WO2024254475A1 - Polyéthylène téréphtalate produit à partir de pneus usagés - Google Patents

Polyéthylène téréphtalate produit à partir de pneus usagés Download PDF

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Publication number
WO2024254475A1
WO2024254475A1 PCT/US2024/033045 US2024033045W WO2024254475A1 WO 2024254475 A1 WO2024254475 A1 WO 2024254475A1 US 2024033045 W US2024033045 W US 2024033045W WO 2024254475 A1 WO2024254475 A1 WO 2024254475A1
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Prior art keywords
tire
feedstock
ethanol
converting
ethylene
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English (en)
Inventor
Terrence E. Hogan
Mark W. Smale
William S. Niaura
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Bridgestone Americas Tire Operations LLC
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Bridgestone Americas Tire Operations LLC
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Publication of WO2024254475A1 publication Critical patent/WO2024254475A1/fr
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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
    • C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
    • C07C1/24—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by elimination of water
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
    • C07C29/103—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers
    • C07C29/106—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes of cyclic ethers of oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/15—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively
    • C07C29/151—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of oxides of carbon exclusively with hydrogen or hydrogen-containing gases
    • C07C29/1516—Multisteps
    • C07C29/1518—Multisteps one step being the formation of initial mixture of carbon oxides and hydrogen for synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • 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
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C08G63/183—Terephthalic acids
    • 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
    • C08G63/78—Preparation processes
    • 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
    • C08J11/12—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 dry-heat treatment only
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C9/00—Reinforcements or ply arrangement of pneumatic tyres
    • B60C9/0042—Reinforcements made of synthetic materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
    • C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
    • C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
    • C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
    • 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
    • C08J2317/00—Characterised by the use of reclaimed rubber

Definitions

  • Embodiments of the present invention are directed toward a process for converting used tires to polyethylene terephthalate.
  • the polyethylene terephthalate can be used in the manufacture of tire cord fabric that is useful in the manufacture of tire components.
  • BACKGROUND OF THE INVENTION Used tires include a significant amount of carbonaceous material. Recycling the carbon into other carbon-based materials presents numerous challenges due, at least in part, to the fact that a majority of the carbon is tied up in a vulcanized network.
  • One or more embodiments of the present invention provide a process comprising (a) providing a feedstock that includes carbonaceous materials; (b) gasifying the feedstock to produce a gaseous stream including carbon monoxide, hydrogen, and carbon dioxide; (c) converting at least a portion of the carbon monoxide, hydrogen, and carbon dioxide to ethanol; (d) converting at least a portion of the ethanol to ethylene; (e) converting at least a portion of the ethylene to ethylene oxide; (f) converting at least a portion of the ethylene oxide to ethylene glycol; (g) combining at least a portion of the ethylene glycol with terephthalic acid; and (h) polymerizing the ethylene glycol and
  • a tire component comprising: a composite including a tire cord fabric and cured rubber, where the tire cord fabric includes cords including polyester fibers obtained from polyester synthesized using constituents from the gasification of a feedstock including carbonaceous materials.
  • the tire includes greater than 40 wt %, or 50 wt %, or 60 wt %, or 70 wt %, or 80 wt %, or 90 wt %, or 99 wt % sustainable material.
  • Embodiments of the invention are based, at least in part, on the discovery of a process for consuming used tires in the production of polyethylene terephthalate.
  • the polyethylene terephthalate can advantageously be used to produce tire cord fabric that can be used to manufacture tire components.
  • Embodiments of the invention therefore provide a methodology for converting used tires back to useful tires or tire components.
  • used tires are thermally decomposed to form a gaseous stream. One or more components of this gaseous stream are then converted to polyethylene terephthalate. One or more components of the gaseous stream are converted to ethanol, and the ethanol is then converted to ethylene.
  • the process of the present invention provides a feedstock, which may include tire feedstock, and the feedstock is converted, via thermal decomposition, to a gaseous stream that includes hydrogen, carbon monoxide, and optionally carbon dioxide.
  • This gaseous stream which may be referred to as synthesis gas or syngas, is then converted to ethanol by using biological fermentation processes.
  • the ethanol is then converted to ethylene, which can be done catalytically by a one-step process.
  • the feedstock that is thermally decomposed to form the gaseous stream may include tire feedstock from used tires, which may also be referred to as used tire feedstock or simply tire feedstock.
  • tire feedstock may include vulcanized polymer, carbon black filler, silica, resins, oils, fibrous yarn, and metal.
  • the vulcanized polymer may include the sulfur-crosslinked residue of natural rubber and/or one or more synthetic elastomers including diene polymers and copolymers.
  • the used tire feedstock may include shredded or otherwise ground tires with one or more constituents of the used tire removed.
  • the tire feedstock may be treated to remove metal by methods known in the art (e.g. magnetic separation).
  • the used tire feedstock may be optionally treated to remove fibrous reinforcement such as fiber yarn or cord, which the skilled person understands is often found in conjunction with the vulcanized rubber within many tire components.
  • the used tire feedstock may be optionally treated to remove inorganic materials such as silica filler, which the skilled person appreciates is often found in used tire components.
  • the tire feedstock can be processed into tire shreds, tire chips, or ground or crumb rubber and fed to the thermal decomposition unit.
  • the tire feedstock is characterized by relatively low amounts of metal, which low amounts may result from pre-treatment of the tire feedstock to remove at least a portion of the metal that is typically present in used tires.
  • the tire feedstock may include less than 25 wt %, in other embodiments less than 15 wt %, and in other embodiments less than 1 wt % metal based on the entire weight of the feedstock fed to thermal decomposition in accordance with the present invention.
  • the tire feedstock is characterized by relatively low amounts of fibrous yarn or cord, which low amounts may result from pre-treatment of the tire feedstock to remove at least a portion of the fibrous yarn or cord that is typically present in used tires.
  • the tire feedstock following pre-treatment, includes less than 5 wt %, in other embodiments less than 4 wt %, in other embodiments less than 3 wt %, in other embodiments less than 2 wt %, and in other embodiments less than 1 wt % fibrous yarn or cord based on the entire weight of the feedstock fed to thermal decomposition in accordance with the present invention.
  • the tire feedstock is characterized by relatively low amounts of inorganic filler (e.g. silica), which low amounts may result from pre- treatment of the tire feedstock to remove at least a portion of the inorganic filler that is typically present in used tires.
  • the tire feedstock following pre-treatment, includes less than 30 wt %, in other embodiments less than 20 wt %, in other embodiments less than 10 wt %, and in other embodiments less than 5 wt % inorganic filler based on the entire weight of the feedstock fed to thermal decomposition in accordance with the present invention.
  • the used tire feedstock includes tire remains from passenger tires.
  • the used tire feedstock includes tire remains from non-passenger tires such as, but not limited to, truck and bus tires, off-road vehicle tires, agricultural tires, and race tires.
  • the used tires are mechanically treated (e.g. ground or shredded) to form a ground or shredded material (i.e. the feedstock is ground or shredded).
  • This ground or shredded material i.e. the tire feedstock, which may also be referred to as crumb, may be characterized by an advantageous compacted density.
  • the feedstock may have a compacted density of greater than 640 kg/m3, in other embodiments greater than 720 kg/m3, and in other embodiments greater than 770 kg/m3, where density is determined by ASTM D 698-07.
  • the feedstock provided to the thermal decomposition unit includes used tires and optionally complementary feedstock.
  • the complementary feedstock which may also be referred to as co-feed, includes carbonaceous materials other than the tire feed stock. Carbonaceous material refers to any carbon material whether in solid, liquid, gas, or plasma state.
  • Non-limiting examples of carbonaceous materials include carbonaceous liquid product, industrial liquid recycle, municipal solid waste (MSW or msw) including municipal solid waste with higher biomass content and/or with decreased recyclable material content, urban waste, agricultural material, forestry material, wood waste, construction material, vegetative material, industrial waste, fermentation waste, petrochemical coproducts, alcohol production coproducts, coal, plastics, waste plastic, coke oven tar, lignin, black liquor, polymers, waste polymers, polyethylene terephthalate (PETA), polystyrene (PS), sewage sludge, animal waste, crop residues, energy crops, forest processing residues, wood processing residues, livestock wastes, poultry wastes, food processing residues, ethanol coproducts, spent grain, spent microorganisms, municipal waste, construction waste, demolition waste, biomedical waste, hazardous waste, or their combinations.
  • MSW or msw municipal solid waste with higher biomass content and/or with decreased recyclable material content
  • urban waste agricultural material, forestry material, wood waste, construction
  • the carbonaceous material includes biomass.
  • the biomass is bagasse including, but not limited to, the bagasse of sugar cane, sorghum, and guayule plant.
  • the feedstock includes a blend of used tires and municipal solid waste, wherein the municipal solid waste can include biomass.
  • the feedstock includes used tires and municipal solid waste that is substantially exclusive of biomass (i.e. substantially petroleum-based solid municipal waste).
  • the feedstock includes used tires and biomass.
  • the feedstock includes used tires and municipal solid waste that has had most of the recyclable plastics removed (i.e. substantially exclusive of recyclable plastics).
  • the guayule bagasse is produced as the result of a process to extract rubber and resin from the guayule plant, such as described in U.S. Publication No. 2022/0356273, which is incorporated herein by reference. Methods for the desolventization of guayule bagasse are described in U.S. Patent No. 10,132,563, which is also incorporated herein by reference.
  • the guayule bagasse contains no more than 1 wt % organic solvent (based upon the total weight of the dried bagasse).
  • the dried bagasse contains no more than 0.5 wt % organic solvent (based upon the total weight of the dried bagasse).
  • the dried bagasse may contain a quantity of water and higher boiling point terpenes.
  • the total quantity of water and higher boiling point terpenes in the dried bagasse may be higher than the content of organic solvents.
  • the co-feed e.g. biomass or municipal waste
  • the feedstock may be characterized by the amount of co-feed (e.g. biomass or municipal waste).
  • the feedstock includes from about 0 to about 95, in other embodiments from about 1 to about 75, and in other embodiments from about 2 to about 55 wt % co-feed with the balance including used tire.
  • the feedstock includes less than 95, in other embodiments less than 80, and in other embodiments less than 70 wt % co-feed.
  • the feedstock includes greater than 10, in other embodiments greater than 20, in other embodiments greater than 30, in other embodiments greater than 40, in other embodiments greater than 50, and in other embodiments greater than 70 wt % used tires, with the balance including complementary feedstock.
  • the feedstock is substantially, and in certain embodiments exclusively, comprised of those carbonaceous materials identified above other than tire feedstock; i.e. the feedstock is substantially or exclusively comprised of the co-feed materials identified above.
  • the feedstock includes greater than 80 wt %, in other embodiments greater than 90 wt %, and in other embodiments greater than 99 wt % municipal solid waste.
  • the feedstock includes greater than 80 wt %, in other embodiments greater than 90 wt %, and in other embodiments greater than 99 wt % biomass.
  • the feedstock (which may include tire feedstock and optionally co-feed) is thermally decomposed into gaseous streams including hydrogen, carbon monoxide, and optionally carbon dioxide by employing techniques that are generally known in the art.
  • these processes may include gasification processes, and it is also known that these processes can be tailored to control the chemical nature of the resulting gaseous stream.
  • the degree of combustion can be controlled by controlling the amount of oxygen present during thermal decomposition.
  • the step of thermal decomposition takes place in a substantially inert environment.
  • Processes that may be used for the thermal decomposition step may include pyrolysis or gasification reactions as disclosed in U.S. Publication Nos. 2021/0207037; 2019/0295734; 2019/0249089; 2018/0273415; 2017/0009162; 2017/0002271; 2016/0107913; 2016/0068773; 2016/0024404; 2014/0182205; 2014/0157667; and 2014/0100294, which are incorporated herein by reference.
  • the feedstock includes both tire feedstock and co-feed
  • the tire feedstock and the co-feed can be introduced to the same thermal decomposition unit simultaneously.
  • the tire feedstock and the co-feed can be pre-mixed at a desired ratio to form the feedstock that is fed to the thermal decomposition unit.
  • separate streams of tire feedstock and co-feed can be separately and individually fed to the thermal decomposition unit at a desired rate.
  • the two feedstocks i.e. the tire feedstock and the co-feed
  • the two feedstocks can be treated within separate thermal decomposition units operating in parallel, and then the gaseous streams produced by the respective units can be combined to attain the desired ratio of gaseous constituents.
  • the gaseous product stream produced by thermal decomposition of the feedstock includes carbon monoxide, hydrogen and optionally carbon dioxide.
  • the gaseous product stream includes from about 5 to about 50, or in other embodiments from about 7 to about 25, or in other embodiments from about 8 to about 15 volume percent carbon dioxide.
  • the gaseous product stream includes from about 10 to about 85, or in other embodiments from about 20 to about 65, or in other embodiments from about 25 to about 45 volume percent hydrogen.
  • the gaseous product stream includes from about 20 to about 85, or in other embodiments from about 30 to about 75, or in other embodiments from about 40 to about 60 volume percent carbon monoxide.
  • the gaseous product stream produced by thermal decomposition includes from about 40 to about 80 wt %, in other embodiments from about 45 to about 75 wt %, and in other embodiments from about 50 to about 70 wt % carbon (i.e. carbon within carbon-based compounds) based on the total weight of the gaseous product stream.
  • CONDITIONING OF GASEOUS STREAM [0023]
  • the gaseous stream is conditioned (i.e.
  • the gaseous product stream from thermal decomposition may be pressurized.
  • pressurization of the gaseous stream achieves sufficient pressure to overcome counter forces within the bioreactor. As the skilled person understands, this will permit flow of the gas through the bioreactor and allow inert gases (e.g. nitrogen) within the gaseous stream to enter the head space of the reactor.
  • the gaseous stream is pressurized to a pressure of from about 5 to about 20 barr.
  • the gaseous stream can be cooled.
  • the gaseous stream can be cooled, for example, within a heat exchanger such as a water- cooled unit.
  • the gaseous stream is cooled to a temperature below that which would otherwise have a deleterious impact on the microorganism culture within the bioreactor.
  • the gaseous stream is cooled to a temperature of from about 25 to about 45 °C prior to delivery to the bioreactor.
  • the gaseous stream can be treated to remove undesirable constituents that may be entrained within the stream.
  • the gaseous stream can be treated within a scrubber prior to being introduced to the bioreactor.
  • this may include the use of a catalyst (e.g. iron oxide) to remove sulfur compounds such as hydrogen sulfide.
  • the stream may also be treated to remove acids (e.g. treatment with calcium or sodium carbonate with particular interest in removing hydrogen cyanides).
  • a catalyst e.g. iron oxide
  • acids e.g. treatment with calcium or sodium carbonate with particular interest in removing hydrogen cyanides.
  • Exemplary systems for removing hydrogen sulfide from gaseous streams include those available from EcoVapor (Denver, Colorado). Other methods include the use of caustic such as those systems available from DMT under the tradename Sulfurex BF (Netherlands).
  • SYNGAS TO ETHANOL [0026] As indicated above, constituents of the gaseous stream are converted to ethanol that is contained within an ethanol-containing stream; i.e. a product stream that includes ethanol.
  • the gaseous stream is supplemented with hydrogen prior to converting the gaseous stream to an ethanol-containing stream.
  • the gaseous stream is converted to ethanol via biosynthetic techniques.
  • syngas can be converted to ethanol by fermentation utilizing microorganisms, such as bacteria.
  • the microorganisms may be acetogenic autotrophic microbes.
  • Acetogenic microbes i.e. bacteria
  • the acetyl-CoA is then converted to organic products, such as acetic acid and ethanol.
  • acetogens can reduce the acetic acid (e.g. an organic acid) into an alcohol (e.g. ethanol).
  • This acetogenic mechanism, as well as the microorganism chosen may be considered relative to preferentially producing ethanol.
  • Microorganisms other than acetogens may be suitable with different pathways to reaching ethanol.
  • One or more useful microorganisms may simultaneous uptake both CO and H2 in the syngas. In these or other embodiments, certain microorganisms can reduce CO2 to CO in the presence of excess hydrogen.
  • microorganisms and techniques for their use are disclosed in “A Techno-Economic Assessment of Bioethanol Production from Switchgrass Through Biomass Gasification and Syngas Fermentation” Regis et al, Energy 274, 127318, (2023).
  • various conditions of microorganism- driven biosynthesis may be adjusted relative to preferential production of ethanol.
  • the pH, temperature, and concentrations of nutrients within the bioreactor where in the biosynthesis takes place can be adjusted.
  • the desirable pH, temperature, and concentrations of nutrients may depend on the particular microorganisms employed.
  • the syngas is converted to ethanol via thermochemical techniques.
  • thermochemical techniques exist to convert syngas to ethanol.
  • a crude ethanol-containing stream which is obtained directly from the bioreactor in which the ethanol is synthesized, is delivered to downstream steps.
  • the ethanol-containing stream is purified to produce an ethanol-containing stream that is higher in ethanol content.
  • the ethanol-containing stream exiting the step wherein syngas is converted to ethanol (i.e. the bioreactor) and delivered to the downstream steps where ethanol is further converted (optionally after purification) includes greater than 80 wt %, in other embodiments greater than 90 wt %, and in other embodiments greater than 95 wt % ethanol based upon the entire weight of the ethanol-containing stream.
  • ethanol within the ethanol-containing stream is converted to ethylene, which is then contained within an ethylene-containing stream.
  • ethanol is converted to ethylene using catalytic techniques, which are well known in the art.
  • useful catalysts include acid catalysts, alumina and transition metal oxides, silicoaluminophosphates (SAPO), HZSM-5 zeolite catalyst, and heteropolyacid catalysts. Modifications of these catalysts, such as nanoscale versions, may also be employed.
  • SAPO silicoaluminophosphates
  • HZSM-5 zeolite catalyst silicoaluminophosphates
  • heteropolyacid catalysts Modifications of these catalysts, such as nanoscale versions, may also be employed.
  • some catalytic techniques proceed by dehydrating ethanol to form ethylene.
  • acid catalyst first protonates the hydroxyl group of the ethanol forming a molecule of water as a leaving group.
  • the conjugate base of the remaining catalyst then deprotonates the methyl group, and the hydrocarbon rearranges to ethylene.
  • ethanol is converted to ethylene via catalytic dehydration over an aluminum oxide catalyst.
  • conversion of ethanol to ethylene takes place at a temperature of from about 180 °C to about 500 °C.
  • processes for the conversion of ethanol to ethylene are well known and commercially available. For example, commercial processes are marketed by Braskem S.A., Technip Energys, Axens S.A. and Scientific Design Company, Inc.
  • ETHYLENE TO ETHYLENE OXIDE ethylene within the ethylene -containing stream is converted to ethylene oxide.
  • Processes for converting ethylene to ethylene oxide are known.
  • ethylene is commonly oxidized to ethylene oxide in the presence of oxygen and an appropriate catalyst.
  • Exemplary processes are disclosed in U.S. Patent No. 1,998,878, which is incorporated herein by reference.
  • Useful catalysts may include silver, bismuth and/or antimony, which may be used in combination with other materials such as gold, coper and iron.
  • additives can be present during the reaction.
  • Useful additives include water, carbon dioxide, hydrogen, and ethyl chloride.
  • the oxidation reaction can be conducted at elevated temperatures and pressures to facilitate conversion.
  • oxidation can take place at temperature of from about 150 to about 400 °C and at pressures up to 50 atmospheres.
  • the product stream obtained from the step of converting ethylene to ethylene oxide is a crude stream obtained directly from the reactor used to produce the ethylene oxide.
  • the ethylene oxide-containing stream is purified to produce an ethylene oxide-containing stream that is higher in ethylene oxide content; for example, the ethylene oxide stream can be subjected to distillation as described above.
  • the ethylene oxide-containing product stream obtained from this step e.g.
  • ethylene oxide within the ethylene oxide-containing stream is converted to ethylene glycol.
  • Processes for converting ethylene oxide to ethylene glycol are known and generally include reacting ethylene oxide with water in the presence of acids and bases, which catalyze the reaction. These reactions are typically conducted in the presence of excess water.
  • One exemplary catalyst is a quaternary phosphonium salt, which is used in conjunction with carbon dioxide as disclosed in U.S. Patent No.
  • the reaction medium is charged with about 0.05 to about 1 mole per mole of carbon dioxide per mole of ethylene oxide.
  • the product stream obtained from the step of converting ethylene oxide to ethylene glycol is a crude stream obtained directly from the reactor used to produce the ethylene glycol.
  • the ethylene glycol- containing stream is purified to produce an ethylene glycol-containing stream that is higher in ethylene glycol content; for example, the ethylene glycol-containing stream can be subjected to distillation as described above.
  • the ethylene glycol-containing product stream obtained from this step e.g.
  • ethylene is converted to ethylene glycol using the two-step process whereby ethylene is oxidized using a silver catalyst in the presence of ethyl chloride to produce ethylene oxide, which is then reacted with carbon dioxide to produce ethylene carbonate.
  • exemplary processes to produce ethylene carbonate are disclosed in U.S. Patent No. 4,314,945, which is incorporated herein by reference.
  • ethylene carbonate is then converted to ethylene glycol by hydrolysis.
  • exemplary processes for the hydrolyzing ethylene carbonate are disclosed in U.S. Patent No. 4,117,250, which is incorporated herein by reference.
  • Ethylene glycol via ethylene carbonate formation is also conducted by the so called “OMEGA Process,” which is commercially operated by Shell Global Solutions.
  • ETHYLENE GLYCOL AND TEREPHTHALIC ACID TO POLYETHYLENE TEREPHTHALATE [0039] As indicated above, ethylene glycol within the ethylene glycol-containing stream and terephthalic acid are reacted within a condensation polymerization to form polyethylene terephthalate.
  • Condensation polymerization reactions for producing polyethylene terephthalate from ethylene glycol and terephthalic acid are well known.
  • known processes may employ acid catalysts to promote the condensation reaction.
  • the reaction can be conducted under vacuum, which removes water from the polymerization and thereby drives the reaction to completion.
  • These condensation reactions typically take place at temperatures of from about 50 to about 200 °C.
  • the product stream i.e. the polyethylene terephthalate
  • the product stream obtained from the step of polymerizing ethylene glycol and terephthalic acid is a crude stream obtained directly from the reactor used to produce the polyethylene terephthalate.
  • the polyethylene terephthalate-containing stream is purified to produce a polyethylene terephthalate-containing stream that is higher in polyethylene terephthalate content; for example, the polyethylene terephthalate-containing stream can be subjected to distillation as described above.
  • the polyethylene terephthalate-containing product stream obtained from this step includes greater than 80 wt %, in other embodiments greater than 90 wt %, and in other embodiments greater than 95 wt % polyethylene terephthalate based upon the entire weight of the polyethylene terephthalate-containing stream.
  • the polyester terephthalate (PET) produced by practice of the present invention is formed into yarns, which may then be twisted into cords. For example, two yarns may be twisted into a cord.
  • the cords can be fabricated (e.g. weaved) into fabrics, which may be referred to as tire cord fabric.
  • the nature of the yarn, cords, and the resulting fabric are adapted for use as tire cord fabric for use in tire components.
  • the tire cord fabric is surface treated, for example, by using known dipping techniques, prior to being incorporated into a tire.
  • the tire cord fabric can be calendared, which usually involves sandwiching the fabric between layers of rubber, to form a reinforced ply that is incorporated into a pneumatic tire.
  • techniques are well known for spinning polymers into fibers. Generally, this includes forcing the polymer material through a spinneret or die under appropriate conditions. The fibers can then be fabricated into yarns, twisted into cords, and woven into woven into fabric by using known techniques.
  • the present invention provides a method by which waste material, in particular waste material from used tires, is converted back to useful tires. In other words, a tire recycling or tire circularity method is provided by the present invention.
  • the PET tire cord fabric synthesized and used in the practice of this invention may be referred to as circular PET tire cord fabric.
  • Practice of the present invention not only offers a method for recycling tires by employing used tires as a feedstock to produce PET that can be incorporated back into tires as PET tire cord fabric, but the practice of the present invention also advantageously provides a method whereby a tire is produced that has a relatively high content of sustainable constituents, which include recycled materials, naturally-derived materials and/or materials synthesized from bio-synthesized feedstock or bio-based materials.
  • these tires or tire components include threshold amounts of circular PET tire cord while being characterized by high sustainable content.
  • the tires or tire components of the present invention can include greater than 40 wt %, in other embodiments greater than 50 wt %, and in other embodiments greater than 60 wt % sustainable materials.
  • the tire or tire components include from about 40 to about 90 wt %, in other embodiments from about 45 to about 85 wt %, and in other embodiments from about 50 to about 80 wt % sustainable material.
  • the tire cord incorporated into the tires or tire components of the present invention include greater than 10 wt %, in other embodiments greater than 20 wt %, in other embodiments greater than 30 wt %, in other embodiments greater than 40 wt %, in other embodiments greater than 45 wt %, and in other embodiments greater than 50 wt % circular PET tire cord fabric, which includes PET produced according to embodiments of the present invention.
  • the tire various rubber or rubber-containing components of a tire are produced by preparing and vulcanizing rubber compositions, which are often referred to as vulcanizable rubber compositions or simply rubber compositions.
  • the vulcanizable rubber compositions include a rubber component, filler, wax, and curative. Other ingredients that may be included in the vulcanizable rubber composition include extender oils, processing oils, and resins.
  • ELASTOMER [0045]
  • the rubber component of the vulcanizable rubber compositions includes a vulcanizable elastomer, which may also be referred to as an elastomer, a vulcanizable rubber, or simply as a rubber.
  • the vulcanizable elastomer is capable of being cured, which may also be referred to as vulcanized, to form an elastomeric composition.
  • the rubber component includes one or more synthetic polymers.
  • These synthetic polymers may include, for example and without limitation, synthetic polyisoprene, polybutadiene, polyisobutylene-co-isoprene, neoprene, poly(ethylene-co-propylene), poly(styrene-co-butadiene), poly(styrene-co- isoprene), poly(styrene-co-isoprene-co-butadiene), poly(isoprene-co-butadiene), poly(ethylene-co-propylene-co-diene), polysulfide rubber, acrylic rubber, urethane rubber, silicone rubber, epichlorohydrin rubber, and mixtures thereof.
  • the rubber component of the vulcanizable rubber compositions of this invention includes one or more circular synthetic rubbers, which is vulcanizable rubber produced from used tires. These circular synthetic rubbers may be used alone as the rubber component or in combination with synthetic polymers.
  • the rubber component may include one or more natural rubbers. Natural rubber may be used alone as the rubber component or in combination with synthetic polymers and/or circular synthetic rubber. As the skilled person understands, natural rubber is synthesized by and obtained from plant life.
  • natural rubber can be obtained from Hevea rubber trees, guayule shrub, gopher plant, mariola, rabbitbrush, milkweeds, goldenrods, pale Indian plantain, rubber vine, Russian dandelions, mountain mint, American germander, and tall bellflower.
  • the rubber compositions of this invention include from about 30 to about 65 wt %, in other embodiments from about 35 to about 60 wt %, and in other embodiments from about 40 to about 55 wt % elastomer, based on the total weight of the tire component.
  • the rubber compositions include fillers such as organic and inorganic fillers. Examples of organic fillers include carbon black and starch.
  • inorganic fillers examples include silica, aluminum hydroxide, magnesium hydroxide, mica, talc (hydrated magnesium silicate), and clays (hydrated aluminum silicates). In certain embodiments, a mixture of different fillers may be advantageously employed.
  • the amount of total filler employed in the rubber compositions can be up to about 150 parts by weight per 100 parts by weight of rubber (phr), with about 30 to about 125 phr, or about 40 to about 110 phr being typical. In certain embodiments the total filler content is greater than about 100 phr. In other embodiments, the total filler content is from about 50 to about 100 phr, and in in further embodiments from about 55 to about 95 phr.
  • carbon blacks include furnace blacks, channel blacks, and lamp blacks. More specific examples of carbon blacks include super abrasion furnace blacks, intermediate super abrasion furnace blacks, high abrasion furnace blacks, fast extrusion furnace blacks, fine furnace blacks, semi-reinforcing furnace blacks, medium processing channel blacks, hard processing channel blacks, conducting channel blacks, and acetylene blacks.
  • the carbon blacks may have a surface area (EMSA) of at least 20 m2/g and in other embodiments at least 35 m2/g; surface area values can be determined by ASTM D-1765 using the cetyltrimethylammonium bromide (CTAB) technique.
  • the carbon blacks may be in a pelletized form or an unpelletized flocculent form. The preferred form of carbon black may depend upon the type of mixing equipment used to mix the rubber compound.
  • carbon black can be sourced from a recycled material.
  • Such recycled material can include reclaimed or recycled vulcanized rubber, whereby the vulcanized rubber is typically reclaimed from manufactured articles such as a pneumatic tire, an industrial conveyor belt, a power transmission belt, and a rubber hose.
  • the recycled carbon black may be obtained by a pyrolysis process or other methods known for obtaining recycled carbon black.
  • a recycled carbon black can be formed from incomplete combustion of recycled rubber feedstock or rubber articles.
  • the recycled carbon black can be formed from the incomplete combustion of feedstock including oil resulting from the tire pyrolysis process.
  • the carbon blacks utilized in the preparation of the vulcanizable elastomeric compositions can be in pelletized form or an unpelletized flocculent mass.
  • the amount of carbon black employed in the rubber compositions can be up to about 75 parts by weight per 100 parts by weight of rubber (phr), with about 5 to about 60 phr, or about 10 to about 55 phr being typical.
  • the rubber composition can further include filler in the form of one or more recycled rubbers in a particulate form. Recycled particulate rubber is typically broken down and reclaimed (or recycled) by any of a plurality of processes, which can include physical breakdown, grinding, chemical breakdown, devulcanization, cryogenic grinding, a combination thereof, etc.
  • recycled particulate rubber can relate to both vulcanized and devulcanized rubber, where devulcanized recycle or recycled rubber (reclaim rubber) relates to rubber which has been vulcanized, ground into particulates and may have further undergone substantial or partial devulcanization.
  • the recycled particulate rubber used in the rubber composition is essentially free of recycled rubber resulting from devulcanization.
  • the vulcanized rubber contains wire or textile fiber reinforcement, such wire or fiber reinforcement can be removed by any suitable process such as magnetic separation, air aspiration and/or air flotation step.
  • the “recycled particulate rubber” comprises cured, i.e., vulcanized (crosslinked) rubber that has been ground or pulverized into particulate matter having a mean average particle size as discussed below.
  • Certain silicas may be considered sustainable materials. Some commercially available silicas which may be used as sustainable materials for the current invention include Hi-SilTM 215, Hi-SilTM 233, and Hi-SilTM 190 (PPG Industries, Inc.; Pittsburgh, Pa.). Other suppliers of commercially available silica include Grace Davison (Baltimore, Md.), Degussa Corp. (Parsippany, N.J.), Rhodia Silica Systems (Cranbury, N.J.), and J.M.
  • silicas may be characterized by their surface areas, which give a measure of their reinforcing character.
  • the Brunauer, Emmet and Teller (“BET”) method (described in J. Am. Chem. Soc., 1939, vol. 60, 2 p. 309-319) is a recognized method for determining the surface area.
  • the BET surface area of silica is generally less than 450 m2/g.
  • Useful ranges of surface area include from about 32 to about 400 m2/g, about 100 to about 250 m2/g, and about 130 to about 240 m2/g, and about 170 to about 220 m2/g.
  • the silica may have a BET surface area of 190 to about 280 m2/g.
  • the pH’s of the silicas are generally from about 5 to about 7 or slightly over 7, or in other embodiments from about 5.5 to about 6.8.
  • a coupling agent and/or a shielding agent may be added to the rubber compositions during mixing in order to enhance the interaction of silica with the elastomers.
  • the useful upper range is limited by the high viscosity imparted by silicas.
  • the silica employed in the rubber composition is derived from rice husk ash only, and in other embodiments the rubber compositions do not include silica from non-rice husk ash derived processes.
  • the amount of the silica or carbon black individually can be as low as about 1 phr.
  • the amounts of coupling agents and shielding agents range from about 4 wt % to about 20 wt % based on the weight of silica used.
  • the weight ratio or silica to total filler may be from about 5 wt % to about 99 wt % of the total filler, in other embodiments from about 10 wt % to about 90 wt % of the total filler, or in yet other embodiments from about 50 wt % to about 85 wt % of the total filler.
  • the silica and carbon black fillers employed in the rubber composition are selected from the group consisting of sustainable pyrolysis carbon black and/or rice husk ash derived silica.
  • a multitude of rubber curing agents may be employed, including sulfur or peroxide-based curing systems. Curing agents are described in Kirk-Othmer, ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY, Vol. 20, pgs. 365-468, (3rd Ed. 1982), particularly Vulcanization Agents and Auxiliary Materials, pgs. 390-402, and A.Y. Coran, Vulcanization, ENCYCLOPEDIA OF POLYMER SCIENCE AND ENGINEERING, (2nd Ed. 1989), which are incorporated herein by reference. Vulcanizing agents may be used alone or in combination.
  • the rubber composition may include one or more natural waxes.
  • a natural wax or one with no petroleum as its raw material, can include carnauba wax, candelilla wax (e.g., extracted from candelilla flowers), rice wax (e.g., separated from rice bran oil) and Japan wax (e.g., extracted from Japanese wax tree).
  • the rubber compositions of this invention include from about 1 to about 20 parts by weight, or in other embodiments from about 2 to about 15 parts by weight total wax per 100 parts by weight rubber.
  • the rubber compositions of this invention include threshold amounts of sustainable waxes, which includes natural waxes.
  • the amount of sustainable wax, relative to the total weight of wax included, may be from about 1 wt % to about 99 wt %, or in other embodiment from about 20 wt % to about 80 wt % of the total wax.
  • the rubber composition includes sustainable waxes only.
  • OILS OILS
  • oils sustainable oils, which include plant-based oils and bio- based oils, may be used. Plant-based oils may include plant-based triglycerides.
  • oils include, without limitation, palm oil, soybean oil (also referred to herein as soy oil), rapeseed oil, sunflower seed, peanut oil, cottonseed oil, oil produced from palm kernel, coconut oil, olive oil, corn oil, grape seed oil, hemp oil, linseed oil, rice oil, safflower oil, sesame oil, mustard oil, flax oil.
  • Other examples include nut-derived oils such oils obtained from beech nuts, cashews, mongongo nuts, macadamia nuts, pine nuts, hazelnuts, chestnuts, acorns, almonds, pecans, pistachios, walnuts, or brazil nuts.
  • oils can be produced by any suitable process such as mechanical extraction (e.g., using an oil mill), chemical extraction (e.g., using a solvent, such as hexane or carbon dioxide), pressure extraction, distillation, leaching, maceration, purification, refining, hydrogenation, sparging, etc.
  • mechanical extraction e.g., using an oil mill
  • chemical extraction e.g., using a solvent, such as hexane or carbon dioxide
  • pressure extraction e.g., using a solvent, such as hexane or carbon dioxide
  • distillation e.g., using a solvent, such as hexane or carbon dioxide
  • pressure extraction e.g., using a solvent, such as hexane or carbon dioxide
  • distillation e.g., using a solvent, such as hexane or carbon dioxide
  • pressure extraction e.g., using a solvent, such as hexane or carbon dioxide
  • distillation e.g., using a solvent,
  • bio-oils produced by recombinant cells can be produced using a select strain of algal cells that are fed with a supply of sugars (e.g., sucrose) and then allowed to ferment and produce a bio-oil with a selected profile; after sufficient growth or fermentation has taken place, the bio-oil is isolated from the cells and collected.
  • the rubber compositions of this invention can include from about 1 to about 70 parts by weight, or in other embodiments from about 5 to about 50 parts weight total oil per 100 parts by weight rubber.
  • the amount of sustainable oil, relative to the total weight of oil included, may be from about 1 wt % to about 99 wt %, or in other embodiment from about 20 wt % to about 80 wt %.
  • OTHER INGREDIENTS Other ingredients that are typically employed in rubber compounding may also be added to the rubber compositions. These include accelerators, accelerator activators, oils, plasticizer, waxes, scorch inhibiting agents, processing aids, zinc oxide, tackifying resins, reinforcing resins, fatty acids such as stearic acid, peptizers, and antidegradants such as antioxidants and antiozonants.
  • RUBBER COMPOSITION PROCESSING All ingredients of the rubber compositions can be mixed with standard mixing equipment such as Banbury or Brabender mixers, extruders, kneaders, and two-rolled mills. In one or more embodiments, the ingredients are mixed in two or more stages.
  • a so-called masterbatch which typically includes the rubber component and filler, is prepared.
  • the masterbatch may exclude vulcanizing agents.
  • the masterbatch may be mixed at a starting temperature of from about 25 °C to about 125 °C with a discharge temperature of about 135 °C to about 180 °C.
  • the vulcanizing agents may be introduced and mixed into the masterbatch in a final mixing stage, which is typically conducted at relatively low temperatures so as to reduce the chances of premature vulcanization.
  • additional mixing stages can be employed between the masterbatch mixing stage and the final mixing stage.
  • One or more remill stages are often employed where the rubber composition includes silica as the filler.
  • Various ingredients including the polymers of this invention can be added during these remills.
  • the mixing procedures and conditions particularly applicable to silica-filled tire formulations are described in U.S. Patent Nos. 5,227,425; 5,719,207; and 5,717,022, as well as European Patent No. 890,606, all of which are incorporated herein by reference.
  • the initial masterbatch is prepared by including the polymer and silica in the substantial absence of coupling agents and shielding agents.
  • TIRE FABRICATION In order to fabricate tire components with the polymers produced by the invention, the skilled person appreciates that the polymers are mixed with various other ingredients (e.g. filler and curative) to produce a rubber composition (also referred to as vulcanizable composition), and the vulcanizable composition is then processed into tire components according to ordinary tire manufacturing techniques, which generally include standard rubber shaping and molding techniques.
  • the tire components may include, but are not limited to, tire treads, sidewalls, subtreads, body ply skims, and bead filler.
  • the various tire components are then assembled into a green tire (i.e. an uncured tired), placed within a mold, and then vulcanized.
  • vulcanization is effected by heating the vulcanizable composition in a mold; e.g., it may be heated to about 140 °C to about 180 °C.
  • Cured or crosslinked rubber compositions may be referred to as vulcanizates, which generally contain three-dimensional polymeric networks that are thermoset.
  • the other ingredients, such as fillers and processing aids, may be evenly dispersed throughout the crosslinked network.
  • Pneumatic tires can be made as discussed in U.S. Patent Nos. 5,866,171; 5,876,527; 5,931,211; and 5,971,046, which are incorporated herein by reference.
  • tires produced according to the present invention include fabric reinforcement made by using PET tire cord produced by the practice of this invention
  • the PET tire cords only include PET yarns produced from PET synthesized according the present invention.
  • the PET cords include PET yarns from the present invention in combination with one or more other fibers.
  • These other yarns can include sustainable fibers such as, but not limited to, mechanically recycled fibers, chemically recycled fibers, or bio-based fibers.
  • the other yarns may include those fibers obtained from petroleum-derived resins.
  • Composite cords are also contemplated wherein the cords include chemically distinct yarns such as, for example, PET yarn produced by the present invention in combination with nylon yarn.
  • the tire cord fabrics can be woven from only PET yarns produced in accordance with this invention; i.e. the cords of the fabric include only fibers produced by the present invention.
  • the fabrics include cord obtained from the present invention and cords obtained from other sources.
  • a fabric can be woven using PET cord produced by the present invention and other cord obtained from other sources.
  • These other cords may include, for example, cords made from natural fibers or recycled fibers.
  • the other cords include those fabricated from petroleum-derived fibers.
  • the tires can include metal reinforcement made from recycled steel and/or other circular or sustainable metals.

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Abstract

L'invention concerne un procédé consistant (a) à fournir une charge d'alimentation qui comprend des matières carbonées ; (b) à gazéifier la charge d'alimentation pour produire un flux gazeux comprenant du monoxyde de carbone, de l'hydrogène et du dioxyde de carbone ; (c) à convertir au moins une partie du monoxyde de carbone, de l'hydrogène et du dioxyde de carbone en éthanol ; (d) à convertir au moins une partie de l'éthanol en éthylène ; (e) à convertir au moins une partie de l'éthylène en oxyde d'éthylène ; (f) à convertir au moins une partie de l'oxyde d'éthylène en éthylène glycol ; (g) à combiner au moins une partie de l'éthylène glycol avec de l'acide téréphtalique ; et (h) à polymériser l'éthylène glycol et l'acide téréphtalique pour produire un polyéthylène téréphtalate.
PCT/US2024/033045 2023-06-07 2024-06-07 Polyéthylène téréphtalate produit à partir de pneus usagés Pending WO2024254475A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090246430A1 (en) * 2008-03-28 2009-10-01 The Coca-Cola Company Bio-based polyethylene terephthalate polymer and method of making same
US20110124927A1 (en) * 2009-11-24 2011-05-26 Range Fuels, Inc. Selective process for conversion of syngas to ethanol
US20110230632A1 (en) * 2010-03-18 2011-09-22 Ramin Abhari Profitable method for carbon capture and storage
US8585789B2 (en) * 2010-04-13 2013-11-19 Ineos Usa Llc Methods for gasification of carbonaceous materials
US20210095210A1 (en) * 2013-01-23 2021-04-01 Sekisui Chemical Co., Ltd. Method for producing recycled material, and tire and method for producing tire

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090246430A1 (en) * 2008-03-28 2009-10-01 The Coca-Cola Company Bio-based polyethylene terephthalate polymer and method of making same
US20110124927A1 (en) * 2009-11-24 2011-05-26 Range Fuels, Inc. Selective process for conversion of syngas to ethanol
US20110230632A1 (en) * 2010-03-18 2011-09-22 Ramin Abhari Profitable method for carbon capture and storage
US8585789B2 (en) * 2010-04-13 2013-11-19 Ineos Usa Llc Methods for gasification of carbonaceous materials
US20210095210A1 (en) * 2013-01-23 2021-04-01 Sekisui Chemical Co., Ltd. Method for producing recycled material, and tire and method for producing tire

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