0.2 mol of 4-hydroxy-2-butanone) was slowly added dropwise. -butanone), the dropwise addition was completed for 1 h, and the reaction was continued at -15 to -10 °C for 1.5 h.

[0056] (2) Synthesis of compound (III)

[0057] The solid lithium amide (0.25mol) was put into the reaction solution obtained in step (1), and the reaction was stirred at -15 to -10° C. for 1.5 h. After the reaction was completed, 3-methyl-4-pentyne-1,3-diol isopropyl ether solution (25 mL, 0.08 mol of diol) was slowly added dropwise, the dropwise addition was completed for 1 h, and the reaction was continued at -10 to -5 °C. 2h.

[0058] (3) Synthesis of compound (IV)

[0059] 2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde (0.2mol) was slowly added dropwise to step (2)...

Embodiment 3

[0070] (1) Synthesis of compound (II)

[0071] The isopropyl ether solution of ethynyl lithium (100 mL, 0.5 mol ethynyl lithium) was pre-cooled to -10 °C, and 4-hydroxy-2-butanone isopropyl ether solution (50 mL, 0.2 mol of 4-hydroxy-2-butanone) was slowly added dropwise. -butanone), the dropwise addition was completed for 1 h, and the reaction was continued at -15 to -10 °C for 1.5 h.

[0072] (2) Synthesis of compound (III)

[0073] The solid lithium amide (0.25mol) was put into the reaction solution obtained in step (1), and the reaction was stirred at -15 to -10° C. for 1.5 h. After the reaction was completed, 3-methyl-4-pentyne-1,3-diol isopropyl ether solution (25 mL, 0.08 mol of diol) was slowly added dropwise, the dropwise addition was completed for 1 h, and the reaction was continued at -10 to -5 °C. 2h.

[0074] (3) Synthesis of compound (IV)

[0075] 2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butene-1-aldehyde (0.2mol) was slowly added dropwise to step (2)...

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Abstract

The invention discloses a preparation method of vitamin A acetate. The preparation method comprises the following steps: reacting a compound (I) with acetylene to obtain a compound (II); (2) reacting the compound (II) with lithium amide to obtain a compound (III); (3) reacting the compound (III) with tetradecanal, and hydrolyzing to obtain a compound (IV); (4) carrying out partial hydrogenation reaction on the compound (IV) to obtain a compound (V); (5) carrying out esterification reaction on the compound (V) to obtain a compound (VI); and (6) carrying out bromination and debromination reactions on the compound (VI) to obtain vitamin A acetate (VII), and then crystallizing to obtain a vitamin A acetate crystal product. According to the method, the 4-hydroxy-2-butanone and the acetylene directly react, and preparation and purification processes of methyl vinyl ketone and cis-hexol are not carried out, so that the safety of the process route is improved, and the raw material utilization rate of the 4-hydroxy-2-butanone is greatly improved.

Description

technical field [0001] The invention belongs to the field of vitamin preparation, in particular to a preparation method of vitamin A acetate. Background technique [0002] At present, the main process routes for vitamin A synthesis are the C15+C5 process developed by BASF and the C14+C6 process developed by Roche. The Roche process mainly includes: Darzen reaction from beta ionone, hydrolysis and decarboxylation to obtain tetradecaldehyde; methyl ketene obtained from dehydration of 4-hydroxy-2-butanone is condensed, hydrolyzed and isomerized with acetylene And separate to obtain cis-hexacarbon alcohol; cis-hexacarbon alcohol reacts with ethyl magnesium bromide to obtain bisbromomagnesium compound, which is further condensed with tetradecaldehyde, hydrolyzed, and catalytically hydrogenated to obtain hydroxyvitamin A, which is then esterified , bromination, debromination and crystallization to obtain the crystalline product of vitamin acetate. [0003] In the above-mentioned...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/12
CPCC07C403/12C07C403/08C07F1/02C07C29/685C07C29/42C07C2601/16C07C33/044
Inventor 郑兆祥张生永张文城李亚洲王徐斌徐峥谷文静
Owner SHANGYU NHU BIOCHEM IND
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