JP5399234B2 - 液体炭化水素質供給原料の全酸価(tan)の低下方法 - Google Patents
液体炭化水素質供給原料の全酸価(tan)の低下方法 Download PDFInfo
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- 238000000034 method Methods 0.000 title claims description 29
- 239000007788 liquid Substances 0.000 title claims description 24
- 239000002253 acid Substances 0.000 title claims description 23
- 239000003054 catalyst Substances 0.000 claims description 29
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000010779 crude oil Substances 0.000 claims description 20
- 239000007789 gas Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 6
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 239000000047 product Substances 0.000 claims 3
- 239000012043 crude product Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 229910052757 nitrogen Chemical group 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000000737 periodic effect Effects 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004438 BET method Methods 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229910000311 lanthanide oxide Inorganic materials 0.000 description 3
- 229910052747 lanthanoid Inorganic materials 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 3
- 229910010271 silicon carbide Inorganic materials 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000012808 vapor phase Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910003294 NiMo Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004517 catalytic hydrocracking Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical group O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- -1 lanthanide metal oxide Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
Classifications
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- 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
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/066—Zirconium or hafnium; Oxides or hydroxides 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
-
- 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
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/063—Titanium; 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/10—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of rare earths
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/615—100-500 m2/g
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/63—Pore volume
- B01J35/633—Pore volume less than 0.5 ml/g
-
- 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
-
- 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
- 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)
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1033—Oil well production fluids
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
- C10G2300/203—Naphthenic acids, TAN
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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)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
Description
本発明は、液体炭化水素質供給原料、特に原油の全酸価 (TAN)の低下方法に関する。
多量の酸を含有する原油、その他の液体炭化水素質流は精製困難である。特に原油製油所の蒸留ユニットでは多量の酸が腐食の問題を引き起こす。液体炭化水素質供給原料から水素化処理、即ち、硫黄及び窒素のような他のヘテロ原子を除去する水素化処理法により酸が除去されることが知られている。しかし、水素化処理は、製油所において蒸留ユニットの下流で行われる方法である。
水素化脱硫、水素化脱窒素及び水素化分解のような通常、水素化転化反応に使用される水素化成分を本質的に含まない触媒、即ち、周期表第5〜10欄のいずれか1種の金属の化合物は、液体炭化水素質流、特に原油中の酸を選択的に水素化するのに使用できることが見出された。
本発明方法では液体炭化水素質供給原料は水素含有ガスの存在下、200〜400℃の範囲の温度及び高圧で、元素の周期表第3又は4欄の金属の酸化物又はランタニドの酸化物を含むが、第5〜10欄の金属又はその化合物を本質的に含まない触媒と接触させる。
本発明方法に使用される供給原料の全酸価は、供給原料1当たり0.2mgKOH以上、好ましくは0.5mgKOH以上、なお更に好ましくは1.0mgKOH以上である。ここで全酸価とはASTM D664で測定して供給原料1g当たりのKOH量(mg)のことである。
全酸価の低い液体炭化水素質生成物のTANは、供給原料のTANに対し、好ましくは50%以下、更に好ましくは30%以下となるような程度に低下される。
微細流反応器中で原油を水素含有ガス又は窒素の存在下、固体不活性物質(0.1mmの炭化珪素粒子)又は以下に述べる触媒(炭化珪素粒子で希釈した触媒粒子)の一つと少なくとも100時間接触させた。各種の原油を使用した。実験1〜8及び13〜16では、西アフリカ原油(原油1)を使用し、実験9〜12では中東の原油(原油2)を使用した。両原油の仕様を第1表に示す。各実験の正確な条件を第2表に示す。
水素化実験で以下の触媒を使用した。
チタニア触媒1
チタニア触媒(更にチタニア1と云う)を次のようにして製造した。チタニア粉末(P25、デグサから;燃焼減量:540℃で4.4重量%)3192g量を混合摩砕混練機(シンプソン)中で蓚酸2水和物100gと混合した。4分間混合摩砕後、脱イオン水981g及びポリエチレングリコール100gを加え、更に12分間混合摩砕を続けた。次いで、メチルセルロース100gを加え、更に20分間混合摩砕を続けた。こうして形成された混合物を押出しにより直径1.7mmの三葉状ダイプレートを通して造形した。この三葉体を120℃で2時間乾燥後、500℃で2時間焼成した。
チタニア触媒(更にチタニア2と云う)として市販のX096(CRI Catalyst Campanyから)チタニア粒子を使用した。このチタニア粒子の表面積は窒素吸着法(BET法)で測定して120m2/g、細孔容積は水銀侵入法で測定して0.32ml/gであった。
次のようにしてジルコニア触媒を製造した。ジルコニア粉末(RC100、Daiichiから;燃焼減量:540℃で5.3重量%)264g量を混練機(Werner&Pfeider Sigma混練機タイプLUK0.75)中でポリビニルアルコールの5重量%脱イオン水溶液90gと混合した。7分間混練後、カチオン性ポリアクリルアミド(Superflock,Cytecから)を加え、20分間混練後、脱イオン水8gを加えた。この混合物を更に22分間混練した。こうして形成された混合物を押出しにより直径1.7mmの三葉体に造形した。押出物を120℃で2時間乾燥後、550℃で2時間焼成した。
アルミナ上に Ni及び Moを担持して従来の水素化脱硫触媒(Criterion Catalyst Companyから)の市販品CRITERION RM?5030を使用した。
b)ガス速度:油1kg当たり標準リットルガス
e)TAN:油1kg当たりKOHmg
d)測定せず:液体流出物は硫化水素臭がなかった。
e)測定せず:液体流出物は硫化水素臭があった。
f)合成ガス組成:水素33.2容量%、CO20.7容量%、残部窒素
Claims (9)
- 液体炭化水素質供給原料が、前記供給原料1g当たり0.2mgKOH以上の全酸価(TAN)を有し、かつ前記供給原料が原油であり、前記供給原料を水素含有ガスの存在下、200〜400℃の範囲の温度及び2〜200バールゲージ圧の高圧で、酸化チタン及び/又は酸化ジルコニウムを必須成分とするが、第5〜10族の金属又はその化合物を本質的に含まない触媒と接触させて、全酸価(TAN)の低い液体炭化水素質生成物を得ることを特徴とする液体炭化水素質供給原料の全酸価の低下方法。
- 前記酸化物が酸化チタン又は酸化ジルコニウムである請求項1に記載の方法。
- 前記触媒が酸化チタン及び/又は酸化ジルコニウムを必須成分とする請求項2に記載の方法。
- 前記圧力が10〜150 バールゲージ圧である請求項1〜3のいずれか1項に記載の方法。
- 前記温度が250〜390℃である請求項1〜4のいずれか1項に記載の方法。
- 前記水素含有ガスが合成ガス又は水素である請求項1〜5のいずれか1項に記載の方法。
- 前記供給原料のTANが、供給原料1g当たり0.5mgKOH以上である請求項1〜6のいずれか1項に記載の方法。
- 前記液体炭化水素質生成物のTANが、供給原料1g当たり、0.2mgKOH以下、好ましくは0.1mgKOH以下である請求項1〜7のいずれか1項に記載の方法。
- 前記低い全酸価を有する液体炭化水素質生成物のTANが、原油生成物の TANに対
し50%以下である請求項1〜8のいずれか1項に記載の方法。
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2006/061302 WO2007112782A1 (en) | 2006-04-04 | 2006-04-04 | A process for reducing the total acid number (tan) of a liquid hydrocarbonaceous feedstock |
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JP2012253528A Division JP2013057075A (ja) | 2012-11-19 | 2012-11-19 | 液体炭化水素質供給原料の全酸価(tan)の低下方法 |
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JP2009532536A JP2009532536A (ja) | 2009-09-10 |
JP5399234B2 true JP5399234B2 (ja) | 2014-01-29 |
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EP (1) | EP2001976A1 (ja) |
JP (1) | JP5399234B2 (ja) |
CN (1) | CN101405371B (ja) |
AU (1) | AU2006341463A1 (ja) |
CA (1) | CA2647760C (ja) |
MX (1) | MX2008012567A (ja) |
WO (1) | WO2007112782A1 (ja) |
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Publication number | Priority date | Publication date | Assignee | Title |
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GB496779A (en) * | 1937-01-04 | 1938-12-06 | Bataafsche Petroleum | A process for removing naphthenic acids from mineral lubricating oils or lubricating oil fractions |
US3846288A (en) * | 1973-07-05 | 1974-11-05 | Gulf Research Development Co | Acid number reduction of hydrocarbon fractions using a solid catalyst and methanol |
US6547957B1 (en) * | 2000-10-17 | 2003-04-15 | Texaco, Inc. | Process for upgrading a hydrocarbon oil |
US20020148754A1 (en) * | 2001-02-08 | 2002-10-17 | Gong William H. | Integrated preparation of blending components for refinery transportation fuels |
BRPI0405739B1 (pt) * | 2003-12-19 | 2014-06-17 | Shell Int Research | Método para produzir um produto de petróleo bruto, e, sistema para produzir um produto de petróleo bruto |
WO2006014486A1 (en) * | 2004-07-07 | 2006-02-09 | California Institute Of Technology | Process to upgrade oil using metal oxides |
-
2006
- 2006-04-04 JP JP2009503427A patent/JP5399234B2/ja not_active Expired - Fee Related
- 2006-04-04 EP EP06725538A patent/EP2001976A1/en not_active Withdrawn
- 2006-04-04 WO PCT/EP2006/061302 patent/WO2007112782A1/en active Application Filing
- 2006-04-04 MX MX2008012567A patent/MX2008012567A/es unknown
- 2006-04-04 AU AU2006341463A patent/AU2006341463A1/en not_active Abandoned
- 2006-04-04 CN CN200680053992.8A patent/CN101405371B/zh not_active Expired - Fee Related
- 2006-04-04 CA CA2647760A patent/CA2647760C/en not_active Expired - Fee Related
Also Published As
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WO2007112782A1 (en) | 2007-10-11 |
CA2647760C (en) | 2013-12-10 |
CN101405371A (zh) | 2009-04-08 |
JP2009532536A (ja) | 2009-09-10 |
CA2647760A1 (en) | 2007-10-11 |
MX2008012567A (es) | 2008-10-10 |
EP2001976A1 (en) | 2008-12-17 |
CN101405371B (zh) | 2012-07-18 |
AU2006341463A1 (en) | 2007-10-11 |
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