CN101402877B - 一种汽油的催化氧化脱硫方法 - Google Patents
一种汽油的催化氧化脱硫方法 Download PDFInfo
- Publication number
- CN101402877B CN101402877B CN2008101586471A CN200810158647A CN101402877B CN 101402877 B CN101402877 B CN 101402877B CN 2008101586471 A CN2008101586471 A CN 2008101586471A CN 200810158647 A CN200810158647 A CN 200810158647A CN 101402877 B CN101402877 B CN 101402877B
- Authority
- CN
- China
- Prior art keywords
- gasoline
- phase
- catalyst
- transfer catalyst
- oil
- 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
- 238000006477 desulfuration reaction Methods 0.000 title claims abstract description 36
- 239000003502 gasoline Substances 0.000 title claims abstract description 29
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 27
- 230000003647 oxidation Effects 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 21
- 230000003197 catalytic effect Effects 0.000 title claims abstract description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 45
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 230000023556 desulfurization Effects 0.000 claims abstract description 35
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 18
- 235000019253 formic acid Nutrition 0.000 claims abstract description 18
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 18
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims abstract description 7
- 239000012028 Fenton's reagent Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 3
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 3
- 239000007800 oxidant agent Substances 0.000 claims abstract description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 35
- 239000005864 Sulphur Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000012071 phase Substances 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical group O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 claims description 10
- 229910000359 iron(II) sulfate Inorganic materials 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 9
- 230000001590 oxidative effect Effects 0.000 claims description 8
- -1 hydroxyl radical free radical Chemical class 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- OCVZNQCDPKRNDL-UHFFFAOYSA-N 2-hydroxyethyl-dimethyl-octadecylazanium;nitrate Chemical compound [O-][N+]([O-])=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCO OCVZNQCDPKRNDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- JBIROUFYLSSYDX-UHFFFAOYSA-M benzododecinium chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 JBIROUFYLSSYDX-UHFFFAOYSA-M 0.000 claims description 3
- 238000005191 phase separation Methods 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- NAPSCFZYZVSQHF-UHFFFAOYSA-N dimantine Chemical compound CCCCCCCCCCCCCCCCCCN(C)C NAPSCFZYZVSQHF-UHFFFAOYSA-N 0.000 claims 1
- 230000009467 reduction Effects 0.000 abstract description 2
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 42
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 8
- 150000003457 sulfones Chemical class 0.000 description 8
- 229930192474 thiophene Natural products 0.000 description 8
- 239000002283 diesel fuel Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000295 fuel oil Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000007600 charging Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910001182 Mo alloy Inorganic materials 0.000 description 1
- 230000010718 Oxidation Activity Effects 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical compound OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003009 desulfurizing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Description
Claims (4)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008101586471A CN101402877B (zh) | 2008-11-07 | 2008-11-07 | 一种汽油的催化氧化脱硫方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2008101586471A CN101402877B (zh) | 2008-11-07 | 2008-11-07 | 一种汽油的催化氧化脱硫方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101402877A CN101402877A (zh) | 2009-04-08 |
CN101402877B true CN101402877B (zh) | 2011-12-21 |
Family
ID=40537047
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2008101586471A Active CN101402877B (zh) | 2008-11-07 | 2008-11-07 | 一种汽油的催化氧化脱硫方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101402877B (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5171384B2 (ja) * | 2008-05-14 | 2013-03-27 | Jx日鉱日石エネルギー株式会社 | 脱硫装置及び燃料電池システム |
CN102311778A (zh) * | 2011-08-22 | 2012-01-11 | 浙江工业大学 | 一种汽油的氧化萃取脱硫方法 |
CN102604667B (zh) * | 2012-03-07 | 2014-07-09 | 中国科学院山西煤炭化学研究所 | 一种燃油萃取-催化氧化脱硫的方法 |
CN104293387B (zh) * | 2014-09-24 | 2016-01-13 | 中国石油化工股份有限公司 | 一种催化裂化汽油氧化脱硫的方法 |
CN104741122A (zh) * | 2015-03-11 | 2015-07-01 | 常州大学 | 一种用于氧化脱硫的催化剂的制备方法 |
CN107189813A (zh) * | 2017-07-19 | 2017-09-22 | 沈阳永润石油制品有限公司 | 一种国ⅴ标准的汽油脱硫方法 |
CN108728201B (zh) * | 2018-06-22 | 2021-03-23 | 山西焦煤集团有限责任公司 | 一种微波辅助催化臭氧液相氧化高硫煤脱硫方法 |
CN108753408B (zh) * | 2018-06-22 | 2023-12-19 | 山西焦煤集团有限责任公司 | 一种催化臭氧液相氧化高硫煤脱硫方法 |
CN108753407A (zh) * | 2018-06-22 | 2018-11-06 | 山西焦煤集团有限责任公司 | 一种煤炭氧化脱除有机硫的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101108761A (zh) * | 2006-07-18 | 2008-01-23 | 扬州大学 | 含油污水处理工艺及其设备 |
CN101139130A (zh) * | 2007-08-24 | 2008-03-12 | 华中师范大学 | 持续长效、不需双氧水的Fenton试剂的制备方法 |
CN101155900A (zh) * | 2005-02-15 | 2008-04-02 | 塞尔富可股份有限公司 | 通过超声波和微波联合处理提高石油的品位 |
-
2008
- 2008-11-07 CN CN2008101586471A patent/CN101402877B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101155900A (zh) * | 2005-02-15 | 2008-04-02 | 塞尔富可股份有限公司 | 通过超声波和微波联合处理提高石油的品位 |
CN101108761A (zh) * | 2006-07-18 | 2008-01-23 | 扬州大学 | 含油污水处理工艺及其设备 |
CN101139130A (zh) * | 2007-08-24 | 2008-03-12 | 华中师范大学 | 持续长效、不需双氧水的Fenton试剂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN101402877A (zh) | 2009-04-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101402877B (zh) | 一种汽油的催化氧化脱硫方法 | |
Lin et al. | Study on ultrasound-assisted oxidative desulfurization for crude oil | |
US7758745B2 (en) | Diesel desulfurization method | |
Rang et al. | Advances in desulfurization research of liquid fuel | |
CN101220293B (zh) | 离子液体萃取-催化氧化脱硫的方法 | |
TW201204825A (en) | A method for removing sulfides from a liquid fossil fuel and the device using the same | |
CN108192655A (zh) | 一种萃取脱除原油中含硫化合物的方法 | |
CN100556992C (zh) | 石油产品的一种催化氧化脱硫方法 | |
CN101173180B (zh) | 磷钨杂多季铵盐脱硫剂及其制备方法 | |
CN101333455A (zh) | 一种汽油的催化氧化萃取脱硫方法 | |
CN101173192B (zh) | 一种柴油脱硫的方法 | |
CN101302442A (zh) | 一种协同催化氧化脱除催化裂化柴油中硫化物的方法 | |
CN101967389A (zh) | 一种直接从页岩油中脱除碱性氮化合物的脱氮剂 | |
CN1253536C (zh) | 石油馏分油催化氧化脱硫法 | |
CN103184068B (zh) | 一种双氧水-盐酸氧化脱硫方法 | |
CN101381625A (zh) | 高含量芳烃油品中脱除硫化物的方法 | |
CA3205243A1 (en) | Catalytic carbon fiber preparation methods | |
CN106635127A (zh) | 一种催化氧化脱除燃料油中有机硫化物的方法 | |
CN101143746A (zh) | 一种含硫废碱液的处理方法 | |
CN102732287B (zh) | 一种燃油超深度脱硫方法 | |
CN101063044B (zh) | 一种柴油氧化脱硫方法 | |
CN101302441A (zh) | 利用氧化萃取脱除催化裂化汽油中硫化物的方法 | |
CN109722271B (zh) | 一种降低轻质油品的硫醇含量的方法 | |
CN112225185B (zh) | 一种烷基化废硫酸的回收方法 | |
US11517889B2 (en) | Catalytic carbon fiber contactor |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: KENLI OCEAN GRAND CHEMICALS CO., LTD. Free format text: FORMER OWNER: SHANDONG UNIVERSITY Effective date: 20120928 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 250012 JINAN, SHANDONG PROVINCE TO: 257506 DONGYING, SHANDONG PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20120928 Address after: 257506, Shandong County, Kenli Province, Tuo Town, Cui Village, 1000 meters south Patentee after: Kenli Sea Chemical Co.,Ltd. Address before: 250012 No. 44 West Wenhua Road, Lixia District, Shandong, Ji'nan Patentee before: Shandong University |
|
CP03 | Change of name, title or address |
Address after: 257506 1000m south of Cuijia village, Shengtuo Town, Kenli County, Dongying City, Shandong Province Patentee after: Dongying Hai Hai Chemical Co.,Ltd. Address before: 257506 1000m south of Cuijia village, Shengtuo Town, Kenli County, Shandong Province Patentee before: Kenli Sea Chemical Co.,Ltd. |
|
CP03 | Change of name, title or address | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20211025 Address after: 257506 1000m south of Cuijia village, Shengtuo Town, Kenli County, Dongying City, Shandong Province Patentee after: Dongying Chengyou Chemical Co.,Ltd. Address before: 257506 1000m south of Cuijia village, Shengtuo Town, Kenli County, Dongying City, Shandong Province Patentee before: Dongying Hai Hai Chemical Co.,Ltd. |