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Application of a Single Atom Catalyst in Catalytic Hydrogenation of Lignin to Aromatic Compounds

A technology for aromatic compounds and aromatic compounds, applied in catalyst activation/preparation, preparation of organic compounds, catalysts, etc., can solve the problems of harsh reaction conditions, poor atom economy, environmental pollution, etc., achieve low cost, reduce pollution, avoid Effects of environmental pollution problems

Active Publication Date: 2022-06-24
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 a Single Atom Catalyst in Catalytic Hydrogenation of Lignin to Aromatic Compounds
  • Application of a Single Atom Catalyst in Catalytic Hydrogenation of Lignin to Aromatic Compounds
  • Application of a Single Atom Catalyst in Catalytic Hydrogenation of Lignin to Aromatic Compounds

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Experimental program
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Effect test

Embodiment 1

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

[0022] Monoatomic Ni 1 / MoS 2 Preparation: 0.32 g of ammonium molybdate tetrahydrate, 0.12 g of sulfur powder were added to 57 mL of oleylamine and stirred at room temperature for 10 min, followed by 0.0145 g 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 reaction kettle, and heated to 220 °C for 48 h. Then, centrifugal filtration, washing with ethanol and cyclohexane for several times, until the ligand oleylamine on the catalyst surface was washed away 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 of 0.014g FeCl was used 3 ·6H 2 O, 0.0065g RuCl 3 ·H 2 O, ...

Embodiment 2-22

[0027] Example 2-22 Single Atom M 1 / MoS 2 The catalyst catalyzes the depolymerization of the lignin model molecule 2-(2-methoxyphenoxy)-1-phenylethanol: 100 mg of the lignin model molecule was mixed with monoatomic M / MoS in a reaction kettle 220 mg of the catalyst was dissolved in 30 mL of methanol, replaced with hydrogen for six times, and the reactor was sealed at 0.7 MPa and heated to 150°C-240°C, and the reaction was stirred at a speed of 750 rpm for 4h-12h. After the reaction was completed, the temperature was lowered to room temperature, and the supernatant was filtered and sampled for analysis. The qualitative analysis of the product was achieved by GC-MS combined technology and standard sample control, and the quantitative analysis was achieved 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 results of depoly...

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 combined with the single-atom catalyst Ir in a reactor 1 / MoS 2 They were dissolved in 30 mL of different solvents, replaced with hydrogen for five times, and then filled with hydrogen to the set pressure. After the reaction was completed, the temperature was lowered to room temperature, and the supernatant was filtered and sampled for analysis. The qualitative analysis of the product was achieved by GC-MS combined technology and standard sample control, and the quantitative analysis was achieved 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 results of depolymerization of lignin model molecule 2-(2-methoxyphenoxy)-1-phenylethanol

[0034]

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Abstract

The present invention relates to the selective depolymerization of lignin hydrogenation, specifically the application of a single-atom catalyst in catalytic hydrogenation of lignin to aromatic compounds; the method uses various β-O-4 model molecules and organic lignin, Lignosulfonate and alkali lignin are used as raw materials to achieve highly selective cleavage of aromatic ether bonds at 150°C-240°C and a hydrogen atmosphere of 0.7-3.0MPa to obtain aromatic compounds. The conversion rate of β-O-4 model molecule is up to 99%, the yield of guaiacol is up to 93%, and the yield of styrene is up to 65%. When different lignins are used as raw materials, the yield of aromatic bio-oil is 38‑70%. The invention uses renewable natural biomass as a raw material, which is cheap and has a wide range of sources; the reaction process does not require the use of inorganic acids and alkalis, and avoids the production of a large amount of lye catalyzed by traditional lignin; it has mild reaction conditions, high activity and selectivity, and high reaction efficiency. The process environment is friendly and so on.

Description

technical field [0001] The present invention relates to lignin depolymerization to prepare aromatic compounds, specifically a single-atom catalyst M 1 / MoS 2 A method for preparing aromatic compounds by catalyzing the cracking of lignin resources by catalysts (M=Fe, Ni, Ru, Rh, Pd, Pt, Ir). 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. Using biomass as raw material to prepare liquid fuels and chemicals 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 the dry weight of plants, and it is the only renewable carbon resource in nature that can provide aromatic chemicals. At present, less than 2% of the ligni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): B01J27/051B01J37/10B01J37/16C07C1/20C07C15/073C07C15/46C07C41/26C07C43/23C07C41/18C07C43/205
CPCC07C1/20C07C41/18C07C41/26B01J27/051B01J27/0515B01J35/0013B01J37/10B01J37/16C07C2527/051C07C15/073C07C15/46C07C43/23C07C43/205
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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