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Method for splitting DL-menthol by means of pre-column derivatization high performance liquid chromatography

A high-performance liquid chromatography and pre-column derivatization technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of low sensitivity and inability to achieve complete separation, and achieve the effect of accurate separation and separation

Inactive Publication Date: 2014-07-09
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The chiral analysis methods currently include: use substituted β-cyclodextrin as the stationary phase for gas chromatographic separation, but complete separation cannot be achieved; liquid-phase chiral analysis uses an optical rotation detector to obtain low sensitivity

Method used

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  • Method for splitting DL-menthol by means of pre-column derivatization high performance liquid chromatography
  • Method for splitting DL-menthol by means of pre-column derivatization high performance liquid chromatography
  • Method for splitting DL-menthol by means of pre-column derivatization high performance liquid chromatography

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preparation example Construction

[0041] DL-menthyl benzoate used in each embodiment of the present invention, DL-menthyl p-nitrobenzoate, DL-menthyl o-chlorobenzoate, DL-menthyl p-methoxybenzoate, The synthetic method of p-phenylbenzoic acid DL-menthyl ester, 1-naphthoic acid DL-menthyl ester or cinnamic acid DL-menthyl ester, concrete steps are as follows:

[0042] In a 250mL three-necked flask, add the corresponding aromatic acid, DL-menthol and catalyst monohydrate p-toluenesulfonic acid in sequence, the molar ratio of which is 1:1.2:0.05, add 100mL of toluene as solvent, shake well and add the magnet, install the water separator Add toluene to the water separator, heat it at about 110°C, stir and reflux, condense and separate the water. After the reaction is completed, the water in the water separator will no longer increase, and the reaction system will be cooled to room temperature. Add 20 mL of water, separate the organic layer, wash the organic layer with saturated sodium bicarbonate and saturated bri...

Embodiment 1

[0045] Aromatic acids (benzoic acid, p-nitrobenzoic acid, o-chlorobenzoic acid, p-methoxybenzoic acid, p-phenylbenzoic acid, 1-naphthoic acid or cinnamic acid) (40.94 mmol), DL-menthol (7.68g, 49.13mmol) and catalyst monohydrate p-toluenesulfonic acid (0.39g, 2.05mmol), calculated by molar ratio, that is, aromatic acid: DL-menthol: catalyst monohydrate p-toluenesulfonic acid is 1 : 1.2: 0.05, then add 100mL of toluene as a solvent, shake well and add the magnet, install the water separator, spherical condenser and drying tube, fill the water separator with toluene, heat to about 110°C, stir and reflux, Condensate and separate the water. After the reaction is completed, that is, until the water in the water separator no longer increases, the reaction system is cooled to room temperature, 20mL of water is added, and the organic layer is separated. The organic layer is washed with saturated sodium bicarbonate and saturated brine successively, and controlled Spin dry at 40-50°C to...

Embodiment 2

[0086] Adopt a kind of method of the present invention that utilizes pre-column derivatization high performance liquid chromatography to resolve DL-menthol, for 3 kinds of DL-menthyl benzoate esters and DL-menthyl p-methoxybenzoate obtained in Example 1 Ester and DL-menthyl cinnamate carry out high performance liquid chromatography separation, specifically comprise the steps:

[0087] (1) Take 25 mg of DL-menthyl benzoate, DL-menthyl p-methoxybenzoate and DL-menthyl cinnamate respectively, and mix them with acetonitrile and water. After the solution is dissolved, it is transferred to a 25mL volumetric flask, diluted to the mark with acetonitrile, shaken up, and used as the test solution;

[0088] Similarly, get 25 mg of corresponding standard L-menthol ester, dissolve and configure as the reference substance solution for testing in the same way as above;

[0089] (2) Inject the test solution and the reference solution respectively, carry out HPLC analysis according to the fol...

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Abstract

The invention discloses a method for splitting DL-menthol by means of pre-column derivatization high performance liquid chromatography. The method comprises the following steps: firstly, carrying out a precolumn derivatization esterification reaction on DL-menthol and aromatic acid to obtain corresponding ultraviolet absorption DL-mint alcohol; then, preparing the DL-mint alcohol ester to a 0.2-1.0mg / mL sample solution by adopting an opposite mobile phase system formed by an aqueous phase and an organic phase by using an amylase chiral chromatographic column through the high performance liquid chromatograph; controlling the flow rate at 0.4-1.0mL / min, the sample size at 2-10 microlitre, the detecting wave length at 220-280nm and the temperature of the wave length at 20-35 DEG C for chromatographic column separation so as to separate the DL-mint alcohol ester; and finally, respectively hydrolyzing to obtain D-menthol and L-menthol. The method for detecting and splitting menthol is convenient, practical and high in sensitivity.

Description

technical field [0001] The invention relates to a high-performance liquid chromatography separation method. Specifically, pre-column ultraviolet derivatization is performed on DL-menthol enantiomers to obtain derivatives with ultraviolet absorption, and a chiral chromatographic column and ultraviolet detector to split detections. Background technique [0002] Menthol, common name menthol, scientific name 5-methyl-2 isopropyl-cyclohexanol. Menthol is widely used in daily chemical flavors, food flavors, daily chemical flavors and medicine and hygiene. At the earliest, menthol was extracted from the natural product peppermint, and its main sources were peppermint oil and Asian peppermint oil. Because menthol has a wide range of applications, only relying on extracting from natural mint can no longer meet the growing industrial demand, so more and more manufacturers are increasingly relying on chemically synthesized menthol. At present, the methods for synthesizing menthol ma...

Claims

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Application Information

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IPC IPC(8): C07C35/12C07C29/92
CPCC07C29/92C07C35/12
Inventor 潘仙华于一文李晓军房家惠闻嘉蕴余恺王敏喆刘烽徐娜闫茜陈苏柯于万盛
Owner SHANGHAI INST OF TECH
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