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A kind of production technology of cyclohexanecarboxylic acid

A cyclohexanecarboxylic acid and production process technology, applied in carboxylate preparation, organic compound preparation, organic chemistry, etc., can solve the problems of many operation steps, long steps of Grignard reagent method, low yield, etc., and meet the reaction conditions Safety, easy operation, and high productivity

Active Publication Date: 2020-09-15
HUBEI JINGHONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the catalytic hydrogenation of benzoic acid requires high-pressure hydrogenation, the reaction conditions are harsh, and the operation risk is high; the Grignard reagent method has long steps, many operating steps, and low yield

Method used

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  • A kind of production technology of cyclohexanecarboxylic acid
  • A kind of production technology of cyclohexanecarboxylic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The first step is to dissolve 9.8kg (100mol) epoxycyclohexane in 50L DMF, add 2.4kg (100mol) Mg powder under stirring, cool down to -15°C to -5°C, and pass carbon dioxide gas into the solution At the same time, add 16.3kg (150mol) TMSCl, react for 6-8h, detect the completion of the reaction, control the temperature below 0°C, add the filtrate to 1N hydrochloric acid solution, adjust the pH = 3-4, extract twice with 80L ethyl acetate, half-saturated Wash with salt water, obtain 13.25kg (92mol) 2-hydroxycyclohexanecarboxylic acid after distillation of the organic layer, the yield is 92%, and the cis-trans ratio as determined by NMR is 2.2:7.8; the sample is obtained after column chromatography separation, trans-H NMR (400MHz, CDCl3+D2O): 3.70-3.78 (m, 1H), 2.22-2.32 (m, 1H), 1.12-2.01 (m, 8H). cis-H NMR (400MHz, CDCl3+D2O): 4.18-4.22 (m, 1H), 2.50-2.58 (m, 1H), 1.22-1.98 (m, 8H).

[0019] Second step, 13.25kg (92mol) 2-hydroxycyclohexanecarboxylic acid is dissolved in 30...

Embodiment 2

[0021] The first step is to dissolve 9.8kg (100mol) epoxycyclohexane in 50L NMP, add 2.4kg (100mol) Mg powder under stirring, cool down to -15°C to -5°C, and pass carbon dioxide gas into the solution At the same time, add 16.3kg (150mol) TMSCl, react for 8 hours, check that the reaction is complete, control the temperature below 0°C, add the filtrate to 1N hydrochloric acid solution, adjust the pH=3-4, extract twice with 80L ethyl acetate, wash with half-saturated salt water 13.6kg (94.5mol) of 2-hydroxycyclohexanecarboxylic acid was obtained after distillation of the organic layer, the yield was 94.5%, and the cis-trans ratio determined by NMR was 2.6:7.4;

[0022] In the second step, 13.6kg (94.5mol) of 2-hydroxycyclohexanecarboxylic acid was dissolved in 30L ethanol, 0.68kg 10% Pd / C and 0.25kg perchloric acid were added, after the gas in the kettle was replaced with nitrogen for three times, H 2 To 3-4 kg pressure, heat up to 40-45 ° C for 5 hours, filter to remove Pd / C, ev...

Embodiment 3

[0024] The first step is to dissolve 9.8kg (100mol) epoxycyclohexane in 50L NMP, add 2.88kg (120mol) Mg powder under stirring, cool down to -15°C to -5°C, and pass carbon dioxide gas into the solution Add 19.5 kg (180 mol) TMSCl at the same time, after 10 hours of reaction, check that the reaction is complete, control the temperature below 0°C, add the filtrate to 1N hydrochloric acid solution, adjust the pH to 3-4, extract twice with 80 L of ethyl acetate, wash with half-saturated saline 13.8kg (95.8mol) of 2-hydroxycyclohexanecarboxylic acid was obtained after distillation of the organic layer, the yield was 95.8%, and the cis-trans ratio was 2.3:7.7;

[0025] In the second step, 13.8kg (95.8mol) of 2-hydroxycyclohexanecarboxylic acid was dissolved in 30L ethanol, 0.6kg 10% Pd / C and 0.2kg perchloric acid were added, after the gas in the kettle was replaced with nitrogen for three times, H 2 To 3-4 kg pressure, heat up to 40-45 ° C for 5 hours, filter to remove Pd / C, evaporat...

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Abstract

The invention discloses a production process of cyclohexanecarboxylic acid and belongs to the field of chemical synthesis. Cyclohexene oxide is used herein as a starting material to react with carbondioxide, Mg powder and TMSCl (trimethylsilyl chloride); Pd / C catalytic hydrogenation is performed in the presence of an acid to obtain the cyclohexanecarboxylic acid. The production process has good safety and good operational simplicity and is suitable for industrial production.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a production process of cyclohexanecarboxylic acid. Background technique [0002] Cyclohexanecarboxylic acid is an important organic synthesis intermediate, which can be used to synthesize photoinitiator 184 and pyriquine, and can also be used as petroleum clarifier and vulcanized rubber solubilizer. [0003] At present, there are many synthetic methods of hexamethylene carboxylic acid, preferably benzoic acid catalytic hydrogenation method and Grignard reagent method (first cyclohexanol is chlorinated into chlorocyclohexane, and then Grignard reagent is made into Grignard reagent in the industry). carbon dioxide, and finally acid hydrolysis to obtain cyclohexanecarboxylic acid) and other methods. [0004] However, the benzoic acid catalytic hydrogenation method requires high-pressure hydrogenation, the reaction conditions are harsh, and the operation risk is high; the Grignard...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C61/08C07C51/377C07C51/15C07C62/04
CPCC07C51/15C07C51/377C07C2601/14C07C62/04C07C61/08
Inventor 杨辉王勇丽崔军霞张永
Owner HUBEI JINGHONG CHEM