DK2150557T3 - Produkt indeholdende monomer og polymere af titanyler og fremgangsmåder til fremstilling deraf. - Google Patents
Produkt indeholdende monomer og polymere af titanyler og fremgangsmåder til fremstilling deraf. 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
Links
- 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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- ARCJQKUWGAZPFX-KBPBESRZSA-N S-trans-stilbene oxide Chemical compound C1([C@H]2[C@@H](O2)C=2C=CC=CC=2)=CC=CC=C1 ARCJQKUWGAZPFX-KBPBESRZSA-N 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000005602 azabenzimidazolyl group Chemical group 0.000 description 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 2
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(iv) oxide Chemical compound O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- ZQGJEUVBUVKZKS-UHFFFAOYSA-N n,2-dimethylpropan-2-amine Chemical compound CNC(C)(C)C ZQGJEUVBUVKZKS-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 125000001477 organic nitrogen group Chemical group 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 229960002920 sorbitol Drugs 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010902 straw Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- XEGAKAFEBOXGPV-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-benzotriazole Chemical compound C1C=CC=C2NNNC12 XEGAKAFEBOXGPV-UHFFFAOYSA-N 0.000 description 1
- FOCKIYZLSZKVDH-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-b]pyridine Chemical compound N1C=CC=C2NCNC21 FOCKIYZLSZKVDH-UHFFFAOYSA-N 0.000 description 1
- FRUWMYWEARDNTC-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-indole Chemical compound C1C=CC=C2NCCC21 FRUWMYWEARDNTC-UHFFFAOYSA-N 0.000 description 1
- PLDDTNKKLOTJCZ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CNC2CNNC2=C1 PLDDTNKKLOTJCZ-UHFFFAOYSA-N 0.000 description 1
- CKFADRWPUYOHOZ-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-pyrrolo[3,2-b]pyridine Chemical compound N1C=CC=C2NCCC21 CKFADRWPUYOHOZ-UHFFFAOYSA-N 0.000 description 1
- IBLQRMNMEWSJHT-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-triazolo[4,5-b]pyridine Chemical compound N1C=CC=C2NNNC21 IBLQRMNMEWSJHT-UHFFFAOYSA-N 0.000 description 1
- CSDFHCDNAZPVKH-UHFFFAOYSA-N 2,3,3a,7a-tetrahydro-1h-indazole Chemical compound C1=CC=CC2CNNC21 CSDFHCDNAZPVKH-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AOJQCQOIDWVXSU-UHFFFAOYSA-N 3,3,3-trimethoxypropan-1-ol Chemical compound COC(OC)(OC)CCO AOJQCQOIDWVXSU-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- OURXRFYZEOUCRM-UHFFFAOYSA-N 4-hydroxymorpholine Chemical compound ON1CCOCC1 OURXRFYZEOUCRM-UHFFFAOYSA-N 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 241001088180 Eremocosta titania Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000012901 Milli-Q water Substances 0.000 description 1
- 238000012565 NMR experiment Methods 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 229910003074 TiCl4 Inorganic materials 0.000 description 1
- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical class CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- NABZXASCLFSKLF-UHFFFAOYSA-N [1,2]oxazolo[4,3-b]pyridine Chemical compound C1=CC=NC2=CON=C21 NABZXASCLFSKLF-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 125000005426 adeninyl group Chemical group N1=C(N=C2N=CNC2=C1N)* 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- VZSXFJPZOCRDPW-UHFFFAOYSA-N carbanide;trioxorhenium Chemical compound [CH3-].O=[Re](=O)=O VZSXFJPZOCRDPW-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 description 1
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000013056 hazardous product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 125000002192 heptalenyl group Chemical group 0.000 description 1
- 125000005945 imidazopyridyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000003427 indacenyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011234 nano-particulate material Substances 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- IVMHDOBGNQOUHO-UHFFFAOYSA-N oxathiane Chemical compound C1CCSOC1 IVMHDOBGNQOUHO-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FXWGWZQOSOJYOC-UHFFFAOYSA-N propane-1,2,3-triol;titanium Chemical class [Ti].OCC(O)CO FXWGWZQOSOJYOC-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005944 tetrahydroimidazopyridyl group Chemical group 0.000 description 1
- 125000005888 tetrahydroindolyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004927 thianaphthalenyl group Chemical group S1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- OVCXRBARSPBVMC-UHFFFAOYSA-N triazolopyridine Chemical compound C=1N2C(C(C)C)=NN=C2C=CC=1C=1OC=NC=1C1=CC=C(F)C=C1 OVCXRBARSPBVMC-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 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
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (15)
1. Forbindelse med formlen I: MmOm(OR2)n (I); i hvilken: M er Ti, Zr eller Hf; R2 i hver forekomst er individuelt en substitueret alkylgruppe indeholdende mindst én OH-gruppe, en substitueret cycloalkylgruppe indeholdende mindst én OH-gruppe, en substitueret cycloalkylalkylgruppe indeholdende mindst én OH-gruppe, en substitueret heterocyclylgruppe indeholdende mindst én OH-gruppe, eller en heterocyclylalkylgruppe indeholdende mindst én OH-gruppe; og m er et heltal fra 1 til 8; og n er et heltal fra 1 til 8.
2. Forbindelse ifølge krav 1, hvor forbindelsen med formlen I er en forbindelse med formlen II
en forbindelse med formlen III
en isomer af forbindelsen med formlen II eller III, eller en blanding af vilkårlige to eller flere deraf; hvor: M er Ti eller Zr; R3 i hver forekomst er uafhængigt H, F, Cl, Br, I, CN, OR4, NR5R6, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret cycloalkyl, substitueret eller usubstitueret cycl oal kyl al kyl, usubstitueret heterocyclyl, eller substitueret eller usubstitueret heterocyclylalkyl; R4 er H, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret cy-cloalkyl, substitueret eller usubstitueret cycloalkylalkyl, usubstitueret heterocyclyl, eller substitueret eller usubstitueret heterocyclylalkyl; R5 og R6 er uafhængigt H, substitueret eller usubstitueret alkyl, substitueret eller usubstitueret cycloalkyl, substitueret eller usubstitueret heterocyclylalkyl, eller R5 og R6 danner en heterocyklisk ring indeholdende det N-atom, hvortil de er bundet; og n' er 1,2, 3 eller 4.
3. Forbindelse ifølge krav 2, i hvilken M er Ti.
4. Forbindelse ifølge krav 2, i hvilken R3 i hver forekomst er uafhængigt H, OR4 eller en substitueret eller usubstitueret alkylgruppe.
5. Forbindelse ifølge krav 2, hvor forbindelsen er bis(ethylenglycol)oxotitanium (IV), bis(glycerol)oxotitanium (IV), bis(erythritol)oxotitanium (IV) eller bis(sorbitol)oxotitanium (IV).
6. Sammensætning indeholdende forbindelsen ifølge krav 1 og en polymerharpiks.
7. Fremgangsmåde omfattende: tilvejebringelse af et kontamineret brændstof; fremstilling af en blanding af brændstoffet, en forbindelse med formlen I, en organisk syre; og en oxidant; og udvinding af et dekontamineret brændstof; hvor formlen I er MmOm(OR2)n (I); M er Ti, Zr eller Hf; R2 i hver forekomst er individuelt en substitueret alkylgruppe indeholdende mindst én OH-gruppe, en substitueret cycloalkylgruppe indeholdende mindst én OH- gruppe, en substitueret cycloalkylalkylgruppe indeholdende mindst én OH-gruppe, en substitueret heterocyclylgruppe indeholdende mindst én OH-gruppe, eller en heterocyclylalkylgruppe indeholdende mindst én OH-gruppe; og m er et heltal fra 1 til 8; og n er et heltal fra 1 til 8.
8. Fremgangsmåde ifølge krav 7, ved hvilken forbindelsen med formlen I er valgt fra gruppen bestående af bis(ethylenglycol)oxotitanium (IV), bis(glycerol)oxotitanium (IV), bis(erythritol)oxotitanium (IV) eller bis(sorbitol)oxotitanium (IV).
9. Fremgangsmåde ifølge krav 7, ved hvilken det kontaminerede brændstof omfatter et brændstof og én eller flere kontaminanter valgt fra en svovlkontami-nant, en nitrogenkontaminant eller en blanding deraf.
10. Fremgangsmåde ifølge krav 7, ved hvilken den organiske syre er valgt fra gruppen bestående af HCO2H, CH3-xClxC02H, CF3CO2H og blandinger af vilkårlige to eller flere deraf, hvor x er et heltal fra 0 til 3.
11. Fremgangsmåde ifølge krav 7, ved hvilken oxidanten er valgt fra gruppen bestående af et organisk nitrogenoxid, salpetersyre, hydrogenperoxid, ozon, et organisk peroxid, oxygen, luft, en persyre, et hypochlorit og blandinger af vilkårlige to eller flere deraf.
12. Fremgangsmåde ifølge krav 7, ved hvilken det svovlkontaminerede brændstof er til stede i en mængde fra 30 vægt-% ± op til 10% til 70 vægt-% ± op til 10%, den organiske syre er til stede i en mængde fra 20 vægt-% ± op til 10% til 60 vægt-% ± op til 10%, oxidanten er til stede i en mængde fra 5 vægt-% ± op til 10% til 20 vægt-% ± op til 10%, og forbindelsen med formlen I er til stede i en mængde på 0,5 ppm eller mere i forhold til brændstoffet.
13. Fremgangsmåde ifølge krav 7, ved hvilken blandingen opvarmes til en temperatur fra 30 til 130°C ± op til 10%.
14. Fremgangsmåde ifølge krav 7, ved hvilken blandingen opvarmes i fra 5 sekunder til 60 minutter ± op til 10%.
15. Fremgangsmåde ifølge krav 7, ved hvilken det kontaminerede brændstof er en råolie, et dieselbrændstof eller en termisk krakket benzin.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 (da) | 2016-08-29 |
Family
ID=40130362
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK08825898.3T DK2150557T3 (da) | 2007-05-03 | 2008-05-02 | Produkt indeholdende monomer og polymere af titanyler og fremgangsmåder til fremstilling deraf. |
Country Status (13)
Country | Link |
---|---|
US (1) | US9512151B2 (da) |
EP (2) | EP3078726A1 (da) |
JP (1) | JP5537418B2 (da) |
KR (1) | KR101642695B1 (da) |
CN (1) | CN101815720B (da) |
AU (1) | AU2008262567B2 (da) |
BR (1) | BRPI0809881B1 (da) |
CA (2) | CA2685850C (da) |
DE (1) | DE08825898T1 (da) |
DK (1) | DK2150557T3 (da) |
ES (1) | ES2345705T3 (da) |
PL (1) | PL2150557T3 (da) |
WO (1) | WO2008153633A2 (da) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101642695B1 (ko) | 2007-05-03 | 2016-07-27 | 오테라, 인코포레이티드 | 티타닐의 단량체와 중합체를 함유하는 생성물과 이를 제조하는 방법 |
EP2265694B1 (en) * | 2008-03-26 | 2017-05-17 | Auterra, Inc. | Sulfoxidation method |
US9206359B2 (en) | 2008-03-26 | 2015-12-08 | 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 |
CN102906162B (zh) * | 2010-05-10 | 2014-12-10 | 学校法人关西大学 | 固化性组合物、使用其的环氧树脂-无机高分子复合材料的制造方法及环氧树脂-无机高分子复合材料 |
RU2581473C2 (ru) * | 2010-07-20 | 2016-04-20 | Отерра, Инк. | Окислительная десульфуризация с использованием катализатора на основе титана (iv) и органогидропероксидов |
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 |
EP2754638B1 (en) | 2011-09-05 | 2018-11-07 | Tosoh Corporation | Film-forming material, group iv metal oxide film and vinylene diamide complex |
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 |
WO2022065127A1 (ja) * | 2020-09-24 | 2022-03-31 | 東レ株式会社 | 組成物、硬化体およびその製造方法、ならびに部材、電子部品および繊維 |
Family Cites Families (141)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE520661A (da) | 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 (da) | 1961-11-10 | |||
US3164545A (en) | 1962-12-26 | 1965-01-05 | Exxon Research Engineering Co | Desulfurization process |
NL6602260A (da) | 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 (da) | 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 |
US3960706A (en) | 1974-05-31 | 1976-06-01 | Standard Oil Company | Process for upgrading a hydrocarbon fraction |
US3960708A (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 |
EP1200353B1 (en) * | 1999-07-01 | 2003-04-02 | 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 |
WO2001081715A2 (en) | 2000-04-24 | 2001-11-01 | Shell Internationale Research Maatschappij B.V. | Method and system for treating a hydrocarbon containing formation |
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 |
WO2003011762A1 (fr) | 2001-07-27 | 2003-02-13 | Chiyoda Corporation | Oxyde d'un metal du groupe 4 poreux et procede de preparation de ce dernier |
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 |
US7598426B2 (en) | 2001-09-07 | 2009-10-06 | Shell Oil Company | Self-lubricating diesel fuel and method of making and using same |
EP1461302A4 (en) | 2001-12-13 | 2006-08-02 | Univ Lehigh | OXIDATIVE DESULFURATION OF SULFUR 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 |
EP1648982A2 (en) | 2003-08-01 | 2006-04-26 | The Procter & Gamble Company | Fuel for jet, gas turbine, rocket, and diesel engines |
US7144499B2 (en) | 2003-11-26 | 2006-12-05 | Lyondell Chemical Technology, L.P. | Desulfurization process |
US7591941B2 (en) | 2003-12-19 | 2009-09-22 | Shell Oil Company | Systems, methods, and catalysts for producing a crude product |
US20050133405A1 (en) | 2003-12-19 | 2005-06-23 | Wellington Scott L. | Systems and methods of producing a crude product |
US20100098602A1 (en) | 2003-12-19 | 2010-04-22 | Opinder Kishan Bhan | 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 |
US7314545B2 (en) | 2004-01-09 | 2008-01-01 | Lyondell Chemical Technology, L.P. | Desulfurization process |
MXPA06014513A (es) | 2004-06-17 | 2007-03-23 | Exxonmobil Res & Eng Co | Combinacion de catalizador y metodo de hidroprocesamiento de dos pasos para aceite de hidrocarburo pesado. |
TWI282777B (en) * | 2004-09-20 | 2007-06-21 | Tonyong Applied Materials Tech | Method for preparing barium titanate |
MX2007007802A (es) | 2004-12-29 | 2007-07-25 | Bp Corp North America Inc | Proceso de desulfuracion oxidativa. |
US7410631B2 (en) | 2005-03-02 | 2008-08-12 | Aps Laboratory | Metal phosphate sols, metal nanoparticles, metal-chalcogenide nanoparticles, and nanocomposites made therefrom |
US20060231456A1 (en) | 2005-04-11 | 2006-10-19 | Bhan Opinder K | Systems, methods, and catalysts for producing a crude product |
BRPI0610669A2 (pt) | 2005-04-11 | 2017-01-31 | Shell Int Research | método para produzir um produto bruto |
CA2604012C (en) | 2005-04-11 | 2013-11-19 | Shell Internationale Research Maatschappij B.V. | Method and catalyst for producing a crude product having a reduced mcr content |
BRPI0609411A2 (pt) | 2005-04-11 | 2011-10-11 | Shell Int Research | método para produzir um produto bruto |
WO2006110556A1 (en) | 2005-04-11 | 2006-10-19 | Shell International Research Maatschappij B.V. | Method and catalyst for producing a crude product having a reduced nitroge content |
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 |
CA2649379C (en) | 2006-04-21 | 2016-08-23 | Shell Internationale Research Maatschappij B.V. | Heating systems and methods using high strength alloys |
CA2655600A1 (en) | 2006-06-22 | 2007-12-27 | Shell Internationale Research Maatschappij B.V. | Method for producing a crude product with a long-life catalyst |
US7749374B2 (en) | 2006-10-06 | 2010-07-06 | Shell Oil Company | Methods for producing a crude product |
EP1911737A1 (en) | 2006-10-12 | 2008-04-16 | Kocat Inc. | Process for preparing an organic acid or its derivatives using a homogeneous MC-Type catalyst an O2/CO2 mixture |
CA2624746C (en) | 2007-03-12 | 2015-02-24 | Robert Graham | Methods and systems for producing reduced resid and bottomless products from heavy hydrocarbon feedstocks |
KR101642695B1 (ko) | 2007-05-03 | 2016-07-27 | 오테라, 인코포레이티드 | 티타닐의 단량체와 중합체를 함유하는 생성물과 이를 제조하는 방법 |
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 |
US9206359B2 (en) | 2008-03-26 | 2015-12-08 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
US8241490B2 (en) | 2008-03-26 | 2012-08-14 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
US8298404B2 (en) | 2010-09-22 | 2012-10-30 | Auterra, Inc. | Reaction system and products therefrom |
US9061273B2 (en) | 2008-03-26 | 2015-06-23 | Auterra, Inc. | Sulfoxidation catalysts and methods and systems of using same |
US8764973B2 (en) | 2008-03-26 | 2014-07-01 | 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 |
US8197671B2 (en) | 2008-03-26 | 2012-06-12 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
EP2265694B1 (en) | 2008-03-26 | 2017-05-17 | Auterra, Inc. | Sulfoxidation method |
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 |
BRPI0911062B1 (pt) | 2008-04-10 | 2018-06-05 | Shell Internationale Research Maatschappij B.V. | Sistema catalítico, método para tratamento de uma alimentação crua e catalasidor compreendendo metais de hidrogenação e um suporte |
US20110000823A1 (en) | 2009-07-01 | 2011-01-06 | Feras Hamad | Membrane desulfurization of liquid hydrocarbons using an extractive liquid membrane contactor system and method |
WO2011091193A2 (en) | 2010-01-21 | 2011-07-28 | Shell Oil Company | Nano-tetrathiometallate or nano-tetraselenometallate material |
CA2785761C (en) | 2010-01-21 | 2018-10-23 | Shell Internationale Research Maatschappij B.V. | Hydrocarbon composition |
WO2011091221A2 (en) | 2010-01-21 | 2011-07-28 | Shell Oil Company | Manganese tetrathiotungstate material |
WO2011091200A2 (en) | 2010-01-21 | 2011-07-28 | Shell Oil Company | Hydrocarbon composition |
WO2011091206A2 (en) | 2010-01-21 | 2011-07-28 | Shell Oil Company | Hydrocarbon composition |
EP2526062B1 (en) | 2010-01-21 | 2020-03-18 | Shell Oil Company | Process for producing a copper thiometallate or a selenometallate material |
US8658027B2 (en) | 2010-03-29 | 2014-02-25 | Saudi Arabian Oil Company | Integrated hydrotreating and oxidative desulfurization process |
EP2576053B1 (en) | 2010-06-01 | 2018-04-25 | ExxonMobil Research and Engineering Company | Hydroprocessing catalysts and their production |
US9574143B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Desulfurization and sulfone removal using a coker |
US9574142B2 (en) | 2010-09-07 | 2017-02-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and sulfone management by gasification |
US9598647B2 (en) | 2010-09-07 | 2017-03-21 | Saudi Arabian Oil Company | Process for oxidative desulfurization and sulfone disposal using solvent deasphalting |
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 |
CN103313956A (zh) | 2010-12-15 | 2013-09-18 | 沙特***石油公司 | 使用气态氧化剂的烃原料流的脱硫 |
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 |
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 |
CN104136116B (zh) | 2011-07-27 | 2017-02-08 | 沙特***石油公司 | 用于从气态烃中除去硫化合物的催化组合物、制造它们的方法及其用途 |
WO2013019629A1 (en) | 2011-07-29 | 2013-02-07 | Saudi Arabian Oil Company | Oxidative desulfurization in fluid catalytic cracking process |
CN107446620A (zh) | 2011-07-31 | 2017-12-08 | 沙特***石油公司 | 生产沥青和脱硫油的一体化方法 |
CN103842319B (zh) | 2011-07-31 | 2017-06-09 | 沙特***石油公司 | 具有整合的砜分解的氧化脱硫方法 |
WO2013049177A1 (en) | 2011-09-27 | 2013-04-04 | Saudi Arabian Oil Company | Selective liquid-liquid extraction of oxidative desulfurization reaction products |
WO2013106755A1 (en) | 2012-01-13 | 2013-07-18 | Aspen Technology, Inc. | Method of characterizing chemical composition of crude oil for petroleum refinery processing |
WO2013188144A1 (en) | 2012-06-11 | 2013-12-19 | Auterra, Inc. | Methods for upgrading of contaminated hydrocarbon streams |
US9969950B2 (en) | 2012-07-17 | 2018-05-15 | Infineum International Limited | Lubricating oil compositions containing sterically hindered amines as ashless TBN sourcces |
WO2014018082A1 (en) | 2012-07-27 | 2014-01-30 | 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 |
-
2008
- 2008-05-02 KR KR1020097024832A patent/KR101642695B1/ko active IP Right Grant
- 2008-05-02 BR BRPI0809881-6A patent/BRPI0809881B1/pt active IP Right Grant
- 2008-05-02 ES ES08825898.3T patent/ES2345705T3/es active Active
- 2008-05-02 JP JP2010506321A patent/JP5537418B2/ja active Active
- 2008-05-02 DE DE08825898T patent/DE08825898T1/de active Pending
- 2008-05-02 AU AU2008262567A patent/AU2008262567B2/en not_active Ceased
- 2008-05-02 WO PCT/US2008/005624 patent/WO2008153633A2/en active Application Filing
- 2008-05-02 US US12/598,474 patent/US9512151B2/en active Active
- 2008-05-02 CA CA2685850A patent/CA2685850C/en active Active
- 2008-05-02 EP EP16161158.7A patent/EP3078726A1/en not_active Withdrawn
- 2008-05-02 DK DK08825898.3T patent/DK2150557T3/da active
- 2008-05-02 CN CN200880021731.7A patent/CN101815720B/zh active Active
- 2008-05-02 EP EP08825898.3A patent/EP2150557B1/en active Active
- 2008-05-02 CA CA2927919A patent/CA2927919A1/en not_active Abandoned
- 2008-05-02 PL PL08825898.3T patent/PL2150557T3/pl unknown
Also Published As
Publication number | Publication date |
---|---|
EP2150557B1 (en) | 2016-07-13 |
AU2008262567B2 (en) | 2013-05-16 |
DE08825898T1 (de) | 2010-10-21 |
CA2685850A1 (en) | 2008-12-18 |
WO2008153633A2 (en) | 2008-12-18 |
BRPI0809881B1 (pt) | 2019-08-20 |
CN101815720B (zh) | 2014-06-04 |
ES2345705T1 (es) | 2010-09-30 |
CA2685850C (en) | 2016-06-28 |
ES2345705T3 (es) | 2016-11-28 |
CA2927919A1 (en) | 2008-12-18 |
US20110119988A1 (en) | 2011-05-26 |
EP2150557A4 (en) | 2012-02-08 |
CN101815720A (zh) | 2010-08-25 |
JP5537418B2 (ja) | 2014-07-02 |
KR101642695B1 (ko) | 2016-07-27 |
EP3078726A1 (en) | 2016-10-12 |
WO2008153633A3 (en) | 2009-07-09 |
PL2150557T3 (pl) | 2016-12-30 |
AU2008262567A1 (en) | 2008-12-18 |
KR20100029184A (ko) | 2010-03-16 |
EP2150557A2 (en) | 2010-02-10 |
JP2010528984A (ja) | 2010-08-26 |
US9512151B2 (en) | 2016-12-06 |
BRPI0809881A2 (pt) | 2018-10-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DK2150557T3 (da) | Produkt indeholdende monomer og polymere af titanyler og fremgangsmåder til fremstilling deraf. | |
CA2719058C (en) | Sulfoxidation catalysts and methods and systems of using same | |
US9061273B2 (en) | Sulfoxidation catalysts and methods and systems of using same | |
Banisharif et al. | Oxidative desulfurization of diesel using vanadium-substituted dawson-type emulsion catalysts | |
Zhang et al. | Catalytic oxidative desulfurization of fuel by H2O2 in situ produced via oxidation of 2-propanol | |
KR20050117560A (ko) | 유기황의 산화 방법 | |
WO2012012368A1 (en) | Oxidative desulfurization using a titanium(iv) catalyst and organhoydroperoxides | |
US20050178050A1 (en) | Transportation fuels | |
US20020148754A1 (en) | Integrated preparation of blending components for refinery transportation fuels | |
AU2002251783A1 (en) | Integrated preparation of blending components for refinery transportation fuels | |
Alibolandi et al. | Oxidative desulfurization of sour Gas condensate and optimization of parameters with response surface methodology | |
Kumar et al. | Desulphurization of gas oil in a packed bed extractor: Optimization of operating parameters for simultaneous maximization of efficiency and yield by desirability approach |