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Technology for converting veratryl alcohol into veratraldehyde through catalysis

A technology of catalytic conversion and veratrol, applied in the directions of oxidation preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of difficult preparation, application limitation, and high cost, and achieve the effects of reducing pharmaceutical consumption, reducing pharmaceutical consumption, and reducing dosage.

Inactive Publication Date: 2015-11-18
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As an enzyme-like catalyst for catalytic oxidation, metalloporphyrins exhibit high catalytic activity, but their application is limited due to their high cost and difficulty in preparing chiral complexes.
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Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0011] Example 1: The process of catalytically converting veratrol to veratraldehyde, the specific operation is as follows:

[0012] (1) Preparation of Salen-porphyrin complex:

[0013] A. Synthesis of 5,10,15-triphenyl-20-p-hydroxyphenylporphyrin (HPTPP)

[0014] Prepared by existing methods, refer to literature: Ji Liangnian, Qin Xia, Huang Jinwang. Synthesis and characterization of novel tailed metal porphyrin complexes. Journal of Sun Yat-sen University (Natural Science Edition), 1993, 32(2):1 -7.

[0015] Dissolve 2.3g (0.019mol) p-hydroxybenzaldehyde and 5.7mL (0.057mol) benzaldehyde in 300ml propionic acid. Add 5.1 g of freshly distilled pyrrole into the dropping funnel. Stir mechanically and heat to reflux at a temperature of 141°C. Add pyrrole dropwise for 2 minutes. The temperature is controlled at 131°C to continue the reaction for 30 minutes. After the reaction mixture is allowed to stand for 12 hours, vacuum rotary evaporation is used to remove two thirds of the propane...

Embodiment 2

[0026] Embodiment 2: The process of catalytically converting veratrol to veratraldehyde, the specific operation is as follows:

[0027] (1) The preparation method of the Salen-porphyrin complex is the same as the step (1) of Example 1;

[0028] (2) Method of catalytically converting veratrol to veratraldehyde

[0029] In the presence of bipyridine and Salen-porphyrin complex, the veratrol is processed. When veratrol is processed, 25mL of deionized water is added to 0.75mmol of veratrol, and the catalyst Salen-porphyrin is added at the same time Complex, 2,2'-bipyridine and H 2 O 2 , The amount of Salen-porphyrin complex is 0.075mmol, the molar ratio of 2,2’-bipyridine to Salen-porphyrin complex is 3:1, and the mass percentage concentration is 30% H 2 O 2 0.1mL, pH=10, the treatment temperature is controlled at 60℃, and the time is 4h; the veratrol conversion rate is 75%. With this process, the veratrol conversion rate is higher than that of the salen complex and the porphyrin complex...

Embodiment 3

[0030] Example 3: The process of catalytically converting veratrol to veratraldehyde, the specific operation is as follows:

[0031] (1) The preparation method of Salen-porphyrin complex is the same as step (1) of Example 1;

[0032] (2) Method for catalytic conversion of Veratrol to Veratraldehyde by Salen-porphyrin complex

[0033] In the presence of bipyridine and Salen-porphyrin complexes, veratrol is treated. When treating veratrol, add 35 mL of deionized water to 1 mmol of veratrol, and add the catalyst Salen-porphyrin complex, 2,2’-bipyridine and H 2 O 2 , The amount of Salen-porphyrin complex is 0.10mmol, the molar ratio of 2,2’-bipyridine to Salen-porphyrin complex is 5:1, and the mass percentage concentration is 30% H 2 O 2 0.15mL, pH=12, the treatment temperature is controlled at 80℃, and the time is 6h; the veratrol conversion rate is 93%. With this process, the veratrol conversion rate is higher than that of the single-site complexes of salen complex and porphyrin comple...

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Abstract

The invention relates to a technology for converting veratryl alcohol into veratraldehyde through catalysis, and belongs to the technical field of conversion of veratryl alcohol into veratraldehyde. According to the technology, veratryl alcohol is processed in the presence of dipyridyl and Salen-porphyrine complexes; H2O2 and water are added and processing temperature, pH and time are controlled when veratryl alcohol is processed with the technology for converting the veratryl alcohol into veratraldehyde through catalysis. The environment-friendly catalytic oxidation technology is adopted to specifically convert veratryl alcohol into veratraldehyde, and the conversion rate is higher.

Description

technical field [0001] The invention relates to a process for catalytically converting veratrol into veratraldehyde, which is an improved technique for catalytically oxidizing veratrol into veratraldehyde. Background technique [0002] The lignin oxidase catalyzes the oxidation of veratrol to obtain veratraldehyde, and adding a surfactant increases the yield of veratraldehyde. The use of biological treatment is undoubtedly an economical and effective means, but biological treatment is sensitive to environmental conditions, poor impact resistance and easy inactivation and other disadvantages. Therefore, scientists have developed high-efficiency chemical catalysis and highly selective biocatalytic enzyme-like (mimetic enzyme) compounds, which is another direct and effective new way to realize green chemistry. Compared with metalloporphyrin complex imitation enzyme catalyst, non-porphyrin metal complex M(salen)(M=metal,salen= N , N '-bis (salicylidene) ethane-1,2-diaminato) ...

Claims

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Application Information

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IPC IPC(8): C07C47/575C07C45/29
CPCC07C45/29C07C47/575
Inventor 周学飞高田田柳明星许燕妮
Owner KUNMING UNIV OF SCI & TECH
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