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Method for preparing all-trans pseudo-ionone

A pseudo-ionone, all-trans technology, applied in the preparation of organic compounds, chemical instruments and methods, carbon-based compound preparation, etc., can solve the problem of cis-transposition problems without literature reports, etc., to prevent thermal decomposition , reduce the temperature of the kettle, and make full use of the effect

Inactive Publication Date: 2011-05-25
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

How to separate and prepare the trans-body, and the transposition of the cis-body has not been reported in the literature

Method used

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  • Method for preparing all-trans pseudo-ionone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Separation of cis-trans pseudo-ionones using a batch distillation column. The raw material contains cis-form 41wt.%, trans-form 50.6wt.%, and a small amount of light impurity components 8.4wt.%. Distillation column inner diameter 24mm, built-in stainless steel wire triangular spring packing (specification 1.0×1.0), packing height 1.5 meters. Add 500g of raw materials into the tower kettle. During the rectification operation, the temperature of the tower kettle is 150-165°C, the temperature of the tower top is 90-100°C, and the operating pressure of the tower top is 40-60Pa. : 1, 45g of light components are extracted from the top of the tower; adopting a reflux ratio of 2: 1, the temperature of the top of the tower is 100~106°C and is analyzed and detected by Agilent 7890GC to obtain 210g of cis-body and cis-trans mixture; When the content of the formula is more than 85wt.%, 150g of 96wt.% trans-pseudo-ionone is obtained by still-type short-path distillation, with a y...

Embodiment 2

[0028] Adopt the rectifying device identical with embodiment 1, filling height is reduced to 1.0 meters. Add the same raw materials as in Example 1. During the rectification operation, the temperature at the bottom of the tower is 145-160°C, the temperature at the top of the tower is 85-90°C, and the operating pressure at the top of the tower is 40-60Pa. After total reflux for 1h, use the reflux ratio 1:1, 52g of light components were extracted from the top of the tower; using a reflux ratio of 2:1, the temperature of the top of the tower was 90-102°C, analyzed and detected by Agilent 7890GC, and 160g of cis-isomer and cis-trans mixture were obtained; when the distillate When the trans-isomer content is above 83wt.%, 180 g of 95% trans-pseudo-ionone is obtained by still-type short-path distillation, with a yield of 36%; the operation time is 20 hours. 1 HNMR is the same as in Example 1.

Embodiment 3

[0030] Adopt the rectifying device identical with embodiment 1, filling height is 1.2 meters. Add the same raw materials as in Example 1. During the rectification operation, the temperature at the bottom of the tower is 145-165° C., the temperature at the top of the tower is 90-95° C., and the operating pressure at the top of the tower is 40-60 Pa. After 1 hour of total reflux, the reflux ratio 1:1, 60g of light components were extracted from the top of the tower; using a reflux ratio of 2:1, the temperature of the top of the tower was 95-102°C, analyzed and detected by Agilent 7890GC, and 150g of cis-isomer and cis-trans mixture were obtained; when the tower top temperature When the temperature is 102-108°C and the trans-isomer content of the distillate is over 80wt.%, 180g of 96% trans-pseudo-ionone is obtained by still-type short-path distillation with a yield of 36%; the operation time is 17h. 1 HNMR is the same as in Example 1.

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Abstract

The invention relates to a method for preparing all-trans pseudo-ionone, which comprises the following steps of: adding cis and trans pseudo-ionone into a batch distillation column filled with a triangular stainless steel wire spring filler, and discharging light-component pseudo-ionone, cis pseudo-ionone, cis-trans pseudo-ionone and trans pseudo-ionone partially with the purity of more than or equal to 83 weight percent from the top of the column at an adjustable reflux ratio; performing short-range tank reduced pressure distillation on cis pseudo-ionone-containing residues to obtain the trans pseudo-ionone with the purity of more than 95 weight percent; and adding the cis pseudo-iononem and the cis-trans pseudo-ionone into the aqueous solution of hydrochloric acid or sulfuric acid, performing stirring at room temperature to obtain filtrate, and performing distillation on the filtrate according to the steps to obtain the all-trans pseudo-ionone. The method can effectively reduce tanktemperature, prevent materials from being thermally decomposed and thermally polymerized and fully utilize the raw materials by completely converting the pseudo-ionone with trans isomers into the all-trans pseudo-ionone, and has the distillation characteristics of high separation efficiency, high product purity, low energy consumption and the like.

Description

technical field [0001] The invention relates to the field of biochemical industry, in particular to a preparation method of all-trans pseudoionone. Background technique [0002] Pseudo-ionone, the structural formula is [0003] [0004] It is an important raw material for the synthesis of vitamin A, vitamin E and carotene compounds. It was first prepared by Tiemann in 1893 by condensing citral with acetone under alkaline conditions. Now the Tiemann method is still an important method for industrial and laboratory synthesis of pseudoionones. For a long time people have explored the use of petrochemical raw materials to synthesize pseudo-ionones. In 1958, Kimel et al. prepared pseudo-ionones from acetylene and acetone, which had been industrialized by Hoffmann La-Roche. In 1968, Pommer et al. used isobutene as raw material to formaldehyde and acetone through Mannich reaction, and prepared by acetylenization and reduction. In 1980, Y.Fujita et al. conveniently synthesize...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/203C07C45/82C07C45/67
Inventor 陈建辉皮士卿
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY