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A kind of method that catalytic conversion veratrol is veratraldehyde

A technology for catalytic conversion and veratrol, which is applied in the fields of oxidative preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of rigidity affecting catalytic activity and catalytic selectivity, and achieve the effect of improving conversion rate and easy process implementation

Active Publication Date: 2018-10-02
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

The rigidity of the double bond in the molecular structure of the Salen-porphyrin complex affects its catalytic activity and catalytic selectivity. The reduced Salen-porphyrin complex of the present invention eliminates the double bond, greatly improving its catalytic activity and catalytic selectivity nature, using oxygen as an oxidant, is a new method for converting veratrol into veratraldehyde; no relevant technical reports have been seen yet

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Embodiment 1: catalytic conversion of veratrol is the technique of veratraldehyde, concrete operations are as follows:

[0013] (1) Preparation of Salen-porphyrin complex:

[0014] A. Synthesis of 5,10,15-triphenyl-20-p-hydroxyphenylporphyrin (HPTPP)

[0015] Prepared by existing methods, reference literature: Ji Liangnian, Qin Xia, Huang Jinwang. Synthesis and Characterization of New Tailed Metalloporphyrin Complexes. Journal of Sun Yat-Sen University (Natural Science Edition), 1993, 32 (2): 1 -7.

[0016] Dissolve 2.3g (0.019mol) of p-hydroxybenzaldehyde and 5.7mL (0.057mol) of benzaldehyde in 300ml of propionic acid; add 5.1g of freshly distilled pyrrole to the dropping funnel; mechanically stir and heat to reflux at a temperature of 141°C , add pyrrole dropwise, drop it for 2 minutes, control the temperature at 131°C and continue the reaction for 30 minutes. After the reaction mixture is left to stand for 12 hours, use vacuum rotary evaporation to remove two-third...

Embodiment 2

[0029] Embodiment 2: catalytic conversion of veratrol is the technique of veratraldehyde, concrete operation is as follows:

[0030] (1) The preparation method of the reduced Salen-porphyrin complex is the same as step (1) of Example 1;

[0031] (2) Method for catalytically converting veratrol into veratraldehyde

[0032] In the presence of the reduced salen-porphyrin complex, the veratrol was treated. When the veratrol was treated, 25 mL of deionized water was added to the veratrol 1 mmol, and the catalyst reduced salen-porphyrin was added at the same time. Complexes and O 2 , the amount of reduced Salen-porphyrin complex is 0.01% of the quality of veratrol, O 2The pressure is 0.2MPa, the pH is neutral, the treatment temperature is controlled at 50°C, and the time is 2h; the conversion rate of veratrol is 80%. Using this process, the conversion rate of veratrol is higher than that of the non-reduced salen-porphyrin complex 25 %. Oxygen consumption is 50%. Using this proce...

Embodiment 3

[0033] Embodiment 3: Catalytic conversion veratrol is the technique of veratraldehyde, concrete operation is as follows:

[0034] (1) The preparation method of the reduced Salen-porphyrin complex is the same as the example 1 step (1);

[0035] (2) Catalytic conversion of veratrol into veratraldehyde by reduced Salen-porphyrin complex

[0036] Veratrol was treated in the presence of reduced Salen-porphyrin complex. When veratrol is processed, 35 mL of deionized water is added to 1 mmol of veratrol, and the catalyst-reduced Salen-porphyrin complex and O 2 , the reduced Salen-porphyrin complex dosage is 0.03% of the veratrol quality, O 2 The pressure is 0.3MPa, the pH is neutral, the treatment temperature is controlled at 60°C, and the time is 3h; the conversion rate of veratrol is 96%. Using this process, the conversion rate of veratrol is 30% higher than that of the non-reduced Salen-porphyrin complex. %. Oxygen consumption is 58%. Using this process, oxygen consumption is ...

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Abstract

The invention discloses a method for catalytically converting veratryl alcohol into veratraldehyde, and belongs to the technical field of converting the veratryl alcohol into the veratraldehyde. The method is characterized in that the veratryl alcohol is treated under the condition that a reduction salen-porphyrin complex exists; oxygen and water in certain pressure can be added while the veratryl alcohol is treated according to a technology of catalytically converting the veratryl alcohol into the veratraldehyde, and the treatment temperature, the treatment pH (Potential of Hydrogen) and the treatment time can be controlled. According to the method for catalytically converting the veratryl alcohol into the veratraldehyde, disclosed by the invention, a green catalytic oxidation technology is adopted, the veratryl alcohol is exclusively converted into the veratraldehyde, and the conversion rate of the veratryl alcohol is remarkably increased.

Description

technical field [0001] The invention relates to a method for catalytically converting veratrol into veratraldehyde, in particular to a process for improving the conversion of veratrol into veratraldehyde by a reduced salen-porphyrin complex. 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C47/575C07C45/29
CPCC07C45/29C07C47/575
Inventor 周学飞
Owner KUNMING UNIV OF SCI & TECH
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