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A method for catalyzing the oxidative cracking of lignin model aryl ethers

An aryl ether and lignin technology, applied in chemical instruments and methods, preparation of organic compounds, catalysts for physical/chemical processes, etc., can solve the problems of poor oxidative bond cleavage selectivity, complex oxidant preparation, and few oxidative cracking reactions, etc. Achieve the effect of less catalyst dosage, good oxidative bond cleavage selectivity, and high selective oxidative cleavage

Active Publication Date: 2021-04-30
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been a lot of reports on the cracking of aryl ethers through hydrocracking, photodegradation or electrochemical degradation, but there are very few reports on their oxidative cracking reactions.
Larsen et al reported the use of Fe(III) complexes as a catalyst, air as an oxygen source, and the method of reflux in acetonitrile under normal pressure to oxidize benzyl phenyl ether; the conversion rate of raw material benzyl phenyl ether in this oxidation system is as high as 90 % or more, but the solvent acetonitrile in the system is oxidized at the same time, and by-products such as benzene epoxidation products phenols are produced in large quantities, and the selectivity of oxidative bond breaking is poor
Yan Ning et al. reported a nitrogen-containing graphene material (LCN) as a catalyst, tert-butyl hydroperoxide (TBHP) as an oxidant, and a water-phase oxidative cracking method of benzyl phenyl ether, reacting at 80 ° C for 24 h, benzyl The conversion rate of phenyl ether is 68%; but the preparation of oxidant used in the reaction is complicated and the consumption is large
[0004] It can be seen from previous studies that the oxidative cracking of aryl ethers is still in the exploratory stage, and it is of great research significance to develop a catalytic oxidation system with high efficiency and high bond-breaking selectivity.

Method used

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  • A method for catalyzing the oxidative cracking of lignin model aryl ethers

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Add 2.5mmol of benzyl phenyl ether, 0.125mmol of vanadyl sulfate, 0.125mmol of copper nitrate, and 2mL of ethylene glycol dimethyl ether into a 30mL reaction kettle, fill it with oxygen to 1.0MPa, and raise the temperature to 100°C under constant stirring. And kept for 10h, cooled to room temperature. Use the internal standard method to analyze by gas chromatography, and calculate the conversion rate of benzyl phenyl ether and the selectivity of the oxidative bond breaking product according to the following formula.

[0014] Conversion rate [mol%]=(A 0 -A) / A 0 ×100%

[0015] Selectivity [mol%] = B i / (A 0 -A)×100%

[0016] In the formula, A 0 Be the amount of substance [mol] that adds benzyl phenyl ether before the reaction, A is the amount of substance [mol] of benzyl phenyl ether after the reaction, B i It is the amount [mol] of substances that generate benzaldehyde, phenol, benzoic acid, and phenyl benzoate after the reaction. Bond breaking selectivity [mol%]...

Embodiment 2

[0019] Add 2.5mmol of benzyl phenyl ether, 0.075mmol of vanadyl sulfate, 0.075mmol of zinc nitrate, and 2mL of ethylene glycol dimethyl ether into a 30mL reaction kettle, fill it with oxygen to 1.0MPa, and raise the temperature to 120°C under constant stirring. And kept for 10h, cooled to room temperature. Carry out product analysis by embodiment 1 method;

[0020] The conversion rate of benzyl phenyl ether was calculated to be 82%, and the bond breaking selectivity was 80%.

Embodiment 3

[0022] Add 2.5mmol of phenylphenetole, 0.125mmol of vanadyl acetylacetonate, 0.125mmol of copper nitrate, and 2mL of acetic acid into a 30mL reaction kettle, fill it with oxygen to 1.5MPa, raise the temperature to 100°C under constant stirring, and keep it for 6h, then cool to room temperature. Carry out product analysis by embodiment 1 method;

[0023] The conversion rate of phenylphenetole was calculated to be 68%, and the bond breaking selectivity was 75%.

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Abstract

A method for catalyzing the oxidative cracking of lignin model aryl ethers, characterized in that: the method uses a simple inorganic vanadium oxide compound and a nitrate two-component as a composite catalyst system, and uses molecular oxygen as an oxygen source to catalyze the lignin model aryl ether. Oxidative cleavage of base ethers. In the method, the catalyst is simple, cheap and easy to obtain, the reaction conditions are mild, and the oxidative cracking efficiency is high, and the aryl ether in the lignin is efficiently cracked by using the catalytic oxidation method.

Description

technical field [0001] The invention relates to a method for effectively cracking lignin model aryl ether through catalytic oxidation. Specifically, a simple inorganic two-component composite catalyst is used as an oxygen source, and molecular oxygen is used as an oxygen source to efficiently catalyze the cracking of aryl ether in the oxidized lignin model under liquid phase and mild conditions. Background technique [0002] Biomass is abundant, widely sourced and renewable, and is a potential recyclable natural resource. Lignin is one of the three major components of plant biomass, and its content in plant biomass is about 15-30%. Because of its special structure and properties, lignin resources have great potential application value. Lignin is a rich source of natural and renewable bulk aromatic compounds. The development and utilization of lignin resources is of great significance for the preparation of high value-added aromatic compounds. Lignin itself is a highly cros...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C37/54C07C37/52C07C39/04B01J27/053B01J27/25B01J31/02B01J27/198
CPCB01J27/053B01J27/198B01J27/25B01J31/0208C07C37/52C07C37/54C07C39/04Y02P20/52
Inventor 徐杰马阳阳马继平夏飞高进苗虹
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI