Method for synthesizing 3, 8-dimethyl-3, 5, 7-octatriene-1, 10-dialdehyde

A technology of octatriene and dimethyl, which is applied in the field of synthesizing 3,8-dimethyl-3,5,7-octatriene-1,10-dialdehyde, which can solve the problem of high cost and unreachable synthetic route Industrialization requirements and other issues, to achieve the effect of increased yield and mature process route

Pending Publication Date: 2021-08-24
JINAN UNIVERSITY
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  • Abstract
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  • Application Information

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Problems solved by technology

This route solves the problems in the process of preparing C15 phosphonate, but the yield of dodecenal is only 21.4%, which leads to high cost of the synthetic route and cannot meet the requirements of industrialization.

Method used

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  • Method for synthesizing 3, 8-dimethyl-3, 5, 7-octatriene-1, 10-dialdehyde
  • Method for synthesizing 3, 8-dimethyl-3, 5, 7-octatriene-1, 10-dialdehyde

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Embodiment 1

[0034] A kind of synthetic method of 3,8-dimethyl-3,5,7-octatriene-1,10-dialdehyde, comprising the following steps:

[0035] Step 1: In a 200mL flask, add sodium hydroxide (1.92g, 48mmol), 6g of potassium carbonate and 50mL of a mixed solution of toluene and cyclohexane with a volume ratio of 1:1. The reaction flask was stirred at 0°C, and 2-butene-1,4-diphosphate tetraethyl ester (1.97g, 6mmol) and 4,4-dimethoxy-2- Butanone (3.17g, 24mmol) was added dropwise to the reaction flask, and 0.02g of 18-crown-6 was added. The reaction solution was reacted at 0° C. for 4 h. After the reaction was completed, 40 mL of water was added to wash, and the organic layer was taken by liquid separation, dried with anhydrous sodium sulfate, filtered, and the solvent was evaporated to dryness to obtain an intermediate product.

[0036] Step 2: Put the intermediate product obtained above in a 50 mL flask, add 4 mL of acetic acid, 2 mL of tetrahydrofuran, and 1 mL of water, stir and react at 45 ...

Embodiment 2

[0038] Step 1: In a 200mL flask, add sodium hydroxide (2.16g, 54mmol), 4g of potassium carbonate and 50mL of a mixed solution of toluene and cyclohexane with a volume ratio of 1:1. The reaction flask was stirred at 0°C, and 2-butene-1,4-diphosphate tetraethyl ester (1.97g, 6mmol) and 4,4-dimethoxy-2- Butanone (3.17g, 24mmol) was added dropwise to the reaction flask, and 0.03g of 18-crown-6 was added. The reaction solution was reacted at 0° C. for 4 h. After the reaction is completed, refer to the post-treatment method of Step 1 of Example 1 to obtain an intermediate product.

[0039] Step 2: Referring to Step 2 of Example 1, 0.43 g of the product 3,8-dimethyl-3,5,7-trienedialdehyde was obtained with a yield of 37.28%.

Embodiment 3

[0041] Step 1: Add sodium hydroxide (2.40 g, 60 mmol), potassium carbonate 2 g and 50 mL of a mixed solution of toluene and cyclohexane with a volume ratio of 1:1 in a 200 mL flask. The reaction flask was stirred at 0°C, and 2-butene-1,4-diphosphate tetraethyl ester (1.97g, 6mmol) and 4,4-dimethoxy-2- Butanone (3.17g, 24mmol) was added dropwise to the reaction flask, and 0.02g of 18-crown-6 was added. The reaction solution was reacted at 0° C. for 4 h. After the reaction is completed, refer to the post-treatment method of Step 1 of Example 1 to obtain an intermediate product.

[0042] Step 2: Referring to Step 2 of Example 1, 0.51 g of the product 3,8-dimethyl-3,5,7-trienedialdehyde was obtained with a yield of 42.80%.

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Abstract

The invention discloses a method for synthesizing 3, 8-dimethyl-3, 5, 7-octtriene-1, 10-dialdehyde, the method comprises the following steps: taking 2-butene-1, 4-tetraethyl diphosphate and 4, 4-dimethoxy-2-butanone as raw materials, firstly, taking cyclohexane and methylbenzene as solvents, adding a basic catalyst, a water-absorbing drying agent and crown ether, carrying out low-temperature reaction, then dissolving reactants in a mixed solvent of tetrahydrofuran, acetic acid and water, and carrying out a reaction at a high temperature to obtain the 3, 8-dimethyl-3, 5, 7-octtriene-1, 10-dialdehyde. The alkaline catalyst and the water-absorbing drying agent are added into a reaction system, and crown ether is added for catalysis so that the yield of the synthesized beta-carotene key intermediate is obviously increased, the synthesis process of the intermediate is optimized, the synthesis efficiency of the intermediate is improved, and the synthesis process is easy in raw material obtaining, simple in process, convenient to operate and relatively low in cost, and green development is met and industrialization is easy to achieve.

Description

technical field [0001] The invention relates to the field of food additives, in particular to a method for synthesizing 3,8-dimethyl-3,5,7-octatriene-1,10-dialdehyde. Background technique [0002] β-carotene is used as a food additive in the food field. "GB 8821-2011 Food Safety National Standard Food Additive β-Carotene" has made relevant regulations on the quality standards of chemically synthesized β-carotene. At the same time, "GB2760-2014 Food Safety National Standard Food Additive Use Standard" lists that chemically synthesized β-carotene can be used in various foods (milk and milk products, fat, oil and emulsified fat products, frozen drinks, fruits, vegetables, Cocoa products, grain and grain products, baked goods, meat and meat products, aquatic products, eggs and egg products, sweeteners, condiments, beverages, wine, etc.). [0003] At present, the preparation methods of β-carotene include plant extraction method, algae culture method, microbial fermentation metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/48C07C43/303C07C45/51C07C47/21
CPCC07C41/48C07C45/513C07C43/303C07C47/21
Inventor 晏日安陈果周华李存芝陈永生
Owner JINAN UNIVERSITY
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