AU2004205788B2 - Cerium oxide nanoparticles as fuel additives - Google Patents
Cerium oxide nanoparticles as fuel additives Download PDFInfo
- Publication number
- AU2004205788B2 AU2004205788B2 AU2004205788A AU2004205788A AU2004205788B2 AU 2004205788 B2 AU2004205788 B2 AU 2004205788B2 AU 2004205788 A AU2004205788 A AU 2004205788A AU 2004205788 A AU2004205788 A AU 2004205788A AU 2004205788 B2 AU2004205788 B2 AU 2004205788B2
- Authority
- AU
- Australia
- Prior art keywords
- cerium oxide
- fuel
- doped
- detergent
- fuel additive
- 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.)
- Expired
Links
- 229910000420 cerium oxide Inorganic materials 0.000 title claims description 82
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 title claims description 82
- 239000002816 fuel additive Substances 0.000 title claims description 21
- 239000002105 nanoparticle Substances 0.000 title description 5
- 239000000446 fuel Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 36
- 239000003599 detergent Substances 0.000 claims description 28
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 27
- 239000000654 additive Substances 0.000 claims description 18
- 125000001931 aliphatic group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- -1 praeseodymium Chemical compound 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- 229960002317 succinimide Drugs 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000002283 diesel fuel Substances 0.000 claims description 11
- 239000002518 antifoaming agent Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052723 transition metal Inorganic materials 0.000 claims description 7
- 150000003624 transition metals Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000013556 antirust agent Substances 0.000 claims description 6
- 238000002485 combustion reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical group 0.000 claims description 5
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 5
- 150000002910 rare earth metals Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 235000006708 antioxidants Nutrition 0.000 claims description 4
- 229910052752 metalloid Inorganic materials 0.000 claims description 4
- 150000002738 metalloids Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 229920000768 polyamine Polymers 0.000 claims description 4
- 229940014800 succinic anhydride Drugs 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 239000002879 Lewis base Substances 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 238000011049 filling Methods 0.000 claims description 3
- 150000007527 lewis bases Chemical class 0.000 claims description 3
- 239000006078 metal deactivator Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical group CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 claims description 2
- KAYAKFYASWYOEB-UHFFFAOYSA-N 3-octadec-1-enyloxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCCCC=CC1CC(=O)OC1=O KAYAKFYASWYOEB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 229920002367 Polyisobutene Polymers 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229960001124 trientine Drugs 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 229910052684 Cerium Inorganic materials 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 229910052771 Terbium Inorganic materials 0.000 claims 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910017052 cobalt Inorganic materials 0.000 claims 1
- 239000010941 cobalt Substances 0.000 claims 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 1
- 239000010948 rhodium Substances 0.000 claims 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims 1
- 229910052711 selenium Inorganic materials 0.000 claims 1
- 239000011669 selenium Substances 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims 1
- 239000010936 titanium Substances 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 5
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000006280 diesel fuel additive Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
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- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/12—Inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L10/00—Use of additives to fuels or fires for particular purposes
- C10L10/02—Use of additives to fuels or fires for particular purposes for reducing smoke development
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/12—Inorganic compounds
- C10L1/1233—Inorganic compounds oxygen containing compounds, e.g. oxides, hydroxides, acids and salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Solid Fuels And Fuel-Associated Substances (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Catalysts (AREA)
Description
WO 2004/065529 PCT/GB2004/000294 CERIUM OXIDE NANOPARTICLES AS FUEL ADDITIVES 5 This invention relates to cerium oxide nanoparticles which are useful as fuel additives. Cerium oxide is widely used as a catalyst in three way converters for the elimination of toxic exhaust emission gases and the reduction in particulate emissions in automobiles. The ceria contained within the catalyst can act as a 10 chemically active component, working as an oxygen store by release of oxygen in the presence of reductive gases, and removal of oxygen by interaction with oxidising species. Cerium oxide may store and release oxygen by the following processes: 15 2CeO2++Ce 2
O
3 + 1/202 The key to the use of ceria for catalytic purposes is the low redox potential between the Ce 3 * and Ce 4 * ions (1.7V) that allows the above reaction to easily occur in exhaust gases. Cerium oxide may provide oxygen for the oxidation of CO or C"H" 20 or may absorb oxygen for the reduction of NO.. The amounts of oxygen reversibly provided in and removed from the gas phase are called the oxygen storage capacity (OSC) of ceria. The above catalytic activity may occur when cerium oxide is added as an additive to fuel, for example diesel or petrol. However, in order for this effect to be 25 useful the cerium oxide must be of a particle size small enough to remain in a stable dispersion in the fuel. The cerium oxide particles must be of a nanocrystalline nature, for example they should be less than 1 micron in size, and preferentially 1 300nm in size. In addition, as catalytic effects are surface area dependant the small particle size renders the nanocrystalline material more effective as a catalyst. 30 The incorporation of cerium oxide in fuel serves more than one purpose. The primary purpose is to act as a catalyst in the reduction of toxic exhaust gases on 2 combustion of the fuel. However, it can serve another purpose in diesel engines. Diesel engines increasingly comprise a trap for particulates resulting from combustion of the diesel fuel. The presence of the cerium oxide in the traps helps to burn off the particulates which accumulate in the trap. Indeed such a use is in 5 commercial operation. Thus certain vehicles, principally those devised by Peugeot, incorporate an on-board dosing system whereby cerium oxide is incorporated into the fuel before the latter enters the engine. This is, though, a complicated system and requires extensive electronic control to feed the appropriate amount of additive to the fuel. Effectively, the on-board system 10 enables the particulate filter to be regenerated so that it lasts much longer. The applicants have now found, according to the present invention, a different use for cerium oxide nanoparticles whereby the particles are added to fuel at an earlier stage. It has been found that incorporating the particles in this way can lead to improved fuel efficiency. 15 Accordingly, the present invention provides a method of improving the efficiency of a fuel for an internal combustion engine which comprises adding to the fuel prior to the introduction of the fuel to a vehicle or other apparatus comprising an internal combustion engine cerium oxide and/or doped cerium oxide and a detergent and, optionally, one or more fuel additives. 20 By introducing the cerium oxide in this way there is no need for any vehicle fuel management system. Fuel efficiency will result from the incorporation of the cerium oxide particles in the fuel. The particles can be incorporated into the fuel at various different points. There are particular advantages associated with their introduction at these 25 various different points. In particular, the cerium oxide can be incorporated at the refinery, typically along with processing additives. This is, of course, the earliest point at which the cerium oxide can be added and it means that the fuel available at the refinery already contains the additive so that there is no need for it to be introduced at a later stage. However, if desired, it can be added at the fuel 30 company's depot which means that the amount incorporated can be customised to the individual company's S:\patricia\cases\2\25895\AU\OO\Amended pages DRAFT 770921.doc\\ WO 2004/065529 PCT/GB2004/000294 -3 requirements. Alternatively, the cerium oxide can be added at the public or private filling station forecourt either to the storage tank or dispensed to the fuel on delivery to the vehicle; this has the advantage that there will be maximum stabilisation of the particle dispersion. 5 It will be appreciated that although the principal purpose of adding the cerium oxide to the fuel is to increase fuel economy, the presence of the particles in the fuel will, at the same time, help to regenerate a diesel particulate filter if present. The effect of the cerium oxide is generally to enable regeneration to take place at a lower temperature. This has the advantage that the filter which is usually of a ceramic 10 material is generally less likely to crack. Although it is possible to use ordinary cerium oxide particles it has been found to be beneficial to use cerium oxide which has been doped with components that result in additional oxygen vacancies being formed. This generally means that the dopant will be di- or tri-valent in order to provide oxygen vacancies. 15 Such dopant ions must be di- or tri-valent ions of an element which is a rare earth metal, a transition metal or a metal of Group IIA, IIIB, VB, or VIB of the Periodic Table in order to provide oxygen vacancies. They must also be of a size that allows incorporation of the ion within the surface region of the cerium oxide nanoparticles. Accordingly metals with a large ionic radius should not be used. For 20 example transition metals in the first and second row of transition metals are generally preferred over those listed in the third. The ceria serves as the oxygen activation and exchange medium during a redox reaction. However, because ceria and the like are ceramic materials, they have low electronic conductivity and low activity surface sites for the chemisorption of the reacting species. Transition metal 25 additives are particularly useful to improve this situation. In addition, multivalent dopants will also have a catalytic effect of their own. Typically the doped oxides will have the formula Cel-M0 2 where M is a said metal or metalloid, in particular Rh, Cu, Ag, Au, Pd, Pt, Sb, Se, Fe, Ga, Mg, Mn, Cr, Be, B, Co, V, Zr, Ti and Ca as well as Pr, Sm and Gd and x has a value up to 0.3, 30 typically 0.01 or 0.1 to 0.2, or of the formula [(CeO 2
)
1 ,(REOy)n] I.kM'k where M' is a WO 2004/065529 PCT/GB2004/000294 -4 said metal or metalloid other than a rare earth, RE is a rare earth, y is 1 or 1.5 and each of n and k, which may be the same or different, has a value op to 0.5, preferably up to 0.3, typically 0.01 or 0.1 to 0.2. Further details can be found in our PCT Application GB2002/005013 to which reference should be made. 5 In general the cerium oxide particles will have a size not exceeding 1 micron and especially not exceeding 300 nm, for example 1 to 300 nm, such as from 1 to 150 nm, in particular 1 to 50 nm, especially 1 to 20 nm . It is preferred that the particles are coated to prevent agglomeration. For this purpose the particles can be comminuted in an organic solvent in the presence of a 10 coating agent which is an organic acid, anhydride or ester or a Lewis base. It has been found that, in this way which involves coating in situ, it is possible to significantly improve the coating of the oxide. Further, the resulting product can, in many instances, be used directly without any intermediate step. Thus in some coating procedures it is necessary to dry the coated particles before dispersing them 15 in a hydrocarbon solvent. Thus the cerium oxide can be dispersible or soluble in the (liquid) fuel or another hydrocarbon compatible with the fuel. The particles which are subjected to the process should have as large a surface area as possible and preferably the particles have a surface area, before 20 coating, of at least 10 m 2 /g and preferably a surface area-of at least 50 or 75 m 2 /g, for example 80-150 m 2 /g, or 100-300m 2 /g. The coating agent is suitably an organic acid, anhydride or ester or a Lewis base. The coating agent is preferably an organic carboxylic acid or an anhydride, typically one possessing at least 8 carbon atoms, for example 10 to 25 carbon atoms, 25 especially 12 to 18 carbon atoms such as stearic acid. It will be appreciated that the carbon chain can be saturated or unsaturated, for example ethylenically unsaturated as in oleic acid. Similar comments apply to the anhydrides which can be used. They are preferably dicarboxylic acid anhydrides, especially alkenyl succinic anhydrides, particularly dodecenylsuccinic anhydride, octadecenylsuccinic anhydride and 30 polyisobutenyl succinic anhydride. Other organic acids, anhydrides and esters which WO 2004/065529 PCT/GB2004/000294 -5 can be used in the process of the present invention include those derived from phosphoric acid and sulphonic acid. The esters are typically aliphatic esters, for example alkyl esters where both the acid and ester parts have 4 to 18 carbon atoms. The coating process can be carried out in an organic solvent. Preferably, the -5 solvent is non-polar and is also preferably non-hydrophilic. It can be an aliphatic or an aromatic solvent. Typical examples include toluene, xylene, petrol, diesel fuel as well as heavier fuel oils. Naturally, the organic solvent used should be selected so that it is compatible with the intended end use of the coated particles. The presence of water should be avoided; the use of an anhydride as coating agent helps to 10 eliminate any water present. The coating process involves comminuting the particles so as to prevent any agglomerates from forming. Techniques which can be used for this purpose include high-speed stirring or tumbling and the use of a colloid mill, ultrasonics or ball milling. Ball milling is preferred. Further details of such coatings can be found in 15 PCT/GB02/02312. It can be pointed out that the concentration of cerium oxide in the fuel can generally be less than that used in an on-board dosing system. Thus the concentration of cerium oxide in the fuel generally does not exceed 20 ppm and typically not exceed 10 ppm. In general, the minimum concentration is of the order 20 of 1-2 ppm. The particles can be incorporated into the fuel directly or as part of an additive package which is added to the fuel. The particles are preferably incorporated into diesel fuel. The present invention is particularly useful for large vehicles such as trucks and buses where an on-board dosing system would generally not be 25 incorporated. The fuel can also be used for static engines such as generators. The nature of the formulation used to incorporate the cerium oxide will, of course, vary depending on the point at which the cerium oxide is introduced. In general it has been found that the cerium oxide particles can be stabilised in the fuel or fuel additive package by the presence of a detergent. In this connection 30 it will be appreciated that lubricity agents can have an adverse effect since these can WO 2004/065529 PCT/GB2004/000294 -6 cause a precipitate to form. Particular detergents which can be used in the present invention include a basic nitrogen-containing detergent. Such detergents should be ashless i.e. they contain no metals. Suitable detergents include aides, amines, Mannich bases and succinimides which are preferred. Preferably the detergent is a 5 succinimide, which has an average of at least 3 nitrogen atoms per molecule. The succinimide is preferably aliphatic and may be saturated or unsaturated, especially ethylencally unsaturated, e.g. an alkyl or alkenyl succinimide. Typically the detergent is formed from an alkyl or alkenyl succinic acylating agent, generally having at least 35 carbon atoms in the alkyl or alkenyl group, and an alkylene 10 polyamine mixture having an average of at least 3 nitrogen atoms per molecule. Preferably it can be formed from a polyisobutenyl succinic acylating agent derived from polyisobutene having a number average molecular weight of 500 to 10,000 and an ethylene polyamine which can include cyclic and acyclic parts, having an average composition from triethylene tetramine to pentaethylene hexamine. Thus the chain 15 will typically have a molecular weight from 500 to 2500, especially 750 to 1500 with those having molecular weights around 900 and 1300 being particularly useful although a succinimide with an aliphatic chain with a molecular weight of about 2100 is also useful. Further details can be found in US-A-5,932,525 and 6048373 and EP-A-432,941, 460309 and 1,237,373. 20 Accordingly, the present invention also provides-a fuel additive composition which comprises cerium oxide and/or doped cerium oxide together with a detergent, preferably an aliphatic succinimide. Typically the concentration of cerium oxide in the additive will be from 0.1 to 10%, generally 0.5 to 5%, by weight. 25 If cerium oxide is to be added at the refinery it may, in fact, be added without anything else. Typically the additives which are incorporated at the refinery include cetane number improvers, cold flow improvers and antioxidants. Accordingly the composition of the present invention can incorporate one or more of these. However since, in general, cerium oxide does not improve the cetane value it is unlikely that it 30 would be added with these.
WO 2004/065529 PCT/GB2004/000294 -7 If the cerium oxide is added at the depot then it can be added alone or with the detergent as well as the other ingredients which are typically added to the fuel at this stage as indicated below. If the cerium oxide is added at the filling station forecourt then similar 5 considerations apply to the depot addition. Typical additives which can be used in the fuel compositions, especially diesel fuel, include those conventionally used, such as: Non polar organic solvents such as aromatic and aliphatic hydrocarbons such as toluene, xylene and white spirit, and mixtures thereof and those sold under 10 the Trade Mark "SHELLSOL" by the Royal Dutch/Shell Group, and "EXXSOL" by ExxonMobil Group. Polar organic solvents, in particular, alcohols generally aliphatic alcohols e.g. 2-ethylhexanol, decanol and isotridecanol, Detergents such as hydrocarbyl-substituted amines and aides, e.g. hydro 15 carbyl-substituted succinimides, e.g. a polyisobutenyl succinimide, Dehazers, e.g. alkoxylated phenol formaldehyde polymers such as those commercially available as "NALCO" (Trade Mark) 7D07 (ex Nalco) , and "TOLAD" (Trade Mark) 2683 (ex Petrolite), Anti-foaming agents e.g. polyether-modified polysiloxanes, commercially 20 available as "TEGOPREN" (Trade Mark) 5851 (ex Th. Goldschmidt) Q 25907 (ex Dow Coming) or "RHODORSIL" (Trade Mark) (ex Rhone Poulenc)) Ignition improvers such as aliphatic nitrates e.g. 2-ethylhexyl nitrate and cyclohexyl nitrate, Anti-rust agents e.g. those sold commercially sold by Rhein 25 Chemie,Mannheim, Germany as "RC 4801 ", or by Ethyl corporation as HiTEC (trade mark) 536, - or polyhydric alcohol esters of succinic acid derivatives Reodorants, Anti-oxidants e.g. phenolics such as 2,6-di-tert-butylphenol, or phenylenediamines such as NN'-di-sec-butyl-p-phenylenediamine, 30 Metal deactivators such as salicylic acid derivatives, e.g. N, N1- WO 2004/065529 PCT/GB2004/000294 -8 disalicylidene-1,2-propane diamine and, Lubricity agents such as polar compounds, especially fatty acids, esters and amides. Typically acids possess a C 2 - C 50 chain and/or are aromatic and include poly basic acids such as dicarboxylic acids, for example a dimer of an unsaturated acid 5 such as oleic or linoleic acid, as well as hydroxy aromatic carboxylic acids, especially with an ortho OH group, for example salicylic acid, especially those which are substituted by a group possessing at least 10 carbon atoms. Typical esters are derived from such acids and an alcohol which is typically a C 1 and C 5 aliphatic alcohol or a polyhydric alcohol such as a glycol, glycerol or pentaerythritol or poly(oxyalkylene) 10 alcohol, e.g. with 5 oxyalkylene groups. The esters of a poly basic acid can be partial. Specific esters include glycerol mono-and di-esters such as glyceryl monooleate, sorbitan monooleate and pentaerythritol monooleate as well as salicylic esters. Other lubricity agents which may be used include esters derived from a carboxyphenol and a polyol and aminoalkyhnorpholines. Some such agents are 15 commercially available as EC831, P631, P633 or P639 (ex Infinium) or "HITEC" (Trade Mark) 580 (ex Ethyl Corporation), TOLAD 2670 and 9103 from Baker Petrolit and those described in WO 98/01516 and 98/16596. Demulsifiers e.g. that commercially available as TOLAD 2898 from Baker Petrolite. Preferred additives include one or more of an anti-foam, demulsifier and an 20 anti-rust agent. Unless otherwise stated, the (active matter) concentration of each additive in the fuel is generally up to 1000 ppmw (parts per million by weight of the diesel fuel), in particular up to 800 ppmw, e.g. 1 to 1000, 1 to 800 or 1-20, ppmw. The (active matter) concentration of the dehazer in the diesel fuel is 25 preferably in the range from 1 to 20ppmw. The (active matter) concentrations of other additives (with the exception of the detergent, ignition improver and the lubricity agent) are each preferably up to 20ppmw. The (active matter) concentration of the detergent is typically up to 800ppmw e.g. 10 to 500 ppmw. The (active matter) concentration of the ignition improver in the diesel fuel is preferably up to 600ppmw 30 e.g. 100 to 250 ppmw. If a lubricity agent is incorporated into the diesel fuel, it is WO 2004/065529 PCT/GB2004/000294 -9 conveniently used in an amount of 50 to 500 ppmw. Some of these additives are more commonly added directly (with the cerium oxide) at the refinery while the others form part of a diesel fuel additive (DFA), typically added at the point of loading with the tanker or at the pump. A typical DFA 5 comprises: detergent 10-70% (by weight) antirust 0-10% antifoam 0-10% dehazer 0-10% 10 non-polar solvent 0-50% polar solvent 0-40% The diesel oil itself may be an additised (additive-containing) oil. If the diesel oil is an additised oil, it will contain minor amounts of one or more additives, e.g. anti-static agents, pipeline drag reducers, flow improvers, e.g. ethylene/vinyl 15 acetate copolymers or acrylate/maleic anhydride copolymers, and wax anti-settling agents, e.g. those commercially available under the Trade Marks "PARAFLOW" (e.g. "PARAFLOW" 450; ex Paramins), "OCTEL" (e.g. "OCTEL" W 5000; ex Octel) and "DODIFLOW" (e.g. "DODIFLOW" V 3958; ex Hoechst). The same or similar additives can be used for other fuels such as petrol, as 20 one skilled in the art will appreciate. The following Example further illustrates the present invention: EXAMPLE The settling of fuel containing cerium oxide alone or with other additives was tested with the following results: 25 1. 2% Cerium Oxide in aliphatic solvent 48.0% Shellsol D70 52.0% Aliphatic solvent Significant solid separation after 24 hrs 30 2. 2% Cerium Oxide in aliphatic solvent 48.0% WO 2004/065529 PCT/GB2004/000294 -10 HiTEC 4620 52.0% aliphatic solvent which contains detergent and antifoam Slight solid separation after 24 hrs 5 3. 2% Cerium Oxide in aliphatic solvent 48.0% BASF Keropur DP403 52.0% aliphatic solvent which contains detergent and antifoam Slight solid separation after 24 hrs 10 4. 2% Cerium Oxide in aliphatic solvent 48.0% Octel DFA 52.0% aliphatic solvent which contains detergent, antifoam and anticorosion agent. No solid separation after 24hrs. 15
Claims (39)
1. A method of improving the efficiency of a fuel for an internal combustion engine which comprises adding to the fuel, prior to the introduction of the fuel to a 5 vehicle or other apparatus comprising an internal combustion engine: (a) cerium oxide and/or doped cerium oxide; and (b) a detergent.
2. A method according to claim 1 wherein one or more additives is further added to the fuel. 10
3. A method according to either of claims 1 or 2 which comprises adding doped cerium oxide which is doped with a divalent or trivalent metal or metalloid which is a rare earth metal, a transition metal or a metal of group IIA, illB, VB or VIB of the Periodic Table.
4. A method according to claim 3 wherein the metal is a transition metal. 15
5. A method according to claim 4 wherein the metal is rhodium, copper, silver, gold, palladium, platinum, iron, manganese, chromium, cobalt, vanadium, zirconium or titanium.
6. A method according to claim 3 wherein the metal is terbium, praeseodymium, samarium, gadolinium, antimony, selenium, gallium, 20 magnesium, beryllium, boron or calcium.
7. A method according to claim I wherein the cerium oxide and/or doped cerium oxide has a size not exceeding 1 micron.
8. A method according to claim 7 wherein the cerium oxide and/or doped cerium oxide has a size from 1 to 300 nm. S:\patricia\cases\2\25895\AU\00\Amended pages DRAFT 770921.doc\\ 12
9. A method according to claim 1 wherein the cerium oxide and/or doped cerium oxide has been coated with an organic acid, anhydride or ester or a Lewis base.
10. A method according to claim 9 wherein the cerium oxide and/or doped 5 cerium oxide has been coated with a dicarboxylic acid anhydride.
11. A method according to claim 10 wherein the cerium oxide and/or doped cerium oxide has been coated with an alkenyl succinic anhydride.
12. A method according to claim 11 wherein the succinic anhydride is dodecenyl succinic anhydride, octadecenyl succinic anhydride or polyisobutenyl 10 succinic anhydride.
13. A method according to claim I wherein the fuel is diesel fuel.
14. A method according to claim 1 wherein the cerium oxide and/or doped cerium oxide is added with a solvent which is an aliphatic or aromatic hydrocarbon or an aliphatic alcohol.
15 15. A method according to claim 1 wherein the cerium oxide and/or doped cerium oxide is added to the fuel at a refinery.
16. A method according to claim I wherein the cerium oxide and/or doped cerium oxide is added at a fuel depot.
17. A method according to claim 1 wherein the cerium oxide and/or doped 20 cerium oxide is added at a filling station forecourt.
18. A method according to claim I wherein the cerium oxide and/or doped cerium oxide is added together with one or more of a detergent, dehazer, anti foaming agent, ignition improver, anti-rust agent, reodorant, anti-oxidant, metal deactivator, lubricity agent or demulsifier. S:\patricia\cases\2\25895\AU\00\Amended pages DRAFT 770921.doc\\ 13
19. A method according to claim 18 wherein the cerium oxide and/or doped cerium oxide is added together with a detergent.
20. A method according to claim 19 wherein the cerium oxide and/or doped cerium oxide is added together with at least one of an anti-foaming agent, 5 demulsifier or anti-rust agent.
21. A method according to claim 1 wherein the cerium oxide and/or doped cerium oxide is added at a concentration not exceeding 20 ppm.
22. A method according to claim 21 wherein the cerium oxide and/or doped cerium oxide is added in an amount not exceeding 10 ppm. 10
23. A fuel additive which comprises cerium oxide and/or doped cerium oxide and a detergent.
24. A fuel additive according to claim 23 wherein the concentration of cerium oxide and/or doped cerium oxide is from 0.1 to 10% by weight.
25. A fuel additive according to claim 24 wherein the concentration of cerium 15 oxide and/or doped cerium oxide is from 0.5 to 5% by weight.
26. A fuel additive according to claim 23 which comprises doped cerium oxide which is doped with a divalent or trivalent metal or metalloid which is a rare earth metal, a transition metal or a metal of group HA, IllB, VB or VIB of the Periodic Table. 20
27. The method according to claim 1 or a fuel additive according to claim 23 wherein the detergent is a basic nitrogen-containing ashless detergent.
28. A method according to claim 1 or a fuel additive according to claim 27 wherein the detergent is a succinimide which has an average of at least 3 nitrogen atoms per molecule. S:\patricia\cases\2\25895\AU\00\Amended pages DRAFT 770921.do\ 14
29. A method or a fuel additive according to claim 28 wherein the succinimide is derived from an alkyl or alkenyl succinic acylating agent having at least 35 carbon atoms in the alkyl or alkenyl part and an alkylene polyamine mixture having an average of at least 3 nitrogen atoms per molecule. 5
30. A method or a fuel additive according to claim 28 wherein the succinimide is derived from a polyisobutenyl succinic acylating agent obtainable from a polyisobutene having a number average molecular weight of 500 to 10,000 and an ethylene polyamine having an average composition from triethylene tetramine to pentaethylene hexamine. 10
31. A method or a fuel additive according to claim 29 wherein the aliphatic chain of the succinimide has a molecular weight of 500 to 2500.
32. A method or a fuel additive according to claim 31 wherein the aliphatic chain of the succinimide has a molecular weight of 750 to 1500.
33. A fuel additive according to claim 23 which also comprises one or more of 15 a dehazer, anti-foaming agent, ignition improver, anti-rust agent, reodorant, anti oxidant, metal deactivator, lubricity agent or demulsifier.
34. A fuel additive according to claim 33 which comprises one or more of an anti-foam agent, an anti-rust agent or a demulsifier.
35. A fuel additive according to claim 23 which comprises a solvent which is an 20 aliphatic or aromatic hydrocarbon or an aliphatic alcohol.
36. A method according to claim 1 wherein the detergent is an amide, amine, Mannich base or succinimide.
37. A method according to claim 36 wherein the detergent is a hydrocarbyl substituted amine or a hydrocarbyl-substituted amide. S:\patricia\cases\2\25895\AU\00\Am ended pages DRAFT 770921.doc\\ 15
38. A fuel additive according to claim 23 wherein the detergent is an amide, amine, Mannich base or succinimide.
39. A fuel additive according to claim 38 wherein the detergent is a hydrocarbyl-substituted amine or a hydrocarbyl-substituted amide. 5 OXONICA LIMITED WATERMARK PATENT AND TRADE MARKS ATTORNEYS P25895AUOO S:\patdca\cases\2\25895\AU\OO\Amended pages DRAFT 770921.doc\\
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0301599.7A GB0301599D0 (en) | 2003-01-23 | 2003-01-23 | Cerium oxide nanoparticles as fuel additives |
GB0301599.7 | 2003-01-23 | ||
PCT/GB2004/000294 WO2004065529A1 (en) | 2003-01-23 | 2004-01-23 | Cerium oxide nanoparticles as fuel additives |
Publications (2)
Publication Number | Publication Date |
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AU2004205788A1 AU2004205788A1 (en) | 2004-08-05 |
AU2004205788B2 true AU2004205788B2 (en) | 2010-09-02 |
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AU2004205788A Expired AU2004205788B2 (en) | 2003-01-23 | 2004-01-23 | Cerium oxide nanoparticles as fuel additives |
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US (1) | US20060254130A1 (en) |
EP (1) | EP1587898A1 (en) |
JP (1) | JP2006516996A (en) |
KR (1) | KR101169804B1 (en) |
CN (1) | CN1764711B (en) |
AU (1) | AU2004205788B2 (en) |
BR (1) | BRPI0406921A (en) |
CA (1) | CA2514146A1 (en) |
GB (1) | GB0301599D0 (en) |
MX (1) | MXPA05007820A (en) |
NZ (1) | NZ541393A (en) |
RU (1) | RU2352618C2 (en) |
WO (1) | WO2004065529A1 (en) |
ZA (1) | ZA200505933B (en) |
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- 2004-01-23 BR BR0406921-8A patent/BRPI0406921A/en not_active Application Discontinuation
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- 2004-01-23 NZ NZ541393A patent/NZ541393A/en not_active IP Right Cessation
- 2004-01-23 CN CN2004800078439A patent/CN1764711B/en not_active Expired - Lifetime
- 2004-01-23 WO PCT/GB2004/000294 patent/WO2004065529A1/en active Application Filing
- 2004-01-23 RU RU2005123391/04A patent/RU2352618C2/en active
- 2004-01-23 JP JP2006500244A patent/JP2006516996A/en active Pending
- 2004-01-23 AU AU2004205788A patent/AU2004205788B2/en not_active Expired
- 2004-01-23 KR KR1020057013595A patent/KR101169804B1/en active IP Right Grant
- 2004-01-23 US US10/542,770 patent/US20060254130A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
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US20060254130A1 (en) | 2006-11-16 |
NZ541393A (en) | 2008-12-24 |
CA2514146A1 (en) | 2004-08-05 |
EP1587898A1 (en) | 2005-10-26 |
CN1764711B (en) | 2010-11-24 |
ZA200505933B (en) | 2006-04-26 |
WO2004065529A1 (en) | 2004-08-05 |
AU2004205788A1 (en) | 2004-08-05 |
JP2006516996A (en) | 2006-07-13 |
KR20060006890A (en) | 2006-01-20 |
BRPI0406921A (en) | 2006-01-03 |
RU2352618C2 (en) | 2009-04-20 |
CN1764711A (en) | 2006-04-26 |
RU2005123391A (en) | 2006-01-27 |
GB0301599D0 (en) | 2003-02-26 |
MXPA05007820A (en) | 2005-10-18 |
KR101169804B1 (en) | 2012-07-30 |
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