JP2003531922A5 - - Google Patents
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- Publication number
- JP2003531922A5 JP2003531922A5 JP2001558173A JP2001558173A JP2003531922A5 JP 2003531922 A5 JP2003531922 A5 JP 2003531922A5 JP 2001558173 A JP2001558173 A JP 2001558173A JP 2001558173 A JP2001558173 A JP 2001558173A JP 2003531922 A5 JP2003531922 A5 JP 2003531922A5
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- extractive distillation
- stream
- sulfolane
- sulfur
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 description 33
- 239000002904 solvent Substances 0.000 description 26
- 238000000895 extractive distillation Methods 0.000 description 17
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- 150000001336 alkenes Chemical class 0.000 description 10
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 10
- 239000007791 liquid phase Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000003464 sulfur compounds Chemical class 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 description 3
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- -1 polycyclic aromatic compounds Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 1
- YBJCDTIWNDBNTM-UHFFFAOYSA-N 1-methylsulfonylethane Chemical compound CCS(C)(=O)=O YBJCDTIWNDBNTM-UHFFFAOYSA-N 0.000 description 1
- DCALJVULAGICIX-UHFFFAOYSA-N 1-propylpyrrolidin-2-one Chemical compound CCCN1CCCC1=O DCALJVULAGICIX-UHFFFAOYSA-N 0.000 description 1
- WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 1
- SOZYDBBOFTUUPT-UHFFFAOYSA-N 3-ethylthiolane 1,1-dioxide Chemical compound CCC1CCS(=O)(=O)C1 SOZYDBBOFTUUPT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 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
- 239000012530 fluid Substances 0.000 description 1
- 238000004231 fluid catalytic cracking Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- 125000003367 polycyclic group Chemical group 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical class C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18202200P | 2000-02-11 | 2000-02-11 | |
| US60/182,022 | 2000-02-11 | ||
| US09/686,889 | 2000-10-12 | ||
| US09/686,889 US6551502B1 (en) | 2000-02-11 | 2000-10-12 | Process of removing sulfur compounds from gasoline |
| PCT/US2000/031223 WO2001059033A1 (en) | 2000-02-11 | 2000-11-15 | Process of removing sulfur compounds from gasoline |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003531922A JP2003531922A (ja) | 2003-10-28 |
| JP2003531922A5 true JP2003531922A5 (enExample) | 2011-01-06 |
| JP4828762B2 JP4828762B2 (ja) | 2011-11-30 |
Family
ID=26877723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001558173A Expired - Lifetime JP4828762B2 (ja) | 2000-02-11 | 2000-11-15 | ガソリンから硫黄化合物を除去する方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6551502B1 (enExample) |
| EP (1) | EP1294826B1 (enExample) |
| JP (1) | JP4828762B2 (enExample) |
| KR (1) | KR20030025905A (enExample) |
| CN (1) | CN1307289C (enExample) |
| AR (1) | AR027409A1 (enExample) |
| AT (1) | ATE407188T1 (enExample) |
| AU (1) | AU2001214883A1 (enExample) |
| CO (1) | CO5200812A1 (enExample) |
| DE (1) | DE60040171D1 (enExample) |
| TW (1) | TW541333B (enExample) |
| WO (1) | WO2001059033A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7326333B2 (en) * | 2001-12-20 | 2008-02-05 | Uop Llc | Apparatus and process for extracting sulfur compounds from a hydrocarbon stream |
| FR2847260B1 (fr) * | 2002-11-14 | 2006-07-14 | Inst Francais Du Petrole | Procede de desulfuration comprenant une etape d'hydrogenation selective des diolefines et une etape d'extraction des composes soufres |
| FR2892126B1 (fr) * | 2005-10-19 | 2010-04-30 | Inst Francais Du Petrole | Procede de conversion directe d'une charge comprenant des olefines a quatre, et/ou cinq atomes de carbone, pour la production de propylene avec une co-production d'essence desulfuree |
| CN102036726B (zh) | 2008-03-25 | 2013-07-03 | 台湾中油股份有限公司 | 改进的使用水溶性萃取溶剂的萃取蒸馏方法 |
| KR100992606B1 (ko) | 2008-05-08 | 2010-11-08 | 에스케이에너지 주식회사 | 용매추출에 의한 접촉분해경유에 포함된 산화황화합물의분리방법 |
| US8419930B2 (en) * | 2009-01-21 | 2013-04-16 | Beijing Grand Golden-Bright Engineering & Technologies Co., Ltd. | System for preparing high-quality gasoline through component oil refining hydrocarbon recombination hydrogenation and method thereof |
| US8246811B2 (en) * | 2009-05-26 | 2012-08-21 | IFP Energies Nouvelles | Process for the production of a hydrocarbon fraction with a high octane number and a low sulfur content |
| US8362313B2 (en) | 2009-07-17 | 2013-01-29 | Gtc Technology, Lp | Processes and systems for recovery of styrene from a styrene-containing feedstock |
| CN102557852B (zh) * | 2010-12-17 | 2014-06-04 | 中国石油天然气股份有限公司 | 一种萃取脱除炼厂碳四中二甲基二硫醚的方法 |
| CN102788505B (zh) * | 2011-05-20 | 2014-12-17 | 中国石油化工集团公司 | 一种重沸与进料加热二合一的加热炉及其分馏方法 |
| EP2737022B1 (en) | 2011-07-29 | 2017-10-04 | Saudi Arabian Oil Company | Selective middle distillate hydrotreating process |
| US9440947B2 (en) * | 2012-02-26 | 2016-09-13 | Amt International, Inc. | Regeneration of selective solvents for extractive processes |
| CN103361118B (zh) * | 2012-04-01 | 2015-04-29 | 中国石油化工股份有限公司 | 一种从含有烯烃和硫化物的汽油中回收芳烃的方法 |
| MY173216A (en) * | 2012-08-09 | 2020-01-06 | Council Scient Ind Res | Process for production of benzene lean gasoline by recovery of high purity benzene from unprocessed cracked gasoline fraction containing organic peroxides |
| CN102898286A (zh) * | 2012-08-21 | 2013-01-30 | 九江齐鑫化工有限公司 | 一种吸附蒸馏脱除mtbe中硫化物的方法 |
| SG11201509166QA (en) * | 2013-07-02 | 2016-01-28 | Saudi Basic Ind Corp | Method of producing aromatics and light olefins from a hydrocarbon feedstock |
| CN103555359B (zh) * | 2013-11-18 | 2015-04-22 | 郝天臻 | 一种催化裂化汽油的深度脱硫方法 |
| CN103725323A (zh) * | 2014-01-21 | 2014-04-16 | 湖北金鹤化工有限公司 | 一种生产低硫汽油的脱臭-萃取-洗涤-加氢组合工艺 |
| CN103740406A (zh) * | 2014-01-21 | 2014-04-23 | 湖北金鹤化工有限公司 | 一种生产低硫汽油的萃取-加氢组合工艺 |
| SG11201606522WA (en) | 2014-02-25 | 2016-09-29 | Saudi Basic Ind Corp | Process for producing btx from a mixed hydrocarbon source using coking |
| EP3110921B1 (en) | 2014-02-25 | 2018-05-23 | Saudi Basic Industries Corporation | Process for producing btx from a mixed hydrocarbon source using catalytic cracking |
| JP6554111B2 (ja) | 2014-02-25 | 2019-07-31 | サウディ ベーシック インダストリーズ コーポレイション | 熱分解を利用した、混合炭化水素元からｂｔｘを製造する方法 |
| US9890336B2 (en) | 2014-09-17 | 2018-02-13 | Exxonmobil Chemical Patents Inc. | Method and apparatus for the purification of a hydrocarbon-containing stream |
| CN104371755B (zh) * | 2014-11-19 | 2016-05-18 | 大连龙泰科技发展有限公司 | 一种凝析油脱硫的方法 |
| CN105238441B (zh) * | 2015-09-30 | 2017-06-13 | 中国石油大学(北京) | 一种对汽油进行深度脱硫的方法 |
| CN105296000B (zh) * | 2015-09-30 | 2017-07-11 | 中国石油大学(北京) | 一种催化裂化汽油脱硫的耦合方法 |
| CN105154132B (zh) * | 2015-09-30 | 2017-08-08 | 中国石油大学(北京) | 一种汽油脱硫方法 |
| CN105255515B (zh) * | 2015-09-30 | 2017-04-26 | 中国石油大学(北京) | 一种生产超低硫汽油的组合方法 |
| CN107779220B (zh) * | 2016-08-25 | 2019-11-29 | 北京安耐吉能源工程技术有限公司 | 一种汽油加工方法 |
| CN111218301A (zh) * | 2016-10-28 | 2020-06-02 | 中国石油化工股份有限公司 | 一种用于含硫原料的深度脱硫的抽提溶剂 |
| CN106381168B (zh) * | 2016-11-16 | 2018-06-15 | 郝智敏 | 一种满足最大轻汽油醚化降烯烃需求的催化汽油脱硫方法 |
| CN106520198B (zh) * | 2016-11-16 | 2018-08-10 | 郝天臻 | 一种兼具烯烃选择性脱除功能的催化汽油脱硫方法 |
| US10822549B2 (en) | 2019-01-18 | 2020-11-03 | Baker Hughes Holdings Llc | Methods and compounds for removing non-acidic contaminants from hydrocarbon streams |
| US20240132787A1 (en) * | 2022-10-05 | 2024-04-25 | Baker Hughes Oilfield Operations Llc | Sulfur extraction from hydrocarbons using carbonate-based solvents |
| CN119463915A (zh) * | 2023-08-11 | 2025-02-18 | 中国石油化工股份有限公司 | 催化裂化汽油富苯液中苯的回收方法和回收系统 |
| WO2025046431A1 (en) * | 2023-08-25 | 2025-03-06 | Sabic Global Technologies B.V. | Methods and systems for selective c5 valorization |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2285696A (en) | 1940-08-26 | 1942-06-09 | Shell Dev | Process for desulphurizing mineral oil distillates |
| US2455803A (en) | 1944-02-11 | 1948-12-07 | Shell Dev | Extractive distillation process |
| US2634230A (en) | 1949-11-29 | 1953-04-07 | Standard Oil Co | Desulfurization of olefinic naphtha |
| US2849514A (en) * | 1955-04-21 | 1958-08-26 | Standard Oil Co | Extraction of hydrocarbon mixtures with hydroxy sulfones |
| NL277129A (enExample) | 1961-04-14 | |||
| US3472909A (en) * | 1967-02-27 | 1969-10-14 | Universal Oil Prod Co | Process for producing olefinic hydrocarbons |
| US3470088A (en) * | 1967-11-06 | 1969-09-30 | Universal Oil Prod Co | Method for aromatic hydrocarbon recovery |
| US3640818A (en) * | 1969-10-31 | 1972-02-08 | Exxon Research Engineering Co | Hydroforming naphthas |
| US4035285A (en) * | 1974-05-28 | 1977-07-12 | Mobil Oil Corporation | Hydrocarbon conversion process |
| US4053369A (en) | 1974-05-30 | 1977-10-11 | Phillips Petroleum Company | Extractive distillation |
| CA1053601A (en) * | 1974-05-30 | 1979-05-01 | Martin R. Cines | Extractive distillation |
| US4097371A (en) * | 1976-09-21 | 1978-06-27 | Phillips Petroleum Company | Separation of fluid mixtures |
| US5302282A (en) * | 1990-08-17 | 1994-04-12 | Uop | Integrated process for the production of high quality lube oil blending stock |
| US5360532A (en) | 1991-08-15 | 1994-11-01 | Mobil Oil Corporation | Gasoline upgrading process |
| US5320741A (en) * | 1992-04-09 | 1994-06-14 | Stone & Webster Engineering Corporation | Combination process for the pretreatment and hydroconversion of heavy residual oils |
| CN1035775C (zh) * | 1994-03-28 | 1997-09-03 | 中国石油化工总公司 | 催化裂解汽油加氢精制方法 |
| US5582714A (en) | 1995-03-20 | 1996-12-10 | Uop | Process for the removal of sulfur from petroleum fractions |
| DE19603901A1 (de) * | 1996-02-03 | 1997-08-07 | Krupp Uhde Gmbh | Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens |
| ZA972966B (en) * | 1996-05-21 | 1997-11-21 | Glitsch Int Inc | Recovery of styrene from purolysis gasoline by extractive distillation. |
| US6228254B1 (en) * | 1999-06-11 | 2001-05-08 | Chevron U.S.A., Inc. | Mild hydrotreating/extraction process for low sulfur gasoline |
| US6358402B1 (en) | 1999-12-28 | 2002-03-19 | Exxonmobil Research And Engineering Company | Extractive distillation process for the reduction of sulfur species in hydrocarbons streams |
-
2000
- 2000-10-12 US US09/686,889 patent/US6551502B1/en not_active Expired - Lifetime
- 2000-11-15 AT AT00977214T patent/ATE407188T1/de not_active IP Right Cessation
- 2000-11-15 EP EP00977214A patent/EP1294826B1/en not_active Expired - Lifetime
- 2000-11-15 AU AU2001214883A patent/AU2001214883A1/en not_active Abandoned
- 2000-11-15 CN CNB008194084A patent/CN1307289C/zh not_active Expired - Lifetime
- 2000-11-15 KR KR1020027010406A patent/KR20030025905A/ko not_active Withdrawn
- 2000-11-15 DE DE60040171T patent/DE60040171D1/de not_active Expired - Lifetime
- 2000-11-15 JP JP2001558173A patent/JP4828762B2/ja not_active Expired - Lifetime
- 2000-11-15 WO PCT/US2000/031223 patent/WO2001059033A1/en not_active Ceased
- 2000-11-29 TW TW089125335A patent/TW541333B/zh not_active IP Right Cessation
- 2000-11-30 CO CO00091760A patent/CO5200812A1/es unknown
-
2001
- 2001-02-09 AR ARP010100617A patent/AR027409A1/es unknown
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