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Method for preparing guaiacol by catalyzing efficient conversion of lignin through Lewis acid

A technology of guaiacol and Lewis acid, applied in chemical instruments and methods, preparation of organic compounds, preparation of ethers, etc., can solve the problems of difficulty in improving catalytic conversion of lignin, low reactivity, high heterogeneity, etc. To achieve the effect of easy separation, simple catalytic system and simple operation

Active Publication Date: 2021-07-13
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, lignin is composed of a large number of inert carbon-oxygen bonds and carbon-carbon bonds. Its high heterogeneity and low reactivity increase the difficulty of catalytic conversion of lignin.
At present, some catalytic methods, such as hydrogenation degradation, oxidative degradation, hydrolysis, etc., are widely used in the catalytic conversion of lignin to prepare small molecule aromatic compounds. However, the degradation products of the above methods are mainly a series of phenols, aromatic hydrocarbons and aromatic acids. Mixed products, guaiacol is often only one of these mixed products, and the yield is very low
If the above method is used to prepare guaiacol, it needs to go through complicated product separation and purification processes, which brings great challenges to the conversion of lignin industry into high value-added chemicals

Method used

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  • Method for preparing guaiacol by catalyzing efficient conversion of lignin through Lewis acid
  • Method for preparing guaiacol by catalyzing efficient conversion of lignin through Lewis acid
  • Method for preparing guaiacol by catalyzing efficient conversion of lignin through Lewis acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Preparation of eucalyptus organic lignin raw material

[0025] First, 50g of eucalyptus was placed in a 1000mL acid and alkali resistant reaction kettle containing 500mL of isopropanol aqueous solution (7:3, v / v). Then the reaction kettle was heated to 220° C. and kept at constant temperature for 1 h. Then it was cooled to room temperature, filtered, and the filter residue was washed with 70% isopropanol aqueous solution. The filtrates were combined and concentrated. Then slowly drop the concentrated solution into 10 times the volume of acid water with pH=2, centrifuge the precipitate, and finally freeze-dry to obtain the organic lignin. The two-dimensional NMR spectrum of the Eucalyptus organic lignin extracted and separated by the above method ( figure 1 ) It can be seen that the main constituent unit of the lignin is (A) β-O-4 ether bond structure; (B) resin alcohol structure; (C) phenylcoumarin structure (β-5 and α-O -4 linked); (I) p-hydroxycinnamyl alcohol...

Embodiment 2

[0030] (1) Preparation of eucalyptus organic lignin raw material

[0031] The extraction and separation of eucalyptus organic lignin is the same as in Example 1.

[0032] (2) Lignin conversion to prepare guaiacol reaction

[0033] Add 50 mg of eucalyptus organic lignin, 10 mg of ferric trifluoromethanesulfonate, 4 mL of methanol, and 10 μL of water into a 15 mL Teflon-lined reactor. Then the reaction vessel was sealed, and the air was exhausted and filled with argon to 0.1MPa. The reaction temperature was 270°C and kept for 24h. Cool to room temperature, collect the gas and centrifuge the reaction mixture, use GC-MS, liquid phase and NMR qualitative analysis of the liquid product, use GC to quantitatively analyze the liquid product, and obtain the ratio of the quality of guaiacol to the initial quality of lignin That is its yield.

[0034] (3) After the reaction, the liquid product only contains guaiacol, a lignin degradation monomer, and the yield is 13.5 wt%.

Embodiment 3

[0036] (1) Preparation of eucalyptus organic lignin raw material

[0037] The extraction and separation of eucalyptus organic lignin is the same as in Example 1.

[0038] (2) Lignin conversion to prepare guaiacol reaction

[0039] Add 50 mg of eucalyptus organic lignin, 5 mg of ferric trifluoromethanesulfonate, 4 mL of methanol, and 10 μL of water into a 15 mL Teflon-lined reactor. Then the reaction vessel was sealed, and the air was exhausted and filled with argon to 0.1MPa. The reaction temperature was 270°C and kept for 24h. Cool to room temperature, collect the gas and centrifuge the reaction mixture, use GC-MS, liquid phase and NMR qualitative analysis of the liquid product, use GC to quantitatively analyze the liquid product, and obtain the ratio of the quality of guaiacol to the initial quality of lignin That is its yield.

[0040] (3) After the reaction, the liquid product only contains guaiacol, a lignin degradation monomer, and the yield is 5.3 wt%.

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Abstract

The invention discloses a method for catalyzing conversion of lignin into guaiacol as a single chemical by lewis acid. According to the method, the lignin is catalyzed to be converted into the guaiacol in an inert atmosphere with lewis acid as a catalyst, and the guaiacol is the only liquid product. The lewis acid comprises at least one of iron trifluoromethanesulfonate, ytterbium trifluoromethanesulfonate and lanthanum trifluoromethanesulfonate. According to the method, the catalytic system is simple in composition and green, the liquid product yield is high, only guaiacol is a liquid product, and other residues are solids. The invention provides a new way for preparing the guaiacol, provides a new method for preparing high value-added platform molecules, especially important chemicals from a traditional fossil resource route, for oriented conversion of lignin, and also provides a new thought for resource utilization of lignin. The method is a green and sustainable lignin carbon resource catalytic conversion strategy, and the dependence of chemical industry on fossil resources can be reduced.

Description

technical field [0001] The invention belongs to the field of catalytic conversion of biomass into high value-added chemicals, and in particular relates to a method for preparing guaiacol by efficient conversion of Lewis acid catalyzed lignin. Background technique [0002] In the modern chemical industry, guaiacol is an important raw material for the synthesis of a variety of high value-added chemicals, such as spices (vanillin, veratraldehyde and eugenol), pesticides, drugs (guaiacol glyceryl ether, guaiac wood Potassium phenate, potassium guaiacol sulfonate, berberine, isoproterenol), plant growth regulators, etc. According to global market research, the demand for these high value-added chemicals is increasing year by year. Among them, the annual demand for guaiacol glyceryl ether, vanillin, and eugenol is about 37,000 tons / year, 16,000 tons / year, and 7,300 tons / year. These three chemicals are mainly synthesized from guaiacol . Therefore, the annual global market demand...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/01C07C41/18C07C43/23C08H7/00
CPCC07C41/01C07C41/18C08H6/00C07C43/23
Inventor 孟庆磊沈晓骏韩布兴严江刘会贞
Owner INST OF CHEM CHINESE ACAD OF SCI
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