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Application of monatomic catalyst in catalytic hydrogenation of lignin to aromatic compounds

A technology for catalytic hydrogenation of aromatic compounds, applied in the direction of catalyst activation/preparation, preparation of organic compounds, catalysts, etc., can solve problems such as harsh reaction conditions, poor atom economy, and difficulty in control, and achieve low cost, reduce pollution, and avoid Effects of Environmental Pollution Problems

Active Publication Date: 2019-04-19
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

Based on this, under the action of noble metal catalysts, lignin conversion is difficult to control in the cleavage step of aryl ether bonds, often accompanied by reactions such as hydrogenation of benzene rings, resulting in mixed products of phenols and alkanes, resulting in poor atom economy.
According to the research results of the literature, most of the currently reported hydrodepolymerization and oxidative depolymerization of lignin use noble metals such as Pd and Pt as catalysts, and the reaction conditions are relatively harsh, usually requiring additional acid or alkali, which causes serious pollution to the environment.

Method used

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  • Application of monatomic catalyst in catalytic hydrogenation of lignin to aromatic compounds
  • Application of monatomic catalyst in catalytic hydrogenation of lignin to aromatic compounds
  • Application of monatomic catalyst in catalytic hydrogenation of lignin to aromatic compounds

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Experimental program
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Effect test

Embodiment 1

[0021] monatomic M 1 / MoS 2 The specific preparation method of the catalyst (M=Fe, Ni, Ru, Rh, Pd, Pt, Ir) is as follows:

[0022] Monatomic Ni 1 / MoS 2 Preparation: Add 0.32g of ammonium molybdate tetrahydrate and 0.12g of sulfur powder into 57mL of oleylamine and stir at room temperature for 10min, then add 0.0145g of NiCl 3 ·6H 2 A solution of O fully dissolved in 3 mL of water was added to the above solution, stirred at room temperature for 1 h, then transferred to a 100 mL stainless steel reactor, and heated to 220 °C for 48 h. Then centrifuged and filtered, washed several times with ethanol and cyclohexane until the ligand oleylamine on the surface of the catalyst was washed off to obtain a black solid, and the collected black solid was vacuum-dried for 10 hours.

[0023] Fe 1 , Ru 1 , Rh 1 ,Pd 1 ,Pt 1 ,Ir 1 / MoS 2 Preparation: similar to Ni 1 / MoS 2 The preparation process, respectively, with 0.014gFeCl 3 ·6H 2 O, 0.0065g RuCl 3 ·H 2 O,0.0048g PdCl 2 ...

Embodiment 2-22

[0027] Example 2-22 Single atom M 1 / MoS 2 The catalyst catalyzes the depolymerization reaction of the lignin model molecule 2-(2-methoxyphenoxy)-1-phenylethanol: 100mg lignin model molecule is mixed with single-atom M / MoS 2Dissolve 20 mg of the catalyst in 30 mL of methanol, replace with hydrogen six times, seal the reaction vessel at 0.7 MPa and raise the temperature to 150°C-240°C, and carry out stirring reaction at 750 rpm for 4h-12h. After the reaction was completed, the temperature was lowered to room temperature, and the supernatant was filtered and then sampled for analysis. Qualitative analysis of the product was carried out by GC-MS technology and standard sample control, and quantitative analysis was realized by gas chromatography internal standard method. The reaction results are shown in Table 1.

[0028] Table 1 Single atom M under different conditions 1 / MoS 2 Catalysts and Nanocatalysts M / MoS 2 Catalytic depolymerization of lignin model molecule 2-(2-meth...

Embodiment 23-29

[0032] Ir 1 / MoS 2 Catalytic depolymerization of lignin model molecule 2-(2-methoxyphenoxy)-1-phenylethanol under different conditions: a certain mass of lignin model molecule was mixed with single-atom catalyst Ir in a reactor 1 / MoS 2 Dissolve in 30mL of different solvents respectively, replace with hydrogen for five times, fill with hydrogen to set pressure, raise the temperature of the reactor to 240°C, and carry out stirring reaction at 750 rpm for 10h. After the reaction was completed, the temperature was lowered to room temperature, and the supernatant was filtered and then sampled for analysis. Qualitative analysis of the product was achieved by GC-MS coupled technology and standard sample control, and quantitative analysis was realized by gas chromatography internal standard method. The reaction results are shown in Table 2.

[0033] Table 2 Single atom catalyst Ir under different conditions 1 / MoS 2 Catalytic depolymerization of lignin model molecule 2-(2-metho...

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Abstract

The invention relates to selective depolymerization of lignin hydrogenation, in particular to application of a monatomic catalyst in the catalytic hydrogenation of lignin to an aromatic compound. According to the method, a plurality of beta-O-4 model molecules and organic lignin, lignosulfonate and alkali lignin are used as raw materials, and the aromatic compound is obtained by highly selective cracking of an aryl ether bond in the hydrogen atmosphere of 150-240 DEG C and 0.7-3.0 MPa. The conversion rate of the beta-O-4 model molecules reaches up to 99%, the yield of guaiacol reaches up to 93%, and the yield of styrene reaches up to 65%. When different lignins are used as the raw materials for conversion, the yield of aromatic bio-oil is 38-70%. Renewable natural biomass is as the raw material, and the raw material is cheap and has a wide source; there is no need to use inorganic acid and alkali in the reaction process, and a lot of alkali lye by traditional lignin catalysis is avoided; and the reaction condition is mild, activity and selectivity are high, and the reaction process is environmentally-friendly.

Description

technical field [0001] The invention relates to the preparation of aromatic compounds by depolymerization of lignin, specifically a single-atom catalyst M 1 / MoS 2 A catalyst (M=Fe, Ni, Ru, Rh, Pd, Pt, Ir) catalyzes a method for preparing aromatic compounds by cracking lignin resources. Background technique [0002] Biomass is environmentally friendly and renewable, and can achieve CO 2 It is the world's largest and only energy material that can be converted into liquid hydrocarbons. The preparation of liquid fuels and chemicals from biomass is of great significance for solving the shortage of fossil resources and uneven regional distribution, reducing environmental pollution, and achieving sustainable economic development. [0003] Lignin is an important part of biomass resources, accounting for 15-30% of plant dry weight, and is the only renewable carbon resource that can provide aromatic chemicals in nature. At present, less than 2% of the lignin produced in the paper...

Claims

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Application Information

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IPC IPC(8): B01J27/051B01J37/10B01J37/16C07C1/20C07C15/073C07C15/46C07C41/26C07C43/23C07C41/18C07C43/205
CPCC07C1/20C07C41/18C07C41/26B01J27/051B01J27/0515B01J37/10B01J37/16C07C2527/051B01J35/23C07C15/073C07C15/46C07C43/23C07C43/205
Inventor 李昌志季建伟代弢王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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