US20070029228A1 - Hydrocracking catalyst and process for producing liquid hydrocarbon - Google Patents

Hydrocracking catalyst and process for producing liquid hydrocarbon Download PDF

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Publication number
US20070029228A1
US20070029228A1 US11/532,640 US53264006A US2007029228A1 US 20070029228 A1 US20070029228 A1 US 20070029228A1 US 53264006 A US53264006 A US 53264006A US 2007029228 A1 US2007029228 A1 US 2007029228A1
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US
United States
Prior art keywords
catalyst
percent
hydrocracking
alumina
present
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US11/532,640
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English (en)
Inventor
Nobuo Aoki
Hiroyuki Seki
Masahiro Higashi
Masakazu Ikeda
Toshio Waku
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eneos Corp
Original Assignee
Nippon Oil Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Oil Corp filed Critical Nippon Oil Corp
Assigned to NIPPON OIL CORPORATION reassignment NIPPON OIL CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: AOKI, NOBUO, HIGASHI, MASAHIRO, IKEDA, MASAKAZU, SEKI, HIROYUKI, WAKU, TOSHIO
Publication of US20070029228A1 publication Critical patent/US20070029228A1/en
Priority to US12/178,691 priority Critical patent/US7700818B2/en
Abandoned legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/064—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof containing iron group metals, noble metals or copper
    • B01J29/068—Noble metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
    • B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
    • B01J29/12—Noble metals
    • B01J29/126—Y-type faujasite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
    • B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/10—After treatment, characterised by the effect to be obtained
    • B01J2229/20—After treatment, characterised by the effect to be obtained to introduce other elements in the catalyst composition comprising the molecular sieve, but not specially in or on the molecular sieve itself
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
    • B01J2229/30—After treatment, characterised by the means used
    • B01J2229/42—Addition of matrix or binder particles
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
    • B01J29/20—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type containing iron group metals, noble metals or copper
    • B01J29/22—Noble metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
    • B01J29/42—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively containing iron group metals, noble metals or copper
    • B01J29/44—Noble metals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J29/00—Catalysts comprising molecular sieves
    • B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
    • B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
    • B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
    • B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
    • B01J29/74—Noble metals
    • B01J29/7415—Zeolite Beta
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
    • 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
    • C10G2400/06—Gasoil

Definitions

  • the present invention relates to a catalyst for producing liquid hydrocarbons from paraffinic hydrocarbons in the presence of hydrogen and a process for producing liquid hydrocarbons using such a catalyst.
  • Patent Document 1 discloses a catalyst comprising platinum loaded into a support containing silica alumina.
  • Non-Patent Document 1 wherein the hydrocracking of a paraffinic hydrocarbon was carried out using a catalyst comprising platinum loaded into a crystalline aluminosilicate (zeolite).
  • the crystalline aluminosilicate catalyst is at a satisfactorily higher level of the cracking activity but has disadvantages that the middle distillate yield is low and the resulting gas oil fails to obtain a sufficient pour point.
  • amorphous solid acid catalysts a typical example of which is silica alumina are at satisfactorily higher level in middle distillate yield and the pour point of the resulting gas oil but low in cracking activity. That is, there has not been developed a catalyst which satisfies high cracking activity and middle distillate yield as well as the low pour point of the resulting gas oil all together, resulting in a serious hindrance to an improvement of economical efficiency of the hydrocracking process of paraffinic hydrocarbons.
  • Patent Document 1 Japanese Patent Laid-Open Publication No. 6-41549
  • Non-Patent Document 2 “Zeolite” (Volume 6, page 334 to 348, 1986)
  • the present invention has an object to provide a novel catalyst for hydrocracking paraffinic hydrocarbons which can satisfy higher cracking activity and middle distillate yield and the lower pour point of the resulting gas oil all together thereby improving the productivity of the hydrocracking process.
  • the present invention relates to a catalyst for hydrocracking paraffinic hydrocarbons which comprises a crystalline aluminosilicate, alumina-boria and a noble metal of Group VIII of the Periodic Table.
  • the present invention also relates to the above-described catalyst wherein the average particle diameter of the crystalline aluminosilicate is 0.5 ⁇ m or smaller.
  • the present invention also relates a process for producing liquid hydrocarbons wherein paraffinic hydrocarbons are hydrocracked using the foregoing catalyst.
  • aluminosilicate used herein denotes a metal oxide constituted by three elements, i.e., aluminum, silicon, and oxygen. Although another metal element may coexist to an extent that the present invention is not prohibited from achieving the advantageous effects, the amount of such a metal element is 5 percent by mass or less and preferably 3 percent by mass or less of the total amount of alumina and silica in the form of an oxide.
  • the metal element which may coexist are titanium, lanthanum, manganese, gallium and zinc. Preferred are titanium and lanthanum.
  • the crystallinity of aluminosilicate can be estimated with the proportion of tetrahedrally coordinated Al atoms in all the Al atoms which proportion can be measured by a solid 27 Al NMR spectrum.
  • the term “crystalline aluminosilicate” used in the present invention denotes that whose proportion of tetrahedrally coordinated Al atoms is 50 percent or more. Any crystalline aluminosilicate can be used in the present invention as long as the proportion of tetrahedrally coordinated Al atoms is 50 percent or more. However, it is preferred to use those containing 70 percent or more of the tetrahedrally coordinated Al atoms, and it is more preferred to use those containing 80 percent or more of the tetrahedrally coordinated Al atoms.
  • Crystalline aluminosilicates eligible for the present invention are so-called zeolites. Preferred are Y- or USY-type zeolites, beta-type zeolites, mordenite, and ZSM-5, and most preferred is USY-type zeolite. If necessary, two or more types of crystalline aluminosilicates may be used.
  • the average particle diameter of the crystalline aluminosilicate to be used in the present invention is preferably 1.0 ⁇ m or smaller and particularly preferably 0.5 ⁇ m or smaller.
  • the hydrocracking catalyst of the present invention is characterized in that it comprises a crystalline aluminosilicate and alumina-boria.
  • alumina-boria No particular limitation is imposed on the content ratio of alumina to boria in alumina-boria.
  • the ratio of alumina to boria is preferably 30 to 99 percent by mass: 70 to 1 percent by mass, more preferably 50 to 95 percent by mass: 50 to 5 percent by mass, and most preferably 70 to 90 percent by mass: 30 to 10 percent by mass.
  • the mass ratio of the crystalline aluminosilicate to alumina-boria in the catalyst is preferably from 0.001 to 2.000, more preferably 0.010 to 1.500 and most preferably 0.015 to 0.200.
  • the catalyst may be molded into a desired shape without using a binder.
  • a binder may be used if necessary.
  • No particular limitation is imposed on the binder.
  • preferred binders are alumina, silica, silica-alumina, titania and magnesia, and most preferred is alumina.
  • No particular limitation is imposed on the percentage of binder in the whole molded catalyst. However, it is usually from 5 to 99 percent by mass and preferably from 20 to 99 percent by mass.
  • the catalyst of the present invention necessarily contains a noble metal of Group VIII of the Periodic Table as an active component.
  • a metal other than that of Group VIII of the Periodic Table is used as an active agent, the middle distillate yield obtained by a hydrocracking process using a catalyst containing such a metal is extremely reduced thereby failing to achieve the purposes of the present invention.
  • the noble metal of Group VIII of the Periodic Table include cobalt, nickel, rhodium, palladium, iridium, and platinum. Most preferred are palladium and platinum.
  • the catalyst of the present invention can be produced by loading these metals into the above-described molded catalyst by a well-known method such as impregnation or ion-exchange.
  • two or more noble metals may be loaded in combination.
  • both platinum and palladium may be loaded.
  • No particular limitation is imposed on the loaded amount of the noble metal. The amount is usually from 0.02 to 2 percent by mass based on the total mass of the catalyst.
  • paraffinic hydrocarbon used herein denotes hydrocarbons the paraffin molecule content of which is 70 percent by mol or more. No particular limitation is imposed on the carbon atom number of the hydrocarbon molecules. However, those having from 10 to 100 carbon atoms are usually used.
  • the catalyst of the present invention is particularly effective for hydrocracking paraffinic hydrocarbons having 20 or more carbon atoms, so-called “wax”.
  • the catalyst of the present invention is applicable to various paraffinic hydrocarbons such as petroleum-based or synthetic paraffinic hydrocarbons.
  • particularly preferred paraffinic hydrocarbons are so-called FT waxes produced by Fischer-Tropsch synthesis.
  • the catalyst of the present invention may be used in a conventional fixed bed reactor apparatus.
  • the reaction conditions are a reaction temperature of 200 to 500° C., a hydrogen pressure of 0.5 to 12 MPa, and an LHSV (liquid hourly space velocity) of a paraffinic hydrocarbon feedstock of 0.1 to 10/h.
  • Preferred conditions are a reaction temperature of 250 to 400° C., a hydrogen pressure of 2.0 to 8.0 MPa, and an LHSV (liquid hourly space velocity) of a paraffinic hydrocarbon feedstock of 0.3 to 5.0/h.
  • the catalyst of the present invention comprising the above-described aluminosilicate, alumina-boria and a noble metal of Group VIII of the Periodic Table is used for hydrocracking paraffinic hydrocarbons, it can achieve high cracking activity and middle distillate yield and the low pour point of the resulting liquid hydrocarbon all together.
  • a column-like support with a size of 1/16 inch (about 1.6 mm) comprising 30 g of a USY zeolite with an average particle diameter of about 0.4 ⁇ m and 970 g of alumina-boria was impregnated with an aqueous solution containing dichlorotetraammine platinum (II) in such an amount that the amount of the platinum element was 0.8 percent by mass of the support.
  • the support was dried at a temperature of 120° C. for 3 hours and calcined at a temperature of 500° C. for one hour thereby preparing a catalyst.
  • the catalyst thus prepared (200 ml) was filled into a fixed bed flow reactor and used to hydrocrack a paraffinic hydrocarbon.
  • the feedstock used herein was an FT wax whose paraffin content was 95 percent and carbon number distribution was from 20 to 80.
  • the hydrogen pressure was 3 MPa, while the LHSV of the feedstock was 2.0/h.
  • the fraction whose boiling point was 360° C. or lower was defined as “cracked product”.
  • the reaction temperature at which the cracked product in an amount of 80 percent by mass based on the feed stock was obtained was measured. Also measured were the yield of the middle distillate whose boiling point was from 145° C. to 360° C. and the pour point of the resulting gas oil whose boiling point was from 260° C. to 360° C.
  • Table 1 The results are set forth in Table 1 below.

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  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Catalysts (AREA)
US11/532,640 2004-03-29 2006-09-18 Hydrocracking catalyst and process for producing liquid hydrocarbon Abandoned US20070029228A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US12/178,691 US7700818B2 (en) 2004-03-29 2008-07-24 Process for producing liquid hydrocarbon with hydrocracking catalyst

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2004-094817 2004-03-29
JP2004094817A JP4313237B2 (ja) 2004-03-29 2004-03-29 水素化分解触媒および液状炭化水素の製造方法
PCT/JP2005/004728 WO2005092500A1 (fr) 2004-03-29 2005-03-10 Catalyseur d'hydrocraquage et procédé de fabrication d’hydrocarbure liquide

Related Parent Applications (1)

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US (2) US20070029228A1 (fr)
EP (1) EP1733789A4 (fr)
JP (1) JP4313237B2 (fr)
CN (2) CN103212431A (fr)
AU (1) AU2005225266B2 (fr)
MY (1) MY165564A (fr)
WO (1) WO2005092500A1 (fr)

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US20050241991A1 (en) * 2004-04-28 2005-11-03 Headwaters Heavy Oil, Llc Ebullated bed hydroprocessing methods and systems and methods of upgrading an existing ebullated bed system
US20050241992A1 (en) * 2004-04-28 2005-11-03 Lott Roger K Fixed bed hydroprocessing methods and systems and methods for upgrading an existing fixed bed system
US20060201854A1 (en) * 2004-04-28 2006-09-14 Headwaters Heavy Oil, Llc Methods and mixing systems for introducing catalyst precursor into heavy oil feedstock
US20090107881A1 (en) * 2007-10-31 2009-04-30 Headwaters Technology Innovation, Llc Methods for increasing catalyst concentration in heavy oil and/or coal resid hydrocracker
US20090159490A1 (en) * 2006-01-30 2009-06-25 Hiroyuki Seki Method of hydrogenolysis of wax and process for producing fuel base
US20090166265A1 (en) * 2005-12-09 2009-07-02 Hiroyuki Seki Hydrorefining method
US20090173666A1 (en) * 2008-01-03 2009-07-09 Headwaters Technology Innovation, Llc Process for increasing the mono-aromatic content of polynuclear-aromatic-containing feedstocks
US20100122935A1 (en) * 2007-05-01 2010-05-20 Nippon Oil Corporation Method of producing liquid fuel
US20100170828A1 (en) * 2006-03-30 2010-07-08 Nippon Oil Corporation Hydrocracking catalyst and process for producing fuel base material
US9169449B2 (en) 2010-12-20 2015-10-27 Chevron U.S.A. Inc. Hydroprocessing catalysts and methods for making thereof
US9644157B2 (en) 2012-07-30 2017-05-09 Headwaters Heavy Oil, Llc Methods and systems for upgrading heavy oil using catalytic hydrocracking and thermal coking
US9790440B2 (en) 2011-09-23 2017-10-17 Headwaters Technology Innovation Group, Inc. Methods for increasing catalyst concentration in heavy oil and/or coal resid hydrocracker
CN112138642A (zh) * 2020-09-27 2020-12-29 福州大学 一种裂化催化剂的制备方法和用途
US11091707B2 (en) 2018-10-17 2021-08-17 Hydrocarbon Technology & Innovation, Llc Upgraded ebullated bed reactor with no recycle buildup of asphaltenes in vacuum bottoms
US11118119B2 (en) 2017-03-02 2021-09-14 Hydrocarbon Technology & Innovation, Llc Upgraded ebullated bed reactor with less fouling sediment
US11414607B2 (en) 2015-09-22 2022-08-16 Hydrocarbon Technology & Innovation, Llc Upgraded ebullated bed reactor with increased production rate of converted products
US11414608B2 (en) 2015-09-22 2022-08-16 Hydrocarbon Technology & Innovation, Llc Upgraded ebullated bed reactor used with opportunity feedstocks
US11421164B2 (en) 2016-06-08 2022-08-23 Hydrocarbon Technology & Innovation, Llc Dual catalyst system for ebullated bed upgrading to produce improved quality vacuum residue product
US11732203B2 (en) 2017-03-02 2023-08-22 Hydrocarbon Technology & Innovation, Llc Ebullated bed reactor upgraded to produce sediment that causes less equipment fouling

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JP5180427B2 (ja) * 2004-06-01 2013-04-10 出光興産株式会社 含蝋原料油の水素化分解触媒
US7462338B2 (en) 2004-12-28 2008-12-09 Umicore Ag & Co. Kg Boron-alumina catalyst support
JP4848191B2 (ja) * 2006-02-13 2011-12-28 Ｊｘ日鉱日石エネルギー株式会社 合成油の水素化処理方法
JP4908022B2 (ja) * 2006-03-10 2012-04-04 Ｊｘ日鉱日石エネルギー株式会社 炭化水素油の製造方法および炭化水素油
JP4908037B2 (ja) * 2006-03-30 2012-04-04 Ｊｘ日鉱日石エネルギー株式会社 合成油の処理方法、灯油煙点向上剤用炭化水素油及びディーゼル燃料基材用炭化水素油
JP4908038B2 (ja) * 2006-03-30 2012-04-04 Ｊｘ日鉱日石エネルギー株式会社 合成油の処理方法、水素製造用炭化水素油及びディーゼル燃料基材用炭化水素油
JP4808172B2 (ja) * 2006-03-30 2011-11-02 Ｊｘ日鉱日石エネルギー株式会社 水素化分解触媒および燃料基材の製造方法
JP2007269897A (ja) * 2006-03-30 2007-10-18 Nippon Oil Corp ワックスの水素化分解方法
JP2007270061A (ja) * 2006-03-31 2007-10-18 Nippon Oil Corp 液体燃料基材の製造方法
CN101410181B (zh) * 2006-03-31 2011-07-20 新日本石油株式会社 加氢裂解催化剂和燃料基材的制造方法
AU2007322907B2 (en) * 2006-11-21 2011-11-24 Nippon Oil Corporation Process for producing liquid fuel
AU2008206002B2 (en) * 2007-01-15 2011-11-17 Nippon Oil Corporation Processes for production of liquid fuel
JP5660956B2 (ja) 2011-03-31 2015-01-28 独立行政法人石油天然ガス・金属鉱物資源機構 水素化分解触媒及び炭化水素油の製造方法
JP5660957B2 (ja) 2011-03-31 2015-01-28 独立行政法人石油天然ガス・金属鉱物資源機構 再生水素化分解触媒及び炭化水素油の製造方法
JP2012211344A (ja) * 2012-08-08 2012-11-01 Jx Nippon Oil & Energy Corp ワックスの水素化分解方法

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JP4313237B2 (ja) 2009-08-12
CN103212431A (zh) 2013-07-24
CN1938090A (zh) 2007-03-28
JP2005279382A (ja) 2005-10-13
AU2005225266B2 (en) 2010-07-15
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US20080306321A1 (en) 2008-12-11
WO2005092500A1 (fr) 2005-10-06

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