Method for preparing alkylphenol and alkyl diphenol from lignin oil

A technology for alkyl phenols and alkyl diphenols, which is applied in the field of preparation of alkyl phenols and alkyl diphenols from lignin oil, can solve the problems of product added value reduction, product quality yield reduction, product quality yield reduction, etc., and achieve Cost-saving, wide-ranging sources, and low-cost effects

Pending Publication Date: 2019-06-28
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
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  • Application Information

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Problems solved by technology

[0004] At present, the most research is on the extraction of lignin oil, and the production of phenol by the depropylation reaction of propyl phenol has also been studied. Although the process of deoxygenation and hydrogenation of lignin oil to phenylphenol mixture has been studied, the yield is not high.
Chinese patent (CN106753549A) uses Pd or Pt / Nb 2 o 5 -SiO 2 As a catalyst, lignin is first depolymerized into light phenolic compounds, and then hydrodeoxygenated to prepare hydrocarbon compounds, but the products are mainly cycloalkanes and alkylcycloalkanes, resulting in ring hydrogenation of benzene rings and oxygen-containing functional groups The disappearance of its products is not high
Chinese patent (CN 104744204A) uses a dual-active component catalyst, uses water as a solvent, and catalyzes lignin hydrodeoxygenation in a hydrogen atmosphere at 180~350ºC to obtain C 6 -C 9 Aromatic hydrocarbons, but the oxygen-containing functional group still cannot be retained in the product, resulting in a decrease in the mass yield of the product and a decrease in the added value of the product
Although the above method can depolymerize and hydrogenate lignin to obtain aromatic hydrocarbons and cycloalkanes, it loses oxygen-containing functional groups, the added value of the product is low, and the product quality yield decreases

Method used

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  • Method for preparing alkylphenol and alkyl diphenol from lignin oil
  • Method for preparing alkylphenol and alkyl diphenol from lignin oil
  • Method for preparing alkylphenol and alkyl diphenol from lignin oil

Examples

Experimental program
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Effect test

Embodiment 1-14

[0025] The preparation steps of lignin oil are as follows: In a 50mL small autoclave, add 0.1g of metal catalyst supported by activated carbon, 1.0g of lignin or lignin-containing biomass raw material and 20mL of methanol, under hydrogen partial pressure of 2.5~3.5MPa, temperature for 150 o C~250 o C under the condition of reaction for 2 to 5 hours. The product was rotary evaporated to remove the methanol solvent to obtain lignin oil and its components were analyzed. The reaction product was qualitatively analyzed by gas chromatography-mass chromatography (GC-MS Agilent 7890A-5975C) and quantitatively analyzed by gas chromatography (GC Agilent 7890A). HP-5 chromatographic column was used, and the temperature program temperature condition of the chromatographic column was: 50 o C maintain 10mins, with 10 o C / min heating rate increased to 250 o C, and at 250 o C maintained for 5mins.

[0026] Wherein, the calculation formula of yield is: mass yield of lignin oil=(quality o...

Embodiment 15-46

[0033] The steps of the batch reactor are as follows: 0.1g lignin oil (the product of Example 1-14), 0.05g catalyst and 20mL deionized water are added to a 50mL batch reactor, and the hydrogen partial pressure is 4~6MPa, the temperature for 250 o C~400 o C under the conditions of reaction for 5 to 10 hours. The reaction product was qualitatively analyzed by gas chromatography-mass chromatography (GC-MS Agilent 7890A-5975C) and quantitatively analyzed by gas chromatography (GC Agilent 7890A). HP-5 chromatographic column was used, and the temperature program temperature condition of the chromatographic column was: 50 o C maintain 10mins, with 10 o C / min heating rate increased to 250 o C, and at 250 o C maintained for 5mins. The analysis results are shown in Table 2.

[0034] Wherein, the calculation formula of yield is: mass yield of alkylphenol mixture (%)=(mass of alkylphenol mixture in product / mass of lignin oil before reaction)´100%.

[0035] The preparation of niobiu...

Embodiment 47-77

[0047] Examples 47-77

[0048] The steps of continuous fixed bed are as follows: 0.075g catalyst, the feed rate of lignin oil (the product of embodiment 1-14) is 3mmol / h, and hydrogen flow rate is 20-50mL / h, and temperature is 250 o C~450 o c. The reaction product was qualitatively analyzed by gas chromatography-mass chromatography (GC-MS Agilent 7890A-5975C) and quantitatively analyzed by gas chromatography (GC Agilent 7890A). HP-5 chromatographic column was used, and the temperature program temperature condition of the chromatographic column was: 50 o C maintain 10mins, with 10 o C / min heating rate increased to 250 o C, and at 250 o C maintained for 5mins. The analysis results are shown in Table 3.

[0049] Wherein, the calculation formula of yield is: mass yield of alkylphenol mixture (%)=(mass of alkylphenol mixture in product / mass of lignin oil before reaction)´100%.

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Abstract

The invention relates to a method for preparing alkylphenol and alkyl diphenol from lignin oil. According to the method, the lignin oil is taken as the raw material and is utilized for preparing phenol products such as alkylphenol and alkyl diphenol through selective hydrogenation deoxygenation in equipment of a batch type reaction kettle, a fixed bed, a fluidized bed and the like under the effectof a niobium base material loaded metal catalyst. The lignin oil is prepared from lignin separated by virtue of various methods and lignocellulose containing lignin by virtue of a depolymerization method. The raw material sources are wide, and the cost is low. Meanwhile, the product is single and contains few byproducts, the separation is simple, and the separation energy consumption is reduced.Besides, phenol compounds are importable chemical products, can be used for preparing phenol and olefin through further catalytic cracking and have has wide application prospects.

Description

technical field [0001] The invention provides a method for preparing alkylphenols and alkyldiphenols from lignin oil. Using lignin oil as raw material, under the action of a metal catalyst supported by niobium-based materials, selective hydrodeoxygenation is used to obtain alkylphenols and alkyldiphenols. Diphenol-based phenolic products. It belongs to the research field of using lignin to synthesize chemicals. Background technique [0002] At present, the problems of energy shortage and environmental pollution are becoming more and more prominent, and it is imminent to develop renewable resources that can replace fossil energy. Biomass has a wide range of sources and is cheap. The new technology of preparing fuel and fine chemicals from biomass has attracted the attention of scientists all over the world. As the main component of biomass, lignin is the main by-product of lignocellulosic biomass hydrolysis and fermentation to produce ethanol industry and pulp and paper ind...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/54C07C39/06C07C39/08C07C37/52C07C39/04B01J27/195B01J23/68B01J23/89B01J23/20B01J27/24
CPCY02P20/52Y02P20/54
Inventor 王艳芹董琳刘晓晖
Owner EAST CHINA UNIV OF SCI & TECH
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