US3222146A - Glycerol esters in leaded gasoline - Google Patents
Glycerol esters in leaded gasoline Download PDFInfo
- Publication number
- US3222146A US3222146A US81247A US8124761A US3222146A US 3222146 A US3222146 A US 3222146A US 81247 A US81247 A US 81247A US 8124761 A US8124761 A US 8124761A US 3222146 A US3222146 A US 3222146A
- Authority
- US
- United States
- Prior art keywords
- gasoline
- octane
- lead
- carbon atoms
- leaded
- 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
- 150000002314 glycerols Chemical class 0.000 title description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 23
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 11
- 150000002611 lead compounds Chemical class 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 239000006079 antiknock agent Substances 0.000 claims description 6
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 description 16
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 13
- 239000000446 fuel Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl lead compound Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000001087 glyceryl triacetate Substances 0.000 description 2
- 235000013773 glyceryl triacetate Nutrition 0.000 description 2
- 229960002622 triacetin Drugs 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000529895 Stercorarius Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-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
-
- 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
-
- 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
- C10L1/20—Organic compounds containing halogen
- C10L1/201—Organic compounds containing halogen aliphatic 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
- C10L1/30—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
- This invention relates to an improved gasoline composition which is of high octane number, which contains a lead compound as an anti-knocking agent, and also contains an octane rating booster.
- gasolines for use in spark-ignited internal combustion egines e.g., automotive and airplane engines have an octane number of at least 85 RON, that is, as determined by the Research Method.
- this agent is an alkyl lead compound especially a tetra-lower alkyl lead, usually a small amount within the range from about 0.5 to 3.0 cc. per gallon, or even as much as approximately 5 or 6 cc. per gallon.
- Tetraethyl lead is the most widely used anti-knock agent, and is effective in raising the octane and thereby reducing the knock caused by abnormal combustion of gasoline of inferior octane rating.
- Other lead compounds such asthe lower-alkyl lead carboxylates disclosed in copending application Serial No. 855,006, filed November 24, 1959, now abandoned, are useful as anti-knock agents.
- the quantity of lead compound which may be used in a gasoline is limited by decreasing effectiveness at higher percentages, and by the fact that lead compounds cause lead-containing deposits in the cylinders as well as by economic, health and legal considerations.
- gasolinecompatible i.e., soluble, miscible or dispersible, esters are incorporated in a leaded gasoline as an octane booster.
- the improvement in the gasoline is generally more apparent in the Motor Method of determining octane rating, although improvement also is usually observed when the octane is determined by the Research Method.
- the fuel therefore, may even have less spread between its Research Method number and its Motor Method number, and would accordingly be considered as less sensitive.
- the ester incorporated in gasoline according to this invention contains no more than 20 carbon atoms and is a triester of glycerol with a lower aliphatic acid.
- the ester or acyl groups may be alike or diiferent, straight, branched or cyclic and in general have 1-9 carbon atoms.
- the glycerol esters of acids having 2 to 5 carbon atoms, such as triacetin, tripropionin and tributyrin are preferred.
- the ester is included in the gasoline composition in the ratio of from about 1 to 50 moles of ester per mole 3,222,146 Patented Dec. 7, 1965 of lead compound and sufficient to increase the octane number of the leaded gasoline.
- the molar ratio of ester to lead compound is preferably about 2 to 30/1.
- the fuel usually contains about 0.2 to 6 volume percent of the ester, preferably about 0.4 to 4%, an amount sufficient to increase the octane rating of the fuel.
- the concentration of the additive is important in that larger percentages may decrease the octane rating of the gasoline below the rating of the base fuel.
- the optimum range of eflectiveness of the octane booster varies with the lead content of the gasoline. In general, with greater amounts of, for example, tetraethyl lead, not only is the octane increased, but the octane boosting ability of the ester is also increased and the optimum range for this additive is slightly raised.
- Gasolines are usually blends of low-boiling mineral oil hydrocarbon fractions derived by distillation, cracking, and other refining and chemical conversion processes practiced upon crude petroleum.
- the gasoline will contain varying proportions of parafiins, olefins, naphthenes and aromatics and generally will boil primarily in the range of about 100 to 425 F.
- the gasoline of this invention has an unsaturated component, i.e., olefinic and/ or aromatic, preferably aromatic, which is at least about 10 volume percent, preferably at least about 25 or 40 percent of the hydrocarbon fuel.
- a typical premium gasoline besides a small amount of lower-alkyl lead compound as an anti-knock agent may also contain small amounts of other non-hydrocarbon constituents used to impart various properties to the gasoline in its use in internal combustion engines, e.g. scavengers, corrosion inhibitors, etc.
- Such gasolines frequently have a Re search Method octane number of about -98.
- the most widely used tetra-lower-alkyl lead compound added to gasolines as an anti-knock agent is tetra-ethyl lead.
- TEL Motor Mix is used in commercial practice to add tetra-ethyl lead and scavengers to the gasoline. Motor Mix contains 59.2% tetra-ethyl lead, 13.0% ethylene dibromide, 23.9% ethylene dichloride and 3.9% hydrocarbon diluent, dyes, etc.
- a leaded gasoline consisting essentially of base hydrocarbon gasoline containing at least about 10 volume percent unsaturated hydrocarbons, a small amount of loWer-alkyl lead anti-knock agent sufficient to reduce knock and about 1 to moles per mole of lead compound of a gasoline-compatible ester containing up to 20 carbon atoms and comprising a glycerol triester of an aliphatic carboxylic acid of 1-9 carbon atoms in an amount suflicient to increase the octane number of the leaded gasoline.
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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Description
United States Patent 3,222,146 GLYCEROL ESTERS IN LEADED GASOLINE Everett N. Case, Homewood, and Seymour H. Patinkin,
Chicago, Ill., and Dennis R. Carlson, Anoka, Minn.,
assignors, by mesne assignments, to Sinclair Research Inc., New York, N.Y., a corporation of Delaware N0 Drawing. Filed Jan. 9, 1961, Ser. No. 81,247
5 Claims. (CI. 44-69) This invention relates to an improved gasoline composition which is of high octane number, which contains a lead compound as an anti-knocking agent, and also contains an octane rating booster.
By and large, modern gasolines for use in spark-ignited internal combustion egines, e.g., automotive and airplane engines have an octane number of at least 85 RON, that is, as determined by the Research Method. Almost without exception producers of gasoline use non-hydrocarbon agents to raise the octane number of the gasoline to suppress knocking. Generally this agent is an alkyl lead compound especially a tetra-lower alkyl lead, usually a small amount within the range from about 0.5 to 3.0 cc. per gallon, or even as much as approximately 5 or 6 cc. per gallon. Tetraethyl lead is the most widely used anti-knock agent, and is effective in raising the octane and thereby reducing the knock caused by abnormal combustion of gasoline of inferior octane rating. Other lead compounds, such asthe lower-alkyl lead carboxylates disclosed in copending application Serial No. 855,006, filed November 24, 1959, now abandoned, are useful as anti-knock agents. However, the quantity of lead compound which may be used in a gasoline is limited by decreasing effectiveness at higher percentages, and by the fact that lead compounds cause lead-containing deposits in the cylinders as well as by economic, health and legal considerations.
Several methods are used for determining the octane rating of a gasoline and each method usually gives a different figure; for example, the Motor Method of determining octane rating generally gives a lower figure than the Research Method. The spread between the two figures is termed the sensitivity of the fuel. Gasolines are sold on the basis of their Research Octane number but the make of the car and the type of driving determines whether it operates closer to the Motor Method or Research Method rating; however, the road octane is usually, numerically, in the space between the two. A gasoline having Motor Method and Research Method octane numbers which are closer is less sensitive to variations in operating conditions in its performance.
In accordance with this invention, certain gasolinecompatible, i.e., soluble, miscible or dispersible, esters are incorporated in a leaded gasoline as an octane booster. The improvement in the gasoline is generally more apparent in the Motor Method of determining octane rating, although improvement also is usually observed when the octane is determined by the Research Method. The fuel, therefore, may even have less spread between its Research Method number and its Motor Method number, and would accordingly be considered as less sensitive.
The ester incorporated in gasoline according to this invention contains no more than 20 carbon atoms and is a triester of glycerol with a lower aliphatic acid. The ester or acyl groups may be alike or diiferent, straight, branched or cyclic and in general have 1-9 carbon atoms. The glycerol esters of acids having 2 to 5 carbon atoms, such as triacetin, tripropionin and tributyrin are preferred.
The ester is included in the gasoline composition in the ratio of from about 1 to 50 moles of ester per mole 3,222,146 Patented Dec. 7, 1965 of lead compound and sufficient to increase the octane number of the leaded gasoline. The molar ratio of ester to lead compound is preferably about 2 to 30/1. In terms of volume, the fuel usually contains about 0.2 to 6 volume percent of the ester, preferably about 0.4 to 4%, an amount sufficient to increase the octane rating of the fuel. The concentration of the additive is important in that larger percentages may decrease the octane rating of the gasoline below the rating of the base fuel. Also, the optimum range of eflectiveness of the octane booster varies with the lead content of the gasoline. In general, with greater amounts of, for example, tetraethyl lead, not only is the octane increased, but the octane boosting ability of the ester is also increased and the optimum range for this additive is slightly raised.
Gasolines are usually blends of low-boiling mineral oil hydrocarbon fractions derived by distillation, cracking, and other refining and chemical conversion processes practiced upon crude petroleum. The gasoline will contain varying proportions of parafiins, olefins, naphthenes and aromatics and generally will boil primarily in the range of about 100 to 425 F. The gasoline of this invention has an unsaturated component, i.e., olefinic and/ or aromatic, preferably aromatic, which is at least about 10 volume percent, preferably at least about 25 or 40 percent of the hydrocarbon fuel. A typical premium gasoline besides a small amount of lower-alkyl lead compound as an anti-knock agent, may also contain small amounts of other non-hydrocarbon constituents used to impart various properties to the gasoline in its use in internal combustion engines, e.g. scavengers, corrosion inhibitors, etc. Such gasolines frequently have a Re search Method octane number of about -98. The most widely used tetra-lower-alkyl lead compound added to gasolines as an anti-knock agent is tetra-ethyl lead. Frequently, TEL Motor Mix is used in commercial practice to add tetra-ethyl lead and scavengers to the gasoline. Motor Mix contains 59.2% tetra-ethyl lead, 13.0% ethylene dibromide, 23.9% ethylene dichloride and 3.9% hydrocarbon diluent, dyes, etc.
The gasoline blends used in the samples reported in the table below included as a component a naphtha reformate distillation tower bottoms fraction which had an API gravity of 34.1 and contained 25.1% parafiins, 3.2% naphthenes and 71.7% aromatics. The fraction had an AST M distillation of:
bromine number of 35.0.
Its ASTM distillation was:
92 F Percent rec- 98. 0 133 F Percent res 1. 0 256 F Percent loss.-- 1. 0 329 F 403 F Samples of this base gasoline were obtained and mixed with 6 cc. per gallon of TEL as Motor Mix (about 0.008 mole TEL/1). A different amount of glycerol triester was added to each sample and it was tested by the Microoctane Method. The base fuel was tested before 3 each series of tests. The table below records the results of these tests.
TAB LE ctane Change Sample Additlive,
vo percent MM RM MM RM Triacetin Trlpropionin Tributyrin It'is claimed:
1. A leaded gasoline consisting essentially of base hydrocarbon gasoline containing at least about 10 volume percent unsaturated hydrocarbons, a small amount of loWer-alkyl lead anti-knock agent sufficient to reduce knock and about 1 to moles per mole of lead compound of a gasoline-compatible ester containing up to 20 carbon atoms and comprising a glycerol triester of an aliphatic carboxylic acid of 1-9 carbon atoms in an amount suflicient to increase the octane number of the leaded gasoline.
2. Gasoline according to claim 1 where the acid is acetic acid.
3. Gasoline according to claim 1 where the acid is propionic acid.
4. Gasoline according to claim 1 Where the acid is butyric acid.
5. Gasoline according to claim 1 containing about 2 to 30 moles of ester per mole of lead compound.
References Cited by the Examiner UNITED STATES PATENTS 1,692,784 11/1928 Orelup et al. 4466 1,995,615 3/1935 Jaeger 4470 3,021,205 2/1962 Chafetz et al. 4469 3,036,904 5/1962 Chafetz et al. 252386 3,083,086 3/1963 Case et al. 4469 FOREIGN PATENTS 277,326 1/ 1929 Great Britain.
640,311 3/1928 France.
OTHER REFERENCES Texaco, abstract of Australian'Patent 42,139, Oct. 8, 1958 (1 page).
DANIEL E. WYMAN, Primary'Examiner.
JULIUS GREENWALD, Examiner.
Claims (1)
1. A LEADED GASOLINE CONSISTING ESSENTIALLY OF BASE HYDROCARBON GASOLINE CONTAINING AT LEAST ABOUT 10 VOLUME PERCENT UNSATURATED HYDROCARBONS, A SMALL AMOUNT OF LOWER-ALKYL LEAD ANTI-KNOCK AGENT SUFFICIENT TO REDUCE KNOCK AND ABOUT 1 TO 50 MOLES PER MOLE OF LEAD COMPOUND OF A GASOLINE-COMPATIBLE ESTER CONTAINING UP TO 20 CARBON ATOMS AND COMPRISING A GLYCEROL TRIESTER OF AN ALIPHATIC CARBOXYLIC ACID OF 1-9 CARBON ATOMS IN AN AMOUNT SUFFICIENT TO INCREASE THE OCTANE NUMBER OF THE LEADED GASOLINE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81247A US3222146A (en) | 1961-01-09 | 1961-01-09 | Glycerol esters in leaded gasoline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81247A US3222146A (en) | 1961-01-09 | 1961-01-09 | Glycerol esters in leaded gasoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3222146A true US3222146A (en) | 1965-12-07 |
Family
ID=22163002
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US81247A Expired - Lifetime US3222146A (en) | 1961-01-09 | 1961-01-09 | Glycerol esters in leaded gasoline |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3222146A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948618A (en) * | 1975-06-05 | 1976-04-06 | Ethyl Corporation | Fuel compositions containing glycerides for reducing the plugging of exhaust gas catalysts |
| US4005992A (en) * | 1976-03-08 | 1977-02-01 | Ethyl Corporation | Novel gasoline compositions and additives therefor |
| US5632785A (en) * | 1995-12-01 | 1997-05-27 | Exxon Research & Engineering Company | Fuel economy additives |
| US6468319B1 (en) * | 1999-07-16 | 2002-10-22 | Exxonmobil Research And Engineering Co. | Diesel fuel containing ester to reduce emissions |
| US20090092712A1 (en) * | 2007-10-04 | 2009-04-09 | Nakhasi Dilip K | Controlled Viscosity Oil Composition and Method of Making |
| NL1036154C (en) * | 2008-11-05 | 2010-05-06 | Criss Cross Technology B V | A motor fuel additive with enhanced properties, and processes for the production thereof. |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR640311A (en) * | 1926-09-07 | 1928-07-10 | Avenarius Soc Geb | Method and means for preventing knocking caused by motor fuels |
| US1692784A (en) * | 1925-01-23 | 1928-11-20 | Boyce Ite Products Inc | Fuel and fuel ingredients |
| GB277326A (en) * | 1927-09-06 | 1929-01-07 | Avenarius Geb | A method for preventing the knocking of motor fuel |
| US1995615A (en) * | 1931-09-01 | 1935-03-26 | American Cyanamid & Chem Corp | Motor fuel |
| US3021205A (en) * | 1960-03-01 | 1962-02-13 | Texaco Inc | Motor fuel |
| US3036904A (en) * | 1959-09-21 | 1962-05-29 | Texaco Inc | Motor fuel containing octane appreciator |
| US3083086A (en) * | 1959-04-09 | 1963-03-26 | Sinclair Research Inc | N-propyl n-butyrate in leaded gasoline |
-
1961
- 1961-01-09 US US81247A patent/US3222146A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1692784A (en) * | 1925-01-23 | 1928-11-20 | Boyce Ite Products Inc | Fuel and fuel ingredients |
| FR640311A (en) * | 1926-09-07 | 1928-07-10 | Avenarius Soc Geb | Method and means for preventing knocking caused by motor fuels |
| GB277326A (en) * | 1927-09-06 | 1929-01-07 | Avenarius Geb | A method for preventing the knocking of motor fuel |
| US1995615A (en) * | 1931-09-01 | 1935-03-26 | American Cyanamid & Chem Corp | Motor fuel |
| US3083086A (en) * | 1959-04-09 | 1963-03-26 | Sinclair Research Inc | N-propyl n-butyrate in leaded gasoline |
| US3036904A (en) * | 1959-09-21 | 1962-05-29 | Texaco Inc | Motor fuel containing octane appreciator |
| US3021205A (en) * | 1960-03-01 | 1962-02-13 | Texaco Inc | Motor fuel |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3948618A (en) * | 1975-06-05 | 1976-04-06 | Ethyl Corporation | Fuel compositions containing glycerides for reducing the plugging of exhaust gas catalysts |
| US4005992A (en) * | 1976-03-08 | 1977-02-01 | Ethyl Corporation | Novel gasoline compositions and additives therefor |
| US5632785A (en) * | 1995-12-01 | 1997-05-27 | Exxon Research & Engineering Company | Fuel economy additives |
| US6468319B1 (en) * | 1999-07-16 | 2002-10-22 | Exxonmobil Research And Engineering Co. | Diesel fuel containing ester to reduce emissions |
| US20090092712A1 (en) * | 2007-10-04 | 2009-04-09 | Nakhasi Dilip K | Controlled Viscosity Oil Composition and Method of Making |
| US8158185B2 (en) * | 2007-10-04 | 2012-04-17 | Bunge Oils, Inc. | Controlled viscosity oil composition and method of making |
| NL1036154C (en) * | 2008-11-05 | 2010-05-06 | Criss Cross Technology B V | A motor fuel additive with enhanced properties, and processes for the production thereof. |
| 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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