WO2021133895A1 - Circular economy for plastic waste to polypropylene and lubricating oil via refinery fcc and isomerization dewaxing units - Google Patents

Circular economy for plastic waste to polypropylene and lubricating oil via refinery fcc and isomerization dewaxing units Download PDF

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Publication number
WO2021133895A1
WO2021133895A1 PCT/US2020/066810 US2020066810W WO2021133895A1 WO 2021133895 A1 WO2021133895 A1 WO 2021133895A1 US 2020066810 W US2020066810 W US 2020066810W WO 2021133895 A1 WO2021133895 A1 WO 2021133895A1
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Prior art keywords
unit
pyrolysis
fraction
refinery
polypropylene
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/US2020/066810
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English (en)
French (fr)
Inventor
Hye-Kyung Timken
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chevron USA Inc
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Chevron USA Inc
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Publication date
Application filed by Chevron USA Inc filed Critical Chevron USA Inc
Priority to CN202080089347.1A priority Critical patent/CN114846117B/zh
Priority to BR112022011754-0A priority patent/BR112022011754B1/pt
Priority to MX2022007042A priority patent/MX2022007042A/es
Priority to EP20906534.1A priority patent/EP4081617A4/en
Priority to CA3164218A priority patent/CA3164218C/en
Priority to JP2022538697A priority patent/JP7623380B2/ja
Priority to KR1020227024038A priority patent/KR20220119404A/ko
Publication of WO2021133895A1 publication Critical patent/WO2021133895A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C10G1/002—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B68—SADDLERY; UPHOLSTERY
    • B68G—METHODS, EQUIPMENT, OR MACHINES FOR USE IN UPHOLSTERING; UPHOLSTERY NOT OTHERWISE PROVIDED FOR
    • B68G15/00—Auxiliary devices and tools specially for upholstery
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
    • C07C4/04—Thermal processes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
    • C07C4/02—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by cracking a single hydrocarbon or a mixture of individually defined hydrocarbons or a normally gaseous hydrocarbon fraction
    • C07C4/06—Catalytic processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • C08F10/04—Monomers containing three or four carbon atoms
    • C08F10/06—Propene
    • 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
    • C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
    • C10G11/14—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with preheated moving solid catalysts
    • C10G11/18—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils with preheated moving solid catalysts according to the "fluidised-bed" technique
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
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    • C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
    • C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
    • 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
    • C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
    • C10G69/14—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural parallel stages only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M109/00—Lubricating compositions characterised by the base-material being a compound of unknown or incompletely defined constitution
    • C10M109/02—Reaction products
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26—DRYING
    • F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B11/00—Machines or apparatus for drying solid materials or objects with movement which is non-progressive
    • F26B11/02—Machines or apparatus for drying solid materials or objects with movement which is non-progressive in moving drums or other mainly-closed receptacles
    • F26B11/022—Arrangements of drives, bearings, supports
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26—DRYING
    • F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B25/00—Details of general application not covered by group F26B21/00 or F26B23/00
    • F26B25/001—Handling, e.g. loading or unloading arrangements
    • F26B25/003—Handling, e.g. loading or unloading arrangements for articles
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26—DRYING
    • F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B5/00—Drying solid materials or objects by processes not involving the application of heat
    • F26B5/08—Drying solid materials or objects by processes not involving the application of heat by centrifugal treatment
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
    • C10B53/00—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form
    • C10B53/07—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form of solid raw materials consisting of synthetic polymeric materials, e.g. tyres
    • 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
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1003—Waste materials
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    • C10G2300/1037—Hydrocarbon fractions
    • C10G2300/1044—Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
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    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/28—Propane and butane
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/003—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate 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

  • U.S. Pat. No. 3,845,157 discloses cracking of waste or virgin polyolefins to form gaseous products such as ethylene/olefm copolymers which are further processed to produce synthetic hydrocarbon lubricants.
  • U.S. Pat. No. 4,642,401 discloses the production of liquid hydrocarbons by heating pulverized polyolefin waste at temperatures of 150-500° C and pressures of 20-300 bars.
  • U.S. Pat. No. 5,849,964 discloses a process in which waste plastic materials are depolymerized into a volatile phase and a liquid phase.
  • the volatile phase is separated into a gaseous phase and a condensate.
  • the liquid phase, the condensate and the gaseous phase are refined into liquid fuel components using standard refining techniques.
  • U.S. Pat. No. 6,143,940 discloses a procedure for converting waste plastics into heavy wax compositions.
  • U.S. Pat. No. 6,150,577 discloses a process of converting waste plastics into lubricating oils.
  • EP0620264 discloses a process for producing lubricating oils from waste or virgin polyolefins by thermally cracking the waste in a fluidized bed to form a waxy product, optionally using a hydrotreatment, then catalytically isomerizing and fractionating to recover a lubricating oil.
  • Other documents which relate to processes for converting waste plastic into lubricating oils include U.S. Patent Nos. 6,288,296; 6,774,272; 6,822,126; 7,834,226; 8,088,961;
  • waste plastic is recycled for polypropylene polymerization.
  • the process comprises first selecting waste plastics containing polyethylene and/or polypropylene. These waste plastics are then passed through a pyrolysis reactor to thermally crack at least a portion of the polyolefin waste and produce a pyrolyzed effluent.
  • the pyrolyzed effluent is separated into offgas, a naphtha/diesel fraction, a heavy fraction, and char.
  • the C3 paraffin and C3 olefin are separated into different fractions.
  • the C3 olefin is passed to a propylene polymerization reactor to produce polypropylene.
  • the C3 paraffin is passed to a dehydrogenation unit to produce additional propylene.
  • the heavy fraction can be passed to an isomerization dewaxing unit to produce a base oil.
  • the refinery will generally have its own hydrocarbon feed flowing through the refinery units.
  • the flow volume of naphtha/diesel or a waxy heavy fraction generated from the pyrolysis of waste plastic to the refinery units can comprise any practical or accommodating volume % of the total flow to the refinery units.
  • the flow of fractions generated from the waste plastic pyrolysis for practical reasons, can be up to about 50 vol. % of the total flow, i.e., the refinery flow and the fraction flow.
  • the flow of the naphtha/diesel is an amount up to about 20 vol. % of the total flow.
  • FIG 1 depicts the current practice of pyrolyzing waste plastics to produce fuel or wax (base case).
  • Polypropylene is used widely in various consumer and industrial products. Polypropylene is the second-most widely produced commodity plastic after polyethylene with its mechanical ruggedness and high chemical resistance. Polypropylene is widely used in packaging, film, fibers for carpets and clothing, molded articles and extruded pipes. Today, only a small portion of spent polypropylene products is collected for recycling, due to the inefficiencies and ineffectiveness of the recycling efforts discussed above.
  • FIG. 1 shows a diagram of pyrolysis of waste plastics fuel or wax that is generally operated in the industry today.
  • polyethylene and polypropylene wastes are sorted together 1.
  • the cleaned polyethylene/polypropylene waste 2 is converted in a pyrolysis unit 3 to offgas 4 and pyrolysis oil (liquid product).
  • the offgas 4 from the pyrolysis unit is used as fuel to operate the pyrolysis unit 3.
  • An on-site distillation unit (not shown) separates the pyrolysis oil to produce naphtha and diesel 5 products which are sold to fuel markets.
  • the heavy pyrolysis oil fraction 6 is recycled back to the pyrolysis unit 3 to maximize the fuel yield.
  • Char 7 is removed from the pyrolysis unit 3.
  • the heavy fraction 6 is rich in long chain, linear hydrocarbons, and is very waxy (i.e., forms paraffinic wax upon cooling to ambient temperature). Wax can be separated from the heavy fraction 6 and sold to the wax markets.
  • Polypropylene is produced via polymerization of pure propylene.
  • Clean propylene can be made from a propane dehydrogenation unit.
  • propylene can be obtained from an oil refinery fluid catalytic cracking (FCC) unit, which produces a mix of propylene and propane liquefied petroleum gas (LPG).
  • FCC oil refinery fluid catalytic cracking
  • LPG propane liquefied petroleum gas
  • Pure propylene is separated from the mix using a propane/propylene splitter, a high efficiency distillation column (PP splitter).
  • a pyrolysis unit produces poor quality products containing contaminants, such as calcium, magnesium, chlorides, nitrogen, sulfur, dienes, heavy components, which products cannot be used in large quantity for blending in transportation fuels. It has been discovered that by having these products go through the refinery units, the contaminants can be captured in pre treating units and their negative impacts diminished.
  • the fuel components can be further upgraded with appropriate refinery units with chemical conversion processes, with the final transportation fuels produced by the integrated process being of higher quality and meeting the fuels quality requirements. The present process will upgrade the wax into valuable base oil.
  • the integrated process will generate a much cleaner and more pure propane stream for the propane dehydrogenation unit and ultimately for polypropylene production. These large on- spec productions allow “cyclical economy” for the recycle plastics to be feasible.
  • the carbon in and out of the refinery operations are “transparent,” meaning that all the molecules from the waste plastic do not necessarily end up in the exact olefin product cycled back to the polyolefin plants, but are nevertheless assumed as “credit” as the net “green” carbon in and out of the refinery is positive. With these integrated processes, the amount of virgin feeds needed for polypropylene plants will be reduced significantly.
  • the pyrolysis unit can be located near the waste plastics collection site, which site could be away from a refinery, near a refinery, or within a refinery.
  • the pyrolysis oil (naphtha/diesel and heavies) and wax can be transferred to the refinery by truck, barge, rail car, or pipeline. It is preferred, however, that the pyrolysis unit is within the plastics collection site or within the refinery.
  • the preferred starting material for the present process is sorted waste plastics containing predominantly polyethylene and polypropylene (plastics recycle classification types 2, 4, and 5).
  • the present process can tolerate a moderate amount of polystyrene (plastics recycle classification type 6).
  • Waste polystyrene needs to be sorted out to less than 30%, preferably less than 20% and most preferably less than 5%.
  • Non- metal contaminants include contaminants coming from the Periodic Table Group IV, such as silica, contaminants from Group V, such as phosphorus and nitrogen compounds, contaminants from Group VI, such as sulfur compounds, and halide contaminants from Group VII, such as fluoride, chloride, and iodide.
  • the residual metals, non-metal contaminants, and halides need to be removed to less than 50 ppm, preferentially less than 30ppm and most preferentially to less than 5ppm.
  • the pyrolyzing is carried out by contacting a plastic material feedstock in a pyrolysis zone at pyrolysis conditions, where at least a portion of the feed(s) is cracked, thus forming a pyrolysis zone effluent comprising 1 -olefins and n-paraffins.
  • Pyrolysis conditions include a temperature of from about 400° C to about 700° C, preferably from about 450° C to about 650° C.
  • Conventional pyrolysis technology teaches operating conditions of above-atmospheric pressures. See e.g.. U.S. Pat. No. 4,642,401. Additionally, it has been discovered that by adjusting the pressure downward, the yield of a desired product can be controlled. See, e.g., U.S. Pat. No. 6,150,577. Accordingly, in some embodiments where such control is desired, the pyrolysis pressure is sub-atmospheric.
  • FIG. 2 shows the present integrated process where only the naphtha/diesel fraction from the pyrolysis is sent to an FCC unit 28.
  • the naphtha/ diesel fraction is fed either to the FCC reactor or to the distillation column depending on the feed quality.
  • the fluid catalytic cracking (FCC) process is widely used in the refining industry for conversion of atmospheric gas oil, vacuum gas oil, atmospheric residues and heavy stocks recovered from other refinery operations into high-octane gasoline, light fuel oil, heavy fuel oil, olefin-rich light gas (LPG) and coke.
  • FCC fluid catalytic cracking
  • FCC uses a high activity zeolite catalyst to crack the heavy hydrocarbon molecules at a 950-990° F reactor temperature in a riser with a short contact time of a few minutes or less.
  • LPG streams containing olefins are commonly upgraded to make alkylate gasoline, or to be used in chemicals manufacturing.
  • a conventional FCC unit is used.
  • the refinery will generally have its own hydrocarbon feed flowing through the refinery units.
  • the flow volume of naphtha/diesel generated from the pyrolysis of waste plastic to the refinery units, here an FCC unit can comprise any practical or accommodating volume % of the total flow to the refinery units.
  • the flow of the naphtha/diesel fraction generated from the waste plastic pyrolysis for practical reasons, can be up to about 50 vol. % of the total flow, i.e., the refinery flow and the naphtha/diesel flow.
  • the flow of the naphtha/diesel is an amount up to about 20 vol. % of the total flow.
  • the flow of the naphtha/diesel is an amount up to about 10 vol. % of the total flow. About 20 vol. % has been found to be an amount that is quite practical in its impact on the refinery while also providing excellent results and being an amount that can be accommodated.
  • the amount of naphtha/diesel generated from the pyrolysis can of course be controlled so that the fraction passed to the refinery units provides the desired volume % of the flow. Flow of the heavy fraction to the dewaxing unit can similarly be controlled and/or adjusted.
  • the FCC unit 28 produces a liquefied petroleum gas olefin streams 29 comprising C3UC3 olefin/paraffm mix and CU/C4 olefin/paraffm mix.
  • the C3 olefin/paraffm mix is recovered at 40, then the propane and propylene stream is split by a PP splitter 31 to produce pure streams of propane 32 and propylene 33.
  • the propylene stream 33 can be fed directly to the polypropylene unit 35 to produce polypropylene resin. Polypropylene consumer products can then be made 36.
  • the pure propane 32 can be fed to a propane dehydrogenation unit 34 to make additional propylene, and then ultimately polypropylene in a propylene polymerization unit 35.
  • Polypropylene is produced via chain-growth polymerization from the monomer propylene.
  • a Ziegler-Natta catalyst or metallocene catalyst is used to catalyze the polymerization of propylene to polypropylene polymer with desired properties. These catalysts are activated with special cocatalyst containing an organoaluminum compounds.
  • the industrial polymerization processes uses either gas phase polymerization in a fluidized bed reactor or bulk polymerization in loop reactors.
  • the gas phase polymerization typically runs at 50-90° C temperature and a pressure of 8-35 atm in the presence of Fh.
  • the bulk polymerization proceeds at 60 to 80° C and 30-40 atm pressure is applied to keep the propylene in liquid state.
  • the propylene polymerization unit is preferably located near the refinery so that the feedstock (propylene) can be transferred via pipeline.
  • the feedstock can be delivered via truck, barge, rail car or pipeline.
  • the C430 and heavy hydrocarbon product 37 from the FCC unit can be sent to appropriate refinery units 45 for upgrading into clean gasoline, diesel, or jet fuel.
  • the heavy, waxy pyrolysis oils or wax 26 from the pyrolysis unit 23 can be sent to a base oil dewaxing unit, generally an isomerization dewaxing unit 38 with a precious metal containing zeolite catalyst for hydroisomerization to produce lubricating base oil with excellent viscosity index and pour point.
  • the flow of the heavy, waxy fraction can be controlled and adjusted as needed based upon the amount desired to be accommodated.
  • the isomerization dewaxing unit converts paraffinic, waxy heavy hydrocarbon material, typically boiling about 650° F, to high viscosity index (VI) lube oils.
  • the unit typically consists of a feed hydrotreating section, isomerization dewaxing section, and distillation section.
  • Typical hydrotreating conditions which are employed to remove contaminants while avoiding cracking include temperatures ranging from about 190° C (374° F) to about 340° C (644° F), pressure ranging from about 400 psig to about 3000 psig, space velocities (LHSV) in the range of about 0.1 hr 1 to about 20 hr 1 , and hydrogen recycle rates ranging from about 400 to about 15,000 SCF/B.
  • Hydrotreating catalysts include those conventionally used in hydrotreating units, containing metals such as Ni, Mo, Co, W and porous supports such as alumina, silica, or silica- alumina.
  • the hydrotreated heavy hydrocarbon is sent to the dewaxing reactor with an isomerization dewaxing catalyst which contains noble metal, intermediate pore size molecular sieve and binder.
  • the catalyst preferably contains an intermediate pore size (10-membered ring) molecular sieve such as ZSM-23, ZSM-35, ZSM-48, ZSM-5, SSZ-32, SSZ-91, SAPO-11, SAPO-31 and SAPO-41.
  • the noble metal includes Group VIII metals, such as Pt, Pd or mixture of Pt and Pd.
  • porous alumina or silica is used to bind the material to produce catalyst pellets for the fixed bed reactor.
  • Typical reaction conditions for the dewaxing reactor include temperature range of 200° C (392° F) to about 475° C (887° F), pressure ranging from about 200 psig to about 3000 psig, space velocities (LHSV) in the range of about 0.2 hr 1 to about 10 hr 1 , and hydrogen recycle rates ranging from about 400 to about 15,000 SCF/B.
  • the isomerization dewaxing catalyst converts n-paraffins to iso-paraffins, thereby reducing the pour point of the resulting oils and to form a high VI lube oil.
  • the effluent hydrocarbon from the isomerization dewaxing section is sent to a distillation unit to separate the effluent into various oil fractions, e.g., a base oil fraction that boils above -650° F, a diesel fraction that boils about 300 - 700° F, and a gasoline fraction that boils about 80 - 400° F.
  • various oil fractions e.g., a base oil fraction that boils above -650° F, a diesel fraction that boils about 300 - 700° F, and a gasoline fraction that boils about 80 - 400° F.
  • the boiling points for the gasoline, jet and diesel fractions will be adjusted depending on the season and local specifications.
  • Example 1 Properties of Pyrolysis Oil and Wax From Commercial Sources
  • Pyrolysis oil and wax samples were obtained from commercial sources and their properties are summarized in Table 1. These pyrolysis samples were prepared from waste plastics containing mostly polyethylene and polypropylene via thermal decomposition in a pyrolysis reactor at around 400-600° C, near atmospheric pressure without any added gas or a catalyst.
  • a pyrolysis unit typically produces gas, liquid oil product, optionally wax product, and char.
  • the pyrolysis unit ’s overhead gas stream containing thermally cracked hydrocarbon was cooled to collect condensate as pyrolysis oil (liquid at ambient temperature) and/or pyrolysis wax (solid at ambient temperature).
  • the pyrolysis oil is the main product of the pyrolysis units. Some units produce pyrolysis wax as a separate product in addition to the pyrolysis oil.
  • ASTM D4052 method was used for specific gravity measurements. Simulated boiling point distribution curve was obtained using ASTM D2887 method. Carlo-Erba analysis for carbon and hydrogen was based on ASTM D5291 method. Bromine number measurement was based on ASTM D1159 method. Hydrocarbon-type analysis was done using a high resolution magnetic mass spectrometer using the magnet scanned from 40 to 500 Daltons. Total sulfur was determined using XRF per ASTM D2622 method. The nitrogen was determined using a modified ASTM D5762 method using chemiluminescence detection. The total chloride content was measured using combustion ion chromatography instrument using modified ASTM 7359 method.
  • the oxygen content in naphtha and distillate boiling range was estimated using GC by GC/MS measurements with electron ionization detector for m/Z range of 29-500. Trace metal and non-metal elements in oil were determined using inductively coupled plasma-atomic emission spectrometry (ICP-AES).
  • ICP-AES inductively coupled plasma-atomic emission spectrometry
  • Industrial pyrolysis process of sorted plastics sourced predominantly from polyethylene and polypropylene waste, produced quality hydrocarbon streams with specific gravity ranging 0.7 to 0.9, and a boiling range from 18 to 1100° F as in pyrolysis oil or pyrolysis wax.
  • the pyrolysis product is rather pure hydrocarbon made of mostly carbon and hydrogen.
  • the hydrogen to carbon molar ratio varies from 1.7 to near 2.0.
  • the Bromine Number is in the range of 14 through 60 indicating varying degrees of unsaturation coming from olefins and aromatics.
  • the aromatic content is in the range of 5 to 23 volume % with a higher severity unit producing more aromatics.
  • the pyrolysis products show paraffinic content ranging from mid-20 vol. % to mid-50 vol. %.
  • the pyrolysis product contains a substantial amount of olefins.
  • Example 2 Fractionation of Pyrolysis Oil for Evaluation As Transportation Fuel
  • Sample D was distilled to produce hydrocarbon cuts representing gasoline (350° F ), jet (350 - 572° F), diesel (572 - 700° F) and the heavy (700° F + ) fractions.
  • Table 2 summarizes the boiling point distribution and impurity distributions among the distilled product fractions.
  • Example 3 Evaluation of Pyrolysis Oil Cut for Gasoline Fuel
  • Sample F a pyrolysis oil cut for gasoline fuel boiling range, was evaluated to assess its potential to use as gasoline fuel.
  • Sample F has the carbon number range of C5 - C12, typical of the gasoline fuel.
  • Sample F a pyrolysis oil cut for gasoline fuel boiling range, cannot be used by itself as automotive gasoline fuel due to its poor quality.
  • the gasoline fraction from the pyrolysis oil showed very poor oxidation stability in that Sample F failed only after 90 min compared to the target stability of longer than 1440 minutes.
  • the pyrolysis gasoline exceeded the wash gum target of 4 mg/ 100 mL suggesting severe gum forming tendency.
  • the pyrolysis gasoline has poor octane numbers compared to the reference gasoline. A premium unleaded gasoline was used as the reference gasoline.
  • Example 4 Evaluation of Pyrolysis Oil Cut for Jet Fuel
  • Sample G a pyrolysis oil cut for jet fuel boiling range, was evaluated to assess its potential to use as jet fuel.
  • Sample G has the carbon number range of C9 - C18, typical of the jet fuel.
  • Example 5 Evaluation of Pyrolysis Oil Cut for Diesel Fuel
  • Sample H a pyrolysis oil cut for diesel fuel boiling range, was evaluated to assess its potential to use as diesel fuel.
  • Sample H has the carbon number range of C14 - C24, typical of the diesel fuel.
  • Sample H contains a substantial amount of normal hydrocarbons. Since normal hydrocarbons tends to exhibit waxy characteristics, cold flow properties such as pour point (ASTM D5950-14) and cloud points (ASTM D5773) were considered as the most critical tests.
  • Results from Table 1 showed that industrial pyrolysis process of sorted plastics, sourced predominantly from polyethylene and polypropylene waste, produced quality pyrolysis oil or pyrolysis wax made of mostly carbon and hydrogen. With good sorting and efficient pyrolysis unit operation, the nitrogen and sulfur impurities are at low enough levels that a modem refinery can handle cofeeding of pyrolysis feedstocks to their processing units with no detrimental impacts.
  • pyrolysis oils or wax may still contain high amounts of metals (Ca, Fe, Mg) and other non-metals (N, S, P, Si, Cl, O) that could negatively affect the performance of conversion units in a refinery.
  • metals Ca, Fe, Mg
  • other non-metals N, S, P, Si, Cl, O
  • pyrolysis products with high impurity levels are preferentially fed to a FCC feed treater unit before the FCC unit so that bulk of impurities are removed effectively by the pretreater.
  • the pyrolysis oil and wax are converted into offgas, LPG paraffins and olefins, FCC gasoline and heavy hydrocarbon components.
  • the FCC gasoline is a valuable gasoline blending component.
  • the heavy fractions, light cycle oil (LCO) and heavy cycle oil (HCO) are converted further in the subsequent conversion units including jet hydrotreating unit, diesel hydrotreating unit, hydrocracking unit and/or coker unit to make more gasoline, jet, and diesel fuel with satisfactory product properties.
  • the LPG paraffins and olefins are either processed further in an alkylation unit, blended in the gasoline poor or in part used for petrochemicals production with a recycle content.
  • the C3 propane and propylene mix steam is a valuable feedstock for polypropylene generation.
  • Examples 7 and 8 demonstrate the conversion of waste plashes pyrolysis product into quality transportation fuel in a refinery conversion unit, using a FCC unit as an example.
  • VGO Vacuum gas oil
  • Ecat regenerated equilibrium catalyst
  • the FCC unit cracks the pyrolysis oil info fuel range hydrocarbons, reduces impurities, and isomerize n-paraffins to isoparaffins. All these chemistry will improve the fuel properties of the pyrolysis oil and wax.
  • a zeolite catalyst By cofeeding the pyrolysis oil through the FCC process unit with a zeolite catalyst, the oxygen and nitrogen impurities in the fuel range were reduced substantially, from about 300-1400 ppmN to about 30 ppmN and from about 250-540 ppm O to about 60-80 ppm O.
  • the hydrocarbon composition of all these cofeeding products are well within the typical FCC gasoline range.
  • Example 8 Feeding of Recycled C3 for Propylene Isolation or Production, followeded by Productions of Polypropylene Resin and Polypropylene Consumer Products
  • the pyrolysis oil cofeeding to a FCC unit, as shown in Example 7 produces a substantial amount of C3 LPG steam with a recycle content.
  • the C3 stream is a good feedstock to feed to a polymerization unit for production of polypropylene polymer with a recycle content.
  • the C3 LPG stream containing propane and propylene is captured and fed to a propane/propylene (P/P) splitter to isolate a pure propylene steam (>99 mol%), which is then fed to a propylene polymerization unit.
  • the propane from the P/P splitter may be dehydrogenated to produce additional propylene for the polymerization unit.
  • the polypropylene resin containing some recycled-polyethylene/ polypropylene derived materials has high quality that is indistinguishable to that of the virgin polypropylene resin made entirely from virgin petroleum resources.
  • the polypropylene resin with the recycled material is then further processed to produce various polypropylene products to fit the needs of consumer products.
  • These polypropylene consumer products now contain chemically recycled, circular polymer while qualifies of the polypropylene consumer products are indistinguishable from those made entirely from virgin polypropylene polymer.
  • These chemically recycled polymer products are different from the mechanically recycled polymer products whose qualities are inferior to the polymer products made from virgin polymers.
  • Results from Table 1 showed that industrial pyrolysis process of sorted plastics, sourced predominantly from polyethylene and polypropylene waste, produced pyrolysis wax made of mostly carbon and hydrogen.
  • Various process options were examined for making lubricating base oil from the pyrolysis wax via hydroisomerization dewaxing process.
  • the pyrolysis wax still contain too high amounts of nitrogen and sulfur impurities, metals (Ca, Fe, Mg) and other non-metals (P, Si, Cl, O) that negatively affect the performance of the hydroisomerization dewaxing catalyst containing precious metal (Pt, Pd, or a combination of Pt and Pd) and a zeolite such as ZSM-11, ZSM-23, ZSM-48, SSZ-32, SSZ-91, SAPO-11, SAPO-31 and SAPO-41.
  • precious metal Pt, Pd, or a combination of Pt and Pd
  • a zeolite such as ZSM-11, ZSM-23, ZSM-48, SSZ-32, SSZ-91, SAPO-11, SAPO-31 and SAPO-41.
  • the volume percent limitation is likely coming from the nitrogen impurity which is detrimental to the zeolite activity.
  • the nitrogen level of the combined feed needs to be maintained at less than 5 ppm nitrogen, preferentially less than 1 ppm nitrogen.
  • the pyrolysis wax is cofed to a hydrocracking unit to remove S, N, and other impurities.
  • the hydrocracking unit hydrogenates the pyrolysis wax and removes impurities.
  • the hydrocracking unit severity may be adjusted to maximize the base oil yield of the combined feed.
  • Cofeeding level to the hydrocracking unit can be as much as 50 vol. %, preferentially 20 vol. %. In this case, the volume percent limitation may come from the metals impurity or N impurity or P impurity depending on the unit configuration and the catalyst choice.
  • the bottom fraction (650° F+) containing hydrocracked pyrolysis wax is then fed to the hydroisomerization dewaxing unit to make a lubricating base oil.
  • Example 10 demonstrate an unsuccessful route and a successful process route of making quality base oil in refinery conversion units using waste plastics pyrolysis wax as the feedstock.
  • Example 10 Production of Base Oil from Recycled Pyrolysis Wax via Hydroisomerization Dewaxing Process Only
  • Sample E crude pyrolysis wax
  • Sample J 100% Sample J was hydroisomerized in a batch autoclave unit with a Pt/SSZ-32/Alumina catalyst overnight at an oil to catalyst weight ratio of 10:1, at 650° F and under 800 psig 3 ⁇ 4 pressure.
  • the hydrogenated product was vacuum distilled to produce 690° F + boiling and clear oil, Sample K. Properties of the samples are summarized in Table
  • Sample J 690° F + cut slack wax from waste plastic pyrolysis, is low-viscosity wax at ⁇ 4.3 cSt at 100° C with an excellent viscosity index of 169.
  • the slack wax contains significant amounts of N (180 ppm) and P (32.5 ppm) which will passivate the zeolite catalyst activity in the hydroisomerization dewaxing process.
  • Sample K dewaxed and distilled oil, showed viscosity index of 162 and the pour point of 12° C.
  • Example 11 Production of Quality Base Oil with Recycle Content by Hydrotreating followeded by Hydroisomerization Dewaxing Process
  • Sample E crude pyrolysis wax
  • a liquid feed flow rate of 1.5 hr 1 relative to the catalyst bed volume and H2/Hydrocarbon flow rate of 2500 scf/bbl were used to produce the hydrogenated product, which is mostly wax.
  • the hydrogenated product was vacuum distilled to produce 650° F + fraction as a hydrogenated pyrolysis paraffin wax, Sample L.
  • Sample L hydrogenated wax made from waste plastics pyrolysis
  • a continuous fixed bed unit containing a Pt/ZZS-91/Alumina catalyst at 625° F reactor temperature and 400 psig pressure.
  • a liquid feed flow rate of 1.0 hr 1 relative to the catalyst bed volume and H2/Hydrocarbon flow rate of 2500 scf/bbl were used to produce the dewaxed oil.
  • the dewaxed oil was vacuum distilled to produce 690° F + fraction as the final dewaxed base oil product, Sample M. The results are summarized in Table 8.
  • the word “comprises” or “comprising” is intended as an open-ended transition meaning the inclusion of the named elements, but not necessarily excluding other unnamed elements.
  • the phrase “consists essentially of’ or “consisting essentially of’ is intended to mean the exclusion of other elements of any essential significance to the composition.
  • the phrase “consisting of’ or “consists of’ is intended as a transition meaning the exclusion of all but the recited elements with the exception of only minor traces of impurities.

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US11959025B2 (en) 2024-04-16
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CA3164218A1 (en) 2021-07-01
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