JP2004269847A - C7+パラフィンの異性化方法及びそれのための触媒 - Google Patents
C7+パラフィンの異性化方法及びそれのための触媒 Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000012188 paraffin wax Substances 0.000 title description 2
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 229910052751 metal Inorganic materials 0.000 claims abstract description 18
- 239000002184 metal Substances 0.000 claims abstract description 18
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 15
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 12
- 229910001930 tungsten oxide Inorganic materials 0.000 claims abstract description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 8
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000010937 tungsten Substances 0.000 claims abstract description 8
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 7
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910001928 zirconium oxide Inorganic materials 0.000 claims abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 5
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 4
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 229910052721 tungsten Inorganic materials 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 150000002739 metals Chemical class 0.000 abstract description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 238000005336 cracking Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- UJVRJBAUJYZFIX-UHFFFAOYSA-N nitric acid;oxozirconium Chemical compound [Zr]=O.O[N+]([O-])=O.O[N+]([O-])=O UJVRJBAUJYZFIX-UHFFFAOYSA-N 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 3
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 zirconia Chemical class 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical group [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003657 tungsten Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/58—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins
- C10G45/60—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used
- C10G45/62—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to change the structural skeleton of some of the hydrocarbon content without cracking the other hydrocarbons present, e.g. lowering pour point; Selective hydrocracking of normal paraffins characterised by the catalyst used containing platinum group metals or compounds 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/652—Chromium, molybdenum or tungsten
- B01J23/6527—Tungsten
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
【解決手段】アルミニウム、タングステン及びジルコニウムの混合酸化物と、水素化/脱水素化成分、例えば白金、パラジウムもしくは他の第VIII族金属とを含む触媒を用いて、C4+パラフィンを選択的に異性化する。供給物は、場合によっては、より短鎖のパラフィン、芳香族化合物またはシクロパラフィンを含んでいてもよい。
【選択図】なし
Description
(a)ジルコニウム及びアルミニウムの酸化物/水酸化物とタングステン前駆体とを含む混合物を混練し、
(b)この混練された混合物を成形し、
(c)この混合物を、600℃〜900℃、最も好ましくは650℃〜800℃の温度でか焼し、
(d)この触媒を、第VIII族金属で含浸処理し、
(e)得られた材料を300℃〜800℃、最も好ましくは300℃〜500℃でか焼する、
ことを含む。
硝酸ジルコニルの水溶液に希釈したアンモニア水を加えそしてpHを9に調節することによって酸化ジルコニウムを製造した。この混合物を一晩還流した。得られた白色の固形物を濾過、洗浄し、そして120℃で一晩乾燥した。この乾燥された材料は333m2 /gの表面積を有していた。ジルコニア225g、アルミナゲル(シュードベーマイト30重量%)168g及びメタタングステン酸アンモニウム62gを15分間混合し、そして押出成形して1/16インチ押出物とした。この触媒を、700℃で三時間、か焼した。このか焼した触媒のXRDは、図1に示すようにアルミナの存在を示した。Pd0.5重量%を、インシピエント・ウェットネス(Incipient wetness) 含浸法により導入した。反応器に入れる前に触媒を350℃でか焼した。
例2、比較例
酸化ジルコニウムを、硝酸ジルコニルの水溶液に希釈されたアンモニア水を加えそしてpHを9に調節することによって製造した。この混合物を一晩還流した。この白色の固形物を濾過、洗浄し、そして120℃で一晩乾燥した。この乾燥された材料は、333m2 /gの表面積を有していた。ジルコニア225g及びメタタングステン酸アンモニウム62gを十分な量の水と混合して、押出成形可能なペーストを調製した。このペーストを15分間混合し、そして押出成形して1/16インチの押出物とした。この触媒を3時間700℃でか焼し、そしてPd0.5重量%を、インシピエント・ウェットネス含浸法により導入した。反応器に入れる前にこの触媒を350℃でか焼した。
例3
酸化ジルコニウムを、硝酸ジルコニルの水溶液に希釈されたアンモニア水を加え、そしてpHを9に調節することによって製造した。この混合物を一晩還流した。この白色の固形物を濾過、洗浄し、そして120℃で一晩乾燥した。この乾燥された材料は、333m2 /gの表面積を有していた。ジルコニア225g、アルミナゲル(シュードベーマイト30重量%)168g及びメタタングステン酸アンモニウム62gを15分間混合しそして押出成形して1/16インチ押出物とした。この触媒を700℃で3時間か焼した。Pt0.5重量%を、インシピエント・ウェットネス含浸法により導入した。反応器に入れる前にこの触媒を350℃でか焼した。
例4
190℃の温度、1h-1のLHSV、7barの全圧下、1:2の比率の水素:炭化水素混合物からなる供給物を用いて、例1に従い製造された触媒によりヘプタンの異性化を固定床反応器中で行った。生成物の組成の詳細を表1に記す。
190℃の温度、1h-1のLHSV、7barの全圧下、1:2の比率の水素:炭化水素混合物からなる供給物を用いて、例2に従い製造された触媒によりヘプタンの異性化を固定床反応器中で行った。生成物の組成の詳細を表2に示す。
例6
165℃の温度、0.2h-1のLHSV、6barの圧力下に、1:2の比率の水素:炭化水素混合物からなる供給物を用いて、例1に従い製造された触媒によりヘプタンの異性化を固定床反応器中で行った。生成物の組成の詳細を表3に記す。
Claims (5)
- C4+炭化水素留分を含む炭化水素供給物流からハイオクタンガソリンを製造する方法であって、タングステンオキシアニオンで変性されたアルミニウム及びジルコニウム混合酸化物と第VIII族金属の水素化/脱水素化成分とを含む触媒組成物に異性化条件下に上記供給物を接触させることを含む、上記方法。
- 炭化水素供給物が、C7+炭化水素を少なくとも20重量%の割合で含む、請求項1の方法。
- 異性化条件が、炭化水素に対する比率が0.1〜5の水素の存在、150℃〜300℃の温度範囲、1〜40barの全圧、及び0.1〜30h-1の液体空間速度LHSVを含む、請求項1の方法。
- 触媒が、乾質基準で、酸化タングステンを10〜50重量%及び酸化アルミニウムを10〜40重量%の割合で含み、そして残りがジルコニア及び第VIII族金属である、請求項1の方法。
- 第VIII族金属が、0.01〜5%の量の白金及び/またはパラジウムである、請求項1の方法。
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DKPA200201414 | 2002-09-25 |
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JP2004269847A true JP2004269847A (ja) | 2004-09-30 |
JP2004269847A5 JP2004269847A5 (ja) | 2006-11-02 |
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JP2003331751A Pending JP2004269847A (ja) | 2002-09-25 | 2003-09-24 | C7+パラフィンの異性化方法及びそれのための触媒 |
Country Status (6)
Country | Link |
---|---|
US (1) | US7893312B2 (ja) |
EP (1) | EP1402947B1 (ja) |
JP (1) | JP2004269847A (ja) |
AT (1) | ATE464120T1 (ja) |
DE (1) | DE60332075D1 (ja) |
ES (1) | ES2341950T3 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2013521104A (ja) * | 2009-03-02 | 2013-06-10 | ズードケミー インコーポレイテッド | 活性化された酸化ジルコニウム触媒支持体 |
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DE102004040522A1 (de) * | 2004-08-20 | 2006-02-23 | Süd-Chemie AG | Saurer wolframhaltiger Katalysator |
US20060270885A1 (en) * | 2005-05-31 | 2006-11-30 | Boyer Christopher C | Normal heptane isomerization |
US20070119748A1 (en) * | 2005-11-28 | 2007-05-31 | Konrad Herbst | Process for the preparation of a paraffin isomerization catalyst |
US7833933B2 (en) * | 2005-11-28 | 2010-11-16 | Haldor Topsøe A/S | Process for the preparation of a paraffin isomerization catalyst |
US20080032886A1 (en) * | 2006-08-03 | 2008-02-07 | Abb Lummus Global, Inc. | Doped solid acid catalyst composition, process of conversion using same and conversion products thereof |
DE102007004351A1 (de) | 2007-01-29 | 2008-07-31 | Evonik Degussa Gmbh | Neue Katalysatoren und Verfahren zur Dehydratisierung von Glycerin |
FI20195647A1 (en) | 2019-07-22 | 2021-01-23 | Neste Oyj | Paraffin products, method of production of paraffin products and use of paraffin products |
CN111569861B (zh) * | 2020-05-29 | 2023-04-07 | 河北工业大学 | 一种将异构烷烃转化为正构烷烃的反应用催化剂及其制备方法 |
US20220403258A1 (en) * | 2021-06-17 | 2022-12-22 | ExxonMobil Technology and Engineering Company | Methods and systems for paraffin isomerization optimization |
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US5837641A (en) * | 1996-01-16 | 1998-11-17 | Uop Llc | Method of promoting the activity of solid strong acid catalysts |
KR100327891B1 (ko) * | 1996-09-05 | 2002-03-15 | 노미야마 아키히콰 | 고체산촉매 및 그 제조방법 |
-
2003
- 2003-09-11 EP EP03020668A patent/EP1402947B1/en not_active Expired - Lifetime
- 2003-09-11 DE DE60332075T patent/DE60332075D1/de not_active Expired - Lifetime
- 2003-09-11 AT AT03020668T patent/ATE464120T1/de not_active IP Right Cessation
- 2003-09-11 ES ES03020668T patent/ES2341950T3/es not_active Expired - Lifetime
- 2003-09-17 US US10/663,647 patent/US7893312B2/en not_active Expired - Fee Related
- 2003-09-24 JP JP2003331751A patent/JP2004269847A/ja active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2004537404A (ja) * | 2001-08-07 | 2004-12-16 | マサチューセッツ・インスティチュート・オブ・テクノロジー | 固体酸性触媒のための非ゼオライト系ナノ複合体物質 |
WO2003080768A1 (fr) * | 2002-03-27 | 2003-10-02 | Japan Energy Corporation | Procede d'isomerisation d'hydrocarbures |
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JP2013521104A (ja) * | 2009-03-02 | 2013-06-10 | ズードケミー インコーポレイテッド | 活性化された酸化ジルコニウム触媒支持体 |
Also Published As
Publication number | Publication date |
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ATE464120T1 (de) | 2010-04-15 |
ES2341950T3 (es) | 2010-06-30 |
US20040059174A1 (en) | 2004-03-25 |
DE60332075D1 (de) | 2010-05-27 |
EP1402947B1 (en) | 2010-04-14 |
EP1402947A1 (en) | 2004-03-31 |
US7893312B2 (en) | 2011-02-22 |
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