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Method for directly introducing aldehyde group to aromatic ring

A direct, aromatic ring technology, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems of aromatic hydrocarbon conversion rate, low aromatic aldehyde selectivity, etc.

Pending Publication Date: 2020-04-28
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is the problem of low conversion rate of aromatic hydrocarbons and low selectivity of aromatic aldehydes. A new method for directly introducing aldehyde groups on aromatic rings is provided, which has high conversion rate of aromatic hydrocarbons and high selectivity of aromatic aldehydes specialty

Method used

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  • Method for directly introducing aldehyde group to aromatic ring
  • Method for directly introducing aldehyde group to aromatic ring
  • Method for directly introducing aldehyde group to aromatic ring

Examples

Experimental program
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preparation example Construction

[0044] Preparation of IL / silica gel: in N 2 Calcined 100g of silica gel at 400°C for 6 hours in the atmosphere, cooled to room temperature, and stored in a glove box for later use; N 2 In the atmosphere, 25g of ionic liquid was added to the pretreated silica gel, stirred at 200rpm for 20h; 200ml of CH was added to it 2 Cl 2 , to wash off the unloaded ionic liquid, and wash for 0.5h; the washed IL / silica gel was dried in a vacuum oven at 0.1kpa, 40°C for 2h; stored in a glove box for later use; the IL / silica gel was measured by ICP-AES characterization means The weight fraction of Al in silica gel is 2.66%.

[0045] Preparation of IL / SBA-15: In N 2 Calcined 100g of SBA-15 at 400°C for 6 hours in the atmosphere, cooled to room temperature, and stored in a glove box for later use; N 2 In the atmosphere, add 25g of ionic liquid to the pretreated SBA-15, stir at 200rpm for 20h; add 200ml of CH 2 Cl 2 , wash off the unloaded ionic liquid, and wash for 0.5h; the washed IL / SBA-1...

Embodiment 1

[0051] Add IL / silica gel containing 5g Al, 200ml cyclohexane, CrCl containing 6g Cr in the autoclave 3 , the air in the kettle is first filled with N 2 Replaced 3 times, then replaced 3 times with CO gas; stirred at 500rpm for 1h; added 20g of toluene, and replaced 3 times with CO gas; raised the temperature to 50°C, kept the CO pressure at 2.0MPa, stirred at 500rpm, and reacted for 4h to obtain p-methyl Product mixture of benzaldehyde.

[0052] For ease of comparison and illustration, the conversion rate of catalyst formula, toluene and the selectivity of p-toluene are listed in Table 1.

Embodiment 2

[0054] Add IL / silica gel containing 5g Al, 200ml cyclohexane, VCl containing 6g V in the autoclave 3 , the air in the kettle is first filled with N 2 Replaced 3 times, then replaced 3 times with CO gas; stirred at 500rpm for 1h; added 20g of toluene, and replaced 3 times with CO gas; raised the temperature to 50°C, kept the CO pressure at 2.0MPa, stirred at 500rpm, and reacted for 4h to obtain p-methyl Product mixture of benzaldehyde.

[0055] For ease of comparison and illustration, the conversion rate of catalyst formula, toluene and the selectivity of p-toluene are listed in Table 1.

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Abstract

The invention relates to a method for directly introducing an aldehyde group to an aromatic ring. A purpose of the invention is mainly to solve the problems of low aromatic hydrocarbon conversion rateand low aromatic aldehyde selectivity in the prior art. According to the technical scheme, the method comprises the step of performing a carbonylation reaction on aromatic hydrocarbon and CO under the catalysis of a catalyst to obtain aromatic aldehyde, wherein the catalyst comprises a carrier, an ionic liquid and a compound-state auxiliary agent metal, the carrier is a silicon-based material, the ionic liquid comprises aluminum halide and an imidazole salt represented by a chemical formula I, R1 and R2 are independently selected from C1-C8 alkyl, X is selected from chlorine and bromine, thealuminum halide is represented as AlY3, Y is selected from chlorine and bromine, and the compound-state auxiliary metal comprises at least one selected from Cu, Fe, Cr, V and Mn.

Description

technical field [0001] The present invention relates to a method for directly introducing an aldehyde group on an aromatic ring. Background technique [0002] The synthesis methods of aromatic aldehydes mainly include direct high temperature oxidation, indirect electrosynthesis and carbonylation. p-Tolualdehyde is one of the aromatic aldehydes, that is, 4-methylbenzaldehyde (p-Tolualdehyde, PTAL for short), is a colorless or light yellow transparent liquid with a gentle floral and almond aroma, which is harmful to the eyes and skin There is a certain irritation. P-tolualdehyde can be highly selectively oxidized to synthesize terephthalic acid, and it is also an important intermediate in organic synthesis, which is widely used in fine chemical and pharmaceutical fields. Take the synthesis of PTAL as an example: [0003] The direct high-temperature oxidation method uses p-xylene as a raw material to prepare PTAL through photobromination, alkaline hydrolysis, and oxidation o...

Claims

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Application Information

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IPC IPC(8): C07C45/50C07C47/542C07C47/54C07C47/546B01J31/34B01J31/36B01J31/32
CPCC07C45/50B01J31/34B01J31/36B01J31/32C07C47/542C07C47/54C07C47/546
Inventor 王艳红肖忠斌杨运信查晓钟
Owner CHINA PETROLEUM & CHEM CORP
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