CN102196859B - 用于将芳族烃催化气相氧化以得到醛、羧酸和/或羧酸酐,特别是得到邻苯二甲酸酐的催化剂,以及用于制备这种催化剂的方法 - Google Patents
用于将芳族烃催化气相氧化以得到醛、羧酸和/或羧酸酐,特别是得到邻苯二甲酸酐的催化剂,以及用于制备这种催化剂的方法 Download PDFInfo
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- CN102196859B CN102196859B CN200980142796.1A CN200980142796A CN102196859B CN 102196859 B CN102196859 B CN 102196859B CN 200980142796 A CN200980142796 A CN 200980142796A CN 102196859 B CN102196859 B CN 102196859B
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- element oxide
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- 239000003054 catalyst Substances 0.000 title claims abstract description 401
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 25
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 22
- 230000003647 oxidation Effects 0.000 title claims abstract description 21
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 19
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 title claims description 12
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 title abstract description 19
- 150000001735 carboxylic acids Chemical class 0.000 title abstract 2
- 235000019256 formaldehyde Nutrition 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 122
- 239000000725 suspension Substances 0.000 claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 66
- 229910052709 silver Inorganic materials 0.000 claims abstract description 65
- 239000004332 silver Substances 0.000 claims abstract description 65
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 61
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 53
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims abstract description 41
- 239000002243 precursor Substances 0.000 claims abstract description 41
- 239000002994 raw material Substances 0.000 claims abstract description 37
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- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 claims abstract description 20
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- 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 description 4
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- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- JJKXSKYMMKUVNH-UHFFFAOYSA-N C1(=O)OCC2=CC=CC=C12.O1C(CC=C1)=O Chemical compound C1(=O)OCC2=CC=CC=C12.O1C(CC=C1)=O JJKXSKYMMKUVNH-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052946 acanthite Inorganic materials 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Inorganic materials O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 1
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical class [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ORWFSDJNQHQQQD-UHFFFAOYSA-N cerium silicic acid Chemical compound [Ce].[Si](O)(O)(O)O ORWFSDJNQHQQQD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical group C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000012041 precatalyst Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
- 229940056910 silver sulfide Drugs 0.000 description 1
- UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 1
- RAVDHKVWJUPFPT-UHFFFAOYSA-N silver;oxido(dioxo)vanadium Chemical compound [Ag+].[O-][V](=O)=O RAVDHKVWJUPFPT-UHFFFAOYSA-N 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- YEAUATLBSVJFOY-UHFFFAOYSA-N tetraantimony hexaoxide Chemical compound O1[Sb](O2)O[Sb]3O[Sb]1O[Sb]2O3 YEAUATLBSVJFOY-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B01J23/66—Silver or gold
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- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/20—Vanadium, niobium or tantalum
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- B01J23/66—Silver or gold
- B01J23/68—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/682—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium, tantalum or polonium
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- B01J23/683—Silver or gold with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum or tungsten
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- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
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- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
- B01J27/199—Vanadium with chromium, molybdenum, tungsten or polonium
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- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
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- B01J37/02—Impregnation, coating or precipitation
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- B01J37/0219—Coating the coating containing organic compounds
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- B01J37/0228—Coating in several steps
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/08—Formation or introduction of functional groups containing oxygen of carboxyl groups or salts, halides or anhydrides thereof
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
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- 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
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/0009—Use of binding agents; Moulding; Pressing; Powdering; Granulating; Addition of materials ameliorating the mechanical properties of the product catalyst
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- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/08—Heat treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102008044890.7A DE102008044890B4 (de) | 2008-08-29 | 2008-08-29 | Katalysator für die katalytische Gasphasenoxidation von aromatischen Kohlenwasserstoffen zu Aldehyden, Carbonsäuren und/oder Carbonsäureanhydriden, insbesondere zu Phthalsäureanhydrid, sowie Verfahren zur Herstellung eines solchen Katalysators |
DE102008044890.7 | 2008-08-29 | ||
PCT/EP2009/005372 WO2010022830A2 (de) | 2008-08-29 | 2009-07-24 | Katalysator für die katalytische gasphasenoxidation von aromatischen kohlenwasserstoffen zu aldehyden, carbonsäuren und/oder carbonsäureanhydriden, insbesondere zu phthalsäurenanhydrid, sowie verfahren zur herstellung eines solchen katalysators |
Publications (2)
Publication Number | Publication Date |
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CN102196859A CN102196859A (zh) | 2011-09-21 |
CN102196859B true CN102196859B (zh) | 2014-08-06 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN200980142796.1A Active CN102196859B (zh) | 2008-08-29 | 2009-07-24 | 用于将芳族烃催化气相氧化以得到醛、羧酸和/或羧酸酐,特别是得到邻苯二甲酸酐的催化剂,以及用于制备这种催化剂的方法 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP2321045A2 (de) |
KR (1) | KR101706790B1 (de) |
CN (1) | CN102196859B (de) |
BR (1) | BRPI0913160B1 (de) |
DE (1) | DE102008044890B4 (de) |
TW (1) | TWI518079B (de) |
WO (1) | WO2010022830A2 (de) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2501472A1 (de) * | 2009-11-20 | 2012-09-26 | Basf Se | Mehrlagenkatalysator zur herstellung von carbonsäuren und/oder carbonsäureanhydriden mit vanadiumantimonat in wenigstens einer katalysatorlage und verfahren zur herstellung von phthalsäureanhydrid mit niedriger hotspottemperatur |
DE102013202048A1 (de) * | 2013-02-07 | 2013-04-18 | Basf Se | Verfahren zur Herstellung einer katalytisch aktiven Masse, die ein Gemisch aus einem die Elemente Mo und V enthaltenden Multielementoxid und wenigstens einem Oxid des Molybdäns ist |
EP3047904A1 (de) | 2015-01-22 | 2016-07-27 | Basf Se | Katalysatorsystem zur Oxidierung von O-Xylen und/oder Naphthalen zu Phthalsäureanhydrid |
CN107999107A (zh) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | 一种顺酐催化剂及其制备方法和应用 |
DE102017202351A1 (de) * | 2017-02-14 | 2018-08-16 | Clariant International Ltd | Katalysatormaterial zur Oxidation von Kohlenwasserstoffen mit antimondotiertem Titandioxid |
NL2018890B1 (en) * | 2017-05-10 | 2018-11-15 | Admatec Europe B V | Additive manufacturing of metal objects |
CN109110910A (zh) * | 2018-08-31 | 2019-01-01 | 江苏新亿源环保科技有限公司 | 一种高催化性悬浮梯级生物滤料的制备方法 |
CN109158119A (zh) * | 2018-09-14 | 2019-01-08 | 中海油天津化工研究设计院有限公司 | 一种用于均四甲苯氧化的催化剂及制备方法 |
CN109369544B (zh) * | 2018-12-05 | 2022-06-03 | 兰州大学 | 一种催化氧化制备5-甲基吡嗪-2-羧酸的方法 |
CN114100651B (zh) * | 2020-08-25 | 2023-12-08 | 中国石油化工股份有限公司 | 一种苯氧化制顺酐催化剂及其制备方法和应用 |
CN114539207B (zh) * | 2020-11-24 | 2023-09-19 | 万华化学(四川)有限公司 | 一种制备丙交酯的方法及催化剂 |
CN114682278B (zh) * | 2020-12-29 | 2023-09-01 | 中国石油化工股份有限公司 | 一种抗失磷钒磷氧催化剂 |
IT202100021746A1 (it) | 2021-08-11 | 2023-02-11 | Polynt S P A | Letto catalitico multistrato per la produzione di anidride ftalica. |
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EP0522871A1 (de) * | 1991-07-10 | 1993-01-13 | Nippon Shokubai Co., Ltd. | Katalysator und Verfahren zur Herstellung von Phtalsäureanhydrid |
CN1938086A (zh) * | 2004-03-26 | 2007-03-28 | 巴斯福股份公司 | 具有银-钒氧化物相和助催化剂相的催化剂 |
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KR20110050694A (ko) | 2011-05-16 |
DE102008044890B4 (de) | 2023-09-14 |
BRPI0913160A2 (pt) | 2016-07-26 |
WO2010022830A2 (de) | 2010-03-04 |
TWI518079B (zh) | 2016-01-21 |
EP2321045A2 (de) | 2011-05-18 |
DE102008044890A1 (de) | 2010-03-04 |
CN102196859A (zh) | 2011-09-21 |
BRPI0913160B1 (pt) | 2018-03-27 |
WO2010022830A3 (de) | 2010-05-20 |
KR101706790B1 (ko) | 2017-02-15 |
TW201012805A (en) | 2010-04-01 |
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