ES2266923T3 - Procedimiento de oxidacion de materia organosulfurada. - Google Patents

Procedimiento de oxidacion de materia organosulfurada. Download PDF

Info

Publication number: ES2266923T3
Authority: ES; Spain
Prior art keywords: catalyst; titanium; hydroperoxide; hydrocarbons; carbon atoms
Prior art date: 2003-03-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES03816406T

Other languages

English (en)

Spanish (es)

Inventor

David W. Leyshon

Lawrence J. Karas

Yuan-Zhang Han

Kevin M. Carroll

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Lyondell Chemical Technology LP

Original Assignee

Lyondell Chemical Technology LP

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-03-13

Filing date

2003-12-19

Publication date

2007-03-01

2003-12-19 Application filed by Lyondell Chemical Technology LP filed Critical Lyondell Chemical Technology LP

2007-03-01 Application granted granted Critical

2007-03-01 Publication of ES2266923T3 publication Critical patent/ES2266923T3/es

2023-12-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 71
238000007254 oxidation reaction Methods 0.000 title description 26
230000003647 oxidation Effects 0.000 title description 24
239000003054 catalyst Substances 0.000 claims abstract description 93
239000010936 titanium Substances 0.000 claims abstract description 53
229930195733 hydrocarbon Natural products 0.000 claims abstract description 44
229910052719 titanium Inorganic materials 0.000 claims abstract description 42
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 40
239000007787 solid Substances 0.000 claims abstract description 33
239000002904 solvent Substances 0.000 claims abstract description 32
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 31
238000001354 calcination Methods 0.000 claims abstract description 27
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 24
239000012535 impurity Substances 0.000 claims abstract description 23
-1 titanium halide Chemical class 0.000 claims abstract description 22
239000000446 fuel Substances 0.000 claims abstract description 18
150000002432 hydroperoxides Chemical class 0.000 claims abstract description 15
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims abstract description 13
150000003457 sulfones Chemical class 0.000 claims abstract description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 53
238000005470 impregnation Methods 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
239000000377 silicon dioxide Substances 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
239000012298 atmosphere Substances 0.000 claims description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
239000001301 oxygen Substances 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 6
239000002283 diesel fuel Substances 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
238000004090 dissolution Methods 0.000 claims description 3
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims 2
230000001590 oxidative effect Effects 0.000 abstract description 4
IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 34
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
239000007789 gas Substances 0.000 description 20
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
229910052717 sulfur Inorganic materials 0.000 description 14
239000011593 sulfur Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000000463 material Substances 0.000 description 11
150000004820 halides Chemical class 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000003502 gasoline Substances 0.000 description 9
239000011261 inert gas Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
238000010438 heat treatment Methods 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
MYAQZIAVOLKEGW-UHFFFAOYSA-N 4,6-dimethyldibenzothiophene Chemical compound S1C2=C(C)C=CC=C2C2=C1C(C)=CC=C2 MYAQZIAVOLKEGW-UHFFFAOYSA-N 0.000 description 5
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000006477 desulfuration reaction Methods 0.000 description 4
230000023556 desulfurization Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
238000006884 silylation reaction Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
238000011282 treatment Methods 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000001307 helium Substances 0.000 description 3
229910052734 helium Inorganic materials 0.000 description 3
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011148 porous material Substances 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003464 sulfur compounds Chemical class 0.000 description 3
238000012360 testing method Methods 0.000 description 3
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-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
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
CXRVNRVRMMXKKA-UHFFFAOYSA-N CC(C)O[Ti+2]OC(C)C Chemical compound CC(C)O[Ti+2]OC(C)C CXRVNRVRMMXKKA-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
QUWBSOKSBWAQER-UHFFFAOYSA-N [C].O=C=O Chemical compound [C].O=C=O QUWBSOKSBWAQER-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000005336 cracking Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000002803 fossil fuel Substances 0.000 description 2
239000000295 fuel oil Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
239000003350 kerosene Substances 0.000 description 2
238000011068 loading method Methods 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
239000003345 natural gas Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
150000001282 organosilanes Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000010453 quartz Substances 0.000 description 2
239000004460 silage Substances 0.000 description 2
150000004756 silanes Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
150000003577 thiophenes Chemical class 0.000 description 2
239000012808 vapor phase Substances 0.000 description 2
238000009834 vaporization Methods 0.000 description 2
230000008016 vaporization Effects 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N 2-Methylheptane Chemical class CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QJRZPVGQQPEKNL-UHFFFAOYSA-N C=ClC(Cl)Cl.Cl Chemical compound C=ClC(Cl)Cl.Cl QJRZPVGQQPEKNL-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes 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
150000004703 alkoxides Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
QZRWJJLUUOMZIT-UHFFFAOYSA-N chloro-dimethyl-pentylsilane Chemical compound CCCCC[Si](C)(C)Cl QZRWJJLUUOMZIT-UHFFFAOYSA-N 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000010908 decantation Methods 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
150000002019 disulfides Chemical class 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
FGGJBCRKSVGDPO-UHFFFAOYSA-N hydroperoxycyclohexane Chemical compound OOC1CCCCC1 FGGJBCRKSVGDPO-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003999 initiator Substances 0.000 description 1
229910052809 inorganic oxide Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000001282 iso-butane Substances 0.000 description 1
239000000669 jet aircraft fuel Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000000622 liquid--liquid extraction Methods 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
239000012229 microporous material Substances 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
125000001741 organic sulfur group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
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238000006213 oxygenation reaction Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
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150000002978 peroxides Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002952 polymeric resin Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
LTEDQKPGOZDGRZ-UHFFFAOYSA-L propan-2-olate;titanium(4+);dichloride Chemical compound Cl[Ti+2]Cl.CC(C)[O-].CC(C)[O-] LTEDQKPGOZDGRZ-UHFFFAOYSA-L 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000000956 solid--liquid extraction Methods 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
229910052815 sulfur oxide Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
150000003608 titanium Chemical class 0.000 description 1
UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
XROWMBWRMNHXMF-UHFFFAOYSA-J titanium tetrafluoride Chemical compound [F-].[F-].[F-].[F-].[Ti+4] XROWMBWRMNHXMF-UHFFFAOYSA-J 0.000 description 1
NLLZTRMHNHVXJJ-UHFFFAOYSA-J titanium tetraiodide Chemical compound I[Ti](I)(I)I NLLZTRMHNHVXJJ-UHFFFAOYSA-J 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
LAJGDBSSLQUXMC-UHFFFAOYSA-N trimethyl(nitro)silane Chemical compound C[Si](C)(C)[N+]([O-])=O LAJGDBSSLQUXMC-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
239000010457 zeolite Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
- C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
- C10G27/12—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen with oxygen-generating compounds, e.g. per-compounds, chromic acid, chromates

Landscapes

Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

ES03816406T 2003-03-13 2003-12-19 Procedimiento de oxidacion de materia organosulfurada. Expired - Lifetime ES2266923T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US387849		2003-03-13
US10/387,849 US20040178121A1 (en)	2003-03-13	2003-03-13	Organosulfur oxidation process

Publications (1)

Publication Number	Publication Date
ES2266923T3 true ES2266923T3 (es)	2007-03-01

Family

ID=32961991

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES03816406T Expired - Lifetime ES2266923T3 (es)	2003-03-13	2003-12-19	Procedimiento de oxidacion de materia organosulfurada.

Country Status (12)

Country	Link
US (1)	US20040178121A1 (pt)
EP (1)	EP1601749B1 (pt)
JP (1)	JP4209394B2 (pt)
KR (1)	KR20050115911A (pt)
CN (1)	CN100339462C (pt)
AT (1)	ATE337386T1 (pt)
AU (1)	AU2003300427A1 (pt)
BR (1)	BR0318282A (pt)
CA (1)	CA2513863A1 (pt)
DE (1)	DE60307902T2 (pt)
ES (1)	ES2266923T3 (pt)
WO (1)	WO2004083345A1 (pt)

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US7744749B2 (en)	2005-09-08	2010-06-29	Saudi Arabian Oil Company	Diesel oil desulfurization by oxidation and extraction
US8715489B2 (en) *	2005-09-08	2014-05-06	Saudi Arabian Oil Company	Process for oxidative conversion of organosulfur compounds in liquid hydrocarbon mixtures
US9512151B2 (en)	2007-05-03	2016-12-06	Auterra, Inc.	Product containing monomer and polymers of titanyls and methods for making same
US8764973B2 (en)	2008-03-26	2014-07-01	Auterra, Inc.	Methods for upgrading of contaminated hydrocarbon streams
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
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
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
WO2012036445A2 (ko) *	2010-09-13	2012-03-22	한국화학연구원	선택산화탈황용 촉매 및 그의 제조방법
US9828557B2 (en)	2010-09-22	2017-11-28	Auterra, Inc.	Reaction system, methods and products therefrom
CN102059131A (zh) *	2010-12-14	2011-05-18	华东理工大学	新型钛盐催化剂及其催化酯化反应
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
KR101918775B1 (ko) *	2012-08-23	2018-11-15	에스케이이노베이션 주식회사	탄화수소의 산화 탈황방법
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

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US3556725A (en) *	1969-02-26	1971-01-19	Sylvania Electric Prod	Process for producing low-bulk density silica
US3829392A (en) *	1970-10-01	1974-08-13	Shell Oil Co	Heterogeneous catalysts for olefin epoxidation
US3923843A (en) *	1972-03-13	1975-12-02	Shell Oil Co	Epoxidation process with improved heterogeneous catalyst
US3816301A (en) *	1972-06-30	1974-06-11	Atlantic Richfield Co	Process for the desulfurization of hydrocarbons
US5985136A (en) *	1998-06-18	1999-11-16	Exxon Research And Engineering Co.	Two stage hydrodesulfurization process
US6368495B1 (en) *	1999-06-07	2002-04-09	Uop Llc	Removal of sulfur-containing compounds from liquid hydrocarbon streams
US6114552A (en) *	1999-09-28	2000-09-05	Arco Chemical Technology, L.P.	Heterogeneous epoxidation catalyst
CN1148436C (zh) *	1999-10-28	2004-05-05	中国石油化工集团公司	氧化法精制汽油或柴油的方法
GB9925971D0 (en) *	1999-11-03	1999-12-29	Exxon Chemical Patents Inc	Reduced particulate froming distillate fuels
FR2802939B1 (fr) *	1999-12-28	2005-01-21	Elf Antar France	Procede de desulfuration des derives du thiophene contenus dans les carburants
US6402939B1 (en) *	2000-09-28	2002-06-11	Sulphco, Inc.	Oxidative desulfurization of fossil fuels with ultrasound

2003
- 2003-03-13 US US10/387,849 patent/US20040178121A1/en not_active Abandoned
- 2003-12-19 CA CA002513863A patent/CA2513863A1/en not_active Abandoned
- 2003-12-19 ES ES03816406T patent/ES2266923T3/es not_active Expired - Lifetime
- 2003-12-19 AT AT03816406T patent/ATE337386T1/de not_active IP Right Cessation
- 2003-12-19 WO PCT/US2003/041552 patent/WO2004083345A1/en not_active Ceased
- 2003-12-19 EP EP03816406A patent/EP1601749B1/en not_active Expired - Lifetime
- 2003-12-19 JP JP2004569696A patent/JP4209394B2/ja not_active Expired - Fee Related
- 2003-12-19 CN CNB2003801099391A patent/CN100339462C/zh not_active Expired - Fee Related
- 2003-12-19 BR BRPI0318282-7A patent/BR0318282A/pt not_active Application Discontinuation
- 2003-12-19 AU AU2003300427A patent/AU2003300427A1/en not_active Abandoned
- 2003-12-19 DE DE60307902T patent/DE60307902T2/de not_active Expired - Lifetime
- 2003-12-19 KR KR1020057017171A patent/KR20050115911A/ko not_active Ceased

Also Published As

Publication number	Publication date
BR0318282A (pt)	2006-05-30
CN100339462C (zh)	2007-09-26
JP4209394B2 (ja)	2009-01-14
ATE337386T1 (de)	2006-09-15
US20040178121A1 (en)	2004-09-16
EP1601749A1 (en)	2005-12-07
DE60307902D1 (de)	2006-10-05
EP1601749B1 (en)	2006-08-23
AU2003300427A1 (en)	2004-10-11
DE60307902T2 (de)	2007-02-22
JP2006514146A (ja)	2006-04-27
WO2004083345A1 (en)	2004-09-30
KR20050115911A (ko)	2005-12-08
CN1753975A (zh)	2006-03-29
CA2513863A1 (en)	2004-09-30

Publication	Publication Date	Title
ES2266923T3 (es)	2007-03-01	Procedimiento de oxidacion de materia organosulfurada.
US7314545B2 (en)	2008-01-01	Desulfurization process
ES2274325T3 (es)	2007-05-16	Proceso de oxidacion de compuestos organicos de azufre.
US20050109677A1 (en)	2005-05-26	Desulfurization process
CN1097030C (zh)	2002-12-25	选择性氧化硫化合物成为元素硫的催化剂及其制备方法和用途
US20060154814A1 (en)	2006-07-13	Process and catalysts for deep desulphurization of fuels
US20040159583A1 (en)	2004-08-19	Process for the catalytic selective oxidation of sulfur compounds
RU2581473C2 (ru)	2016-04-20	Окислительная десульфуризация с использованием катализатора на основе титана (iv) и органогидропероксидов
ES2331570T3 (es)	2010-01-08	Regeneracion de un catalizador heterogeneo.
PT1216088E (pt)	2003-10-31	Processo de remocao de compostos de enxofre de gases
RU1826987C (ru)	1993-07-07	Способ очистки высокосернистой углеводородной фракции, содержащей меркаптаны
KR100915025B1 (ko)	2009-09-02	선택산화탈황용 촉매와 이의 제조방법
WO2003044129A1 (es)	2003-05-30	Un procedimiento para la oxidacion de compuestos de azufre de las fracciones gasolina, kerosene y diesel
FI58727B (fi)	1980-12-31	Foerfarande foer katalytisk utvinning av svavel ur en gasstroem
WO2014030964A1 (ko)	2014-02-27	탄화수소의 산화 탈황방법
RU2242499C9 (ru)	2006-01-10	Способ очистки нефти, газоконденсата и их фракций от меркаптанов и сероводорода
ES2311408B1 (es)	2010-01-13	Procedimiento de eliminacion de azufre en combustibles liquidos.