JP5022570B2 - ドープされた球形状の担持触媒及び金属を含む石油留分の水素処理及び水素化転化方法 - Google Patents
ドープされた球形状の担持触媒及び金属を含む石油留分の水素処理及び水素化転化方法 Download PDFInfo
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- JP5022570B2 JP5022570B2 JP2005084130A JP2005084130A JP5022570B2 JP 5022570 B2 JP5022570 B2 JP 5022570B2 JP 2005084130 A JP2005084130 A JP 2005084130A JP 2005084130 A JP2005084130 A JP 2005084130A JP 5022570 B2 JP5022570 B2 JP 5022570B2
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- beads
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- alumina
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- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910001679 gibbsite Inorganic materials 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000003077 lignite Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910000008 nickel(II) carbonate Inorganic materials 0.000 description 1
- ZULUUIKRFGGGTL-UHFFFAOYSA-L nickel(ii) carbonate Chemical group [Ni+2].[O-]C([O-])=O ZULUUIKRFGGGTL-UHFFFAOYSA-L 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical group [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910001682 nordstrandite Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical group [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000005204 segregation Methods 0.000 description 1
- CGFYHILWFSGVJS-UHFFFAOYSA-N silicic acid;trioxotungsten Chemical compound O[Si](O)(O)O.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1.O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 CGFYHILWFSGVJS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003476 subbituminous coal Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960004319 trichloroacetic acid Drugs 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/24—Chromium, molybdenum or tungsten
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- 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
- B01J21/04—Alumina
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- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/12—Silica and alumina
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- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
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- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
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- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/85—Chromium, molybdenum or tungsten
- B01J23/88—Molybdenum
- B01J23/883—Molybdenum and nickel
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- 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
- B01J37/0018—Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/02—Impregnation, coating or precipitation
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- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
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- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
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- 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
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- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
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- B01J35/635—0.5-1.0 ml/g
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- B01J35/638—Pore volume more than 1.0 ml/g
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- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
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Description
− 全細孔容積:0.7〜2cm3/g、
− 平均直径が100Å未満の細孔の全細孔容積の%:0〜10、
− 平均直径が100〜1000Åの細孔の全細孔容積の%:40〜90、
− 平均直径が1000〜5000Åの細孔の全細孔容積の%:5〜60、
− 平均直径が5000〜10000Åの細孔の全細孔容積の%:5〜50、
− 平均直径が10000Åを超える細孔の全細孔容積の%:5〜20。
a)ビーズ状アルミナの少なくとも一部を溶解させることを可能にする少なくとも1種の酸と、溶液中のアルミニウムイオンと結合することが可能であるアニオンを与える、少なくとも1種の化合物(この化合物は、前述の酸とは異なる化学種である)との混合物からなる水性媒体中で、活性アルミナビーズを処理する工程
b)同時に又は続いて、このように処理したビーズを、約数分〜約36時間の期間、約80℃〜約250℃の温度での処理に付す工程
c)場合によりビーズを乾燥させ、そして、それらに約500℃〜約1100℃の温度で熱活性化を受けさせる工程。
本発明により利用される活性アルミナビーズは、仏国特許発明第1 438 497号明細書に記載されたような方法により、不十分に結晶化した及び/又は非晶質の構造を有する活性アルミナ粉末からの細粒化によって調製される。この方法は、水溶液を用いて、不十分に結晶化した及び/又は非晶質の構造を有する活性アルミナを湿らせる工程と、グラニュレータでそれを凝集させる工程と、得られたビーズを好ましくは60〜約100℃の低温で、湿潤雰囲気下で熟成させさせる工程と、これらのビーズを約250℃〜約900℃の温度で乾燥させ、次にか焼する工程とからなる。
− 比表面積:80〜250m2/g
− 圧縮充填密度:約0.25〜0.65gr/cm3
− 全細孔容積(total pore volume:TPV):0.5〜約2.0cm3/g
− 水銀圧入測孔法技術によって決定される、細孔分布は、好ましくは次のように特徴付けられる:
− 平均直径が100Å未満の細孔の全細孔容積の%:0〜10、
− 平均直径が100〜1000Åの細孔の全細孔容積の%:40〜90、
− 平均直径が1000〜5000Åの細孔の全細孔容積の%:5〜60、
− 平均直径が5000〜10000Åの細孔の全細孔容積の%:5〜50、
− 平均直径が10000Åを超える細孔の全細孔容積の%:5〜20。
− 湿潤固体を10〜80℃の温度で浸潤雰囲気下で静置する工程と、
− 得られた湿潤固体を60〜150℃の温度で乾燥させる工程と、
− 乾燥後に得られた固体を150〜800℃の温度でか焼する工程とを含み得る。
− 平均直径が100Å未満の細孔の全細孔容積の%:0〜10、
− 平均直径が100〜1000Åの細孔の全細孔容積の%:40〜90、
− 平均直径が1000〜5000Åの細孔の全細孔容積の%:5〜60、
− 平均直径が5000〜10000Åの細孔の全細孔容積の%:5〜50、
− 平均直径が10000Åを超える細孔の全細孔容積の%:5〜20。
磨耗損失(%)=100(1−テスト後の0.6mmを超える触媒の重量/シリンダ中に装入された0.6mmを超える触媒の重量)
好適には、本発明による触媒の調製方法は、
a)ビーズ状のアルミナの少なくとも一部を溶解させることを可能にする少なくとも1種の酸と、溶液中のアルミニウムイオンと結合することが可能であるアニオンを与える、少なくとも1種の化合物(この化合物は、前述の酸とは異なる化学種である)との混合物からなる水性媒体中で、活性アルミナビーズを処理する工程と、
b)同時に又は続いて、このように処理したビーズを、数分〜36時間の期間、80〜250℃の温度での処理に付す工程と、
c)場合によりビーズを乾燥させ、そして、それらに500〜1100℃の温度で熱活性化を受けさせる工程と、
d)担体に、ホウ素、リン、ケイ素、及び第VIIA族元素(ハロゲン類)からなる群から選択される少なくとも1種のドーピング元素と、少なくとも1種の第VIB族元素と、場合により少なくとも1種の第VIII族元素とを導入する工程とを少なくとも含む。
− 湿潤固体を10〜80℃の温度で浸潤雰囲気下で静置する工程と、
− 得られた湿潤固体を60〜150℃の温度で乾燥させる工程と、
− 場合により、乾燥後に得られた固体を150〜800℃の温度でか焼する工程とを含む。
原料は、熱ガス流(T=1000℃)中での水礬土石の非常に急速な分解によって得られるアルミナである。得られた生成物は、遷移アルミナ混合物:(χ)及び(ρ)アルミナからなる。この生成物の比表面積は、300m2/gであり、かつ灼熱減量(loss on ignition:LOI)は、5%であった。
モリブデン及びニッケル塩を含む水溶液により、実施例1の担体を乾式含浸した。モリブデン塩は、ヘプタモリブデン酸アンモニウム(NH4)6Mo7O24・4H2Oであり、かつニッケル塩は、硝酸ニッケルNi(NO3)2・6H2Oである。水飽和雰囲気中で、周囲温度での成熟の後、含浸押出物は、120℃で終夜乾燥され、次に乾燥空気の下で2時間、500℃でか焼された。三酸化モリブデンの最終含有量は、最終触媒の重量の11%である。酸化ニッケルNiOの最終含有量は、最終触媒の重量の2.4%であった。
モリブデン及びニッケル塩、及びリン酸を含む水溶液により、実施例1の担体を乾式含浸した。モリブデンの前駆物質は、酸化モリブデンMoO3であり、ニッケルの前駆物質は、炭酸ニッケルNi(CO3)である。水飽和雰囲気中で、周囲温度での成熟の後、含浸押出物は、120℃で終夜乾燥され、次に乾燥空気の下で2時間、500℃でか焼された。三酸化モリブデンの最終含有量は、最終触媒の重量の9.4%であった。酸化ニッケルNiOの最終含有量は、最終触媒の重量の2%であった。酸化リンP2O5の最終含有量は、最終触媒の重量の2%であった。
MoO3、H2O2、Ni(OH)2、H2SO4及びポリメチルシロキサンのエマルジョンから調製された水溶液により、実施例1の担体を乾式含浸した。水飽和雰囲気中で、周囲温度での成熟の後、含浸押出物は、120℃で終夜乾燥され、次に乾燥空気の下で2時間、500℃でか焼された。三酸化モリブデンの最終含有量は、最終触媒の重量の9.2%であった。酸化ニッケルNiOの最終含有量は、最終触媒の重量の1.9%であった。酸化ケイ素SiO2の最終含有量は、最終触媒の重量の3.5%であった。
前記触媒A、B及びCは、異なる石油残渣の水素処理テストで比較した。それらは、一方では、中東起源(アラビアンライト(Arabian Light))の常圧残渣(atmospheric residue:AR)であり、かつ他方で、ベネズエラ超重質原油の常圧残渣(Boscan)のことである。これら2つの残渣は、高い粘度、高いコンラドソン炭素数(Conradson carbon numbers)及びアスファルテン含有量を特徴とする。Boscan ARは、その上非常に高いニッケル及びバナジウム含有量を含む。
HDM(重量%)=((Ni+V重量ppm)装入−(Ni+V重量ppm)テスト)/((Ni+V重量ppm)装入)×100
HDAsC7(重量%)=((n−ヘプタン中の不溶性アスファルテン重量%)装入−(n−ヘプタン中の不溶性アスファルテン重量%)テスト)/((n−ヘプタン中の不溶性アスファルテン重量%)装入)×100
HDCCR(重量%)=((CCR重量%)装入−(CCR重量%)テスト)/((CCR重量%)装入)×100
表3は、テスト開始時(50時間)及びテスト終了時(300時間)での触媒A、B及びCのHDM、HDAsC7及びHDCCR効率を比較する。
触媒A,B及びCの効率は、反応器内部で触媒を永続的に沸騰状態に維持することを可能にする装置を備えた管状反応器を含む試作装置中で、パイロットテストの間に比較した。利用する試作装置は、多数の特許、例えば米国特許第4 521 295号明細書、米国特許第4 495 060号明細書に記載された沸騰床での残渣の工業的なH−OIL水素化転化装置を代表する。
転化(重量%)=((550℃+の重量%)装入−(550℃+の重量%)テスト)/((550℃+の重量%)装入)×100
HDM(重量%)=((Ni+V重量ppm)装入−(Ni+V重量ppm)テスト)/((Ni+V重量ppm)装入)×100
次に、Boscan常圧残渣に、装入物を装入した。この装入物により、触媒の金属保持を評価することが可能になる。テストは、HDMを80〜60%に維持することを目的とする。このために、反応温度を410℃に維持した。HDM比率(%)が、60%未満に下落した時に、テストを停止する。燃料の良好な安定性を得るために、転化を50〜60重量%に維持する。形成した生成物の安定性を評価するために、「Shell P値」法による測定を、テスト後に回収される流出液の350℃+のフラクションに対して行った。
Claims (18)
- 触媒の存在下の金属を含む炭化水素装入物の固定床または沸騰床水素化転化および/または水素化処理方法であって、該触媒は、アルミナを主成分とするビーズ形態の担体と、第VIB族(元素周期表の新表記法の第6列)の少なくとも1種の触媒金属又は触媒金属化合物とを含み、細孔構造が、並置された複数の凝集体から構成され、各々が複数の針状小板で形成され、各凝集体の小板が、互いに対して、かつ凝集体の中心に対して概して放射状に配向され、前記触媒は、リンをドーピング元素として更に含み、最終触媒の重量に対する酸化物重量%で表すリン含有量は0.3〜10%である、方法。
- 前記触媒は、少なくとも1種の第VIII族(元素周期表の新表記法の第8、9、及び10列)の触媒金属又は触媒金属化合物を含む、請求項1に記載の方法。
- 前記触媒において、最終触媒の重量に対する酸化物重量%で表す、第VIB族金属含有量は、1〜20%であり、かつ最終触媒の重量に対する酸化物重量%で表す、第VIII族金属含有量は、0〜10%である、請求項1または2に記載の方法。
- 前記触媒において、第VIB族金属含有量は、1〜10重量%(酸化物)である、請求項1〜3のいずれか1つに記載の方法。
- 前記触媒において、水銀圧入測孔法技術によって決定された、細孔分布は:
− 平均直径が100Å未満の細孔の全細孔容積の%:0〜10、
− 平均直径が100〜1000Åの細孔の全細孔容積の%:40〜90、
− 平均直径が1000〜5000Åの細孔の全細孔容積の%:5〜60、
− 平均直径が5000〜10000Åの細孔の全細孔容積の%:5〜50、
− 平均直径が10000Åを超える細孔の全細孔容積の%:5〜20、のように特徴付けられる請求項1〜4のいずれか1つに記載の方法。 - 前記触媒において、圧縮充填密度は、0.35〜0.80g/cm3であり、かつ水銀圧入測孔法によって決定される全細孔容積は、0.4〜1.8g/cm3である、請求項1〜5のいずれか1つに記載の方法。
- 前記触媒において、VHg/2での細孔直径は、300〜700Åである、請求項1〜6のいずれか1つに記載の方法。
- 前記触媒は、第VIB族の元素としてモリブデンを含み、第VIII族の元素としてニッケルを含む、請求項1〜7のいずれか1つに記載の方法。
- 前記触媒において、ビーズのサイズは、0.5〜20mmである、請求項1〜8のいずれか1つに記載の方法。
- 前記触媒において、ビーズのサイズは、1〜6mmである、請求項1〜9のいずれか1つに記載の方法。
- 前記触媒は、
a)ビーズ状のアルミナの少なくとも一部を溶解させることを可能にする少なくとも1種の酸と、溶液中のアルミニウムイオンと結合することが可能であるアニオンを与える、少なくとも1種の化合物(この化合物は、前述の酸とは異なる化学種である)との混合物からなる水性媒体中で、活性アルミナビーズを処理する工程と、
b)同時にまたは続いて、このように処理したビーズを、数分〜36時間の期間、80〜250℃の温度での処理に付す工程と、
c)担体に、ホウ素、リン、ケイ素、及び第VIIA族元素(ハロゲン類)からなる群から選択される少なくとも1種のドーピング元素と、少なくとも1種の第VIB族元素とを導入する工程と
に従って調製される、請求項1に記載の方法。 - 工程c)は、担体に、選択された元素を含浸させることによって行われる、請求項11に記載の方法。
- 担体含浸の後に、
− 湿潤固体を10〜80℃の温度で浸潤雰囲気下で静置する工程と、
− 得られた湿潤固体を60〜150℃の温度で乾燥させる工程と
が続く、請求項12に記載の方法。 - 触媒の硫化処理が後に続く、請求項11〜13のいずれか1つに記載の方法。
- 前記金属含有装入物は、常圧残渣、直接蒸留から生じた減圧残渣、脱アスファルト油、コーキング転化方法からの残渣、固定床での水素化転化からの残渣、沸騰床での水素化転化からの残渣、または可動床での水素化転化法から生じた残渣から選択され、該装入物は、そのままで使用されるか、又は炭化水素フラクション若しくは炭化水素フラクション混合物によって希釈される、請求項1〜14のいずれか1つに記載の方法。
- 前記装入物の転化は、石炭の存在下に実施される、請求項1〜15のいずれか1つに記載の方法。
- 固定床で作動する、請求項1〜16のいずれか1つに記載の方法。
- 沸騰床で作動する、請求項1〜16のいずれか1つに記載の方法。
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-
2004
- 2004-03-23 FR FR0402980A patent/FR2867988B1/fr not_active Expired - Lifetime
- 2004-04-08 KR KR1020040023956A patent/KR101108408B1/ko not_active IP Right Cessation
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2005
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- 2005-03-16 EP EP05290587A patent/EP1579909B1/fr not_active Not-in-force
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- 2005-03-21 CA CA2500755A patent/CA2500755C/fr not_active Expired - Fee Related
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US20050211603A1 (en) | 2005-09-29 |
KR101108408B1 (ko) | 2012-02-09 |
FR2867988B1 (fr) | 2007-06-22 |
CA2500755C (fr) | 2013-01-08 |
EP1579909A1 (fr) | 2005-09-28 |
DE602005006037D1 (de) | 2008-05-29 |
JP2005270977A (ja) | 2005-10-06 |
DK1579909T3 (da) | 2008-08-11 |
CA2500755A1 (fr) | 2005-09-23 |
DE602005006037T2 (de) | 2008-07-10 |
KR20050094724A (ko) | 2005-09-28 |
EP1579909B1 (fr) | 2008-04-16 |
US7803266B2 (en) | 2010-09-28 |
FR2867988A1 (fr) | 2005-09-30 |
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