US2286475A - Treatment of hydrocarbons - Google Patents
Treatment of hydrocarbons Download PDFInfo
- Publication number
- US2286475A US2286475A US365230A US36523040A US2286475A US 2286475 A US2286475 A US 2286475A US 365230 A US365230 A US 365230A US 36523040 A US36523040 A US 36523040A US 2286475 A US2286475 A US 2286475A
- Authority
- US
- United States
- Prior art keywords
- compounds
- gasoline
- ethyl
- aminophenol
- hydroxy
- 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 - Lifetime
Links
- 229930195733 hydrocarbon Natural products 0.000 title description 2
- 150000002430 hydrocarbons Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- -1 octyl p-aminophenol Chemical compound 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- XKZGIJICHCVXFV-UHFFFAOYSA-N 2-ethylhexyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCC(CC)CCCC)OC1=CC=CC=C1 XKZGIJICHCVXFV-UHFFFAOYSA-N 0.000 description 1
- XPHCXUQZUCONRA-UHFFFAOYSA-N 4-amino-2-butylphenol Chemical compound CCCCC1=CC(N)=CC=C1O XPHCXUQZUCONRA-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/223—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom
- C10L1/2235—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond having at least one amino group bound to an aromatic carbon atom hydroxy containing
Definitions
- the inhibitor art is known to include the use of such compounds as phenols, amines, and aminophenols and crude primary Q products containing these compounds, and no basic claim is made therein to the broad use of any of theseclasses.
- the present invention is specially concerned. with alimited group of compounds which have n found to possess good inhibiting potency combined with resistance to accidental removal by contact with water or caustic soda which occurs at many points in the storage systems of oil refineries.
- the present invention comprises the treatment of unstable gasolines particularly cracked gasolines to materially arrest the deterioration thereof byadding to said ,gasolin'es relatively small percentages of disubstituted aminophenols, in which one of the amino hydrogen atoms has been replaced by an alkyl group and the other being a hydroxy alkyl group.
- a method for stab" gasoline against deterioration thereof'on storage which comprises.
- the effective inhibitor ratio used in the table indicates the relative value of the compounds based on the induction periods and referredto We claim as our -invention: y
- a method for stabilizing gasoline against deterioration thereof on storage which comprises adding to the gasoline a relatively small amount of an N-substituted aminophenol-in which one of the amino hydrogen atoms has been replaced hydrogen atoms has been replaced by an ethyl group and the other by a hydroxy alkyl group.
- a method for stabilizing gasoline against deterioration thereof on storage which comprises of N-n-butyl N-beta hydroxy ethyl p-amino-. phenol.
- Motor fuel com prising gasoline normally tending to deteriorate'on storage'and containing a relatively small amount of a N-substituted a relativelysmall amount of an ami'nophenol in which one of the amino hydrogen atoms has been replaced by an ethyl groupand the other by a hydroxy alkyl group.
- Motor fuel comprising gasoline normally tending to deteriorateon'storage and containing a relatively small amount of N-n-butyl-N-betahydroxy ethyl p-aminophenol.
- Motor fuel comprising gasoline normally tending to deteriorate on storage and containing a relatively small amountof N-n-octyl-N- beta-hydroxy ethyl p-aminophenol.
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)
Description
Patented June 16, I942 siren STATE s1 PATENT OFFICE. v
TREATMENT OF HYDROCARBONS' Gustav Eglofi and Charles G. Dryer, Chicago, 111.,
assignors to Universal Oil Products Company, Chicago, 111., a corporation of Delaware No Drawing. Original Serial No. 216,068.
application June 21, 1938, Divided and this application November 12, 1940, Serial No. 365,230
. 8 Claims.
carbon distillates containing appreciable quantities of oleflnic and other unsaturated hydrocarbons are subject. The art of using inhibitors in unstable cracked gasolines is now one of comparatively long standing and a large number of individual compounds'and classes of compounds have been developed for practical use, all of which apparently possess the characteristic of being more or less readily oxidizable so that the peroxidic compounds which are primarily formed when ole-containing gasoiines are in contact with air or other oxidizing gas mixtures are decomposed and the sequence of the chain reactions leading tothe formation of higher boiling polymers and resinous products which cause the de-' terioration .of the gasoline in respect to color, gum content, and antiknock value is stopped for a time depending upon the 'e' fliciency or the in-v hibitor, the degree of unsaturation of the oil and the extent of its exposure.
It isrecognized that the inhibitor art is known to include the use of such compounds as phenols, amines, and aminophenols and crude primary Q products containing these compounds, and no basic claim is made therein to the broad use of any of theseclasses. The present invention is specially concerned. with alimited group of compounds which have n found to possess good inhibiting potency combined with resistance to accidental removal by contact with water or caustic soda which occurs at many points in the storage systems of oil refineries.
In one specific embodiment the present invention comprises the treatment of unstable gasolines particularly cracked gasolines to materially arrest the deterioration thereof byadding to said ,gasolin'es relatively small percentages of disubstituted aminophenols, in which one of the amino hydrogen atoms has been replaced by an alkyl group and the other being a hydroxy alkyl group.
Compounds of the above type, inaddition to specially with the having high inhibiting emciency, have been found to have considerable resistance to removal by accidental' water or aqueous alkali contacts which gasolines containing them encounter under normalrconditions of service in oil refineries; Typical data showing the results obtained in practice with these compounds-will be given in a later section.
The following example is given to illustrate the general methods of preparing compounds of the present character: I
i N-n-butylvN-b-hydrozy ethyl p aminophenol The tabulation given below shows the mixture of compounds which were reacted to form the desired compound:
, Parts by b-Hydroxy-ethyl p-aminophenol n-Butyl bromide"; 27.4 Sodium bicarbonate 16.8 Ethyl alcohol r 200.0
The above mixture of compounds was refluxed for about 12 hours and the contents were then poured into an excess of water after which the water-oil mixture was extracted with ether. The combined ether extracts were heated weight 30.6
to distill oil the ether and then subjected to further distillation at a pressure of 4 mm. absolute. A yield of 28.1 parts by weight of the desired com pound boiling at 183186 C. under the reduced pressure was obtained which amounted to 81% of the theoretical yield. A redistiila'tion of this material showed a boiling range of 182-483 C. at the same reduced pressure. The principal restructural equation:
b-Hydroxy-ethyl N-n-butyl-N-b-h am p-sminophenol other p-amlnop The present "class of compounds is suflici'en potent so that only minorquantities are neces- The following table is introduced to shdw thev character of the results obtainable in practice by the use of the present type of inhibitors although 55 not with the intent oi unduly limiting the invenot the yessel action taking place is given by the following a standard inhibitor.
adding to the gasoline a relatively small amount tions proper scope. In all cases 0.01% of the 4. A method for stab" gasoline against deterioration thereof'on storage which comprises.
inhibitor by weight of the gasoline was used.
the higher molecular weight mixed substituted compounds there is a very low percentage removal by water washing although they are considerably affected by the action of'caustic soda.
The effective inhibitor ratio used in the table indicates the relative value of the compounds based on the induction periods and referredto We claim as our -invention: y
1. A method for stabilizing gasoline against deterioration thereof on storage which comprises adding to the gasoline a relatively small amount of an N-substituted aminophenol-in which one of the amino hydrogen atoms has been replaced hydrogen atoms has been replaced by an ethyl group and the other by a hydroxy alkyl group. 3. A method for stabilizing gasoline against deterioration thereof on storage which comprises of N-n-butyl N-beta hydroxy ethyl p-amino-. phenol.
gasoline against Y MgJlOO cc. copper dish Oxygen bomb stab. ind. Percent removed Emotive period, min. y-
inhibitor ratio- Water Caustic Orig Water Caustic Water Caustic washed washed a washed washed wash wash on alga-saline 37 218 100 st s5 N- -hydroxy-ethyl-N.-
butylp-aminophenol 1.38 3 7 13 295 170 110 6o 84 N b-hydroxy ethyl N octyl p-aminophenol 1.38 4 5 81 350 .235 43 1 9i The above data shows that particularly with 15 adding to the gasoline a relatively small amount of N-n-octyl-N-beta-hydroxy ethyl p-aminophenol.
5. Motor fuel com prising gasoline normally tending to deteriorate'on storage'and containing a relatively small amount of a N-substituted a relativelysmall amount of an ami'nophenol in which one of the amino hydrogen atoms has been replaced by an ethyl groupand the other by a hydroxy alkyl group. v
7. Motor fuel comprising gasoline normally tending to deteriorateon'storage and containing a relatively small amount of N-n-butyl-N-betahydroxy ethyl p-aminophenol. A
8. Motor fuel comprising gasoline normally tending to deteriorate on storage and containing a relatively small amountof N-n-octyl-N- beta-hydroxy ethyl p-aminophenol.
GUSTAV new. cnmrns a, Dayna.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US365230A US2286475A (en) | 1938-06-27 | 1940-11-12 | Treatment of hydrocarbons |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US21606838A | 1938-06-27 | 1938-06-27 | |
| US365230A US2286475A (en) | 1938-06-27 | 1940-11-12 | Treatment of hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2286475A true US2286475A (en) | 1942-06-16 |
Family
ID=26910619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US365230A Expired - Lifetime US2286475A (en) | 1938-06-27 | 1940-11-12 | Treatment of hydrocarbons |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2286475A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5908961A (en) * | 1996-09-19 | 1999-06-01 | Ciba Specialty Chemicals Corporation | Production of aminophenols |
-
1940
- 1940-11-12 US US365230A patent/US2286475A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5908961A (en) * | 1996-09-19 | 1999-06-01 | Ciba Specialty Chemicals Corporation | Production of aminophenols |
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