DE1470683C3 - Verfahren zum Entmercaptanisieren von sauren Kohlenwasserstoffdestillaten mit einem Inhibitorsüßungsmittel vom Phenylentiamintyp - Google Patents
Verfahren zum Entmercaptanisieren von sauren Kohlenwasserstoffdestillaten mit einem Inhibitorsüßungsmittel vom PhenylentiamintypInfo
- Publication number
- DE1470683C3 DE1470683C3 DE1470683A DE1470683A DE1470683C3 DE 1470683 C3 DE1470683 C3 DE 1470683C3 DE 1470683 A DE1470683 A DE 1470683A DE 1470683 A DE1470683 A DE 1470683A DE 1470683 C3 DE1470683 C3 DE 1470683C3
- Authority
- DE
- Germany
- Prior art keywords
- phenylenediamine
- percent
- weight
- gasoline
- inhibitor
- 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
- 239000003112 inhibitor Substances 0.000 title claims description 29
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 18
- 229930195733 hydrocarbon Natural products 0.000 title claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 18
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title claims description 14
- 230000002378 acidificating effect Effects 0.000 title claims description 14
- 235000003599 food sweetener Nutrition 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 239000003765 sweetening agent Substances 0.000 title claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003502 gasoline Substances 0.000 description 40
- 238000012360 testing method Methods 0.000 description 23
- 239000000203 mixture Substances 0.000 description 18
- 239000000523 sample Substances 0.000 description 18
- FTBVOJZWVWWLFB-UHFFFAOYSA-N 2-(octan-2-ylamino)ethanol Chemical compound CCCCCCC(C)NCCO FTBVOJZWVWWLFB-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000011593 sulfur Substances 0.000 description 9
- JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 230000006698 induction Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PZOIEPPCQPZUAP-UHFFFAOYSA-N 1-aminohexan-2-ol Chemical compound CCCCC(O)CN PZOIEPPCQPZUAP-UHFFFAOYSA-N 0.000 description 1
- PWNBRRGFUVBTQG-UHFFFAOYSA-N 1-n,4-n-di(propan-2-yl)benzene-1,4-diamine Chemical compound CC(C)NC1=CC=C(NC(C)C)C=C1 PWNBRRGFUVBTQG-UHFFFAOYSA-N 0.000 description 1
- FBBCNGBQXAYBEA-UHFFFAOYSA-N 1-n,4-n-dipropylbenzene-1,4-diamine Chemical compound CCCNC1=CC=C(NCCC)C=C1 FBBCNGBQXAYBEA-UHFFFAOYSA-N 0.000 description 1
- KTQKUEHWHZBKAC-UHFFFAOYSA-N 2-(5-methylheptan-3-ylamino)ethanol Chemical compound CCC(C)CC(CC)NCCO KTQKUEHWHZBKAC-UHFFFAOYSA-N 0.000 description 1
- SFGIGHHJJKSNMF-UHFFFAOYSA-N 2-(decan-2-ylamino)ethanol Chemical compound CCCCCCCCC(C)NCCO SFGIGHHJJKSNMF-UHFFFAOYSA-N 0.000 description 1
- SRVPCSAOCZQYFX-UHFFFAOYSA-N 2-(dodecan-2-ylamino)ethanol Chemical compound CCCCCCCCCCC(C)NCCO SRVPCSAOCZQYFX-UHFFFAOYSA-N 0.000 description 1
- NHIIFTZFLLWIDQ-UHFFFAOYSA-N 2-(hexan-2-ylamino)ethanol Chemical compound CCCCC(C)NCCO NHIIFTZFLLWIDQ-UHFFFAOYSA-N 0.000 description 1
- HQYIRIFFZWXTMV-UHFFFAOYSA-N 2-(nonan-2-ylamino)ethanol Chemical compound CCCCCCCC(C)NCCO HQYIRIFFZWXTMV-UHFFFAOYSA-N 0.000 description 1
- CDYVWGIMCGTYEA-UHFFFAOYSA-N 2-(undecan-2-ylamino)ethanol Chemical compound CCCCCCCCCC(C)NCCO CDYVWGIMCGTYEA-UHFFFAOYSA-N 0.000 description 1
- PKGKENZMQLXYCF-UHFFFAOYSA-N 2-aminoheptan-1-ol Chemical compound CCCCCC(N)CO PKGKENZMQLXYCF-UHFFFAOYSA-N 0.000 description 1
- CTDFCRIOSLTKFQ-UHFFFAOYSA-N 5-aminooctan-4-ol Chemical compound CCCC(N)C(O)CCC CTDFCRIOSLTKFQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- GPQWKLDEDGOJQH-UHFFFAOYSA-N ethane-1,1,1,2-tetramine Chemical compound NCC(N)(N)N GPQWKLDEDGOJQH-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- -1 phenylenediamine compound Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000004448 titration Methods 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
- 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US193312A US3114700A (en) | 1962-05-08 | 1962-05-08 | Sweetening of sour hydrocarbon distillates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1470683A1 DE1470683A1 (de) | 1968-12-05 |
| DE1470683B2 DE1470683B2 (de) | 1973-03-08 |
| DE1470683C3 true DE1470683C3 (de) | 1973-10-04 |
Family
ID=22713108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1470683A Expired DE1470683C3 (de) | 1962-05-08 | 1963-05-06 | Verfahren zum Entmercaptanisieren von sauren Kohlenwasserstoffdestillaten mit einem Inhibitorsüßungsmittel vom Phenylentiamintyp |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3114700A (en:Method) |
| DE (1) | DE1470683C3 (en:Method) |
| FI (1) | FI44826C (en:Method) |
| GB (1) | GB1035163A (en:Method) |
| NL (2) | NL142985B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2550421C2 (de) * | 1975-11-10 | 1984-06-28 | Monsanto Co., St. Louis, Mo. | N-Isopropyl-N'-5-methyl-3-heptyl-p-phenylendiamin und N-1,3-Dimethylbutyl-N'-1,4-dimethylpentyl-p-phenylendiamin und ihre Verwendung als Stabilisatoren für Kautschuk |
| GB1561362A (en) * | 1976-04-20 | 1980-02-20 | Ferrosan Ab | Aminoalcohols and oral compositions thereof |
| BRPI0613421A2 (pt) * | 2005-07-21 | 2011-05-31 | Taminco | combustìvel tratado, e, método para tratar um combustìvel |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2978404A (en) * | 1959-06-18 | 1961-04-04 | Sun Oil Co | Oxidative sweetening with alkaline material and partial ester of polyhydric alcohol |
-
0
- NL NL292413D patent/NL292413A/xx unknown
-
1962
- 1962-05-08 US US193312A patent/US3114700A/en not_active Expired - Lifetime
-
1963
- 1963-05-02 GB GB17326/65A patent/GB1035163A/en not_active Expired
- 1963-05-06 DE DE1470683A patent/DE1470683C3/de not_active Expired
- 1963-05-07 NL NL63292413A patent/NL142985B/xx unknown
- 1963-05-07 FI FI630934A patent/FI44826C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| NL142985B (nl) | 1974-08-15 |
| GB1035163A (en) | 1966-07-06 |
| US3114700A (en) | 1963-12-17 |
| DE1470683B2 (de) | 1973-03-08 |
| FI44826C (fi) | 1972-01-10 |
| NL292413A (en:Method) | |
| FI44826B (en:Method) | 1971-09-30 |
| DE1470683A1 (de) | 1968-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EHJ | Ceased/non-payment of the annual fee |