WO2023228034A1 - Catalyseur et procédé d'obtention de bhet à partir de pet - Google Patents

Catalyseur et procédé d'obtention de bhet à partir de pet Download PDF

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Publication number
WO2023228034A1
WO2023228034A1 PCT/IB2023/055212 IB2023055212W WO2023228034A1 WO 2023228034 A1 WO2023228034 A1 WO 2023228034A1 IB 2023055212 W IB2023055212 W IB 2023055212W WO 2023228034 A1 WO2023228034 A1 WO 2023228034A1
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Prior art keywords
bhet
pet
catalyst
activated carbon
ethylene glycol
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PCT/IB2023/055212
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English (en)
Spanish (es)
Inventor
Gabriel Jaime Cano Ospina
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Ingbiocomb Sas
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Publication of WO2023228034A1 publication Critical patent/WO2023228034A1/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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • 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
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/745—Iron
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/297—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C07C69/82—Terephthalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/88—Post-polymerisation treatment
    • 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
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/16—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with inorganic material
    • 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
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
    • C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
    • C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups

Definitions

  • the present invention is related to the field of plastic recycling, more particularly with the recycling of Polyethylene Terephthalate, and with catalysts developed expressly for this purpose.
  • PET also known as polyethylene terephthalate
  • PET was first produced in 1941 and was patented as a polymer for the production of fibers by British scientists J. R. Whinfield and J. T. Dickson in that same year. This arises as a pressing need to look for substitutes for the cotton that came from Egypt due to the global situation such as the Second World War.
  • polyester fiber began in 1955 and it is from 1976 when PET began to be used for the manufacture of light, transparent and resistant containers mainly for beverages, such as for bottling mineral water and soft drinks. carbonated and already, by the year 2000 it began to be used for packaging beer [1].
  • PET has diversified into multiple sectors, replacing traditionally implemented materials or proposing new packaging alternatives that were unthinkable until now. This important diversification has meant that PET has experienced great growth in its consumption and continues to be the packaging material that currently has the highest growth expectations worldwide.
  • PET is a plastic polymer that is obtained through a polymerization process of Terephthalic acid and Ethylene Glycol. It is a linear polymer, with a high degree of crystallinity and thermoplastic in its behavior, which makes it suitable for being transformed through extrusion, injection, injection-blowing and thermoforming processes.
  • PET is a resin that belongs to the polyester family, whose name is attributed to the fact that it contains the ester chemical group in various positions. Its chemical production or synthesis is carried out through two stages:
  • BHET Bis (2) Hydroxyethylene Terephthalate
  • DMT Dimethyl Terephthalate
  • EG Ethylene Glycol
  • TPA terephthalic acid
  • EG Ethylene Glycol
  • the second stage of PET production the polycondensation reaction of the bis (2) Hydroxyethylene Terephthalate (BHET) monomer, is carried out in two stages: 1.
  • Molten polycondensation (MPP) during which an increase in the length of the polymer chain or the degree of polymerization takes place.
  • the reaction is carried out at high temperatures, in a range between 260 and 290°C.
  • catalysts is essential for polymerization to take place; to obtain acceptable molecular weights, antimony catalysts are generally used; The most common is antimony trioxide (Sb2Ü3) or antimony triacetate, which allows obtaining a degree of esterification of 90%.
  • the BHET monomer obtained from the estehficator system is pumped to the polymerization reactors, where a polymer is obtained with a viscosity range between 0.45 and 0.65 deciliter/grams, with a content between 30 and 150 ppm of acetaldehyde.
  • a polymer is obtained with a viscosity range between 0.45 and 0.65 deciliter/grams, with a content between 30 and 150 ppm of acetaldehyde.
  • the polymer in the molten state becomes solid particles and is crystallized through a previous pelletizing system, which has an important effect on the size, shape, density, water content, degree of crystallinity and fines in the polyester pellet [3 ].
  • SSP Solid State Polycondensation
  • MMP molten phase polycondensation
  • Plastic has characteristics that make it attractive from the point of view of use and manufacturing. Being lightweight, it is easy to transport over long distances, resistant to breakage, and most microorganisms have not evolved to use plastic as a source of food, which attributes microbiological healthiness to the contents stored there [4],
  • Plastic pollution has recently been found in freshwater lakes, inland seas, rivers, wetlands and organisms from plankton to whales [4]. Human beings, being at the top of the trophic pyramid, are not exempt. of the dangers posed by this serious contamination.
  • plastic fragments are ingested by animals, contaminating the food chain on which we depend, especially due to the toxic additives in plastic, such as the powerful endocrine disruptor Bisphenol.
  • Glycolysis without the presence of a catalyst is an extremely slow process; many researches have focused on increasing the speed of the reaction of metal salts.
  • a salt is used in a liquid state that has a melting point below 100 °C, an example of this is NaCL.
  • Heterogeneous catalyzed glycolysis the research point of our project, consists of supporting a metal by means of some technique such as impregnation, precipitation, co-precipitation or ultrasound, on a porous solid with a large surface area.
  • Shukla et al report the addition of a catalyst in the form of zeolites, zeolites are catalysts that have good catalytic activity due to their large area.
  • Imran et al studied the glycolysis of post-consumer PET in the presence of metal oxides impregnated on different silica supports, silica nanoparticles (SNPs) 304, ZnO/SNPs having a high monomer production > 90%), this It is due to the high surface area, the porous and amorphous structure and the existence of numerous sites.
  • Imran et al. have also studied this reaction mechanism with a catalyst in the form of spinels of metal oxides (C03O4 and Mn3Ü4) and mixed metal oxides (ZnMn2Ü4, CoMn204 and ZnCo204) prepared by precipitation and co-precipitation methods. The results revealed that the catalyst that had the highest BHET production (92.2 mol %) was under conditions 2C).
  • the purified BHET monomer is polymerized into polyethylene terephthalate that meets food contact specifications, using known polymerization processes.
  • the present invention is a process for recycling colored polyester thereby producing purified white polyester suitable for food grade uses.
  • the present invention is a method for removing dyes from polyester for recycling that comprises: a) depolyming polyester by adding glycol to said polyester to produce a glycolized monomer; b) optionally filtering contaminants from said glycolized monomer; c) put in contact said monomer glycolized with activated carbon to remove some colorant; d) extracting the remaining dye by adding water, methanol or glycol to said glycolized monomer; and e) separating said glycolized monomer from said water, methanol or glycol with said remaining colorant thereby producing white glycolized monomer.
  • Japanese patent No. JP6964101 entitled “Method of depolymerization of polyester containing opaque polyethylene terephthalate", which is incorporated herein in its entirety by way of reference, teaches a method for depolymerizing a material polyester raw material containing opaque PET, wherein the raw material comprises 0.1% to 10% by weight of pigment, and the method comprises at least the following steps: a) The step of adjusting the polyester raw material to which can be heated and pressurized according to the operating conditions of the subsequent depolymerization step b). The polyester raw material is heated to a temperature of 225 to 275 ° C.
  • Step a) includes an extrusion section, which is used to extrude; b) A step of supplying a diol to the effluent of step a) and depolyming by glycolysis by the contribution of this diol to obtain a monomer and an oligomer, which is carried out at a temperature of 200 to 400°C and The polyester . 1 to 20 mol of diol per mol of diester in the raw material, the residence time of polyester is 0.1 to 5 hours, PET is converted into BHET monomer and BHET oligomer; c) A step of total or partial separation of the diol from the effluent of step b), carried out at a temperature of 100-250°C.
  • step b) A step of separating a liquid effluent rich in monomers from step c) into an effluent of heavy impurities and a pre-pumped monomer effluent, at a temperature less than 250°C and less than 0.001 MPa.
  • the liquid residence time is less than 10 minutes; and e) the discoloration of the pre-puffed monomer effluent, at a temperature of 100-250°C and 0.1 -1.
  • a method comprising a step of being performed at a pressure of 0.0 MPa in the presence of an adsorbent to produce a purified monomer effluent.
  • Chinese patent application No. CN105367425 entitled “Purification system by chemical method for preparing BHET monomer from waste PAT material", which is incorporated herein in its entirety by way of reference, teaches a purification system for a chemical method to prepare a BHET monomer from a waste PET (polyethylene terephthalate) material.
  • a BHET quantitative feed system is connected to an inlet of a hydrolysis and filtration system through of a pipe; an outlet of the hydrolysis and filtration system is connected to an inlet of an activated carbon filtration system through a pipe; an outlet of the activated carbon filtration system is connected to an inlet of a crystallization system of hydrolysis liquid cooling through a pipe; an outlet of the hydrolysis liquid cooling crystallization system is connected to an inlet of a BHET and water separation circulation system through a pipe; an outlet of the BHET and water separation circulation system is connected to an outlet of a BHET packaging and drying system through a pipe;
  • the hydrolysis and filtration system comprises two parts, a hydrolysis upper part in a reaction kettle structure and a filter lower part in a net-type structure; activated carbon filtration system is adsorption tower structure; and the hydrolysis liquid cooling crystallization system has a crystal tower structure.
  • the system can purify the degraded BHET from PET material and effectively increase the cleanliness factor of the finished product,
  • An outlet of a degradation and filtration system is connected to an inlet of a degradation liquid cooling crystallization system through a pipe; an outlet of the degradation liquid cooling crystallization system is connected to an inlet of an ethylene glycol and BHET separation circulatory system through a pipe; an outlet of the ethylene glycol and BHET separation circulation system is connected to an inlet of a BHET quantitative feeding system through a pipe; an outlet of the BHET quantitative feed system is connected to an inlet of a hydrolysis system and filtration through a pipe; the outlet of the hydrolysis and filtration system is connected to an inlet of an activated carbon filtration system through a pipe; the outlet of the activated carbon filtration system is connected to an inlet of a hydrolysis liquid cooling crystallization system by a pipe; an outlet of the hydrolysis liquid cooling crystallization system is connected to an inlet of the BHET-water separation circulatory system through a pipe; and the outlet of the BHET-water separation circulatory system is connected to a BHET drying and packaging system through
  • the present invention is related to a heterogeneous catalyst, and a manufacturing process of said heterogeneous catalyst, which consists of an impregnation process of the active metal on activated carbon, which is supported inside the reactor by means of a mesh, at its Once, with this catalyst, a chemical process has been carried out to obtain the BHET monomer through the use of rPET and ethylene glycol, as raw materials, which consists of two main stages, a first stage, where the chemical reaction process is carried out , and a second stage, which consists of the purification stage where the BHET product is obtained at a purity of 99%.
  • Figure 1 corresponds to a flow diagram of a process according to one embodiment of the present invention.
  • Figure 2 corresponds to a table of related equipment in the flow diagram of a process according to one embodiment of the present invention.
  • Figure 3 Shows an image of the FTIR Spectrum of the BHET with a purity of 99% obtained after the second crystallization process.
  • Figure 4 Shows an image of the TGA/DSC Spectrum of the BHET with a purity of 99% obtained after the second crystallization process.
  • FIG. 5 Shows the Images and the concentration of elements on the surface of the heterogeneous catalyst by Scanning Electron Microscopy (SEM) and Energy Dispersive X-ray Spectroscopy (EDS).
  • SEM Scanning Electron Microscopy
  • EDS Energy Dispersive X-ray Spectroscopy
  • the present application relates to a process for obtaining a heterogeneous catalyst for the production of BHET monomer from recycled PET.
  • the heterogeneous catalyst comprises an activated carbon core that is impregnated with active metal.
  • the activated carbon core is produced using bituminous coal as raw material, which is subjected to a demineralization process to reduce the ash content, which consists of introducing 50 g of carbon in 100 ml of a 12 N HCl solution for 48 hours. After this time, it is ground and sieved until a particle size of 100 - 200
  • This carbon is chemically activated with KOH as an activating agent in a 4:1 ratio using the physical mixing method.
  • This mixture, activating agent - carbon is carbonized in an oven at a temperature of 750° C under a nitrogen atmosphere and at a heating rate of 5° C /min for a period of time of 2 hours. Then, the activated carbon is washed repeatedly with a 0.1 M HCL solution until a neutral pH is reached in the filtered water. Subsequently, it is washed with distilled water in a Soxlet equipment for 24 hours and then dried in an oven that is maintained at 1 10 °C for 24 hours.
  • the catalyst is placed inside a mesh container and introduced into a reactor where there is a mixture of rPET with ethylene glycol in a ratio of between 1 and 16 parts of PET to one of ethylene glycol, and a ratio of between 3.5 and 10 parts of PET for 1 part of catalyst.
  • the reaction is carried out at a temperature of 180°C for 120 minutes, after which the reaction medium is pumped to a filter that retains unreacted PET, PET dyes and other impurities.
  • the BHET monomer diluted in ethylene glycol present in the filtrate is sent to the crystallization stage.
  • the filtrate obtained from the filtration step is sent to a cooling tank, where the temperature is reduced to 4°C to promote the crystallization of the BHET. From the cooling tank the solution is pumped to a filter where the BHET is separated from the unreacted ethylene glycol, which is recirculated to the reactor.
  • the crystallized BHET is washed with water, and the mixture of washing water and ethylene glycol is purified to recover the ethylene glycol and recirculate it to the reactor.
  • the BHET is subjected to a drying process in a dryer at a temperature between 80°C and 120°C for a period of between 2 and 4 hours, after which a BHET with 99% purity is obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Sustainable Development (AREA)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)

Abstract

La présente invention concerne un catalyseur hétérogène et un procédé de fabrication dudit catalyseur hétérogène, qui consiste en un procédé d'imprégnation du métal actif sur du charbon actif, celui-ci étant supporté dans le réacteur au moyen d'une grille. Avec ce catalyseur, on a réalisé un procédé chimique d'obtention du monomère BHET par l'utilisation du rPET et d'éthylène glycol, comme matières premières, lequel procédé comprend deux étapes principales, une première étape dans laquelle est effectué le processus de réaction chimique et une seconde étape, qui consiste en une étape de purification dans laquelle le produit BHET avec une pureté de 99% est obtenu.
PCT/IB2023/055212 2022-05-23 2023-05-20 Catalyseur et procédé d'obtention de bhet à partir de pet WO2023228034A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CONC2022/0006786A CO2022006786A1 (es) 2022-05-23 2022-05-23 Catalizador y proceso para la obtención de bhet (bis 2 etilen tereftalato) a partir de pet (poli etilen tereftalato) residual
CONC2022/0006786 2022-05-23

Publications (1)

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WO2023228034A1 true WO2023228034A1 (fr) 2023-11-30

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018143798A1 (fr) * 2017-01-31 2018-08-09 Ioniqa Technologies B.V. Décomposition de polymères de condensation
CN109574835A (zh) * 2018-11-20 2019-04-05 江南大学 一种离子改性活性炭脱色聚酯醇解产物bhet的方法
WO2021032821A1 (fr) * 2019-08-21 2021-02-25 Ioniqa Technologies B.V. Procédé et système de réacteur pour la dépolymérisation d'un polymère de téréphtalate en une matière première réutilisable
US20220041836A1 (en) * 2018-09-12 2022-02-10 Petróleo Brasileiro S.A. - Petrobras Catalysts and method for producing recycled polyester

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018143798A1 (fr) * 2017-01-31 2018-08-09 Ioniqa Technologies B.V. Décomposition de polymères de condensation
US20220041836A1 (en) * 2018-09-12 2022-02-10 Petróleo Brasileiro S.A. - Petrobras Catalysts and method for producing recycled polyester
CN109574835A (zh) * 2018-11-20 2019-04-05 江南大学 一种离子改性活性炭脱色聚酯醇解产物bhet的方法
WO2021032821A1 (fr) * 2019-08-21 2021-02-25 Ioniqa Technologies B.V. Procédé et système de réacteur pour la dépolymérisation d'un polymère de téréphtalate en une matière première réutilisable

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Title
AO WENYA, FU JIE, MAO XIAO, KANG QINHAO, RAN CHUNMEI, LIU YANG, ZHANG HEDONG, GAO ZUOPENG, LI JING, LIU GUANGQING, DAI JIANJUN: "Microwave assisted preparation of activated carbon from biomass: A review", RENEWABLE AND SUSTAINABLE ENERGY REVIEWS, ELSEVIERS SCIENCE, NEW YORK, NY., US, vol. 92, 1 September 2018 (2018-09-01), US , pages 958 - 979, XP093115080, ISSN: 1364-0321, DOI: 10.1016/j.rser.2018.04.051 *
LALDINPUII ZATHANG, LALHMANGAIHZUALA SAMSON, PACHUAU ZODINPUIA, VANLALDINPUIA KHIANGTE: "Depolymerization of poly(ethylene terephthalate) waste with biomass-waste derived recyclable heterogeneous catalyst", WASTE MANAGEMENT., ELSEVIER, NEW YORK, NY., US, vol. 126, 1 May 2021 (2021-05-01), US , pages 1 - 10, XP093115081, ISSN: 0956-053X, DOI: 10.1016/j.wasman.2021.02.056 *
YANG MINHO, KIM DONG SEOK, SIM JAE-WOOK, JEONG JAE-MIN, KIM DO HYUN, CHOI JAE HYUNG, KIM JINSOO, KIM SEUNG-SOO, CHOI BONG GILL: "Synthesis of vertical MnO 2 wire arrays on hemp-derived carbon for efficient and robust green catalysts", APPLIED SURFACE SCIENCE, ELSEVIER, AMSTERDAM , NL, vol. 407, 1 June 2017 (2017-06-01), Amsterdam , NL , pages 540 - 545, XP093115079, ISSN: 0169-4332, DOI: 10.1016/j.apsusc.2017.02.219 *
YOSI KRATISH; JIAQI LI; SHANFU LIU; YANSHAN GAO; TOBIN J. MARKS: "Polyethylene Terephthalate Deconstruction Catalyzed by a Carbon‐Supported Single‐Site Molybdenum‐Dioxo Complex", ANGEWANDTE CHEMIE, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 132, no. 45, 15 September 2020 (2020-09-15), DE , pages 20029 - 20033, XP071384352, ISSN: 0044-8249, DOI: 10.1002/ange.202007423 *

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