CN114736103B - Method for separating propyl guaiacol and propyl syringol from lignin oil - Google Patents
Method for separating propyl guaiacol and propyl syringol from lignin oil Download PDFInfo
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Abstract
The invention discloses a method for separating propyl guaiacol and propyl syringol from lignin oil, which comprises the following steps: extracting lignin oil with hydrocarbon organic solvent to obtain monomer concentrated oil; dissolving monomer concentrated oil in organic solvent, extracting with 0.2-1.5mol/L potassium hydroxide aqueous solution, increasing potassium hydroxide concentration in alkali liquor, cooling, crystallizing, filtering to obtain propyl syringol potassium salt crystal and filtrate, and converting propyl syringol potassium salt crystal into propyl syringol crude product; refining to obtain refined propyl eugenol; reducing the concentration of potassium hydroxide in the filtrate, and extracting with an organic solvent to obtain a crude propyl guaiacol product; refining to obtain refined propyl guaiacol product. The method is simple, quick and efficient, does not need complex experimental equipment and materials, has low requirements on the skills of experimental staff, is easy to amplify, has high product purity, and is environment-friendly, and the used organic solvent and alkali liquor can be recycled and reused for separation.
Description
Technical Field
The invention belongs to the field of biomass conversion preparation chemicals, and particularly relates to a method for separating propyl guaiacol and propyl syringol from lignin oil.
Background
Lignin is the renewable phenolic polymer biomass with the greatest worldwide yield, and its fundamental monomers mainly include guaiacyl, syringyl and para-hydroxyphenyl monomers. Lignin can be converted to products rich in phenols (including monomers, dimers, oligomers, etc.) by depolymerization techniques (ChemCatChem 2019,11,639-654). These products are considered to be an important source of renewable phenolic chemicals.
In recent years, the reduction-catalyzed depolymerization (RCF) process has become an important means of depolymerizing lignin to produce renewable phenolic chemicals (curr. Opin. Biotechnol.2019,56, 193-201). The typical technical conditions of the process are as follows: takes wood or lignin as raw material, alcohols such as methanol, ethanol and the like as solvent, metals such as Ru, pd, ni, cu and the like as catalyst, takes hydrogen or nitrogen as gas phase, and reacts for 1 to 6 hours at a high temperature of 180 to 250 ℃ in a high-pressure reactor, wherein lignin components in the lignin or the wood undergo depolymerization and catalytic reduction reaction, and finally the products of monomer products of propyl guaiacol and propyl eugenol or hydroxypropyl guaiacol and hydroxypropyl eugenol are produced. The method has the advantages of high yield and selectivity of phenolic monomer products, but has the defect of high reaction pressure. For this purpose, scientists at the university of Tianjin have proposed an atmospheric reduction catalytic depolymerization (ARCF) technique using alcohols such as high boiling point ethylene glycol as a solvent in addition to the RCF technique, and carried out at a boiling point temperature or lower and in an air atmosphere. Thus, the process is carried out under normal pressure and open conditions, greatly optimizing the process difficulty and maintaining high product yields and selectivities (Green chem.,2021,23,1648-1657, cn 20201102295290.9). RCF and ARCF are representative processes in lignin depolymerization conversion utilization processes, and have high industrial application value and prospect (Energy environment. Sci.,2021,14,4147-4168). The liquid phase products obtained by the RCF and ARCF processes can be desolventized and desugared to obtain lignin oil, namely lignin depolymerization products. The lignin oil has complex components and is difficult to separate a single substance with higher purity from the lignin oil.
Propylguaiacol (1) and propyleugenol (2) are the two major phenolic monomer products in lignin oils. They have wide application in the fields of food, medicine, new materials, daily chemicals and the like. For example, both are food and household flavors that are national standards allow for use; they can be further synthesized into various phenolic monomer products, bisphenol a substitutes, and novel polyester materials (Green chem.,2018,20,1050-1058). Although both yield and selectivity are higher in RCF and ARCF, existing separation and purification processes rely solely on column chromatography. The method requires a lot of time and reagents, and is inefficient and costly, thus making it difficult to implement large-scale applications. The university of belgium, sels, subject group, proposes a rectification method to purify both substances (Green chem.,2018,20,1050-1058), but the method is limited to software simulation, no actual experimental data is available, and the purity of propyl guaiacol calculated by the method is only 67.3%.
Therefore, an efficient and simple product separation method is provided, and the obtained propyl guaiacol and propyl syringol with higher purity have important significance for the industrial application of RCF and ARCF technologies and the development of lignin conversion utilization technologies.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for separating propyl guaiacol and propyl syringol from lignin oil.
The technical scheme of the invention is as follows:
a method for separating propylguaiacol and propyleugenol from lignin oil, comprising the steps of:
(1) Extracting lignin oil with hydrocarbon organic solvent to obtain first extractive solution, refrigerating the first extractive solution at-40-15deg.C for at least 1 hr, separating out oily substance and second extractive solution;
(2) Extracting the oily substance obtained in the step (1) by using a hydrocarbon organic solvent to obtain a third extracting solution, refrigerating the third extracting solution at the temperature of-40-15 ℃ for at least 1 hour to obtain a fourth extracting solution, combining the second extracting solution and the fourth extracting solution, and removing the solvent to obtain monomer concentrated oil;
(3) Dissolving the monomer concentrated oil obtained in the step (2) in an organic solvent, extracting at least 2 times by using 0.2-1.5mol/L potassium hydroxide aqueous solution, filtering the extracted alkali liquor, merging, and collecting an organic phase for recycling to the next batch to participate in dissolving the monomer concentrated oil;
(4) Increasing the concentration of potassium hydroxide in the alkali liquor obtained in the step (3), cooling to separate out the propyl eugenol potassium salt crystals, and filtering to obtain propyl eugenol potassium salt crystals and filtrate;
(5) Converting the propyl eugenol potassium salt crystal obtained in the step (4) into a propyl eugenol crude product in an acidification or organic solvent extraction mode; refining to obtain refined propyl eugenol;
(6) Reducing the concentration of potassium hydroxide in the filtrate obtained in the step (4), extracting with an organic solvent, and evaporating the organic solvent of the extract to obtain a crude propyl guaiacol product; refining to obtain refined propyl guaiacol product.
The hydrocarbon organic solvent is at least one hydrocarbon of C6-C8.
The organic solvent in the step (3) is at least one of C6-C8 hydrocarbon, ethyl acetate, methylene dichloride and diethyl ether.
The organic solvent in the step (5) is at least one of C6-C8 hydrocarbon, ethyl acetate, methylene dichloride and diethyl ether.
The organic solvent in the step (6) is at least one of C6-C8 hydrocarbon, ethyl acetate, methylene dichloride and diethyl ether.
The method for improving the concentration of potassium hydroxide in the alkali liquor obtained in the step (3) in the step (4) is as follows: adding potassium hydroxide or removing part of water in the alkali liquor to raise the concentration of potassium hydroxide to 0.5-2.5 mol/L.
The mode of reducing the concentration of the potassium hydroxide in the filtrate obtained in the step (4) in the step (6) is to neutralize with acid water solution or dilute with water, so that the concentration of the potassium hydroxide is reduced to 0.4-1.3 mol/L.
The invention has the advantages that:
(1) The method realizes the separation and purification of the propyl guaiacol and the propyl syringol in the lignin reduction depolymerization product. The purity of the obtained propyl guaiacol product can reach more than 84 percent, the propyl guaiacol product contains 7 percent of propyl syringol impurities, and the purity of the propyl syringol product can reach more than 98.0 percent.
(2) Compared with the existing column chromatography separation method, the method has the advantages of simplicity, rapidness, high efficiency, no need of complex experimental equipment and materials, low requirement on experimenters' skills, easy amplification, capability of recycling most of the used reagent raw materials, and the like, and is environment-friendly;
(3) The propyl guaiacol product has obvious fragrance, the propyl syringol product has weak fragrance, both are pale yellow clear solution, and the color of the propyl guaiacol is lighter.
Drawings
FIG. 1 is a partial enlarged view of a gas chromatogram of propyl eugenol (crude product) obtained in example 1, with the upper right-hand corner inset being a complete view;
FIG. 2 is a partial enlarged view of a gas chromatogram of propylguaiacol (crude product) obtained in example 1, with the upper right-hand corner inset as a complete figure;
FIG. 3 is a partial enlarged view of a gas chromatogram of propyl eugenol (purified product) obtained in example 1, with the upper right-hand corner inset being a complete view;
FIG. 4 is a partial enlarged view of a gas chromatogram of propylguaiacol (purified product) obtained in example 1, with the upper right hand corner inset as a complete drawing.
Detailed Description
The invention is further illustrated by the following examples.
Example 1
A method for separating propylguaiacol and propyleugenol from lignin oil, comprising the steps of:
(1) Extracting 10g lignin oil with 50ml n-hexane for 4 times each time, mixing the extractive solutions to obtain first extractive solution, refrigerating the first extractive solution at-40deg.C for 1 hr, and separating out oily substance and second extractive solution;
(2) Extracting the oily substance obtained in the step (1) with 20ml of n-hexane for 3 times each time, combining to obtain a third extracting solution, refrigerating the third extracting solution at the temperature of minus 40 ℃ for 1 hour to obtain a fourth extracting solution, combining the second extracting solution and the fourth extracting solution, and removing the solvent by rotary evaporation to obtain 2.5g of monomer concentrated oil;
(3) Dissolving the monomer concentrated oil obtained in the step (2) in dichloromethane, sequentially extracting with 15ml of 0.2, 0.4, 0.6 and 0.8mol/L potassium hydroxide aqueous solution for 4 times, filtering the extracted alkali liquor, merging, and collecting an organic phase for recycling to the next batch to participate in dissolving the monomer concentrated oil;
(4) Increasing the concentration of potassium hydroxide in the alkali liquor obtained in the step (3) (the alkali liquor obtained in the step (3) is concentrated to 30ml by rotary evaporation, the concentration of potassium hydroxide is about 0.5mol/L at the moment), cooling to 4 ℃, crystallizing and separating out the potassium propyl eugenol salt, and filtering to obtain potassium propyl eugenol salt crystals and filtrate; (the filtrate can also be participated in the next batch of the potassium hydroxide aqueous solution of step (3);
(5) Adding hydrochloric acid for acidification to convert the propyl eugenol potassium salt crystal obtained in the step (4) into 1.2g of propyl eugenol crude product with the purity of 96.9%;
(6) Neutralizing with hydrochloric acid aqueous solution, reducing the concentration of potassium hydroxide in the filtrate obtained in the step (4) to 0.4mol/L, extracting with 15ml of n-hexane for 5 times, and evaporating the organic solvent of the extract to obtain crude propyl guaiacol product, 0.70g and purity of 76.5%;
refining a crude product of propyl eugenol:
the crude product of the propyl eugenol is dissolved in a hot potassium hydroxide aqueous solution (60 ℃) to ensure that the concentration of potassium hydroxide in the liquid after the crude product of the propyl eugenol is dissolved is more than 0.5mol/L (the concentration of potassium hydroxide in the liquid is 0.7mol/L through detection), the temperature is reduced, the crystal of the potassium salt of the propyl eugenol is separated out, the filtration is carried out, and the obtained crystal is acidified to obtain the refined product of the propyl eugenol (the yield is 88 percent and the purity is 99.1 percent).
Refining of crude propyl guaiacol:
dissolving the crude product of the propyl guaiacol in a hot sodium hydroxide aqueous solution (60 ℃), filtering to ensure that the concentration of sodium hydroxide in the liquid after the crude product of the propyl guaiacol is dissolved is more than 1.5mol/L (the concentration of sodium hydroxide in the liquid is detected to be 2 mol/L), cooling, crystallizing and separating out sodium salt of the propyl guaiacol, filtering, and acidifying the obtained crystal to obtain a refined product of the propyl guaiacol (the yield is 87 percent and the purity is 84 percent).
Example 2
A method for separating propylguaiacol and propyleugenol from lignin oil, comprising the steps of:
(1) Extracting 10g of lignin oil with 50ml of hydrocarbon organic solvent (the hydrocarbon organic solvent is prepared from n-heptane and n-hexane according to the volume ratio of 1:1) for 4 times, mixing the extractive solutions to obtain first extractive solution, refrigerating the first extractive solution at-20deg.C for 3 hr, and separating out oily substance and second extractive solution;
(2) Extracting the oily substance obtained in the step (1) with 20ml of hydrocarbon organic solvent (the hydrocarbon organic solvent is formed by n-heptane and n-hexane according to the volume ratio of 1:1) for 3 times, combining to obtain a third extract, refrigerating the third extract at the temperature of-20 ℃ for 3 hours to obtain a fourth extract, combining the second extract and the fourth extract, and removing the solvent to obtain 2.5g of monomer concentrated oil;
(3): dissolving the monomer concentrated oil obtained in the step (2) in normal hexane, sequentially extracting with 10ml of 0.5, 0.8, 1.2 and 1.5mol/L potassium hydroxide aqueous solution for 4 times, filtering the extracted alkali liquor, merging, and collecting an organic phase for recycling to the next batch to participate in dissolving the monomer concentrated oil;
with n-heptane, 2-dimethylhexane (isooctane) or in a volume ratio of 1:1, replacing the normal hexane in the step with the mixed solution of normal heptane and diethyl ether, and completing the step
(4) Increasing the concentration of potassium hydroxide in the alkali liquor obtained in the step (3) (1 g of potassium hydroxide is added into the alkali liquor obtained in the step (3), the concentration of the potassium hydroxide is about 1.0mol/L at the moment), cooling to 4 ℃, crystallizing and separating out the propyl eugenol potassium salt, and filtering to obtain propyl eugenol potassium salt crystals and filtrate; (the filtrate can also be participated in the next batch of the potassium hydroxide aqueous solution of step (3);
(5) Dissolving the propyl eugenol potassium salt crystal obtained in the step (4) in 10ml of water, extracting for 3 times with 15ml of dichloromethane, combining the extracting solutions, and evaporating the dichloromethane to obtain 1.1g of propyl eugenol crude product with the purity of 96.7%;
with n-heptane, 2-dimethylhexane (isooctane) or in a volume ratio of 1:1, replacing dichloromethane in the step with a mixed solution of n-heptane and diethyl ether, and completing the step;
(6) Neutralizing with hydrochloric acid aqueous solution, reducing the concentration of potassium hydroxide in the filtrate obtained in the step (4) to 0.7mol/L, extracting with 15ml of ethyl acetate for 5 times, and evaporating the organic solvent of the extract to obtain crude propyl guaiacol product, 0.74g and purity of 79.5%;
with n-heptane, 2-dimethylhexane (isooctane) or in a volume ratio of 1:1, replacing ethyl acetate in the step with a mixed solution of n-heptane and diethyl ether, and completing the step;
refined propyl eugenol (yield 84%, purity 98.4%); refined propyl guaiacol (yield 85%, purity 89.2%).
Example 3
A method for separating propylguaiacol and propyleugenol from lignin oil, comprising the steps of:
(1) Extracting 10g lignin oil with 50ml 2, 2-dimethylhexane (isooctane) for 4 times, mixing the extractive solutions to obtain first extractive solution, refrigerating the first extractive solution at 15deg.C for 3 hr, separating out oily substance and second extractive solution;
(2) Extracting the oily substance obtained in the step (1) with 20ml of 2, 2-dimethylhexane (isooctane) for 3 times each time, combining to obtain a third extracting solution, refrigerating the third extracting solution at 15 ℃ for 3 hours to obtain a fourth extracting solution, combining the second extracting solution and the fourth extracting solution, and removing the solvent to obtain 2.4g of monomer concentrated oil;
(3) Dissolving the monomer concentrated oil obtained in the step (2) in ethyl acetate, sequentially extracting with 35ml of 0.5mol/L potassium hydroxide aqueous solution and 0.7mol/L potassium hydroxide aqueous solution for 2 times, filtering the extracted alkali liquor, merging, and collecting an organic phase for recycling to the next batch to participate in dissolving the monomer concentrated oil;
(4) Increasing the concentration of potassium hydroxide in the alkali liquor obtained in the step (3) (the alkali liquor obtained in the step (3) is concentrated to 11ml by rotary evaporation, the concentration of potassium hydroxide is about 2.5mol/L at the moment), cooling to 4 ℃, crystallizing and separating out propyl eugenol potassium salt, and filtering to obtain propyl eugenol potassium salt crystals and filtrate; (the filtrate can also be participated in the next batch of the potassium hydroxide aqueous solution of step (3);
(5) Adding hydrochloric acid for acidification to convert the propyl eugenol potassium salt crystal obtained in the step (4) into 1.4g of propyl eugenol crude product with the purity of 93.7%;
(6) Diluting with water, reducing the concentration of potassium hydroxide in the filtrate obtained in the step (4) to 1.3mol/L, extracting with 25ml of ethyl acetate for 8 times, and evaporating the organic solvent of the extract to obtain crude propyl guaiacol, wherein the purity of 0.81g is 84.5%;
refined propyl eugenol (yield 88%, purity 98.0%); refined propyl guaiacol (89% yield, 94.1% purity).
Claims (1)
1. A method for separating propylguaiacol and propyleugenol from lignin oil, comprising the steps of:
(1) Extracting lignin oil with hydrocarbon organic solvent to obtain first extractive solution, refrigerating the first extractive solution at-40-15deg.C for at least 1 hr, separating out oily substance and second extractive solution; the hydrocarbon organic solvent is at least one hydrocarbon of C6-C8;
(2) Extracting the oily substance obtained in the step (1) by using a hydrocarbon organic solvent to obtain a third extracting solution, refrigerating the third extracting solution at the temperature of-40-15 ℃ for at least 1 hour to obtain a fourth extracting solution, combining the second extracting solution and the fourth extracting solution, and removing the solvent to obtain monomer concentrated oil; the hydrocarbon organic solvent is at least one hydrocarbon of C6-C8;
(3) Dissolving the monomer concentrated oil obtained in the step (2) in an organic solvent, extracting at least 2 times by using 0.2-1.5mol/L potassium hydroxide aqueous solution, filtering the extracted alkali liquor, merging, and collecting an organic phase for recycling to the next batch to participate in dissolving the monomer concentrated oil; the organic solvent is at least one of C6-C8 hydrocarbon, ethyl acetate, methylene dichloride and diethyl ether;
(4) Increasing the concentration of potassium hydroxide in the alkali liquor obtained in the step (3), cooling to separate out the propyl eugenol potassium salt crystals, and filtering to obtain propyl eugenol potassium salt crystals and filtrate; the method for improving the concentration of potassium hydroxide in the alkali liquor obtained in the step (3) comprises the following steps: adding potassium hydroxide or removing part of water in the alkali liquor to increase the concentration of the potassium hydroxide to 0.5-2.5 mol/L;
(5) Converting the propyl eugenol potassium salt crystal obtained in the step (4) into a propyl eugenol crude product in an acidification or organic solvent extraction mode; refining to obtain refined propyl eugenol; the organic solvent is at least one of C6-C8 hydrocarbon, ethyl acetate, methylene dichloride and diethyl ether;
(6) Reducing the concentration of potassium hydroxide in the filtrate obtained in the step (4), extracting with an organic solvent, and evaporating the organic solvent of the extract to obtain a crude propyl guaiacol product; refining to obtain refined propyl guaiacol product; the organic solvent is at least one of C6-C8 hydrocarbon, ethyl acetate, methylene dichloride and diethyl ether; the mode of reducing the concentration of the potassium hydroxide in the filtrate obtained in the step (4) is to neutralize with acid water solution or dilute with water, so that the concentration of the potassium hydroxide is reduced to 0.4-1.3 mol/L.
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| CN113999090A (en) * | 2021-11-26 | 2022-02-01 | 南亚新材料科技股份有限公司 | Method for separating phenolic compounds from lignin sulfonate depolymerized products |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102019209844A1 (en) * | 2018-07-10 | 2020-01-16 | Research Triangle Institute | METHOD FOR SELECTIVE OBTAINING A PHENOLIC COMPOUND FROM A BATCH INCLUDING RAW ORGANIC AND / OR ORGANIC OIL |
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| CN1114956A (en) * | 1993-02-18 | 1996-01-17 | 罗富源 | Extraction of natural guaiacol |
| CN102976906A (en) * | 2012-10-26 | 2013-03-20 | 厦门大学 | Method for separating phenols from bio-oil |
| CN103524283A (en) * | 2013-10-12 | 2014-01-22 | 浙江大学 | Method for extracting monophenol compounds and pyrolysis lignin from biological oil |
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