US3494859A - Two-stage hydrogenation of an aromatic hydrocarbon feedstock containing diolefins,monoolefins and sulfur compounds - Google Patents

Two-stage hydrogenation of an aromatic hydrocarbon feedstock containing diolefins,monoolefins and sulfur compounds Download PDF

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US3494859A
US3494859A US644337A US3494859DA US3494859A US 3494859 A US3494859 A US 3494859A US 644337 A US644337 A US 644337A US 3494859D A US3494859D A US 3494859DA US 3494859 A US3494859 A US 3494859A
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hydrogen
reaction zone
hydrocarbons
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stream
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Robin J Parker
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Universal Oil Products Co
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Universal Oil Products Co
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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
    • 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
    • C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
    • C10G65/06—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps at least one step being a selective hydrogenation of the diolefins

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  • the efiluent is separated and an aromatic hydrocarbon is then hydrogenated at a relatively high temperature of 550750 F. with a conventional desulfurization catalyst to saturate olefins and convert sulfur compounds to hydrogen sulfide.
  • Hydrocarbons suitable for gasoline blending and aromatic hydrocarbons suitable for, say, solvent extraction are recovered as separate product streams. The method finds particular utility in stabilizing pyrolysis gasoline.
  • This invention relates to the hydrogenation of hydrocarbons. It particularly relates to the stabilization of pyrolysis gasoline. If specifically relates to a method for selectively removing diolefins and olefins from the product gasoline obtained in light olefin manufacture.
  • the efiiuent from the cracking zone may comprise light olefinic hydrocarbons such as ethylene, propylene, butylene, etc. or mixtures thereof, all of which may constitute the principal product or products.
  • light olefinic hydrocarbons such as ethylene, propylene, butylene, etc. or mixtures thereof, all of which may constitute the principal product or products.
  • pyrolysis gasoline which contains undesirable quantities of diolefin hydrocarbons and/ or sulfur compounds.
  • the pyrolysis gasoline frequently is rich in aromatic hydrocarbons, but it has been found that usually the aromatic portion of the pyrolysis gasoline is also heavily contaminated with olefin hydrocarbons which renders recovery of the aromatics in high purity extremely difficult.
  • a pyrolysis unit may charge ethane, propane, or a straight-run naphtha fraction containing about 5% aromatic hydrocarbons, to a pyrolysis unit.
  • the pyrolysis effluent is separated into desired fractions, one fraction of which usually comprises a C 400 F.
  • pyrolysis gasoline which represents, for example, approximately 1% to 40% by weight of the original naphtha feed depending upon the charge stock and severity of cracking. Since the pyrolysis gasoline is heavily contaminated, as previously mentioned, it is hydrotreated for saturation of olefin and/or diolefin compounds and for re- 3,494,859 Patented Feb. 10, 1970 ICC moval of sulfur compounds.
  • the prior art schemes also charge the hydrotreated pyrolysis gasoline fraction to an aromatic extraction unit for recovery of the aromatic hydrocarbons such as benzene, toluene, and xylene therefrom.
  • aromatic hydrocarbons such as benzene, toluene, and xylene therefrom.
  • Typical extraction procedures utilizing a solvent such as sulfolane or the glycols are well known to those skilled in the art for aromatic extraction purposes.
  • the diene content of such pyrolysis gasoline is usually within the range from 20 to 70 for C 400 F. gasolines.
  • the diolefin compounds pose particular difliculty in the operation of the hydrotreating facilities since these compounds cause extensive equipment fouling and catalyst bed fouling. So far as is known, the prior art hydrotreating process will experience this fouling from polymer formation to some extent. Usually, the prior art will attempt to improve the on-stream efficiency of the hydrotreating unit by either promoting the polymerization reaction prior to the hydrotreating step thereby preventing the polymer from reaching downstream equipment and/or utilizing operating techniques and schemes which tend to minimize polymer formation. None of the prior art approaches are completely successful in overcoming the fouling difficulty resulting from the diolefin compounds present in the pyrolysis gasoline.
  • the prior art schemes do not provide selectivity in the hydrotreating unit.
  • the hydrogenation reaction may not stop with the conversion of diolefins to olefins but will frequently saturate the amount of olefins completely and even hydrogenate substantial portions of aromatic hydrocarbons.
  • Such non-selectivity results in a decreased yield of desirable products in the pyrolysis gasoline.
  • aromatic hydrocarbons may not be hydrogenated, more frequently, olefin hydrocarbons are completely saturated, thereby significantly decreasing the octane blending value of that portion of the pyrolysis gasoline which is normally utilized in motor fuel.
  • the practice of the present invention provides a method for hydrogenating hydrocarbons which comprises admixing an aromatic hydrocarbon feedstock containing diolefin and olefin compounds, boiling within the range from C to 400 F., with hydrogen and a hereinafter specified recycle stream; passing said admixture into a first reaction zone maintained under hydrogenating conditions including relatively low temperature and the presence of a palladium-containing catalyst suflicient to convert diolefin compounds to olefin compounds without substantial saturation of olefin compounds; separating the total eflluent from said first reaction zone into a first gaseous fraction comprising hydrogen and a liquid fraction; returning a portion of said liquid fraction to the first re action zone as the specified recycle stream; passing the remainder of said liquid fraction into a separation zone maintained under conditions sufficient to produce an aro matic hydrocarbon concentrate stream and hydrocarbons suitable for gasoline blending; admixing said concentrate stream with at least a portion of said first gaseous fraction; passing the gaseous fraction-concentrate stream into a
  • Another broad embodiment of the invention includes the method hereinabove wherein said liquid fraction is separated into a relatively light liquid fraction and a relatively heavy liquid fraction and wherein said relatively light liquid fraction is recycled to said first reaction zone as specified in an amount such that the combined hydrocarbon charge to the first reaction zone has a diene value substantially less than that of said aromatic hydrocarbon feedstock.
  • the selectivity of the present invention is based on the discovery that the unique two-stage system for hydrogenation accomplishes the desired results of removing diolefins, selectively removing olefins, and removing sulfur compounds simultaneously from various fractions of pyrolysis gasoline so that maximum recovery of desired products may be obtained from the pyrolysis of ethane, propane and/or naphthas to produce, for example, ethylene.
  • This invention achieves these results in an economical and facile manner.
  • the use of the palladium catalyst and a relatively low temperature in the first reaction zone achieves selectively the conversion of diolefins to olefins without either substantial desulfurization or substantial saturation of the olefins.
  • the relatively low temperature is that which is below desulfurization temperatures for the same system.
  • satisfactory operating conditions for the first reaction zone include a temperature from 200 F. to 500 F., a pressure from 100 p.s.i.g. to 1200 p.s.i.g., a liquid hourly space velocity from 1 to 10, based on combined charge, and a molar excess of hydrogen typically within the range from 500 to 2,000 standard cubic feet of hydrogen per barrel of combined charge.
  • the operation performed in the second reaction zone of the present invention is primarily one of desulfurization and saturation of olefins boiling within the C to C boiling range, utilizing any of the well known desulfurization catalysts. It was found that the conventional nickel-containing desulfurization catalyst was particularly satisfactory in removing sulfur from the C to C aromatic concentrate fraction while simultaneously saturating any olefin compounds therein. By proper selection of operating conditions it was found that no substantial saturation of the aromatic hydrocarbons was achieved. Particularly satisfactory operating conditions for the second reaction zone of the present invention include a relatively high temperature in the range from 550 F. to 750 F., a pressure from 400 p.s.i.g.
  • a particularly useful catalyst for desulfurization and olefin saturation in the second reaction zone is, for example, nickel-molybdate supported on alumina.
  • a portion of the liquid efiluent from the first reaction zone is recycled in admixture with the feed to the first reaction zone to produce a combined charge to the reactor.
  • the purpose of this admixing is to reduce the diene value of the total feed to the reaction zone to a relatively low figure.
  • the diene value of the combined charge to the first reaction zone is less than and, typically, will be less than 20, e.g. from 10 to 15. It has been found that the pyrolysis gasoline contains, for example, 5% to by weight conjugated diolefin hydrocarbons, generally concentrated in the C fraction.
  • diolefins would contribute significantly to polymer formation in the reactor; however, utilizing the operating conditions previously mentioned and the satisfactory palladium catalyst, the diolefins are selectively converted to olefins at a temperature from 200 F. to 500 F., preferably from about 360 F. to 500 F.
  • the entire fresh hydrogen is added to the system only through the first reaction zone.
  • the sole source of hydrogen for the second reaction zone is obtained from the first zone. That is not to say, however, that there is not a recycle stream set-up around the second reactor.
  • the amount of hydrogen necessary to makeup for the hydrogen consumed in the second reactor comes only from the first reaction zone by way of cascade. By operating in this manner an important benefit is obtained.
  • the hydrogen to the first reaction Zone is substantially free of hydrogen sulfide; therefore, there is virtually no chance of forming mercaptans from hydrogen sulfide passing over the palladium catalyst of the first reaction zone.
  • the desulfurization catalyst in the second reaction zone is notably sulfur resistant. Therefore, the recycle hydrogen stream to the second reactor contains hydrogen sulfide with substantially no adverse effects being noticed on the desired reactions.
  • the present invention is based on the discovery that the palladium-containing catalyst is particularly useful in effectuating the desired reactions in the first reaction zone. Contlary to teachings found in the prior art, a platinum-containing catalyst was not satisfactory in the practice of the present invention. It was also distinctly discovered that palladium deposited on lithiated alumina support produced excellent results. The amount of lithium on the support achieved remarkable results in reducing gum formation caused by polymerization of the dienes on the acid sites of the catalyst.
  • the preferred palladium-containing catalyst employed in the present invention is prepared utilizing spherical alumina particles formed in accordance with the well known oil drop method as described in US. Patent No. 2,620,314, issued to James Hoekstra. These preferred catalysts contain either 0.75% or 0.375% by weight of palladium incorporated by way of an impregnation technique using the proper quantities of dinitro-dianisole palladium. Following evaporation to visual dryness and drying in air for about an hour at F. the palladium impregnated alumina is calcined at about 1100 F. for about two hours.
  • the lithium component is then incorporated using the necessary quantities of lithium nitrate to produce catalysts of 0.33% and 0.5% lithium in an impregnation procedure and the composite again is dried and calcined.
  • a distinctly preferred diene catalyst includes 04% by weight palladium, 0.5 by weight lithium on a inch spherical base.
  • the particularly preferred catalyst for the first reaction zone of the present invention comprises lithiated alumina containing from about 0.05% to about 5.0% by weight of palladium.
  • aromatic hydrocarbon feedstock obtained from the pyrolysis of hydrocarbons such as naphthas for the production of light olefinic gases such as ethylene.
  • aromatic hydrocarbon feedstock is intended to include those feedstocks containing sufficient quantities of aromatic hydrocarbons to warrant the desirability of. recovering these aromatic hydrocarbons as a separate product stream substantially free of olefin hydrocarbons and sulfur compounds.
  • the pyrolysis reaction for the conversion of hydrocarbons into normally gaseous olefinic hydrocarbons is generally obtained at operating conditions including a temperature from 1000 F. to 1700 F.. preferably, l350 F. to 1550 F.; a pressure from 0 to 20 p.s.i.g,, preferably 5 to 10 p.s.i.g.; and a residence time in the pyrolysis reaction zone of from 0.5 to 25 seconds, preferably from 3 to 10 seconds.
  • an inert diluent such as steam, light gases, and the like, is used.
  • the prior art distinctly prefers to use superheated steam as the diluent which is added to the pyrolysis reaction zone in an amount from 0.2 to 1.0 pounds of steam per pound of hydrocarbon, preferably from 0.3 to 0.7 pound per pound, and typically, about 0.5 pound per pound.
  • a typical naphtha stream is introduced into the system via line 10 and pyrolyzed to desirable light olefinic gases in ethylene production facilities 11.
  • the desirable C minus hydrocarbons including the particularly desired ethylene stream is separated from the system via line 12.
  • a typical pyrolysis gasoline comprising C material separated from the efiiuent of the steam pyrolysis reaction zone is passed via line 13, pump 14, heater 15, into prefractionation or separation facilities 16.
  • the separation zone 16 comprises a distillation column maintained under conditions to separate gum materials and relatively non-volatile materials (such as those boiling above about 400 F.) may be removed via line 17.
  • the desirable feedstock fraction comprising, say, C to 400 F. hydrocarbons is withdrawn from separation zone 16 via line 19.
  • the feedstock is heated to substantially reaction temperature in heater 20, admixed with hydrogen from line 21, and further admixed with a hereinafter specified recycle stream from line 22.
  • This admixture comprising hydrogen and a combined hydrocarbon charge is passed via line 23 into reactor 24.
  • optimum reaction conditions may be obtained by minimizing the degree to which the feedstock is heated and maximizing the heat input through the recycle liquid stream and hydrogen stream; these conditions being consistent with effective vaporization and preferable limiting of temperature of any single stream to 550 F. and further limiting preferably the temperature of the fresh feed in line 19 to a temperature of no higher than about 420 F.
  • the term admixing said feedstock is intended to embody first admixing the feedstock and hydrogen, or first admixing the hydrogen and recycle liquid which is then admixed with the feedstock or any other combination of introducing these three streams into the first reaction zone.
  • the combined charge material plus a molar excess of hydrogen is passed through reactor 24 over the preferred palladium catalyst under conditions sufiicient to substantially convert diolefin compounds to olefin compounds without substantial saturation of olefin compounds.
  • the total efiiuent from reactor 24 is cooled in exchanger 26 in an amount sufiicient to produce in separator vessel 27 a significantly quantity of relatively heavy liquid.
  • the amount of relatively heavy liquid, more fully diwussed hereinafter, which is separated in separator 27 comprises from 30% to 70% by weight, typically about 50% by weight of the hydrocarbons in the effluent stream.
  • Operating conditions suitable for the achievement of the proper liquid phase in separator 27 include a temperature from 250 F. to 450 F., typically, about 330 F.
  • relatively light liquid which is condensed is withdrawn from separator 31 via line 22 and passed in part to first reactor 24, as previously mentioned, utilizing pump 59 and heater 60.
  • the separated gaseous phase or first gaseous fraction is withdrawn from separator 31 via line 21 and recycled to reactor 24, as previously men tioned, utilizing compressor 57 and heater 58.
  • the ma terial in line 21 comprises hydrogen, and sufiicient makeup hydrogen is added to the system via line 56.
  • the relatively heavy liquid portion produced in separator 27 is withdrawn via line 28, admixed with the remainder of the relatively light liquid in line 22 from line 32, and the admixture passed via line 33 into fractionating column 34.
  • These streams can be introduced separately into column 34 at different column locations, if desired.
  • Fractionating column 34 is maintained under suitable conditions to separate, as an overhead product, the C portion of the efiluent which is subsequently passed via line 35 to, for example, stabilization and further handling in accordance with well known practices in the art.
  • the bottoms from fractionating column 34 comprises the (3 material and is withdrawn via line 36 and passed into second fractionating column 37. Suitable distillation conditions are maintained in column 37 to separate as a bottoms product a relatively heavy gasoline fraction which is suitable for blending into motor fuel.
  • the material in line 38 comprises generally C hydrocarbons and the material in line 35 generally comprises C olefin-containing hydrocarbons. Both of these streams comprise hydrocarbons suitable for gasoline blending stock.
  • the overhead from distillation column 39 comprises an aromatic hydrocarbon concentrate and is withdrawn via line 39 through exchanger 40 into heater 43 via line 41 after admixture with hydrogen from line 42.
  • the heated aromatic concentrate-hydrogen mixture is passed via line 44 into second reactor 45 containing the preferred nickel-molybdate desulfurization catalyst.
  • second reactor 45 containing the preferred nickel-molybdate desulfurization catalyst.
  • Proper operating conditions are maintained in reactor 45, as previously mentioned, to effectuate saturation of the olefins contained in the aromatic concentrate stream as well as the substantial conversion of any sulfur compounds present therein to hydrogen sulfide.
  • the total efiluent from reactor 45 is withdrawn via line 46, passed through cooler 47 into separator 48, wherein a hydrogen fraction containing hydrogen sulfide gas is withdrawn via line 50 and recycled to reactor 45 utilizing compressor 52 in line 42. It should also be noted at this point that sufficient make-up hydrogen is cascaded from the first reaction zone system via lines 21 and 51. Thus, no fresh make-up hydrogen need be added to the reactor 45 system thereby enabling the confinement of the H S gases to the second reaction zone which contains a traditionally sulfur resistant catalyst. Otherwise, should hydrogen sulfide be passed through reactor 24, there would be a strong tendency for the palladium catalyst to convert or effectuate reaction between the hydrocarbons and hydrogen sulfide to produce undesirable mercaptans.
  • the condensed aromatic product stream is withdrawn from separator 48 via line 49 and passed into fractionating column 53. Suitable operating conditions are maintained in fractionating column 53 to produce a light ends fraction containing hydrogen and H 8 which is removed via line 54 and an aromatic hydrocarbon products stream which is removed via line 55 and which may be sent, for example, to solvent extraction for recovery of benzene, toluene, and/or xylene therefrom utilizing techniques well known to those skilled in the art.
  • the amount of relatively light liquid material in line 22 which is recycled to reactor 24 via line 23 is suflicient to produce a combined charge to reactor 24 which has a diene value less than 30 and particularly has a diene value' less than 20 and which typically is about 15.
  • a preferred embodiment of the present invention provides a method for stabilizing sulfur-containing pyrolysis gasoline which comprises the steps of: (a) separating said gasoline into a feedstock fraction comprising C to 400 F. hydrocarbons; (b) admixing said feedstock with hydrogen and a hereinafter specified recycle stream and introducing the admixture into a first reaction zone containing hydrogenating catalyst comprising palladium on lithiated alumina under conditions including a temperature from 200 F. to 500 F., a pressure from 100 p.s.i.g.
  • Another preferred embodiment of the invention includes the preferred embodiment hereinabove wherein the hydrogen introduced into said first reaction zone is substantially free of hydrogen sulfide and wherein the hydrogen present in said second reaction zone contains hydrogen sulfide.
  • Method for hydrogenating and desulfurizing hydrocarbons which comprises:
  • diolefin, monoolefin, and sulfur compounds boiling within the range from C to 400 F. with hydrogen and a suflicient amount of a hereinafter specified recycle stream to reduce the diene value of the resulting feed mixture to less than 30;
  • Method for stabilizing sulfur-containing pyrolysis gasoline which comprises the steps of:

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US644337A 1967-06-07 1967-06-07 Two-stage hydrogenation of an aromatic hydrocarbon feedstock containing diolefins,monoolefins and sulfur compounds Expired - Lifetime US3494859A (en)

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BE (1) BE715854A (enrdf_load_stackoverflow)
CH (1) CH505767A (enrdf_load_stackoverflow)
DE (1) DE1770575A1 (enrdf_load_stackoverflow)
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SE (1) SE346558B (enrdf_load_stackoverflow)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899412A (en) * 1972-03-13 1975-08-12 Ici Ltd Aromatics extraction process
US3969222A (en) * 1974-02-15 1976-07-13 Universal Oil Products Company Hydrogenation and hydrodesulfurization of hydrocarbon distillate with a catalytic composite
US4113603A (en) * 1977-10-19 1978-09-12 The Lummus Company Two-stage hydrotreating of pyrolysis gasoline to remove mercaptan sulfur and dienes
US4691070A (en) * 1984-06-28 1987-09-01 Toa Nenryo Kogyo Kabushiki Kaisha Catalyst, its method of preparation and process for its use in the hydrogenation of diolefins
US5868921A (en) * 1996-08-01 1999-02-09 Shell Oil Company Single stage, stacked bed hydrotreating process utilizing a noble metal catalyst in the upstream bed
US6830678B2 (en) * 2000-03-29 2004-12-14 Institut Francais Dupetrole Process of desulphurizing gasoline comprising desulphurization of the heavy and intermediate fractions resulting from fractionation into at least three cuts
EP3060627A4 (en) * 2013-10-25 2017-05-31 Uop Llc Pyrolysis gasoline treatment process
EP3060628A4 (en) * 2013-10-25 2017-06-07 Uop Llc Pyrolysis gasoline treatment process
US9834494B2 (en) 2014-09-29 2017-12-05 Uop Llc Methods and apparatuses for hydrocarbon production
RU2712090C1 (ru) * 2018-04-05 2020-01-24 Несте Ойй Способ и устройство гидрирования
US20230013013A1 (en) * 2021-06-23 2023-01-19 Saudi Arabian Oil Company Method of producing pyrolysis products from a mixed plastics stream and integration of the same in a refinery
US11692139B1 (en) 2022-02-10 2023-07-04 Saudi Arabian Oil Company Method of producing pyrolysis products from a mixed plastics stream
US11807815B2 (en) 2022-02-16 2023-11-07 Saudi Arabian Oil Company Method of producing plastic pyrolysis products from a mixed plastics stream
US12084619B2 (en) 2022-01-31 2024-09-10 Saudi Arabian Oil Company Processes and systems for producing fuels and petrochemical feedstocks from a mixed plastics stream

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3451922A (en) * 1967-04-28 1969-06-24 Universal Oil Prod Co Method for hydrogenation
US4173529A (en) * 1978-05-30 1979-11-06 The Lummus Company Hydrotreating of pyrolysis gasoline

Citations (5)

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US3167498A (en) * 1961-12-08 1965-01-26 Bayer Ag Process for the hydrogenation of hydrocarbons in the gasoline boiling range
US3190830A (en) * 1962-03-10 1965-06-22 British Petroleum Co Two stage hydrogenation process
US3226341A (en) * 1961-11-08 1965-12-28 Leesona Corp Method of preparing a catalyst composition consisting of lithium in a host metal of either group ib or viii
US3239453A (en) * 1962-11-19 1966-03-08 Socony Mobil Oil Co Inc Selective hydrogenation of hydrocarbons
US3239449A (en) * 1962-11-19 1966-03-08 Socony Mobil Oil Co Inc Selective conversion of unstable liquids

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3226341A (en) * 1961-11-08 1965-12-28 Leesona Corp Method of preparing a catalyst composition consisting of lithium in a host metal of either group ib or viii
US3167498A (en) * 1961-12-08 1965-01-26 Bayer Ag Process for the hydrogenation of hydrocarbons in the gasoline boiling range
US3190830A (en) * 1962-03-10 1965-06-22 British Petroleum Co Two stage hydrogenation process
US3239453A (en) * 1962-11-19 1966-03-08 Socony Mobil Oil Co Inc Selective hydrogenation of hydrocarbons
US3239449A (en) * 1962-11-19 1966-03-08 Socony Mobil Oil Co Inc Selective conversion of unstable liquids

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899412A (en) * 1972-03-13 1975-08-12 Ici Ltd Aromatics extraction process
US3969222A (en) * 1974-02-15 1976-07-13 Universal Oil Products Company Hydrogenation and hydrodesulfurization of hydrocarbon distillate with a catalytic composite
US4113603A (en) * 1977-10-19 1978-09-12 The Lummus Company Two-stage hydrotreating of pyrolysis gasoline to remove mercaptan sulfur and dienes
US4691070A (en) * 1984-06-28 1987-09-01 Toa Nenryo Kogyo Kabushiki Kaisha Catalyst, its method of preparation and process for its use in the hydrogenation of diolefins
US5868921A (en) * 1996-08-01 1999-02-09 Shell Oil Company Single stage, stacked bed hydrotreating process utilizing a noble metal catalyst in the upstream bed
US6830678B2 (en) * 2000-03-29 2004-12-14 Institut Francais Dupetrole Process of desulphurizing gasoline comprising desulphurization of the heavy and intermediate fractions resulting from fractionation into at least three cuts
EP3060627A4 (en) * 2013-10-25 2017-05-31 Uop Llc Pyrolysis gasoline treatment process
EP3060628A4 (en) * 2013-10-25 2017-06-07 Uop Llc Pyrolysis gasoline treatment process
US9834494B2 (en) 2014-09-29 2017-12-05 Uop Llc Methods and apparatuses for hydrocarbon production
WO2016053766A3 (en) * 2014-09-29 2018-05-11 Uop Llc Methods and apparatuses for hydrocarbon production
RU2712090C1 (ru) * 2018-04-05 2020-01-24 Несте Ойй Способ и устройство гидрирования
US10793789B2 (en) 2018-04-05 2020-10-06 Nestec Oyj Process and apparatus for hydrogenation
US20230013013A1 (en) * 2021-06-23 2023-01-19 Saudi Arabian Oil Company Method of producing pyrolysis products from a mixed plastics stream and integration of the same in a refinery
US12325832B2 (en) * 2021-06-23 2025-06-10 Saudi Arabian Oil Company Method of producing pyrolysis products from a mixed plastics stream and integration of the same in a refinery
US12084619B2 (en) 2022-01-31 2024-09-10 Saudi Arabian Oil Company Processes and systems for producing fuels and petrochemical feedstocks from a mixed plastics stream
US11692139B1 (en) 2022-02-10 2023-07-04 Saudi Arabian Oil Company Method of producing pyrolysis products from a mixed plastics stream
US11807815B2 (en) 2022-02-16 2023-11-07 Saudi Arabian Oil Company Method of producing plastic pyrolysis products from a mixed plastics stream
US12065617B2 (en) 2022-02-16 2024-08-20 Saudi Arabian Oil Company Method of producing plastic pyrolysis products from a mixed plastics stream

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DK136429C (enrdf_load_stackoverflow) 1978-03-06
FI50107B (enrdf_load_stackoverflow) 1975-09-01
FI50107C (fi) 1975-12-10
GB1220701A (en) 1971-01-27
NO123136B (enrdf_load_stackoverflow) 1971-10-04
NL157347B (nl) 1978-07-17
SE346558B (enrdf_load_stackoverflow) 1972-07-10
DK136429B (da) 1977-10-10
TR16736A (tr) 1973-05-01
BE715854A (enrdf_load_stackoverflow) 1968-10-16
DE1770575A1 (de) 1972-04-06
FR1582886A (enrdf_load_stackoverflow) 1969-10-10
ES354703A1 (es) 1970-02-16
NL6808087A (enrdf_load_stackoverflow) 1968-12-09
CH505767A (de) 1971-04-15

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