Application of N-hydroxy compound containing nitrogen aromatic ring in hydrocarbon oxidation

An aromatic ring nitrogen hydroxyl compound technology, applied in the field of hydrocarbon oxidation reaction, can solve the problems of few types of organic nitrogen hydroxyl compounds, prone to excessive oxidation reaction, cumbersome, requiring four to five steps, etc., and achieves easy operation and high goals. Product selectivity, effect of simple synthesis method

Active Publication Date: 2010-01-13
中科化物(大连)科技实业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the selectivity of this type of compound is poor, and it is prone to excessive oxidation reaction, forming tar and slagging, so that the application is limited
Dalian Institute of Chemical Physics has developed a metal-free catalytic system, the main catalyst is nitrogen hydroxyphthalimide, and the co-catalyst is quinone compound. Good conversion; the catalyst is a nitrogen hydroxyl compound with a phenyl aromatic ring structure; so far, there are very few organic nitrogen hydroxyl compounds with a nitrogen-containing aromatic ring, and the reported synthetic method steps are cumbersome, requiring four to five steps Or it needs to use dangerous goods such as sodium methoxide in the synthesis process, which is not easy to operate; there is no report that organic nitrogen hydroxyl compounds with nitrogen-containing aromatic rings are used as catalysts for selective oxidation of hydrocarbons

Method used

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  • Application of N-hydroxy compound containing nitrogen aromatic ring in hydrocarbon oxidation
  • Application of N-hydroxy compound containing nitrogen aromatic ring in hydrocarbon oxidation
  • Application of N-hydroxy compound containing nitrogen aromatic ring in hydrocarbon oxidation

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Example 1: Synthesis of 6-hydroxypyrrolo[3,4-b]pyridine-5,7-dione

[0021] Add anhydrous sodium carbonate and hydroxylamine hydrochloride to the flask, add glacial acetic acid, and heat to reflux in an oil bath for 5 minutes. Add pyridine dicarboxylic anhydride and heat to reflux. Cool slightly after the reaction, pour into a small beaker, let it stand for cooling, crystals are precipitated, and the target product is obtained by suction filtration with a yield of 50%. It was identified as 6-hydroxypyrrolo[3,4-b]pyridine-5,7-dione by IR and NMR. 1 H NMR (400MHz, DMSO-d 6 )δ11.01(s, 1H), 8.95(dd, 1H, J=5.2, 1.6Hz), 8.25(dd, 1H, J=7.6, 1.2Hz), 7.77(dd, 1H, J=7.6, 5.2Hz ); 13 C NMR: (400MHz, DMSO-d 6 )δ162.6, 154.6, 149.0, 130.9, 128.0, 125.3; IR (KBr, neat) 3082, 1747, 1724, 1607, 1566, 1387, 1155, 1101cm -1 .

Embodiment 2

[0022] Example 2: Synthesis of 6-hydroxypyrrolo[3,4-b]pyrazine-5,7-dione

[0023] Add anhydrous potassium carbonate and hydroxylamine hydrochloride into a two-necked flask, add acetic anhydride, and heat to reflux for 5 minutes. Add pyridine dicarboxylic anhydride and heat to reflux. After the reaction was finished and cooled slightly, it was poured into a small beaker, left to cool, crystals were precipitated, and the yield was 30%. It was identified as 6-hydroxypyrrolo[3,4-b]pyrazine-5,7-dione by IR and NMR. 1 H NMR (400MHz, DMSO-d 6 )δ11.31(s, 1H), 8.96(s, 1H); 13 C NMR: (400MHz, DMSO-d 6 )δ161.2, 148.3, 145.4; IR (KBr, neat) 3087, 1751, 1731, 1608, 1535, 1369, 1274, 1164, 1118cm -1 .

Embodiment 3

[0024] Embodiment 3: air oxidation of tetralin

[0025] In a 100 ml three-necked flask, put 20 ml of tetralin and 0.3 g of 6-hydroxypyrrolo[3,4-b]pyridine-5,7-dione; heat up to 80°C while stirring, and insert the reaction solution The air guide tube inside is fed into air continuously, and the air flow rate is 50 ml / min, and the excess air is discharged from the serpentine condensing tube, reacted for 15 hours, and analyzed the product composition with a gas chromatograph. As a result, the conversion of tetralin was 80%, and the selectivity of α-tetralone was 93%.

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Abstract

The invention relates to hydrocarbon oxidation reactions, in particular to application of an N-hydroxy compound containing a nitrogen aromatic ring in hydrocarbon oxidation, wherein the organic N-hydroxy compound containing the nitrogen aromatic ring is used as the main catalyst, molecular oxygen is used as an oxygen source, and under the condition that the pressure is between 0.1 and 1.0 MPa, the temperature is between 25 and 200 DEG C, and the mass concentration of the N-hydroxy compound containing the nitrogen aromatic ring is between 0.1 and 20 percent, a hydrocarbon compound is oxidized selectively to obtain high catalytic activity. In the catalytic hydrocarbon oxidation reaction, the N-hydroxy compound containing the nitrogen aromatic ring has the characteristics of mild condition, high efficiency, environmental protection and the like; besides, the N-hydroxy compound containing the nitrogen aromatic ring has the advantages of simple synthetic method, mild preparation condition, easy operation and high yield.

Description

technical field [0001] The present invention relates to oxidation reaction of hydrocarbons, specifically a kind of synthesis of nitrogen-containing aromatic ring nitrogen hydroxyl compound and its application in hydrocarbon oxidation; the synthesis method uses dicarboxylic acid or acid anhydride containing corresponding nitrogen aromatic ring as raw material, It is heated in an organic solvent with hydroxylamine hydrochloride and an acid-binding agent in one step to synthesize an organic nitrogen hydroxyl compound containing a corresponding nitrogen aromatic ring. The application of catalytic hydrocarbon oxidation consists of this type of organic nitrogen hydroxyl compound as the main catalyst, and metal salts or quinone compounds as co-catalysts. The main catalyst is used alone, or forms a composite catalytic system with a co-catalyst, and uses air or oxygen as the oxygen source to efficiently catalyze and oxidize hydrocarbon compounds under certain conditions. Background t...

Claims

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Application Information

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IPC IPC(8): B01J31/02B01J31/04C07C27/12C07C29/50C07C45/32C07C51/21
Inventor 徐杰张巧红陈晨苗虹马红高进
Owner 中科化物(大连)科技实业有限公司
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