Method for high selective preparation of aromatic aldehyde from toluene compound

A high-selectivity, compound technology, applied in the preparation of carbon-based compounds, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of slowing down the reaction speed, reducing the reaction conversion rate, limited degree, etc., to suppress excessive oxidation. , improve selectivity, low cost effect

Inactive Publication Date: 2018-04-20
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can improve the selectivity of generating aldehydes to a certain extent, the degree is limited, and the presence of water will slow down the reaction speed of the entire reaction system and reduce the reaction conversion rate.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 4.00g Co(OAc) to the reaction kettle 2 4H 2 O, 1.39g Mn(OAc) 2, 0.56g KBr, 3.94g p-tert-butylbenzyl alcohol, 59.30g p-tert-butyltoluene, 40.00g acetic acid, blow in air, pressurize to 0.2Mpa, keep the pressure with oxygen, raise the temperature to 50°C, and start stirring Timed reaction, the stirring rate is 1000r / min, after reacting for 2h, stop the reaction, after the reaction liquid is cooled, GC internal standard method analysis, p-tert-butyl toluene conversion rate is 25%, p-tert-butyl benzaldehyde selectivity is 93 %, the selectivity to p-tert-butylbenzoic acid is 4%, and the selectivity to ethyl p-tert-butylbenzoate is 2%. The reaction solution was distilled under reduced pressure to recover acetic acid to obtain 38.65 g of acetic acid. The catalyst was filtered, and a total of 4.15 g of the catalyst was recovered. Elemental analysis showed that the loss was the water of crystallization and KBr of the catalyst. Add 0.18g of NaOH powder, mix thoroughly fo...

Embodiment 2

[0042] Catalyst recovery applies mechanically, adds the 4.15g catalyst that embodiment 1 reclaims in reactor, supplements to add 0.56g potassium bromide again, 1.16g H 2 O. Add 3.94g of p-tert-butylbenzyl alcohol, 59.30g of p-tert-butyltoluene, 40.00g of acetic acid, feed air, pressurize to 0.2Mpa, keep the pressure with oxygen, raise the temperature to 50°C, stir and start timing reaction, stir The speed is 1000r / min, after reacting for 2h, stop the reaction, after the reaction solution is cooled, GC internal standard method analysis, p-tert-butyl toluene conversion rate is 23%, p-tert-butyl benzaldehyde selectivity is 90%, p-tert-butyl benzaldehyde The selectivity of butylbenzoic acid is 5%, and the selectivity of ethyl p-tert-butylbenzoate is 3%. The reaction solution was distilled under reduced pressure to recover acetic acid to obtain 38.05 g of acetic acid. The catalyst was filtered, and a total of 4.17 g of the catalyst was recovered. Add 0.18g of NaOH powder, mix th...

Embodiment 3

[0044] Add 3.00g Co(OAc) to the reaction kettle 2 4H 2 O, 1.39g Mn(OAc) 2 , 0.41g NaBr, 3.31g p-methoxybenzyl alcohol, 48.87g p-methoxytoluene, 40.00g acetic acid, feed air, pressurize to 0.2Mpa, keep the pressure with oxygen, raise the temperature to 50°C, and start stirring Timing reaction, the stirring rate is 1000r / min, after reacting for 1.5h, stop the reaction, after the reaction liquid is cooled, GC internal standard method analysis, p-methoxytoluene transformation rate is 42%, p-methoxybenzaldehyde selectivity is 85%, the selectivity to p-methoxybenzoic acid is 9%, and the selectivity to ethyl p-methoxybenzoate is 4%. The reaction solution was distilled under reduced pressure to recover acetic acid to obtain 38.72 g of acetic acid. The catalyst was filtered, and a total of 2.78 g of the catalyst was recovered. Add 0.65g of NaOH powder, mix thoroughly for 30 minutes, wash with water, and separate the aqueous phase (containing sodium benzoate) and the organic phase (...

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PUM

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Abstract

The invention discloses a method for high selective preparation of aromatic aldehyde from a toluene compound. The method includes: mixing the toluene compound, a catalytic system and a solvent, carrying out reaction in an air or oxygen atmosphere, and adding an inhibitor into the reaction system, wherein the inhibitor is an aromatic alcohol compound. The invention provides a method for high selective preparation of aromatic aldehyde from the toluene compound, by adding the inhibitor into the reaction system, over oxidation of aromatic aldehyde in the catalytic oxidation process can be effectively suppressed, and the selectivity of aromatic aldehyde is significantly improved.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing aromatic aldehydes with high selectivity from toluene compounds. 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 Daily spices with aromas such as , camellia, etc., the aroma is gentle, delicate and elegant, and the amount used in spices accounts for 20%. [0003] 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/36C07C47/542C07C47/575C07C47/54C07C47/55
CPCC07C45/36C07C47/542C07C47/575C07C47/54C07C47/55
Inventor 李浩然袁浩然李观兵李景波汪玲瑶毛建拥陈志荣
Owner ZHEJIANG UNIV
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