CA1094496A - Process for sweetening sour hydrocarbon distillates - Google Patents
Process for sweetening sour hydrocarbon distillatesInfo
- Publication number
- CA1094496A CA1094496A CA269,199A CA269199A CA1094496A CA 1094496 A CA1094496 A CA 1094496A CA 269199 A CA269199 A CA 269199A CA 1094496 A CA1094496 A CA 1094496A
- Authority
- CA
- Canada
- Prior art keywords
- quaternary ammonium
- hydrocarbon
- ammonium compound
- alkaline medium
- improved process
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 48
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 45
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 45
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 40
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 239000003610 charcoal Substances 0.000 claims abstract description 17
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 17
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 8
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 41
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000012071 phase Substances 0.000 claims description 15
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 13
- 230000001476 alcoholic effect Effects 0.000 claims description 11
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical group [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000000908 ammonium hydroxide Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 238000004064 recycling Methods 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000005194 fractionation Methods 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical group [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims 2
- 239000012530 fluid Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 238000011084 recovery Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 20
- 239000003502 gasoline Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 16
- 229940090044 injection Drugs 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003518 caustics Substances 0.000 description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 235000009508 confectionery Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 229940099408 Oxidizing agent Drugs 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229910017974 NH40H Inorganic materials 0.000 description 3
- 150000002019 disulfides Chemical class 0.000 description 3
- 125000005608 naphthenic acid group Chemical group 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003209 petroleum derivative Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- 241000428533 Rhis Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material 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
- C10G19/00—Refining hydrocarbon oils in the absence of hydrogen, by alkaline treatment
-
- 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
- C10G27/00—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation
- C10G27/04—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen
- C10G27/10—Refining of hydrocarbon oils in the absence of hydrogen, by oxidation with oxygen or compounds generating oxygen in the presence of metal-containing organic complexes, e.g. chelates, or cationic ion-exchange resins
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64885476A | 1976-01-14 | 1976-01-14 | |
| US648,854 | 1976-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094496A true CA1094496A (en) | 1981-01-27 |
Family
ID=24602499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA269,199A Expired CA1094496A (en) | 1976-01-14 | 1977-01-05 | Process for sweetening sour hydrocarbon distillates |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS52101206A (en:Method) |
| AU (1) | AU505893B2 (en:Method) |
| BR (1) | BR7700156A (en:Method) |
| CA (1) | CA1094496A (en:Method) |
| DE (1) | DE2700850C3 (en:Method) |
| ES (1) | ES455004A1 (en:Method) |
| FR (1) | FR2338322A1 (en:Method) |
| GB (1) | GB1566052A (en:Method) |
| IT (1) | IT1076210B (en:Method) |
| SU (1) | SU689623A3 (en:Method) |
| YU (1) | YU39982B (en:Method) |
| ZA (1) | ZA7740B (en:Method) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124494A (en) * | 1978-01-11 | 1978-11-07 | Uop Inc. | Treating a petroleum distillate with a supported metal phthalocyanine and an alkanolamine hydroxide |
| US4121997A (en) * | 1978-01-11 | 1978-10-24 | Uop Inc. | Treating a petroleum distillate with a supported metal phthalocyanine and an alkaline reagent containing alkanolamine halide |
| US4124493A (en) * | 1978-02-24 | 1978-11-07 | Uop Inc. | Catalytic oxidation of mercaptan in petroleum distillate including alkaline reagent and substituted ammonium halide |
| AU530970B2 (en) * | 1978-07-24 | 1983-08-04 | Uop Inc. | Catalytic composite |
| JPS5876786U (ja) * | 1981-11-18 | 1983-05-24 | 三菱鉛筆株式会社 | 筆記具 |
| JPS58190185U (ja) * | 1982-06-11 | 1983-12-17 | 三菱鉛筆株式会社 | 時計付き複式筆記具 |
| FR2594136B2 (fr) * | 1985-08-13 | 1988-11-04 | Inst Francais Du Petrole | Procede ameliore d'adoucissement de coupes petrolieres |
| FR2586253B1 (fr) * | 1985-08-13 | 1988-08-26 | Inst Francais Du Petrole | Procede ameliore d'adoucissement de coupes petrolieres |
| FR2619822B1 (fr) * | 1987-08-24 | 1990-01-12 | Inst Francais Du Petrole | Procede d'adoucissement en continu de coupes petrolieres en phase liquide |
| FR2635111B1 (fr) * | 1988-08-04 | 1990-09-28 | Inst Francais Du Petrole | Procede d'adoucissement en continu de coupes petrolieres |
| AU618886B2 (en) * | 1989-05-08 | 1992-01-09 | Uop | Caustic-free sweetening of sour hydrocarbon streams |
| US5683626A (en) * | 1995-08-25 | 1997-11-04 | Exxon Research And Engineering Company | Process for neutralization of petroleum acids |
| RU2106387C1 (ru) * | 1996-05-06 | 1998-03-10 | Акционерное общество открытого типа "ЛУКойл-Пермнефтеоргсинтез" | Способ демеркаптанизации нефтяных дистиллятов |
-
1977
- 1977-01-04 ZA ZA770040A patent/ZA7740B/xx unknown
- 1977-01-05 CA CA269,199A patent/CA1094496A/en not_active Expired
- 1977-01-07 AU AU21130/77A patent/AU505893B2/en not_active Expired
- 1977-01-11 DE DE2700850A patent/DE2700850C3/de not_active Expired
- 1977-01-11 BR BR7700156A patent/BR7700156A/pt unknown
- 1977-01-11 YU YU53/77A patent/YU39982B/xx unknown
- 1977-01-13 IT IT19265/77A patent/IT1076210B/it active
- 1977-01-13 JP JP282177A patent/JPS52101206A/ja active Granted
- 1977-01-13 ES ES455004A patent/ES455004A1/es not_active Expired
- 1977-01-13 GB GB1291/77A patent/GB1566052A/en not_active Expired
- 1977-01-14 SU SU772440296A patent/SU689623A3/ru active
- 1977-01-14 FR FR7701124A patent/FR2338322A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SU689623A3 (ru) | 1979-09-30 |
| DE2700850A1 (de) | 1977-07-21 |
| YU39982B (en) | 1985-06-30 |
| BR7700156A (pt) | 1977-09-06 |
| FR2338322A1 (fr) | 1977-08-12 |
| IT1076210B (it) | 1985-04-27 |
| DE2700850C3 (de) | 1981-02-05 |
| ES455004A1 (es) | 1977-12-16 |
| YU5377A (en) | 1982-05-31 |
| DE2700850B2 (de) | 1980-05-08 |
| GB1566052A (en) | 1980-04-30 |
| JPS52101206A (en) | 1977-08-25 |
| ZA7740B (en) | 1977-11-30 |
| AU505893B2 (en) | 1979-12-06 |
| JPS558116B2 (en:Method) | 1980-03-01 |
| AU2113077A (en) | 1978-07-13 |
| FR2338322B1 (en:Method) | 1980-03-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |