US3549515A - Hydrocracking process for high end point feeds - Google Patents

Hydrocracking process for high end point feeds Download PDF

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Publication number
US3549515A
US3549515A US642927A US64292767A US3549515A US 3549515 A US3549515 A US 3549515A US 642927 A US642927 A US 642927A US 64292767 A US64292767 A US 64292767A US 3549515 A US3549515 A US 3549515A
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United States
Prior art keywords
hydrocracking
feed
end point
catalyst
range
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Expired - Lifetime
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US642927A
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English (en)
Inventor
Alan J Brainard
Glen Porter Hamner
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ExxonMobil Technology and Engineering Co
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Exxon Research and Engineering Co
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Application filed by Exxon Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to US642927A priority Critical patent/US3549515A/en
Priority to GB5760169A priority patent/GB1297803A/en
Priority to FR7030364A priority patent/FR2101079B1/fr
Priority to DE19702041219 priority patent/DE2041219B2/de
Priority to NL7012693A priority patent/NL7012693A/xx
Application granted granted Critical
Publication of US3549515A publication Critical patent/US3549515A/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
    • 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

Definitions

  • This invention relates to a process for hydrocracking high end point feeds in a two-stage process with prehydrofining of the feed. More particularly the invention relates to selective hydrocracking employing a crystalline alumino-si1icate zeolite in conjunction with a platinum group metal hydrogenation component in the first hydrocracking stage.
  • hydrocracking process which will efiiciently handle high end point feeds.
  • Such a process would be designed to hydrocrack petroleum derived fractions containing at least 20 wt. percent of materials boiling above 750 F. and having an end point above 1000 F. to fuels fractions boiling in the range of C5-500 F.
  • the process would feature high throughput, a minimum of C4 and lighter products, and a minimum of bottoms product boiling above the fuels range.
  • This catalyst comprises a platinum group metal, e.g. palladium incorporated with a crystalline alumino-silicate zeolite.
  • This type of catalyst provides excellent hydrocracking results with stocks boiling in the range of about 300-750 F.
  • it has not been possible to obtain both high activity and long hydrocracking runs with high end point feeds.
  • the invention comprises the combination of steps comprising hydrofining a high end point petroleum feedstock at mild hydrofining conditions, hydrocracking the hydroiined feed at mild conditions in the presence of a catalyst comprising a platinum group metal incorporated with a crystalline alumino-silicate zeolite, fractionating the first stage hydrocrackate to obtain a low end point second stage hydrocracking feed boiling in the range of from about 350-400" F. to about 725-775 F., and containing less than about l p.p.m. nitrogen and less than about 5 wt. percent polycylic aromatics, recycling material boiling above about 725e775 F.
  • hydrofiner hydrocracking the low end point feed in a second hydrocracking stage at mild conditions in the presence of a selective but nitrogen sensitive catalyst, recovering parafnic fuel fractions and recycling material boiling above the fuels boiling point range to extinction in the second stage hydrocracker.
  • the petroleum feedstock treated in the process of the invention is characterized by a greater proportion of high boiling materials than a conventional hydrocracking feed.
  • the feed contains from 0.2-4.0 wt. percent sulfur and from 50-4000 p.p.m. nitrogen. Some of the nitrogen is in heavy organic ring compounds boiling above about 750 F. which are not hydrocracked at first pass conditions.
  • the feed is further characterized by an aromatic content of at least 20 Wt. percent, usually in the range of 20-50 wt. percent. Many of the aromatics are polycyclic aromatics i.e., 15-30 wt. percent. Some aromatics contain sulfur and nitrogen in the ring structure.
  • the feed boils in the gas oil boiling range, i.e., 400-l050 F.
  • feeds boils at a temperature above 750 F.
  • Most feeds have an end point above 1000 F., and thus they contain a high proportion of materials which will lay coke down on the catalyst unless measures are taken to prevent this.
  • Specific feeds include cycle oils from thermal and catalytic cracking, coker gas oils, heavy virgin gas oils, and blends of these.
  • the feed may also contain steam cracked fractions, coker naphtha and other fractions which must be hydrocracked under mild conditions to prevent coke formation.
  • a feed containing at least 50 ppm. nitrogen and at least 0.2 Wt. percent sulfur and boiling in the range of 400-1050 F. is passed by line 1 to hydrofiner 2.
  • Hydrofining is carried out at mild conditions to avoid any substantial cracking of the feed.
  • Hydrogen from line 3 is mixed with the feed and the reaction is preferably conducted in essentially the liquid phase with the reaction mixture passing downwardly over one or more fixed beds of a suitable hydrogenation catalyst. Typical hydrofining conditions are set forth below.
  • Suitable hydrolining catalyst include salts of metals of Group VI and VIII of the Periodic Table such as the oxides and/ or sulfides of cobalt, molybdenum, iron, nickel, tungsten and mixtures thereof.
  • the metal salts are supported on a suitable porous support material such as alumina, silica alumina, bauxite, magnesia and the like.
  • the preferred catalyst is one containing cobalt molybdate on silica stabilized alumina.
  • the nitrogen content of the feed will be reduced to less than 50 ppm. organic nitrogen.
  • the hydrofiner efiiuent is preferably fed directly by line 4 to the first stage hydrocracker 5 without condensation of vapors or removal of HZS or NH3.
  • the hydrofined feed is hydrocracked at mild conditions in the presence of a crystalline alumino-silicate zeolite composited with a platinum group metal.
  • zeolite materials Because of the ability of these zeolite materials to selectively adsorb molecules on the basis of their size and shape, they have often been referred to as molecular sieves.
  • the various types of molecular sieves may be classified according to the size of the molecules which will be rejected (i.e., not adsorbed by a particular sieve) which of course will be directly related to the diameter of the pore openings.
  • These zeolite materials have been extensively described in the patent literature; for example,
  • M is selected from the group consisting of metal cations and hydrogen
  • n is its valence
  • x is a number from about 1.5 to about l2.
  • They will usually have uniform pore openings of about 6 to l5, preferably 10 to 13 angstrom units in diameter.
  • the processes for producing these materials are well known in the art. They typically involve crystallization from reaction mixtures containing alumina, silica, alkali metal oxide, and water, all supplied by suitable source materials.
  • a type of synthetic zeolite which has recently gained wide acceptance as a hydrocracking catalyst support because of its greater stability and higher activity is the synthetic faujasite variety, wherein x in the above formula is about 2.5 to 7, preferably 3 to 6, most preferably 4 to 5.5.
  • the material has a crystal structure similar to the natural mineral faujasite and can be prepared by the procedure described in U.S. Pat. No. 3,130,007 ywhich refers to it as Zeolite Y.
  • Zeolite Y refers to it as Zeolite Y.
  • Other types of Zeolitic materials have also been found useful in hydrocracking processes.
  • synthetic mordenite has the capability of admitting aromatics into its pores, and will therefore be suitable.
  • the zeolites are usually subjected to cation exchange to reduce their alkali metal oxide content to less than about 10 wt. percent, preferably less than about 5 wt. percent.
  • the alkali metal oxide content has been reduced by ion exchange treatment with solutions of ammonium salts, or salts of metals in Groups I to VIII or the rare earth metals, preferably metal in Groups II, III, IV, V, VI-B, VII-B, VIII and the rare earth metals. Mixtures of these cations have also been employed.
  • the hydrogen and/or magnesium form of these zeolites has been preferred.
  • the modified crystalline zeolite is composited with a metallic hydrogenation component such as a platinum group metal for use as a hydrocracking catalyst.
  • a metallic hydrogenation component such as a platinum group metal for use as a hydrocracking catalyst.
  • This may be accomplished by treatment with a platinum or palladium salt or ammonium complex, e.g. platinous tetraaminodichloride, ammonium chloroplatinate, palladium chloride, etc.
  • Incorporation of the hydrogenation component may be accomplished by any conventional technique such as ion exchange followed by reduction, impregnation, etc.
  • the exchanged aluminosilicate is preferably impregnated Iwith an ammoniacal solution of palladium chloride-suflcient to produce the desired amount of hydrogenation metal in the final product, and then dried and calcined at a temperature of 800 to 1000 F. Reduction of the metal is then accomplished either separately or in the hydrocracking reaction, per se.
  • the amount of hydrogenation component may range from about 0.1 to about 25 wt. percent based on the weight of the nal product. In the case of platinum group metals, e.g. palladium, the preferred amount will be in the range of about 0.1 to 2, e.g., 0.3 to 1.0 wt. percent based on dry catalyst.
  • the rst stage hydrocracking is carried out at mild conditions like those set forth below.
  • a gas and light ends stream is removed overhead from the fractionator by line 13.
  • a naphtha fraction boiling in the range of C5-375" F. is removed by line 14.
  • a second stage hydrocracker feed boiling in the range of 350-750 F. is passed by line 15 to second stage hydrocracker 16.
  • the initial boiling point and the end point of the hydrocracker feed can be varied over the range of 350 to 440 F. and 700 to 750 F., respectively.
  • a bottoms fraction boiling above the end point of the feed to hydrocracker 16, i.e., preferably above about 750 F. is recycled by line 17 and 1 to hydroiiner 2.
  • the recycle stream contains essentially all of the heavy organic nitrogen compounds in the effluent from the first hydrocracking stage.
  • Hydrocracker 16 is also operated at mild hydrocracking conditions as set forth below.
  • metals of Groups VI-B and VIII-B particularly molybdenum, tungsten, cobalt, nickel and combinations of these metals.
  • the most preferred combinations of these metals are nickel with molybdenum and nickel with tungsten. From 10-30 wt. percent of the hydrogenation component is distended on the sieve base.
  • the catalyst is preferably sulfided prior to use.
  • Eflluent from hydrocracker 16 is passed by line 18 to high pressure separator 19.
  • a gas stream containing H2, H28 and NH3 is passed overhead from the separator by line 20 for recycle by lines 21 and 22.
  • Makeup hydrogen is supplied by line 22. If desired a part of the recycle gas can ⁇ be purged through line 23 or the gas can be purified by known means and then recycled.
  • Hydrocrackate is passed by line 24 to a second fractionator 25.
  • a gas and light ends fraction is recovered overhead by line 26.
  • a paraffinic naphtha fraction preferably boiling in the range of C5-375" F. for motor fue] is recovered by line 27.
  • a jet fuel fraction, preferably boiling in the range of 375-500 F. is recovered by line 28.
  • Line 29 is employed to recycle a bottoms fraction boiling above about 500 F., and is continuously recycled to the second hydrocracker.
  • all the liquid products of the process are fuels components and all materials boiling above about 500 F., i.e., 450- 5 50 F., are recycled to extinction.
  • hydrocracking feedstock passing the said hydrocracking feedstock to a second hydrocracking zone and hydrocracking the feedstock in the presence of a hydrogen containing gas and a hydrocracking catalyst comprising a crystalline alumino-silicate zeolite combined with a metal selected from the group consisting of Group VI-B, Group VIII-B and mixtures thereof at mild hydrocracking conditions including a temperature in the range of about 400-650" F. and a pressure in the range of 500-1500 p.s.i.g.,
  • the improvement comprising providing separate and distinct distillation zones for receipt of the product from each of the hydrocracking zones,
  • the catalyst of the hydrofining zone is characterized as a cobalt molybdate on silica alumina catalyst
  • the catalyst of the first hydrocracking zone is characterized as a crystalline aluminosilicate zeolite combined with palladium
  • the catalyst of the second hydrocracking zone is characterized as a hydrocracking catalyst comprising palladium on Zeolite Y
  • the fuels fractions which are recovered from the fractionation zones are char acterized as fuel fractions boiling in the range of C5 to about 500 F.

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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)
  • Catalysts (AREA)
US642927A 1967-06-01 1967-06-01 Hydrocracking process for high end point feeds Expired - Lifetime US3549515A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US642927A US3549515A (en) 1967-06-01 1967-06-01 Hydrocracking process for high end point feeds
GB5760169A GB1297803A (enrdf_load_stackoverflow) 1967-06-01 1969-11-25
FR7030364A FR2101079B1 (enrdf_load_stackoverflow) 1967-06-01 1970-08-18
DE19702041219 DE2041219B2 (de) 1967-06-01 1970-08-19 Verfahren zum hydrokracken hoch- siedender kohlenwasserstoffe
NL7012693A NL7012693A (enrdf_load_stackoverflow) 1967-06-01 1970-08-27

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US642927A US3549515A (en) 1967-06-01 1967-06-01 Hydrocracking process for high end point feeds
GB5760169 1969-11-25
FR7030364A FR2101079B1 (enrdf_load_stackoverflow) 1967-06-01 1970-08-18
DE19702041219 DE2041219B2 (de) 1967-06-01 1970-08-19 Verfahren zum hydrokracken hoch- siedender kohlenwasserstoffe
NL7012693A NL7012693A (enrdf_load_stackoverflow) 1967-06-01 1970-08-27

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DE (1) DE2041219B2 (enrdf_load_stackoverflow)
FR (1) FR2101079B1 (enrdf_load_stackoverflow)
GB (1) GB1297803A (enrdf_load_stackoverflow)
NL (1) NL7012693A (enrdf_load_stackoverflow)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779897A (en) * 1971-12-29 1973-12-18 Texaco Inc Hydrotreating-hydrocracking process for manufacturing gasoline range hydrocarbons
EP0081774A1 (en) * 1981-12-04 1983-06-22 Union Oil Company Of California Rare earth containing Y zeolite compositions
US4404088A (en) * 1981-10-02 1983-09-13 Chevron Research Company Three-stage hydrocracking process
US4421633A (en) * 1981-03-13 1983-12-20 Mobil Oil Corporation Low pressure cyclic hydrocracking process using multi-catalyst bed reactor for heavy liquids
US4565621A (en) * 1981-12-04 1986-01-21 Union Oil Company Of California Hydrocracking with rare earth-containing Y zeolite compositions
US4584287A (en) * 1981-12-04 1986-04-22 Union Oil Company Of California Rare earth-containing Y zeolite compositions
US4604187A (en) * 1981-12-04 1986-08-05 Union Oil Company Of California Hydrocracking with rare earth-containing Y zeolite compositions
US4950383A (en) * 1989-12-08 1990-08-21 The United States Of America As Represented By The Secretary Of The Air Force Process for upgrading shale oil
WO1993004146A1 (en) * 1991-08-15 1993-03-04 Mobil Oil Corporation Hydrocarbon upgrading process
US5198099A (en) * 1991-08-12 1993-03-30 Exxon Research And Engineering Company Three-stage process for producing ultra-clean distillate products
US5346609A (en) * 1991-08-15 1994-09-13 Mobil Oil Corporation Hydrocarbon upgrading process
US5348641A (en) * 1991-08-15 1994-09-20 Mobil Oil Corporation Gasoline upgrading process
US5352354A (en) * 1991-08-15 1994-10-04 Mobil Oil Corporation Gasoline upgrading process
US5407559A (en) * 1991-08-15 1995-04-18 Mobil Oil Corporation Gasoline upgrading process
US5409596A (en) * 1991-08-15 1995-04-25 Mobil Oil Corporation Hydrocarbon upgrading process
US20120125813A1 (en) * 2010-11-23 2012-05-24 Bridges Robert S Process for Cracking Heavy Hydrocarbon Feed
US8658023B2 (en) 2010-12-29 2014-02-25 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
US8658022B2 (en) 2010-11-23 2014-02-25 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
US8663456B2 (en) 2010-11-23 2014-03-04 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
CN104611051A (zh) * 2013-11-05 2015-05-13 中国石油化工股份有限公司 一种高干点重质馏分油加氢裂化方法
CN113680375A (zh) * 2021-09-09 2021-11-23 中化泉州石化有限公司 一种碳五石油树脂加氢催化剂及其制备方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159568A (en) * 1961-10-02 1964-12-01 Union Oil Co Low pressure hydrocracking process with hydrofining of feed
US3203889A (en) * 1962-11-01 1965-08-31 Universal Oil Prod Co Catalytic hydrocracking process with the preliminary hydrogenation of the aromatic containing feed oil
US3256177A (en) * 1964-11-03 1966-06-14 Union Oil Co Hydrocracking process

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB996428A (en) * 1964-03-02 1965-06-30 Union Oil Co Low pressure hydrocracking process

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3159568A (en) * 1961-10-02 1964-12-01 Union Oil Co Low pressure hydrocracking process with hydrofining of feed
US3203889A (en) * 1962-11-01 1965-08-31 Universal Oil Prod Co Catalytic hydrocracking process with the preliminary hydrogenation of the aromatic containing feed oil
US3256177A (en) * 1964-11-03 1966-06-14 Union Oil Co Hydrocracking process

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779897A (en) * 1971-12-29 1973-12-18 Texaco Inc Hydrotreating-hydrocracking process for manufacturing gasoline range hydrocarbons
US4421633A (en) * 1981-03-13 1983-12-20 Mobil Oil Corporation Low pressure cyclic hydrocracking process using multi-catalyst bed reactor for heavy liquids
US4404088A (en) * 1981-10-02 1983-09-13 Chevron Research Company Three-stage hydrocracking process
EP0081774A1 (en) * 1981-12-04 1983-06-22 Union Oil Company Of California Rare earth containing Y zeolite compositions
US4565621A (en) * 1981-12-04 1986-01-21 Union Oil Company Of California Hydrocracking with rare earth-containing Y zeolite compositions
US4584287A (en) * 1981-12-04 1986-04-22 Union Oil Company Of California Rare earth-containing Y zeolite compositions
US4604187A (en) * 1981-12-04 1986-08-05 Union Oil Company Of California Hydrocracking with rare earth-containing Y zeolite compositions
US4950383A (en) * 1989-12-08 1990-08-21 The United States Of America As Represented By The Secretary Of The Air Force Process for upgrading shale oil
US5198099A (en) * 1991-08-12 1993-03-30 Exxon Research And Engineering Company Three-stage process for producing ultra-clean distillate products
US5352354A (en) * 1991-08-15 1994-10-04 Mobil Oil Corporation Gasoline upgrading process
US5348641A (en) * 1991-08-15 1994-09-20 Mobil Oil Corporation Gasoline upgrading process
WO1993004146A1 (en) * 1991-08-15 1993-03-04 Mobil Oil Corporation Hydrocarbon upgrading process
JPH06509830A (ja) * 1991-08-15 1994-11-02 モービル・オイル・コーポレイション 炭化水素品質向上方法
US5407559A (en) * 1991-08-15 1995-04-18 Mobil Oil Corporation Gasoline upgrading process
US5409596A (en) * 1991-08-15 1995-04-25 Mobil Oil Corporation Hydrocarbon upgrading process
JP2788348B2 (ja) 1991-08-15 1998-08-20 モービル・オイル・コーポレイション 炭化水素品質向上方法
US5346609A (en) * 1991-08-15 1994-09-13 Mobil Oil Corporation Hydrocarbon upgrading process
US8663456B2 (en) 2010-11-23 2014-03-04 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
US20120125813A1 (en) * 2010-11-23 2012-05-24 Bridges Robert S Process for Cracking Heavy Hydrocarbon Feed
US8658022B2 (en) 2010-11-23 2014-02-25 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
US8658019B2 (en) * 2010-11-23 2014-02-25 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
US8658023B2 (en) 2010-12-29 2014-02-25 Equistar Chemicals, Lp Process for cracking heavy hydrocarbon feed
CN104611051A (zh) * 2013-11-05 2015-05-13 中国石油化工股份有限公司 一种高干点重质馏分油加氢裂化方法
CN104611051B (zh) * 2013-11-05 2016-09-07 中国石油化工股份有限公司 一种高干点重质馏分油加氢裂化方法
CN113680375A (zh) * 2021-09-09 2021-11-23 中化泉州石化有限公司 一种碳五石油树脂加氢催化剂及其制备方法
CN113680375B (zh) * 2021-09-09 2023-08-25 中化泉州石化有限公司 一种碳五石油树脂加氢催化剂及其制备方法

Also Published As

Publication number Publication date
DE2041219B2 (de) 1977-07-07
FR2101079A1 (enrdf_load_stackoverflow) 1972-03-31
DE2041219A1 (de) 1972-02-24
FR2101079B1 (enrdf_load_stackoverflow) 1974-09-20
GB1297803A (enrdf_load_stackoverflow) 1972-11-29
NL7012693A (enrdf_load_stackoverflow) 1972-02-29

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