Conversion and separation method for cis-trans mixture of 4-isopropyl cyclohexanecarboxylic acid

A technology of sodium isopropylcyclohexylcarboxylate and a separation method, which is applied in the preparation of organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve the problems of large solvent loss, unfriendly environment, and high cost, and achieve less environmental pollution , low price, easy operation

Inactive Publication Date: 2019-04-19
浙江清和新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, 4-isopropylcyclohexanecarboxylic acid with a trans-isomer content of 99% can be obtained by using a mixture of the cis and trans isomers of the usual thermodynamic equilibrium 4-isopropylcyclohexanecarboxylic acid through a specific separation method , mainly by directly acidifying the 65% hydrogenated solution of the trans-isomer, extracting it with chloroform, evaporating the solvent, and performing multiple recrystallizations with another ethyl acetate to obtain 4-isoform with 99.0% trans-isomer Propylcyclohexyl carboxylic acid, cis-body is treated as high boiling, this method has low efficiency, large solvent loss, unfriendly to the environment, and high cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Put 500g of hydrogenation solution and 10g of NaOH into the hydrogenation kettle. After feeding, replace with nitrogen and hydrogen. Stirring is started, the temperature is controlled at 180°C, the pressure is 1.2MPa, and the material is discharged after 10 hours of reaction to obtain a transformation liquid, which contains 85% trans-sodium-4-isopropylcyclohexanecarboxylate and 14% cis Formula - Sodium 4-isopropylcyclohexylcarboxylate;

[0021] Take the transformation solution and add hydrochloric acid dropwise at a temperature of 30°C, and add chloroform at the same time, acidify to pH ≤ 1.0, stir and let stand to separate layers, extract the water layer with chloroform again, combine the organic phase, and distill the organic phase to dryness with chloroform under normal pressure. , add acetone and heat until it is completely dissolved, then add purified water dropwise to the solution, control the temperature at 40°C, white crystals precipitate, filter with suction t...

Embodiment 2

[0023] Put 500g of hydrogenation solution and 10g of sodium carbonate into the hydrogenation kettle. After feeding, replace with nitrogen and hydrogen. Stirring was started, the temperature was controlled at 190°C, the pressure was 1.4MPa, and the material was discharged after 8 hours of reaction to obtain a transformation liquid, which contained 82% trans-sodium-4-isopropylcyclohexanecarboxylate and 17% cis Formula - Sodium 4-isopropylcyclohexylcarboxylate;

[0024] Take the transformation solution and add 30% dilute sulfuric acid dropwise at a temperature of 20°C, add chloroform at the same time, acidify to pH ≤ 1.0, stir and let stand to separate layers, extract the water layer with chloroform again, combine the organic phase, and the organic phase is normal pressure Distill chloroform to dryness, add methanol and heat until completely dissolved, then add purified water dropwise to the solution, control the temperature at 50°C, white crystals precipitate, filter with sucti...

Embodiment 3

[0026] Put 500g of hydrogenation solution and 10g of KOH into the hydrogenation kettle. After feeding, replace with nitrogen and hydrogen. Stirring is started, the temperature is controlled between 200°C and the pressure is 1.6MPa, and the material is discharged after reacting for 7 hours to obtain a transformation liquid, which contains 84% ​​trans-4-isopropyl sodium cyclohexanecarboxylate and 15% cis-4-sodium isopropylcyclohexanecarboxylate;

[0027] Take the transformation liquid and add hydrochloric acid dropwise at a temperature of 35°C, and add chloroform at the same time, acidify to pH ≤ 1.0, stir and let stand to separate layers, extract the water layer with chloroform again, combine the organic phase, and distill the organic phase to dryness with chloroform under normal pressure. , add methanol and heat until it is fully dissolved, then add purified water dropwise to the solution, control the temperature at 45°C, white crystals precipitate, filter with suction to obt...

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Abstract

The invention discloses a conversion and separation method for cis-trans mixture of 4-isopropyl cyclohexanecarboxylic acid, and belongs to the technical field of chemical separation of fine chemical industry. The method includes the following process steps: mixing 4-isopropyl sodium cyclohexanecarboxylate hygrogenation liquid and an auxiliary agent; replacing nitrogen gas with air for a system, and holding the temperature and pressure after the temperature and pressure are raised to obtain conversion liquid; and extracting and crystallizing the conversion liquid. A cis-form is converted into atrans-form by the principle of chemical thermal stability under the action of the auxiliary agent. The conversion yield is high, more than 99% of the trans-form product is obtain after post-treatment, the operation is simple, the environmental pollution is less, and the conversion and separation method for cis-trans mixture of the 4-isopropyl cyclohexanecarboxylic acid is suitable for industrialproduction. Moreover, the cis-form in crystallization mother liquor is recycled and reused by the conversion reaction, the product yield is improved, and the production of ''three wastes'' is reduced.

Description

technical field [0001] The invention belongs to the technical field of fine chemical separation, and in particular relates to a transformation and separation method of a cis-trans mixture of 4-isopropylcyclohexanecarboxylic acid. Background technique [0002] 4-Isopropylcyclohexanecarboxylic acid (TICC for short) has two isomers with different thermodynamic properties, cis and trans. The thermodynamic equilibrium content of its hydrogenation solution is: the trans isomer accounts for about 65wt%, and the cis isomer accounts for about 34wt%. , that is, trans-4-isopropylcyclohexanecarboxylic acid is the most stable structure in the thermodynamic sense of the two isomers, and the two isomers have completely different properties and uses. Trans-4-isopropylcyclohexanecarboxylic acid is an important intermediate in the synthesis of nateglin, a therapeutic drug for diabetes. [0003] At present, 4-isopropylcyclohexanecarboxylic acid with a trans-isomer content of 99% can be obtain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/353C07C61/08
CPCC07B2200/07C07B2200/09C07C51/353C07C2601/14C07C61/08
Inventor 林海峰张增礼王建符建琼泮永成
Owner 浙江清和新材料科技有限公司
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