CA2868877A1 - Process for removing sulfur compounds from vacuum gas oil - Google Patents
Process for removing sulfur compounds from vacuum gas oil Download PDFInfo
- Publication number
- CA2868877A1 CA2868877A1 CA2868877A CA2868877A CA2868877A1 CA 2868877 A1 CA2868877 A1 CA 2868877A1 CA 2868877 A CA2868877 A CA 2868877A CA 2868877 A CA2868877 A CA 2868877A CA 2868877 A1 CA2868877 A1 CA 2868877A1
- Authority
- CA
- Canada
- Prior art keywords
- vacuum gas
- gas oil
- phosphonium
- ionic liquid
- tetraalkylphosphonium
- Prior art date
- 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.)
- Abandoned
Links
- 150000003464 sulfur compounds Chemical class 0.000 title claims abstract description 62
- 238000000034 method Methods 0.000 title claims abstract description 53
- 239000002608 ionic liquid Substances 0.000 claims abstract description 133
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 114
- 239000007789 gas Substances 0.000 claims abstract description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 57
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 229910017464 nitrogen compound Inorganic materials 0.000 claims abstract description 15
- 150000002830 nitrogen compounds Chemical class 0.000 claims abstract description 14
- 229930195733 hydrocarbon Natural products 0.000 claims description 25
- 150000002430 hydrocarbons Chemical class 0.000 claims description 25
- -1 tetraalkylphosphonium phosphates Chemical class 0.000 claims description 23
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 claims description 17
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- RJELOMHXBLDMDB-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC RJELOMHXBLDMDB-UHFFFAOYSA-M 0.000 claims description 7
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims description 6
- JMXOUHNHEFFQIW-UHFFFAOYSA-M methyl sulfate;tributyl(methyl)phosphanium Chemical compound COS([O-])(=O)=O.CCCC[P+](C)(CCCC)CCCC JMXOUHNHEFFQIW-UHFFFAOYSA-M 0.000 claims description 5
- FUTRAFMCQUHVQM-UHFFFAOYSA-M tributyl(decyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCC[P+](CCCC)(CCCC)CCCC FUTRAFMCQUHVQM-UHFFFAOYSA-M 0.000 claims description 5
- SNXTZFCNWIVLKZ-UHFFFAOYSA-M 4-methylbenzenesulfonate;methyl-tris(2-methylpropyl)phosphanium Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.CC(C)C[P+](C)(CC(C)C)CC(C)C SNXTZFCNWIVLKZ-UHFFFAOYSA-M 0.000 claims description 4
- DSQCNXSPLHDLED-UHFFFAOYSA-M methanesulfonate;tetrabutylphosphanium Chemical compound CS([O-])(=O)=O.CCCC[P+](CCCC)(CCCC)CCCC DSQCNXSPLHDLED-UHFFFAOYSA-M 0.000 claims description 4
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 4
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 claims description 4
- XZWKMODPWAKGDP-UHFFFAOYSA-M tributyl(decyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCC[P+](CCCC)(CCCC)CCCC XZWKMODPWAKGDP-UHFFFAOYSA-M 0.000 claims description 4
- ZBZFETNHIRABGK-UHFFFAOYSA-M tributyl(hexyl)phosphanium;bromide Chemical compound [Br-].CCCCCC[P+](CCCC)(CCCC)CCCC ZBZFETNHIRABGK-UHFFFAOYSA-M 0.000 claims description 4
- AEMACIJBXGZKLE-UHFFFAOYSA-M tributyl(hexyl)phosphanium;chloride Chemical compound [Cl-].CCCCCC[P+](CCCC)(CCCC)CCCC AEMACIJBXGZKLE-UHFFFAOYSA-M 0.000 claims description 4
- SDSMZSUWTYFEBO-UHFFFAOYSA-M tributyl(methyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](C)(CCCC)CCCC SDSMZSUWTYFEBO-UHFFFAOYSA-M 0.000 claims description 4
- JQLOJTZPFXKUIM-UHFFFAOYSA-M tributyl(methyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](C)(CCCC)CCCC JQLOJTZPFXKUIM-UHFFFAOYSA-M 0.000 claims description 4
- UJMLRSWRUXXZEW-UHFFFAOYSA-M tributyl(octyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCC[P+](CCCC)(CCCC)CCCC UJMLRSWRUXXZEW-UHFFFAOYSA-M 0.000 claims description 4
- JDAJRHLAMCYXAN-UHFFFAOYSA-M tributyl(octyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CCCC)(CCCC)CCCC JDAJRHLAMCYXAN-UHFFFAOYSA-M 0.000 claims description 4
- JCQGIZYNVAZYOH-UHFFFAOYSA-M trihexyl(tetradecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC JCQGIZYNVAZYOH-UHFFFAOYSA-M 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 235000021317 phosphate Nutrition 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 230000001172 regenerating effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 36
- 239000011593 sulfur Substances 0.000 description 36
- 229910052717 sulfur Inorganic materials 0.000 description 36
- 239000003921 oil Substances 0.000 description 33
- 238000000605 extraction Methods 0.000 description 17
- 238000003756 stirring Methods 0.000 description 12
- 238000004517 catalytic hydrocracking Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 238000006477 desulfuration reaction Methods 0.000 description 7
- 230000023556 desulfurization Effects 0.000 description 7
- RDCTYOLAEUHRGG-UHFFFAOYSA-M diethyl phosphate;tributyl(ethyl)phosphanium Chemical compound CCOP([O-])(=O)OCC.CCCC[P+](CC)(CCCC)CCCC RDCTYOLAEUHRGG-UHFFFAOYSA-M 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000356 contaminant Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000005987 sulfurization reaction Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 230000008929 regeneration Effects 0.000 description 3
- 238000011069 regeneration method Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000011143 downstream manufacturing Methods 0.000 description 2
- 238000004231 fluid catalytic cracking Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000006902 nitrogenation reaction Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002038 chemiluminescence detection Methods 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000126 substance 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/06—Metal salts, or metal salts deposited on a carrier
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/24—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/02—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents with two or more solvents, which are introduced or withdrawn separately
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/08—Inorganic compounds only
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
- C10G21/28—Recovery of used solvent
-
- 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
- C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
- C10G31/08—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by treating with water
-
- 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
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1074—Vacuum distillates
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Gas Separation By Absorption (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261666047P | 2012-06-29 | 2012-06-29 | |
| US61/666,047 | 2012-06-29 | ||
| US13/899,670 US20140001099A1 (en) | 2012-06-29 | 2013-05-22 | Process for removing sulfur compounds from vacuum gas oil |
| US13/899,670 | 2013-05-22 | ||
| PCT/US2013/045157 WO2014004076A1 (en) | 2012-06-29 | 2013-06-11 | Process for removing sulfur compounds from vacuum gas oil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2868877A1 true CA2868877A1 (en) | 2014-01-03 |
Family
ID=49777023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2868877A Abandoned CA2868877A1 (en) | 2012-06-29 | 2013-06-11 | Process for removing sulfur compounds from vacuum gas oil |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9068127B2 (enExample) |
| EP (1) | EP2867340A4 (enExample) |
| JP (1) | JP2015527435A (enExample) |
| KR (1) | KR20150015482A (enExample) |
| CN (1) | CN104411803A (enExample) |
| CA (1) | CA2868877A1 (enExample) |
| IN (1) | IN2014DN07957A (enExample) |
| MX (1) | MX2014012935A (enExample) |
| SG (1) | SG11201407308WA (enExample) |
| WO (1) | WO2014004076A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9068127B2 (en) | 2012-06-29 | 2015-06-30 | Uop Llc | Process for removing sulfur compounds from vacuum gas oil |
| KR102295397B1 (ko) * | 2015-06-18 | 2021-08-30 | 에스케이이노베이션 주식회사 | 이온성 액체 및 이를 포함하는 윤활제 조성물 |
| CN110564444A (zh) * | 2019-10-21 | 2019-12-13 | 河北工业大学 | 一种采用离子液体作为萃取剂的汽油脱硫方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10155281A1 (de) | 2001-11-08 | 2003-06-05 | Solvent Innovation Gmbh | Verfahren zur Entfernung polarisierbarer Verunreinigungen aus Kohlenwasserstoffen und Kohlenwasserstoffgemischen durch Extraktion mit ionischen Flüssigkeiten |
| WO2003040264A1 (en) | 2001-11-06 | 2003-05-15 | Extractica, Llc | Method for extraction of organosulfur compounds from hydrocarbons using ionic liquids |
| FR2840916B1 (fr) | 2002-06-17 | 2004-08-20 | Inst Francais Du Petrole | Procede d'elimination des composes soufres et azotes de coupes hydrocarbonees |
| US7749377B2 (en) * | 2007-11-14 | 2010-07-06 | Uop Llc | Methods of denitrogenating diesel fuel |
| US20100270211A1 (en) * | 2009-04-27 | 2010-10-28 | Saudi Arabian Oil Company | Desulfurization and denitrogenation with ionic liquids and metal ion systems |
| US8580107B2 (en) | 2009-12-30 | 2013-11-12 | Uop Llc | Process for removing sulfur from vacuum gas oil |
| US8608943B2 (en) | 2009-12-30 | 2013-12-17 | Uop Llc | Process for removing nitrogen from vacuum gas oil |
| US9068127B2 (en) | 2012-06-29 | 2015-06-30 | Uop Llc | Process for removing sulfur compounds from vacuum gas oil |
-
2013
- 2013-03-12 US US13/796,881 patent/US9068127B2/en active Active
- 2013-05-22 US US13/899,670 patent/US20140001099A1/en not_active Abandoned
- 2013-06-11 KR KR1020147033261A patent/KR20150015482A/ko not_active Ceased
- 2013-06-11 JP JP2015520241A patent/JP2015527435A/ja active Pending
- 2013-06-11 SG SG11201407308WA patent/SG11201407308WA/en unknown
- 2013-06-11 CN CN201380033289.0A patent/CN104411803A/zh active Pending
- 2013-06-11 EP EP13810701.6A patent/EP2867340A4/en not_active Withdrawn
- 2013-06-11 WO PCT/US2013/045157 patent/WO2014004076A1/en not_active Ceased
- 2013-06-11 MX MX2014012935A patent/MX2014012935A/es unknown
- 2013-06-11 IN IN7957DEN2014 patent/IN2014DN07957A/en unknown
- 2013-06-11 CA CA2868877A patent/CA2868877A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US9068127B2 (en) | 2015-06-30 |
| WO2014004076A1 (en) | 2014-01-03 |
| IN2014DN07957A (enExample) | 2015-05-01 |
| MX2014012935A (es) | 2015-02-10 |
| EP2867340A4 (en) | 2016-01-20 |
| EP2867340A1 (en) | 2015-05-06 |
| KR20150015482A (ko) | 2015-02-10 |
| SG11201407308WA (en) | 2014-12-30 |
| JP2015527435A (ja) | 2015-09-17 |
| CN104411803A (zh) | 2015-03-11 |
| US20140001099A1 (en) | 2014-01-02 |
| US20140001088A1 (en) | 2014-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140917 |
|
| FZDE | Discontinued |
Effective date: 20170613 |