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Preparation method of adipic acid

A technology of adipic acid and cyclohexanone, which is applied in the field of preparation of adipic acid, can solve the problems of high temperature, lowering, unfavorable production costs, etc., and achieve the effects of simple and gentle post-processing, increased dosage, and less environmental pollution

Active Publication Date: 2021-10-26
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The emergence of hydrogen peroxide or transition metal salts to catalyze the oxidation of cyclohexanone, although the emission of toxic gases in traditional industrial production is avoided, but the reaction requires a large amount of hydrogen peroxide as an oxidant and a high-valent metal salt as a pre-catalyst, and the temperature is generally high. Not conducive to the reduction of industrial production costs

Method used

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  • Preparation method of adipic acid
  • Preparation method of adipic acid
  • Preparation method of adipic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] This embodiment includes the following steps:

[0026] (1) In a 100mL Schlenk tube equipped with a magnet, add Cu(OTf) 2 (180mg, 5mol%), rosebic acid (145mg, 5mol%), cyclohexanone (980mg, 10mmol) were dissolved in 2mL of acetonitrile, added in the reaction tube under the air atmosphere, then deionized water (900mg, 50mmol ) was dissolved in 2 mL of acetonitrile, added to the reaction tube, and 46 mL of acetonitrile was added.

[0027] (2) The reaction was carried out under the irradiation of blue light (460-470nm, 10W), and the reaction was monitored through a TLC plate.

[0028] (3) Distill the reacted mixed solution under reduced pressure, remove the solvent, use 200-300 mesh silica gel for column chromatography separation, use ethyl acetate / petroleum ether (1:1) as eluent, or pass acetic acid Recrystallization from ethyl ester / n-hexane gave adipic acid (0.89 g, yield 61%) as a white solid.

[0029] figure 1 , figure 2 Respectively the proton nuclear magnetic sp...

Embodiment 2

[0031] This embodiment includes the following steps:

[0032] (1) In a 100mL Schlenk tube equipped with a magnet, add Cu(OTf) 2 (180mg, 5mol%), rosebic acid (145mg, 5mol%); Oxygen was pumped out of the reaction tube three times by an oil pump, under an oxygen atmosphere, cyclohexanone (980mg, 10mmol) was dissolved in 2mL of acetonitrile, added to In the reaction tube, deionized water (900 mg, 50 mmol) was dissolved in 2 mL of acetonitrile, added to the reaction tube, and 46 mL of acetonitrile was added.

[0033] (2) The reaction was carried out under the irradiation of blue light (460-470nm, 10W), and the reaction was monitored through a TLC plate.

[0034] (3) Distill the reacted mixed solution under reduced pressure, remove the solvent, use 200-300 mesh silica gel for column chromatography separation, use ethyl acetate / petroleum ether (1:1) as eluent, or pass acetic acid Recrystallization from ethyl ester / n-hexane gave adipic acid (0.96 g, yield 66%) as a white solid.

Embodiment 3

[0036] This embodiment includes the following steps:

[0037] (1) In a 20mL Schlenk tube equipped with a magnet, add Cu(OTf) 2 (18mg, 5mol%), rosebic acid (14.5mg, 5mol%); the reaction tube was evacuated nitrogen three times through an oil pump, under nitrogen atmosphere, cyclohexanone (98mg, 1mmol) was dissolved in 1mL of acetonitrile, added In the reaction tube, dissolve deionized water (90 mg, 5 mmol) in 1 mL of acetonitrile and add to the reaction tube, dissolve hydrogen peroxide (113 mg, 2 mmol, 60%) in 1 mL of acetonitrile and add to the reaction tube , add 7 mL of acetonitrile.

[0038] (2) The reaction was carried out under the irradiation of blue light (460-470nm, 10W), and the reaction was monitored through a TLC plate.

[0039] (3) Distill the reacted mixed solution under reduced pressure, remove the solvent, use 200-300 mesh silica gel for column chromatography separation, use ethyl acetate / petroleum ether (1:1) as eluent, or pass acetic acid Ethyl ester / n-hexan...

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Abstract

The invention discloses a preparation method of adipic acid. Cyclohexanone is used for synthesizing adipic acid under the irradiation of visible light, the catalysis of a photosensitizer and the oxidation environment of air, oxygen or hydrogen peroxide, the reaction conditions are mild, the reaction efficiency is high, and the cost is low. In addition, the reaction can pass through a continuous flow reactor, the reactant dosage is increased, the reaction efficiency is improved, the reaction time is shortened, and a foundation is laid for further industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a preparation method of adipic acid. Background technique [0002] Adipic acid is an important chemical raw material, often used in the synthesis of nylon-66, and also has important uses in paints, plasticizers, and pharmaceutical intermediates. There are many ways to synthesize adipic acid. The traditional industrial production is mainly through the two-step oxidation synthesis of cyclohexane. The first step is to oxidize cyclohexane to cyclohexanol and cyclohexanone with oxygen under the catalysis of transition metal ions; the second concentrated HNO 3 Oxidation of cyclohexanol and cyclohexanone to produce adipic acid. However, a large amount of toxic gases such as CO, NO are produced during the second oxidation step x ,N 2 O, etc., and the strong acid is corrosive to the reaction equipment. In today's era when green synthesis is widely advocated, how to reduce ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/31C07C55/14
CPCC07C51/31C07C51/313C07C55/14
Inventor 郭丽娜辛宏段新华杨铭宇
Owner XI AN JIAOTONG UNIV
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