Method for preparing coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol by taking lignocellulose as raw material

A technology of lignocellulose and coniferyl alcohol, which is applied in ether preparation, ether separation/purification, organic chemistry and other directions, can solve the problems of unfavorable separation and utilization, complex products, high cost, and achieve resource utilization and high-value utilization, A wide range of sources and high value-added effects

Active Publication Date: 2020-06-30
BEIJING FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these studies all use noble metals as catalysts, and their cost is relatively high.
At the same time, the obtained products are more complex, which is not conducive to separation and utilization

Method used

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  • Method for preparing coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol by taking lignocellulose as raw material
  • Method for preparing coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol by taking lignocellulose as raw material
  • Method for preparing coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol by taking lignocellulose as raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] After the birch wood is pulverized to 20-60 meshes, after extracting with toluene and ethanol (2:1, v:v) at 105°C for 12 hours, dewaxed birch wood powder is obtained, and 1 g of the dewaxed birch wood powder is 、MoO 2 / C and methanol in a mass ratio of 1:0.05:20 are added to the high-pressure Parr reactor, and then 3MPa hydrogen is introduced and heated to the reaction temperature (260°C) for 4 hours of reaction at a stirring speed of 800rpm. After the reaction, the temperature is naturally lowered to At room temperature, the pressure was released to normal pressure, and filtered through an organic membrane to obtain a solid residue and a liquid product. The liquid product is extracted with 30mL of dichloromethane, spin-dried by a rotary evaporator at 0.05atm and 45°C, then dissolved and filtered in dichloromethane containing 0.1mg / mL n-tetradecane internal standard, and then enters the GC (gas chromatograph) , GC-MS (gas chromatography-mass spectrometry) for qualitati...

Embodiment 2

[0047] Same as Example 1, only the reaction solvent of the step is replaced by ethanol, isopropanol or water. Monomer yield, selectivity and separation yield are shown in Table 2, image 3 shown; the table shows MoO in 2 different solvents 2 / C catalyzed hydrogenation results of birch wood flour. From Table 2, image 3 It can be seen from the data that under the organic solvent system, its catalytic degradation lignin monomer yield and the selectivity and separation yield of coniferyl alcohol, sinapyl alcohol and their derivatives have high yields. In this system, lignin cannot be degraded well.

[0048] Table 2 MoO in different solvents 2 Hydrogenation results of / C catalyzed birch wood flour

[0049] solvent Monomer Yield (wt%) Selectivity (wt%) Separation yield (wt%) ethanol 43.6 92 18 Isopropanol 37.8 91 16 water 9.3 - -

Embodiment 3

[0051] Same as Example 1, only the catalyst is recycled, that is, the catalyst collected after the last reaction is activated at high temperature and used. The lignin monomer yield, selectivity and separation yield are shown in Table 3, and Table 3 shows the concentration of MoO in different solvents. 2 / C catalyzed hydrogenation results of birch wood flour. From the data in Table 3, it can be seen that MoO 2 After five cycles of the / C catalyst, the yield of lignin monomer degradation can still reach 43.6%, and the selectivity can still reach more than 90%. This shows that the catalyst has high stability.

[0052] Table 3 MoO in different solvents 2 / C Catalyzed Hydrogenation Results of Birch Wood Flour

[0053]

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Abstract

The invention relates to a method for preparing coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol by using lignocellulose as a raw material. The method comprises the following steps: adding a lignocellulose raw material, a catalyst and a reaction solvent into a high-pressure reaction kettle, introducing hydrogen, heating to a reaction temperature, and carrying out a stirring reaction; after the reaction is finished, naturally cooling to room temperature, releasing pressure to normal pressure, and filtering to obtain solid residues and a liquid product;spin-drying the obtained liquid product, dissolving with dichloromethane, and extracting to obtain a lignin oil product containing coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol; and carrying out chromatographic column separation on the obtained lignin oil product to respectively obtain coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol. According to the invention, lignin is converted into coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol in a high-yield and high-selectivity mode through a one-pot method, so that coniferyl alcohol, sinapyl alcohol and derivatives of coniferyl alcohol and sinapyl alcohol can be efficiently prepared and separated, and resource utilization and high-value utilization of lignin are achieved.

Description

technical field [0001] The invention relates to a method for preparing coniferyl alcohol, sinapyl alcohol and derivatives thereof by using lignocellulose as a raw material, and belongs to the technical field of biochemical industry. Background technique [0002] Coniferyl alcohol, also known as 4-hydroxy-3-methoxycinnamyl alcohol, belongs to phenolic compounds and exists in coniferous and broad-leaved woods. Coniferyl alcohol is not only one of the constituent monomers of plant cell walls, but also widely used in other aspects. For example, coniferyl alcohol is an important intermediate in the synthesis of some natural products such as the anti-hepatitis drug silymarin. The synthetic method of current coniferyl alcohol mainly comprises two kinds: 1) take coniferyl acid as raw material, after making acid chloride, esterification, reduction obtains coniferyl alcohol. 2) Taking coniferyl acid as a raw material, undergoing esterification, acetylation, and reduction to obtain co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/01C07C41/34C07C43/23
CPCC07C41/01C07C41/34C07C43/23
Inventor 宋国勇肖领平孙建奎王水众
Owner BEIJING FORESTRY UNIVERSITY
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