US3359087A - Motor fuel containing an octane appreciator - Google Patents
Motor fuel containing an octane appreciator Download PDFInfo
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- US3359087A US3359087A US785137A US78513759A US3359087A US 3359087 A US3359087 A US 3359087A US 785137 A US785137 A US 785137A US 78513759 A US78513759 A US 78513759A US 3359087 A US3359087 A US 3359087A
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- octane
- aldehyde
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- 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
- C10L1/18—Organic compounds containing oxygen
- C10L1/19—Esters ester radical containing compounds; ester ethers; carbonic acid esters
- C10L1/191—Esters ester radical containing compounds; ester ethers; carbonic acid esters of di- or polyhydroxyalcohols
Definitions
- This invention relates to a hydrocarbon fuel composition of high octane rating. More specifically, it involves the discovery that the octane rating of leaded gasoline fuel is substantially improved by the addition of aldehyde dialkanoates.
- Catalytic cracking and catalytic reforming which are the most widely used refining operations in the production of high octane fuels, produce substantial quantities of aromatics; catalytic cracking also produces a substantial amount of olefins. It is well known that olefins and aromatics, although possessing high octane ratings have a poorer response to organo-lead compounds such as tetraethyl lead than saturated aliphatic gasoline components. Accordingly, as the aromatic and olefinic content of the gasolines have increased to meet the octane levels required by modern automotive high compression engines, the lead response of the resulting fuels has diminished.
- the octane increment obtainable by the addition of an organo-lead compound decreases as the aromatic and olefin contents of the base fuel increase.
- the subject invention involves the discovery that the octane rating of leaded motor fuels containing a substantial concentration of high octane aromatic and/or olefinic components is markedly improved by the addition of a small amount of an aldehyde dialkanoate.
- hydrocarbyl monocarboxylic acids substantially raise the octane rating of a motor fuel containing an organo-lead antiknock agent in a substantial concentration of high octane components which may be aromatic hydrocarbons, olefinic hydrocarbons, or mixtures thereof.
- the high octane hydrocarbon motor fuels of this in vention comprise high octane components including a substantial concentration of aromatic hydrocarbons, olefinic hydrocarbons, or mixtures thereof, an organo-lead anti-knock agent, and aldehyde dialkanoates in a concentration of at least 0.1 volume percent of the fuel.
- aldehyde dialkanoates in raising the octane rating of gasoline is characterized by several unusual features.
- the aldehyde dialkanoates appear to be ineffective in raising the octane rating of gasolines unless an organo-lead anti-knock agent, normally tetraethyl lead, is a component of the gasoline mixture.
- the second unusual characteristic of the action of aldehyde dialkanoates in appreciating the octane rating of gasolines is the fact that an equivalent concentration of additive appears to cause a greater octane improvement above the 100 octane level than below the 100 octane level.
- aldehyde dialkanoates appear to have substantially no effect on the octane rating of a gasoline consisting essentially of saturated aliphatic hydrocarbons even though an organo-lead anti-knock agent is present. Since organolead anti-knock agents exert their greatest octane appreciation in predominantly saturated paraffiuic base hydrocarbon gasolines and have the least effect on the octane rating of aromaticand olefin-rich gasolines, the present invention neatly complements tetraethyl lead as an octane improver. Aldehyde dialkanoates have their minimum effect where tetraethyl lead has its maximum effect and exert their maximum effect on octane values where tetraethyl lead has its minimum effect.
- novel fuel compositions of this invention have a minimum concentration of aromatic and/or olefin components of at least 10 volume percent.
- the aromatic and/or olefin components of the motor fuel of the invention can constitute as high as 100 volume percent thereof but usually comprise between 20 and volume percent.
- the minimum 10 percent concentration is necessary for aldehyde dialkanoates to exert a significant octane improvement.
- the aromatic components of the motor fuel of the invention are generally supplied by catalytic reforming or catalytic cracking operation. Catalytic reformate is particularly high in aromatics.
- the olefin components of the motor fuel of the invention are derived either from thermal cracking, catalytic cracking or polymerization.
- the organo-lead reagent necessary for the action of aldehyde alkanoates as octane improvers is a tetraalkyl lead compound of the class known to possess anti-knock action.
- Tetraethyl lead is universally used as an antiknock agent but other tetraalkyl lead compounds such as tetramethyl lead, tetrabutyl lead, tetraamyl lead, tetrapropyl lead, etc., possess anti-knock properties and may be used in the fuel compositions of the invention in conjunction with aldehyde dialkanoates.
- Tetraethyl Lead Fluid is a commercial product comprising tetraethyl lead, ethylene chloride and ethylene bromide, the later two reagents being present in amounts equivalent to 1.0 theory and 0.5 theory, respectively, where theory is the stoichiometric amount required for reaction with the lead content of the tetraethyl lead.
- the organo-lead reagent is present in the fuel compositions of the invention in concentrations between 0.5 ml. per gallon up to the statutory limit of organo-lead reagent concentration which, at the present time, is 3 ml. per gallon in the case of automotive fuel and 4.6 ml. per gallon in the case of aviation fuel.
- the usual concentration of tetraethyl lead is between 1 and 3 ml. per gallon in automotive gasoline and 2 to 4.6 ml. per gallon in aviation gasoline.
- the aldehyde dialkanoates effective as octane appreciators are prepared by reacting an aldehyde such as acetaldehyde or benzaldehyde with acetic anhydride in the presence of an acid catalyst such as concentrated sulfuric acid.
- Aldehyde dialkanoates effective as octane appreciators in the fuel compositions of the invention are the following: Benzaldiacetate, benzaldipropionate, benzaldibutyrate, -.benzaldi-Lethylhexanoate, benzaldilaurate, acetaldehyde diacetate, acetaldehyde dipropionate, acetaldehyde dihexanoate, isobutyraldehyde diacetate, isobutyraldehyde diisobutyrate, isobutyraldehyde dipropionate, 2-ethylhexaldehyde diacetate, 2-ethylhexaldehyde diisobutyrate, Zcthylhexaldehyde dipropionate, .furfuraldiacetate and furfuraldipropionate.
- the preferred aldehyde dialkanoates used in the fuel compositions of the invention are derived from aldehydes containing 1-8 carbon atoms and from .aliphatic monocarboxylic acids containing 1-8 carbon atoms.
- Preferred aldehyde dialkanoates are acetaldehyde diacetate, benzaldiacetate, ;benzaldipropiona-te, acetaldehyde dipropionate, propionaldehyde diacetate and furfuraldiacetate.
- the aldehyde dialkanoates must be present in the'leaded aromatic and/or olefin-containing compositions of the invention in a minimum concentration of 0.1 volume percent :before a significant octane appreciation is realized.
- concentration of aldehyde dialkanoates is below 0.1 volume percent, no .octane improvement is obtained in leaded gasoline containing 10 or more volume percent aromatics and/or olefins.
- the preferred concentration of aldehyde .dialkanoates in the fuel compositions of the invention fall between 0.2 and 2.0 volume percent with maximum octane appreciation generally being obtained at concentrations between about 0.5 and 1.5 volume percent.
- Base fuel 105.0 Base fuel +0.25 v. percent benaldiacetate 105.6 Base fuel +0.5 v. percent benzaldiacetate 106.3 .Base fuel +1.0 v. percent benzaldiacetate 107.4
- This commercial premium base fuel contained 3 cc. of TEL per gallon and had an RON of 99.0.
- Base fuel +1.0 v. percent acetaldehyde diac etate s- 100.2
- Base fuel +0.5 v. percent furfuraldiacetate 99.3
- Base fuel +1.0 v. percent furfural diacetate 99.4
- a hydrocarbon fuel in the gasoline boiling range containing an organo-lead anti-knock agent, at least 10 volume percent of-high octane components selected from the group consisting of olefinic hydrocarbons, aromatic hydrocarbons and mixtures thereof and analdehyde dialkanoate in a concentration of 0.1 to 5.0 volume percent, said concentration being sufficient to effect substantial improvement of the octane rating of said hydrocarbon fuel said aldehyde dialkanoate having the general formula:
- R is selected from the group consisting of a hydrocarbyl radical containing 1-12 carbon atoms and the furyl radical and R is an aliphatic hydrocarbyl radical containing 1-12 and preferably 1-8 carbon atoms.
- a hydrocarbon fuel according to claim 3 containing 1.0 to 4.6 cc. of tetraethyl lead per gallon.
- a hydrocarbon fuel according to claim 3 is which said aldehyde dialkanoate is furfural diacetate.
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- Health & Medical Sciences (AREA)
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- Liquid Carbonaceous Fuels (AREA)
Description
United States Patent ()fiice 3,35%,87 Patented Dec. 19, 1967 No Drawing. Filed Jan. 6, 1959, Ser. No. 785,137 10 Claims. (Cl. 44-69) This invention relates to a hydrocarbon fuel composition of high octane rating. More specifically, it involves the discovery that the octane rating of leaded gasoline fuel is substantially improved by the addition of aldehyde dialkanoates.
The recent increases in compression ratios of automobile engines have placed a severe strain on petroleum refiners to produce fuelshaving the octane rating demanded by these engines. Premium fuels at the present time have a Research Octane Rating between 97 and 100 and it has been predicted that premium fuels will require octane ratings between 105 and 110 five years from now in order to satisfy the octane requirements of the high compression automotive engines predicted for that date. In order to produce premium fuels of octane ratings of 97 and above, it has been necessary for refiners to rely heavily on catalytic refining operations such as fluid catalytic cracking, catalytic reforming, alkylation and catalytic isomerization.
Catalytic cracking and catalytic reforming, which are the most widely used refining operations in the production of high octane fuels, produce substantial quantities of aromatics; catalytic cracking also produces a substantial amount of olefins. It is well known that olefins and aromatics, although possessing high octane ratings have a poorer response to organo-lead compounds such as tetraethyl lead than saturated aliphatic gasoline components. Accordingly, as the aromatic and olefinic content of the gasolines have increased to meet the octane levels required by modern automotive high compression engines, the lead response of the resulting fuels has diminished. Stated another way, the octane increment obtainable by the addition of an organo-lead compound decreases as the aromatic and olefin contents of the base fuel increase. The subject invention involves the discovery that the octane rating of leaded motor fuels containing a substantial concentration of high octane aromatic and/or olefinic components is markedly improved by the addition of a small amount of an aldehyde dialkanoate.
In our commonly assigned copending application Ser. No. 689,466 filed Oct. 11, 1957, it is disclosed that hydrocarbyl monocarboxylic acids substantially raise the octane rating of a motor fuel containing an organo-lead antiknock agent in a substantial concentration of high octane components which may be aromatic hydrocarbons, olefinic hydrocarbons, or mixtures thereof. Another commonly assigned copending a plication, Ser. No. 699,944 filed Dec. 2, 1957, discloses that t-alkyl esters of monocarboxylic acids have a similar octane appreciating action on leaded fuels of prescribed composition. This invention involves the discovery that another class of esters are effective octane appreciators in leaded fuels of prescribed composition.
The high octane hydrocarbon motor fuels of this in vention comprise high octane components including a substantial concentration of aromatic hydrocarbons, olefinic hydrocarbons, or mixtures thereof, an organo-lead anti-knock agent, and aldehyde dialkanoates in a concentration of at least 0.1 volume percent of the fuel.
The action of aldehyde dialkanoates in raising the octane rating of gasoline is characterized by several unusual features. In the first instance, the aldehyde dialkanoates appear to be ineffective in raising the octane rating of gasolines unless an organo-lead anti-knock agent, normally tetraethyl lead, is a component of the gasoline mixture.
The second unusual characteristic of the action of aldehyde dialkanoates in appreciating the octane rating of gasolines is the fact that an equivalent concentration of additive appears to cause a greater octane improvement above the 100 octane level than below the 100 octane level.
The third unusual feature of the action of aldehyde dialkanoates is that they appear to have substantially no effect on the octane rating of a gasoline consisting essentially of saturated aliphatic hydrocarbons even though an organo-lead anti-knock agent is present. Since organolead anti-knock agents exert their greatest octane appreciation in predominantly saturated paraffiuic base hydrocarbon gasolines and have the least effect on the octane rating of aromaticand olefin-rich gasolines, the present invention neatly complements tetraethyl lead as an octane improver. Aldehyde dialkanoates have their minimum effect where tetraethyl lead has its maximum effect and exert their maximum effect on octane values where tetraethyl lead has its minimum effect.
The novel fuel compositions of this invention have a minimum concentration of aromatic and/or olefin components of at least 10 volume percent. The aromatic and/or olefin components of the motor fuel of the invention can constitute as high as 100 volume percent thereof but usually comprise between 20 and volume percent. The minimum 10 percent concentration is necessary for aldehyde dialkanoates to exert a significant octane improvement.
The aromatic components of the motor fuel of the invention are generally supplied by catalytic reforming or catalytic cracking operation. Catalytic reformate is particularly high in aromatics. The olefin components of the motor fuel of the invention are derived either from thermal cracking, catalytic cracking or polymerization.
The organo-lead reagent necessary for the action of aldehyde alkanoates as octane improvers is a tetraalkyl lead compound of the class known to possess anti-knock action. Tetraethyl lead is universally used as an antiknock agent but other tetraalkyl lead compounds such as tetramethyl lead, tetrabutyl lead, tetraamyl lead, tetrapropyl lead, etc., possess anti-knock properties and may be used in the fuel compositions of the invention in conjunction with aldehyde dialkanoates.
The tetraethyl lead mixtures commercially available for automotive use contain an ethylene chloride-ethylene bromide mixture as a scavenger for removing lead from the combustion chamber in the form of volatile lead halides. Tetraethyl Lead Fluid is a commercial product comprising tetraethyl lead, ethylene chloride and ethylene bromide, the later two reagents being present in amounts equivalent to 1.0 theory and 0.5 theory, respectively, where theory is the stoichiometric amount required for reaction with the lead content of the tetraethyl lead.
The organo-lead reagent is present in the fuel compositions of the invention in concentrations between 0.5 ml. per gallon up to the statutory limit of organo-lead reagent concentration which, at the present time, is 3 ml. per gallon in the case of automotive fuel and 4.6 ml. per gallon in the case of aviation fuel. The usual concentration of tetraethyl lead is between 1 and 3 ml. per gallon in automotive gasoline and 2 to 4.6 ml. per gallon in aviation gasoline.
The aldehyde dialkanoates which are effective in increasing the octane rating of an aromatic and/ or olefincontaining leaded gasoline have the general formula: RCH=(OOCR) wherein R is selected from the group consisting of a hydrocarbyl radical containing 1-12 carbon atoms and a furyl radical and R is an aliphatic hydrocarbyl radical containing 1-12 and preferably 1-8 carbon atoms; the two Rs can be the same or different aliphatic h-ydrocarbyl radicals. The aldehyde dialkanoates effective as octane appreciators are prepared by reacting an aldehyde such as acetaldehyde or benzaldehyde with acetic anhydride in the presence of an acid catalyst such as concentrated sulfuric acid.
Aldehyde dialkanoates effective as octane appreciators in the fuel compositions of the invention are the following: Benzaldiacetate, benzaldipropionate, benzaldibutyrate, -.benzaldi-Lethylhexanoate, benzaldilaurate, acetaldehyde diacetate, acetaldehyde dipropionate, acetaldehyde dihexanoate, isobutyraldehyde diacetate, isobutyraldehyde diisobutyrate, isobutyraldehyde dipropionate, 2-ethylhexaldehyde diacetate, 2-ethylhexaldehyde diisobutyrate, Zcthylhexaldehyde dipropionate, .furfuraldiacetate and furfuraldipropionate.
The preferred aldehyde dialkanoates used in the fuel compositions of the invention are derived from aldehydes containing 1-8 carbon atoms and from .aliphatic monocarboxylic acids containing 1-8 carbon atoms. Preferred aldehyde dialkanoates are acetaldehyde diacetate, benzaldiacetate, ;benzaldipropiona-te, acetaldehyde dipropionate, propionaldehyde diacetate and furfuraldiacetate.
The aldehyde dialkanoates must be present in the'leaded aromatic and/or olefin-containing compositions of the invention in a minimum concentration of 0.1 volume percent :before a significant octane appreciation is realized. When the concentration of aldehyde dialkanoates is below 0.1 volume percent, no .octane improvement is obtained in leaded gasoline containing 10 or more volume percent aromatics and/or olefins. The preferred concentration of aldehyde .dialkanoates in the fuel compositions of the invention fall between 0.2 and 2.0 volume percent with maximum octane appreciation generally being obtained at concentrations between about 0.5 and 1.5 volume percent. Although concentrations of aldehyde dialkanoates as high as 5 volume percent may be employed with accompanying octane appreciation, economic considerations preclude the use of such high concentrations. In addition, it appears there is a fall-off in octane appreciation after the concentration of the aldehyde dialkanoate exceeds about 1.5 volume percent.
In the following table there is shown the effectiveness of aldehyde dialkanoates as octane apprecia-tors in a leaded base fuel comprising approximately percent n-butane, 40 percent isobutane-isobutylene alkylate, 10 percent pentenes from fluid catalytically cracked naphtha and 40 percent heavy platformate. With 3 cc. of tetraethyl lead -(TEL) per gallon, this base fuelhad a Research Octane No. (RON) of 105. Fluorescent Indicator Analysis (PIA) indicated that this base fuel had an aromatic content of approximately 35 percent and an olefinic content of approximately 6 percent, its -IBP was 90 F. and its end point was 367 F.
T able I Research octane No. Base fuel 105.0 Base fuel +0.25 v. percent benaldiacetate 105.6 Base fuel +0.5 v. percent benzaldiacetate 106.3 .Base fuel +1.0 v. percent benzaldiacetate 107.4
Base fuel +0.25 v. percent acetaldehyde diacetate 105.6 Base fuel +0.5 v. percent acetaldehyde diacetate 105.7
Base fuel +1.0 v. percent acetaldehyde diacetate 107.5 Base fuel +0.5 v. percent furfuraldiacetate 106.4 Base fuel +1.0 v. percent furfuraldiacetate 107.3
percent saturates, 30 percent olefins and 31 ercent aromatics. This commercial premium base fuel contained 3 cc. of TEL per gallon and had an RON of 99.0.
Table II Research octane N0. Base fuel 99.0 Base fuel +0.5 v. percent benzaldiacetate 99.2 Base fuel +1.0 v. percent 'benzaldiacetate 99.5
Base fuel +1.0 v. percent acetaldehyde diac etate s- 100.2 Base fuel +0.5 v. percent furfuraldiacetate 99.3 Base fuel +1.0 v. percent furfural diacetate 99.4
The specificity of aldehyde diacetates in appreciating the octane rating of leaded fuels containing the prescribed aromatic and/or olefin content was demonstrated by the fact that the polyol esters shown in Table III were ineffective in improving the octane rating of a leaded fuel containing the prescribed aromatic and/ or olefin content. Table III Polyol esters ineffective as octane appreciators in concentrations up to 1.0 vol. percent:
Sucrose octaacetate Pentaerythritol tetraacetate Ethylene glycol diformate Ethylene glycol diacetate Ethylene glycol dilaurate Ethylene glycol dimyristate Ethylene glycol dipalmitate 2,2,4-trimethyl 1,3-pentane diacetate.
Obviously, many modifications and variations of the invention as hereinbefore set forth may be made without departing from the spirit and scope thereof and, therefore, only such limitations should be imposed as are indicated in the appended claims.
We claim:
1. A hydrocarbon fuel in the gasoline boiling range containing an organo-lead anti-knock agent, at least 10 volume percent of-high octane components selected from the group consisting of olefinic hydrocarbons, aromatic hydrocarbons and mixtures thereof and analdehyde dialkanoate in a concentration of 0.1 to 5.0 volume percent, said concentration being sufficient to effect substantial improvement of the octane rating of said hydrocarbon fuel said aldehyde dialkanoate having the general formula:
wherein R is selected from the group consisting of a hydrocarbyl radical containing 1-12 carbon atoms and the furyl radical and R is an aliphatic hydrocarbyl radical containing 1-12 and preferably 1-8 carbon atoms.
2. A hydrocarbon fuel according to claim 1 in which said organo-lead anti-knockagent is present in a concen' tration between 0.5 and 4.6 cc. .per gallon.
3. A hydrocarbon fuel in the gasoline boiling range containing a tetraalkyl lead anti-knock agent in a concentration of at least 0.5 cc. per gallon, high octane components selected from the group consisting of olefinic hydrocarbons, aromatic hy-drocarbonszmd mixtures thereof in a concentration of at least 10 volume percent ofsaid fuel, and an aldehyde dialkanoate having the general formula: RCH=(OOCR.) wherein R is selected from the group consisting of a hydrocarbyl radical containing 1-12 carbon atoms andthe furyl radical and R is an aliphatic hydrocarbyl .radical containing 1-12 and preferably 1-8 carbon atoms, .said aldehyde dialkanoate being present in a concentration of 0.1 to 5.0 volume percent.
4. A hydrocarbon fuel according to claim 3 in which said aldehyde dialkanoate is present in a concentration between 0.2 and 2.0 volume percent.
5. A hydrocarbon fuel according to claim 3 in which said high octane components constitute 20-80 volume percent of said fuel.
6. A hydrocarbon fuel according to claim 3 containing 1.0 to 4.6 cc. of tetraethyl lead per gallon.
7. A hydrocarbon fuel according to claim 3 in which said aldehyde dialkanoate is benzaldiacetate.
8. A hydrocarbon fuel according to claim 3 in which said aldehyde dialkanoate is acetaldehyde diacetate.
9. A hydrocarbon fuel according to claim 3 is which said aldehyde dialkanoate is furfural diacetate.
10. A hydrocarbon fuel in the gasoline boiling range containing a tetraalkyl lead antiknock agent, substantial quantities of high octane components selected from the group consisting of olefinic hydrocarbons, aromatic hydrocarbons and mixtures thereof and ethylidene diacetate in an amount sufiicient to improve the octane rating of said hydrocarbon fuel.
References Cited UNITED STATES PATENTS 1,423,049 7/1922 Tunison 44-70 1,692,784 11/ 1928 Orelup et al 4466 2,145,889 2/1939 Prutton et al. 44-66 2,210,942 8/1940 Lipkin 44-77 6 2,228,662 1/ 1941 Holm 44-70 2,403,268 7/1946 Davis et a1 4469 2,409,156 10/1946 Schulze et al. 44-69 2,843,607 7/1958 Servigne et al. 260494 2,866,813 12/1958 McLeer 260494 2,884,315 4/1959 Barnum 44-56 FOREIGN PATENTS 72 10/ 1958 Trinidad and Tobago. 277,326 1/ 1929 Great Britain. 837,965 2/ 1939 France.
OTHER REFERENCES Improved Motors Fuels Through Selective Blending, Wagner et al., paper presented before American Petroleum Institute, Nov. 7, 1941, pp. 8-13.
DANIEL E. WYMAN, Primary Examiner.
JULIUS GREENWALD, ALPHONSO D. SULLIVAN,
Examiners.
Y. H. SMITH, Assistant Examiner.
Claims (1)
1. A HYDROCARBON FUEL IN THE GASOLINE BOILING RANGE CONTAINING AN ORGANO-LEAD ANTI-KNOCK AGENT, AT 10 VOLUME PERCENT OF HIGH OCTANE COMPONENTS SELECTED FROM THE GROUP CONSISTING OF OLEFINIC HYDROCARBONS, AROMATIC HYDROCARBONS AND MIXTURES THEREOF AND AN ALDEHYDE DIALKANOATE IN A CONCENTRATION OF 0.1 TO 5.0 VOLUME PERCENT, SAID CONCENTRATION BEING SUFFICIENT TO EFFECT SUBSTANTIAL IMPROVEMENT OF THE OCTANE RATING OF SAID HYDROCARBON FUEL SAID ALDEHYDE DIALKANOATE HAVING THE GENERAL FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US785137A US3359087A (en) | 1959-01-06 | 1959-01-06 | Motor fuel containing an octane appreciator |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US785137A US3359087A (en) | 1959-01-06 | 1959-01-06 | Motor fuel containing an octane appreciator |
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| Publication Number | Publication Date |
|---|---|
| US3359087A true US3359087A (en) | 1967-12-19 |
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| Application Number | Title | Priority Date | Filing Date |
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| US785137A Expired - Lifetime US3359087A (en) | 1959-01-06 | 1959-01-06 | Motor fuel containing an octane appreciator |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009141166A1 (en) | 2008-05-19 | 2009-11-26 | Furanix Technologies B.V. | Fuel composition |
| EP2128227A1 (en) | 2008-05-19 | 2009-12-02 | Furanix Technologies B.V | Monosubstituted furan derivatives via decarboxylation and use thereof as (aviation) fuel |
| WO2010053354A2 (en) * | 2008-11-05 | 2010-05-14 | Criss Cross Technology Bv | A motor fuel additive with enhanced properties, and processes for the production thereof |
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| GB277326A (en) * | 1927-09-06 | 1929-01-07 | Avenarius Geb | A method for preventing the knocking of motor fuel |
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| US2884315A (en) * | 1956-02-20 | 1959-04-28 | Exxon Research Engineering Co | Aviation gasoline |
-
1959
- 1959-01-06 US US785137A patent/US3359087A/en not_active Expired - Lifetime
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| US1423049A (en) * | 1920-04-12 | 1922-07-18 | Us Ind Alcohol Co | Fuel of liquid type |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009141166A1 (en) | 2008-05-19 | 2009-11-26 | Furanix Technologies B.V. | Fuel composition |
| EP2128226A1 (en) | 2008-05-19 | 2009-12-02 | Furanix Technologies B.V | Fuel component |
| EP2128227A1 (en) | 2008-05-19 | 2009-12-02 | Furanix Technologies B.V | Monosubstituted furan derivatives via decarboxylation and use thereof as (aviation) fuel |
| US20110107659A1 (en) * | 2008-05-19 | 2011-05-12 | Furanix Technologies B.V. | Fuel composition |
| US8435313B2 (en) | 2008-05-19 | 2013-05-07 | Furanix Technologies, B.V. | Fuel composition |
| US9145526B2 (en) | 2008-05-19 | 2015-09-29 | Furanix Technologies B.V. | Process for preparing fuel compositions |
| WO2010053354A2 (en) * | 2008-11-05 | 2010-05-14 | Criss Cross Technology Bv | A motor fuel additive with enhanced properties, and processes for the production thereof |
| WO2010053354A3 (en) * | 2008-11-05 | 2010-11-04 | Criss Cross Technology Bv | A motor fuel additive with enhanced properties, and processes for the production thereof |
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