US20150136659A1 - Hydroprocess for a hydrocarbon stream from coal tar - Google Patents

Hydroprocess for a hydrocarbon stream from coal tar Download PDF

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Publication number
US20150136659A1
US20150136659A1 US14/469,318 US201414469318A US2015136659A1 US 20150136659 A1 US20150136659 A1 US 20150136659A1 US 201414469318 A US201414469318 A US 201414469318A US 2015136659 A1 US2015136659 A1 US 2015136659A1
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Prior art keywords
catalyst
stream
hydrocarbon
product
coal tar
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Abandoned
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US14/469,318
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English (en)
Inventor
Paul T. Barger
Maureen L. Bricker
Joseph A. Kocal
Matthew Lippmann
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Honeywell UOP LLC
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UOP LLC
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Priority to US14/469,318 priority Critical patent/US20150136659A1/en
Assigned to UOP LLC reassignment UOP LLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BRICKER, MAUREEN L., LIPPMANN, Matthew, BARGER, PAUL T., KOCAL, JOSEPH A.
Publication of US20150136659A1 publication Critical patent/US20150136659A1/en
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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
    • 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
    • C10G47/18—Crystalline alumino-silicate carriers the catalyst containing platinum group metals or compounds thereof
    • 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
    • C10G1/04—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by extraction
    • C10G1/045—Separation of insoluble 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
    • 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
    • C10G65/10—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only cracking 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
    • 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
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only

Definitions

  • Coke Pyrolysis of coal produces coke and coal tar.
  • the coke-making or “coking” process consists of heating the material in closed vessels in the absence of oxygen to very high temperatures.
  • Coke is a porous but hard residue that is mostly carbon and inorganic ash, which is used in making steel.
  • Coal tar is the volatile material that is driven off during heating, and it comprises a mixture of a number of hydrocarbon compounds. It can be separated to yield a variety of organic compounds, such as benzene, toluene, xylene, naphthalene, anthracene, and phenanthrene. These organic compounds can be used to make numerous products, for example, dyes, drugs, explosives, flavorings, perfumes, preservatives, synthetic resins, and paints and stains. The residual pitch left from the separation is used for paving, roofing, waterproofing, and insulation.
  • Coal tar hydrocarbon streams especially heavier hydrocarbon streams and pitch, can be difficult to crack in hydroprocessing, resulting in an undesirable ratio of pitch to more valuable volatile products.
  • One aspect of the invention involves a coal tar process.
  • a coal tar stream is provided, and the coal tar stream is separated to provide a plurality of hydrocarbon streams.
  • At least one of the hydrocarbon streams is hydroprocessed in a fluidized bed hydroprocessing zone with a catalyst to provide a gaseous volatile product and a solid heavy hydrocarbon product absorbed onto the catalyst.
  • the gaseous volatile product is separated from the catalyst.
  • the catalyst is regenerated by separating the absorbed heavy hydrocarbon product from the catalyst. The regenerated catalyst is recycled into the hydroprocessing zone.
  • a coal feed is pyrolyzed to provide a coal tar stream and a coke stream.
  • the coal tar stream is separated to provide a plurality of hydrocarbon streams.
  • At least one of the hydrocarbon streams is hydroprocessed in a fluidized bed hydroprocessing zone with a catalyst to provide a gaseous volatile product and a solid heavy hydrocarbon product absorbed onto the catalyst.
  • the gaseous volatile product is separated from the catalyst, and the catalyst is regenerated by separating the absorbed heavy hydrocarbon product from the catalyst.
  • the regenerated catalyst is recycled into the hydroprocessing zone.
  • a hydrocarbon stream from a coal tar stream is hydroprocessed in a fluidized bed hydroprocessing zone with a catalyst to provide a gaseous volatile product and a solid heavy hydrocarbon product absorbed onto the catalyst.
  • the gaseous volatile product is separated from the catalyst, and the catalyst is regenerated by separating the absorbed heavy hydrocarbon product from the catalyst.
  • the regenerated catalyst is recycled into the hydroprocessing zone.
  • the Figure is an illustration of one embodiment of the process of the present invention.
  • a coal feed 10 can be sent to a pyrolysis zone 15 for pyrolyzing.
  • a portion of the coal feed 10 is sent to a gasification zone (not shown), for instance the coal feed 10 can be split into two parts and sent to both.
  • syngas which is a mixture of carbon monoxide and hydrogen.
  • the syngas can be further processed using the Fischer-Tropsch reaction to produce gasoline or using the water-gas shift reaction to produce more hydrogen.
  • the coal is heated at high temperature, e.g., up to about 2,000° C. (3600° F.), in the absence of oxygen to drive off the volatile components. Coking produces a coke stream 20 and a coal tar stream 25 .
  • the coke stream 20 can be used in other processes, such as the manufacture of steel.
  • the coal tar stream 25 is sent to a fractionation zone 30 for separation.
  • Coal tar comprises a complex mixture of heterocyclic aromatic compounds and their derivatives with a wide range of boiling points.
  • the number of fractions and the components in the various fractions can be varied as is well known in the art.
  • a typical separation process involves separating the coal tar stream 25 into four to six streams.
  • the light oil fraction contains compounds such as benzenes, toluenes, xylenes, naphtha, coumarone-indene, dicyclopentadiene, pyridine, and picolines.
  • the middle oil fraction contains compounds such as phenols, cresols and cresylic acids, xylenols, naphthalene, high boiling tar acids, and high boiling tar bases.
  • the heavy oil fraction contains creosotes, for example.
  • the anthracene oil fraction contains anthracene.
  • Pitch is the residue of the coal tar distillation containing primarily aromatic hydrocarbons and heterocyclic compounds.
  • the fractionation zone 30 separates the coal tar stream into a fraction comprising NH 3 , CO, and light hydrocarbons 35 , light and middle oil fractions 40 , 45 , and at least one heavy oil fraction 50 having a minimum boiling point of about 450° C. to about 500° C.
  • the heavy fraction 50 is introduced to a fluidized bed hydroprocessing zone 60 , with hydrogen co-feed streams 57 and 58 including fresh hydrogen stream 56 and recycle stream 82 , for hydroprocessing, e.g., hydrocracking, the heavy fraction 50 .
  • the hydrocarbon stream that is input to the fluidized bed hydroprocessing zone 60 can come from other sources.
  • the pitch stream 55 can be input to the hydroprocessing zone 60 .
  • the fractionation zone 30 is replaced with a solvent extractor (not shown), which extracts a coal tar stream with a solvent such as toluene, hexane, tetrahydrofuran, or combinations thereof
  • the solvent extractor outputs a toluene-insoluble stream, a hexane-insoluble stream, a tetrahydrofuran stream, or a combination. This output can be introduced to the hydroprocessing zone 60 .
  • a heavy end coal tar stream taken directly from the pyrolysis zone 15 is input to the hydroprocessing zone without intermediate separation such as fractionation or solvent extraction.
  • the coal tar stream can be obtained from sources other than pyrolyzing the coal feed 10 in the pyrolysis zone 15 , and this coal tar stream can either be separated and fed to the hydroprocessing zone 60 , or a heavy feed coal tar stream can be directly input into the hydroprocessing zone.
  • Hydrocracking is a process in which hydrocarbons crack in the presence of hydrogen to lower molecular weight hydrocarbons.
  • Typical hydrocracking conditions may include a temperature of about 290° C. (550° F.) to about 468° C. (875° F.), a pressure of about 3.5 MPa (500 psig) to about 20.7 MPa (3000 psig), a liquid hourly space velocity (LHSV) of about 1.0 to less than about 2.5 hr ⁇ 1 , and a hydrogen rate of about 421 to about 2,527 Nm 3 /m 3 oil (2,500-15,000 scf/bbl).
  • Typical hydrocracking catalysts include amorphous silica-alumina bases or low-level zeolite bases combined with one or more Group VIII or Group VIB metal hydrogenating components, or a crystalline zeolite cracking base upon which is deposited a Group VIII metal hydrogenating component. Additional hydrogenating components may be selected from Group VIB for incorporation with the zeolite base.
  • the example fluidized bed hydroprocessing zone 60 includes a plurality of zones for hydrocracking the hydrocarbon stream, e.g., heavy oil fraction 50 .
  • An outer, reaction zone 65 includes a fluidized bed having an active hydrocracking catalyst disposed therein.
  • the catalyst preferably is powdered.
  • Example active hydrocracking catalysts include non-noble metals. Preferred catalysts include Ni—Mo and W—Mo.
  • the catalyst preferably is on a spray-dried alumina or silica-aluminum base.
  • the catalyst is circulated internally through the hydroprocessing zone 60 .
  • An example fluidized bed hydroprocessing zone 60 includes one or more internal riser reactors 70 contained within an outer fluidized reactor 65 .
  • the heavy fraction 50 and hydrogen co-feed stream 57 are mixed to provide a combined hydrocarbon and hydrogen stream 59 which is divided and injected into the bottom of each of the internal riser reactors 70 with sufficient velocity to lift a portion of the catalyst within the fluidized bed 65 through the internal riser to thoroughly mix the hydrocarbon, hydrogen and catalyst and initiate the hydroprocessing reactions.
  • the second hydrogen co-feed stream 58 is fed through a distributor to the bottom of the fluidized bed 65 to provide fluidization. At the top of the riser reactors 70 the majority of the catalyst and any adsorbed or liquid-phase hydrocarbon drop down into the fluidized bed 65 for further hydroprocessing.
  • hydrocracking hydrogen is provided at a very high pressure, e.g., an H 2 partial pressure ranging from about 3.4 MPa (500 psig) to about 17.2 MPa (2500 psig).
  • An example temperature range is between about 350° C. to about 600° C.
  • a gaseous volatile product is produced, as well as a solid heavy hydrocarbon product (e.g., pitch) that is absorbed on the catalyst.
  • a feed rate and withdrawal rate of the hydrocarbon stream into and out of the hydroprocessing zone 60 can be controlled in relation to reaction activity to reduce the buildup of heavy material (i.e., the amount of absorbed pitch) on the catalyst. This limits buildup of solids on the catalyst and preferably keeps the catalyst in a powder form.
  • a portion of the circulated catalyst with the adsorbed pitch is removed as a free-flowing solid 95 from the fluidized bed 65 .
  • the disengaging zone 75 separates the gas and solid phase by the use of one or more stages of cyclone separators operating at about reactor temperature and pressure.
  • the separated gaseous volatile product 80 is removed as an output of the disengaging zone 75 from the top of the hydroprocessing zone 60 .
  • the separated gaseous volatile product 80 cooled in a condenser 81 to give a gas-phase product stream 82 consisting primarily of unreacted hydrogen and a liquid-phase condensed hydrocarbon stream.
  • a portion of the gas-phase product can be recycled back to the hydroprocessing reactor via lines 57 and 58 , while the remainder is recovered as a vapor product 84 .
  • the condensed hydrocarbon stream 83 can be processed in a processing zone 85 to provide one or more products 90 .
  • the separated catalyst 95 is then fed to a regeneration zone 100 for separating the absorbed heavy hydrocarbon product from the catalyst.
  • the regeneration zone 100 preferably is a separate vessel from the hydroprocessing zone 60 .
  • the absorbed heavy hydrocarbon product is burned off from the catalyst.
  • the absorbed heavy hydrocarbon product can be burned at high temperatures, e.g., 450-800° C., with an air input 97 .
  • the separated catalyst 95 can be regenerated by an extraction process such as solvent extraction using a solvent such as paraffins, aromatics, sulfolane, and other polar aprotic organic solvents at 100-250° C., a solvent to catalyst weight ratio of 1:1 to 100:1 and sufficient pressure to maintain the solvent in the liquid phase at the extraction temperature.
  • solvent such as paraffins, aromatics, sulfolane, and other polar aprotic organic solvents
  • the burned off or otherwise separated heavy hydrocarbon product is output via stream 105 .
  • the regenerated, solid catalyst 110 is circulated to the fluidized bed 65 .
  • Example processes for the condensed hydrocarbon stream 83 in the processing zone include hydrotreating, hydrocracking, deoxygenation, desulfurization, and hydrogenation.
  • Hydrotreating is a process in which hydrogen gas is contacted with a hydrocarbon stream in the presence of suitable catalysts which are primarily active for the removal of heteroatoms, such as sulfur, nitrogen, and metals from the hydrocarbon feedstock.
  • suitable catalysts which are primarily active for the removal of heteroatoms, such as sulfur, nitrogen, and metals from the hydrocarbon feedstock.
  • hydrocarbons with double and triple bonds may be saturated.
  • Aromatics may also be saturated.
  • Typical hydrotreating reaction conditions include a temperature of about 290° C. (550° F.) to about 455° C.
  • Typical hydrotreating catalysts include at least one Group VIII metal, preferably iron, cobalt and nickel, and at least one Group VI metal, preferably molybdenum and tungsten, on a high surface area support material, preferably alumina.
  • Other typical hydrotreating catalysts include zeolitic catalysts, as well as noble metal catalysts where the noble metal is selected from palladium and platinum.
  • Hydrocracking is a process in which hydrocarbons crack in the presence of hydrogen to lower molecular weight hydrocarbons.
  • Typical hydrocracking conditions may include a temperature of about 290° C. (550° F.) to about 468° C. (875° F.), a pressure of about 3.5 MPa (500 psig) to about 20.7 MPa (3000 psig), a liquid hourly space velocity (LHSV) of about 1.0 to less than about 2.5 hr ⁇ 1 , and a hydrogen rate of about 421 to about 2,527 Nm 3 /m 3 oil (2,500-15,000 scfibbl).
  • Typical hydrocracking catalysts include amorphous silica-alumina bases or low-level zeolite bases combined with one or more Group VIII or Group VIB metal hydrogenating components, or a crystalline zeolite cracking base upon which is deposited a Group VIII metal hydrogenating component. Additional hydrogenating components may be selected from Group VIB for incorporation with the zeolite base.
  • Deoxygenation is a process for removing oxygen from a molecule.
  • An example deoxygenation process hydroprocesses a feed by passing the feed to a hydrotreating unit where the feed is contacted with a hydrotreating catalyst.
  • the hydrotreating unit can also be a hydrocracking unit with a hydrocracking catalyst.
  • Hydrogenation and hydrotreating catalysts are also capable of catalyzing decarboxylation, decarbonylation, and/or hydrodeoxygenation of the feed to remove oxygen.
  • Deoxygenation conditions include a relatively low pressure of about 1724 kPa absolute (250 psia) to about 10.342 kPa absolute (1500 psia), with embodiments in the range of 3447 kPa (500 psia) to about 6895 kPa (1000 psia) or below 4826 kPa (700 psia); a temperature of about 200° C. to about 460° C. with embodiments in the range of about 288° C. to about 345° C.; and a liquid hourly space velocity (LHSV) of about 0.25 to about 4 hr ⁇ 1 with example embodiments in the range of about 1 to about 4 hr ⁇ 1 .
  • LHSV liquid hourly space velocity
  • Desulfurization is a process for reducing sulfur of hydrocarbon feedstocks to lower levels. Desulfurization is typically performed by contacting a hydrocarbon feedstock in a desulfurization reaction vessel or zone with a suitable desulfurization catalyst under conditions of elevated temperature and pressure in the presence of hydrogen to yield a product containing the desired maximum limits of sulfur.
  • An example hydrocarbon desulfurization process is disclosed in U.S. Pat. No. 7,108,779.
  • Suitable desulfurization catalysts include hydrotreating catalysts and include those which are comprised of at least one Group VIII metal, preferably iron, cobalt and nickel, more preferably cobalt and/or nickel and at least one Group VI metal, preferably molybdenum and tungsten, on a high surface area support material, preferably alumina.
  • Other suitable desulfurization catalysts include zeolitic catalysts, as well as noble metal catalysts where the noble metal is selected from palladium and platinum. More than one type of desulfurization catalyst can be used in the same reaction vessel.
  • the Group VIII metal is typically present in an amount ranging from about 2 to about 20 weight percent, preferably from about 4 to about 12 weight percent.
  • the Group VI metal will typically be present in an amount ranging from about 1 to about 25 weight percent, preferably from about 2 to about 25 weight percent.
  • Typical desulfurization temperatures range from about 204° C. (400° F.) to about 482° C. (900° F.) with pressures from about 2.1 MPa (300 psig) to about 17.3 MPa (2500 psig), preferably from about 2.1 MPa (300 psig) to about 13.9 MPa (2000 psig).
  • Operating conditions and desulfurization catalysts within the desulfurization reactor can be selected to affect the quality of the desulfurized products.
  • Hydrogenation involves the addition of hydrogen to hydrogenatable hydrocarbon compounds.
  • hydrogen can be provided in a hydrogen-containing compound with ready available hydrogen, such as tetralin, alcohols, hydrogenated naphthalenes, and others via a transfer hydrogenation process with or without a catalyst.
  • the hydrogenatable hydrocarbon compounds are introduced into a hydrogenation zone and contacted with a hydrogen-rich gaseous phase and a hydrogenation catalyst in order to hydrogenate at least a portion of the hydrogenatable hydrocarbon compounds.
  • the catalytic hydrogenation zone may contain a fixed, ebulated or fluidized catalyst bed.
  • This reaction zone is typically at a pressure from about 689 kPa gauge (100 psig) to about 13790 kPa gauge (2000 psig) with a maximum catalyst bed temperature in the range of about 177° C. (350° F.) to about 454° C. (850° F.).
  • the liquid hourly space velocity is typically in the range from about 0.2 hr ⁇ 1 to about 10 hr ⁇ 1 and hydrogen circulation rates from about 200 standard cubic feet per barrel (SCFB) (35.6 m 3 /m 3 ) to about 10,000 SCFB (1778 m 3 /m 3 ).

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
US14/469,318 2013-11-19 2014-08-26 Hydroprocess for a hydrocarbon stream from coal tar Abandoned US20150136659A1 (en)

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WO2019055529A1 (en) * 2017-09-13 2019-03-21 University Of Wyoming SYSTEMS AND METHODS FOR COAL REFINING CONVERSION TO HIGH-VALUE PRODUCTS

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CN107955638B (zh) * 2016-10-14 2019-12-24 北京华石联合能源科技发展有限公司 一种煤焦油的预处理方法及其装置
US10978718B2 (en) 2017-08-29 2021-04-13 Uchicago Argonne, Llc Carbon dioxide reduction electro catalysts prepared for metal organic frameworks
US11033888B2 (en) 2017-08-30 2021-06-15 Uchicago Argonne, Llc Nanofiber electrocatalyst
US11633722B2 (en) 2020-09-30 2023-04-25 Uchicago Argonne, Llc Catalyst for water splitting

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Publication number Priority date Publication date Assignee Title
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