WO2023187072A1 - Procédé de production de carburant de transport - Google Patents

Procédé de production de carburant de transport Download PDF

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Publication number
WO2023187072A1
WO2023187072A1 PCT/EP2023/058325 EP2023058325W WO2023187072A1 WO 2023187072 A1 WO2023187072 A1 WO 2023187072A1 EP 2023058325 W EP2023058325 W EP 2023058325W WO 2023187072 A1 WO2023187072 A1 WO 2023187072A1
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hydroconversion
transportation fuel
process according
stream
fraction
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PCT/EP2023/058325
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English (en)
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Christian Ejersbo STREBEL
Trine Marie Hartmann DABROS
Peter Andreas NYMANN
Ole Frej ALKILDE
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Topsoe A/S
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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
    • C10G1/10—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/50—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
    • 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
    • C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
    • C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
    • C10G47/10—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used with catalysts deposited on a carrier
    • C10G47/12—Inorganic carriers
    • C10G47/16—Crystalline alumino-silicate carriers
    • 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
    • C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
    • C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
    • C10G65/12—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including cracking steps and other hydrotreatment steps
    • 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
    • C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
    • C10G69/06—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one step of thermal cracking in the absence of hydrogen
    • 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
    • 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
    • C10G2300/1011—Biomass
    • C10G2300/1014—Biomass of vegetal origin
    • 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
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline
    • 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
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/04—Diesel oil

Definitions

  • the present invention relates to a process for production of quality transportation fuels by hydroconversion of liquid cyclic hydrocarbonaceous feedstocks which may be formed from solid hydrocarbonaceous materials e.g. tires or lignocellulosic solids by thermochemical decomposition.
  • Thermochemical decomposition such as pyrolysis or hydrothermal liquefaction (HTL) of certain raw materials having an aromatic structure, such as waste tires and rubber, will provide liquids (for convenience pyrolysis oil) having a high content of ring structures like aromatics and naphthenes. Similar liquids may also be provided as tar from coke ovens and pyrolysis of lignite. While a large fraction of such pyrolysis oil boils in the middle distillate range, the dominance of cyclic compounds means that such cyclic pyrolysis oil boiling in the middle distillate range is not suited for use as a quality middle distillate transportation fuel.
  • the process will be more selective towards saturation of aromatics as well as addition of hydrogen to cyclic structures if the hydrogen partial pressure is elevated, e.g. by increasing the total process pressure.
  • thermochemical decomposition shall for convenience be used broadly for any decomposition process, in which a material is partially decomposed at elevated temperature (typically 250°C to 800°C or even 1000°C), in the presence of substoichiometric amount of oxygen (including no oxygen).
  • elevated temperature typically 250°C to 800°C or even 1000°C
  • the product will typically be a combined liquid and gaseous stream, as well as an amount of solid char.
  • the term shall be construed to include processes known as pyrolysis and hydrothermal liquefaction, both in the presence and absence of a catalyst.
  • thermochemical decomposition such as pyrolysis and thermal liquefaction
  • pyrolysis oil irrespective of the nature of the originating process.
  • vol% shall be used to signify volume percentage for a gas.
  • ppm w shall be used to signify weight parts per million, e.g. the mass of sulfur atoms relative to the mass of a liquid hydrocarbon stream.
  • wt% shall be used to signify weight percentage.
  • aromatic molecule shall for the purpose of the present application be used to signify homocyclics with a conjugated stable bond structure in accordance with IIIPAC terminology, comprising only carbon atoms in the aromatic ring, as well as heterocyclics, comprising one or more atoms other than carbon and hydrogen, such as oxygen, sulfur and nitrogen.
  • the term shall also cover both conjugated monocyclics and polycyclics, including fused aromatics.
  • the aromatic content of a liquid is in accordance with the art the total mass of molecules having at least one aromatic structure, relative to the total mass of all molecules in %.
  • the content of carbon in cyclic structures is in accordance with the definition of aromatic content the total mass of carbon atoms in molecules having at least one cyclic structure, relative to the total mass of carbon in all molecules in %.
  • the pressure and temperature shall in accordance with the terminology of the skilled person of refinery technology in the following be construed as the pressure and temperature respectively at the inlet of a reactor.
  • the hydrogen partial pressure shall be construed as the partial pressure of hydrogen in the treat gas.
  • the space velocity shall in accordance with the terminology of the skilled person of refinery technology in the following be construed as the LHSV (liquid hourly space velocity) over a single catalytically active material unless otherwise indicated.
  • the initial boiling point (IBP), the final boiling point (FBP) and the temperatures corresponding to recovered amounts of sample, shall be understood in accordance with the ASTM D86 standard.
  • T5, T10, T50 and T95 boiling points shall accordingly be understood as the distillation temperatures where 5vol%, 10vol%, 50vol% and 95vol% respectively have been recovered.
  • thermochemical decomposition such as pyrolysis and thermal liquefaction
  • condensation of biomass and waste to liquid products by thermochemical decomposition is, especially with subsequent hydrotreatment, considered an environmentally friendly source for alternatives to petroleum products, especially from a global warming perspective.
  • Due to the nature of these liquid products (for simplicity pyrolysis oil, irrespective of the originating process) they will require upgrading, e.g. by hydrotreatment to remove heteroatoms, such as sulfur and oxygen, and to hydrogenate olefinic structures.
  • the nature of formation means that the products are not stabilized, and therefore, contrary to typical fossil raw feedstocks, they may be very reactive, demanding high amounts of hydrogen, releasing significant amounts of heat during reaction and furthermore having a high propensity towards polymerization. The release of heat may increase the polymerization further, and at elevated temperature catalysts may also be deactivated by coking.
  • thermochemical decomposition process plant section providing the hydrocarbonaceous feedstock according to the present disclosure may be in many forms including rotary oven, fluidized bed, transported bed, or circulating fluid bed, as is well known in the art.
  • This decomposition converts a pyrolysis feedstock into a solid (char), a high boiling liquid (tar) and fraction being gaseous at elevated temperatures.
  • the gaseous fraction comprises a fraction condensable at standard temperature (pyrolysis oil or condensate, C5+ compounds) and a non-condensable fraction (pyrolysis gas, including pyrolysis off-gas).
  • the thermochemical decomposition process plant section may comprise a pyrolizer unit (pyrolysis reactor), cyclone(s) and/or filters to remove particulate solids such as char, and a cooling unit for thereby producing pyrolysis off-gas stream and said pyrolysis oil stream, i.e. condensed pyrolysis oil.
  • the pyrolysis gas stream comprises light hydrocarbons e.g. C1-C4 hydrocarbons, and commonly also H2O, CO and CO2.
  • the term pyrolysis oil comprises condensate and tar
  • the pyrolysis oil stream from pyrolysis of biomass may also be referred to as bio-oil or biocrude.
  • the pyrolysis oil is a liquid substance rich in blends of molecules, usually consisting of more than two hundred different compounds mainly oxygenates such as acids, sugars, alcohols, phenols, guaiacols, syringols, aldehydes, ketones, furans, and other mixed oxygenates, resulting from the depolymerization of the solids treated in pyrolysis.
  • oxygenates such as acids, sugars, alcohols, phenols, guaiacols, syringols, aldehydes, ketones, furans, and other mixed oxygenates, resulting from the depolymerization of the solids treated in pyrolysis.
  • Thermochemical decomposition of non- biological waste comprising suitable compositions, such as plastic fractions or rubber, including end of life tires will only provide products which contain low concentrations of oxygen, unless oxygen is added to the decomposition process and will commonly provide a hydrocarbonaceous feedstock which has a structure similar to that of tar from co
  • the pyrolysis section may be fast pyrolysis, also referred to in the art as flash pyrolysis.
  • Fast pyrolysis means the thermochemical decomposition of a solid renewable feedstock typically in the absence of oxygen, at temperatures typically in the range 350-650°C e.g. about 500°C and reaction times of 10 seconds or less, such as 5 seconds or less, e.g. about 2 sec.
  • Fast pyrolysis may for instance be conducted by autothermal operation e.g. in a fluidized bed reactor.
  • the latter is also referred to as autothermal pyrolysis and is characterized by employing air, optionally with an inert gas or recycle gas, as the fluidizing gas.
  • a catalyst may be used.
  • An acid catalyst commonly comprising a zeolite, without active metals, may be used to upgrade the pyrolysis vapors, and it can both be operated in an in-situ mode (the catalyst is located in the pyrolysis reactor) and an ex-situ mode (the catalyst is placed in a separate reactor).
  • the use of a catalyst conveys the advantage of helping to stabilize the pyrolysis oil and thereby making it easier to hydroprocess.
  • increased selectivity towards desired pyrolysis oil compounds may be achieved.
  • hydrogen is added to the catalytic pyrolysis which is then called reactive catalytic fast pyrolysis. If the catalytic pyrolysis is conducted at a high hydrogen pressure, such as above 0.5 MPa, it is often called catalytic hydropyrolysis.
  • the catalyst for upgrading in the presence of hydrogen will typically comprise one or more metals active in hydrogenation, such as a metal from Group 6 or Group 8,9 or 10.
  • the pyrolysis stage may be fast pyrolysis which is conducted without the presence of a catalyst and hydrogen, i.e. the fast pyrolysis stage is not catalytic fast pyrolysis, hydropyrolysis or catalytic hydropyrolysis. This enables a much simpler and inexpensive process.
  • the thermochemical decomposition section may also be hydrothermal liquefaction. Hydrothermal liquefaction means the thermochemical conversion of solid waste and biomass into liquid fuels by processing in a hot, pressurized water environment for sufficient time to break down the solid polymeric structure to mainly liquid components. Typical hydrothermal processing conditions are temperatures in the range of 250-375°C or even up to 500°C and operating pressures in the range of 4-40 MPa. This technology offers the advantage of operation of a lower temperature, higher energy efficiency and producing a product with a lower oxygen content compared to pyrolysis, e.g. fast pyrolysis.
  • thermochemical decomposition methods are intermediate or slow pyrolysis, in which the conditions involve a lower temperature and commonly higher residence times - these methods may also be known as carbonization or torrefaction.
  • the major benefit of these thermochemical decomposition methods is a lower investment, but they may also have specific benefits for specific feedstocks or for specific product requirements, such a need for bio-char.
  • thermochemical conversion process When high amounts of solid product are produced, such as processes producing bio-char or when retrieval of unconverted carbon black particles from thermochemical conversion of end-of-life tires is desired, it may be beneficial to filter the liquid product as part of the thermochemical conversion process, which will also have the benefit of minimizing deactivation of downstream catalyst.
  • the conversion of a hydrocarbonaceous feedstock comprising oxygenates to hydrocarbons is a common process for production of renewable transportation fuels from oils and fats, but the reactivity and other specifics differ for different feedstocks.
  • the cyclic hydrocarbonaceous feedstock of the present disclosure typically comprises a high amount of cyclic structures and may also comprise oxygenates taken from the group consisting of ketones, aldehydes or alcohols, but commonly only low amounts of carboxylic acids.
  • thermochemical decomposition of non-biological waste such as plastic and rubber fractions, including end of life tires, as well as from biological materials rich in lignin, such as straw and waste from wood processing or solid fossil feedstocks such as lignite, typically after a thermal and/or catalytic degradation process.
  • lignin such as straw and waste from wood processing or solid fossil feedstocks such as lignite
  • the feedstock and the product will be characterized by having a 14 C content above 0.5 parts per trillion of the total carbon content, but when the feedstock includes waste of fossil origin, such as plastic, this ratio may be different.
  • hydrocarbon products typically requires one or more hydroprocessing steps which most commonly are; hydrotreatment for removing heteroatoms and saturating double bonds, hydroisomerization for adjusting hydrocarbon molecule structure and hydroconversion for reducing hydrocarbon molecular weight, and according to the present disclosure, hydrodearomatization is also of relevance.
  • hydrotreatment the hydrocarbonaceous feedstock is combined with an excess of hydrogen and react in hydrodeoxygenation processes, where water is released from the oxygenates.
  • oxygenates involve carbonyl groups
  • decarboxylation and decarbonylation processes releasing carbon dioxide and carbon monoxide may also take place, and in that case an equilibrium between carbon dioxide and carbon monoxide exists according to the water/gas shift process, but this is less common in the types of cyclic hydrocarbonaceous feedstock according to the present disclosure.
  • the oxygen content will be low, such as from 0.5 wt% and up to 5wt%, whereas for pyrolysis oil from bambooous compounds it will be higher, such as, from 5 wt%, 10 wt% or even 25 wt% to 50wt% of the oxygenate feedstock is oxygen, and thus a significant amount of the product stream will be water, carbon dioxide and carbon monoxide.
  • an amount of light hydrocarbons may also be present in the product stream, depending on the nature of the feedstock and the side reactions occurring.
  • Hydrotreatment may also involve extraction of other hetero-atoms, notably nitrogen and sulfur but possibly also halogens and silicon as well as the saturation of double bonds.
  • catalyst activity is commonly controlled by only using low amounts of active metals and especially limiting the amount of promoting metals, such as nickel and cobalt. Commonly such a material with moderate activity is followed by a more active material, ensuring close to complete hydrotreatment.
  • the material catalytically active in hydrotreatment may commonly comprise from at least 1 wt%, at least 5 wt% or at least 8 wt% to at most 15 wt%, at most 20 wt% or at most 25 wt% molybdenum or tungsten, promoted by an amount of nickel in the range from 0.01 :1 Ni:Mo+W to 0.1 :1 Ni:Mo+W (where the ratios designate molar ratios between the amount of Ni and the total amount of Mo and W) on a refractory oxidic support such as alumina, silica or titania, which typically is amorphous.
  • a corresponding active catalyst may comprise a higher amount of Ni, such as 0.1 :1 Ni:Mo+Wto 0.5:1 Ni:Mo+W, whereas even more elevated ratios would typically correspond to hydrodearomatization catalysts.
  • cobalt may have an effect similar to that of nickel.
  • the catalyst may comprise further components, such as boron or phosphorous in combination with the active metals and/or the support.
  • the conditions are typically a temperature in the interval 250-400°C, a pressure in the interval 3-15 MPa, and a liquid hourly space velocity (LHSV) in the interval 0.1-2 hr 1 .
  • the deoxygenation will involve a combination of hydrodeoxygenation producing water and if the oxygenates comprise carboxylic groups such as acids or esters, decarboxylation producing CO2.
  • the deoxygenation of carboxylic groups may proceed by hydrodeoxygenation or decarboxylation with a selectivity which, depending on conditions and the nature of the catalyst may vary from above 90% hydrodeoxygenation to above 90% decarboxylation.
  • sulfur is removed by hydrodesulfurization, typically producing H2S. Hydrodesulfurization and deoxygenation by both routes is exothermal, and with the presence of a high amount of oxygen, the process may involve intermediate cooling e.g. by quenching with cold hydrogen, feed or product.
  • the feedstock may preferably contain an amount of sulfur to maintain sulfidation of the metals, in order to maintain their activity. If the feedstock stream comprising oxygenates comprises less than 10, 100 or 500 ppm w sulfur, a sulfide donor, such as dimethyldisulfide (DMDS) has typically been added to the feed.
  • DMDS dimethyldisulfide
  • a pre-treatment at moderate conditions may be relevant, to stabilize the feedstock. This may involve an inlet temperature as low as 80°C, 120°C or 200°C, a pressure in the interval 3-15 MPa, and a liquid hourly space velocity (LHSV) in the interval 0.1-2 hr 1 and a deliberate choice of less active catalyst, such as unpromoted or weakly promoted molybdenum e.g. in a concentration from 5 wt% to 15 wt% on a refractory support. Due to the reactive components and the exothermal nature thermal control by quenching or recycle may be relevant in this pre-treatment step.
  • LHSV liquid hourly space velocity
  • the hydrotreatment process may provide a product rich in aromatic molecules and naphthenes. These molecules have poor diesel properties, including density (specific gravity) and cetane index. Traditionally aromatic molecules have been converted by saturation over a hydrotreatment catalyst. As the equilibrium between aromatic and non-aromatic rings favors aromatics at high temperature, moderate temperatures and thus high activity catalysts have been preferred, which has implied use of noble metals, which are catalytically active at lower temperatures than sulfided base metals.
  • Hydroconversion chemically involves the breaking of carbon-carbon bonds in hydrocarbons by addition of hydrogen.
  • This process is typically used in the form of hydrocracking to adjust the boiling point characteristics of a hydrocarbon mixture, by cracking large molecules into smaller, but the breaking of carboncarbon bonds will also have the effect of opening rings in cyclic molecules.
  • This ring-opening will have the related effect of shifting the equilibrium of hydrodearomatization by converting the non-aromatic product such that this reaction no longer is equilibrium limited, and thus ring-opening will indirectly have the effect of reducing the content of aromatics.
  • hydroconversion involves directing an intermediate feedstock to contact a hydroconversion catalyst comprising an active metal (either elemental noble metals such as platinum and/or palladium or sulfided base metals such as nickel, cobalt, tungsten and/or molybdenum), an acidic support (typically a molecular sieve showing high activity in breaking carbon-carbon bonds, and having a topology such as MFI, BEA and FAU) and a refractory support (such as alumina, silica or titania, or combinations thereof).
  • the catalyst may comprise further components, such as boron or phosphorous.
  • the conditions are typically a temperature in the interval 250-400°C, a pressure in the interval 3-25 MPa, and a liquid hourly space velocity (LHSV) in the interval 0.5-8 hr 1 , optionally together with intermediate cooling by quenching with cold hydrogen, feed or product.
  • the pressure is preferably high, such as 10-25 MPa.
  • the composition of the hydroconversion catalyst actually allows for catalyzing hydrotreatment reactions as well, but it according to the present disclosure, it is preferred to separate the exothermal hydrotreatment reactions from the hydroconversion reactions, since too high temperatures in the presence of a hydroconversion catalyst may lead to undesired overcracking and other side reactions, sacrificing yield or catalyst lifetime.
  • an upstream hydrotreatment step with complete or close to complete hydrotreatment is commonly preferred.
  • the determination of the exact conditions will require experimental optimization, familiar to the skilled person, involving determination of the seventy (by combined optimization of temperature, space velocity, catalyst material and hydrogen pressure) where the boiling point is not substantially changed, while the specific gravity is decreased to the specified range.
  • T95 of the specification will commonly be 360°C and the specific gravity specification may be 0.81 to 0.96, such that the hydroconversion step (c) of the process receives a hydrotreated hydrocarbon stream having a T50 below 360°C and a specific gravity above 0.96, i.e. a stream which substantially fulfills the boiling point criteria of the diesel specification but not the specific gravity criteria.
  • T95 of the specification will commonly be 300°C and the specific gravity specification may be 0.78 to 0.82, such that the hydroconversion step (c) of the process receives a hydrotreated hydrocarbon stream having a T50 below 300°C and a specific gravity above 0.82, i.e. a stream which substantially fulfills the boiling point criteria of the diesel specification but not the specific gravity criteria.
  • the hydroconversion process will have a balanced seventy, converting a significant amount of aromatic, olefinic and cyclic bonds, without cracking a substantial amount of hydrocarbons to smaller molecules, which will reduce the specific gravity and increase the hydrogen content in ways which may not be obtained by hydrotreatment alone.
  • the commercial transportation fuel specification of relevance may mainly be for diesel and marine fuels, since jet and naphtha specifications may require other processes to be fulfilled.
  • a hydroconversion catalyst inherently also will have hydrotreatment activity, the nomenclature known to the skilled person is emphasized.
  • a hydrotreatment catalyst will not show significant hydroconversion activity and will not contain zeolites, molecular sieves or silica-alumina in catalytically active amounts and the carbon-carbon single-bonds are not affected by contact with a hydrotreatment catalyst. Nevertheless, the molecular structure may be changed during hydrotreatment, e.g. by releasing oxygen atoms defining the molecular structure.
  • hydroconversion catalyst relative to an hydroisomerization catalyst is also appropriate.
  • a hydroisomerization catalyst will inherently have a side reaction activity for hydroconversion.
  • the nature of hydroconversion will involve a consumption of hydrogen, due to the opening of rings and the breakage of hydrocarbons.
  • a catalytic process shall be considered a hydroisomerization process if at least 50% of the changes of hydrocarbonaceous molecules is made without net addition of hydrogen to the hydrocarbonaceous molecules, contrary to e.g. hydrotreatment replacing heteroatoms with hydrogen without significant modification of and saturating double bonds and aromatic structures or hydroconversion, breaking carbon-carbon bonds by insertion of hydrogen.
  • hydroconversion involves breaking of carbon-carbon bonds, and since the boiling point of shorter hydrocarbon molecules is lower than that of longer molecules, hydroconversion involves a loss of high boiling product to lower boiling product. While raw product boiling in the naphtha range (80-150°C), product boiling in the aviation range (150-290°C) and product boiling in the diesel range (150-390°C) may be of similar value, the cracking will involve a shortening of carbon molecules and thus a reduction of the mass of liquid product, with the related result of conversion of liquid transportation fuels to gaseous hydrocarbons of lower value, i.e. a loss of liquid transportation fuel yield. Therefore, hydrocracking of feedstock is carried out on fractions boiling above the desired product range, to minimize this yield loss.
  • the objective of hydroprocessing is traditional hydrocracking to reduce molecular weight and boiling point
  • the feedstock directed to the process is fractionated to contain a minimum boiling below the desired end point, to minimize loss of liquid product yield.
  • the objective is the conversion of cyclic molecules to branched molecules, with the related effect of shifting the aromatic to non-aromatic cyclic molecule equilibrium away from aromatic molecules, contrary to the objective of reducing molecular weight according to traditional hydrocracking, the stream directed to hydroconversion is instead having a boiling point distribution with a wide overlap with the desired product.
  • An amount of the stream may be boiling at higher temperatures, to compensate for the inevitable reduction of molecular weight, but to have a substantial conversion of cyclic molecules to non-cyclic molecules the stream for hydroconversion must include a fraction overlapping the desired product boiling point range.
  • the addition of hydrogen to the hydrocarbonaceous cyclic molecules has the further advantage of increasing the molecular weight and reducing the density, such that the volume is increased by two mechanisms.
  • the removal of cyclic molecules in naphtha typically decreases the octane number, and thus the value of the product, and therefore the naphtha fraction of the product may typically beneficially be removed from the middle distillate fraction prior to hydroconversion, in order to maximize the value and the volume of this naphtha fraction.
  • the naphtha fraction also has several possible applications, e.g.
  • a hydroprocessed stream comprising hydrocarbons, excess hydrogen and inorganic molecules comprising heteroatoms must be separated in hydrocarbons and molecules comprising heteroatoms, which - typically are gaseous.
  • the hydroprocessed stream is directed to a separation section, which for process scenarios relating to the treatment of pyrolysis oil typically either will be between a base metal based hydrotreatment reactor and a noble metal based hydroconversion reactor, or if the hydroconversion catalyst comprises base metals, downstream the hydroconversion reactor.
  • the process may also comprise one or more other conversion steps, such as hydroconversion or hydroisomerization, and depending on the sequence of these steps and the catalytically active metals used, the skilled person will be aware of the possible positions for introducing a separation section with the purpose of withdrawing a recycle gas stream.
  • conversion steps such as hydroconversion or hydroisomerization
  • the gas to oil ratio in the hydroprocessing reactors is also very high compared to other hydroprocessing processes, such as from 1000 to 7000 Nm 3 /m 3 .
  • This hydrogen gas may be used to control process temperatures, by stepwise injections of cooled gas.
  • the gas to oil ratio is selected from the hydrogen concentration in the treat gas and the expected consumption of hydrogen, as calculated from the molecular composition of the feedstock, including the average number of double bonds and aromatic bonds, heteroatoms and the expected breaking of carbon-carbon bonds, multiplied by a safety factor which may be from 2 to 10 times, dependent on the nature of the process, including the risk of process runaway.
  • the pyrolysis oil product streams may contain aromatic hydrocarbons, long linear hydrocarbons, gaseous hydrocarbons, water and to some extent carbon oxides.
  • nitrogen and chloride in the hydrocarbonaceous feedstock will result in ammonia and hydrogen chloride in the hydroprocessed stream; which may solidify as ammonium chloride.
  • Added sulfur as well as any sulfur in the pyrolysis oil will be present as hydrogen sulfide in the hydroprocessed stream, and finally an excess amount of hydrogen will pass unreacted to the hydroprocessed stream.
  • recycle may be used for different purposes; gas recycle for efficient use of hydrogen, liquid recycle around the hydroconversion catalyst to maximize the yield of the desired fraction and liquid recycle around the hydrotreatment catalyst to limit the temperature increase due to exothermal deoxygenation reactions as well as to limit the reaction rate of polymerization reactions for reactive oxygenates and other reactive compounds in the pyrolysis oil.
  • the choice of recycle configuration will be related to different benefits, including process simplicity by minimizing the number of recycle loops, minimizing reactor volume and cost by choosing configurations with low recycle volumes, maximizing process reactivity control by high recycle volume and/or extensive cooling, and minimizing polymerization by high recycle volume.
  • Process configurations without recycle may also be beneficial due to simplicity and low cost, especially in the cases where the process volume is moderate, or where an appropriate diluent is available.
  • FIG. 1 shows a process for conversion of solid material to transportation fuel.
  • a solid feedstock (2) such as end of life tires or ligneous waste (straw, wood or similar) is directed to a hydrothermal decomposition plant (PYP), which may be of several different types.
  • solids (4) such as char and carbon black, pyrolysis gas (6) and pyrolysis oil (8) are released from the hydrothermal decomposition plant (PYP), but not all fractions may be present.
  • the pyrolysis oil is only formed after cooling a vapor phase from the pyrolysis process.
  • water may also be condensed from the vapor phase.
  • a hydrotreatment process may also be carried out in which the pyrolysis vapor or the pyrolysis oil is contacted with hydrogen in the presence of a hydrotreatment catalyst, e.g. in a process where the catalyst is fluidized.
  • a step of hydrotreatment (HDT) is carried out in order to provide a hydrotreated intermediate after combination of a hydrogen rich stream (10) and the pyrolysis oil (8), in the presence of a hydrotreatment catalyst (HDT) comprising one or more metals typically sulfided base metals, but possibly noble metals, on a refractory support such as alumina.
  • this step is shown as a single fixed bed reactor (HDT), but the step may in practice involve multiple reactors, local recycle of intermediate product, splitting of the feed between multiple and other variations known e.g. from the treatment of renewable fats and oils and/or fossil feedstocks.
  • HDT fixed bed reactor
  • the hydrotreated intermediate (12) is directed to a first fractionation step (FRAC1 ), in which gas (14), naphtha (16), diesel (17) and high boiling hydrotreated hydrocarbons (18) are separated, and the deiesel (17) and the high boiling hydrotreated hydrocarbon (18) are combined with a recycle heavy product (20) and directed as a stream for hydroconversion (22) to further hydroprocessing in a hydroconversion reactor (HC), where it contacts a hydroconversion catalyst, comprising an active metal, which may either be a sulfided base metal or a noble metal, and an acidic support, such as a zeolite.
  • FRAC1 first fractionation step
  • gas (14), naphtha (16), diesel (17) and high boiling hydrotreated hydrocarbons (18) are separated, and the deiesel (17) and the high boiling hydrotreated hydrocarbon (18) are combined with a recycle heavy product (20) and directed as a stream for hydroconversion (22) to further hydroprocessing in a hydroconversion reactor (HC), where it contacts a hydroconversion catalyst
  • the hydroconversion produces a hydroconverted hydrocarbon stream (24), by saturating aromatics and breaking carbon-carbon bond to open hydrocarbon rings, with a side effect of reducing molecular weight by cleaving some molecules. Accordingly, the amount of cyclic compounds is reduced and the boiling point range of the hydroconverted hydrocarbon stream (24) is changed with a reduction of the amount of middle distillate, such as jet and diesel, and a provision of naphtha and fuel gases, which are separated in a second fractionation step (FRAC2), into gas (26), naphtha (28), diesel (30) and recycle heavy product (20).
  • FRAC2 second fractionation step
  • the naphtha produced during hydroconversion (28) will be paraffinic and thus have a lower octane number, and may therefore be preferred to be directed to a hydrogen plant, to provide the hydrogen for the process. Since the high boiling hydrotreated hydrocarbons (18) were fractionated to include an amount boiling above the middle distillate boiling range, an amount of such heavy product is likely to be present for recycle to the inlet of the hydroconversion reactor.
  • Fig.1 was made to illustrate the principles of the process, and for simplicity details have been omitted, including heat exchangers, the gas loop and phase separators.
  • the entire hydrotreated intermediate (12) may in combination with the recycle heavy product (20) be directed as the stream for hydroconversion (24).
  • a first aspect of the present disclosure relates to a process for production of a hydrocarbon composition useful as a transportation fuel according to a commercial transportation fuel specification from a hydrocarbonaceous feedstock comprising at least 0.5 wt% oxygen and at least 25 wt% carbon in cyclic structures, comprising the steps of a. directing a hydrocarbonaceous feedstock to hydrotreatment in one or more steps providing an intermediate product comprising less than 0.1 wt% oxygen and a specific gravity, for the fraction boiling in the range defined by the commercial transportation fuel specification, above the upper limit of specific gravity under the commercial transportation fuel specification, b.
  • fractionating said hydroconverted hydrocarbon stream further provides at least a fraction boiling above T95 of the commercial transportation fuel fuel specification, which is directed as recycle to be combined with said hydrotreated hydrocarbon stream for hydroconversion.
  • a third aspect of the process according to the first or second aspects, wherein the hydroconversion conditions involves a pressure above 15 MPa and below 25 MPa.
  • a fourth aspect of the process according to any aspect above, wherein the hydroconversion conditions involves a temperature above 350°C and below 420°C.
  • the hydroconversion catalyst comprises an active metal, either one or more elemental noble metals such as platinum and/or palladium or one or more sulfided base metals such as nickel, cobalt, tungsten or molybdenum, an acidic support, such as a molecular sieve showing high activity in breaking carboncarbon bonds, and having a topology such as MFI, BEA and FAU or amorphous silica-alumina and optionally a refractory support such as alumina, silica or titania, or combinations thereof.
  • an active metal either one or more elemental noble metals such as platinum and/or palladium or one or more sulfided base metals such as nickel, cobalt, tungsten or molybdenum
  • an acidic support such as a molecular sieve showing high activity in breaking carboncarbon bonds, and having a topology such as MFI, BEA and FAU or amorphous silica-alumina and optionally a refractory support such as
  • An eighth aspect of the process according to any aspect above, wherein the provision of a hydrotreated hydrocarbon stream for hydroconversion from said intermediate product by fractionation involves separating said intermediate product into a fraction boiling in the naphtha range and a fraction boiling above the naphtha range.
  • thermochemical decomposition process This has the associated benefit of enabling upgrading of such a hydrocarbonaceous feedstock from a thermochemical decomposition process, which may be especially useful if it comprises high amounts of cyclic structures from the material directed to the thermochemical decomposition process, as would be the case from end of life tires and capitaous materials.
  • An additional aspect of the invention relates to a process plant for production of a hydrocarbon by a process according to any aspect above.
  • a process illustrating Figure 1 is evaluated with basis in experiments, in combination with evaluations of process simulations.
  • Case 1 illustrated in Table 1 represents the process layout according to Figure 1 , but taking out heavy product 20 instead of recycling it, for simplicity.
  • a pyrolysis oil originating from pyrolysis of end of life tires (stream 8) is hydrotreated, separated in naphtha and a higher boiling fraction and directed to contact a hydroconversion catalyst under conditions resulting in a diesel product comprising a low amount of aromatics and a specific gravity value in compliance with EN590 requirements (0.8391 vs. the specified 0.845).
  • the seventy of the conditions is illustrated by the conversion of the fraction boiling above 390°C, of which 73.5 wt% is converted to lower boiling product.
  • Stream 16 is a fraction of aromatic naphtha corresponding to 15 wt%FF (wt% on fresh feed basis).
  • 16 wt%FF naphtha with 8.3 wt% aromatics is produced in stream 28, and in stream 30 62 wt%FF diesel with 4.0 wt% aromatics is produced.
  • 6.1 wt%FF is available as unconverted oil, which could be directed as recycle.
  • Case 2 illustrated in Table 2 similarly represents a variant of the process layout according to Figure 1 in which all of the hydrotreated product 12 is directed to hydrocracking.
  • the seventy of the conditions is illustrated by the conversion of the fraction boiling above 390°C. In this case 56.5 wt% is converted to lower boiling product.
  • the experiments were carried out with only the liquid fraction of the hydrotreated product 12 being directed to hydrocracking.
  • case 3 illustrated in Table 3 represents a situation where the intermediate fractionation provides naphtha and diesel and hydroconversion is operated as hydrocracking in order to maximize liquid yields.
  • This case shows a total of 76.5 wt% diesel and 18.1 wt% naphtha, which is slightly higher combined yield of product boiling in the diesel and naphtha ranges compared to case 1 or 2, but the 62 wt% FF diesel product does not fulfill specific gravity specifications, and will therefore introduce limitations on use, even in blends.
  • case 2 the amount and quality of the diesel fraction is above that of case 1 , but only a single naphtha fraction is provided.
  • the naphtha has a low content of aromatics, and the quantity is below that of case 1 .

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Abstract

La présente divulgation concerne un procédé et une installation de traitement pour la production d'une composition hydrocarbonée utile en tant que carburant de transport selon une spécification de carburant de transport commercial à partir d'une charge hydrocarbonée comprenant au moins 0,5 % en poids d'oxygène et au moins 25 % en poids de carbone dans des structures cycliques, comprenant les étapes consistant à : a. acheminer une charge hydrocarbonée vers un hydrotraitement en une ou plusieurs étapes ce qui permet d'obtenir un produit intermédiaire comprenant moins de 0,1 % en poids d'oxygène et une gravité spécifique, pour la fraction dont le point d'ébullition se situe dans la plage définie par la spécification de carburant de transport commercial, au-dessus de la limite supérieure de gravité spécifique dans la spécification de carburant de transport commercial, b. fournir un flux d'hydrocarbure hydrotraité pour l'hydroconversion à partir dudit produit intermédiaire éventuellement par fractionnement, dans lequel ladite fraction pour l'hydroconversion a un T50 inférieur à T95 de la spécification du carburant de transport commercial, c. acheminer le flux d'hydroconversion pour qu'il entre en contact avec un catalyseur d'hydroconversion dans des conditions d'hydroconversion pour obtenir un flux d'hydrocarbure hydroconverti, d. fractionner ledit flux d'hydrocarbure hydroconverti pour obtenir au moins ladite composition d'hydrocarbure utile comme carburant de transport.
PCT/EP2023/058325 2022-03-31 2023-03-30 Procédé de production de carburant de transport WO2023187072A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090287029A1 (en) * 2008-03-17 2009-11-19 Amarendra Anumakonda Controlling Production of Transportation Fuels from Renewable Feedstocks
US20120151828A1 (en) * 2010-12-15 2012-06-21 Uop Llc Hydroprocessing of fats, oils, and waxes to produce low carbon footprint distillate fuels
US20210395620A1 (en) * 2018-10-24 2021-12-23 Haldor Topsøe A/S Method for production of aviation fuel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090287029A1 (en) * 2008-03-17 2009-11-19 Amarendra Anumakonda Controlling Production of Transportation Fuels from Renewable Feedstocks
US20120151828A1 (en) * 2010-12-15 2012-06-21 Uop Llc Hydroprocessing of fats, oils, and waxes to produce low carbon footprint distillate fuels
US20210395620A1 (en) * 2018-10-24 2021-12-23 Haldor Topsøe A/S Method for production of aviation fuel

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