US3080221A - Fuels for internal combustion engines - Google Patents
Fuels for internal combustion engines Download PDFInfo
- Publication number
- US3080221A US3080221A US84525A US8452561A US3080221A US 3080221 A US3080221 A US 3080221A US 84525 A US84525 A US 84525A US 8452561 A US8452561 A US 8452561A US 3080221 A US3080221 A US 3080221A
- Authority
- US
- United States
- Prior art keywords
- boron
- fuels
- internal combustion
- gasoline
- combustion engines
- 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
- 239000000446 fuel Substances 0.000 title claims description 18
- 238000002485 combustion reaction Methods 0.000 title claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001639 boron compounds Chemical class 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 description 27
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 24
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical group CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 239000006079 antiknock agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- QCIFLGSATTWUQJ-UHFFFAOYSA-N n,4-dimethylaniline Chemical compound CNC1=CC=C(C)C=C1 QCIFLGSATTWUQJ-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- -1 lead tetraethyl Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- MLPVBIWIRCKMJV-UHFFFAOYSA-N o-aminoethylbenzene Natural products CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
-
- 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
-
- 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
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
- C10L1/301—Organic compounds compounds not mentioned before (complexes) derived from metals
- C10L1/303—Organic compounds compounds not mentioned before (complexes) derived from metals boron compounds
-
- 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
- C10L1/30—Organic compounds compounds not mentioned before (complexes)
- C10L1/305—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond)
- C10L1/306—Organic compounds compounds not mentioned before (complexes) organo-metallic compounds (containing a metal to carbon bond) organo Pb compounds
Definitions
- the present invention relates to'fuels for internal comb'ustion engines of the spark ignition type, especially to motor fuels for cars and airplanes; more particularly it concerns motor fuels consisting of gasoline or mixtures 'ofgasoline' and benzene.
- these fuels contain "boroncompounds of the general formula B'AHI3 wherein the three Ar represent the same or different aromatic radicals which are substituted by at least three aliphatic hydrocarbon radicals having 1-10 carbon atoms, two of the hydrocarbon radicals being in o,o-position to the boron atom.
- boron compounds of the above general formula Owing to the presence of boron compounds of the above general formula the tendency of the motor fuels to form deposits in the combustion engines is minimized. This applies particularly to motor fuels which contain anti-knock agents, for instance lead compounds such as lead tetraethyl, or aromatic amines such as monomethyl aniline, N-methyl-p-toluidine and xylidine or mixtures thereof. Furthermore the boron compounds improve the octane number of the fuels and prevent the progressive increase in the minimum requirements for the fuels on prolonged operation of the engines.
- anti-knock agents for instance lead compounds such as lead tetraethyl, or aromatic amines such as monomethyl aniline, N-methyl-p-toluidine and xylidine or mixtures thereof.
- the boron compounds improve the octane number of the fuels and prevent the progressive increase in the minimum requirements for the fuels on prolonged operation of the engines.
- Suitable boron compounds of the formula indicated are for instance boron trimesityl of the formula CHa and boron triduryl of the formula CHa H; C- CH;
- the conte'ntfof the boron compounds in the fuels may vary'within'wide limits. It may for instance amount to .001%-5% by volume.
- the ratios depend in the first place upon the content of the anti-knock agents in the motor fuels; suitable ratios can easily be determined by preliminarytes'ts. I, g V
- Example 1 A gasoline whose physico-chemical data are indicated below was mixed with.03% by volume of lead tetraethyl and 05% by volume of boron trimesityl, boron tris triisopropylphenyl or boron triduryl. With this fuel afour cylinder'motor was'operated under ch'angingload for 25 hours without interruption. After this time only about 5% of the surface of the pistons were covered with a light, very thin weakly brownish coating. The pistons did not show further alterations. On the bottom of the pistons and on the walls of the combustion cham bers a slight coating of a white greyish powder was observed, but no hard carbonaceous deposits of combustion residues were present. In the suction system no alterations could be observed.
- the physico-chemical data of the gasoline used were as follows.
- Example 2 A gasoline having the same physico-chamical data as the gasoline of Example 1 but which did not contain lead tetraethyl was mixed with .5'% by volume of boron trimesityl.
- the octane number determined by the F method (ASTM D90851) in the IG-motor test amounted to 71.1; with the addition of 1% by volume of boron trimesityl it amounted to 71.6 whereas without the addition of boron trimesityl the octane number was 70.7.
- boron compounds of the invention exhibit in the motor fuels. If for instance a solution of 5 g. of boron trimesityl, 5g. of boron tristriisopropylphenyl or 5 g. of boron triduryl in 60 ml. of a benzene-ligroin mixture is shaken with 40 ml. of water and kept standing at room temperature for 70 hours, no hydrolysis of the boron compounds can be observed. If however a solution of 5 g. of boron triphenyl in 60 m1. of a benzene-ligroin mixture is shaken with 40 ml. of Water and kept standing at room temperature for 70 hours, 29% by weight of the boron tri phenyl are hydrolysed and have become inefficient.
- a motor fuel for an internal combustion engine of the spark ignition type comprising a component selected from the group consisting of gasoline, benzene, and an admixture of gasoline and benzene, together with about .001% to 5% by volume of a boron compound having the general formula B-AR wherein Ar represents an aromatic radical having at least three aliphatic hydrocarbon substituents having from A ⁇ a about 1 to 10 carbon atoms, twobf said aliphatic hy drocarbon substituents being in o,o-position with respect to the boron atom.
- boron compound is selected from the group consisting of boron trimesityl, boron tristriisopropylphenyl and boron triduryl.
- a motor fuel according to claim 1 containing at least one antiknock additive selected from the group consisting of lead tetraethyl, monoethyl aniline, N-methylp-toluidine, and xylidine.
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)
- Catalysts (AREA)
Description
United States Patent Office 3,080,221 Patented Man- 5, 1 963 3,080,221 FUELS FOR INTERNAL COMBUSTION ENGINES "Karl Niitz'el, Koln-S tammheim, and Rudolf Stroh, Eugen Hiinri'l'en, arid Walter Lohrn'ar, Leverkusen, Germany, -assignors to Farbenfabriken Bayer Aktieng'esellsc'haft,
Leverkusen, Germany, a corporation of Germany No Drawing. Filed Jan. 24, 1961, Ser. No. 84,525
The present invention relates to'fuels for internal comb'ustion engines of the spark ignition type, especially to motor fuels for cars and airplanes; more particularly it concerns motor fuels consisting of gasoline or mixtures 'ofgasoline' and benzene. According to the invention these fuels contain "boroncompounds of the general formula B'AHI3 wherein the three Ar represent the same or different aromatic radicals which are substituted by at least three aliphatic hydrocarbon radicals having 1-10 carbon atoms, two of the hydrocarbon radicals being in o,o-position to the boron atom.
Owing to the presence of boron compounds of the above general formula the tendency of the motor fuels to form deposits in the combustion engines is minimized. This applies particularly to motor fuels which contain anti-knock agents, for instance lead compounds such as lead tetraethyl, or aromatic amines such as monomethyl aniline, N-methyl-p-toluidine and xylidine or mixtures thereof. Furthermore the boron compounds improve the octane number of the fuels and prevent the progressive increase in the minimum requirements for the fuels on prolonged operation of the engines.
Suitable boron compounds of the formula indicated are for instance boron trimesityl of the formula CHa and boron triduryl of the formula CHa H; C- CH;
These compounds can be obtained by reacting boron ,trifluoride with the Grign ard compounds of trimesityl- :chl oride, triisopropylph'enylchloride or durylchloride in known manner. H
The conte'ntfof the boron compounds in the fuels ma vary'within'wide limits. It may for instance amount to .001%-5% by volume. The ratios depend in the first place upon the content of the anti-knock agents in the motor fuels; suitable ratios can easily be determined by preliminarytes'ts. I, g V
I The following examples serve to illustrate theinventi'on without, however,lim'iting'the scope thereof.
Example 1 A gasoline whose physico-chemical data are indicated below was mixed with.03% by volume of lead tetraethyl and 05% by volume of boron trimesityl, boron tris triisopropylphenyl or boron triduryl. With this fuel afour cylinder'motor was'operated under ch'angingload for 25 hours without interruption. After this time only about 5% of the surface of the pistons were covered with a light, very thin weakly brownish coating. The pistons did not show further alterations. On the bottom of the pistons and on the walls of the combustion cham bers a slight coating of a white greyish powder was observed, but no hard carbonaceous deposits of combustion residues were present. In the suction system no alterations could be observed.
The physico-chemical data of the gasoline used were as follows.
When the test was carried out under equal conditions with the same gasoline and with the addition of .03% by volume of lead tetraethyl but Without the addition of boron trimesityl, boron tristriisopropylphenyl or boron triduryl 22% of the surface of the pistons were covered with a lacquer-like coating and the bottom of the pistons as Well as the walls of the combustion chambers were covered with hard carbonaceous combustion residues.
If .05% by volume of boron triphenyl which is known as additive to motor fuels, was aplied instead of the boron compounds of the invention, 17% of the surface of the pistons were covered with a lacquer-like coating; besides, disturbances occurred in the carburetor on account of cloudy precipitates.
Example 2 A gasoline having the same physico-chamical data as the gasoline of Example 1 but which did not contain lead tetraethyl was mixed with .5'% by volume of boron trimesityl. The octane number determined by the F method (ASTM D90851) in the IG-motor test amounted to 71.1; with the addition of 1% by volume of boron trimesityl it amounted to 71.6 whereas without the addition of boron trimesityl the octane number was 70.7.
When instead of .5% by volume of boron trimesityl the same amount of boron tristriisopropylphenyl or boron triduryl was applied the octane number was 72.7 or 72.1 respectively. 1 r
Very remarkable is the stability the boron compounds of the invention exhibit in the motor fuels. If for instance a solution of 5 g. of boron trimesityl, 5g. of boron tristriisopropylphenyl or 5 g. of boron triduryl in 60 ml. of a benzene-ligroin mixture is shaken with 40 ml. of water and kept standing at room temperature for 70 hours, no hydrolysis of the boron compounds can be observed. If however a solution of 5 g. of boron triphenyl in 60 m1. of a benzene-ligroin mixture is shaken with 40 ml. of Water and kept standing at room temperature for 70 hours, 29% by weight of the boron tri phenyl are hydrolysed and have become inefficient.
What We claim:
'1. A motor fuel for an internal combustion engine of the spark ignition type, comprising a component selected from the group consisting of gasoline, benzene, and an admixture of gasoline and benzene, together with about .001% to 5% by volume of a boron compound having the general formula B-AR wherein Ar represents an aromatic radical having at least three aliphatic hydrocarbon substituents having from A} a about 1 to 10 carbon atoms, twobf said aliphatic hy drocarbon substituents being in o,o-position with respect to the boron atom.
2. A motor fuel according to claim 1 wherein the boron compound is selected from the group consisting of boron trimesityl, boron tristriisopropylphenyl and boron triduryl.
3. A motor fuel according to claim 1 containing at least one antiknock additive selected from the group consisting of lead tetraethyl, monoethyl aniline, N-methylp-toluidine, and xylidine.
References Cited in the file of this patent UNITED STATES PATENTS 2,410,846 Walters Nov. 12, 1946 FOREIGN PATENTS 549,075 Great Britain Nov. 5, 1942 OTHER REFERENCES Boron New Improvement Agent, an article by Hughes et al. in Refining Engineering, vol. 28, No. 7, July 1956, pages C10Cl3.
Claims (1)
1. A MOTOR FUEL FOR AN INTERNAL COMBUSTION ENGINE OF THE SPARK IGINTION TYPE, COMPRISING A COMPONENT SELECTED FROM THE GROUP CONSISTING OF GASOLINE, BENZENE, AND AN ADMIXTURE OF GASOLINE AND BENZENE, TOGETHER WITH ABOUT .001% TO 5% BY VOLUME OF A BORON COMPOUND HAVING THE GENERAL FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84525A US3080221A (en) | 1961-01-24 | 1961-01-24 | Fuels for internal combustion engines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US84525A US3080221A (en) | 1961-01-24 | 1961-01-24 | Fuels for internal combustion engines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3080221A true US3080221A (en) | 1963-03-05 |
Family
ID=22185493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US84525A Expired - Lifetime US3080221A (en) | 1961-01-24 | 1961-01-24 | Fuels for internal combustion engines |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3080221A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103421031A (en) * | 2012-05-17 | 2013-12-04 | 中国科学院化学研究所 | Temperature fluorescence probe based on triarylborane, preparation method and applications thereof |
| EP2014745B1 (en) * | 2007-07-10 | 2019-03-13 | Afton Chemical Corporation | Fuel additive concentrate comprising N-methyl-p-toluidine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB549075A (en) * | 1939-10-18 | 1942-11-05 | Standard Oil Dev Co | Improvements in or relating to motor fuels and the manufacture thereof |
| US2410846A (en) * | 1943-03-06 | 1946-11-12 | Shell Dev | Gasoline |
-
1961
- 1961-01-24 US US84525A patent/US3080221A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB549075A (en) * | 1939-10-18 | 1942-11-05 | Standard Oil Dev Co | Improvements in or relating to motor fuels and the manufacture thereof |
| US2410846A (en) * | 1943-03-06 | 1946-11-12 | Shell Dev | Gasoline |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2014745B1 (en) * | 2007-07-10 | 2019-03-13 | Afton Chemical Corporation | Fuel additive concentrate comprising N-methyl-p-toluidine |
| CN103421031A (en) * | 2012-05-17 | 2013-12-04 | 中国科学院化学研究所 | Temperature fluorescence probe based on triarylborane, preparation method and applications thereof |
| CN103421031B (en) * | 2012-05-17 | 2016-08-10 | 中国科学院化学研究所 | Temperature fluorescent probe based on triarylboron and preparation thereof and purposes |
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