US2110274A - Light stabilizer for hydrocarbons - Google Patents
Light stabilizer for hydrocarbons Download PDFInfo
- Publication number
- US2110274A US2110274A US23452A US2345235A US2110274A US 2110274 A US2110274 A US 2110274A US 23452 A US23452 A US 23452A US 2345235 A US2345235 A US 2345235A US 2110274 A US2110274 A US 2110274A
- Authority
- US
- United States
- Prior art keywords
- aliphatic
- esters
- value
- hydrocarbons
- light stabilizer
- 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 6
- 150000002430 hydrocarbons Chemical class 0.000 title description 5
- 239000004611 light stabiliser Substances 0.000 title 1
- 239000000446 fuel Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- -1 aromatic alcohol amine esters Chemical class 0.000 description 6
- 239000003502 gasoline Substances 0.000 description 6
- 230000000087 stabilizing effect Effects 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C10L1/2222—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates
- C10L1/2225—(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates hydroxy containing
-
- 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
- This invention relates to the improvement of come these difliculties by adding to the fuels, small but efiective quantities of oil soluble aliphatic or aromatic alcohol amine esters, or ethers.
- esters may be obtained by the action of the corresponding acids, acid chlorides, acid an-v hydrides or other compounds which give esters or' ethers, by reacting with aliphatic or aromatic hydroxyamines as, for example, according to the following equation:
- the products formed according to this reaction are generally recovered as the salts of the acid employed in the esterification. These salts may be neutralized with weak bases, if it be so desired, in order to produce the free amines for use according to this invention. However the salts J themselves may be-employed for the same purpose,
- the hydrocarbon radicals R and Rf may be either normal or branched. I Although any aliphatic hydroxy compound may be employed as a raw material, it is preferred to use the water-soluble amines, suchas the ethanol amines, propanol amines and the like, because of their effectiveness in stabilizing fuels.
- the materials suitable for the purposes of the present invention are: triacetoxy-- triethanolamine (CHsCOOCHzCHahN, triacetoxy-triethanolamine laurate, tripropionyl-tripropanolamine .0 amine phenolate, acetlyated triethanolamine salts benzoate, dibenzoyl triethanolof hydroxylstearic acid or of tertiary butyl phenol.
- Tributyryl, divalyryl, mono-oleyl and distearyl and similar esters of triethanolamine and similar compounds may also be used.
- These compounds may be added to the fuels in proportions of 0.01% to 0.5% depending on the stability of the fuel and the effectiveness of the inhibitor.
- the alcoholamine esters herein described may be employed to stabilize gasolines, naphthas, kerosenes and similar products with boiling ranges up to 650 F.
- gasoline rich in cracked products benzol or other cyclic materials, such as the fuels prepared by' vapor phase or liquid phase crack ing of petroleum oils or coal tar oils, are satisfactorily stabilized according to this invention.
- Blended fuels as, for example, gasoline containing alcohols, metallo-organic anti-knock compounds, dyes, lubricating agents, soaps, thickeners and the like may also be treated in the same 8011.000H+(HOOH,CH,);N (OH
- a hydrocarbon fuel which has been stabilized against deterioration by the action of light by adding thereto approximately 0.01 to 0.5% of a.
- esters having the general formula gacooaomm having the general formula gacooaomm
- R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydpcarbon radical while a: is any value from 0 to 2 and n is any value from 1 to 3.
- a hydrocarbon fuel which has been stabilized against deterioration/bythe action of light by '(RCOOR')nNH.-c and in which R is-an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical, while a: is any value from 0 to 2 and n is any value from 1 to 3.
- a hydrocarbon fuel which has been stabilized against deterioration by the action ofllght by adding thereto approximately 0.01 to 0.5% of a substance selected from the group consisting of esters having the general formula (RcooRomra,
- R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical, while a: is any value from 0 to 2, and n is any value from 1 to 3.
Description
Patented Mar. 8, 19 38 2,110,274 LIGHT STABILIZER- FOR HYDROCABBONS I 7 Louis A. Mikeska, Elizabeth, and John B. Holtzclaw, Roselle, N. J., assignor's to Standard'0il Development Company, a corporation ware of Dela- No Drawing. Application May 25, 1935,
SerialNo. 23,452
10 Claims.
This invention relates to the improvement of come these difliculties by adding to the fuels, small but efiective quantities of oil soluble aliphatic or aromatic alcohol amine esters, or ethers.
These esters may be obtained by the action of the corresponding acids, acid chlorides, acid an-v hydrides or other compounds which give esters or' ethers, by reacting with aliphatic or aromatic hydroxyamines as, for example, according to the following equation:
value from 1 toil.-
' The products formed according to this reaction are generally recovered as the salts of the acid employed in the esterification. These salts may be neutralized with weak bases, if it be so desired, in order to produce the free amines for use according to this invention. However the salts J themselves may be-employed for the same purpose,
and it is our intention toemploy such salts or even salts containing different acid groups than those where R and R are aliphatic or cyclic radicals, while a: is any value from 0 to 2, and n is any' present in the ester radicals, as exemplified by the formula (ROOR') nNHxHR" where HR may 0' be an aliphatic or cyclic carboxylic acid or phenol.
The hydrocarbon radicals R and Rf may be either normal or branched. I Although any aliphatic hydroxy compound may be employed as a raw material, it is preferred to use the water-soluble amines, suchas the ethanol amines, propanol amines and the like, because of their effectiveness in stabilizing fuels.
In the case of the polyhydroxy alkyl amines, it is possible to esterify sufilcient hydroxy groups to make the products oil-soluble, thereby often leaving some free hydroxy groups in the molecule, although it is preferable to esterify all the hydroxy groupsso as to produce a more stable compoimd. Examples of the materials suitable for the purposes of the present invention are: triacetoxy-- triethanolamine (CHsCOOCHzCHahN, triacetoxy-triethanolamine laurate, tripropionyl-tripropanolamine .0 amine phenolate, acetlyated triethanolamine salts benzoate, dibenzoyl triethanolof hydroxylstearic acid or of tertiary butyl phenol. Tributyryl, divalyryl, mono-oleyl and distearyl and similar esters of triethanolamine and similar compounds may also be used.
These compounds may be added to the fuels in proportions of 0.01% to 0.5% depending on the stability of the fuel and the effectiveness of the inhibitor.
In the case of triacetoxy-triethanolamine in a freshly prepared cracked U. S. grade motor gasoline, the quantity of inhibitor employed to give satisfactory results was in the neighborhood of 0.05%.
The alcoholamine esters herein described may be employed to stabilize gasolines, naphthas, kerosenes and similar products with boiling ranges up to 650 F.
For instance, gasoline rich in cracked products, benzol or other cyclic materials, such as the fuels prepared by' vapor phase or liquid phase crack ing of petroleum oils or coal tar oils, are satisfactorily stabilized according to this invention.
Blended fuels as, for example, gasoline containing alcohols, metallo-organic anti-knock compounds, dyes, lubricating agents, soaps, thickeners and the like may also be treated in the same 8011.000H+(HOOH,CH,);N (OH|O0.0OHIOHmN+aHIO trlaootoxytriothanolamino mm Y A cracked gasoline was blended with varying quantities of triacetoxytriethanolamine and ex-.
posed to the sunlight in 4 oz. sample bottles together with a blank sample of the same gasoline. The following results were obtained after the exposed sample stood for six months:
I Sample I Color Residue 283" Odor Sweet. I
Sweet- Cloudy,
Clean...
Clean.--
Consider- Slight-..
s s b Dark reddish brown. Wat! white.
Water white.
Original gasoline.-- Bcm e+0.1% inhibr. Bambi- .2% inhlbitor.
These tests show the exceptional stabilizing prop.-
erties of the inhibitors prepared according to the invention.
It will be understood that the invention is not limited to the description given above nor to the examples cited, and other acids and other hydroxya'mines may be used to prepare other esters and other compounds of the same general type as those shown in the equation which has been given.
The invention is not to be limited to any theoretical statements which have been presented herein solely for purposes of illustration, but is limited only by the following claims in which it is intended to claim all novelty insofar as prior art permits.
We claim:
1. The process of stabilizing a hydrocarbon liquid which comprises adding thereto approximately 0.01 to 0.5% of a substance selected from the group consisting of esters having the general for- 'mula (RCOOR )7lNHI, in which R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical while a: is any value from to 2 and n is any value from 1 to 3.
2. The process of stabilizing motor fuels which comprises adding thereto approximately 0.01 to 0.5% of triacetoxytriethanolamine.
3. The process of stabilizing motor fuels which comprises addingthereto approximately0.01 to 0.5% of tripropionyltrihydroxy-trialkylamines.
' 4. The process of stabilizing motor fuels which comprises adding thereto approximately. 0.01 to 0.5% of tributyryltriethanolamine.
5. A hydrocarbon fuel which has been stabilized against deterioration by the action of light by adding thereto approximately 0.01 to 0.5% of a.
substance selected from the group consisting of esters having the general formula gacooaomm,
in which R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydpcarbon radical while a: is any value from 0 to 2 and n is any value from 1 to 3.
6. A hydrocarbon fuel which has been stabilized against deterioration/bythe action of light by '(RCOOR')nNH.-c and in which R is-an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical, while a: is any value from 0 to 2 and n is any value from 1 to 3.
10. A hydrocarbon fuel which has been stabilized against deterioration by the action ofllght by adding thereto approximately 0.01 to 0.5% of a substance selected from the group consisting of esters having the general formula (RcooRomra,
and in which R is an aliphatic or aromatic hydrocarbon radical and R is an aliphatic hydrocarbon radical, while a: is any value from 0 to 2, and n is any value from 1 to 3.
LOUIS A. MIKESKA. JOHN B. HOLTZCLAW.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23452A US2110274A (en) | 1935-05-25 | 1935-05-25 | Light stabilizer for hydrocarbons |
| FR797011D FR797011A (en) | 1935-05-25 | 1935-10-28 | Process for stabilizing hydrocarbons in the light |
| DEST54551D DE711451C (en) | 1935-05-25 | 1936-02-27 | Process for stabilizing fuels |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23452A US2110274A (en) | 1935-05-25 | 1935-05-25 | Light stabilizer for hydrocarbons |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2110274A true US2110274A (en) | 1938-03-08 |
Family
ID=21815197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US23452A Expired - Lifetime US2110274A (en) | 1935-05-25 | 1935-05-25 | Light stabilizer for hydrocarbons |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2110274A (en) |
| DE (1) | DE711451C (en) |
| FR (1) | FR797011A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2506492A (en) * | 1946-07-27 | 1950-05-02 | Raymond Lab Inc | Stabilized sulfite solutions |
| US3091521A (en) * | 1960-05-03 | 1963-05-28 | Standard Oil Co | Gasoline composition |
| US5964907A (en) * | 1996-08-14 | 1999-10-12 | Akzo Nobel N.V. | Fuel compositions containing esteramines |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3088815A (en) * | 1958-03-27 | 1963-05-07 | Sinclair Research Inc | Fuel oil |
| FR2576032B1 (en) * | 1985-01-17 | 1987-02-06 | Elf France | HOMOGENEOUS AND STABLE COMPOSITION OF ASPHALTENIC LIQUID HYDROCARBONS AND AT LEAST ONE ADDITIVE USABLE IN PARTICULAR AS FUEL INDUSTRIAL |
-
1935
- 1935-05-25 US US23452A patent/US2110274A/en not_active Expired - Lifetime
- 1935-10-28 FR FR797011D patent/FR797011A/en not_active Expired
-
1936
- 1936-02-27 DE DEST54551D patent/DE711451C/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2506492A (en) * | 1946-07-27 | 1950-05-02 | Raymond Lab Inc | Stabilized sulfite solutions |
| US3091521A (en) * | 1960-05-03 | 1963-05-28 | Standard Oil Co | Gasoline composition |
| US5964907A (en) * | 1996-08-14 | 1999-10-12 | Akzo Nobel N.V. | Fuel compositions containing esteramines |
| US6013115A (en) * | 1996-08-14 | 2000-01-11 | Akzo N.V. | Fuel additive compositions for simultaneously reducing intake valve and combustion chamber deposits |
Also Published As
| Publication number | Publication date |
|---|---|
| DE711451C (en) | 1941-10-01 |
| FR797011A (en) | 1936-04-20 |
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