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Method for preparing beta-apo-12'-carotenal

A carrot aldehyde, dripping technology, applied in the direction of organic chemistry, can solve the problems of expensive, high cost, unsuitable for industrial production, etc., and achieve the effect of low cost, less manpower, material and financial resources, and high safety

Active Publication Date: 2018-01-30
肇庆巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The cost of raw materials for the process of β-Apo-12'-carotaldehyde is relatively high. At first, vitamin A is used as a raw material, and the expensive catalyst TEMPO is also used, and its process route is not suitable for industrial production

Method used

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  • Method for preparing beta-apo-12'-carotenal
  • Method for preparing beta-apo-12'-carotenal
  • Method for preparing beta-apo-12'-carotenal

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preparation example Construction

[0031] A preparation method of β-Apo-12'-carotaldehyde, comprising,

[0032] Step 1): Under the protection of an inert gas, sodium hydride and dimethyl sulfoxide react to obtain dimethyl sulfoxide sodium salt;

[0033] Step 2): Under the protection of inert gas, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl phosphoric acid di Ethyl ester (pentadecenyl phosphate) is dissolved in an ether solvent or a dipolar aprotic solvent, and then the dimethyl sulfoxide sodium salt obtained in step 1) is added dropwise therein for transposition, and the reaction formula is as in formula I:

[0034]

[0035] Step 3): Dissolve 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde (C10-dialdehyde) in ether solvent or dipolar aprotic solvent, and then Add the transpositioned 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl phosphoric acid obtained in step 2) dropwise Diethyl ester, the two undergo Wittig-Horner condensation reaction to obtain β-apo-12'-carotaldehyde, t...

Embodiment 1

[0051] A preparation method of β-Apo-12'-carotaldehyde, comprising the following steps:

[0052] step 1):

[0053] Under the protection of nitrogen, add 0.15 mol of sodium hydride solid into a 500mL reaction bottle, and slowly add 0.5 mol of dimethyl sulfoxide dropwise under magnetic mechanical stirring. After about 30 minutes, the dropwise addition is completed, and the internal temperature rises to 60-65°C for reaction. , the bubbles in the system gradually increase. After the bubbles disappear, stop heating for 1.0-1.5 hours, and then quickly cool down to 20-30°C for the next reaction;

[0054] Step 2):

[0055] Under the protection of nitrogen, add 0.1mol pentadecyl phosphate and 100mL tetrahydrofuran into a 500mL dry three-necked flask, cool down to about -20°C, add the dimethyl sulfoxide sodium salt solution prepared above dropwise, the dropwise addition process Control the internal temperature not to exceed -5°C, complete the dropwise addition in about 15 minutes, and...

Embodiment 2

[0061] A preparation method of β-Apo-12'-carotaldehyde, comprising the following steps:

[0062] step 1):

[0063] Under the protection of nitrogen, add 0.15 mol of sodium hydride solid into a 500mL reaction bottle, and slowly add 0.5 mol of dimethyl sulfoxide dropwise under magnetic mechanical stirring. After about 30 minutes, the dropwise addition is completed, and the internal temperature rises to 60-65°C for reaction. , the bubbles in the system gradually increased, and after the bubbles disappeared, stop heating, take 1.0-1.5h, and quickly cool down to 20-30°C for the next reaction;

[0064] Step 2):

[0065] Under the protection of nitrogen, add 0.1mol pentadecyl phosphate and 100mL tetrahydrofuran into a 500mL dry three-necked flask, cool down to -20°C, add the above-prepared dimethyl sulfoxide sodium salt solution dropwise, and the dropwise addition process is controlled The internal temperature does not exceed -5°C, the dropwise addition is completed in 15 minutes, ...

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Abstract

The invention discloses a method for preparing beta-apo-12'-carotenal. The method includes utilizing dimethyl sulfoxide sodium salt prepared by means of reaction on dimethyl sulfoxide and sodium hydride as reaction alkali; carrying out transposition on pentadec-carbon phosphate ester under the condition of the alkali; carrying out Wittig-Horner condensation reaction on the pentadec-carbon phosphate ester and C10-dialdehyde after the transposition is completely carried out so as to obtain the beta-apo-12'-carotenal which is a target product. The method has the advantages that reaction routes are convenient and speedy, raw materials are simple and are easily available, only few human, material and financial resources are required by processes, and accordingly the method is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a preparation method of β-apo-12'-carotaldehyde. Background technique [0002] β-Apo-12'-carotaldehyde is a key intermediate in the synthesis of apocarotenoids, mainly used in the synthesis of β-apo-8'-carotaldehyde and β-apo-8'-carotene acetyl ester . Apocarotene is an important component of carotenoids. It is mainly used in the coloring of edible oils, margarine, jam, jelly and beverage products in food; it is widely used in the feed industry, especially the skin of broilers. , shin, fat coloring and poultry egg yolk coloring. [0003] At present, the largest manufacturers of carotenoid products in the world (such as Roche Company) all use apocarotene compound products as the main product production, which shows that its market prospect is very obvious. Patent US5773635 has reported that vitamin A is used as a raw material, and is catalyzed and oxidized to beta-ap...

Claims

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Application Information

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IPC IPC(8): C07C403/14
Inventor 叶锦廖艳金方泽华叶振兴张健文吴曼纯
Owner 肇庆巨元生化有限公司
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