CN110407888B - Method for promoting depolymerization of sulfate lignin by using waste cigarette filter tip - Google Patents
Method for promoting depolymerization of sulfate lignin by using waste cigarette filter tip Download PDFInfo
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Abstract
The invention discloses a method for promoting depolymerization of kraft lignin by using a waste cigarette filter, which comprises the steps of crushing the waste cigarette filter, uniformly mixing the crushed waste cigarette filter with kraft lignin and a microwave absorption medium, grinding the mixture, and pressing the ground mixture into blocky mixtures with different shapes; putting the blocky mixture into a microwave reactor, introducing nitrogen in advance to exhaust air in a reaction system, introducing the nitrogen carrying dichloromethane into the microwave reactor, starting the microwave reactor, and condensing generated depolymerized steam to obtain liquid serving as pyrolysis oil; and (3) sealing and standing the pyrolysis oil at normal temperature, collecting a lower organic phase, dehydrating the collected organic phase to obtain a moisture-free organic phase, and performing normal-temperature rotary evaporation on the organic phase, wherein when no distillate is distilled out, the non-evaporated substance is a phenol-rich compound, and the evaporated liquid substance is dichloromethane which is recycled.
Description
Technical Field
The invention belongs to the field of waste resource utilization, and particularly relates to a method for promoting depolymerization of kraft lignin by using a waste cigarette filter.
Background
The kraft lignin is a main byproduct of the pulping by the sulfate method, exists in black liquor generated in the pulping process, and the black liquor is usually concentrated and burned off in an alkali recovery section to recover alkali, so that a large amount of lignin resources are directly combusted and treated, and the utilization added value is low. The kraft lignin is rich in aromatic rings in the structure and is connected with a large number of hydroxyl active functional groups, so that the kraft lignin has the potential of replacing the traditional fossil resources to prepare high-value fine chemicals such as monophenol compounds. The rapid thermal cracking technology is one of the thermochemical conversion technologies with great application prospects and development potentials for the high-value conversion of lignin resources, but due to the complex three-dimensional network structure, the high condensation degree, the uncertain molecular conformation and the random molecular aggregation of the kraft lignin, the kraft lignin is difficult to further depolymerize in the conventional thermal cracking environment and is extremely easy to condense into carbon.
Cigarette filters are continuous, bundled arrays of cellulose acetate wrapped in a paper shell at the end of a cigarette for the purpose of reducing the amount of smoke, tar and aerosol particles generated during combustion when smoking. Approximately 6 trillion cigarettes are produced worldwide each year, which results in 120 million tons of butt waste, statistically, with over 75 million tons of butt thrown into the environment each year. China, as a contracting country of tobacco control framework convention, faces systematization and normalization of cigarette management and cigarette end classified recovery.
Because the waste cigarette filter is easy to depolymerize due to the unique cellulose acetate component and can generate a large amount of oxygen free radicals in the depolymerization process, and the oxygen free radicals are very beneficial to the depolymerization of the kraft lignin, the waste cigarette filter is used for assisting and promoting the depolymerization of the kraft lignin, and the waste cigarette filter has a positive significance for the high-value utilization of the kraft lignin.
Disclosure of Invention
The invention aims to provide a method for promoting the depolymerization of kraft lignin by using a waste cigarette filter tip, which is used for solving the problems that the existing kraft lignin is difficult to depolymerize effectively and the like, is beneficial to changing waste of the waste cigarette filter tip into valuables and realizes high-value use. According to the invention, after the kraft lignin and the waste cigarette filter tip are mixed and briquetted, microwave-assisted depolymerization is carried out in a microwave system, so that the kraft lignin can be effectively depolymerized into monophenol compounds.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for promoting depolymerization of kraft lignin by using a waste cigarette filter comprises the following steps:
the method comprises the following steps: crushing the waste cigarette filter tip into particles with the particle size of 0.1-1 mm, uniformly mixing the particles with 0.01-0.5 mm of kraft lignin and 500-0.5 mm of microwave absorption medium, grinding, pressurizing the ground mixture for 0.5-10 minutes under the condition of 8-30 MPa, and pressing into block-shaped mixtures with different shapes;
step two: placing the blocky mixture obtained in the step one in a microwave reactor, introducing nitrogen in advance to exhaust air in a reaction system, and then introducing nitrogen carrying dichloromethane into the microwave reactor, wherein the mass of dichloromethane carried in each milliliter of nitrogen is 3-5 mg;
step three: starting a microwave reactor under the condition of ensuring that nitrogen carrying dichloromethane is introduced, wherein the microwave frequency is 2.45GHz, the microwave power is 800-1500W, the temperature is increased to 500-700 ℃, the temperature is kept for 10-30 minutes, the generated depolymerized vapor is condensed at the temperature of-40 to-20 ℃, and the collected liquid is pyrolytic oil;
step four: closing the microwave reactor, keeping introducing nitrogen, stopping introducing nitrogen when the temperature in the microwave reactor is reduced to be below 150 ℃, and finishing the reaction;
step five: and (3) sealing and standing the pyrolysis oil at normal temperature, collecting a lower organic phase, dehydrating the collected organic phase to obtain a moisture-free organic phase, carrying out normal-temperature rotary evaporation on the organic phase, wherein when no distillate is distilled out, the non-evaporated substance is a phenol-rich compound, and the evaporated liquid substance is dichloromethane and is circularly used in the step two.
Furthermore, the mass ratio of the sulfate lignin, the waste cigarette filter tip and the microwave absorbing medium in the first step is 1 (0.05-1) to (0.2-1).
Further, the microwave absorbing medium in the first step is one of silicon carbide, ferroferric oxide and sodium carbonate.
Further, in the second step, the nitrogen flow rate corresponding to each gram of the massive mixture is 1-4 mL/min, and the nitrogen introducing time is 5-10 minutes.
Further, in the second step, the nitrogen is enabled to carry the dichloromethane by passing the nitrogen through a Meng gas washing bottle filled with the dichloromethane, and after the microwave reactor is closed in the fourth step, the Meng gas washing bottle filled with the dichloromethane is removed and the nitrogen is kept introduced.
Further, in step two, nitrogen gas carrying dichloromethane was introduced into the microwave reactor for 5 minutes.
Further, in the fifth step, the pyrolysis oil is sealed and kept still for 12 hours at normal temperature.
And further, adding a drying agent into the collected organic phase for dehydration in the fifth step, wherein the dehydration process is specifically stirring for 10-30 minutes, and the weight ratio of the added drying agent to the organic phase is (0.2-1): 1.
Further, the drying agent in the fifth step is anhydrous sodium sulfate or anhydrous magnesium sulfate.
Compared with the prior art, the invention has the following beneficial technical effects:
1. the kraft lignin contains a large amount of condensed benzene ring structures, particularly a large amount of carbon-carbon bonds, is easily condensed into charcoal under conventional depolymerization conditions, has low depolymerization efficiency, and is difficult to obtain monophenol compounds with high yield. The waste cigarette filter tip is crushed and then mixed with the kraft lignin, and a large amount of oxygen-containing free radicals generated in the depolymerization process of the waste cigarette filter tip are utilized to assist in promoting the breakage of carbon-carbon bonds in the kraft lignin, so that the depolymerization efficiency of the kraft lignin is greatly improved. Meanwhile, waste kraft lignin and waste cigarette filter tips are changed into valuable materials in the pulping and papermaking processes, the utilization value of the waste kraft lignin and the waste cigarette filter tips is improved, and the environmental quality is improved.
2. The invention mixes the sulphate lignin, the waste cigarette filter tip and the microwave absorbing medium and presses them into a block mixture under a certain pressure, mainly aims to pre-carbonize the block mixture by the microwave absorbing medium, and then realizes rapid heating and depolymerization (the microwave absorbing capacity of the raw material in the powder state is very weak) by the dielectric heating effect of the high dielectric constant of the pre-carbonized block mixture in the microwave reactor, thereby improving the yield of the target product.
3. According to the invention, the reaction gas-dichloromethane is added into the microwave reaction system, on one hand, the dichloromethane can be used as a system gas phase solvent to carry out the reaction product quickly and realize quick condensation, so that the occurrence of secondary reaction is effectively inhibited, and the problems that the depolymerization product is adhered to the wall of the reaction tube and the like are prevented, thereby improving the yield of the reaction product; on the other hand, the strong extraction effect of dichloromethane is utilized, the oil-water separation of the pyrolysis oil product can be realized, the target product monophenol compound can be obtained from the oil phase through simple rotary evaporation, and the distillate of the rotary evaporation, namely dichloromethane, can also be recycled for the reaction system.
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FIG. 1 is a process flow diagram of the present invention.
Detailed Description
Embodiments of the invention are described in further detail below:
a method for promoting depolymerization of kraft lignin by using a waste cigarette filter comprises the following steps:
the method comprises the following steps: crushing the waste cigarette filter tip into particles with the particle size of 0.1-1 mm, uniformly mixing the particles with 0.01-0.5 mm of kraft lignin and 500-0.5 mm of microwave absorption medium, grinding, pressurizing the ground mixture for 0.5-10 minutes under the condition of 8-30 MPa, and pressing into block mixtures (cylindrical, square, rhombic and the like) with different shapes. Sulfate lignin: waste cigarette filters: the microwave absorbing medium (weight ratio) is 1 (0.05-1) to 0.2-1; the microwave absorbing medium is one of silicon carbide, ferroferric oxide and sodium carbonate.
Step two: placing the blocky mixture in a microwave reactor, and introducing nitrogen in advance to exhaust air in a reaction system, wherein the nitrogen flow corresponding to each gram of blocky mixture is 1-4 mL/min, and the nitrogen introduction time is 5-10 minutes; then, passing nitrogen through a Meng's gas washing bottle filled with dichloromethane to enable the nitrogen to carry the dichloromethane, and introducing the nitrogen carrying the dichloromethane into the microwave reactor for 5 minutes, wherein the mass of the dichloromethane carried in each milliliter of nitrogen is 3-5 mg;
step three: and under the condition of ensuring that nitrogen carrying dichloromethane is introduced, starting a microwave reactor, wherein the microwave frequency is 2.45GHz, the microwave power is 800-1500W, heating to 500-700 ℃, keeping the temperature for 10-30 minutes, condensing the generated depolymerized vapor at-40 to-20 ℃, and collecting liquid as pyrolysis oil.
Step four: and (3) closing the microwave reactor, removing the Mene's gas washing bottle filled with dichloromethane, keeping introducing nitrogen, stopping introducing the nitrogen when the temperature in the microwave reactor is reduced to be below 150 ℃, and finishing the reaction.
Step five: and (2) standing the pyrolysis oil for 12 hours in a closed manner at normal temperature, layering the pyrolysis oil, collecting the lower organic phase by using a separating funnel, adding a drying agent into the collected organic phase for dehydration, stirring for 10-30 minutes, wherein the weight ratio of the drying agent to the organic phase is (0.2-1): 1, and the drying agent is anhydrous sodium sulfate or anhydrous magnesium sulfate. And (3) after drying, filtering and removing the drying agent to obtain an organic phase without moisture, carrying out normal-temperature rotary evaporation on the organic phase, wherein when no distillate is distilled out, the non-evaporated substance is the phenol-rich compound, and the evaporated liquid substance is dichloromethane and is circularly used in the step two.
The present invention is described in further detail below with reference to examples:
example 1
10g of kraft lignin having a particle size of 0.3mm to 0.5mm, 10g of waste cigarette filters pulverized to have a particle size of 0.6mm to 1mm, and 10g of sodium carbonate having a particle size of 500nm to 800nm were uniformly mixed and then ground, and the ground mixture was pressurized at 30MPa for 0.5 minute and pressed into a cylindrical shape. Placing the cylindrical mixture in a microwave reactor, introducing nitrogen at the rate of 120mL/min for 5 minutes, then passing the nitrogen through a Mene's gas washing bottle filled with dichloromethane to enable the nitrogen to carry the dichloromethane, wherein the carrying amount is 600mg/min, starting the microwave reactor after 5 minutes, the microwave frequency is 2.45GHz, the microwave power is 1500W, heating to 700 ℃, keeping the temperature for 10 minutes, condensing the generated depolymerization steam at the temperature of-40 ℃, and collecting 24.2g of liquid product containing the dichloromethane, namely pyrolysis oil. And then closing the microwave reactor, removing the Mene's gas washing bottle filled with dichloromethane, keeping introducing nitrogen, stopping introducing the nitrogen when the temperature in the microwave reactor is reduced to be below 150 ℃, and finishing the reaction. The method comprises the steps of standing pyrolysis oil for 12 hours in a closed mode at normal temperature, collecting a lower-layer organic phase through a separating funnel, adding 20.4g of anhydrous sodium sulfate into 20.4g of the collected organic phase for dehydration, stirring for 10 minutes, filtering and removing a drying agent to obtain a moisture-free organic phase, carrying out normal-temperature rotary evaporation on the organic phase, determining that substances which are not evaporated are 8.5g when no distillate is distilled out, concentrating the molecular weight determination range of the substances in the range of 85-162 Da, and analyzing and detecting through gas chromatography-mass spectrometry to obtain the organic phase containing the main components of guaiacol, phenol, vanillin and other monophenol compounds and occupying 64% of the area content of the components of the organic phase.
Example 2
Mixing 10g of kraft lignin with the particle size of 0.1-0.3 mm, 5g of waste cigarette filter tips with the particle size of 0.4-0.6 mm and 5g of ferroferric oxide with the particle size of 800 nm-0.2 mm uniformly, grinding, pressurizing the ground mixture for 5 minutes under the condition of 15MPa, and pressing into a square shape. Placing the square mixture in a microwave reactor, introducing nitrogen at the rate of 60mL/min for 7 minutes, then passing the nitrogen through a Mene's gas washing bottle filled with dichloromethane to enable the nitrogen to carry the dichloromethane, wherein the carrying amount is 240mg/min, starting the microwave reactor after 5 minutes, the microwave frequency is 2.45GHz, the microwave power is 1200W, heating to 600 ℃, keeping the temperature for 20 minutes, condensing the generated depolymerization steam at the temperature of-30 ℃, and collecting 18.4g of liquid product containing the dichloromethane, namely pyrolysis oil. And then closing the microwave reactor, removing the Mene's gas washing bottle filled with dichloromethane, keeping introducing nitrogen, stopping introducing the nitrogen when the temperature in the microwave reactor is reduced to be below 150 ℃, and finishing the reaction. The method comprises the steps of standing pyrolysis oil for 12 hours in a closed mode at normal temperature, collecting a lower-layer organic phase through a separating funnel, adding 8g of anhydrous magnesium sulfate into 16.0g of the collected organic phase for dehydration, stirring for 15 minutes, filtering and removing a drying agent to obtain a moisture-free organic phase, carrying out normal-temperature rotary evaporation on the organic phase, measuring 9.8g of non-evaporated substances when no distillate is distilled out, determining the molecular weight measuring range of the non-evaporated substances to be concentrated in 70-168 Da, and carrying out gas chromatography-mass spectrometry analysis detection to obtain the organic phase containing the main components of guaiacol, phenol, vanillin, vanillic acid and other monophenol compounds, wherein the area content of the organic phase components is 69%.
Example 3
Mixing 10g of kraft lignin with the particle size of 0.01-0.1 mm, 0.5g of waste cigarette filter tip with the particle size of 0.1-0.4 mm and 2g of silicon carbide with the particle size of 0.2-0.5 mm uniformly, grinding, pressurizing the ground mixture for 10 minutes under the condition of 8MPa, and pressing into a rhombus. Putting the rhombic mixture into a microwave reactor, introducing nitrogen at the rate of 12.5mL/min for 10 minutes, then enabling the nitrogen to carry dichloromethane through a Mene's gas washing bottle filled with dichloromethane, wherein the carrying amount is 37.5mg/min, starting the microwave reactor after 5 minutes, the microwave frequency is 2.45GHz, the microwave power is 800W, heating to 500 ℃, keeping the temperature for 30 minutes, condensing generated depolymerized steam at the temperature of-20 ℃, and collecting 10g of liquid product containing dichloromethane, namely pyrolysis oil. And then closing the microwave reactor, removing the Mene's gas washing bottle filled with dichloromethane, keeping introducing nitrogen, stopping introducing the nitrogen when the temperature in the microwave reactor is reduced to be below 150 ℃, and finishing the reaction. The pyrolysis oil is sealed and kept stand for 12 hours at normal temperature, then a lower-layer organic phase is collected through a separating funnel, 1.86g of anhydrous magnesium sulfate is added into 9.3g of the collected organic phase for dehydration, stirring is carried out for 30 minutes, then a drying agent is filtered and removed, a moisture-free organic phase is obtained, the organic phase is subjected to normal-temperature rotary evaporation, when no distillate is distilled out, the mass which is not evaporated is 7.3g, the molecular weight determination range is determined to be 105-172 Da, and the main components of the organic phase are monophenol compounds such as guaiacol, vanillin, phenol, o-cresol and the like through gas chromatography-mass spectrometry analysis and detection, and the area content of the organic phase components is 86%.
Claims (7)
1. A method for promoting the depolymerization of kraft lignin by using a waste cigarette filter is characterized by comprising the following steps:
the method comprises the following steps: crushing the waste cigarette filter tip into particles with the particle size of 0.1-1 mm, uniformly mixing the particles with kraft lignin with the particle size of 0.01-0.5 mm and a microwave absorption medium with the particle size of 500 nm-0.5 mm, grinding, pressurizing the ground mixture for 0.5-10 minutes under the condition of 8-30 MPa, and pressing into blocky mixtures with different shapes, wherein the mass ratio of the kraft lignin, the waste cigarette filter tip and the microwave absorption medium is 1 (0.05-1) to (0.2-1), and the microwave absorption medium is one of silicon carbide, ferroferric oxide and sodium carbonate;
step two: placing the blocky mixture obtained in the step one in a microwave reactor, introducing nitrogen in advance to exhaust air in a reaction system, and then introducing nitrogen carrying dichloromethane into the microwave reactor, wherein the mass of dichloromethane carried in each milliliter of nitrogen is 3-5 mg;
step three: starting a microwave reactor under the condition of ensuring that nitrogen carrying dichloromethane is introduced, wherein the microwave frequency is 2.45GHz, the microwave power is 800-1500W, the temperature is increased to 500-700 ℃, the temperature is kept for 10-30 minutes, the generated depolymerized vapor is condensed at the temperature of-40 to-20 ℃, and the collected liquid is pyrolytic oil;
step four: closing the microwave reactor, keeping introducing nitrogen, stopping introducing nitrogen when the temperature in the microwave reactor is reduced to be below 150 ℃, and finishing the reaction;
step five: and (3) sealing and standing the pyrolysis oil at normal temperature, collecting a lower organic phase, dehydrating the collected organic phase to obtain a moisture-free organic phase, carrying out normal-temperature rotary evaporation on the organic phase, wherein when no distillate is distilled out, the non-evaporated substance is a phenol-rich compound, and the evaporated liquid substance is dichloromethane and is circularly used in the step two.
2. The method for promoting depolymerization of kraft lignin by using a waste cigarette filter according to claim 1, wherein in the second step, the nitrogen flow rate per gram of the cake mixture is 1-4 mL/min, and the nitrogen gas introduction time is 5-10 minutes.
3. The method for promoting the depolymerization of kraft lignin using waste cigarette filters according to claim 1, wherein in the second step, the nitrogen is passed through a methane washing bottle containing methylene chloride to make the methylene chloride carried with the nitrogen, and in the fourth step, after the microwave reactor is closed, the methane washing bottle containing methylene chloride is removed and the nitrogen is kept introduced.
4. The method for promoting the depolymerization of kraft lignin by using waste cigarette filters according to claim 1, wherein in the second step, nitrogen gas carrying dichloromethane is introduced into the microwave reactor for 5 minutes.
5. The method for promoting the depolymerization of kraft lignin using a waste cigarette filter according to claim 1, wherein in the fifth step, the pyrolysis oil is allowed to stand in a sealed state at normal temperature for 12 hours.
6. The method for promoting the depolymerization of the kraft lignin by using the waste cigarette filter tip according to claim 1, wherein a drying agent is added to the collected organic phase in the fifth step for dehydration, the dehydration is specifically performed by stirring for 10-30 minutes, and the weight ratio of the added drying agent to the organic phase is (0.2-1): 1.
7. The method for promoting the depolymerization of kraft lignin using a waste cigarette filter according to claim 6, wherein the drying agent in the fifth step is anhydrous sodium sulfate or anhydrous magnesium sulfate.
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