JP2003327970A - 硫黄およびメルカプタンの含量の低い炭化水素を製造する方法 - Google Patents
硫黄およびメルカプタンの含量の低い炭化水素を製造する方法Info
- Publication number
- JP2003327970A JP2003327970A JP2003090289A JP2003090289A JP2003327970A JP 2003327970 A JP2003327970 A JP 2003327970A JP 2003090289 A JP2003090289 A JP 2003090289A JP 2003090289 A JP2003090289 A JP 2003090289A JP 2003327970 A JP2003327970 A JP 2003327970A
- Authority
- JP
- Japan
- Prior art keywords
- desulfurization
- sulfur
- gasoline
- liter
- hydrogen
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 61
- 230000008569 process Effects 0.000 title claims abstract description 29
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 23
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 23
- 239000011593 sulfur Substances 0.000 title abstract description 59
- 229910052717 sulfur Inorganic materials 0.000 title abstract description 59
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract description 58
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000006477 desulfuration reaction Methods 0.000 claims abstract description 81
- 230000023556 desulfurization Effects 0.000 claims abstract description 81
- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 22
- 150000003464 sulfur compounds Chemical class 0.000 claims abstract description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 16
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000926 separation method Methods 0.000 claims abstract description 13
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 7
- -1 olefin compounds Chemical class 0.000 claims abstract description 6
- 150000001993 dienes Chemical class 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 230000000737 periodic effect Effects 0.000 claims description 9
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims description 7
- 239000011733 molybdenum Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 238000004523 catalytic cracking Methods 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910021472 group 8 element Inorganic materials 0.000 claims description 5
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- 238000004939 coking Methods 0.000 claims description 2
- 238000004230 steam cracking Methods 0.000 claims description 2
- 230000003009 desulfurizing effect Effects 0.000 abstract description 5
- 150000002431 hydrogen Chemical class 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 150000001336 alkenes Chemical class 0.000 description 29
- 238000005984 hydrogenation reaction Methods 0.000 description 13
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910018921 CoO 3 Inorganic materials 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical compound N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
- 229910001981 cobalt nitrate Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide 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
- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
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)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0204108 | 2002-03-29 | ||
| FR0204108A FR2837831B1 (fr) | 2002-03-29 | 2002-03-29 | Procede de production d'hydrocarbures a faible teneur en soufre et en mercaptans |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003327970A true JP2003327970A (ja) | 2003-11-19 |
| JP2003327970A5 JP2003327970A5 (enExample) | 2006-05-18 |
Family
ID=27839409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003090289A Pending JP2003327970A (ja) | 2002-03-29 | 2003-03-28 | 硫黄およびメルカプタンの含量の低い炭化水素を製造する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20030217951A1 (enExample) |
| EP (1) | EP1354930A1 (enExample) |
| JP (1) | JP2003327970A (enExample) |
| CN (1) | CN1448481A (enExample) |
| FR (1) | FR2837831B1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007177245A (ja) * | 2005-12-22 | 2007-07-12 | Inst Fr Petrole | 硫化触媒を利用する選択的水素化法 |
| JP2007182567A (ja) * | 2005-12-22 | 2007-07-19 | Inst Fr Petrole | 特定の担体を有する触媒を利用する選択的水素化法 |
| WO2009048041A1 (ja) * | 2007-10-12 | 2009-04-16 | Nippon Oil Corporation | ガソリン基材の製造方法及びガソリン |
| JP2013209650A (ja) * | 2012-03-29 | 2013-10-10 | IFP Energies Nouvelles | ガソリンの選択的水素化方法 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7785461B2 (en) * | 2004-11-10 | 2010-08-31 | Petroleo Brasileiro S.A. - Petrobras | Process for selective hydrodesulfurization of naphtha |
| BRPI0601787B1 (pt) * | 2006-05-17 | 2016-06-07 | Petroleo Brasileiro Sa | processo de hidrodessulfurização seletiva de nafta |
| US8461293B2 (en) | 2010-08-03 | 2013-06-11 | Chevron Phillips Chemical Company Lp | Methods of mercaptanizing olefinic hydrocarbons and compositions produced therefrom |
| CN102533330B (zh) * | 2010-12-31 | 2014-05-28 | 中国石油化工股份有限公司 | 一种生产低硫汽油的方法 |
| CN102604672B (zh) * | 2011-01-20 | 2014-05-28 | 中国石油化工股份有限公司 | 一种低硫汽油的生产方法 |
| CN102634368B (zh) * | 2011-02-10 | 2014-08-06 | 中国石油天然气股份有限公司 | 一种劣质汽油改质的方法 |
| US8753504B2 (en) * | 2011-04-28 | 2014-06-17 | Battelle Memorial Institute | Systems and processes for removing elemental sulfur compounds from desulfurized fuels |
| US8821715B2 (en) * | 2011-05-24 | 2014-09-02 | Saudi Arabian Oil Company | Electrochemical promotion of catalysis in hydrodesulfurization processes |
| FR3014896B1 (fr) | 2013-12-18 | 2018-07-27 | IFP Energies Nouvelles | Procede d'hydrodesulfuration de coupes d'hydrocarbures |
| FR3057578B1 (fr) | 2016-10-19 | 2018-11-16 | IFP Energies Nouvelles | Procede d'hydrodesulfuration d'une essence olefinique. |
| US10655074B2 (en) | 2017-02-12 | 2020-05-19 | Mag{hacek over (e)}m{hacek over (a)} Technology LLC | Multi-stage process and device for reducing environmental contaminates in heavy marine fuel oil |
| US12071592B2 (en) | 2017-02-12 | 2024-08-27 | Magēmā Technology LLC | Multi-stage process and device utilizing structured catalyst beds and reactive distillation for the production of a low sulfur heavy marine fuel oil |
| US10604709B2 (en) | 2017-02-12 | 2020-03-31 | Magēmā Technology LLC | Multi-stage device and process for production of a low sulfur heavy marine fuel oil from distressed heavy fuel oil materials |
| US11788017B2 (en) | 2017-02-12 | 2023-10-17 | Magëmã Technology LLC | Multi-stage process and device for reducing environmental contaminants in heavy marine fuel oil |
| US12025435B2 (en) | 2017-02-12 | 2024-07-02 | Magēmã Technology LLC | Multi-stage device and process for production of a low sulfur heavy marine fuel oil |
| US12281266B2 (en) | 2017-02-12 | 2025-04-22 | Magẽmã Technology LLC | Heavy marine fuel oil composition |
| CN113546644B (zh) * | 2021-06-27 | 2022-05-27 | 昆明理工大学 | 焦炉煤气有机硫深度脱除催化剂的制备方法和应用 |
| FR3154412A1 (fr) * | 2023-10-24 | 2025-04-25 | Axens | Procede de traitement d’une essence de pyrolyse |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3349027A (en) * | 1965-02-08 | 1967-10-24 | Gulf Research Development Co | Multi-stage hydrodesulfurization process |
| US4562751A (en) * | 1984-01-06 | 1986-01-07 | Nason Clyde K | Solenoid drive apparatus for an external infusion pump |
| US4678408A (en) * | 1984-01-06 | 1987-07-07 | Pacesetter Infusion, Ltd. | Solenoid drive apparatus for an external infusion pump |
| US4685903A (en) * | 1984-01-06 | 1987-08-11 | Pacesetter Infusion, Ltd. | External infusion pump apparatus |
| JP3387700B2 (ja) * | 1995-07-26 | 2003-03-17 | 新日本石油株式会社 | 接触分解ガソリンの脱硫方法 |
| US6231753B1 (en) * | 1996-02-02 | 2001-05-15 | Exxon Research And Engineering Company | Two stage deep naphtha desulfurization with reduced mercaptan formation |
| US6692635B2 (en) * | 1999-02-24 | 2004-02-17 | Institut Francais Du Petrole | Process for the production of gasolines with low sulfur contents |
| US6303020B1 (en) * | 2000-01-07 | 2001-10-16 | Catalytic Distillation Technologies | Process for the desulfurization of petroleum feeds |
| FR2807061B1 (fr) * | 2000-03-29 | 2002-05-31 | Inst Francais Du Petrole | Procede de desulfuration d'essence comprenant une desulfuration des fractions lourde et intermediaire issues d'un fractionnement en au moins trois coupes |
| US6444118B1 (en) * | 2001-02-16 | 2002-09-03 | Catalytic Distillation Technologies | Process for sulfur reduction in naphtha streams |
-
2002
- 2002-03-29 FR FR0204108A patent/FR2837831B1/fr not_active Expired - Lifetime
-
2003
- 2003-03-13 EP EP03290618A patent/EP1354930A1/fr not_active Ceased
- 2003-03-28 JP JP2003090289A patent/JP2003327970A/ja active Pending
- 2003-03-29 CN CN03128651.8A patent/CN1448481A/zh active Pending
- 2003-03-31 US US10/402,152 patent/US20030217951A1/en not_active Abandoned
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007177245A (ja) * | 2005-12-22 | 2007-07-12 | Inst Fr Petrole | 硫化触媒を利用する選択的水素化法 |
| JP2007182567A (ja) * | 2005-12-22 | 2007-07-19 | Inst Fr Petrole | 特定の担体を有する触媒を利用する選択的水素化法 |
| WO2009048041A1 (ja) * | 2007-10-12 | 2009-04-16 | Nippon Oil Corporation | ガソリン基材の製造方法及びガソリン |
| JP2009096830A (ja) * | 2007-10-12 | 2009-05-07 | Nippon Oil Corp | ガソリン基材の製造方法及びガソリン |
| CN101821362A (zh) * | 2007-10-12 | 2010-09-01 | 新日本石油株式会社 | 汽油基材的制造方法及汽油 |
| US8303805B2 (en) | 2007-10-12 | 2012-11-06 | Nippon Oil Corporation | Process for producing gasoline base and gasoline |
| CN101821362B (zh) * | 2007-10-12 | 2013-04-24 | 新日本石油株式会社 | 汽油基材的制造方法及汽油 |
| JP2013209650A (ja) * | 2012-03-29 | 2013-10-10 | IFP Energies Nouvelles | ガソリンの選択的水素化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2837831B1 (fr) | 2005-02-11 |
| EP1354930A1 (fr) | 2003-10-22 |
| FR2837831A1 (fr) | 2003-10-03 |
| CN1448481A (zh) | 2003-10-15 |
| US20030217951A1 (en) | 2003-11-27 |
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