US3615294A - Detergent motor fuel containing substituted ureas - Google Patents
Detergent motor fuel containing substituted ureas Download PDFInfo
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- US3615294A US3615294A US23027A US3615294DA US3615294A US 3615294 A US3615294 A US 3615294A US 23027 A US23027 A US 23027A US 3615294D A US3615294D A US 3615294DA US 3615294 A US3615294 A US 3615294A
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- Prior art keywords
- motor fuel
- fuel
- urea
- carburetor
- fuel composition
- Prior art date
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- 239000000446 fuel Substances 0.000 title claims abstract description 47
- 150000003672 ureas Chemical class 0.000 title claims abstract description 28
- 235000013877 carbamide Nutrition 0.000 title abstract description 30
- 239000003599 detergent Substances 0.000 title abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000004202 carbamide Substances 0.000 claims description 24
- AWHORBWDEKTQAX-UHFFFAOYSA-N 1,3-dipropylurea Chemical compound CCCNC(=O)NCCC AWHORBWDEKTQAX-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 239000002585 base Substances 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000654 additive Substances 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 12
- -1 hydrocarbyl radical Chemical group 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- MRMOZBOQVYRSEM-UHFFFAOYSA-N tetraethyllead Chemical compound CC[Pb](CC)(CC)CC MRMOZBOQVYRSEM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- YVLLFYIFMKAGCT-KHPPLWFESA-N 1-n-[(z)-octadec-9-enyl]propane-1,2-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCC(C)N YVLLFYIFMKAGCT-KHPPLWFESA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000006079 antiknock agent Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XOOGZRUBTYCLHG-UHFFFAOYSA-N tetramethyllead Chemical compound C[Pb](C)(C)C XOOGZRUBTYCLHG-UHFFFAOYSA-N 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/2227—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond urea; derivatives thereof; urethane
Definitions
- I I I I I I I R--N(CHz)x-NCNICHDr-NR in which x has a value from two to four, R is hydrogen or a hydrocarbyl radical and R and R" are hydrocarbyl radicals having from eight to 20 carbon atoms have been found to be useful as carburetor detergents in a motor fuel composition.
- DETERGENT MOTOR FIUEIL CONTAINING SUESTITUTHED UREAS BACKGROUND OF THE INVENTION Field of the Invention deposits in and around the throttle plate area of the carburetor. These deposits restrict the flow of air through the carburetor at idle and at low speeds so that an overrich fuelmixture results. This condition produces rough engine idling, stalling and also results in excessive hydrocarbon exhaust emissions to the atmosphere.
- US. Pat. No. 2,373,372 discloses alkylated and arylated ureas for improving the antiknock value of gasoline.
- U.S. Pat. No. 2,683,08l discloses N-hydrocarbyLN'-hydroxyphenyl ureas as anti-oxidants for gasoline.
- U.S. Pat. No. 2,772,148 discloses N-alkyl-N',N-di(carboxymethyl) urea as a rust inhibitor for hydrocarbon fuels.
- a class of relatively high molecular weight substituted ureas are provided as carburetor detergents when employed in a liquid hydrocarbonaceous fuel for an internal combustion engine. These ureas are characterized by having a pair of long chain alkylamino alkyl radicals substituted on the basic urea structure and appear to be unique in their detergency properties.
- the fuel composition of the invention mitigates or overcomes the problem of deposits laydown in the carburetor of an internal combustion engine.
- a gasoline of the invention is employed in a carburetor which has a substantial buildup of deposits from prior operations, a severe test of the detergency property of the fuel, this gasoline is very effective for removing substantial amounts of these preformed deposits.
- R is hydrogen or a hydrocarbyl radical having from one to four carbon atoms
- R and R" respectively are hydrocarbyl radicals having from eight to 20 carbon atoms each.
- R is hydrogen .1: has a value of 3,
- R and R" each represent a saturated secondary aliphatic radical having from [0 to 15 carbon atoms.
- the additive of the invention can be prepared by reacting urea with a suitable dihydrocarbon-substituted amine or diamine to produce the noted compound.
- a preferred reaction is to react urea with an Nalkyl-substituted trimethylenediamine.
- two moles of the diamine are reacted with a mole of urea at an elevated temperature to produce the desired product.
- the molar proportion of the reaction the reaction product can be dissolved in a suitable solvent, such as ether-benzene, washed with dilute acidic and basic solutions until the product is slightly basic, dried, and recovered from the solvent by vacuum distillation.
- This reaction is described in Synthesis of Symmetrical Ureas by Heating Urea With a Primary Amine" by J. G. Erickson, .I. Am. Chem. 500., 76, 3977 I954).
- Examples of compounds that are effective carburetor detergents in gasoline include 3,3-di(dodecylamino) di-n-propylurea, 3,3'-di(tetradecylamino) di-n-propylurea, 3,3'-di(octadecylamino) di-n-propylurea, 3-dodecylamino-3'-octadecylamino di-n-propylurea, 2,2'-di(dodecylamino) di-nethylurea, 4,4'-di(hexadecylamino) di-n-butylurea, 3,3- di(sec. C ,H alkylamine) di-n-propylurea and 3,3- di(octadecenylamine) di-n-propylurea.
- the base fuel will consist of a mixture of hydrocarbons in the gasoline boiling range, i.e. from about 75 to 450 F.
- the hydrocarbon components can consist of paraffinic,
- This base fuel will generally have a Research Octane Number above and preferably above 90.
- the substituted urea of the invention can be advantageously employed in the motor fuel at a concentration ranging from about 0.0005 to 0.05 weight percent.
- the preferred concentration ofthe additive is from about 0.001 to 0.0l weight percent.
- the product was washed with water until the wash was slightly basic, i.e. less than pH 8.
- the product was dried over CaSO, and Na sO filtered and the solvent removed by vacuum distillation at 0.5 mm. Hg. ove-ra steam bath.
- N-cocopropylenediamine-urea derivative also known as 3,3'di(cocoamino) di-n-propylurea, had a total Base Number (ASTM D-664) of 167 (Theory 178) and a nitrogen content of 9.3 percent (Theory 8.9).
- Duomeen C is an Armour Company product having the formula R-NH-(Cll h- NH, where R is an alkyl radical derived from coconut fatty acids.
- EXAMPLE II 0.60 moles of N-oleyl propylenediamine (commercial Duomeen 0) and 0.30 moles of urea were reacted as in example I.
- Duomeen 0 is similar in structure to Duomeen C except that the alkyl radical represented by R in the formula above is octadecenyl.
- EXAMPLE V 0.60 moles of N-sec.(C -C alkyl-1,3-propanediamine and 0.30 moles of urea were reacted as in example I.
- the substituted urea had a total base number of 205 (Theory 204) and a nitrogen content of 10.7 (Theory 10.2).
- EXAMPLE VI hydrocarbons, 20 percent olefinic hydrocarbons and 55 percent paraffmic hydrocarbons and boiled in the range from about 90 F. to 360 F.
- the carburetor detergency test results obtained from the base fuel containing the substituted ureas described above are set forth in the following table.
- the additive-containing fuels contained the active detergent additive at a concentration of 5 ptb (pounds per thousand barrels of fuel), a concentration equal to about 0.002 weight percent.
- a minor amount of a light distillate mineral oil carrier introduced in the fuel with the additive has no significant effect on the test results.
- the motor fuel composition of the invention can contain any of the additives normally used in gasoline including corrosion inhibitors, antioxidants, anti-icing TABLE I.- ClIEVROLET (/ARBUREIOR DETERGENCY TEST DEPUSIT REMOVAL Deposit Deposit Percent huildremoved, A Fuel up, mg. 1 mg. tive percent BasofueL. 16.7 6.3 38 Base plus 51TB Example 1 22.5 18.1 80 42 Basefuel.......... 22.2 4.5 20 Base plus 5 PTB Example 11.... 23.6 15.3 65 .Basefuel 21.6 4.!) 23 Base plus 5 PTB Example 111 1 24. 4 20. 7 85 62 Base fuel 18. 5 3.
- a Chevrolet V-8 engine mounted on a test stand using amodified four barrel carburetor.
- the two secondary barrels of the carburetor are sealed and the feed to each of the primary barrels arranged so that an additive fuel can be run in one barrel and a base fuel run in the other.
- the primary carburetor barrels were also modified so that they had removable aluminum inserts in the throttle plate area in order that deposits formed on the inserts in this area could be conveniently weighed.
- the engine In the procedure designed to determine the effectiveness of an additive fuel to remove preformed deposits in the carburetor, the engine is run for a period of time usually 24 or 48 hours using the base fuel as the feed to both barrels with engine blow-by circulated to the air inlet of the carburetor. The weight of the deposits on both sleeves is determined and recorded. The engine is then cycled for 24 additional hours with base fuel being fed to one barrel, additive fuel to the other and no blow-by to the carburetor air inlet. The inserts are then removed from the carburetor and weighed to determine the difference between the performance of the additive and nonadditive fuels in removing the preformed deposits.
- the aluminum inserts are cleaned, they are replaced in the carburetor and the process repeated with the fuels reversed in the carburetor barrels to minimize differences in fuel distribution and barrel construction.
- the deposit weights in the two runs are averaged and the effectiveness of the base fuel and of the additive fuel for removing deposits expressed in percent.
- the base fuel employed in the following examples was a premium grade gasoline having a Research Octane Number of about 101 and containing 3 cc. of tetraethyl lead per gallon.
- This gasoline consisted of about 25 percent aromatic compounds and antiknock agents, such as tetraethyl lead, tetramethyl lead and mixtures thereof.
- a motor fuel composition comprising a mixture of hydrocarbon in the gasoline boiling range and a minor detergent amount of a substituted urea represented by the formula:
- x has a value from 2 to 4
- R is hydrogen or a hydrocarbyl radical having from one to four carbon atoms and R and R respectively are hydrocarbyl radicals having from eight to 20 carbon atoms.
- a motor fuel composition according to claim 1 containing from about 0.0005 to 0.05 weight percent of said substituted urea.
- a motor fuel according to claim 1 in which said substituted urea is 3,3-di(oleylamino)-di-n-propylurea.
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- 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)
- Solid Fuels And Fuel-Associated Substances (AREA)
Abstract
A class of substituted ureas represented by the formula: IN WHICH X HAS A VALUE FROM TWO TO FOUR, R is hydrogen or a hydrocarbyl radical and R'' and R'''' are hydrocarbyl radicals having from eight to 20 carbon atoms have been found to be useful as carburetor detergents in a motor fuel composition.
Description
III I e Inventor Ronald W. Von AlImen Hopewell Junction, NIT. Appl. No. 23,027 Filed Mar. 26, 1970 Patented Oct. 26, 1971 Assignee Texaco Inc.
New York, NY.
DETERGENT MOTOR FUEL CONTAINING [56] References Cited UNITED STATES PATENTS 2,839,372 6/1958 Lindstrom et a] 44/66 3,468,639 9/1969 Lindstrom et al 44/66 Primary Examiner-Daniel E. Wyman Assistant Examiner-W. J. Shine Attorneys-Thomas H. Whaley and Carl G. Ries ABSTRACT: A class of substituted ureas represented by the formula:
I I I I R--N(CHz)x-NCNICHDr-NR in which x has a value from two to four, R is hydrogen or a hydrocarbyl radical and R and R" are hydrocarbyl radicals having from eight to 20 carbon atoms have been found to be useful as carburetor detergents in a motor fuel composition.
DETERGENT MOTOR FIUEIL CONTAINING SUESTITUTHED UREAS BACKGROUND OF THE INVENTION Field of the Invention deposits in and around the throttle plate area of the carburetor. These deposits restrict the flow of air through the carburetor at idle and at low speeds so that an overrich fuelmixture results. This condition produces rough engine idling, stalling and also results in excessive hydrocarbon exhaust emissions to the atmosphere.
DESCRIPTION OF THE PRIOR ART Numerous patents have issued disclosing the use of urea derivatives to effect improvements in gasoline compositions.
US. Pat. No. 2,373,372 discloses alkylated and arylated ureas for improving the antiknock value of gasoline. U.S. Pat. No. 2,683,08l discloses N-hydrocarbyLN'-hydroxyphenyl ureas as anti-oxidants for gasoline. U.S. Pat. No. 2,772,148 discloses N-alkyl-N',N-di(carboxymethyl) urea as a rust inhibitor for hydrocarbon fuels.
SUMMARY OF THE INVENTION A class of relatively high molecular weight substituted ureas are provided as carburetor detergents when employed in a liquid hydrocarbonaceous fuel for an internal combustion engine. These ureas are characterized by having a pair of long chain alkylamino alkyl radicals substituted on the basic urea structure and appear to be unique in their detergency properties.
The fuel composition of the invention mitigates or overcomes the problem of deposits laydown in the carburetor of an internal combustion engine. When a gasoline of the invention is employed in a carburetor which has a substantial buildup of deposits from prior operations, a severe test of the detergency property of the fuel, this gasoline is very effective for removing substantial amounts of these preformed deposits.
DESCRIPTION OF THE PREFERRED EMBODIMENTS The substituted urea additive employed in this invention has the formula:
H O H in which x has the value of from two to four, R is hydrogen or a hydrocarbyl radical having from one to four carbon atoms, and R and R" respectively are hydrocarbyl radicals having from eight to 20 carbon atoms each.
In a preferred embodiment R is hydrogen .1: has a value of 3,
and R and R" each represent a saturated secondary aliphatic radical having from [0 to 15 carbon atoms.
The additive of the invention can be prepared by reacting urea with a suitable dihydrocarbon-substituted amine or diamine to produce the noted compound. A preferred reaction is to react urea with an Nalkyl-substituted trimethylenediamine. In this procedure, two moles of the diamine are reacted with a mole of urea at an elevated temperature to produce the desired product. The molar proportion of the reaction, the reaction product can be dissolved in a suitable solvent, such as ether-benzene, washed with dilute acidic and basic solutions until the product is slightly basic, dried, and recovered from the solvent by vacuum distillation. This reaction is described in Synthesis of Symmetrical Ureas by Heating Urea With a Primary Amine" by J. G. Erickson, .I. Am. Chem. 500., 76, 3977 I954).
Examples of compounds that are effective carburetor detergents in gasoline include 3,3-di(dodecylamino) di-n-propylurea, 3,3'-di(tetradecylamino) di-n-propylurea, 3,3'-di(octadecylamino) di-n-propylurea, 3-dodecylamino-3'-octadecylamino di-n-propylurea, 2,2'-di(dodecylamino) di-nethylurea, 4,4'-di(hexadecylamino) di-n-butylurea, 3,3- di(sec. C ,H alkylamine) di-n-propylurea and 3,3- di(octadecenylamine) di-n-propylurea.
Any gasoline suitable for a spark-ignited, internal combustion engine can be used in the practice of this invention. In general, the base fuel will consist of a mixture of hydrocarbons in the gasoline boiling range, i.e. from about 75 to 450 F.
The hydrocarbon components can consist of paraffinic,
naphthenic, aromatic and olefinic hydrocarbons obtained by thermal or catalytic cracking or reforming of petroleum hydrocarbons. This base fuel will generally have a Research Octane Number above and preferably above 90.
The substituted urea of the invention can be advantageously employed in the motor fuel at a concentration ranging from about 0.0005 to 0.05 weight percent. The preferred concentration ofthe additive is from about 0.001 to 0.0l weight percent.
The following examples illustrate the preparation of the substituted ureas of the invention.
EXAMPLEI 180 g. (0.60 mole) of N-cocoprop ylenediamine (commercial Duomeen C) was placed in a 500 ml. flask equipped with a thermometer, condenser, magnetic stirrer and a sintered glass tube. 18 g. (0.30 mole) of urea was added and themixture heated for 3 hours at I60" C. A slow steady nitrogen flow was maintained to sweep out ammonia being evolved. The nitrogen flow was continued until the reaction product returned to room temperatures. The reaction product was diluted with approximately 600 ml. of ether-benzene and washed alternately with 6Xl00 ml. of 1.5 N hydrochloric acid. After washing with 6Xl00 ml. of 10 percent sodium carbonate, the product was washed with water until the wash was slightly basic, i.e. less than pH 8. The product was dried over CaSO, and Na sO filtered and the solvent removed by vacuum distillation at 0.5 mm. Hg. ove-ra steam bath.
The N-cocopropylenediamine-urea derivative, also known as 3,3'di(cocoamino) di-n-propylurea, had a total Base Number (ASTM D-664) of 167 (Theory 178) and a nitrogen content of 9.3 percent (Theory 8.9). Duomeen C is an Armour Company product having the formula R-NH-(Cll h- NH, where R is an alkyl radical derived from coconut fatty acids.
EXAMPLE II 0.60 moles of N-oleyl propylenediamine (commercial Duomeen 0) and 0.30 moles of urea were reacted as in example I. The substituted urea derivative, 3l,3'di(oleylamino) di-npropylurea, had a total base number of (Theory and a nitrogen content of 7.04 percent (Theory 7.02). Duomeen 0 is similar in structure to Duomeen C except that the alkyl radical represented by R in the formula above is octadecenyl.
EXAMPLE II] 0.60 moles of N-(B-undecyU-l,3-propanediamine (commercial Duomeen L-l 1) and 0.30 moles of urea were reacted as in example I above. The substituted urea derivative had a total base number of I78 (Theory 194) and a nitrogen content of9.9 percent (Theory 9.7
EXAMPLE IV 0.60 moles of N-(B-pentadecyD-l,3-propanediamine (commercial Duomeen L-l) and 0.30 moles of urea were reacted as in example I. The substituted urea derivative had a total base number of 140 (Theory 162) and a nitrogen content of 8.3 percent (Theory 8.1).
EXAMPLE V 0.60 moles of N-sec.(C -C alkyl-1,3-propanediamine and 0.30 moles of urea were reacted as in example I. The substituted urea had a total base number of 205 (Theory 204) and a nitrogen content of 10.7 (Theory 10.2).
EXAMPLE VI hydrocarbons, 20 percent olefinic hydrocarbons and 55 percent paraffmic hydrocarbons and boiled in the range from about 90 F. to 360 F.
The carburetor detergency test results obtained from the base fuel containing the substituted ureas described above are set forth in the following table. The additive-containing fuels contained the active detergent additive at a concentration of 5 ptb (pounds per thousand barrels of fuel), a concentration equal to about 0.002 weight percent. A minor amount of a light distillate mineral oil carrier introduced in the fuel with the additive has no significant effect on the test results.
The foregoing tests, Runs 2, 4, 6, 8 and 10, show that the substituted urea additive of the invention provides a very substantial improvement in the detergent properties of gasoline as compared to the base fuel. These improvements are also in marked contrast to the results obtained with a gasoline containing di-N-sec. (C alkylurea and the ineffectiveness of Run 12 shows that there is criticality in the structure of the substituted urea in order to obtain effective carburetor detergency.
The motor fuel composition of the invention can contain any of the additives normally used in gasoline including corrosion inhibitors, antioxidants, anti-icing TABLE I.- ClIEVROLET (/ARBUREIOR DETERGENCY TEST DEPUSIT REMOVAL Deposit Deposit Percent huildremoved, A Fuel up, mg. 1 mg. tive percent BasofueL. 16.7 6.3 38 Base plus 51TB Example 1 22.5 18.1 80 42 Basefuel.......... 22.2 4.5 20 Base plus 5 PTB Example 11.... 23.6 15.3 65 .Basefuel 21.6 4.!) 23 Base plus 5 PTB Example 111 1 24. 4 20. 7 85 62 Base fuel 18. 5 3. 9 21 Base plus 5 P'IB Example IV, 23.3 14.2 61 40 Base fuel 1 27.1 2 +2.8 -10 Base plus 5 PTB Example V 24. 1 12.6 52 62 Base fuel 17.4 +2.5 14.4 Base plus 5 PTB Example Vl.. 15.5 +2.3 l3.2 1.2
1 Built up with base fuel. 1 Additional deposits formed.
a Chevrolet V-8 engine mounted on a test stand using amodified four barrel carburetor. The two secondary barrels of the carburetor are sealed and the feed to each of the primary barrels arranged so that an additive fuel can be run in one barrel and a base fuel run in the other. The primary carburetor barrels were also modified so that they had removable aluminum inserts in the throttle plate area in order that deposits formed on the inserts in this area could be conveniently weighed.
In the procedure designed to determine the effectiveness of an additive fuel to remove preformed deposits in the carburetor, the engine is run for a period of time usually 24 or 48 hours using the base fuel as the feed to both barrels with engine blow-by circulated to the air inlet of the carburetor. The weight of the deposits on both sleeves is determined and recorded. The engine is then cycled for 24 additional hours with base fuel being fed to one barrel, additive fuel to the other and no blow-by to the carburetor air inlet. The inserts are then removed from the carburetor and weighed to determine the difference between the performance of the additive and nonadditive fuels in removing the preformed deposits. After the aluminum inserts are cleaned, they are replaced in the carburetor and the process repeated with the fuels reversed in the carburetor barrels to minimize differences in fuel distribution and barrel construction. The deposit weights in the two runs are averaged and the effectiveness of the base fuel and of the additive fuel for removing deposits expressed in percent.
The base fuel employed in the following examples was a premium grade gasoline having a Research Octane Number of about 101 and containing 3 cc. of tetraethyl lead per gallon. This gasoline consisted of about 25 percent aromatic compounds and antiknock agents, such as tetraethyl lead, tetramethyl lead and mixtures thereof.
lclaim:
l. A motor fuel composition comprising a mixture of hydrocarbon in the gasoline boiling range and a minor detergent amount of a substituted urea represented by the formula:
in which x has a value from 2 to 4 R is hydrogen or a hydrocarbyl radical having from one to four carbon atoms and R and R respectively are hydrocarbyl radicals having from eight to 20 carbon atoms. g "I w 2. A motor fuel composition according to claim 1 in which x has a value of 3 and R and R are aliphatic hydrocarbon radicals.
3. A motor fuel composition according to claim 1 containing from about 0.0005 to 0.05 weight percent of said substituted urea.
4. A motor fuel composition according to claim 1 m which 1: has a value of 3 and R and R are aliphatic hydrocarbon radicals having from 10-15 carbon atoms.
5. A motor fuel composition according to claim 1 in which said substituted urea is 3.3 '-di(cocoamino) di-n-propylurea.
6. A motor fuel composition according to claim 1 in which said substituted urea is 3,3'-di[sec.(C C, )alkylamino]-din-propylurea.
7. A motor fuel according to claim 1 in which said substituted urea is 3,3-di(oleylamino)-di-n-propylurea.
Claims (6)
- 2. A motor fuel composition according to claim 1 in which x has a value of 3 and R'' and R'''' are aliphatic hydrocarbon radicals.
- 3. A motor fuel composition according to claim 1 containing from about 0.0005 to 0.05 weight percent of said substituted urea.
- 4. A motor fuel composition according to claim 1 in which x has a value of 3 and R'' and R'''' are aliphatic hydrocarbon radicals having from 10-15 carbon atoms.
- 5. A motor fuel composition according to claim 1 in which said substituted urea is 3,3''-di(cocoamino) di-n-propylurea.
- 6. A motor fuel composition according to claim 1 in which said substituted urea is 3,3''-di''(sec.(c10-C15)alkylamino)-di-n-propylurea.
- 7. A motor fuel according to claim 1 in which said substituted urea is 3,3''-di(oleylamino)-di-n-propylurea.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2302770A | 1970-03-26 | 1970-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3615294A true US3615294A (en) | 1971-10-26 |
Family
ID=21812703
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US23027A Expired - Lifetime US3615294A (en) | 1970-03-26 | 1970-03-26 | Detergent motor fuel containing substituted ureas |
Country Status (1)
Country | Link |
---|---|
US (1) | US3615294A (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3919094A (en) * | 1974-09-06 | 1975-11-11 | Phillips Petroleum Co | Additives for lubricants and motor fuels |
US4105417A (en) * | 1974-04-11 | 1978-08-08 | Coon Marvin D | Fuel additive |
FR2436814A1 (en) * | 1977-06-20 | 1980-04-18 | Shell Int Research | COMBUSTIBLE AND LUBRICATING OIL COMPOSITIONS |
US4401439A (en) * | 1981-12-31 | 1983-08-30 | Shell Oil Company | Fuel and lubricant compositions for octane requirement reduction |
US4416669A (en) * | 1982-02-22 | 1983-11-22 | Shell Oil Company | Fuel and lubricant compositions for octane requirement reduction |
US4435187A (en) | 1981-12-31 | 1984-03-06 | Shell Oil Company | Fuel and lubricant compositions for octane requirement reduction |
US5997593A (en) * | 1998-12-22 | 1999-12-07 | Ethyl Corporation | Fuels with enhanced lubricity |
US20040010963A1 (en) * | 2002-07-16 | 2004-01-22 | Betzdearborn, Inc. | Lubricity additives for low sulfur hydrocarbon fuels |
US6971125B2 (en) | 2002-08-02 | 2005-12-06 | Mattson Jr Roy W | Antimicrobial whirlpool bathtub |
US7146659B2 (en) | 2002-08-02 | 2006-12-12 | Mattson Jr Roy W | Hydromassage antimicrobial whirlpool bathtub |
US20150322360A1 (en) * | 2012-12-21 | 2015-11-12 | Total Marketing Services | Gasoline fuel composition, method for the preparation and use of such a composition |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839372A (en) * | 1954-04-09 | 1958-06-17 | California Research Corp | Gasoline composition |
US3468639A (en) * | 1965-08-06 | 1969-09-23 | Chevron Res | Gasolines containing deposit-reducing monoamides of polyamines characterized by improved water tolerance |
-
1970
- 1970-03-26 US US23027A patent/US3615294A/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2839372A (en) * | 1954-04-09 | 1958-06-17 | California Research Corp | Gasoline composition |
US3468639A (en) * | 1965-08-06 | 1969-09-23 | Chevron Res | Gasolines containing deposit-reducing monoamides of polyamines characterized by improved water tolerance |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4105417A (en) * | 1974-04-11 | 1978-08-08 | Coon Marvin D | Fuel additive |
US3919094A (en) * | 1974-09-06 | 1975-11-11 | Phillips Petroleum Co | Additives for lubricants and motor fuels |
FR2436814A1 (en) * | 1977-06-20 | 1980-04-18 | Shell Int Research | COMBUSTIBLE AND LUBRICATING OIL COMPOSITIONS |
US4401439A (en) * | 1981-12-31 | 1983-08-30 | Shell Oil Company | Fuel and lubricant compositions for octane requirement reduction |
US4435187A (en) | 1981-12-31 | 1984-03-06 | Shell Oil Company | Fuel and lubricant compositions for octane requirement reduction |
US4416669A (en) * | 1982-02-22 | 1983-11-22 | Shell Oil Company | Fuel and lubricant compositions for octane requirement reduction |
US5997593A (en) * | 1998-12-22 | 1999-12-07 | Ethyl Corporation | Fuels with enhanced lubricity |
US20040010963A1 (en) * | 2002-07-16 | 2004-01-22 | Betzdearborn, Inc. | Lubricity additives for low sulfur hydrocarbon fuels |
WO2004007648A1 (en) * | 2002-07-16 | 2004-01-22 | Ge Betz, Inc. | Lubricity additives for low sulfur hydrocarbon fuels |
US6872230B2 (en) | 2002-07-16 | 2005-03-29 | Betzdearborn, Inc. | Lubricity additives for low sulfur hydrocarbon fuels |
US20050126073A1 (en) * | 2002-07-16 | 2005-06-16 | Betzdearborn, Inc. | Lubricity additives for low sulfur hydrocarbon fuels |
US6971125B2 (en) | 2002-08-02 | 2005-12-06 | Mattson Jr Roy W | Antimicrobial whirlpool bathtub |
US7146659B2 (en) | 2002-08-02 | 2006-12-12 | Mattson Jr Roy W | Hydromassage antimicrobial whirlpool bathtub |
US7203977B2 (en) | 2002-08-02 | 2007-04-17 | Roy W. Mattson, Jr. | Fill and drain jetted hydromassage antimicrobial water vessel |
US20150322360A1 (en) * | 2012-12-21 | 2015-11-12 | Total Marketing Services | Gasoline fuel composition, method for the preparation and use of such a composition |
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