US2469737A - Addition agent for gasoline - Google Patents
Addition agent for gasoline Download PDFInfo
- Publication number
- US2469737A US2469737A US716432A US71643246A US2469737A US 2469737 A US2469737 A US 2469737A US 716432 A US716432 A US 716432A US 71643246 A US71643246 A US 71643246A US 2469737 A US2469737 A US 2469737A
- Authority
- US
- United States
- Prior art keywords
- gasoline
- lead
- tetraethyl
- fuel
- acid
- 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
- 239000003795 chemical substances by application Substances 0.000 title description 2
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 29
- 239000000446 fuel Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- VPTNWGPGDXUKCY-KHPPLWFESA-N (z)-4-decoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCCCCCOC(=O)\C=C/C(O)=O VPTNWGPGDXUKCY-KHPPLWFESA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 210000003056 antler Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VLZZXGOEDAYHOI-UHFFFAOYSA-N ethyllead Chemical compound CC[Pb] VLZZXGOEDAYHOI-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- -1 fumaric acid ester Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C10L1/103—Liquid carbonaceous fuels containing additives stabilisation of anti-knock agents
Definitions
- Patented may 10,- 1949 2,469,737 nnm'rrou AGENT Foa GASOLINE .1 11930. Ml Nab, Cranford, and Barry W. Budd.
- This invention relates to motor-fuels?antler e lates more particularly to the stabilization-of tetraethyl lead in motor fuels.
- Polymerized alpha-beta unsaturated esters which may be employed in accordance with our invention to stabilize lead tetraethyl include polymerized esters of acrylic acid, methacrylic acid, fumaric acid, maleic acid, itaconic acid and mesaconic acid and polymerized vinyl esters of fatty acids. These polymers should have a molecular weight of 2,000 to 30,000 or even higher and should be soluble in motor fuel.
- the amount of stabilizer used depends on theamount of tetraethyl lead in the gasoline. It has been found that ordinarily 0.1 to 1% by weight of the above stabilizers based on the total weight of gasoline is sufficient for most purposes.
- the stabilizers may be added to the gasoline directly or, if necessary, dissolved in a suitable solvent and then added to the gasoline in desired proportions.
- the stabilizers may also be added to motor fuel adjuncts such as benzene or alcohol, antioxidants, solvent oils, deactivators etc., or with metal salts of acidic cyanic compounds etc.
- stabilizers may be added directly to the ethyl fluid with additional amounts of solvent, if necessary, and sold and shipped in this form. In this way the addition of tetraethyl lead to gasoline and addition of stabilizer occur simulta.
- a composition consisting essentially of tetraethyl lead and a small but stabilizing amount mixture of decyl maleate and ethyl lead and a small but stabilizing amountof a polymerized fumaric acid ester having a molecular weight of at least 2,000 to 30,000.
- a composition consisting essentially of gasoline, suflicient tetraethyl lead to increase the antiknock properties'oi' the fuel and 0.01-1.0 weight per cent based on the gasoline of polymerized ester of an alpha-beta unsaturated acid having a mo; lecular weight of at least 2,000 to 30,000.
- a composition consisting essentially of gasoline, sufilcient tetraethyl lead to increase the antiknock properties of the fuel and 0.01-1.0 weight per cent based on the gasoline of a copolymer of decyl maleate and vinyl acetate having a molecular weight of at least 2,000 to 30,000.
- a composition consisting essentially of gasoline, sufiicient tetraethyi lead to increase the antiknock properties of the fuel and 0.01-1.0 weight per cent based on the gasoline of a polymerized '4' methacrylie acid ester having a molecular weight of at least 2,000 to 00,000.
- composition consisting essentially of a motor fuel ofthe gasbline'typ'e containing up to 4 cc. of lead tetraethyl sufllcient to increase the antiknock properties of the fuel per gallon and from 0.01 to 1.0 weight percent of a polymerized ester of an alpha-beta unsaturated acid ester having a molecular weight of at least 2,000 to 30,000.
- a gasoline-containing motor fuel containing tetraethyl lead in-v amounts sufllcient to impart antiknock properties to said motor fuel and from 0.01 to 1.0 weight per cent of a polymerized ester of an alpha-beta unsaturated acid having a molecular weight of at least 2,000 to 30,000.
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)
- Liquid Carbonaceous Fuels (AREA)
Description
Patented may 10,- 1949 2,469,737 nnm'rrou AGENT Foa GASOLINE .1 11930. Ml Nab, Cranford, and Barry W. Budd.
.. Nb-00mins;
This invention relates to motor-fuels?antler e lates more particularly to the stabilization-of tetraethyl lead in motor fuels.
mide, ethylene dichloride and other substances. in order to, increase the antiknock value of the motor fuel. Most of the gasoline now being sold contains some of this fluid, the amount varying from about 1-3 ccs. per gallon of gasoline. Fuel for special purposes such as aviation gasoline may contain even more. v
It has been found that upon storage, and especially upon exposure to sunlight, the tetraethyl lead tends to deteriorate or decompose with the production'of a haze or cloud formation in the gasoline and with subsequent deposition of a white precipitate. These lead deposits are most noticeable in sight glasses and in the glass bowls of gasoline pumps which become fouled and require frequent cleaning. Loss of the lead compound through precipitation also tends to lower the antiknock value of the motor fuel.
It has now been found that the addition of a' very small amount of the product obtained by the polymerization of alpha-beta unsaturated acid esters will stabilize the lead tetraethyl and retard deposition of deteriorated or partially decomposed tetraethyl lead, and furthermore will prevent the corrosion of metals in contact with wet fuel containing lead tetraethyl.
Polymerized alpha-beta unsaturated esters which may be employed in accordance with our invention to stabilize lead tetraethyl include polymerized esters of acrylic acid, methacrylic acid, fumaric acid, maleic acid, itaconic acid and mesaconic acid and polymerized vinyl esters of fatty acids. These polymers should have a molecular weight of 2,000 to 30,000 or even higher and should be soluble in motor fuel.
The amount of stabilizer used depends on theamount of tetraethyl lead in the gasoline. It has been found that ordinarily 0.1 to 1% by weight of the above stabilizers based on the total weight of gasoline is sufficient for most purposes.
The stabilizers may be added to the gasoline directly or, if necessary, dissolved in a suitable solvent and then added to the gasoline in desired proportions.
The stabilizers may also be added to motor fuel adjuncts such as benzene or alcohol, antioxidants, solvent oils, deactivators etc., or with metal salts of acidic cyanic compounds etc.
These stabilizers may be added directly to the ethyl fluid with additional amounts of solvent, if necessary, and sold and shipped in this form. In this way the addition of tetraethyl lead to gasoline and addition of stabilizer occur simulta.
' conditions Jthe tetraethyl lead. In these tests a sample of arlz, J1, asslgnors to Standard 011 ompany,
a corporation of Dela- Application December 14, 1940, Serlalz1No.'716,432 v 116mm; (Cl 44-459) usavoiding any chance of decompositer the addition of ethyl fluid. -n--:or der to illustrate the effectiveness of these It is common practice to add to motor fuels a' jj. stabilizers, a number of them were tested under fluid composition consisting principally of tetraethyl lead and small'amounts of ethylene dibrotending to cause the decomposition of commercial aviation motor fuel containing 4 cc. of lead tetraethyl in a clear glass bottle was exposed to direct sunlight. Samples of the same gasoline but containing 0.01, 0.1 and 1.0% of various stabilizers of this invention were also exposed to the direct sunlight in the same manner.
' The results are given in the following table.
Concentra- Precipitation 0n Extion Wt. Per posure to Sunlight Polymer Cent Based on the Gasoline 1 Day 7 Days A commercial methyacrylic 0. 01 trace..- heavy.
polymer having a molecu- 0. 10 none o.
ler weight of about 15,000 1.0 ...do.. light.
repared by Rohm and aas.
An ester formed from l'u- 0. 01 traced" heavy.
maric acid and an alcohol with 1% benzoyl peroxide for 15 hours at 80 C. hav- 0. 10 none. medium.
lug a molecular weight of 1.0 -.do...- light.
about 2,000. Copolymer of decyl maleate- 0.01 none very light.
vinyl acetate. 0. 10 do none.
Y 1. 0 ..do. Do. hone heavy... very heavy.
1 Prepared by polymerizing a vinyl acetate with 1% benzoyl peroxide in 70% mineral oil solution for 16-24 hours at 80 C. and has a molecular weight of about commercial aviation fuel containing 4 cc. lead) stored in contact with polished steel test strips is indicated by the following data.
Cone Corrosion of Iron Test Strip Polymer Wt. Per
Cent 1 Day 7 Days A commercial methyacrylic 0. 10 Mediunn Heavy. polymer having a molec- 1.0 .....do -Do. ular weight of about 15,000 prepared by Rohm and Haas. An ester formed from i'u- 0. 10 Very Light" Medium. maric acid and an alcohol 1.0 -...-do Light. with 1% benzoyl peroxide for 15 hours at 80 C. having a molecular weight of about 2,000. Copolymer ofdecylmaleat Very Light.
and vinyl acetate. None. None Heavy Very Heavy;
The nature and objects of the present invention having been thus described and illustrated,
- what is claimed as new and useful and is desired to be secured by Letters Patent is:
1. A composition consisting essentially of tetraethyl lead and a small but stabilizing amount mixture of decyl maleate and ethyl lead and a small but stabilizing amountof a polymerized fumaric acid ester having a molecular weight of at least 2,000 to 30,000.
4. A composition consisting essentially of gasoline, suflicient tetraethyl lead to increase the antiknock properties'oi' the fuel and 0.01-1.0 weight per cent based on the gasoline of polymerized ester of an alpha-beta unsaturated acid having a mo; lecular weight of at least 2,000 to 30,000.
5. A composition consisting essentially of gasoline, sufilcient tetraethyl lead to increase the antiknock properties of the fuel and 0.01-1.0 weight per cent based on the gasoline of a copolymer of decyl maleate and vinyl acetate having a molecular weight of at least 2,000 to 30,000.
6. A composition consisting essentially of gasoline, sufiicient tetraethyi lead to increase the antiknock properties of the fuel and 0.01-1.0 weight per cent based on the gasoline of a polymerized '4' methacrylie acid ester having a molecular weight of at least 2,000 to 00,000.
7; A. composition consisting essentially of a motor fuel ofthe gasbline'typ'e containing up to 4 cc. of lead tetraethyl sufllcient to increase the antiknock properties of the fuel per gallon and from 0.01 to 1.0 weight percent of a polymerized ester of an alpha-beta unsaturated acid ester having a molecular weight of at least 2,000 to 30,000. v
8. A gasoline-containing motor fuel containing tetraethyl lead in-v amounts sufllcient to impart antiknock properties to said motor fuel and from 0.01 to 1.0 weight per cent of a polymerized ester of an alpha-beta unsaturated acid having a molecular weight of at least 2,000 to 30,000.
9. Gasoline containing about 4 cc. of tetraethyl lead per gallon and 0.01 to 1.0 weight per cent of a polymerized ester of an alpha-beta unsaturated acid having a molecular weight of at No references cited.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US716432A US2469737A (en) | 1946-12-14 | 1946-12-14 | Addition agent for gasoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US716432A US2469737A (en) | 1946-12-14 | 1946-12-14 | Addition agent for gasoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2469737A true US2469737A (en) | 1949-05-10 |
Family
ID=24877969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US716432A Expired - Lifetime US2469737A (en) | 1946-12-14 | 1946-12-14 | Addition agent for gasoline |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2469737A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2800401A (en) * | 1955-08-24 | 1957-07-23 | Shell Dev | Hydrocarbon compositions |
| US2892690A (en) * | 1955-03-22 | 1959-06-30 | California Research Corp | Compounded hydrocarbon fuels |
| US2927013A (en) * | 1956-03-29 | 1960-03-01 | California Research Corp | Fuel composition |
| US2938775A (en) * | 1956-12-06 | 1960-05-31 | Exxon Research Engineering Co | Hydrocarbon oils containing ashless dispersant inhibitors |
| US2958590A (en) * | 1957-10-15 | 1960-11-01 | Exxon Research Engineering Co | Stabilized hydrocarbon fuel oil composition |
| US2982628A (en) * | 1955-12-01 | 1961-05-02 | Shell Oil Co | Gasoline fuel compositions |
| US3010810A (en) * | 1955-03-22 | 1961-11-28 | California Research Corp | Compounded hydrocarbon fuels |
| US3033662A (en) * | 1957-08-01 | 1962-05-08 | Eastman Kodak Co | Gasoline with copolymeric lead stabilizer and a synergistic modification thereof |
| US3037851A (en) * | 1956-06-28 | 1962-06-05 | Du Pont | Stabilized leaded gasoline |
| US3126260A (en) * | 1959-05-28 | 1964-03-24 | Qgganic liquid composition |
-
1946
- 1946-12-14 US US716432A patent/US2469737A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892690A (en) * | 1955-03-22 | 1959-06-30 | California Research Corp | Compounded hydrocarbon fuels |
| US3010810A (en) * | 1955-03-22 | 1961-11-28 | California Research Corp | Compounded hydrocarbon fuels |
| US2800401A (en) * | 1955-08-24 | 1957-07-23 | Shell Dev | Hydrocarbon compositions |
| US2982628A (en) * | 1955-12-01 | 1961-05-02 | Shell Oil Co | Gasoline fuel compositions |
| US2927013A (en) * | 1956-03-29 | 1960-03-01 | California Research Corp | Fuel composition |
| US3037851A (en) * | 1956-06-28 | 1962-06-05 | Du Pont | Stabilized leaded gasoline |
| US2938775A (en) * | 1956-12-06 | 1960-05-31 | Exxon Research Engineering Co | Hydrocarbon oils containing ashless dispersant inhibitors |
| US3033662A (en) * | 1957-08-01 | 1962-05-08 | Eastman Kodak Co | Gasoline with copolymeric lead stabilizer and a synergistic modification thereof |
| US2958590A (en) * | 1957-10-15 | 1960-11-01 | Exxon Research Engineering Co | Stabilized hydrocarbon fuel oil composition |
| US3126260A (en) * | 1959-05-28 | 1964-03-24 | Qgganic liquid composition |
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