Method for preparing p-methoxybenzaldehyde perfume in presence of metalloporphyrin through catalytic oxidation of p-methoxytoluene

A technology of p-methoxybenzaldehyde and p-methoxytoluene, which is applied in the field of preparing p-methoxybenzaldehyde fragrance by catalytic oxidation of p-methoxytoluene by metalloporphyrins, can solve the problem of low catalyst activity and selectivity, increased energy Consumption and operational risk, large amount of metal salt catalyst, etc., to achieve the effect of reducing resource consumption and operating costs, easing reaction conditions, reducing energy consumption and operating costs

Inactive Publication Date: 2014-04-02
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] (1) The amount of metal salt catalyst is large (5000ppm), and the cost of separation and recovery is high, the energy consumption is large, the discharge of three wastes is large, and the environmental pollution is serious;
[0008] (2) The activity and selectivity of the catalyst are low, the reaction process is not easy to control, and there are many by-products;
[0009] (3) The reaction conditions of high temperature and high pressure are harsh, which greatly increases the energy consumption and the risk of operation

Method used

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  • Method for preparing p-methoxybenzaldehyde perfume in presence of metalloporphyrin through catalytic oxidation of p-methoxytoluene
  • Method for preparing p-methoxybenzaldehyde perfume in presence of metalloporphyrin through catalytic oxidation of p-methoxytoluene

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take 8.2×10 -4 g tetrakis chloride-(p-methoxyphenyl)iron porphyrin (i.e. R in the formula (II) 21 =R 22 = H, R 23 =OCH 3 , X=Cl,M 2 =Fe), 2.4g of p-methoxytoluene and 0.1619g of N-hydroxyphthalimide were added to a 100mL autoclave, 17.5mL of acetonitrile was added, and oxygen at a pressure of 0.4MPa was introduced, and the temperature was controlled in a water bath for 70 It was reacted at ℃ for 4h, and the reacted mixture was distilled under reduced pressure, and then purified by column chromatography to obtain p-methoxybenzaldehyde. As detected by high performance liquid chromatography, the conversion rate of p-methoxytoluene was 48.5%, the selectivity of p-methoxybenzaldehyde was 46.3%, and the yield of p-methoxybenzaldehyde was 22.5%.

Embodiment 2

[0030] Take 1.7×10 -3 g chloride tetra-(p-nitrophenyl)iron porphyrin (i.e. R in the formula (II) 21 =R 22 = H, R 23 =NO 2 , X=Cl,M 2 =Fe), 2.4g of p-methoxytoluene and 0.1619g of N-hydroxyphthalimide were added to a 100mL autoclave, 17.5mL of acetonitrile was added, and oxygen at a pressure of 0.2MPa was introduced, and the temperature was controlled in a water bath for 70 It was reacted at ℃ for 4h, and the reacted mixture was distilled under reduced pressure, and then purified by column chromatography to obtain p-methoxybenzaldehyde. As detected by high performance liquid chromatography, the conversion rate of p-methoxytoluene was 38.2%, the selectivity of p-methoxybenzaldehyde was 38.7%, and the yield of p-methoxybenzaldehyde was 14.8%.

Embodiment 3

[0032] Take 1.3×10 -3 g tetrakis chloride-(p-methoxyphenyl)iron porphyrin (i.e. R in the formula (II) 21 =R 22 = H, R 23 =Cl,X=Cl,M 2 =Fe), 2.4g of p-methoxytoluene and 0.0971g of N-hydroxyphthalimide were added to a 100mL autoclave, 17.5mL of acetonitrile was added, and oxygen at a pressure of 0.2MPa was introduced, and the temperature was controlled in a water bath at 65 It was reacted at ℃ for 10 h, and the reacted mixture was distilled under reduced pressure, and then purified by column chromatography to obtain p-methoxybenzaldehyde. As detected by high performance liquid chromatography, the conversion rate of p-methoxytoluene was 37.0%, the selectivity of p-methoxybenzaldehyde was 36.2%, and the yield of p-methoxybenzaldehyde was 13.4%.

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Abstract

The invention relates to a method for preparing p-methoxybenzaldehyde perfume in presence of metalloporphyrin through catalytic oxidation of p-methoxytoluene. The method comprises the steps of: by taking metalloporphyrin with the concentration of 10-100ppm as a catalyst, N-hydroxyphthalimide as a free radical initiator and, introducing oxygen under 0.1-1.0Mpa and reacting for 1-12h at 60-100 DEG C in an acetonitrile solvent to obtain p-methoxybenzaldehyde, wherein the molar ratio of N-hydroxyphthalimide to p-methoxytoluene is (0.01-0.1):1. The method has the advantages that the consumption of the catalyst is extremely low, separation and recovery are not needed, the catalyst is higher in activity and selectivity, and a reaction condition is mild. According to the method provided by the invention, not only can resources be utilized and saved effectively, but also environmental pollution is reduced and the purpose of reducing energy consumption is achieved to further realize energy saving and emission reduction in an all-round way, and thus, the method has a wide application prospect in the industry.

Description

technical field [0001] The invention relates to a method for preparing aromatic aldehyde fragrance, in particular to a method for preparing p-methoxybenzaldehyde fragrance by catalytic oxidation of p-methoxytoluene by metalloporphyrin. Background technique [0002] p-Methoxybenzaldehyde, also known as anisaldehyde and anisaldehyde, is a spice with high economic value and an important organic synthesis intermediate, widely used in medicine, pesticides, flavors and fragrances and other fields. Although there are many methods for preparing p-methoxybenzaldehyde from p-methoxytoluene at present, the liquid-phase catalytic oxidation method is relatively superior. [0003] Nobumasa Krtajima et al. (Bulletin of the Chemical Society of Japan, 1988, 61:967-971) reported a metal salt-catalyzed oxidation of p-methoxytoluene to prepare p-methoxybenzaldehyde. The method uses acetic acid as a solvent, cobalt acetate, chromium acetate, and cerium acetate as a composite catalyst, and under...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/575C07C45/36B01J31/22
CPCC07C45/36B01J31/183B01J2231/70B01J2531/0205B01J2531/025C07C47/575
Inventor 佘远斌杨柳
Owner BEIJING UNIV OF TECH
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