CN111675827A - Method for recovering melamine by catalytically degrading melamine resin - Google Patents
Method for recovering melamine by catalytically degrading melamine resin Download PDFInfo
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- CN111675827A CN111675827A CN202010682908.0A CN202010682908A CN111675827A CN 111675827 A CN111675827 A CN 111675827A CN 202010682908 A CN202010682908 A CN 202010682908A CN 111675827 A CN111675827 A CN 111675827A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/02—Recovery or working-up of waste materials of solvents, plasticisers or unreacted monomers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08J2361/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08J2361/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine
Abstract
The invention belongs to the field of cyclic utilization and resource utilization of resin solid wastes, and particularly relates to a method for recovering melamine by catalytically degrading melamine resin. The method comprises the following steps: crushing melamine resin materials into granules, immersing the granules into a catalyst-solvent liquid phase reaction system, reacting at 80-150 ℃ to fully react and degrade the melamine resin materials, cooling to room temperature after the reaction is finished, and separating and recovering to obtain melamine.
Description
Technical Field
The invention belongs to the field of cyclic utilization and resource utilization of resin solid wastes, and particularly relates to a method for recovering melamine by catalytically degrading melamine resin.
Background
Melamine resin is also called melamine-formaldehyde resin, melamine-formaldehyde resin (MF), which is a polymer obtained by reacting melamine with formaldehyde. The product is used as a starting point, different process conditions are adopted according to different purposes, a series of products with different purposes are derived, a cross-linking reaction occurs during processing and molding, and the product is infusible thermosetting resin. Melamine resin is widely applied to a plurality of fields such as catering and children toys, and the like, and the yield of the melamine resin is about millions of tons every year in China. Because melamine resin products have high chemical stability and are not easily catalyzed and degraded by light, microorganisms, water and the like in the environment, a large amount of waste can be accumulated in living space of people, and not only occupies space, but also causes hidden troubles of soil pollution or underground water pollution.
The existing method for recovering and treating waste melamine resin mainly comprises a mechanical treatment method and a high-temperature pyrolysis method. The mechanical treatment method is to mechanically crush cured and molded melamine resin, to be used as a filler to be added into a new round of synthesis of thermosetting resin, and to regulate and control the size and filling amount of the mechanical crushing of the melamine resin according to the performance requirement of the synthetic resin. The method usually needs higher energy consumption, and the crushed melamine granules have small bonding force with new resin, so that the mechanical property of new melamine products can be obviously influenced, the additional value is low, and the economical efficiency is poor. The high-temperature pyrolysis method is mainly used for carrying out high-temperature treatment on waste melamine resin, and chemical bonds in the resin are opened in a non-selective manner by utilizing high temperature, so that corresponding components are recovered.
Melamine (Melamine, chemical formula: C3N3(NH2)3), commonly known as Melamine and protamine, is named as 1, 3, 5-triazine-2, 4, 6-triamine by the International Union of Pure and Applied Chemistry (IUPAC)), is a triazine nitrogen-containing heterocyclic organic compound and is widely Applied to chemical raw materials. The melamine takes urea as raw material, and about 3 tons of urea are needed for producing 1 ton of melamine.
If the ether bond and the CH2-NH bond in the melamine resin can be selectively opened under appropriate reaction conditions, the melamine is catalytically degraded into melamine, which has undoubtedly greater economic and social significance.
Disclosure of Invention
The invention provides a method for recovering melamine by catalytically degrading melamine resin, aiming at the problems of low added value of products of the existing mechanical treatment method, difficult recovery of high-temperature pyrolysis products and the like.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for recovering melamine by catalytically degrading melamine resin comprises the following steps:
crushing melamine resin materials into granules, immersing the granules into a catalyst-solvent liquid phase reaction system, reacting at 80-150 ℃, cooling to room temperature after the reaction is finished, and separating and recovering to obtain the melamine. The invention realizes the catalytic degradation of melamine resin, the material is crushed, the mass transfer effect in the reaction process is convenient to improve, and the proper catalyst-solvent system is selected, so that the catalyst and the solvent can enter the material body and can be conveniently contacted with the active sites of the material reaction, and the catalytic degradation efficiency is further improved. Compared with the traditional treatment means, the method realizes the catalytic degradation of the melamine resin under mild conditions, and has simple product distribution and higher recovery rate. When the degradation temperature is lower than 80 ℃, the reaction rate of the reaction system is extremely low, and when the temperature is higher than 150 ℃, the yield of the melamine is not obviously improved.
Further, the particle size of the granules in the step is 0.1-10 mm. The particle size of the granules is too large, which not only affects mass transfer, but also increases the porosity of a reaction system and affects degradation efficiency, and if the particle size is too small, the energy consumption is too high during crushing, more dust is generated in the production process, and the economical efficiency is not good.
Further, the reaction time in the step is 60 min-24 h. When the reaction time is less than 60min, the above reaction systems cannot completely catalyze the degradation of the melamine resin, and when the reaction time is more than 24h, the extension of the reaction time does not significantly promote the reaction of the melamine resin.
Further, the catalyst in said step is an acidic catalyst. The selected acid catalyst can enter the material body more quickly in a liquid phase reaction system, and is convenient to contact with the material reaction active sites, so that the catalysis rate is improved.
Still further, the acidic catalyst is HCl and HNO3、H3BO3、H2SO4、H2CO3、H3PO4、FeCl3、AlCl3、ZnCl2、CuCl2、MnCl2One or more of p-toluenesulfonic acid and dodecylbenzene sulfonic acid are mixed according to any ratio. The catalyst selected by the technical scheme has a good catalytic effect on the catalytic degradation of melamine resin.
Further, the solvent in the step is water or a mixed solution of water and an organic reagent, and the organic reagent is specifically one or more of methanol, ethanol, n-propanol, isopropanol, formic acid, acetic acid, tetrahydrofuran, diethyl ether, DMSO, dioxane, DMF, gamma-butyrolactone, gamma-valerolactone, acetone or ethylenediamine which are mixed according to any ratio. The reaction solvent with strong reaction activity promotes the reaction of melamine resin through the action of the catalyst.
Still further, the mixed solution of water and an organic reagent has a volume ratio of water to organic reagent of 1:0.5 to 10. By selecting a proper proportion, the mixed solvent has stronger reaction activity.
Furthermore, the mass ratio of the catalyst to the melamine resin in the step is 1: 0.05-5; the mass ratio of the solvent to the melamine resin is 1-100: 1. The catalyst proportion range selected in the technical scheme has a good effect on the catalytic degradation of melamine resin, and the dissolution of the selected organic solvent and the recovered product melamine is low, so that the subsequent separation is facilitated.
Compared with the prior art, the invention has the following advantages:
the invention solves the problems of complex components of high-temperature pyrolysis products, easy generation of virulent hydrocyanic acid and the like in a chemical treatment method by carrying out chemical catalytic degradation on waste melamine tableware, and obtains melamine with high added value by directly adopting a catalyst-solvent system for reaction.
Drawings
FIG. 1 is an infrared spectrum of melamine of example 1 according to the invention;
FIG. 2 shows melamine in example 1 of the present invention13CNMR spectrogram;
FIG. 3 is an NMR spectrum of melamine of example 1 of the present invention.
Detailed Description
Example 1
Pulverizing 1g of waste melamine tableware into granules with particle size of 0.1mm, and soaking in HNO3Water, tetrahydrofuran reaction System (HNO)3The mass ratio of the melamine resin to the melamine resin is 1: 0.05; the mass ratio of the solvent to the melamine resin is 1:1, and the volume ratio of water to tetrahydrofuran in the solvent is 1: 10) reacting at 80 deg.C for 24h in a sealed pressure container to fully react and degrade melamine resin material, cooling to room temperature after reaction, filtering and washing to obtain melamine 0.8g, the infrared spectrogram is shown in figure 1,13the CNMR spectrum is shown in FIG. 2, and the NMR spectrum and the hydrogen spectrum are shown in FIG. 3. The infrared spectrum of melamine is shown in detail in fig. 1, wherein the wave number corresponds to the double bond C ═ N on the melamine ring at position 1845, and the wave number corresponds to the bond N — H outside the ring at position 3268;13the CNMR spectrum is detailed in FIG. 2, chemical shifts at 165.90ppm correspond to carbon in the melamine ring, and other peaks correspond to solvent; the NMR spectrum is detailed in FIG. 3, with chemical shifts at 6.51ppm corresponding to hydrogen outside the melamine ring and other peaks corresponding to solvent.
Example 2
Pulverizing 1g of waste melamine tableware into granules with particle size of 0.2mm, and soaking in ZnCl2Water, DMSO reaction system (ZnCl)2The mass ratio of the melamine resin to the melamine resin is 1: 1; the mass ratio of the solvent to the melamine resin is 20:1, the volume ratio of water to DMSO in the solvent is 1: 0.5) and reacting for 22 hours at 90 ℃ in a closed pressure vessel to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.8g of melamine.
Example 3
1g of waste melamine tableware is crushed into granules with the grain diameter of 0.5mm, the granules are immersed into a reaction system of p-toluenesulfonic acid, water and acetic acid (the mass ratio of the toluenesulfonic acid to the melamine resin is 1:2, the mass ratio of the solvent to the melamine resin is 50:1, the volume ratio of the water to the acetic acid in the solvent is 1: 8), the mixture is reacted for 20 hours in a closed pressure container at the temperature of 100 ℃, the melamine resin material is fully reacted and degraded, the temperature is reduced to the room temperature after the reaction is finished, and 0.82g of melamine is obtained after filtration and washing.
Example 4
Mixing 1g of waste honeyThe amine tableware was pulverized into pellets having a particle size of 1mm, and immersed in H2SO4Water, acetic acid reaction system (H)2SO4The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 80:1, and the volume ratio of water to acetic acid in the solvent is 1: 5) reacting for 18h at 110 ℃ in a closed pressure vessel to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.81g of melamine.
Example 5
Pulverizing 1g of waste melamine tableware into granules with particle size of 1.5mm, and soaking in H2SO4Water, gamma-valerolactone reaction system (H)2SO4The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 80:1, the volume ratio of water to gamma-valerolactone in the solvent is 1: 5) and reacting for 16 hours at 120 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.83g of melamine.
Example 6
Pulverizing 1g of waste melamine tableware into granules with particle size of 2mm, and soaking in MnCl2Water, acetone reaction system (MnCl)2The mass ratio of the melamine resin to the melamine resin is 1: 3; the mass ratio of the solvent to the melamine resin is 100:1, the volume ratio of water to acetone in the solvent is 1: 6) and reacting for 14 hours at 140 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.85g of melamine.
Example 7
Pulverizing 1g of waste melamine tableware into granules with particle size of 3mm, and soaking in H3PO4Water, dioxane reaction System (H)3PO4The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 50:1, the volume ratio of water to dioxane in the solvent is 1: 5) and reacting for 12 hours at 150 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.84g of melamine.
Example 8
1g of waste melamine tableware is crushed into granules with the grain diameter of 5mm, the granules are immersed into a reaction system of HCl-water and methanol (the mass ratio of HCl to melamine resin is 1: 0.5; the mass ratio of a solvent to melamine resin is 10: 1; and the volume ratio of water to methanol in the solvent is 1: 10), the granules react for 23 hours in a closed pressure container at 85 ℃ to ensure that the melamine resin material fully reacts and degrades, the temperature is reduced to room temperature after the reaction is finished, and 0.83g of melamine is obtained after filtering and washing.
Example 9
Pulverizing 1g of waste melamine tableware into granules with particle size of 7mm, and soaking in H3PO4Water, ethanol reaction System (H)3PO4The mass ratio of the melamine resin to the melamine resin is 1: 1; the mass ratio of the solvent to the melamine resin is 20:1, the volume ratio of water to ethanol in the solvent is 1: 5) and reacting for 21 hours at 95 ℃ in a closed pressure vessel to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.8g of melamine.
Example 10
Pulverizing 1g of waste melamine tableware into granules with particle size of 9mm, and soaking into FeCl3(FeCl) in a reaction System of Water and formic acid3The mass ratio of the melamine resin to the melamine resin is 1: 2; the mass ratio of the solvent to the melamine resin is 50:1, the volume ratio of water to formic acid in the solvent is 1: 8) reacting for 19h at 105 ℃ in a closed pressure vessel to ensure that the melamine resin material is fully reacted and degraded, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.81g of melamine.
Example 11
Pulverizing 1g of waste melamine tableware into granules with particle size of 10mm, and soaking in H2CO3Water, diethyl ether reaction System (H)2CO3The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 80:1, the volume ratio of water to diethyl ether in the solvent is 1: 5) reacting for 17h at 115 ℃ in a closed pressure vessel to ensure that the melamine resin material is fully reacted and degraded, cooling to room temperature after the reaction is finished, filtering and washing to obtain melamine0.78g。
Example 12
Pulverizing 1g waste melamine tableware into granules with particle size of 2.5mm, soaking in AlCl3Water, DMF reaction system (AlCl)3The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 80:1, the volume ratio of water to DMF in the solvent is 1: 5) reacting for 15h at 125 ℃ in a closed pressure vessel to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.87g of melamine.
Example 13
Pulverizing 1g of waste melamine tableware into granules with particle size of 5mm, and soaking in MnCl2Water, acetone reaction system (MnCl)2The mass ratio of the melamine resin to the melamine resin is 1: 3; the mass ratio of the solvent to the melamine resin is 100:1, the volume ratio of water to acetone in the solvent is 1: 6) and reacting for 13 hours at 135 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.85g of melamine.
Example 14
Pulverizing 1g of waste melamine tableware into granules with particle size of 6mm, and soaking in CuCl2Water, isopropanol (CuCl)2The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 50:1, the volume ratio of water to isopropanol in the solvent is 1: 5) and reacting for 10 hours at 145 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.88g of melamine.
Example 15
Crushing 1g of waste melamine tableware into granules with the particle size of 7.5mm, immersing the granules into a dodecylbenzene sulfonic acid-water-tetrahydrofuran reaction system (the mass ratio of dodecylbenzene sulfonic acid to melamine resin is 1: 0.5; the mass ratio of solvent to melamine resin is 10: 1; and the volume ratio of water in solvent to tetrahydrofuran is 1: 10), reacting for 1h at 150 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, filtering and washing to obtain 0.85g of melamine.
Example 16
Pulverizing 1g of waste melamine tableware into granules with particle size of 8mm, and soaking the granules into ZnCl2Water, gamma-valerolactone reaction system (ZnCl)2The mass ratio of the melamine resin to the melamine resin is 1: 1; the mass ratio of the solvent to the melamine resin is 20:1, and the volume ratio of water to gamma-valerolactone in the solvent is 1: 5) and reacting for 2 hours at 140 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.75g of melamine.
Example 17
1g of waste melamine tableware is crushed into granules with the grain diameter of 8.5mm, the granules are immersed into a reaction system of p-toluenesulfonic acid, water and acetic acid (the mass ratio of the toluenesulfonic acid to the melamine resin is 1:2, the mass ratio of the solvent to the melamine resin is 50:1, the volume ratio of the water to the acetic acid in the solvent is 1: 8), the mixture is reacted for 5 hours in a closed pressure container at 130 ℃, the melamine resin material is fully reacted and degraded, the temperature is reduced to room temperature after the reaction is finished, and 0.84g of melamine is obtained after filtering and washing.
Example 18
Pulverizing 1g of waste melamine tableware into granules with particle size of 9mm, and soaking in H2SO4Water, ethylenediamine reaction system (H)2SO4The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 80:1, and the volume ratio of water to ethylenediamine in the solvent is 1: 5) reacting for 8 hours at 110 ℃ in a closed pressure vessel to ensure that the melamine resin material is fully reacted and degraded, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.82g of melamine.
Example 19
Pulverizing 1g of waste melamine tableware into granules with particle size of 9.5mm, and soaking in H2SO4Water, gamma-valerolactone reaction system (H)2SO4The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 80:1, the volume ratio of water to gamma-valerolactone in the solvent is 1: 5) reacting for 12h at 100 ℃ in a closed pressure vessel to obtain melamineThe lipid material is fully reacted and degraded, cooled to room temperature after the reaction is finished, filtered and washed to obtain 0.8g of melamine.
Example 20
Pulverizing 1g of waste melamine tableware into granules with particle size of 4.5mm, and soaking in MnCl2Water, acetone reaction system (MnCl)2The mass ratio of the melamine resin to the melamine resin is 1: 3; the mass ratio of the solvent to the melamine resin is 100:1, the volume ratio of water to acetone in the solvent is 1: 6) reacting for 16h at 90 ℃ in a closed pressure container to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.87g of melamine.
Example 21
Pulverizing 1g of waste melamine tableware into granules with particle size of 10mm, and soaking in H3PO4Water, dioxane reaction System (H)3PO4The mass ratio of the melamine resin to the melamine resin is 1: 5; the mass ratio of the solvent to the melamine resin is 50:1, the volume ratio of water to dioxane in the solvent is 1: 5) reacting for 22h at 80 ℃ in a closed pressure vessel to fully react and degrade the melamine resin material, cooling to room temperature after the reaction is finished, and filtering and washing to obtain 0.8g of melamine.
Claims (8)
1. A method for recovering melamine by catalytically degrading melamine resin is characterized by comprising the following steps: the method comprises the following steps:
crushing melamine resin materials into granules, immersing the granules into a catalyst-solvent liquid phase reaction system, reacting at 80-150 ℃, cooling to room temperature after the reaction is finished, and separating and recovering to obtain the melamine.
2. The method for recovering melamine by catalytically degrading melamine resin according to claim 1, wherein: the particle size of the granules in the step is 0.1-10 mm.
3. The method for recovering melamine by catalytically degrading melamine resin according to claim 1, wherein: the reaction time in the step is 60 min-24 h.
4. The method for recovering melamine by catalytically degrading melamine resin according to claim 1, wherein: the catalyst in said step is an acidic catalyst.
5. The method for recovering melamine by catalytically degrading melamine resin according to claim 4, wherein: the acid catalyst is HCl and HNO3、H3BO3、H2SO4、H2CO3、H3PO4、FeCl3、AlCl3、ZnCl2、CuCl2、MnCl2One or more of p-toluenesulfonic acid and dodecylbenzene sulfonic acid are mixed according to any ratio.
6. The method for recovering melamine by catalytically degrading melamine resin according to claim 1, wherein: the solvent in the step is water or a mixed solution of water and an organic reagent, and the organic reagent is specifically one or more of methanol, ethanol, n-propanol, isopropanol, formic acid, acetic acid, tetrahydrofuran, diethyl ether, DMSO, dioxane, DMF, gamma-butyrolactone, gamma-valerolactone, acetone or ethylenediamine which are mixed according to any ratio.
7. The method for recovering melamine by catalytically degrading melamine resin according to claim 6, wherein: the volume ratio of the water to the organic reagent is 1:0.5 to 10.
8. The method for recovering melamine by catalytically degrading melamine resin according to claim 1, wherein: in the step, the mass ratio of the catalyst to the melamine resin is 1: 0.05-5; the mass ratio of the solvent to the melamine resin is 1-100: 1.
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CN104894696A (en) * | 2015-06-29 | 2015-09-09 | 重庆再升科技股份有限公司 | Method for recovering fibers from diaphragmless filter paper edgings |
CN109415531A (en) * | 2016-04-05 | 2019-03-01 | 复合材料科技控股有限责任公司 | The recycling of polymeric matrix composite material |
CN110590534A (en) * | 2019-04-26 | 2019-12-20 | 中国科学院山西煤炭化学研究所 | Method for recovering unsaturated polyester resin waste through selective catalytic degradation |
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EP0528473A2 (en) * | 1991-08-21 | 1993-02-24 | General Motors Corporation | Separator for mat-immobilized-electrolyte battery |
CN102617885A (en) * | 2012-03-28 | 2012-08-01 | 四川大学 | Method for recovering waste thermosetting resin and composite materials thereof through solvents |
CN104672488A (en) * | 2015-02-03 | 2015-06-03 | 中国科学院山西煤炭化学研究所 | Method for degrading and recycling thermosetting epoxy resin material |
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