US2868629A - Motor fuel - Google Patents
Motor fuel Download PDFInfo
- Publication number
- US2868629A US2868629A US621512A US62151256A US2868629A US 2868629 A US2868629 A US 2868629A US 621512 A US621512 A US 621512A US 62151256 A US62151256 A US 62151256A US 2868629 A US2868629 A US 2868629A
- Authority
- US
- United States
- Prior art keywords
- motor fuel
- acid
- glycoside
- ester
- deposits
- 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
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- 239000000446 fuel Substances 0.000 title claims description 29
- 229930182470 glycoside Natural products 0.000 claims description 20
- 150000002338 glycosides Chemical class 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 description 20
- -1 alkylaryl glycosides Chemical class 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 description 9
- 230000006698 induction Effects 0.000 description 9
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000002485 combustion reaction Methods 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229930182478 glucoside Natural products 0.000 description 7
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 150000008131 glucosides Chemical class 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 125000005608 naphthenic acid group Chemical group 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- KNMJLCQPUBMARM-UHFFFAOYSA-N 2,2,6-trimethylcyclohexane-1-carboxylic acid Chemical compound CC1CCCC(C)(C)C1C(O)=O KNMJLCQPUBMARM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- QKBSRWIVHXFMNA-OEKLXEDWSA-N Decoside Chemical class O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C[C@@H](CC[C@H]2[C@]3(CC[C@@H]([C@@]3(C)C(=O)C(O)=C32)C=2COC(=O)C=2)O)[C@]3(C)CC1 QKBSRWIVHXFMNA-OEKLXEDWSA-N 0.000 description 1
- VWVNEVMJJOFEPL-UHFFFAOYSA-N Decoside Natural products COC1CC(OC2CCC3(C)C(CCC4C3C(=O)C(=O)C5(C)C(CCC45O)C6=CC(=O)OC6)C2)OC(C)C1O VWVNEVMJJOFEPL-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 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
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004231 fluid catalytic cracking Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229940049918 linoleate Drugs 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical group C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 150000005691 triesters 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
- 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 motor fuels and particularly motor fuels for use in spark-ignited, internal combustion engines.
- the invention is more particularly concerned with motor fuels containing a small amount of additive to mitigate the formation of deposits in the induction systems of automotive engines and to the methodfor inhibiting formation of such deposits.
- An object of the invention is to provide an additive which when added to leaded motor fuel will lessen the tendency of the motor fuel to form deposits in the induction systems of internal combustion engines.
- Another object of the invention is to provide a leaded motor fuel which Will not form deposits or which forms only small amounts of deposits in the induction system of an automotive engine of the internal combustion type.
- a further. object of the invention is to provide a method for mitigating deposition in the induction system of internal combustion engines.
- glycoside esters of the type hereinbefore described in an amount between about 0.005 and by weight, induction system deposits can be eliminated or greatly reduced.
- the additive in the amount of about 0.01% by weight is effective for this purpose. This corresponds to about 35 pounds of glycoside ester per 1000 barrels of gasoline or similar motor fuel.
- glycosides useful in preparing the esters of our invention are represented by. the formula HOOH2CH(CHOH)2CHOR in which R is an alkyl or alkylaryl radical containing 1 to 12 carbon atoms and x is an integer of 1-8.
- R is an alkyl or alkylaryl radical containing 1 to 12 carbon atoms and x is an integer of 1-8.
- These glycosides are esterified with 1 to 4 molecules of a monocarboxylic acid, such as fatty acids, aromatic acids and naphthenic acids, containing 8 to 24 carbon atoms per molecule.
- Mono, di, tri and' tetraesters of the glycosides are useful.
- the effectiveness of the additive in reducing deposit formation is dependent on the chain length of the esterifying acid and on the number of acid groups in the molecule.
- R is an alkyl or alkaryl radical containing 1-12 carbon atoms and R is an aliphatic chain containing 7-23 carbon atoms.
- compounds in this group are the mono-caprylate of methyl hexoside, mono-caprylate of lauryl hexoside, mono-caprylate of ethyl phenyl hexoside and the monocaprylate of propyl, butyl, amyl, hexyl, octyl, nonyl, decyl, and hexyl phenyl hexoside.
- ther examples are the mono-laurate, mono-palmitate, mono-stearate and mono-linoleate of the foregoing hexosides.
- R is (CH R 'is C 'H and R is hydrogen
- the compound is the monooleateof methyl tetroside.
- esters such as the monooleate ester of ethyl octoside
- decoside esters such as the monooleate of ethyl decoside.
- the esters may contain one to four acid radicals and various alkyl and alkylaryl radicals can be substituted for the ethyl radical.
- gasoline made by fluid catalytic cracking of petroleum oil was mixed with pounds of each of the glycoside esters listed in the following table, per 1000 barrels of gasoline.
- the gasoline used in these tests had the following characteristics:
- test run was conducted in a one-cylinder Lawson engine and the run lasted for a period of 12 hours.
- glycoside ester when the acid radical is longer or more acid groups are attached to the glycoside than in the case where the acid radical is shorter or contains a lesser number of acid groups.
- the glycoside appears to be the active constituent of the ester in reducing deposits.
- the esterifying acid merely serves to solubilize the glycoside in the motor fuel.
- fatty acids are used to esterify the glycoside, it will be understood that other acids, such as the aromatic and naphthenic acids having a sufficient number of carbon atoms to solubilize the resulting ester, can be used, such as toluic acid, cinnamic acid, phenyl propionic acid, and 2,2,6-trimethylcyclohexanecarboxylic acid.
- a hydrocarbon motor fuel of the gasoline boiling range containing about 0.005 to 5.0 wt. of esterified glycoside, said glycoside corresponding to the formula noonzontononnon in which x is 1-8, R is from the group consisting of alkyl and alkylaryl radicals containing 1 to 12 carbon atoms, and the glycoside is esterified with one to four molecules of a monobasic aliphatic acid containing from 8 to 24 carbon atoms per molecule.
- ester is the monocaprylate of lauryl hexoside.
- a motor fuel in accordance with claim 5 inwhich 5' the ester is the trioleate of methyl glucoside present in the amount of about .01% by weight.
Description
nited Crystal Lake, lil., assignors to The Pure Oil Company, Chicago, 1111., a corporation of Ohio No Drawing. Application November 13', 1956 Serial No; 621,512 t 12 Claims. CI. 44-66) This invention relates to motor fuels and particularly motor fuels for use in spark-ignited, internal combustion engines. The invention is more particularly concerned with motor fuels containing a small amount of additive to mitigate the formation of deposits in the induction systems of automotive engines and to the methodfor inhibiting formation of such deposits.
Motor fuels containing tetraethyl lead have a tendency to deposit solid material in the induction system; that is, the area between the carburetor and combustion chamber 01' internal combustion engines, which interferes with the efi'icient operation of the engine. We have discovered that induction system deposits can be greatly mitigated by adding to the motor fuel or gasoline small amounts of certain types of additives.
An object of the invention is to provide an additive which when added to leaded motor fuel will lessen the tendency of the motor fuel to form deposits in the induction systems of internal combustion engines.
Another object of the invention is to provide a leaded motor fuel which Will not form deposits or which forms only small amounts of deposits in the induction system of an automotive engine of the internal combustion type.
A further. object of the invention is to provide a method for mitigating deposition in the induction system of internal combustion engines.
Other objects of the invention will make themselves manifest from the following detailed description of the invention.
We have discovered that partially esterified alkyl and alkylaryl glycosides when added to leaded motor fuel greatly mitigate the tendency of such fuels to form deposits in the induction system of spark ignition type internal combustion engines. These deposits tend to form in the area between the carburetor and the combustion chamber of the engine, particularly in the intake manifold and on the valves, causing constriction of the intake manifold and preventing proper closing of the valves, with resultant burning thereof. This tendency to form deposits is aggravated in connection with the use of modern fuels containing in addition to saturated hydrocarbons, unsaturated and aromatic hydrocarbons and tetraethyl lead.
We have found that by adding to such motor fuels glycoside esters of the type hereinbefore described in an amount between about 0.005 and by weight, induction system deposits can be eliminated or greatly reduced. We have found that the additive in the amount of about 0.01% by weight is effective for this purpose. This corresponds to about 35 pounds of glycoside ester per 1000 barrels of gasoline or similar motor fuel.
f tates Patent Patented Jan. 13, 1 959 2 v The glycosides useful in preparing the esters of our invention are represented by. the formula HOOH2CH(CHOH)2CHOR in which R is an alkyl or alkylaryl radical containing 1 to 12 carbon atoms and x is an integer of 1-8. These glycosides are esterified with 1 to 4 molecules of a monocarboxylic acid, such as fatty acids, aromatic acids and naphthenic acids, containing 8 to 24 carbon atoms per molecule. Mono, di, tri and' tetraesters of the glycosides are useful. However, the effectiveness of the additive in reducing deposit formation is dependent on the chain length of the esterifying acid and on the number of acid groups in the molecule. Shorter chains and less complete esterificatio'n produce esters which are more effective than those in which acids of longer chain lengths are used or more acid groups are attached to the glycoside by esterificat ion. the glycoside soluble in the gasoline in the amount in which it is added, a sufficient number of acidic groups or acidic groups of long enough chain length must be attached to the glycoside to make it soluble. The following groups of compounds and specific examples under each group are useful as additives for the purpose of our invention:
1. Hexoside mono esters in which R is an alkyl or alkaryl radical containing 1-12 carbon atoms and R is an aliphatic chain containing 7-23 carbon atoms.
Specific examples of compounds in this group are the mono-caprylate of methyl hexoside, mono-caprylate of lauryl hexoside, mono-caprylate of ethyl phenyl hexoside and the monocaprylate of propyl, butyl, amyl, hexyl, octyl, nonyl, decyl, and hexyl phenyl hexoside. ther examples are the mono-laurate, mono-palmitate, mono-stearate and mono-linoleate of the foregoing hexosides.
II. Di, tri and tetra esters of alkyl and alkylaryl hexosides However, since it is necessary to make in which R, R and R are defined the same as in II.
As a specific example where R is (CH R 'is C 'H and R is hydrogen, the compound is the monooleateof methyl tetroside. It will be apparent that any of the R groups under I can be substituted for R in Formula 111 and any fatty acid given under I can be substituted for oleic acid to give a corresponding tetroside ester;
IV. Pentoside esters I in which R, R and R are defined the same as in II.
Specific examples are trioleate of methyl pentoside and the mono and diesters of palmitic, stearic and linoleic acids in which the R group can be ethyl, ethyl phenyl or any of the specific alkyl or alkylaryl groups mentioned under II.
V. Other examples are the octoside esters such as the monooleate ester of ethyl octoside, and decoside esters such as the monooleate of ethyl decoside. As in the previous groups, the esters may contain one to four acid radicals and various alkyl and alkylaryl radicals can be substituted for the ethyl radical.
In order to demonstrate the invention, gasoline made by fluid catalytic cracking of petroleum oil was mixed with pounds of each of the glycoside esters listed in the following table, per 1000 barrels of gasoline. The gasoline used in these tests had the following characteristics:
Tetraethyl lead 3 cc./gal.
Each test run was conducted in a one-cylinder Lawson engine and the run lasted for a period of 12 hours.
Table I Percent Re- Run N0. Additive duction in Deposits none- (0.0894 gram) methyl glucoside trilaurate 78 methyl glucoside tetralaurate 52 methyl glucoside trioleate 49 methyl glucoside tetraoleate 39 Run A was made on the motor fuel without any glucoside ester added thereto to determine the magnitude of the deposit as a basis of comparison for the subsequent runs made with addition of the glucoside esters. Run B, in which the methyl glucoside trilaurate was used, produced the largest reduction in deposits. By comparing runs B, C, D and E, it will be seen that the glucoside which contained the shortest acid chain (laurate) and the glucoside which contained the fewest number of acid groups (trilaurate) gave the largest reduction in deposits. Similarly, the ester containing the longest and greatest number of acid groups (tetraoleate) gave the lowest reduction in deposits. All of the glucoside esters tested, however, gave a significant reduction in induction system deposits.
It will be apparent that to get the same effectiveness in deposit reduction it is neecssary to use a larger amount of glycoside ester when the acid radical is longer or more acid groups are attached to the glycoside than in the case where the acid radical is shorter or contains a lesser number of acid groups. The glycoside appears to be the active constituent of the ester in reducing deposits. The esterifying acid merely serves to solubilize the glycoside in the motor fuel.
Although in the specific examples fatty acids are used to esterify the glycoside, it will be understood that other acids, such as the aromatic and naphthenic acids having a sufficient number of carbon atoms to solubilize the resulting ester, can be used, such as toluic acid, cinnamic acid, phenyl propionic acid, and 2,2,6-trimethylcyclohexanecarboxylic acid.
We claim as our invention:
1. A hydrocarbon motor fuel of the gasoline boiling range containing about 0.005 to 5.0 wt. of esterified glycoside, said glycoside corresponding to the formula noonzontononnonon in which x is 1-8, R is from the group consisting of alkyl and alkylaryl radicals containing 1 to 12 carbon atoms, and the glycoside is esterified with one to four molecules of a monobasic aliphatic acid containing from 8 to 24 carbon atoms per molecule.
2. A motor fuel in accordance with claim 1 in which R is an alkyl group.
3. A motor fuel in accordance with claim 1 in which R is an alkylaryl group.
4. A motor fuel in accordance with claim 1 in which the esterified glucoside is a monoester of a fatty acid.
5. A motor fuel in accordance with claim 1 in which the ester is a triester present in the amount of about .005 to 5% by weight. I I
6. A motor fuel in accordance with claim 1 in which the ester is a tetraester.
7. A motor fuel in accordance with claim 4 in which the esterified glucoside is the monocaprylate.
8. A motor fuel in accordance with claim 4 in which the ester is the monocaprylate of lauryl hexoside.
9'. A motor fuel in accordance with claim 5 in which the ester is the trilaurate ester of methyl glucoside present in the amount of about .01%. i
10, A motor fuel in accordance with claim 5 inwhich 5' the ester is the trioleate of methyl glucoside present in the amount of about .01% by weight.
11. A motor fuel in accordance with-claim 6 in which the ester is the tetralaurate of methyl glucoside present in the amount of .01% by weight.
12. A motor fuel in accordance with claim 6 in which the ester is the tetraoleate of methyl glucoside present in the amount of .0l% by weight.
References Cited in the file of this patent UNITED STATES PATENTS FOREIGN PATENTS Great Britain May 30, 1956
Claims (1)
1. A HYDROCARBON MOTOR FUEL OF THE GASOLINE BOILING RANGE CONTAINING ABOUT 0.005 TO 5.0 WT. % OF ESTERIFIED GLYCOSIDE, SAID GLYCOSIDE CORRESPONDING TO THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US621512A US2868629A (en) | 1956-11-13 | 1956-11-13 | Motor fuel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US621512A US2868629A (en) | 1956-11-13 | 1956-11-13 | Motor fuel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2868629A true US2868629A (en) | 1959-01-13 |
Family
ID=24490470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US621512A Expired - Lifetime US2868629A (en) | 1956-11-13 | 1956-11-13 | Motor fuel |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2868629A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992082A (en) * | 1958-06-24 | 1961-07-11 | Eastman Kodak Co | Anti-sludging hydrocarbon fuel oils |
| US3219582A (en) * | 1961-02-27 | 1965-11-23 | Monsanto Co | Lubricants and fuels containing saccharide polydicarboxylate half-esters |
| EP0948586A1 (en) * | 1996-09-13 | 1999-10-13 | Exxon Research And Engineering Company | Polyol ester fuels additive |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2236590A (en) * | 1938-10-31 | 1941-04-01 | Pure Oil Co | Material for improved engine operation |
| US2289006A (en) * | 1940-12-23 | 1942-07-07 | Dow Chemical Co | Method of protecting light-metal surfaces |
| US2548347A (en) * | 1948-07-06 | 1951-04-10 | Shell Dev | Fuel oil composition |
| GB749505A (en) * | 1951-08-30 | 1956-05-30 | Autol Ag | Additives for motor fuels |
-
1956
- 1956-11-13 US US621512A patent/US2868629A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2236590A (en) * | 1938-10-31 | 1941-04-01 | Pure Oil Co | Material for improved engine operation |
| US2289006A (en) * | 1940-12-23 | 1942-07-07 | Dow Chemical Co | Method of protecting light-metal surfaces |
| US2548347A (en) * | 1948-07-06 | 1951-04-10 | Shell Dev | Fuel oil composition |
| GB749505A (en) * | 1951-08-30 | 1956-05-30 | Autol Ag | Additives for motor fuels |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2992082A (en) * | 1958-06-24 | 1961-07-11 | Eastman Kodak Co | Anti-sludging hydrocarbon fuel oils |
| US3219582A (en) * | 1961-02-27 | 1965-11-23 | Monsanto Co | Lubricants and fuels containing saccharide polydicarboxylate half-esters |
| EP0948586A1 (en) * | 1996-09-13 | 1999-10-13 | Exxon Research And Engineering Company | Polyol ester fuels additive |
| EP0948586A4 (en) * | 1996-09-13 | 2000-02-23 | Exxon Research Engineering Co | Polyol ester fuels additive |
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