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Method for preparing aromatic aldehyde

A technology for aromatic aldehydes and compounds, applied in the field of preparation of aromatic aldehydes, can solve the problems of high price of hexafluoroisopropanol, unfavorable industrial application, reduced efficiency and the like

Active Publication Date: 2021-09-10
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wherein toluene is oxidized, the selectivity of benzaldehyde can reach 90%, and the conversion rate of toluene can reach 90%, but the price of hexafluoroisopropanol is high, and needs to use the compound quality shown in larger solvent formula (I) in the reaction system Ratio (>30:1), the cost of the aromatic aldehyde obtained by this oxidation method is too high, which is not conducive to industrial application; if the relatively cheap trifluoroethanol is used instead of hexafluoroisopropanol as the solvent, the efficiency of the catalyst to initiate the reaction will be greatly improved Decrease, toluene conversion rate will drop from 91% to 7%

Method used

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  • Method for preparing aromatic aldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1-6 and comparative example 1-3

[0054] Add respectively 0.5mmol nitric acid or nitrate (when being nitric acid, what add is the concentrated nitric acid aqueous solution of 66% mass fraction, wherein the molar weight of nitric acid molecule is 0.5mmol), 1mmol NHPI, 10mmol toluene and 20g 2,2,2-Trifluoroethanol (TFE), feed 1 atmosphere of pure oxygen (purity greater than 99%), replace the gas three times, in a pure oxygen atmosphere, heat the water bath to 50°C, start stirring, stirring mode For magnetic stirring, the stirring speed is 800 rev / min, start timing, after reacting for 24 hours, stop the reaction, after cooling to room temperature, sampling analysis (GC internal standard method analysis, internal standard is biphenyl), the specific results are shown in Table 1 shown.

[0055] Table 1

[0056]

[0057]

Embodiment 7-8 and comparative example 4-9

[0059] In the reactor of 50mL, add 0.02mol toluene, 10mol% (accounting for toluene mol ratio) NHPI, 5mol% (accounting for toluene mol ratio) Fe(NO 3 ) 3 9H 2 O, add 20g of different solvents to the reaction kettle, feed 1 atmosphere of pure oxygen (>99%) into the kettle, replace the gas three times, heat to 50°C in a pure oxygen atmosphere, start stirring, and the stirring speed is 800 rpm / minute, start timing, after reacting 24h, stop reaction, after being cooled to room temperature, sampling analysis (GC internal standard method analysis, internal standard is biphenyl), concrete result is shown in table 2.

[0060] Table 2

[0061]

Embodiment 9-15

[0063] In the reactor of 50mL, add the compound shown in 0.02mol formula (I), 10mol% (accounting for the compound molar ratio shown in formula (I)) NHPI, 5mol% (accounting for the compound molar ratio shown in formula (I)) Fe(NO 3 ) 3 9H 2 0, add 20g 2,2,2-trifluoroethanol in the reactor again as solvent, pass into the pure oxygen (>99%) of 1 atmospheric pressure in the still, replace gas three times, be heated to 50 under pure oxygen atmosphere ℃, start stirring, the stirring speed is 800 rev / min, start timing, after reacting for 24h, stop the reaction, after cooling to room temperature, sampling analysis (GC internal standard method analysis, internal standard is biphenyl), specific results refer to Table 3 shown.

[0064] table 3

[0065]

[0066] Measured: product in embodiment 9 Mass Spectrum See figure 1 shown.

[0067] Measured: product in embodiment 10 Mass Spectrum See figure 2 shown.

[0068]Measured: product in embodiment 11 Mass Spectrum See ima...

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Abstract

The invention discloses a method for preparing aromatic aldehyde, which comprises the following steps: a toluene compound is subjected to a catalytic oxidation reaction in the presence of an oxidizing agent and in a catalytic system to generate aromatic aldehyde, wherein the catalytic system comprises a halogenated alcohol solvent, nitrate ions and a free radical initiator, and halogen in the halogenated alcohol solvent is fluorine and / or chlorine. The method not only can obtain aromatic aldehyde with high selectivity, but also has an ideal conversion rate.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing aromatic aldehydes. Background technique [0002] Aromatic aldehyde compounds are a class of chemical raw materials with high added value, which are widely used in medicine, dyes, spices, materials and other fields, and the market demand is huge. For example, p-tert-butylbenzaldehyde is the raw material for the synthesis of lyral (α-methyl-p-tert-butylphenylpropanal), which is widely used in cloves, lily, lily of the valley, lilac, cyclamen , camellia and other fragrances for daily use, the aroma is gentle, delicate and elegant. Another example, benzaldehyde, commonly known as bitter almond oil, is one of the most important aromatic aldehydes used in industry. It is widely used in medicine, flavors and fragrances, dyes, pesticides, and materials, with an annual demand of more than 100,000 tons. It can be used in the production of benzyl alcoho...

Claims

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Application Information

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IPC IPC(8): C07C45/36C07C47/54C07C47/542C07C47/55C07C47/575C07C67/29C07C69/157
CPCC07C45/36C07C67/29C07C47/54C07C47/542C07C47/55C07C47/575C07C69/157
Inventor 李浩然袁浩然姚加应花城李景波陈志荣胡柏剡于洋
Owner ZHEJIANG UNIV
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