ES2645438T3 - Procedimiento para eliminar nitrógeno de corrientes de carburantes con líquidos iónicos de caprolactamio - Google Patents
Procedimiento para eliminar nitrógeno de corrientes de carburantes con líquidos iónicos de caprolactamio Download PDFInfo
- Publication number
- ES2645438T3 ES2645438T3 ES13770286.6T ES13770286T ES2645438T3 ES 2645438 T3 ES2645438 T3 ES 2645438T3 ES 13770286 T ES13770286 T ES 13770286T ES 2645438 T3 ES2645438 T3 ES 2645438T3
- Authority
- ES
- Spain
- Prior art keywords
- fuel
- ionic liquid
- caprolactam
- immiscible
- effluent
- 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.)
- Active
Links
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 152
- 239000000446 fuel Substances 0.000 title claims abstract description 147
- 238000000034 method Methods 0.000 title claims abstract description 53
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims description 222
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title description 159
- 229910052757 nitrogen Inorganic materials 0.000 title description 80
- 239000000203 mixture Substances 0.000 claims abstract description 26
- 150000002430 hydrocarbons Chemical class 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- 229930195733 hydrocarbon Natural products 0.000 claims description 33
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 31
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 31
- 239000004215 Carbon black (E152) Substances 0.000 claims description 26
- 230000008929 regeneration Effects 0.000 claims description 22
- 238000011069 regeneration method Methods 0.000 claims description 22
- 239000002283 diesel fuel Substances 0.000 claims description 21
- 238000000926 separation method Methods 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 5
- -1 nitrogenous compound Chemical class 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 description 20
- 238000000605 extraction Methods 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- 239000011593 sulfur Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 230000014509 gene expression Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004231 fluid catalytic cracking Methods 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- 238000004517 catalytic hydrocracking Methods 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000012864 cross contamination Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical compound [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052782 aluminium Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 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 group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003758 nuclear fuel Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000011064 split stream procedure 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
- 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
- C10G21/27—Organic compounds not provided for in a single one of groups C10G21/14 - C10G21/26
-
- 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
- C10G53/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes
- C10G53/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only
- C10G53/04—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one extraction step
- C10G53/06—Treatment of hydrocarbon oils, in the absence of hydrogen, by two or more refining processes plural serial stages only including at least one extraction step including only extraction steps, e.g. deasphalting by solvent treatment followed by extraction of aromatics
-
- 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)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/429,596 US8709236B2 (en) | 2012-03-26 | 2012-03-26 | Process for removing nitrogen from fuel streams with caprolactamium ionic liquids |
| US201213429596 | 2012-03-26 | ||
| PCT/US2013/032748 WO2013148387A1 (en) | 2012-03-26 | 2013-03-18 | Process for removing nitrogen from fuel streams with caprolactamium ionic liquids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2645438T3 true ES2645438T3 (es) | 2017-12-05 |
Family
ID=49210780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13770286.6T Active ES2645438T3 (es) | 2012-03-26 | 2013-03-18 | Procedimiento para eliminar nitrógeno de corrientes de carburantes con líquidos iónicos de caprolactamio |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8709236B2 (enExample) |
| EP (1) | EP2831202B1 (enExample) |
| JP (1) | JP2015515520A (enExample) |
| KR (1) | KR101645608B1 (enExample) |
| CN (1) | CN104204145B (enExample) |
| BR (1) | BR112014020503B1 (enExample) |
| CA (1) | CA2864852C (enExample) |
| DK (1) | DK2831202T3 (enExample) |
| ES (1) | ES2645438T3 (enExample) |
| IN (1) | IN2014DN06974A (enExample) |
| MX (1) | MX337384B (enExample) |
| SG (1) | SG11201404865TA (enExample) |
| WO (1) | WO2013148387A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9416071B2 (en) | 2014-05-06 | 2016-08-16 | Uop Llc | Hydrocarbon conversion processes using lactamium-based ionic liquids |
| US9233928B2 (en) * | 2014-05-06 | 2016-01-12 | Uop Llc | Synthesis of lactam based ionic liquid |
| US9192928B1 (en) | 2014-11-19 | 2015-11-24 | Uop Llc | Regeneration of an ionic liquid catalyst using metal complexes |
| US9475997B2 (en) | 2014-11-24 | 2016-10-25 | Uop Llc | Contaminant removal from hydrocarbon streams with carbenium pseudo ionic liquids |
| US9574139B2 (en) | 2014-11-24 | 2017-02-21 | Uop Llc | Contaminant removal from hydrocarbon streams with lewis acidic ionic liquids |
| US20160168483A1 (en) * | 2014-12-10 | 2016-06-16 | Uop Llc | Contaminant removal from kerosene streams with lactamium based ionic liquids |
| US20160168482A1 (en) * | 2014-12-12 | 2016-06-16 | Uop Llc | Contaminant removal from hydrocarbon streams with ionic liquids |
| US10384988B2 (en) | 2015-12-23 | 2019-08-20 | Uop Llc | Chloride management in ionic liquid alkylation processes |
Family Cites Families (9)
| 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 |
| US7749377B2 (en) * | 2007-11-14 | 2010-07-06 | Uop Llc | Methods of denitrogenating diesel fuel |
| EP2327734A4 (en) | 2008-09-03 | 2012-08-29 | Sumitomo Chemical Co | POLYMER CONNECTION AND LIGHT-EMITTING POLYMER ELEMENT THEREWITH |
| US8127938B2 (en) * | 2009-03-31 | 2012-03-06 | Uop Llc | Apparatus and process for treating a hydrocarbon stream |
| WO2011026972A1 (en) * | 2009-09-07 | 2011-03-10 | Shell Internationale Research Maatschappij B.V. | Process for the removal of aromatic compounds from a mixture |
| CN101709053A (zh) * | 2009-12-14 | 2010-05-19 | 河北瑞通美邦工程有限公司 | 一种己内酰胺制备工艺 |
| US8608943B2 (en) * | 2009-12-30 | 2013-12-17 | Uop Llc | Process for removing nitrogen from vacuum gas oil |
| US8758600B2 (en) * | 2010-03-26 | 2014-06-24 | Saudi Arabian Oil Company | Ionic liquid desulfurization process incorporated in a low pressure separator |
| CN101961598A (zh) * | 2010-09-02 | 2011-02-02 | 河北科技大学 | 一种使用离子液体吸收硫化氢气体的方法 |
-
2012
- 2012-03-26 US US13/429,596 patent/US8709236B2/en active Active
-
2013
- 2013-03-18 DK DK13770286.6T patent/DK2831202T3/da active
- 2013-03-18 JP JP2015503357A patent/JP2015515520A/ja not_active Withdrawn
- 2013-03-18 SG SG11201404865TA patent/SG11201404865TA/en unknown
- 2013-03-18 WO PCT/US2013/032748 patent/WO2013148387A1/en not_active Ceased
- 2013-03-18 CN CN201380016096.4A patent/CN104204145B/zh active Active
- 2013-03-18 EP EP13770286.6A patent/EP2831202B1/en active Active
- 2013-03-18 IN IN6974DEN2014 patent/IN2014DN06974A/en unknown
- 2013-03-18 KR KR1020147027359A patent/KR101645608B1/ko active Active
- 2013-03-18 ES ES13770286.6T patent/ES2645438T3/es active Active
- 2013-03-18 BR BR112014020503-5A patent/BR112014020503B1/pt active IP Right Grant
- 2013-03-18 MX MX2014011361A patent/MX337384B/es active IP Right Grant
- 2013-03-18 CA CA2864852A patent/CA2864852C/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN104204145B (zh) | 2015-11-25 |
| BR112014020503B1 (pt) | 2020-03-31 |
| CA2864852A1 (en) | 2013-10-03 |
| CA2864852C (en) | 2016-04-26 |
| MX337384B (es) | 2016-03-02 |
| CN104204145A (zh) | 2014-12-10 |
| KR101645608B1 (ko) | 2016-08-05 |
| MX2014011361A (es) | 2014-10-14 |
| EP2831202A1 (en) | 2015-02-04 |
| WO2013148387A1 (en) | 2013-10-03 |
| US8709236B2 (en) | 2014-04-29 |
| US20130248423A1 (en) | 2013-09-26 |
| SG11201404865TA (en) | 2014-09-26 |
| KR20140138238A (ko) | 2014-12-03 |
| JP2015515520A (ja) | 2015-05-28 |
| EP2831202B1 (en) | 2017-08-02 |
| DK2831202T3 (da) | 2017-11-13 |
| IN2014DN06974A (enExample) | 2015-04-10 |
| EP2831202A4 (en) | 2015-10-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2645438T3 (es) | Procedimiento para eliminar nitrógeno de corrientes de carburantes con líquidos iónicos de caprolactamio | |
| RU2510987C2 (ru) | Способ удаления металлов из вакуумного газойля | |
| RU2535668C2 (ru) | Способ удаления азота из вакуумного газойля | |
| US8580107B2 (en) | Process for removing sulfur from vacuum gas oil | |
| US8608951B2 (en) | Process for removing metals from crude oil | |
| CA2772431C (en) | Process for removing metals from resid | |
| US9328295B2 (en) | Extract recycle in a hydrocarbon decontamination process | |
| US9068127B2 (en) | Process for removing sulfur compounds from vacuum gas oil | |
| US20140291208A1 (en) | Process for regenerating ionic liquids by adding light hydrocarbon stream |