Method for oxidation synthesis of adipic acid by epoxy cyclohexane

A technology for the synthesis of epoxycyclohexane and oxidation, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., and can solve the problem of low activity

Inactive Publication Date: 2008-05-14
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sang-Ok Lee et al. used TAPO-5 molecular sieve as catalyst, 30% H 2 o 2 Adipic acid is obtained by oxidizing epoxycyclohexane for the oxidant, and the yield of adipic acid is only 39.8% (Angew.Chem.Int.Ed., 2003, 42, 1520-1523) after 24 hours of reaction. As can be seen, these The main disadvantage of the catalyst is its low activity
[0005] In the absence of organic solvents, there is no report on the oxidation of cyclohexane to adipic acid catalyzed by environmentally friendly catalysts such as heteropolyacids.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 1 mmol of phosphotungstic acid (H 3 PW 12 o 40 ·nH 2 O, burning at 200°C for 16h), 55ml30%H 2 o 2 , stirred magnetically at room temperature for 10 minutes, added 10.10ml (100mmol) epoxycyclohexane, adjusted the temperature to about 92°C and stirred and refluxed for 6h, extracted with 30ml of 1,2-dichloroethane at about 80°C while it was hot, and water The phase was cooled to 0°C and left for 12 hours, the crystals were filtered out, washed with 30ml of saturated adipic acid solution at 0°C, dried in vacuo and weighed. The IR spectrum of the product is very consistent with the IR spectrum of the standard sample of adipic acid, so it can be proved that the product is adipic acid. The melting point of the product is 149.8-152.7°C. 12.1409 g of adipic acid was obtained (yield 83.2%). The product is white crystals.

Embodiment 2

[0042] Add 1mmol of phosphomolybdic acid (H 3 PMo 12 o 40 ·nH 2 O, 200 ° C burning 16h), 55ml 30% H 2 o 2 , stirred magnetically at room temperature for 10 minutes, added 10.10ml (100mmol) epoxycyclohexane, adjusted the temperature to about 92°C and stirred and refluxed for 6h, extracted with 30ml of 1,2-dichloroethane at about 80°C while it was hot, and water The phase was cooled to 0°C and left for 12 hours, the crystals were filtered out, washed with 30ml of saturated adipic acid solution at 0°C, dried in vacuo and weighed. The IR spectrum of the product is very consistent with the IR spectrum of the standard sample of adipic acid, so it can be proved that the product is adipic acid. The melting point of the product is 149.7-151.7°C. 9.1488 g of adipic acid was obtained (62.7% yield). The product is white crystals.

Embodiment 3

[0044] Add 1mmol of silicotungstic acid (H 4 SiW 12 o 40 ·nH 2 O, burning at 200°C for 16h), 55ml30%H 2 o 2 , stirred magnetically at room temperature for 10 minutes, added 10.10ml (100mmol) epoxycyclohexane, adjusted the temperature to about 92°C and stirred and refluxed for 6h, extracted with 30ml of 1,2-dichloroethane at about 80°C while it was hot, and water The phase was cooled to 0°C and left for 12 hours, the crystals were filtered out, washed with 30ml of saturated adipic acid solution at 0°C, dried in vacuo and weighed. The IR spectrum of the product is very consistent with the IR spectrum of the standard sample of adipic acid, so it can be proved that the product is adipic acid. The melting point of the product is 149.6-152.6°C. 9.5633 g of adipic acid was obtained (65.5% yield). The product is white crystals.

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PUM

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Abstract

The invention relates to a method for synthesizing adipate using cyclohexene oxide through oxidation, which uses the tungsten and molybdenum polyoxometalates as the catalyst, and the hydrogen peroxide solution as the oxidant to catalyze the oxidation of the cyclohexene oxide to synthesize the adipate. The invention is characterized in that the organic solvent is no longer used as the reacting medium, so as to avoid the environment pollution caused by using the nitric acid as the oxidant. The reacting temperature is 60 to 105 DEG C; the reacting time is 6 to 20 hours and the adipate yield can reach 46.9% to 83.2%.

Description

technical field [0001] The invention relates to a method for synthesizing adipic acid by oxidation of epoxy cyclohexane. Background technique [0002] Adipic acid is an important raw material for industrial synthesis of nylon-66 and other chemical products. With the development of society, the demand is increasing. At present, most industries use cyclohexanol and cyclohexanone as raw materials, and use nitric acid as an oxidant to oxidize adipic acid. As we all know, nitric acid severely corrodes equipment and produces a large amount of nitrogen oxides, thereby causing serious pollution to the environment. Therefore, the current industrial methods for preparing adipic acid have great limitations. [0003] In the process of preparing cyclohexanone and cyclohexanol by oxidation of cyclohexane, light oil is produced by-product at the same time, and the content of 1,2-epoxycyclohexane in light oil is 10% to 50%. This part 1,2 - Cyclohexane oxide has been underutilized. In rec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C55/14C07C51/285B01J27/188B01J23/30
Inventor 李华明纪明慧舒火明朱文帅闫永胜
Owner JIANGSU UNIV
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