GB849998A - Process for sweetening sour hydrocarbon distillates - Google Patents
Process for sweetening sour hydrocarbon distillatesInfo
- Publication number
- GB849998A GB849998A GB4396/59A GB439659A GB849998A GB 849998 A GB849998 A GB 849998A GB 4396/59 A GB4396/59 A GB 4396/59A GB 439659 A GB439659 A GB 439659A GB 849998 A GB849998 A GB 849998A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkali
- air
- oils
- hydrocarbon distillates
- sweetening
- 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
- 239000004215 Carbon black (E152) Substances 0.000 title abstract 4
- 229930195733 hydrocarbon Natural products 0.000 title abstract 4
- 150000002430 hydrocarbons Chemical class 0.000 title abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 239000007789 gas Substances 0.000 abstract 2
- 239000010742 number 1 fuel oil Substances 0.000 abstract 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003849 aromatic solvent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [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 abstract 1
- 229930003836 cresol Natural products 0.000 abstract 1
- 239000010771 distillate fuel oil Substances 0.000 abstract 1
- 239000000446 fuel Substances 0.000 abstract 1
- 239000000295 fuel oil Substances 0.000 abstract 1
- 239000003502 gasoline Substances 0.000 abstract 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- -1 kerosenes Substances 0.000 abstract 1
- 239000010687 lubricating oil Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 239000001648 tannin Substances 0.000 abstract 1
- 235000018553 tannin Nutrition 0.000 abstract 1
- 229920001864 tannin Polymers 0.000 abstract 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
- 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
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)
Abstract
Metal phthalocyanines or their sulphonated or carboxylated derivatives are used to catalyse processes for sweetening sour hydrocarbon distillates with oxygen or a free oxygen-containing gas in the presence of an alkali. Suitable alkalis are aqueous sodium and potassium hydroxide solutions which may include a solutizer e.g. methanol, ethanol, phenol, a cresol, tannin or an isobutyrate. Air is the preferred free oxygen-containing gas. The process may be effected batchwise or continuously and at ambient or elevated temperature e.g. 38 to 205 DEG C. In a preferred process the alkali containing the catalyst is sprayed into the upper part of a sweetening zone, and the air and hydrocarbon are introduced into the lower and intermediate parts respectively. 50 to 95% of the mercaptans may first be removed by a conventional pretreatment e.g. with alkali which may contain solutizers. Hydrocarbon distillates mentioned are cracked, straight run and natural gasolines, naphthas, jet fuels, kerosenes, aromatic solvents, stove oils, range oils, and distillate fuel and lubricating oils. In examples a cracked gasoline, a kerosene, a fuel oil (184-272 DEG C.) and a light naphtha (168-205 DEG C.) are agitated with sodium or potassium hydroxide containing 50, 100 or 250 p.p.m. cobalt phthalocyanine disulphonate in the presence of air.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US714937A US2882224A (en) | 1958-02-13 | 1958-02-13 | Process for sweetening sour hydrocarbon distillates with metal phthalocyanine catalyst in the presence of alkali and air |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB849998A true GB849998A (en) | 1960-09-28 |
Family
ID=24872078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4396/59A Expired GB849998A (en) | 1958-02-13 | 1959-02-09 | Process for sweetening sour hydrocarbon distillates |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US2882224A (en) |
| BE (1) | BE575509A (en) |
| DE (1) | DE1084861B (en) |
| ES (1) | ES247118A1 (en) |
| FR (1) | FR1216168A (en) |
| GB (1) | GB849998A (en) |
| MY (1) | MY6200086A (en) |
| NL (2) | NL120003C (en) |
| OA (1) | OA00553A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3408287A (en) * | 1966-04-20 | 1968-10-29 | Universal Oil Prod Co | Oxidation of mercaptans |
| DE1290279B (en) * | 1961-11-24 | 1969-03-06 | Universal Oil Prod Co | Process for obtaining a hydrocarbon distillate with reduced mercaptan content and improved color |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2966452A (en) * | 1959-02-24 | 1960-12-27 | Universal Oil Prod Co | Sweetening sour hydrocarbon distillate with metal phthalocyanine catalyst in the presence of alkali air and sulfite ions |
| US2999806A (en) * | 1959-03-13 | 1961-09-12 | Universal Oil Prod Co | Treatment of hydrocarbon distillates |
| US2988500A (en) * | 1959-03-13 | 1961-06-13 | Universal Oil Prod Co | Treatment of hydrocarbon distillates |
| US2976229A (en) * | 1959-04-24 | 1961-03-21 | Universal Oil Prod Co | Purification of acid oils |
| US3108081A (en) * | 1959-07-17 | 1963-10-22 | Universal Oil Prod Co | Catalyst and manufacture thereof |
| NL258849A (en) * | 1959-12-10 | |||
| NL259485A (en) * | 1959-12-28 | |||
| US3029202A (en) * | 1960-04-19 | 1962-04-10 | Universal Oil Prod Co | Treating waste water |
| NL275000A (en) * | 1961-03-14 | 1900-01-01 | ||
| DE1254274B (en) * | 1961-06-13 | 1967-11-16 | Universal Oil Prod Co | Process for the oxidation of mercaptans in an acidic hydrocarbon distillate |
| US3252891A (en) * | 1964-08-28 | 1966-05-24 | Universal Oil Prod Co | Oxidation of mercaptans |
| US3252890A (en) * | 1964-08-28 | 1966-05-24 | Universal Oil Prod Co | Oxidation of mercaptans using phthalocyanine and mercury catalyst |
| US3260665A (en) * | 1964-10-23 | 1966-07-12 | Universal Oil Prod Co | Oxidation of difficultly oxidizable mercaptans |
| US3410727A (en) * | 1965-01-08 | 1968-11-12 | Allis Chalmers Mfg Co | Fuel cell electrodes having a metal phthalocyanine catalyst |
| US3493596A (en) * | 1966-03-23 | 1970-02-03 | Universal Oil Prod Co | Synthesis of organic isocyanates |
| US3413215A (en) * | 1966-05-16 | 1968-11-26 | Universal Oil Prod Co | Oxidation of mercapto compounds |
| US3525683A (en) * | 1968-03-21 | 1970-08-25 | Phillips Petroleum Co | Sweetening of jp-4 jet fuel with an alkali metal plumbite,phthalocyanine compound and elemental sulfur |
| US4003827A (en) * | 1975-06-12 | 1977-01-18 | Universal Oil Products Company | Mercaptan conversion process for a petroleum distillate charge stock |
| US4070271A (en) * | 1975-09-22 | 1978-01-24 | Uop Inc. | Catalytic oxidation of mercaptans and removal of naphthenic acids, catalyst toxins, and toxin precursors from petroleum distillates |
| US4088569A (en) * | 1976-02-24 | 1978-05-09 | Uop Inc. | Mercaptan oxidation in a liquid hydrocarbon with a metal phthalocyanine catalyst |
| US4141819A (en) * | 1977-01-18 | 1979-02-27 | Uop Inc. | Process for treating a sour petroleum distillate |
| US4087378A (en) * | 1977-01-18 | 1978-05-02 | Uop Inc. | Preparation of a supported metal phthalocyanine |
| US4412913A (en) * | 1982-08-05 | 1983-11-01 | Standard Oil Company (Indiana) | Use of alkanolamines in sweetening sour liquid hydrocarbon streams |
| US4412912A (en) * | 1983-03-01 | 1983-11-01 | Uop Inc. | Hydrocarbon treating process having minimum gaseous effluent |
| US4481106A (en) * | 1983-12-05 | 1984-11-06 | Uop Inc. | Hydrocarbon treating process |
| US4906354A (en) * | 1987-09-10 | 1990-03-06 | Mobil Oil Corporation | Process for improving the thermal stability of jet fuels sweetened by oxidation |
| US4875997A (en) * | 1988-11-17 | 1989-10-24 | Montana Refining Company | Process for treating hydrocarbons containing mercaptans |
| CA2120046C (en) * | 1994-01-27 | 1999-09-14 | M-I L.L.C. | Separately removing mercaptans and hydrogen sulfide from gas streams |
| US5683574A (en) * | 1994-08-08 | 1997-11-04 | Chevron U.S.A. Inc. | Method for the extraction of low molecular weight mercaptans from petroleum and gas condensates |
| US7014751B2 (en) * | 2001-06-19 | 2006-03-21 | Exxonmobil Research And Engineering Co. | Continuous liquid hydrocarbon treatment method |
| CN101568600B (en) | 2006-12-22 | 2013-01-30 | 陶氏环球技术公司 | Tetrasulfoiron phthalocyanine and related methods |
| WO2016029387A1 (en) | 2014-08-27 | 2016-03-03 | 中国石油天然气集团公司 | Bimetallic mercaptan transfer catalyst used in low-temperature mercaptan removal of liquefied petroleum gas |
| CN105085338B (en) * | 2015-08-25 | 2017-09-05 | 成都德美工程技术有限公司 | The production method and device of DMDS |
| CN117143106A (en) * | 2023-08-31 | 2023-12-01 | 中国日用化学研究院有限公司 | A method for synthesizing cobalt phthalocyanine sulfonic acid by SO3 sulfonation method |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1998863A (en) * | 1932-05-10 | 1935-04-23 | Phillips Petroleum Co | Process for desulphurizing mercaptan-bearing oil |
| US2550091A (en) * | 1948-08-11 | 1951-04-24 | Standard Oil Co | Mercaptan removal from hydrocarbons |
| US2659691A (en) * | 1949-08-26 | 1953-11-17 | Raffinage Cie Francaise | Process for refining petroleum products |
| US2651595A (en) * | 1950-05-20 | 1953-09-08 | Socony Vacuum Oil Co Inc | Treating hydrocarbons |
-
0
- NL NL235884D patent/NL235884A/xx unknown
- NL NL120003D patent/NL120003C/xx active
- BE BE575509D patent/BE575509A/xx unknown
-
1958
- 1958-02-13 US US714937A patent/US2882224A/en not_active Expired - Lifetime
-
1959
- 1959-02-06 DE DEU5960A patent/DE1084861B/en active Pending
- 1959-02-09 ES ES0247118A patent/ES247118A1/en not_active Expired
- 1959-02-09 GB GB4396/59A patent/GB849998A/en not_active Expired
- 1959-02-10 FR FR786323A patent/FR1216168A/en not_active Expired
-
1962
- 1962-12-31 MY MY196286A patent/MY6200086A/en unknown
-
1964
- 1964-11-18 OA OA50640A patent/OA00553A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1290279B (en) * | 1961-11-24 | 1969-03-06 | Universal Oil Prod Co | Process for obtaining a hydrocarbon distillate with reduced mercaptan content and improved color |
| US3408287A (en) * | 1966-04-20 | 1968-10-29 | Universal Oil Prod Co | Oxidation of mercaptans |
Also Published As
| Publication number | Publication date |
|---|---|
| BE575509A (en) | |
| OA00553A (en) | 1966-07-15 |
| NL120003C (en) | |
| US2882224A (en) | 1959-04-14 |
| ES247118A1 (en) | 1959-06-01 |
| NL235884A (en) | |
| DE1084861B (en) | 1960-07-07 |
| FR1216168A (en) | 1960-04-22 |
| MY6200086A (en) | 1962-12-31 |
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