WO2023153695A1 - Catalyseur et procédé de pyrolyse de résidus de pyrolyse de déchets de polystyrène - Google Patents

Catalyseur et procédé de pyrolyse de résidus de pyrolyse de déchets de polystyrène Download PDF

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Publication number
WO2023153695A1
WO2023153695A1 PCT/KR2023/001393 KR2023001393W WO2023153695A1 WO 2023153695 A1 WO2023153695 A1 WO 2023153695A1 KR 2023001393 W KR2023001393 W KR 2023001393W WO 2023153695 A1 WO2023153695 A1 WO 2023153695A1
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Prior art keywords
residue
pyrolysis
waste polystyrene
catalyst
thermal decomposition
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PCT/KR2023/001393
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English (en)
Korean (ko)
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황동원
윤광남
차승혁
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한국화학연구원
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Publication of WO2023153695A1 publication Critical patent/WO2023153695A1/fr

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    • 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
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/04—Disintegrating plastics, e.g. by milling
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
    • C10G1/10—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal from rubber or rubber waste
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
    • C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B17/00—Recovery of plastics or other constituents of waste material containing plastics
    • B29B17/04—Disintegrating plastics, e.g. by milling
    • B29B2017/0424—Specific disintegrating techniques; devices therefor
    • B29B2017/0496—Pyrolysing the materials
    • 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
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present invention relates to a catalyst and a method for thermally decomposing residual oil obtained by thermally decomposing waste polystyrene, and relates to a catalyst for improving selectivity to cumene and a thermal decomposition method using the catalyst.
  • Polystyrene is a plastic commonly encountered in daily life, such as food containers such as dairy products and disposable cup lids, packaging trays for agricultural and marine products, and styrofoam for packaging home appliances.
  • food containers such as dairy products and disposable cup lids
  • packaging trays for agricultural and marine products and styrofoam for packaging home appliances.
  • styrofoam for packaging home appliances.
  • thermo decomposition As a method of recycling waste polystyrene, a method of thermal decomposition in an appropriate pressure, temperature and inert atmosphere is receiving more attention than simple physical addition or processing.
  • the polymer structure In the case of thermal decomposition, the polymer structure is decomposed to obtain a liquid or gas mixture of hydrocarbons with a low carbon number to be reused as a value-added industrial compound. By reusing, it has advantages from an environmental and economic point of view.
  • Non-Patent Document 1 discloses a residual oil thermal decomposition method in which residual oil generated from thermal decomposition of waste polystyrene is thermally decomposed again using a ZSM-5 zeolite catalyst.
  • styrene monomer, toluene, benzene, and ethylbenzene can be obtained by thermal decomposition of residual oil, and among the thermal decomposition products of residual oil, cumene having a relatively high utilization can be selectively obtained. There is no disclosure of how to do it.
  • Non-Patent Document 2 relates to the selective production of ethylbenzene and benzene by thermal decomposition of polystyrene, and uses USY (ultra-stable Y) zeolite as a catalyst.
  • USY ultra-stable Y
  • the selectivity of ethylbenzene and benzene yield varies depending on the SiO 2 /Al 2 O 3 molar ratio, and when the SiO 2 /Al 2 O 3 molar ratio of USY zeolite is 5.3, it has a high surface area, large pores, and abundant strong acid
  • thermal decomposition of polystyrene pyrolysis residue is not mentioned.
  • Japanese Patent Registration No. 6956187 (2021.10.06.) relates to the conversion of waste plastics into propylene and cumene, which produces benzene and propylene from residual oil by thermally decomposing waste plastics step by step, and synthesizes them to produce cumene.
  • MCM-22 is disclosed as an alkylation catalyst.
  • Patent Document 1 Korean Patent Registration No. 10-0468047 (2005.01.14.)
  • Patent Document 2 Japanese Patent Registration No. 6956187 (2021.10.06.)
  • Non-Patent Document 1 Korean J. Chem. Eng., 20(1), (2003)0 133-137
  • Non-Patent Document 2 J. Wang, et al. Energy Conversion and Management 200 (2019) 112088
  • the inventors of the present invention go beyond the conventional pyrolysis technology of waste polystyrene to pyrolyze the residue produced during the pyrolysis to reduce environmental pollution and improve economic efficiency, as well as to selectively remove cumene from the products produced through the pyrolysis of the residue. It is intended to provide a method for manufacturing.
  • the present invention includes ultra-stable Y zeolite (USY), and a catalyst for thermal decomposition of waste polystyrene pyrolysis residue oil, characterized in that it has a higher selectivity for cumene than other pyrolysis products.
  • the molar ratio of SiO 2 /Al 2 O 3 of the ultra-stable Y-zeolite may be in the range of greater than 5 and less than or equal to 10.
  • the present invention is a catalyst for thermally decomposing waste polystyrene pyrolysis residue in the presence of 2-propanol to selectively form cumene, characterized in that it includes a zeolite having an MWW structure.
  • a catalyst for the pyrolysis reaction of polystyrene pyrolysis residue is provided.
  • the present invention provides a method for thermal decomposition of waste polystyrene pyrolysis residue, characterized in that the selectivity of cumene is higher than that of other pyrolysis products by using a catalyst containing ultra-stable Y-zeolite.
  • the ultra-stable Y-zeolite catalyst may be included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the residue oil, and the thermal decomposition temperature of the residue oil may be 275 to 350 °C.
  • the present invention is another method of thermally decomposing waste polystyrene pyrolysis residue, which is thermally decomposed by contacting with MWW structured zeolite in the presence of 2-propanol to increase the selectivity of cumene among pyrolysis products. to provide.
  • the thermal decomposition temperature of the waste polystyrene pyrolysis residue may be 275 to 350 ° C
  • the MWW structure zeolite is 1 to 50 parts by weight based on 100 parts by weight of the residue
  • the 2-propanol is 100 parts by weight of the residue. It may be from 1 to 10 parts by weight.
  • waste polystyrene pyrolysis residue can be pyrolyzed into useful components, which is advantageous in terms of environmental pollution and economy.
  • 1 is a graph showing components of residual oil obtained by thermal decomposition of waste polystyrene according to an embodiment of the present invention analyzed by gas chromatography.
  • FIG 3 is a graph showing product distribution according to the SiO 2 /Al 2 O 3 molar ratio of the ZSM-5 catalyst according to an embodiment of the present invention.
  • FIG. 4 is a product distribution graph in the case of pyrolysis of residual oil including a catalyst and 2-propanol according to an embodiment of the present invention.
  • FIG. 5 is a product distribution graph in the case of pyrolysis of residual oil including only a catalyst without 2-propanol according to an embodiment of the present invention.
  • the present invention goes further than the prior art of recovering styrene monomer by thermally decomposing waste polystyrene, and further reduces environmental pollution by thermally decomposing again without incinerating or discarding the residual oil generated in large quantities during the thermal decomposition of the waste polystyrene.
  • a catalyst for pyrolysis of waste polystyrene pyrolysis residue oil and a method for pyrolysis of waste polystyrene pyrolysis residue oil capable of increasing the selectivity of cumene among products resulting from proprietary pyrolysis are provided.
  • the thermal decomposition residue of the waste polystyrene is not completely thermally decomposed in the process of depolymerizing the waste polystyrene into styrene monomer or the like or thermally decomposing it into industrially useful compounds such as benzene, styrene, cumene, etc. means a substance that does not
  • ultra-stable Y-zeolite USY is used as the thermal decomposition catalyst.
  • the USY is a type of Y-type zeolite, which is a Y-type zeolite having a SiO 2 /Al 2 O 3 molar ratio of > 5 in which aluminum is removed from the Y-type zeolite framework by high-temperature heat treatment or dealumination of aluminum-rich Y-type zeolite under steam. am. USY exhibits higher thermal and hydrothermal stability and higher catalytic activity than conventional aluminum-rich Y zeolites.
  • USY in a catalyst for thermal decomposition of residual oil from thermal decomposition of waste polystyrene, USY can be used to increase the selectivity of cumene.
  • the molar ratio of SiO 2 /Al 2 O 3 of USY may be in the range of more than 5 and less than 10.
  • the conversion rate of residue oil and the selectivity to cumene are maintained high.
  • the present invention provides a thermal decomposition method for obtaining a thermal decomposition product containing cumene by thermally decomposing waste polystyrene pyrolysis residue.
  • the pyrolysis method is performed using ultra-stable Y-zeolite, and the content of the catalyst may be in the range of 1 to 50 parts by weight, preferably 3 to 10 parts per 100 parts by weight of the waste polystyrene pyrolysis residue.
  • the thermal decomposition of the residue may be insignificant, and if it is more than 50 parts by weight, the increase in thermal decomposition rate is not large even for the added catalyst, which is not efficient.
  • the thermal decomposition of the waste polystyrene pyrolysis residue may be performed in the range of 275 to 350 °C. Thermal decomposition may not occur when the temperature is lower than 275 °C, and yield of cumene may decrease due to excessive thermal decomposition when the temperature is higher than 350 °C.
  • the pressure during the pyrolysis may be 1 to 10 atm. When the pressure is less than 1 atm, thermal decomposition may not occur, and when the pressure is greater than 10 atm, the increase in thermal decomposition rate is not large and is not efficient.
  • the step of pyrolyzing waste polystyrene can be performed by a general pyrolysis method of waste polystyrene, so the method is not limited, and the content of waste polystyrene, phase form (liquid phase, solid phase, gas phase) of the product by pyrolysis, etc.
  • the thermal decomposition temperature, thermal decomposition time, heating rate, moisture content, etc. may be varied.
  • the present invention provides a method for thermally decomposing waste polystyrene pyrolysis residue in the coexistence of 2-propanol as a method for thermal decomposition of waste polystyrene pyrolysis residue.
  • a zeolite having an MWW structure is used as a catalyst for thermally decomposing waste polystyrene pyrolysis residue in the presence of 2-propanol.
  • the MWW structured zeolite is one of the zeolite framework topologies that exist in a lamellar form. It is multi-layered, containing two independent pore systems consisting of a pore system and a pore system containing a large 12-MR giant cage coupled with a 10-MR window.
  • This MWW structured zeolite is a crystalline molecular sieve with an X-ray diffraction pattern comprising d-spacing maxima of 12.4 ⁇ 0.25, 6.9 ⁇ 0.15, 3.57 ⁇ 0.07 and 3.42 ⁇ 0.07 ⁇ .
  • the zeolite of the MWW structure according to the present invention is, but is not limited to, MCM-22, PSH-3, SSZ-25, ERB-1, ITQ-1, ITQ-2, MCM-36, MCM-49, MCM-56, It may be UZM-8 and a mixture thereof, preferably MCM-22.
  • the selectivity of cumene among thermal decomposition products of the residual oil is increased by using the zeolite having the MWW structure.
  • the MWW structured zeolite is included in an amount of 1 to 50 parts by weight, preferably 3 to 10 parts by weight, based on 100 parts by weight of the waste polystyrene pyrolysis residue oil. If it is less than 1 part by weight, the thermal decomposition reaction does not occur efficiently, resulting in a decrease in the amount of benzene produced, resulting in a problem that the production of cumene may be lowered. There are possible concerns.
  • the SiO 2 /Al 2 O 3 molar ratio of the MWW structured zeolite is not significantly involved, but is generally preferably in the range of 10 to 50.
  • the 2-propanol may be 1 to 10 parts by weight, preferably 2.5 to 5 parts by weight, based on 100 parts by weight of the residue oil.
  • the amount of 2-propanol is less than 1 part by weight, the production of cumene is low due to the lack of 2-propanol, and when it exceeds 10 parts by weight, the amount of cumene produced is not large even with respect to the added 2-propanol, which is not efficient.
  • the pyrolysis temperature of the waste polystyrene pyrolysis residue oil in the state in which 2-propanol is contained may be 275 to 350 °C, preferably 300 to 325 °C.
  • the thermal decomposition temperature is in the range of 275 ° C to 350 ° C, the production of cumene is high.
  • Waste styrofoam discharged from households is volume-reduced and pulverized, and thermally decomposed at 400 ° C for 1 hour to separately collect compounds having a boiling point below 180 ° C, such as benzene, toluene and styrene, and obtain the remaining waste polystyrene pyrolysis residue.
  • the prepared residue was injected into a reactor and thermally decomposed at 300 °C and 1 atm (N 2 ) for 1 hour at 500 rpm using 5 wt% of an ultra-stable Y-zeolite catalyst.
  • the molar ratio of SiO 2 /Al 2 O 3 of the ultra-stable Y-zeolite catalyst was changed to 5.1, 5.2, 30, and 80.
  • the residue was thermally decomposed in the same manner as in Experimental Example 1, except that ZSM5 (CBV-3024E) was used as a zeolite catalyst and the SiO 2 /Al 2 O 3 molar ratio was set to 23, 30, 50, and 280.
  • ZSM5 CBV-3024E
  • SiO 2 /Al 2 O 3 molar ratio was set to 23, 30, 50, and 280.
  • FIG. 2 shows the product yield distribution of residual oil according to the SiO 2 /Al 2 O 3 molar ratio of ultra-stable Y-zeolite in thermal decomposition of residue rate by ultra-stable Y-zeolite catalyst.
  • a-MS means alpha methyl styrene.
  • the product distribution of the residual oil varies according to the SiO 2 /Al 2 O 3 ratio of the ultra-stable Y-zeolite catalyst, and when the SiO 2 /Al 2 O 3 ratio is 5.1 and 5.2 wt%, cumene is It is produced at a remarkably high rate with a yield of 40 wt%.
  • the benzene selectivity is generally high.
  • the selectivity of cumene is high.
  • the residual oil was pyrolyzed in the same manner as in Experimental Example 4 except that 2-propanol was not used, and the results are shown in FIG. 5 .

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  • Chemical & Material Sciences (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
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  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne un catalyseur de pyrolyse d'un résidu obtenu par pyrolyse de déchets de polystyrène, et un procédé de pyrolyse, caractérisé en ce qu'une zéolite Y ultra-stable (zéolite USY) est utilisée en tant que catalyseur, ou qu'une zéolite ayant une structure MWW est incluse conjointement avec du 2-propanol de telle sorte que la sélectivité du cumène, parmi des produits de pyrolyse de résidus obtenus par pyrolyse de résidus obtenus par pyrolyse de déchets de polystyrène, est augmentée.
PCT/KR2023/001393 2022-02-11 2023-01-31 Catalyseur et procédé de pyrolyse de résidus de pyrolyse de déchets de polystyrène WO2023153695A1 (fr)

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KR10-2022-0018030 2022-02-11
KR1020220018030A KR20230121317A (ko) 2022-02-11 2022-02-11 폐폴리스티렌 열분해 잔사유를 열분해하는 촉매 및 방법

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110082160A (ko) * 2008-10-06 2011-07-18 바져 라이센싱 엘엘씨 큐멘의 제조방법
JP6956187B2 (ja) * 2017-01-05 2021-11-02 サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ 廃棄プラスチックのプロピレンおよびクメンへの変換
KR20210150277A (ko) * 2020-06-03 2021-12-10 에스케이이노베이션 주식회사 폐유분의 2차 열분해를 통한 선택적 납사 유분 제조방법
WO2022023262A1 (fr) * 2020-07-30 2022-02-03 IFP Energies Nouvelles Procede de traitement d'huiles de pyrolyse de plastiques incluant un hydrocraquage en une etape

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100468047B1 (ko) 2002-04-12 2005-01-24 한국화학연구원 폐폴리스티렌으로부터 스티렌모노머의 회수방법

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110082160A (ko) * 2008-10-06 2011-07-18 바져 라이센싱 엘엘씨 큐멘의 제조방법
JP6956187B2 (ja) * 2017-01-05 2021-11-02 サビック グローバル テクノロジーズ ベスローテン フェンノートシャップ 廃棄プラスチックのプロピレンおよびクメンへの変換
KR20210150277A (ko) * 2020-06-03 2021-12-10 에스케이이노베이션 주식회사 폐유분의 2차 열분해를 통한 선택적 납사 유분 제조방법
WO2022023262A1 (fr) * 2020-07-30 2022-02-03 IFP Energies Nouvelles Procede de traitement d'huiles de pyrolyse de plastiques incluant un hydrocraquage en une etape

Non-Patent Citations (1)

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Title
REHAN M.; MIANDAD R.; BARAKAT M.A.; ISMAIL I.M.I.; ALMEELBI T.; GARDY J.; HASSANPOUR A.; KHAN M.Z.; DEMIRBAS A.; NIZAMI A.S.: "Effect of zeolite catalysts on pyrolysis liquid oil", INTERNATIONAL BIODETERIORATION & BIODEGRADATION, ELSEVIER, AMSTERDAM , NL, vol. 119, 27 December 2016 (2016-12-27), Amsterdam , NL , pages 162 - 175, XP029956637, ISSN: 0964-8305, DOI: 10.1016/j.ibiod.2016.11.015 *

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