RU2006124865A - Композитный катализатор для селективной олигомеризации низших алкенов и получения высокооктановых продуктов - Google Patents
Композитный катализатор для селективной олигомеризации низших алкенов и получения высокооктановых продуктов Download PDFInfo
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- RU2006124865A RU2006124865A RU2006124865/04A RU2006124865A RU2006124865A RU 2006124865 A RU2006124865 A RU 2006124865A RU 2006124865/04 A RU2006124865/04 A RU 2006124865/04A RU 2006124865 A RU2006124865 A RU 2006124865A RU 2006124865 A RU2006124865 A RU 2006124865A
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- Prior art keywords
- catalytic
- alkene
- catalytic composite
- filling material
- distillation
- Prior art date
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- 239000002131 composite material Substances 0.000 title claims 41
- 239000003054 catalyst Substances 0.000 title claims 21
- -1 LOW ALKENES Chemical class 0.000 title claims 4
- 238000006384 oligomerization reaction Methods 0.000 title claims 3
- 230000003197 catalytic effect Effects 0.000 claims 76
- 238000004821 distillation Methods 0.000 claims 42
- 238000000034 method Methods 0.000 claims 38
- 239000000463 material Substances 0.000 claims 22
- 150000001336 alkenes Chemical class 0.000 claims 21
- 229910052751 metal Inorganic materials 0.000 claims 12
- 239000002184 metal Substances 0.000 claims 12
- 238000005984 hydrogenation reaction Methods 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- RGYAVZGBAJFMIZ-UHFFFAOYSA-N 2,3-dimethylhex-2-ene Chemical group CCCC(C)=C(C)C RGYAVZGBAJFMIZ-UHFFFAOYSA-N 0.000 claims 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052809 inorganic oxide Inorganic materials 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 239000013543 active substance Substances 0.000 claims 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 5
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- WEPNJTDVIIKRIK-UHFFFAOYSA-N 2-methylhept-2-ene Chemical compound CCCCC=C(C)C WEPNJTDVIIKRIK-UHFFFAOYSA-N 0.000 claims 2
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical group CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical class CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims 2
- 229910052703 rhodium Inorganic materials 0.000 claims 2
- 239000010948 rhodium Substances 0.000 claims 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 2
- FLTJDUOFAQWHDF-UHFFFAOYSA-N trimethyl pentane Natural products CCCCC(C)(C)C FLTJDUOFAQWHDF-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000004254 Ammonium phosphate Substances 0.000 claims 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 1
- 229910021536 Zeolite Inorganic materials 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 claims 1
- 235000019289 ammonium phosphates Nutrition 0.000 claims 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims 1
- 235000011130 ammonium sulphate Nutrition 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000004523 catalytic cracking Methods 0.000 claims 1
- 150000004696 coordination complex Chemical class 0.000 claims 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims 1
- 238000006471 dimerization reaction Methods 0.000 claims 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910001463 metal phosphate Inorganic materials 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical group Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical group [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 claims 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
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- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/10—Catalytic processes with metal oxides
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- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
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- C10G11/00—Catalytic cracking, in the absence of hydrogen, of hydrocarbon oils
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Claims (47)
1. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции, где указанный каталитический композит включает
а) поддерживающую структуру, выполненную из неорганического оксида, отличного от цеолита, который имеет свободную фракцию в диапазоне от 0,30 до 0,95 и площадь поверхности от 40 до 500 м2/г, где указанная поддерживающая структура имеет форму, выбранную из кольца, полого цилиндра, крестообразного или многораздельного кольца или цилиндра, содержащего 2, 3 или 4 секции, седла, сплошного кольца, сплошного цилиндра, сферы и структуры пчелиных сот;
b) от 0,01 до 10 мас.% каталитически активного вещества, включающего металл из группы VIII, относительно веса каталитического композита, который наносится на поддерживающую структуру.
2. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанная свободная фракция составляет от 0,30 до 0,95, а площадь поверхности составляет от 50 до 500 м2/г.
3. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1 или 2, отличающийся тем, что указанный неорганический оксид выбирают из глинозема, кремнезема, оксида титана, оксида циркония и их смесей.
4. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1 или 2, отличающийся тем, что указанный неорганический оксид представляет собой γ-окись алюминия.
5. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1 или 2, отличающийся тем, что указанный неорганический оксид представляет собой α-окись алюминия.
6. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанная поддерживающая структура имеет форму кольца Рашига.
7. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанный металл из группы VIII представляет собой никель.
8. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанный металл из группы VIII имеет вид соли металла или комплекса металла.
9. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.8, отличающийся тем, что указанная соль металла находится в ионизированном состоянии.
10. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.8, отличающийся тем, что указанная соль металла представляет собой сульфат металла, фосфат металла, оксалат металла или ацетат металла.
11. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанное каталитически активное вещество представляет собой сульфат никеля.
12. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанное каталитически активное вещество представляет собой хлорид никеля.
13. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.7, отличающийся тем, что указанное каталитически активное вещество представляет смесь с сульфатом аммония или фосфатом аммония.
14. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанное каталитически активное вещество включает металл из группы VIII и лиганд, где указанный лиганд включает один или несколько атомов, выбранных из группы, состоящей из атома углерода, водорода, кислорода, азота и фосфора.
15. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.14, отличающийся тем, что указанный металл из группы VIII находится в состоянии нулевого окисления.
16. Каталитический композит для использования в качестве заполняющего в случайном режиме материала и катализатора в аппарате для каталитической дистилляции по п.1, отличающийся тем, что указанный металл из группы VIII представляет собой палладий, платину или родий.
17. Способ селективной димеризации низшего алкена до С6-С12 алкена, отличающийся тем, что указанный способ включает приведение в контакт низшего алкена с каталитическим композитом по любому из пп.1-16 в условиях каталитической дистилляции.
18. Способ по п.17, отличающийся тем, что указанный низший алкен выбирают из 1-бутена, 2-бутена и изобутена, а С6-С12 алкен выбирают из триметилпентена, н-октена, диметилгексена и метилгептена.
19. Способ по п.17 или 18, отличающийся тем, что указанный каталитический композит смешивают с инертным заполняющим материалом для дистилляции.
20. Способ по п.19, отличающийся тем, что соотношение каталитического композита и инертного заполняющего материала для дистилляции составляет от 10:1 до 1:10.
21. Способ по п.19, отличающийся тем, что каталитический композит и инертный заполняющий материал для дистилляции используют в отдельных зонах каталитической дистилляционной колонки.
22. Способ по п.17, отличающийся тем, что указанный низший алкен представляет собой С4 алкен, а С6-С12 алкен представляет собой преимущественно С8 алкен.
23. Способ по п.22, отличающийся тем, что С8 алкен представляет собой триметилпентен.
24. Способ гидрогенизации алкена до алкана, отличающийся тем, что указанный способ включает приведение в контакт указанного алкена с каталитическим композитом по любому из пп.14-16 и водородом, в условиях каталитической дистилляции.
25. Способ по п.24, отличающийся тем, что указанный алкен выбирают из триметилпентена, н-октена, диметилгексена и метилгептена.
26. Способ по п.24 или 25, отличающийся тем, что указанный каталитический композит смешивают с инертным заполняющим материалом для дистилляционной колонки.
27. Способ по п.26, отличающийся тем, что соотношение каталитического композита и инертного заполняющего материала для дистилляции составляет от 10:1 до 1:10.
28. Способ по п.26, отличающийся тем, что каталитический композит и инертный заполняющий материал для дистилляции используют в отдельных зонах каталитической дистилляционной колонки.
29. Способ по любому из пп.24-25, отличающийся тем, что указанный алкен представляет собой триметилпентен, а алкан представляет собой триметилпентан.
30. Способ получения высокооктановых соединений, включающий
а) приведение в контакт С2-С6 алкена с каталитическим композитом по любому из пп.1-16 в условиях каталитической дистилляции, с получением С6-С18 алкена и
b) приведение в контакт С6-С18 алкена со стадии а) с каталитическим композитом по любому из пп.14-16 и водородом в условиях каталитической дистилляции, с получением С6-С18 алкана.
31. Способ по п.30, отличающийся тем, что стадии а) и b) указанного процесса проводят в одной колонке для каталитической дистилляции.
32. Способ по п.30, отличающийся тем, что стадии а) и b) указанного процесса проводят в отдельных колонках для каталитической дистилляции.
33. Способ по п.30 или 31, отличающийся тем, что С2-С6 алкен представляет собой С4 алкен, а С6-С18 алкен представляет собой С8 алкен.
34. Способ по п.33, отличающийся тем, что С8 алкен представляет собой триметилпентен.
35. Способ получения высокооктановых соединений, включающий
а) приведение в контакт изобутена с каталитическим композитом по любому из пп.1-16 в условиях каталитической дистилляции, с получением триметилпентена и
b) приведение в контакт триметилпентена с катализатором гидрогенизации и водородом в условиях периодической реакции или в условиях реакции гидрогенизации, с получением триметилпентана.
36. Способ получения С6-С18 алкенов, отличающийся тем, что указанный способ включает приведение в контакт смеси С2-С6 алкенов с каталитическим композитом по любому из пп.1-16 в условиях каталитической дистилляции.
37. Способ по п.36, в соответствии с которым каждый С2-С6 алкен в смеси подвергается олигомеризации в разных реакционных зонах, находящихся в пределах одной колонки для каталитической дистилляции.
38. Способ по п.36, в соответствии с которым каждый С2-С6 алкен подвергается олигомеризации в разных реакционных зонах, находящихся в двух или более соединенных колонках для каталитической дистилляции.
39. Способ по любому из пп.36-38, отличающийся тем, что смесь С2-С6 алкенов включает один или несколько С4 алкенов.
40. Способ селективной олигомеризации низшего алкена до С6-С18 алкена, отличающийся тем, что указанный способ включает приведение в контакт смеси С2-С6 алкенов и С1-С6 алканов с каталитическим композитом по любому из пп.1-16 в условиях каталитической дистилляции.
41. Каталитический композит для использования в качестве вносимого в случайном режиме катализатора гидрогенизации в аппарат для каталитической дистилляции, где указанный каталитический композит включает
а) поддерживающую структуру, выполненную из неорганического оксида, которая имеет свободную фракцию в диапазоне от 0,30 до 0,95, где указанная поддерживающая структура имеет форму, выбранную из кольца, полого цилиндра, крестообразного или многораздельного кольца или цилиндра, содержащего 2, 3 или 4 секции, седла, сплошного кольца, сплошного цилиндра, сферы и структуры пчелиных сот;
b) от 0,01 до 10 мас.% палладия, платины или родия, относительно веса каталитического композита, которые наносятся на поддерживающую структуру.
42. Каталитический композит для использования в качестве вносимого в случайном режиме катализатора гидрогенизации в аппарат для каталитической дистилляции по п.41, отличающийся тем, что указанный неорганический оксид представляет собой α-глинозем.
43. Каталитический композит для использования в качестве вносимого в случайном режиме катализатора гидрогенизации в аппарат для каталитической дистилляции по п.42, в котором α-глинозем имеет площадь поверхности от 0,1 до 1,0 м2/г.
44. Способ гидрогенизации бутадиена, отличающийся тем, что указанный способ включает приведение в контакт бутадиена с каталитическим композитом по любому из пп.41-43 и водородом в условиях каталитической дистилляции.
45. Способ селективной гидрогенизации метилацетилена и пропадиена в С3 фракции с получением пропилена, отличающийся тем, что указанный способ включает приведение в контакт С3 фракции с каталитическим композитом по любому из пп.41-43 и водородом в условиях каталитической дистилляции.
46. Способ селективной гидрогенизации аллена и пропина в потоке жидкостного каталитического крекинга (FCC), отличающийся тем, что указанный способ включает приведение в контакт потока FCC с каталитическим композитом по любому из пп.41-43 и водородом в условиях каталитической дистилляции.
47. Способ селективной гидрогенизации бутадиена в потоке раффината I или раффината II с получением бутена, отличающийся тем, что указанный способ включает приведение в контакт потока раффината I или раффината II с каталитическим композитом по любому из пп.41-43 и водородом в условиях каталитической дистилляции.
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-
2004
- 2004-12-10 JP JP2006543337A patent/JP2007513753A/ja active Pending
- 2004-12-10 BR BRPI0416855-0A patent/BRPI0416855A/pt not_active Application Discontinuation
- 2004-12-10 CN CN2004800401177A patent/CN1902144B/zh not_active Expired - Fee Related
- 2004-12-10 ZA ZA200605251A patent/ZA200605251B/en unknown
- 2004-12-10 WO PCT/CA2004/002111 patent/WO2005056503A1/en active Application Filing
- 2004-12-10 US US10/582,333 patent/US7718569B2/en not_active Expired - Fee Related
- 2004-12-10 EP EP04802288A patent/EP1697282A1/en not_active Withdrawn
- 2004-12-10 CA CA2548429A patent/CA2548429C/en not_active Expired - Fee Related
- 2004-12-10 RU RU2006124865/04A patent/RU2006124865A/ru not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
US7718569B2 (en) | 2010-05-18 |
WO2005056503A1 (en) | 2005-06-23 |
CN1902144B (zh) | 2010-06-09 |
BRPI0416855A (pt) | 2007-02-27 |
CN1902144A (zh) | 2007-01-24 |
JP2007513753A (ja) | 2007-05-31 |
EP1697282A1 (en) | 2006-09-06 |
US20070123743A1 (en) | 2007-05-31 |
ZA200605251B (en) | 2007-11-28 |
CA2548429A1 (en) | 2005-06-23 |
CA2548429C (en) | 2012-12-04 |
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