WO2019072105A1 - Polymère réticulé à base de déchets de polystyrène, procédé de préparation s'y rapportant et son application - Google Patents

Polymère réticulé à base de déchets de polystyrène, procédé de préparation s'y rapportant et son application Download PDF

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WO2019072105A1
WO2019072105A1 PCT/CN2018/108310 CN2018108310W WO2019072105A1 WO 2019072105 A1 WO2019072105 A1 WO 2019072105A1 CN 2018108310 W CN2018108310 W CN 2018108310W WO 2019072105 A1 WO2019072105 A1 WO 2019072105A1
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crosslinked polymer
waste polystyrene
polystyrene
preparing
reaction
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Chinese (zh)
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刘长坤
伏振宇
雷晓斌
贾继珍
王琳
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Shenzhen University
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Shenzhen University
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/02—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by adsorption, e.g. preparative gas chromatography
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
    • B01J20/267—Cross-linked polymers
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/504—Carbon dioxide
    • 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
    • C08J2325/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Derivatives of such polymers
    • C08J2325/02—Homopolymers or copolymers of hydrocarbons
    • C08J2325/04—Homopolymers or copolymers of styrene
    • C08J2325/06—Polystyrene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • the invention relates to the field of porous solid adsorbing materials, in particular to a crosslinked polymer based on waste polystyrene and a preparation method and application thereof.
  • the carbon capture methods of carbon dioxide produced after the combustion of fossil energy mainly include: physical absorption method, membrane separation method, chemical absorption method and the like.
  • physical absorption method using a porous solid material as an absorbent has attracted attention.
  • the use of solid porous materials as adsorbents to capture carbon dioxide in exhaust gas has many advantages: (1) low energy consumption, the adsorption of carbon dioxide by solid porous materials generally adopts pressure swing adsorption and temperature swing adsorption, and the treatment process is divided into capture and separation.
  • the first step is to capture the carbon dioxide in the exhaust gas by using a large amount of carbon dioxide adsorption under high pressure or low temperature conditions, and to separate the carbon dioxide adsorbed in the material under a low pressure or high temperature condition, and the material continuously reciprocates. Used to handle large amounts of exhaust gas. This can reduce the energy consumption during the capture process; at the same time, the choice of solid materials to capture carbon dioxide avoids the energy consumption caused by the absorption of heat by the water solvent during regeneration. (2) It is easy to operate, and the solid material acts as an adsorbent, which avoids the corrosion of the alkaline organic solution on the equipment, and the operation and maintenance process is simple. (3) The solid adsorbent material has a larger adsorption amount of carbon dioxide relative to ethanolamine, which is attributed to the material having a large specific surface area and pore volume, and can capture a large amount of carbon dioxide.
  • porous solid materials In recent years, significant research results have been achieved in the design and synthesis of porous solid materials.
  • the main porous solid adsorbent materials are currently concentrated in zeolites, silica, metal organic frameworks (MOFs), high molecular polymers and carbon-based materials.
  • MOFs metal organic frameworks
  • the synthesis of most materials requires careful design of the structure of the reactants and selection of specific reaction pathways.
  • expensive transition metal catalysts or toxic solvents are often used in the preparation of porous solid materials. These factors increase the production cost of materials, which restricts the industrial production of porous solid materials and its large-scale application in carbon dioxide adsorption, capture and storage.
  • the object of the present invention is to provide a crosslinked polymer based on waste polystyrene and a preparation method and application thereof, aiming at solving the complicated preparation method, high cost and environment of the existing porous solid material. Unfriendly and other issues.
  • a method for preparing a crosslinked polymer based on waste polystyrene comprising:
  • Step A according to the weight percentage, waste polystyrene 1-6%, organic solvent 80-90%, cross-linking agent 1-6%, catalyst 2-8% mixed, under a protective atmosphere, stirring at room temperature for 10-50 min And then heated to 80-90 ° C reaction 6-24h;
  • Step B in the solution after the reaction in the step A, the reaction is terminated by adding an alcohol solution (for example, methanol or ethanol solution), then cooled to room temperature and purified to obtain a crosslinked polymer.
  • an alcohol solution for example, methanol or ethanol solution
  • the crosslinking agent is carbon tetrachloride, dimethoxymethane, p-dichlorobenzyl or p-dichloro One of methylbiphenyl and m-trichlorotoluene.
  • the catalyst is one of FeCl 3 and AlCl 3 .
  • the organic solvent is toluene, o-xylene, ethylbenzene, dichloromethane, dichloroethane, chloroform and One of p-nitrobenzene.
  • the method for preparing a crosslinked polymer based on waste polystyrene wherein the concentration of the alcohol solution in the step B is 40-60 V/V%.
  • the purification treatment is specifically: filtering the cooled reaction solution, and then washing with ethanol and a dilute hydrochloric acid solution respectively. And washed with deionized water until the filtrate is colorless. Finally, the filtrate is extracted with a Soxhlet extractor containing methanol for 18-30 h, dried, and then vacuum dried at 40-60 ° C for 18-30 h.
  • a crosslinked polymer based on waste polystyrene produced by any of the preparation methods described above.
  • the crosslinked polymer based on waste polystyrene has a microporous structure.
  • the present invention provides a method for preparing a crosslinked polymer based on waste polystyrene as described above, which uses waste polystyrene as a main raw material, which is not only widely used, low in cost, simple in reaction operation, and easy to control. Moreover, it provides an effective way for the recycling of waste polystyrene and expands its application range.
  • the invention adopts a crosslinking agent and is supplemented by a catalyst, and the polystyrene forms a highly crosslinked three-dimensional structure through one-step reaction.
  • the three-dimensional network porous structure can be applied to the field of solid adsorbent materials.
  • Figure 1 is a photograph of waste polystyrene foam
  • FIG. 2 is a scanning electron micrograph of a crosslinked polymer obtained by reacting dichloroethane as a solvent while acting as a crosslinking agent and a waste polystyrene foam;
  • 3 is a scanning electron microscope image of an ultra-highly crosslinked polymer obtained by reacting carbon tetrachloride as a crosslinking agent with waste polystyrene foam;
  • Figure 4 is a scanning electron micrograph of an ultrahigh crosslinked polymer obtained by reacting dimethoxymethane as a crosslinking agent with waste polystyrene foam;
  • Figure 5 is a scanning electron micrograph of an ultra-highly crosslinked polymer obtained by reacting p-dichlorobenzyl as a crosslinking agent with waste polystyrene foam;
  • Figure 6 is a scanning electron micrograph of an ultra-high cross-linked polymer obtained by reacting p-dichloromethylbiphenyl as a crosslinking agent with waste polystyrene foam;
  • HCP-A is a Fourier transform attenuated total reflection infrared spectrum of HCP-A, HCP-B, HCP-C, HCP-D, and commercial polystyrene (PS) prepared in Examples 1, 2, 3, and 4;
  • Figure 9 is a thermogravimetric analysis chart of HCP-A, HCP-B, HCP-C, HCP-D and commercial polystyrene prepared in Examples 1, 2, 3, and 4 (test conditions: N 2 atmosphere, heating rate) 10 ° C / min);
  • HCP-A is a pore size distribution diagram of HCP-A, HCP-B, HCP-C, and HCP-D prepared in Examples 1, 2, 3, and 4;
  • Figure 11 is an adsorption isotherm of carbon dioxide adsorption at 273K for HCP-A, HCP-B, HCP-C and HCP-D prepared in Examples 1, 2, 3, and 4;
  • Figure 12 is an adsorption isotherm of nitrogen gas at 273 K for HCP-A, HCP-B, HCP-C and HCP-D prepared in Examples 1, 2, 3, and 4.
  • the present invention provides a crosslinked polymer based on waste polystyrene, a preparation method and application thereof, and the present invention will be further described in detail below in order to make the objects, technical solutions and effects of the present invention more clear and clear. It is understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
  • the invention provides a preferred embodiment of a method for preparing a crosslinked polymer based on waste polystyrene, the preparation process is as follows:
  • the cleaned waste polystyrene 4%, the organic solvent dichloroethane 86%, the crosslinker dimethoxymethane 4% and the catalyst AlCl 3 6% are added to the reaction vessel, and then loaded
  • the thermometer and the condenser were placed in a protective atmosphere (such as nitrogen), stirred at room temperature for 30 min, and then heated to 85 ° C for 16 h.
  • the reaction was terminated by adding 50% ethanol solution, and cooled to room temperature, then the solution was filtered using a Buchner funnel, rinsed with ethanol and 1% hydrochloric acid, respectively, and then washed with deionized water until The filtrate was colorless, and the filtrate was extracted with a Soxhlet apparatus containing methanol for 24 hours, taken out to dry, and then dried in a vacuum oven at 50 ° C for 24 hours to obtain a crosslinked polymer.
  • Polystyrene is a long-standing plastic product with good water resistance, chemical resistance, heat insulation, etc. It is low in cost and widely used. According to statistics, the production of polystyrene is second only to polyethylene and polyvinyl chloride, ranking third in plastics production. Since the rigid skeleton structure of polystyrene is difficult to degrade under natural conditions, increasing waste such as polystyrene has caused serious "white pollution". In order to reduce the environmental hazard of waste plastics, the traditional disposal methods of waste polystyrene mainly include: landfill, incineration and reuse. In developed countries in Europe, the proportion of recycled plastics recycled is only 30%. In developing countries, the recycling rate of polystyrene is lower due to the lack of corresponding equipment and facilities.
  • the present invention prepares a porous solid adsorbent by using waste polystyrene as a main raw material, which not only has wide source and low cost, but also provides an effective way for recycling waste polystyrene, and is beneficial to the protection of the ecological environment.
  • waste polystyrene has been partially applied in the process of resource (such as: heat insulating material, water reducing agent, adhesive, etc.), and the invention expands its application range.
  • the waste polystyrene undergoes a Friedel-Crafts reaction under the action of a catalyst and a crosslinking agent, wherein the benzene rings are cross-linked to form a three-dimensional network-like porous microstructure. It is capable of adsorbing CO 2 .
  • the invention synthesizes the porous solid adsorbent material through one-step reaction, and solves the problem that the traditional synthetic porous solid adsorbent material consumes expensive transition metal catalyst and cannot be industrialized.
  • the obtained reactant is crosslinked compared to the waste polystyrene material (as shown in FIG. 1), but Loose irregular spherical particles (as shown in Figure 2); and additional cross-linking agents in carbon tetrachloride, dimethoxymethane, p-dichlorobenzyl, p-dichloromethylbiphenyl and trichlorotoluene
  • the obtained reactant exhibits a highly crosslinked state (as shown in FIG. 3, FIG. 4, FIG. 5, FIG. 6). Therefore, the cross-linking structure of the ultra-highly crosslinked polymer is selected by the cross-linking agent selected by the present invention. The formation has a significant impact.
  • the crosslinked polymer based on waste polystyrene prepared according to the present invention has good chemical stability, and is specifically characterized by being insoluble in common organic solvents (such as N, N-dimethylformamide, dimethyl sulfoxide, Tetrahydrofuran, toluene, etc.) and 1 mol/L hydrochloric acid and 1 mol/L sodium hydroxide solution.
  • the crosslinked polymer has good thermal stability, and at 443 ° C (the temperature at which the waste polystyrene is completely decomposed in the thermogravimetric analysis), only 13-28% of the ultrahigh crosslinked polymer is decomposed.
  • the BET specific surface area is up to 777m 2 /g
  • the specific surface area of micropores is up to 382m 2 /g
  • the pore volume is up to 1.15cm 3 /g
  • the average pore diameter is 3.11-6.86nm
  • the pore size distribution is concentrated in the microporous region. And mesoporous areas.
  • the invention also provides the use of a crosslinked polymer as described above.
  • HCP-A has good chemical stability, which is insoluble in common organic solvents (such as N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, toluene, etc.) and 1 mol/L hydrochloric acid and 1 mol. / L sodium hydroxide solution.
  • HCP-A has good thermal stability. At 443 ° C (the temperature at which polystyrene is completely decomposed in the thermogravimetric analysis (Fig. 9 (e) curve)), only 27.7% of HCP-A is decomposed (Fig. 9 (a) curve).
  • HCP-B has good chemical stability, which is insoluble in common organic solvents (such as N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, toluene, etc.) and 1 mol/L hydrochloric acid and 1 mol. / L sodium hydroxide solution.
  • HCP-B has good thermal stability. At 443 ° C (thermal weight analysis, the temperature at which polystyrene is completely decomposed), only 15.92% of the ultra-high crosslinked polymer HCP-B is decomposed ( Figure 9 ( b) curve).
  • the BET specific surface area is 768 m 2 /g
  • the specific pore surface area is 293 m 2 /g
  • the pore volume is 0.60 cm 3 /g
  • the average pore diameter is 3.11 nm
  • the pore size distribution is concentrated in the micropore region and the mesoporous region (Fig. 10 (b) Curve).
  • the adsorption amount of CO 2 was 2.149 mmol/g (Fig. 11 (b) curve), and the adsorption amount to N2 was 0.1624 mmol/g (Fig. 12 (b) curve); for CO 2
  • HCP-C has good chemical stability, which is insoluble in common organic solvents (such as N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, toluene, etc.) and 1 mol/L hydrochloric acid and 1 mol. / L sodium hydroxide solution.
  • HCP-C has good thermal stability. At 443 °C (the temperature at which the polystyrene is completely decomposed in the thermogravimetric analysis), only 18.26% of the ultrahigh crosslinked polymer HCP-C is decomposed (Fig. 9 ( c) curve).
  • waste syndiotactic polystyrene (WSPS) particles are recovered, washed with ethanol solution and deionized water, and dried in an oven for later use;
  • Abandoned syndiotactic polystyrene particles 4g are separately added to the reaction vessel.
  • HCP-D waste polystyrene-based ultra-high cross-linking polymerization.
  • HCP-D The Fourier transform attenuated total reflection infrared spectrum (ATR-FTIR) of HCP-D (Fig. 7 (d) curve) and carbon nuclear magnetic resonance spectrum (13C NMR) (Fig. 8 (d) curve) were successfully confirmed. Preparation of the ultrahigh crosslinked polymer.
  • HCP-D has good chemical stability, which is insoluble in common organic solvents (such as N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, toluene, etc.) and 1 mol/L hydrochloric acid and 1 mol. / L sodium hydroxide solution.
  • HCP-D has good thermal stability. At 443 ° C (thermal weight analysis, the temperature at which polystyrene is completely decomposed), only 14.22% of the ultra-high crosslinked polymer HCP-D is decomposed ( Figure 9 ( d) curve).
  • the present invention provides a crosslinked polymer based on waste polystyrene, a preparation method and application thereof, and the invention adopts waste polystyrene as a main raw material, which is not only widely used, low in cost, but also discarded.
  • the recycling of polystyrene provides an effective way to protect the ecological environment and expand its application range.
  • the invention adopts a cross-linking agent and is supplemented by a catalyst, and the polystyrene forms a high degree of cross-linking through one-step reaction.
  • the three-dimensional network porous structure can be used in the field of solid adsorbent materials, and solves the problem that the conventional synthetic porous solid adsorbent material consumes expensive transition metal catalyst and cannot be industrialized.
  • the crosslinked polymer of the invention has good chemical stability, and is specifically: insoluble in common organic solvents (such as N, N-dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, toluene, etc.) and 1 mol/L. Hydrochloric acid and 1 mol/L sodium hydroxide solution.
  • the crosslinked polymer of the present invention has good thermal stability at the same time. At 443 ° C (the temperature at which the polystyrene is completely decomposed in the thermogravimetric analysis), only 13-28% of the ultrahigh crosslinked polymer is decomposed.
  • the BET specific surface area is up to 777m 2 /g
  • the specific surface area of micropores is up to 382m 2 /g
  • the pore volume is up to 1.15cm 3 /g
  • the average pore diameter is 3.11-6.86nm
  • the pore size distribution is concentrated in the microporous region. And mesoporous areas.
  • the adsorption selectivity in the mixed gas is up to 37.8, which can be applied to the absorption and separation of CO 2 in the factory flue gas.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

Abstract

L'invention concerne un polymère réticulé à base de déchets de polystyrène, un procédé de préparation s'y rapportant et une application de celui-ci. Le procédé de préparation comprend : l'étape A, le mélange de 1 à 6 % de déchets de polystyrène, de 80 à 90 % de solvant organique, de 1 à 6 % d'agent de réticulation et 2 à 8 % de catalyseur en pourcentage en poids et l'agitation du mélange à température ambiante pendant 10 à 50 min dans une atmosphère protectrice, puis le chauffage du mélange à 80 à 90°C pour qu'il réagisse pendant 6 à 24 h; et l'étape B, l'ajout d'une solution alcoolique dans la solution après la réaction dans l'étape A pour arrêter la réaction, puis le refroidissement du mélange à la température ambiante et la purification du mélange pour obtenir le polymère réticulé. Dans la présente invention, des déchets de polystyrène sont utilisés en tant que matière première, et donc les coûts sont faibles, et une manière efficace est proposée pour le recyclage des déchets de polystyrène; de plus, un agent de réticulation et un catalyseur sont utilisés, le polystyrène forme une structure poreuse à réseau tridimensionnel hautement réticulée au moyen d'une réaction en une seule étape et la structure poreuse à réseau tridimensionnel peut être appliquée au domaine des matériaux d'adsorption solides.
PCT/CN2018/108310 2017-10-10 2018-09-28 Polymère réticulé à base de déchets de polystyrène, procédé de préparation s'y rapportant et son application Ceased WO2019072105A1 (fr)

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