US3711255A

US3711255A - Motor fuel composition

Info

Publication number: US3711255A
Application number: US00101408A
Authority: US
Inventors: D Lachowicz; G Saines; G Eckert
Original assignee: Texaco Inc
Current assignee: Texaco Inc
Priority date: 1970-12-24
Filing date: 1970-12-24
Publication date: 1973-01-16
Anticipated expiration: 1990-01-16

Abstract

MOTOR FUEL COMPOSITION COMPRISING A MIXTURE OF HYDROCARBONS IN THE GASOLINE BOILING RANGE CONTAINING A NITROKETONIZED AMIDE CORRESPONDING TO THE FORMULA:

R-N(-R'')-(CH2)3-NH-R"

WHERE R, R'' OR R" IS A NITRODETONIZED GROUP HAVING FROM 4 TO 40 CARBON ATOMS. THE NITROKETONIZED AMIDE PROVIDES THE FUEL COMPOSITION WITH SUCH PROPERTIES AS RUST PROTECTION, CARBURETOR DE-ICING AND CARBURETOR DETERGENCY.

Description

United States Patent "ice 3,711,255 MGTQR FUEL COMPOSITION Donald R. Lachoviicz and George S. Saines, Fishkill, and George W. Eclrert, Wappingers Falls, N.Y., assignors to Texaco Inc., New York, N.Y. No Drawing. Filed Dec. 24, 1970, Ser. No. 101,408 Int. Cl. (11011/18, 1/22 US. Cl. 44-66 Claims ABSTRACT 0F THE DESCLDSURE Motor fuel composition comprising a mixture of hydrocarbons in the gasoline boiling range containing a nitroketonized amide corresponding to the formula:

RNCHzCH2CH2-N-H I RI! Where R, R or R" is a nitroketonized group having from 4 to 40 carbon atoms. The nitroketonized amide provides the fuel composition with such properties as rust protection, carburetor de-icing and carburetor detergency.

BACKGROUND on THE INVENTION This invention relates to an improved motor fuel composition for internal combustion engines. More particularly, the invention involves the discovery that the incorporation of a minor amount of a nitroketonized amide into gasoline produces a fuel having improved carburetor detergent properties along with good corrosion inhibiting and anti-icing properties.

Modern internal combustion engine design is undergoing significant changes to meet higher standards concerning engine and exhaust gas emissions. A major change in engine design presently being widely adopted is the feeding of crankcase blow-by gases of the engine into the intake air supply to the carburetor rather than venting to the atmosphere as was done in the past. Blow-by gases, however, contain substantial amounts of deposit-forming substances and it has been observed that some of the constituents in the blow-by gas form deposits in and around the throttle plate area of the carburetor. Such deposits restrict the flow of air through the carburetor at idle and low speeds resulting in an overrich fuel mixture. Such a condition produces rough idling, engine stalling and also results in excessive hydrocarbon exhaust emissions to the atmosphere. In addition to overcoming the foregoing problem, a competitive modern gasoline must provide a high degree of corrosion inhibiting and anti-icing properties.

A novel fuel composition has been discovered which mitigates or overcomes the problem of deposit laydown in the carburetor of an internal combustion engine. More specifically, a motor fuel composition containing a novel additive has been found which is effective for substantially reducing the laydown of deposits in a carburetor. The additive also provides excellent corrosion inhibiting and anti-icing properties in the gasoline.

Broadly, this invention contemplates a motor fuel composition comprising a mixture of hydrocarbons in the gasoline boiling range and a minor amount of a nitroketonized amide corresponding to the formula:

R-NCH.-CHaCH:N-H

g RI! where R is an alkyl, alkenyl, nitroketonized alkyl or nitroketonized alkenyl group, where R and R alternately represent hydrogen and an alkanoyl, alkenoyl, nitroketonized alkanoyl or nitroketonized alkenoyl group, wherein at least one of said R, R or R" is a nitroketonized group as heretofore defined. In particular, R when alkyl 3,711,255 Patented Jan. 16, 1973 represents a group having from 1 to 40, preferably 8 to 22, carbon atoms and when alkenyl, nitroketonized alkyl or nitroketonized alkenyl represents a group having from 4 to 40, preferably 8 to 22, carbon atoms. Further, R and R" when alternately representing a group recited above, other than hydrogen, contains from 4 to 40, preferably 8 to 22, carbon atoms.

The nitroketonized amides employed in this invention are prepared by contacting the precursor, namely an acid amide, of the formula:

where R is an alkyl group having from 1 to 40 carbon atoms or alkenyl group having from 4 to 40 carbon atoms, where R and R alternately represent hydrogen and an alkanoyl group or an alkenoyl group having from 4 to 40 carbon atoms, wherein at least one of said R R or R is an alkenyl or an alkenoyl group, with dinitrogen tetroxide and oxygen at a temperature of from about 35 to 45 C. in a mole ratio of said acid amide to dinitrogen tetroxide to oxygen of from 111:1 and 1:4:60. In a desirable embodiment R and R or R are respectively alkenyl and alkenoyl groups having from 4 to 40, preferably 8 to 22, carbon atoms and where the mole ratio of acid amide to dinitrogen tetroxide to oxygen is from 1:2:2 to 1:4:60. Preferably, the reaction is conducted at temperatures of from 10 to -30 C. and R R or R represent groups having from 8 to 22 carbon atoms.

Nitroketonization of the aforementioned acid amide can be accomplished in a one-step reaction as contrasted to other known processes where olefins are initially converted to intermediate nitroperoxy compounds and where the intermediate compound is subsequently contacted with a denitrating agent to yield a nitroketone product. Here, the introduction of a denitrating agent is not essential inasmuch as autogenous conversion at the point of unsaturation directly results in vicinal nitroketonization.

The acid amide containing at least one group identified as R R or R possessing at least one unsaturated group along a carbon chain is converted in the course of nitroketonization to a vicinal nitroketone function For example, unsaturation of the acid amide may be in R as an alkenyl group such as 3-buteny1, 2-pentenyl, IO-undecenyl, 9-octadecenyl and l3-docosenyl. Alternatively R may be an alkyl group such as methyl, ethyl, butyl, hexyl, dodecyl, hexadecyl and tetracosanyl. When R is alkyl, unsaturation of the acid amide occurs at R or R as an alkenoyl group such as 2-methyl-3-butenoyl, 3-butenoyl, IO-undecenoyl, S-hexadecenoyl, 9-octadenenoyl and 13-docosenoyl. Alternatively when R or R is alkanoyl, such as isobutanoyl, heptanoyl, decanoyl, pentadecanoyl and tetracosanoyl, R is an alkenyl group. Forther, unsaturation may occur in a plurality of points along R R or R Moreover, unsaturation at one or more points may occur simultaneously in R and R or R as when R is 9-octadecenyl and R or R is lO-undecenoyl. Depending on the ratio of acid amide to dinitrogen tetroxide to oxygen, acid amides having a plurality of unsaturated linkages can to varying degrees be singularly to totally converted to vicinal nitr'oketone groups. Where a plurality of unsaturation occurs and it is contemplated that some or all be converted to vicinal nitroketone groups the lower ratios of acid amide to dinitrogen tetroxide to oxygen of 1:2:2 to 1:4:60 are employed along with a denitrating agent introduced to the reaction product re- 3 sulting from contacting of the acid amide, dinitrogen tetroxide and oxygen.

The denitrating agent is added to the reaction product in a mole ratio of agent to product of at least 1:1 and preferably less than about 20:1 at a temperature about 35 to 45 C. Specific examples of denitrating agents include dimethylformamide, diethylformamide, dimethylacetamide, dirnethylsulfoxide, diethylsulfoxide, tetramethylurea and tetraethylurea.

When unsaturation of R R or R occurs internally, that is, on other than a terminal carbon atom, the reaction yields a mixture of two isomeric vicinal nitroketonized amides, illustratively, N-(9-nitro-10-octadecanonyl)-N'- octadecanoyl-l,3-diaminopropane and N-(10-nitro-9-octadecanonyl)-N-octadecanoyl-1,3-diaminopropane. When unsaturation occurs between the terminal and adjacent carbon atom, nitration occurs on the terminal carbon and ketonization on the carbon vicinal thereto as for example N-decyl-N-(4nitro-3-butanonyl)-l,3-diaminoproane.

p The unsaturated acid amide employed as a starting reactant is prepared from readily available materials. Essentially, such an acid amide is provided byreacting primary amine with acrylonitrile to yield the corresponding N-(Z-cyanoethyl)-N-alkylamine and subsequently selectively hydrogenating the cyano group to the N-hydrocarbyl-1,3-diaminopropane (a diamine) where the hydrocarbyl radical is 'alkyl or alkenyl. Subsequently, the N- hydrocarbyl-1,3-diaminopropane is reacted with a C to C alkanoic or alkenoic acid to form an ammonium salt of the acid which upon heating in the absence of added water is converted to the acid amide. With regard to the alkenyl or alkenoyl group, each may have one or more points of unsaturation that subsequently undergo nitroketonization according to the process herein described. For example, polyunsaturated acids as those occurring in whale oil, fish oil, corn oil, linseed oil and other oils can be employed including 9,12-octadecadienoic acid and 9,12, -octadecatrienoic acid.

In the course of nitroketonization of the acid amide, air can be employed as the source of oxygen or oxygen can be provided in admixture with inert gases such as nitrogen or argon. Under preferred conditions, oxygen and dinitrogen tetroxide are respectively introduced into the reaction zone containing the amide at a rate of between 1 and 16 milliliters per minute of oxygen per gram of amide and between about 0.005 and 0.05 gram of dinitrogen tetroxide per minute per gram of amide. Atmospheric and higher pressures may be employed and the reaction is conveniently conducted in the presence of inert organic solvents having from 4 to 22 carbon atoms exemplified by hydrocarbons including paraflins such as pentane, hexane, octane, decane, dodecane, octadecane; cycloparafiins such as cyclopentane and cyclohexane; and aromatic hydrocarbons such as benzene and toluene. In general, reaction times of about one-half to ten hours are employed, the time related to the rate of addition of the dinitrogen tetroxide.

It is to be noted that the dinitrogen tetroxide employed is actually an equilibrium mixture of dinitrogen tetroxide and nitrogen dioxide with the equilibrium being driven to essentially 100 percent dinitrogen tetroxide at 0 C. and essentially 100 percent nitrogen dioxide at 140 C. at 1 atmosphere pressure.

Nitroketonized amides contemplated as motor fuel additives herein include by way of illustration and not limitation N-hexy1-N'- (9'-nitro-10-0ctadecanonoyl) -1,3-diaminopropane,

N-hexyl-N'- 10-nitro-9-octade-canonoyl) -1,3-diaminopropane,

N-hexyl-N-(9-nitro-lO-octadecanonoyl)-1,3-diaminopropane,

N-hexyl-N-( 1 0-.nitro-9-octadecanonoyl) 1, 3-diaminopropane,

N-(9"-n'itro-10-octadecanonyl)-N'-heptanoyl-1,3-diaminopropane,

N- 10-nitro-9-octadecanonyl)-N' heptanoyl-1,3-diaminopropane,

N-( 13-nitro-l4-docosanonyl)-N' (8-hexadecenoyl)- 1,3 -diaminopropane,

N-( l4-nitro- 13 -docosanonyl N- (-8-hexadecenoyl) 1,3-diaminoprop ane,

N-( l 3-docosenyl) -N'- 8-nitro-9-hexadecanonoyl) -1,3-

diaminopropane,

N- 13-docosenyl) -N(9-nitro-8-hexadecanonoyl) -1,3-

diaminopropane,

N- l3-nitro-14-docosanonyl)-N-(8-nitro-9-hexadecanonoyl)-1,3-diaminopropane,

N-( 14-nitrol 3-docosanonoyl) -N- 8-nitro-9-hexadecanonoyl 1 ,3-diaminopropane,

N-( l0-nitro-9-octadecanonyl) -N'--( 9-octadecenoyl 1,3-diaminopropane,

N(10-nitro-9-octadecanonyl)-N'-octanoyl-1,3-diaminopropane,

N- (Cg-C1 alkyl-N-( 10-nitro-9-octadecanonoyl) 1, 3-diaminopropane,

N-( 10-nitro-9-octadecanonyl) -N' l0-nitro-9-octadecanonoyl) -1,3 -diaminopropane, and

N-(9-nitro-10-octadecanonyl)-N-(9-nitro10-octadecanonoyl) 1 ,3-diaminoprop ane.

In general, effective detergent motor fuels are produced by adding from about 0.0001 to 0.1 weight percent of the nitroketonized amide to the gasoline. A preferred concentration of the nitroketonized amide is in the range from about 0.001 to 0.02 weight percent which corresponds to about 3 to 60 p.t.b. (pounds of additive per 1000 barrels of fuel).

The carburetor detergency eifect of the additive and motor fuels containing the same was determined in a specially developed engine test designated the Chevrolet V8 Carburetor Detergency Test. This test was conducted using a Chevrolet V8 engine equipped with a 4- barrel carburetor mounted on a test stand. The two secondary barrels of the carburetor were sealed and each of the primary barrels arranged so that an additive fuel could be run in onebarrel and a base fuel run in the other. The primary carburetor barrels were modified to the extent that they had removable aluminum inserts in the throttle plate area so that deposits formed in this area could be conveniently weighed.

In the test designed to determine the effectiveness of the detergent-containing fuel for preventing the lay-down of deposits, the engine is run for a period of 24 to 48 hours with the base fuel being fed to one barrel and the additive fuel to the other barrel while engine blow-by is circulated to the air inlet of the carburetor. After the run, the inserts are removed from the carburetor and weighed to determine the difference between the performance of the additive and non-additive fuels. The aluminum inserts are then cleaned, 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 detergency effectiveness of the additive fuel expressed in percent.

The anti-icing properties of the additive-containing fuel of the invention was determined in a carburetor icing demonstrator apparatus consisting of a vacuum pump equipped so that cool moisture-saturated air from an ice tower is drawn through a sample glass tube gasoline carburetor. The gasoline sample is placed in a sample bottle and is drawn into the glass carburetor through a 20 gage hypodermic needle. Evaporation of the gasoline in the gas tube further cools the cold moist air with resulting ice for mation on the throttle plate. The formation of ice on the throttle plate causes an engine to stall and it has been found that this condition is equivalent to a pressure drop across the throttle plate of about 0.5 inch and 0.9 inch of mercury and the time required to reach this pressure drop is noted. The vacuum. pump is adjusted to give a vacuum of 1.8 inches of mercury and the test is run until either a pressure of 2.3 inches mercury has been reached or the 5 run has continued for 300 seconds. Since, with most fuels, this pressure drop is reached in l to 4 minutes 300 seconds is the maximum time for a run. A fuel composition which provides a minimum of 200 seconds run in this test is an effective carburetor anti-icing fuel composition.

The anti-rusting propertiesof motor fuels was determined by inserting and thoroughly wetting a cold-rolled steel strip into a tall form four ounce glass bottle containing 90 cc. of the fuel sample and adding 20 cc. of distilled water. The bottle was stoppered, agitated for 15 seconds and stored at room temperature for 24 hours. The strip was thereafter visually inspected and the percentage of rusted surface area estimated.

In order to more fully illustrate the nature of this invention and manner of practicing the same, the following examples are presented.

EXAMPLE I To a solution of 14.7 grams (0.025 mole) of a mixture of N-(9-octadecenyl)-N'-(9-octadecenoyl) 1,3 diaminopropane and N- (9-octadecenyl) -N-(9-octadecenoyl) -1,3- diaminopropane in 200 ml. of n-hexane as inert solvent, there was added simultaneously oxygen at a rate of 60.8 milliliters per minute and dinitrogen tetroxide at the rate of 0.0081 mole per hour for 3.1 hours at C. After 3.1 hours, 1.5 milliliters of liquid dinitrogen tetroxide (0.025 mole) had been transferred to the reaction flask and the solution was purged with oxygen for about 1 hour. The reaction mixture was washed with 150 ml. of 3.3% aqueous sodium bicarbonate and twice with 100 milliliters of water and dried over sodium sulfate. Sodium sulfate was subsequently removed by filtration and the n-hexane was stripped by rotary evaporation leaving a product residue of 10.8 grams. Infrared spectroscopic analysis of the product obtained after nitrooxidation showed the presence of a carbonyl function and the absence of a peroxynitrate function and the product was identified as a mixture of nitroketotnized amides including N- 10-nitro9-octadecanonyl) -N- 9-octadecenoyl) 1,3-diaminopropane,

N-( 10-nitro-9-octadecanonyl) -N (9-octadecenoyl)- 1,3-diaminopropane,

N 9-nitro- 10-octadecanonyl) -N- 9-octadecenoyl) 1,3-diaminopropane,

N- (9-nitro-10-octadecanonyl)-N-(9-octadecenoyl)- 1,3-diaminopropane,

N-(9-octadecenyl)-N'-(10-nitro-9-octadecanonoyl)- 1,3-diaminopropane,

N- (9-octadecenyl -N( l0-nitro-9-octadecanonoyl) 1,3-diaminopropane, 05

N-(9-octadecenyl) -N'-(9-nitro-10-octadecanonoyl)- 1,3-diaminopropane and N-(9-octadecenyl) -N- (9-nitro-10-octadecanonoyl)- 1,3-diaminopropane.

EXAMPLE II Example I was repeated employing 14.7 grams (0.025 mole) of the mixed acid amide with 200 ml. of toluene as the inert solvent and simultaneously contacting the solution with oxygen introduced at the rate of 60.8 milliliters per minute and dinitrogen tetroxide at the rate of 0.086 mole per minute for 2.9 hours. A product yield of 12.0 grams was obtained and identified as a mixture of nitroketonized amides as in Example I.

EXAMPLE III To a solution of 25.5 grams (0.05 mole) of N-(9-octadecenyl)-N-octanoyl 1,3 diaminopropane in 300 milliliters of n-pentane as inert solvent, there was added simultaneously oxygen at the rate of 60.8 milliliters per 6 minute and dinitrogen tetroxide at the rate of 0.018 mole per hour for 2.75 hours at 0 C. After 2.75 hours 3.1 ml. of liquid dinitrogen tetroxide (0.05 mole) had been transferred to the reaction flask and the solution was purged with oxygen for about one hour. The solution was mixed with water forming an emulsion and pentane was stripped under vacuum and replaced with ether. The aqueous layer was separated and the organic layer was washed three times with 100 ml. portions of water. The organic layer was dried over anhydrous sodium sulfate, the latter removed by filtration and the solvent stripped from the product under vacuum. A yield of 12.9 grams of a product identified as a mixture of N-(l0-nitro-9-octadecanonyl)- N-octanoyl-l,3-diaminopropane and N-(9-nitro-10-octadecanonyl)-N'-octanoyl-1,3-diaminopropane was recovered.

EXAMPLE IV To a solution of 28.3 grams (0.05 mole) of N-(C alkyl-N'-(9-octadecenoyl) 1,3 diaminopropane in 300 milliliters of carbon tetrachloride as inert solvent, there was added simultaneously oxygen at the rate of 60.8 ml. per minute and dinitrogen tetroxide at the rate of 0.015 mole per hour for 3.2 hours at 0 C. After 3.2 hours 3.1 ml. of liquid dinitrogen tetroxide (0.05 mole) had been transferred to the reaction flask and the solution was purged with oxygen for about one hour. The reaction mixture was washed three times with 100 ml. portions of water. The organic layer was dried over anhydrous sodium sulfate and the solvent was stripped from the product under vacuum. A yield of 18.8 grams of a product identified as a mixture of N-(C alkyl-N-(10-nitro-9-octadecanonoyl)-1,3-diaminopropane and N-(C alkyl-N- (9-nitro-10-octadecanonoyl)-l,3-diaminopropane was recovered.

EXAMPLE V The base fuel employed in the following examples was a premium grade gasoline having a research octane number of about 101.5 containing 3.0 cc. of tetraethyllead per gallon. This gasoline consisted of about 25 percent aromatic hydrocarbons, 14.5 percent olefin hydrocarbons, 60.5 percent parafiinic hydrocarbons and boiled in the range of about F. to 380 F.

A gasoline blend was prepared consisting of the above base fuel containing 5 p.t.b. (pound per 1000 barrels of gasoline) of an acid amide mixture of N-(9-octadecenyl)- N-(9-octadecenoyl)-1,3-diaminopropane and N-(9-octadecenyl) N (9 octadecenoyl) 1,3-diaminopropane. Another gasoline blend was prepared consisting of the above base fuel containing 5 p.t.b. of the nitroketonized acid amide reaction product of Example I. The base fuel and each of the additive-containing gasoline blends were tested and compared for their carburetor detergency properties in the above described Chevrolet V-8 Carburetor Detergency Test. From the test, it was determined that the gasoline blend containing the acid amide additive mixture was 39 percent more effective than the base gasoline in preventing the build-up of deposits in the carburetor. The gasoline blend containing the nitroketonized acid amide additive was 63 percent more effective than the base gasoline in preventing the build-up of deposits in the carburetor.

EXAMPLE VI To a solution of 14.7 grams (0.025 mole) of a mixture of N (9 octadecenyl)-N'- (9-octadecenoyl)l,3-diaminopropane and N (9 octadecenyl) N (9-octadecenoyl)-l,3-diaminopropane in 200 ml. of n-hexane as inert solvent, there was added simultaneously oxygen at a rate of 60.8 milliliters per minute and dinitrogen tetroxide at the rate of 0.019 mole per hour for 2.7 hours at 0 C. After 2.7 hours, 3.0 milliliters of liquid dinitrogen tetroxide (0.05 mole) had been transferred to the reaction flask and the solution was purged with oxygen for one-half hour. Dimethylformamide (15 ml.) was added to the reaction solution dropwise over a period of 8 minutes at 2 to 5 C. The solution was mixed with 100 milliliters of 5 percent aqueous sodium bicarbonate. Hexane was removed from the resulting mixture and replaced with 400 milliliters of benzene. The aqueous phase was separated and the benzene layer was washed three times with 200 milliliter portions of water. The benzene solution was dried over anhydrous sodium sulfate, the latter removed by filtration and the solvent stripped from the product under vacuum. A yield of 7.3 grams of a product composed of a mixture of N( -nitro-9-octadecanonyl -N'( 10-nitro-9- octadecanonoyl)-1,3-diaminopropane,

N( 10-nitro-9-octadecanonyl -N-( 10-nitro-9- octadecanonoyl) -1,3-diamin0propane,

N( 10 nitro-9-octadecanonyl) -N-(9-nitro- 10'- octadecanonoyl 1,3-diaminopropane,

N( 10-nitro-9-octadecanonyl) -N- (9-nitro-10- octadecanonoyl)-1,3-diaminopropane,

N- (9-nitro-l 0-octadecanonyl -N'-( 10-nitro-9- octadecanonoyl) -1,3-diaminopropane,

N- (9-nitro- 10-octadecanonyl) -N-( l0-nitro-9- octadecanonoyl 1,3-diaminopropane,

N-(9-nitro-10-octadecan0nyl)-N-(9-nitro-1O- octadecanonoyl)-1,3-diaminopropane, and

N-(9-nitro-10-octadecanonyl) -N- (9-nitro-10- octadecanonoyl)-1,3-diaminopropane was obtained.

The base fuel employed in this example was a premium grade gasoline having a research octane number of about 102.0 containing 2.86 cc. of tetraethyllead per gallon. This gasoline consisted of about 34 percent aromatic hydrocarbons, 9 percent olefinic hydrocarbons, 57 percent paraffinic hydrocarbons and boiled in the range of about 90 F. to 380 F. A gasoline blend was prepared consisting of the base fuel containing 32 p.t.b. of nitroketonized reaction product recited in Example VI. The base fuel and gasoline blend above were tested for the carburetor antiicing properties. The stalling time of base fuel at 0.5 inch of mercury was 47 seconds and at 0.9 inch of mercury was 54 seconds. The gasoline blend containing 32 pounds per thousand barrels of the nitroketonized reaction product at 0.5 inch of mercury was 260 seconds and at 0.9

inch of mercury was 274 seconds.

Another gasoline blend was prepared consisting of the above base fuel and containing 32 p.t.b. of the nitroketonized acid amide of Example II. The stalling time of this gasoline blend at 0.5 inch of mercury was 231 seconds and at 0.9 inch of mercury was 264 seconds.

The anti-rusting properties of the base fuel alone and 'base fuels containing 32 pounds per thousand barrels of the nitroketonized reaction products of Examples II and VI respectively were determined employing the test procedure heretofore described. An examination of the coldrolled steel strip contacted with the fuel layer in the base fuel revealed that about 95 percent of the surface area had rusted. In comparison, the base fuels containing respectively the nitroketonized products of Examples II and VI showed zero percent rusting of the surface area contacted with the fuel layer.

EXAMPLE VII The nitroketonized product of Example I was evaluated to determine its affect, if any, on a motor fuels research octane at various concentrations with the results tabulated as follows.

Research octane number None (base gasoline) '101.5 Nitroketonized amide 64 p.t.b 101.6 Nitroketonized amide 128 p.t.b 101.6 Nitroketonized amide 256 p.t.b 101.5

From the tabulation it will be seen that even at high concentrations the additive caused no significant change in octane number.

We claim:

1. A motor fuel composition comprising a mixture of hydrocarbons in the gasoline boiling range and from about 0.0001 to 0.1 weight percent of a nitroketonized amide corresponding to the formula:

R-NCHzCHz-OHzN-H I Ru where R is an alkyl, alkenyl, vicinal nitroketonized alkyl or nitroketonized alkenyl group, where R and R" alternately represent hydrogen and an alkanoyl, alkenoyl, vicinal nitroketonized alkanoyl or vicinal nitroketonized alkenoyl group, wherein at least one of said R, R or 'R" is a nitroketonized group as heretofore defined.

2. A'motor fuel composition according to claim 1 containing from about 0.001 to 0.02 weight percent of said nitro-ketonized amide.- 4 i 3. A motor fuel composition according to-claim 1 where R when alkyl has from 1 to 40 carbon atoms and when R is alkenyl, nitroketonized alkyl or nitroketonized alkenyl has from 4 to 40 carbon atoms and where R and R" when other than hydrogen represent a group having from .4 to 40 carbon atoms. p v p I 4. A motor fuel composition according to claim 1 where R has from 8 to 22 carbon atoms.

5. A motor fuel composition according to claim 1, where R or R" has from 8 to 22 carbon atoms. 1

6. A motor fuel composition according to claim 1 wherein said nitroketonized amide comprises N(lO-nitro- 9 octadecanonyl) N (9-octadecenoyl)-1,3-diaminopropane.

References Cited UNITED STATES PATENTS 1/ 1960 Lindstrom et al. 44-66 6/1968 Bouffard 44--72 X DANIELE. WYMAN, Primary Examiner WQJ. SHINE, Assistant Examiner