DK2150557T3 - Product containing monomer and polymers of titanyler and processes for their preparation. - Google Patents
Product containing monomer and polymers of titanyler and processes for their preparation. Download PDFInfo
- Publication number
- DK2150557T3 DK2150557T3 DK08825898.3T DK08825898T DK2150557T3 DK 2150557 T3 DK2150557 T3 DK 2150557T3 DK 08825898 T DK08825898 T DK 08825898T DK 2150557 T3 DK2150557 T3 DK 2150557T3
- Authority
- DK
- Denmark
- Prior art keywords
- substituted
- group
- compound
- formula
- unsubstituted
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 53
- 230000008569 process Effects 0.000 title claims description 40
- 229920000642 polymer Polymers 0.000 title description 11
- 238000002360 preparation method Methods 0.000 title description 9
- 239000000178 monomer Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 119
- 239000000203 mixture Substances 0.000 claims description 58
- -1 CH3-xClxCO2H Chemical compound 0.000 claims description 57
- 239000000446 fuel Substances 0.000 claims description 41
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 230000001590 oxidative effect Effects 0.000 claims description 38
- 239000007800 oxidant agent Substances 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 239000011593 sulfur Substances 0.000 claims description 31
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium(II) oxide Chemical compound [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 18
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 150000007524 organic acids Chemical class 0.000 claims description 16
- 229910052719 titanium Inorganic materials 0.000 claims description 16
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 15
- 239000000356 contaminant Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 150000004965 peroxy acids Chemical class 0.000 claims description 11
- 239000002952 polymeric resin Substances 0.000 claims description 11
- 229920003002 synthetic resin Polymers 0.000 claims description 11
- 229910052726 zirconium Inorganic materials 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003502 gasoline Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000001451 organic peroxides Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- 239000010779 crude oil Substances 0.000 claims description 3
- 229910052735 hafnium Inorganic materials 0.000 claims description 3
- 239000002283 diesel fuel Substances 0.000 claims description 2
- PFAMAECSGCJQNP-QHWCQOHYSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;oxotitanium Chemical compound [Ti]=O.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO PFAMAECSGCJQNP-QHWCQOHYSA-N 0.000 claims 2
- XHAKVIIVGMQSJX-SNQWTSQPSA-N O=[Ti++].OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO Chemical compound O=[Ti++].OC[C@H](O)[C@H](O)CO.OC[C@H](O)[C@H](O)CO XHAKVIIVGMQSJX-SNQWTSQPSA-N 0.000 claims 2
- UVSKOLBZAFWYOZ-UHFFFAOYSA-N oxotitanium;propane-1,2,3-triol Chemical compound [Ti]=O.OCC(O)CO.OCC(O)CO UVSKOLBZAFWYOZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 67
- 239000003054 catalyst Substances 0.000 description 49
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 35
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 26
- 239000000463 material Substances 0.000 description 23
- 235000011187 glycerol Nutrition 0.000 description 22
- 239000002904 solvent Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 18
- 238000007254 oxidation reaction Methods 0.000 description 18
- 239000010936 titanium Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 230000003647 oxidation Effects 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 14
- 239000002245 particle Substances 0.000 description 14
- 150000003077 polyols Chemical class 0.000 description 14
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 13
- 239000002105 nanoparticle Substances 0.000 description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 238000006477 desulfuration reaction Methods 0.000 description 11
- 230000023556 desulfurization Effects 0.000 description 11
- 229940093476 ethylene glycol Drugs 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 150000003457 sulfones Chemical class 0.000 description 9
- 150000003464 sulfur compounds Chemical class 0.000 description 9
- 239000004408 titanium dioxide Substances 0.000 description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 8
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 8
- 239000004386 Erythritol Substances 0.000 description 8
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 8
- 229940009714 erythritol Drugs 0.000 description 8
- 235000019414 erythritol Nutrition 0.000 description 8
- 238000007429 general method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000600 sorbitol Substances 0.000 description 8
- 235000010356 sorbitol Nutrition 0.000 description 8
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 8
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- MYAQZIAVOLKEGW-UHFFFAOYSA-N 4,6-dimethyldibenzothiophene Chemical compound S1C2=C(C)C=CC=C2C2=C1C(C)=CC=C2 MYAQZIAVOLKEGW-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 150000004703 alkoxides Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000012530 fluid Substances 0.000 description 6
- 238000005755 formation reaction Methods 0.000 description 6
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 101000955037 Homo sapiens Homeobox protein MOX-2 Proteins 0.000 description 5
- 101001098352 Homo sapiens OX-2 membrane glycoprotein Proteins 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 102100021874 NADPH oxidase 3 Human genes 0.000 description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- XFVGXQSSXWIWIO-UHFFFAOYSA-N chloro hypochlorite;titanium Chemical compound [Ti].ClOCl XFVGXQSSXWIWIO-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 239000006066 glass batch Substances 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 241000894007 species Species 0.000 description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 5
- NICUQYHIOMMFGV-UHFFFAOYSA-N 4-Methyldibenzothiophene Chemical compound S1C2=CC=CC=C2C2=C1C(C)=CC=C2 NICUQYHIOMMFGV-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000012296 anti-solvent Substances 0.000 description 4
- 230000002051 biphasic effect Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229960005150 glycerol Drugs 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 238000000066 reactive distillation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 4
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012963 UV stabilizer Substances 0.000 description 3
- 150000001298 alcohols Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005202 decontamination Methods 0.000 description 3
- 230000003588 decontaminative effect Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical group 0.000 description 3
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 3
- 239000003495 polar organic solvent Substances 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- 239000004034 viscosity adjusting agent Substances 0.000 description 3
- OXIKLRTYAYRAOE-CMDGGOBGSA-N (e)-3-(1-benzyl-3-pyridin-3-ylpyrazol-4-yl)prop-2-enoic acid Chemical compound N1=C(C=2C=NC=CC=2)C(/C=C/C(=O)O)=CN1CC1=CC=CC=C1 OXIKLRTYAYRAOE-CMDGGOBGSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- DGUACJDPTAAFMP-UHFFFAOYSA-N 1,9-dimethyldibenzo[2,1-b:1',2'-d]thiophene Natural products S1C2=CC=CC(C)=C2C2=C1C=CC=C2C DGUACJDPTAAFMP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
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- 230000001681 protective effect Effects 0.000 description 1
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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- 230000008022 sublimation Effects 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/003—Compounds containing elements of Groups 4 or 14 of the Periodic Table without C-Metal linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
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| US92421407P | 2007-05-03 | 2007-05-03 | |
| US91717107P | 2007-05-10 | 2007-05-10 | |
| US3961908P | 2008-03-26 | 2008-03-26 | |
| PCT/US2008/005624 WO2008153633A2 (en) | 2007-05-03 | 2008-05-02 | Product containing monomer and polymers of titanyls and methods for making same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2150557T3 true DK2150557T3 (en) | 2016-08-29 |
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| CA (2) | CA2685850C (https=) |
| DE (1) | DE08825898T1 (https=) |
| DK (1) | DK2150557T3 (https=) |
| ES (1) | ES2345705T3 (https=) |
| PL (1) | PL2150557T3 (https=) |
| WO (1) | WO2008153633A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2472841C2 (ru) * | 2008-03-26 | 2013-01-20 | Отерра, Инк. | Катализаторы сульфоокисления и способы и системы их применения |
| US9061273B2 (en) * | 2008-03-26 | 2015-06-23 | Auterra, Inc. | Sulfoxidation catalysts and methods and systems of using same |
| JP5858406B2 (ja) * | 2010-05-10 | 2016-02-10 | 学校法人 関西大学 | 硬化性組成物、これを用いたエポキシ樹脂−無機ポリマー複合材料の製造方法及びエポキシ樹脂−無機ポリマー複合材料 |
| BR112013001539A2 (pt) * | 2010-07-20 | 2016-07-19 | Auterra Inc | "dessulfurização oxidativa por meio do uso de um catalisador de titânio (iv) e hidropreróxidos orgânicos" |
| US9828557B2 (en) | 2010-09-22 | 2017-11-28 | Auterra, Inc. | Reaction system, methods and products therefrom |
| US20120286435A1 (en) * | 2011-03-04 | 2012-11-15 | Ppg Industries Ohio, Inc. | Process for preparing molded optical articles |
| CN105001254B (zh) * | 2011-09-05 | 2018-09-11 | 东曹株式会社 | 制膜用材料、iv族金属氧化物膜的制造方法 |
| CN102593371A (zh) * | 2012-03-16 | 2012-07-18 | 四川长虹电器股份有限公司 | 有机电致发光器件的封装结构 |
| EP2763142A1 (de) | 2013-02-04 | 2014-08-06 | Siemens Aktiengesellschaft | Imprägnierharz für einen Elektroisolationskörper, Elektroisolationskörper und Verfahren zum Herstellen des Elektroisolationskörpers |
| WO2016154529A1 (en) * | 2015-03-26 | 2016-09-29 | Auterra, Inc. | Adsorbents and methods of use |
| US10450516B2 (en) | 2016-03-08 | 2019-10-22 | Auterra, Inc. | Catalytic caustic desulfonylation |
| CN106881073A (zh) * | 2016-05-20 | 2017-06-23 | 上海依瓦达环境技术有限公司 | 一种用于空气净化的光催化剂涂层结构及其制备方法 |
| EP3768794B1 (en) | 2018-03-22 | 2021-04-28 | 3M Innovative Properties Company | Charge-modified particles and methods of making the same |
| US11046894B2 (en) | 2018-08-31 | 2021-06-29 | Amin Bazyari | Mixed oxide nanocomposite catalyst-adsorbent for oxidative desulfurization of liquid hydrocarbon fuels |
| CN111822046B (zh) * | 2020-06-30 | 2023-03-10 | 广州美晨科技实业有限公司 | 一种司盘系列产品及其制备方法 |
| JPWO2022065127A1 (https=) * | 2020-09-24 | 2022-03-31 | ||
| JPWO2022265028A1 (https=) * | 2021-06-18 | 2022-12-22 |
Family Cites Families (140)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE520661A (https=) | 1952-06-18 | |||
| US2789134A (en) | 1953-06-19 | 1957-04-16 | Exxon Research Engineering Co | Recovery of naphthenic acids |
| US2910434A (en) | 1955-05-24 | 1959-10-27 | Texaco Inc | Process for removing trace metals with hydrogen and an inert packing material |
| US2987470A (en) | 1958-11-13 | 1961-06-06 | Hydrocarbon Research Inc | Demineralization of oils |
| FR1299736A (fr) | 1961-06-23 | 1962-07-27 | Exxon Research Engineering Co | Purification des huiles dérivées d'hydrocarbures |
| NL285285A (https=) | 1961-11-10 | |||
| US3164545A (en) | 1962-12-26 | 1965-01-05 | Exxon Research Engineering Co | Desulfurization process |
| NL6602260A (https=) | 1965-02-23 | 1966-08-24 | ||
| US3558747A (en) | 1967-01-30 | 1971-01-26 | Ethyl Corp | Dihydrocarbylhydroxyphenyl phosphorus-containing antioxidants |
| US3565793A (en) | 1968-12-27 | 1971-02-23 | Texaco Inc | Desulfurization with a catalytic oxidation step |
| US3668117A (en) | 1970-03-17 | 1972-06-06 | Texaco Inc | Desulfurization of a preoxidized oil |
| US3847797A (en) | 1971-10-05 | 1974-11-12 | Exxon Research Engineering Co | Visbreaking a heavy hydrocarbon feedstock in a regenerable molten medium |
| US3819509A (en) | 1971-11-26 | 1974-06-25 | Hydrocarbon Research Inc | Low sulfur fuel oil from high metals containing petroleum residuum |
| US3964995A (en) | 1972-07-24 | 1976-06-22 | Hydrocarbon Research, Inc. | Hydrodesulfurization process |
| JPS5139645B2 (https=) | 1972-12-30 | 1976-10-29 | ||
| US3948759A (en) | 1973-03-28 | 1976-04-06 | Exxon Research And Engineering Company | Visbreaking a heavy hydrocarbon feedstock in a regenerable molten medium in the presence of hydrogen |
| US3926604A (en) | 1974-02-19 | 1975-12-16 | Glass Container Manufacturers | Method for applying an inorganic titanium coating to a glass surface |
| US3960708A (en) | 1974-05-31 | 1976-06-01 | Standard Oil Company | Process for upgrading a hydrocarbon fraction |
| US3960706A (en) | 1974-05-31 | 1976-06-01 | Standard Oil Company | Process for upgrading a hydrocarbon fraction |
| US3945914A (en) | 1974-08-23 | 1976-03-23 | Atlantic Richfield Company | Process for "sulfur reduction of an oxidized hydrocarbon by forming a metal-sulfur-containing compound" |
| US4003823A (en) | 1975-04-28 | 1977-01-18 | Exxon Research And Engineering Company | Combined desulfurization and hydroconversion with alkali metal hydroxides |
| US4119528A (en) | 1977-08-01 | 1978-10-10 | Exxon Research & Engineering Co. | Hydroconversion of residua with potassium sulfide |
| US4127470A (en) | 1977-08-01 | 1978-11-28 | Exxon Research & Engineering Company | Hydroconversion with group IA, IIA metal compounds |
| US4192736A (en) | 1978-11-29 | 1980-03-11 | Chevron Research Company | Removal of indigenous metal impurities from an oil with phosphorus oxide-promoted alumina |
| JPS55104920A (en) | 1979-01-30 | 1980-08-11 | Nippon Mining Co Ltd | Manufacture of lightened oil and hydrogen from heavy oil |
| JPS601056B2 (ja) | 1980-02-19 | 1985-01-11 | 千代田化工建設株式会社 | アスファルテンを含む重質炭化水素油の水素化処理 |
| US4374949A (en) | 1980-10-27 | 1983-02-22 | The Goodyear Tire & Rubber Company | Composition and process for making a green colored polyester |
| JPS5874693A (ja) * | 1981-10-29 | 1983-05-06 | Nippon Soda Co Ltd | 複合オキシアルコキシド誘導体及びその製造法 |
| US4591426A (en) | 1981-10-08 | 1986-05-27 | Intevep, S.A. | Process for hydroconversion and upgrading of heavy crudes of high metal and asphaltene content |
| US4437980A (en) | 1982-07-30 | 1984-03-20 | Rockwell International Corporation | Molten salt hydrotreatment process |
| US4665261A (en) | 1985-06-21 | 1987-05-12 | Atlantic Richfield Company | Hydrocarbon conversion process using a molten salt |
| US4645589A (en) | 1985-10-18 | 1987-02-24 | Mobil Oil Corporation | Process for removing metals from crude |
| US5166118A (en) | 1986-10-08 | 1992-11-24 | Veba Oel Technologie Gmbh | Catalyst for the hydrogenation of hydrocarbon material |
| DE3635532A1 (de) | 1986-10-18 | 1988-04-28 | Philips Patentverwaltung | Verfahren zur herstellung von bariumtitanat batio(pfeil abwaerts)3(pfeil abwaerts) |
| US4944936A (en) | 1987-04-10 | 1990-07-31 | Kemira, Inc. | Titanium dioxide with high purity and uniform particle size and method therefore |
| DE3737370C1 (de) | 1987-11-04 | 1989-05-18 | Veba Oel Entwicklungs Gmbh | Verfahren zur hydrierenden Konversion von Schwer- und Rueckstandsoelen,Alt- und Abfalloelen in Mischung mit Klaerschlaemmen |
| JPH01172390A (ja) * | 1987-12-28 | 1989-07-07 | Hokko Chem Ind Co Ltd | 金属アルコキシドの製造方法 |
| GB2226024B (en) * | 1988-12-16 | 1992-06-10 | Tioxide Group Plc | Organo-metallic compounds |
| US4923682A (en) * | 1989-03-30 | 1990-05-08 | Kemira, Inc. | Preparation of pure titanium dioxide with anatase crystal structure from titanium oxychloride solution |
| US5637739A (en) | 1990-03-21 | 1997-06-10 | Research Corporation Technologies, Inc. | Chiral catalysts and catalytic epoxidation catalyzed thereby |
| US5171727A (en) | 1991-08-26 | 1992-12-15 | Uop | Method of preparing a catalyst for the hydroconversion of asphaltene-containing hydrocarbonaceous charge stocks |
| JP3337311B2 (ja) * | 1994-03-11 | 2002-10-21 | 高砂香料工業株式会社 | 新規オキソ−チタン錯体、その製造方法およびその錯体を用いたβ−ヒドロキシケトンまたはα−ヒドロキシカルボン酸エステルの製造方法 |
| US5783165A (en) | 1997-01-08 | 1998-07-21 | Ferro Corporation | Method of making barium titanate |
| US6160193A (en) | 1997-11-20 | 2000-12-12 | Gore; Walter | Method of desulfurization of hydrocarbons |
| US6245223B1 (en) | 1997-12-16 | 2001-06-12 | Exxonmobil Research And Engineering Company | Selective adsorption process for resid upgrading (law815) |
| US6087662A (en) | 1998-05-22 | 2000-07-11 | Marathon Ashland Petroleum Llc | Process for analysis of asphaltene content in hydrocarbon mixtures by middle infrared spectroscopy |
| KR100277164B1 (ko) | 1998-07-16 | 2001-01-15 | 장인순 | 저온균질침전법을이용한사염화티타늄수용액으로부터의결정성tio₂초미립분말의제조방법 |
| US7171368B1 (en) | 1998-12-24 | 2007-01-30 | Pitney Bowes Inc. | Method and apparatus for the remote inspection of postage meters |
| US6368495B1 (en) | 1999-06-07 | 2002-04-09 | Uop Llc | Removal of sulfur-containing compounds from liquid hydrocarbon streams |
| AU764159B2 (en) | 1999-07-01 | 2003-08-14 | E.I. Du Pont De Nemours And Company | A process for controlling the passivation of aluminum chloride formed in the chlorination of titanium-containing ores |
| US6403526B1 (en) | 1999-12-21 | 2002-06-11 | W. R. Grace & Co.-Conn. | Alumina trihydrate derived high pore volume, high surface area aluminum oxide composites and methods of their preparation and use |
| US6471852B1 (en) | 2000-04-18 | 2002-10-29 | Exxonmobil Research And Engineering Company | Phase-transfer catalyzed destruction of fouling agents in petroleum streams |
| EA200201127A1 (ru) | 2000-04-24 | 2003-06-26 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Извлечение углеводородов на месте залегания из керогенсодержащей формации |
| US6402940B1 (en) | 2000-09-01 | 2002-06-11 | Unipure Corporation | Process for removing low amounts of organic sulfur from hydrocarbon fuels |
| ES2179753B1 (es) | 2000-10-11 | 2005-02-16 | Universidad Politecnica De Valencia | Proceso y catalizadores para la eliminacion de compuestos de azufre de la fraccion gasolina. |
| US6547957B1 (en) | 2000-10-17 | 2003-04-15 | Texaco, Inc. | Process for upgrading a hydrocarbon oil |
| FR2818990B1 (fr) | 2000-12-28 | 2004-09-24 | Total Raffinage Distribution | Procede et dispositif de desulfuration d'hydrocarbures charges en derives thiopheniques |
| US6867275B2 (en) | 2001-03-30 | 2005-03-15 | Rohm And Haas Company | Solid media |
| ES2183710B1 (es) | 2001-04-12 | 2004-01-16 | Univ Valencia Politecnica | Proceso y catalizadores para la eliminacion de compuestos de azufre de la fraccion diesel. |
| US6544409B2 (en) | 2001-05-16 | 2003-04-08 | Petroleo Brasileiro S.A. - Petrobras | Process for the catalytic oxidation of sulfur, nitrogen and unsaturated compounds from hydrocarbon streams |
| US6841062B2 (en) | 2001-06-28 | 2005-01-11 | Chevron U.S.A. Inc. | Crude oil desulfurization |
| EP1422198A4 (en) | 2001-07-27 | 2004-09-08 | Chiyoda Chem Eng Construct Co | POROUS OXIDE OF A GROUP 4 METAL AND METHOD FOR THE PRODUCTION THEREOF |
| US6579472B2 (en) * | 2001-07-27 | 2003-06-17 | The Boeing Company | Corrosion inhibiting sol-gel coatings for metal alloys |
| US6673236B2 (en) | 2001-08-29 | 2004-01-06 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Natural Resources | Method for the production of hydrocarbon fuels with ultra-low sulfur content |
| AU2002329986A1 (en) | 2001-09-07 | 2003-03-24 | Pennzoil-Quaker State Company | Diesel fuel and method of making and using same |
| CA2470079A1 (en) | 2001-12-13 | 2003-06-26 | Lehigh University | Oxidative desulfurization of sulfur-containing hydrocarbons |
| US20030149317A1 (en) | 2002-02-04 | 2003-08-07 | Rendina David Deck | Hydrogenation catalysts and methods |
| US6969500B2 (en) | 2002-03-07 | 2005-11-29 | Kronos International Inc | Method for separating titanium tetrachloride |
| US6791378B2 (en) | 2002-08-19 | 2004-09-14 | Micron Technology, Inc. | Charge recycling amplifier for a high dynamic range CMOS imager |
| EP1403358A1 (en) | 2002-09-27 | 2004-03-31 | ENI S.p.A. | Process and catalysts for deep desulphurization of fuels |
| US7153414B2 (en) | 2002-12-10 | 2006-12-26 | Petroleo Brasileiro S.A.-Petrobras | Process for the upgrading of raw hydrocarbon streams |
| AR043242A1 (es) | 2003-02-24 | 2005-07-20 | Shell Int Research | Preparacion y uso de una composicion de catalizador |
| US20040178121A1 (en) | 2003-03-13 | 2004-09-16 | Leyshon David W. | Organosulfur oxidation process |
| US7001585B2 (en) | 2003-04-23 | 2006-02-21 | Ferro Corporation | Method of making barium titanate |
| FR2854623B1 (fr) | 2003-05-09 | 2006-07-07 | Centre Nat Rech Scient | Aquo-oxo chlorure de titane, procede pour sa preparation |
| US7049347B2 (en) * | 2003-07-18 | 2006-05-23 | Ut-Battelle, Llc | Method for making fine and ultrafine spherical particles of zirconium titanate and other mixed metal oxide systems |
| CN1856564A (zh) | 2003-08-01 | 2006-11-01 | 宝洁公司 | 用于喷气机、燃气轮机、火箭和柴油发动机的燃料 |
| US7144499B2 (en) * | 2003-11-26 | 2006-12-05 | Lyondell Chemical Technology, L.P. | Desulfurization process |
| US20100098602A1 (en) | 2003-12-19 | 2010-04-22 | Opinder Kishan Bhan | Systems, methods, and catalysts for producing a crude product |
| US7591941B2 (en) | 2003-12-19 | 2009-09-22 | Shell Oil Company | Systems, methods, and catalysts for producing a crude product |
| US20070000810A1 (en) | 2003-12-19 | 2007-01-04 | Bhan Opinder K | Method for producing a crude product with reduced tan |
| US7763160B2 (en) | 2003-12-19 | 2010-07-27 | Shell Oil Company | Systems and methods of producing a crude product |
| US7314545B2 (en) | 2004-01-09 | 2008-01-01 | Lyondell Chemical Technology, L.P. | Desulfurization process |
| WO2006009742A1 (en) | 2004-06-17 | 2006-01-26 | Exxonmobil Research And Engineering Company | Catalyst combination and two-step hydroprocessing method for heavy hydrocarbon oil |
| TWI282777B (en) | 2004-09-20 | 2007-06-21 | Tonyong Applied Materials Tech | Method for preparing barium titanate |
| KR20070091297A (ko) | 2004-12-29 | 2007-09-10 | 비피 코포레이션 노쓰 아메리카 인코포레이티드 | 산화적 탈황 방법 |
| US7410631B2 (en) | 2005-03-02 | 2008-08-12 | Aps Laboratory | Metal phosphate sols, metal nanoparticles, metal-chalcogenide nanoparticles, and nanocomposites made therefrom |
| JP2008535999A (ja) | 2005-04-11 | 2008-09-04 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | 原油生成物を製造するためのシステム、方法及び触媒 |
| US7918992B2 (en) | 2005-04-11 | 2011-04-05 | Shell Oil Company | Systems, methods, and catalysts for producing a crude product |
| JP2008536002A (ja) | 2005-04-11 | 2008-09-04 | シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ | 原油生成物を製造するためのシステム、方法及び触媒 |
| US20060231457A1 (en) | 2005-04-11 | 2006-10-19 | Bhan Opinder K | Systems, methods, and catalysts for producing a crude product |
| BRPI0609416A2 (pt) | 2005-04-11 | 2011-10-11 | Shell Int Research | método para produzir um produto bruto |
| US7744749B2 (en) | 2005-09-08 | 2010-06-29 | Saudi Arabian Oil Company | Diesel oil desulfurization by oxidation and extraction |
| US20070256980A1 (en) | 2006-03-31 | 2007-11-08 | Perry Equipment Corporation | Countercurrent systems and methods for treatment of contaminated fluids |
| EP2010754A4 (en) | 2006-04-21 | 2016-02-24 | Shell Int Research | ADJUSTING ALLOY COMPOSITIONS FOR SELECTED CHARACTERISTICS IN TEMPERATURE-LIMITED HEATERS |
| WO2007149923A2 (en) | 2006-06-22 | 2007-12-27 | Shell Oil Company | Method for producing a crude product with a long-life catalyst |
| US20080083655A1 (en) | 2006-10-06 | 2008-04-10 | Bhan Opinder K | Methods of producing a crude product |
| CN101161625A (zh) | 2006-10-12 | 2008-04-16 | 高化环保技术有限公司 | 用均相mc型催化剂和o2/co2混合物制备有机酸或其衍生物的方法 |
| CA2624746C (en) | 2007-03-12 | 2015-02-24 | Robert Graham | Methods and systems for producing reduced resid and bottomless products from heavy hydrocarbon feedstocks |
| US7790021B2 (en) | 2007-09-07 | 2010-09-07 | Uop Llc | Removal of sulfur-containing compounds from liquid hydrocarbon streams |
| US7875185B2 (en) | 2007-09-10 | 2011-01-25 | Merichem Company | Removal of residual sulfur compounds from a caustic stream |
| US8241490B2 (en) | 2008-03-26 | 2012-08-14 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US9061273B2 (en) | 2008-03-26 | 2015-06-23 | Auterra, Inc. | Sulfoxidation catalysts and methods and systems of using same |
| US8197671B2 (en) | 2008-03-26 | 2012-06-12 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US8894843B2 (en) | 2008-03-26 | 2014-11-25 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US8764973B2 (en) | 2008-03-26 | 2014-07-01 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| US8298404B2 (en) | 2010-09-22 | 2012-10-30 | Auterra, Inc. | Reaction system and products therefrom |
| US9206359B2 (en) | 2008-03-26 | 2015-12-08 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| RU2472841C2 (ru) | 2008-03-26 | 2013-01-20 | Отерра, Инк. | Катализаторы сульфоокисления и способы и системы их применения |
| US8114806B2 (en) | 2008-04-10 | 2012-02-14 | Shell Oil Company | Catalysts having selected pore size distributions, method of making such catalysts, methods of producing a crude product, products obtained from such methods, and uses of products obtained |
| WO2009126909A1 (en) | 2008-04-10 | 2009-10-15 | Shell Oil Company | Catalyst systems and methods for converting a crude feed with such catalyst systems |
| WO2011002745A1 (en) | 2009-07-01 | 2011-01-06 | Saudi Arabian Oil Company | Membrane desulfurization of liquid hydrocarbons using an extractive liquid membrane contactor system and method |
| US8562818B2 (en) | 2010-01-21 | 2013-10-22 | Shell Oil Company | Hydrocarbon composition |
| WO2011091200A2 (en) | 2010-01-21 | 2011-07-28 | Shell Oil Company | Hydrocarbon composition |
| US8597608B2 (en) | 2010-01-21 | 2013-12-03 | Shell Oil Company | Manganese tetrathiotungstate material |
| US8409541B2 (en) | 2010-01-21 | 2013-04-02 | Shell Oil Company | Process for producing a copper thiometallate or a selenometallate material |
| US8530370B2 (en) | 2010-01-21 | 2013-09-10 | Shell Oil Company | Nano-tetrathiometallate or nano-tetraselenometallate material |
| EP2526166A2 (en) | 2010-01-21 | 2012-11-28 | Shell Oil Company | Hydrocarbon composition |
| US8658027B2 (en) | 2010-03-29 | 2014-02-25 | Saudi Arabian Oil Company | Integrated hydrotreating and oxidative desulfurization process |
| CN103037968B (zh) | 2010-06-01 | 2016-08-24 | 埃克森美孚研究工程公司 | 加氢处理催化剂和它们的制备 |
| US9574143B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Desulfurization and sulfone removal using a coker |
| US9598647B2 (en) | 2010-09-07 | 2017-03-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and sulfone disposal using solvent deasphalting |
| US9574142B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and sulfone management by gasification |
| US9574144B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and denitrogenation using a fluid catalytic cracking (FCC) unit |
| US8790508B2 (en) | 2010-09-29 | 2014-07-29 | Saudi Arabian Oil Company | Integrated deasphalting and oxidative removal of heteroatom hydrocarbon compounds from liquid hydrocarbon feedstocks |
| US8741128B2 (en) | 2010-12-15 | 2014-06-03 | Saudi Arabian Oil Company | Integrated desulfurization and denitrification process including mild hydrotreating of aromatic-lean fraction and oxidation of aromatic-rich fraction |
| US10647926B2 (en) | 2010-12-15 | 2020-05-12 | Saudi Arabian Oil Company | Desulfurization of hydrocarbon feed using gaseous oxidant |
| US20130015104A1 (en) | 2011-07-12 | 2013-01-17 | Adnan Al-Hajji | Process for sulfone conversion by super electron donors |
| US9005433B2 (en) | 2011-07-27 | 2015-04-14 | Saudi Arabian Oil Company | Integrated process for in-situ organic peroxide production and oxidative heteroatom conversion |
| US9663725B2 (en) | 2011-07-27 | 2017-05-30 | Saudi Arabian Oil Company | Catalytic compositions useful in removal of sulfur compounds from gaseous hydrocarbons, processes for making these and uses thereof |
| US9062259B2 (en) | 2011-07-29 | 2015-06-23 | Saudi Arabian Oil Company | Oxidative desulfurization in fluid catalytic cracking process |
| JP2014528974A (ja) | 2011-07-31 | 2014-10-30 | サウジ アラビアン オイル カンパニー | スルホン分解と統合される酸化的脱硫のプロセス |
| KR101955702B1 (ko) | 2011-07-31 | 2019-03-07 | 사우디 아라비안 오일 컴퍼니 | 아스팔트 및 탈황 오일을 제조하는 통합 공정 |
| CN104011180B (zh) | 2011-09-27 | 2017-09-05 | 沙特阿拉伯石油公司 | 氧化脱硫反应产物的选择性液‑液萃取 |
| JP6240091B2 (ja) | 2012-01-13 | 2017-11-29 | アスペン テクノロジー インコーポレイテッド | 石油精製のために原油の化学組成をキャラクタリゼーションする方法 |
| RU2014152661A (ru) | 2012-06-11 | 2016-07-27 | Отерра, Инк. | Способы облагораживания содержащих примеси углеводородных потоков |
| US9969950B2 (en) | 2012-07-17 | 2018-05-15 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless TBN sourcces |
| CA2879626C (en) | 2012-07-27 | 2020-09-08 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
| WO2014095813A1 (en) | 2012-12-17 | 2014-06-26 | Shell Internationale Research Maatschappij B.V. | Process for preparing a hydrowax |
| US20150337208A1 (en) | 2014-05-23 | 2015-11-26 | Auterra, Inc. | Hydrocarbon products |
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2008
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- 2008-05-02 BR BRPI0809881-6A patent/BRPI0809881B1/pt active IP Right Grant
- 2008-05-02 KR KR1020097024832A patent/KR101642695B1/ko not_active Expired - Fee Related
- 2008-05-02 CN CN200880021731.7A patent/CN101815720B/zh not_active Expired - Fee Related
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Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0809881B1 (pt) | 2019-08-20 |
| CA2685850A1 (en) | 2008-12-18 |
| ES2345705T1 (es) | 2010-09-30 |
| US9512151B2 (en) | 2016-12-06 |
| WO2008153633A2 (en) | 2008-12-18 |
| JP5537418B2 (ja) | 2014-07-02 |
| CA2927919A1 (en) | 2008-12-18 |
| KR101642695B1 (ko) | 2016-07-27 |
| CN101815720B (zh) | 2014-06-04 |
| EP2150557A2 (en) | 2010-02-10 |
| EP2150557B1 (en) | 2016-07-13 |
| AU2008262567A1 (en) | 2008-12-18 |
| KR20100029184A (ko) | 2010-03-16 |
| AU2008262567B2 (en) | 2013-05-16 |
| CA2685850C (en) | 2016-06-28 |
| EP3078726A1 (en) | 2016-10-12 |
| JP2010528984A (ja) | 2010-08-26 |
| PL2150557T3 (pl) | 2016-12-30 |
| DE08825898T1 (de) | 2010-10-21 |
| WO2008153633A3 (en) | 2009-07-09 |
| US20110119988A1 (en) | 2011-05-26 |
| BRPI0809881A2 (pt) | 2018-10-30 |
| CN101815720A (zh) | 2010-08-25 |
| EP2150557A4 (en) | 2012-02-08 |
| ES2345705T3 (es) | 2016-11-28 |
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