CA1208236A

CA1208236A - Compositions for use in alcohol and alcohol containing fuels

Info

Publication number: CA1208236A
Application number: CA000420524A
Authority: CA
Inventors: Thomas R. Hopkins
Original assignee: Lubrizol Corp
Current assignee: Lubrizol Corp
Priority date: 1982-02-03
Filing date: 1983-01-28
Publication date: 1986-07-22
Also published as: ES8403435A1; MX163254B; JPH0238120B2; EP0086049B1; AU1082583A; BR8300416A; EP0086049A1; JPS58134192A; DE3368438D1; IN158027B; ES519483A0; ZA83684B; AU563150B2; MX174305B

Abstract

COMPOSITIONS FOR USE IN ALCOHOL AND
ALCOHOL CONTAINING FUES

Abstract of Disclosure Corrosion inhibiting additive compositions for use in alcohol and alcohol containing normally liquid hydro-carbon fuels derived by the reaction of at least one suc-cinic acylating agent and at least one monoamine having the formula (R1)(R2)(R3)N wherein R1 is a hydrocarbon based radical and R2 and R3 are independently hydrogen or hydro-carbon based radicals and alcohol and alcohol containing normally liquid hydrocarbonaceous petroleum distillate fuels containing said additive compositions are disclosed.

Description

:12~ 36 COMPOSITIONS FOR USE IN ALCOHOL AND
ALCOHOL CONTAINING FUELS

Field of the Invention .
This invention relatas to corrosion inhibiting compositions for use in alcohol and alcohol containing nor-mally liquid hydrocarbon fuels. This invention further re-lates to alcohol and alcohol containing normally liquid hy drocarbon fuels containing said compositions and character-ized by improved coxrosion inhibition.
Back~round of the Invention Alcohol fuels and alcohol containing normally li~uid hydrocarbon fuels for use in spark-ignited and com-pression-ignited internal combustion engines possess a high degree of corrosive activity. This higher activity is gen-erally attributed to the presence of acidic and halogen ioncontaining contaminants present in alcohols but not present in normally liquid hydrocarbon fuels. These alcohol con-taminants are particularly distructive to various non-fer-rous metal~ and metal coating3 such a3 tin/lead alloy coatings (iOe~ terne coating~) employed on internal sur-faces of fuel tanks and fuel line~ and to zinc/aluminum metal alloys employed in the construction of carburetors.
AS a result motor vehicles employing alcohol and alcohol containing normally liquid hydrocarbon fuels have shown a greater propensity toward corrosion in the fuel tank, fuel line and fuel induction system areas.

~2~8;~36 As is well known, many patents exist which dis~
close various corrosion inhibiting additives for use in normally liquid hydrocarbon fuels. Seel for example, U.S.
Pat. No. 2,993,771 which relates to a process for pxevent-ing deposit ormation and corrosion of internal combustionengines from substantially hydrocarbon fuels and particu-larly gasoline, by the addition of additives to such fuels.
Two patents which are specifically directed to corrosion inhibition in alcohol or alcohol containing hydrocarbon fuels, e.g., gasohol, axe U~S. Pat. Nos. 4,282,007 and 4,282,008. In the former are disclosed additives compris-ing the reaction product of aminotriaæoles and polyisobut-enyl succinic acid anhydride and in the latter reaction products of an aminokriazole, isatoic anhydride and N-al-15 kylpropylene diamine.
It is the object of this invention to provide other corrosion inhibiting additives for use in alcohol and alcohol containing normally liquid hydrocarbon fuels~ It is a further object of this invention to provide alcohol 20 and alcohol containing normally liquid hydrocarbon fuels containing said additives~ It is yet a further object of this invention to provide alcohol and alcohol containing normally liquid hydrocarbon fuels characterized by im,proved corrosion inhibition, Further objects of this invention 25 will become apparent from the description thereof set forth hereinbelow.
Summary of the Invention In it~ broadest sense the present invention re-lates to compositions for use in alcohol and alcohol con-30 taining normally li~uid hydrocarbonaceous petroleum dis-tillate fuels said compositions comprising a corrosion inhibiting reaction product of (A) at least one succinic acylating agent selected from the group consisting of un-substituted succinic acylating agents and aliphatic hydro-35 carbon based substituted succinic acylating agents and(B~,,at least one amine~-oæ the formula Rl ~ N-R3 wherein Rl is a hydrocarbon based radical and R2 and R3 are independently hydrogen or hydrocarbon based radicals with the proviso that when R2 and R3 are both hydrogen, Rl is a hydrocarbon based radical selected from the group consisting of tertiary alkyl, cycloalkyl, aryl, aralkyl and alkaryl radicals to provide said alcohol and alcohol containing hydroca~bonaceous petroleum distillate fuels with improved corrosion inhibition.
The invention further relates to fuel compositions for use in internal combustion engines comprising (A) a major portion of a fuel containing (i) from about 2 to 100 pexcent by volume of an alcohol containing from 1 to about 5 carbon atoms and (ii) from about 98 to 0 percent by volume of 15 a normally li~uid hydrocarbonaceous petroleum distillate fuel and (B) a minor portion of the corrosion inhibiting reaction product generally deæcribed hereinabove.
Detailed Description of the Invention The corrosion inhibiting additives comprising one 20 aspect of this invention are prepared by the reaction of a succinic acylating agent selected from the group consisting of unsubstituted succinic acylating agent and aliphatic hydrocarbon based substituted succinic acylating agents, and a monoamine as defined hereinbelow.
2S As uæed herein, the term "hydrocarbon-based" or "hydrocarbon-based radicals" denotes a radical having a carbon atom directly attached to the remainder of the mol-ecule and having predominantly hydrocarbon character within the context o~ this in~ention. Such radicals include the 30 following:
(1) Hydrocarbon radicals; that is, aliphatic, (e.g., alkyl or alkenyl), alicyclic (e.g., cycloalkyl or - cycloalkenyl), aromatic, aliphatic- and alicyclic substi-tuted aromatic, aromatic-substituted aliphatic and alicyclic 35 radicals, cyclic radicals wherein the ring is completed ~Z~8Z36 ~hrough another portion o the molecule (that is, any two indicated substituents may together form an alicyclic rad-ical~ and the like as well as two or more fused benzene nuclei~ Such radicals are known to those skilled in the art, representative examples of which include methyl, ethyl, propyl, butyl, octyl, decyl, dodecyl, cyclohexyl, phenyl, tolyl, benzyl, naphthyl, anthryl, phenanthryl and the like.

(2) Substituted hydrocarbon radicals; that is, radicals containing non-hydrocarbon substituents which, in the context of this invention, do not alter the predomi-nantly hydrocarbon character of the radical. Those skilled in the art will be aware of suitable substituents (hydroxy, alkoxy, carbalkoxy, e~c.).
The succinic acylating agents useful in preparing the additive compositions of this invention are the unsub-stituted and aliphatic hydrocarbon basea substituted suc-cinic acids and anhydrides thereof having the following structural formulae Acid Anhydride ,~ O ,~ O
R CH-C~ R-CH-C
~ OH
.. O
/ OH
2 ~ CH -C

where R is hydrogen or an aliphatic hydrocarbon based rad-ical containing from about 3 to about 100 carbon atoms, pxeferably from about 8 to about 30 carbon atoms and most preferably from about 9 to about 15 carbon atoms. Although the source of the aliphatic hydrocarbon based substituent is not a critical aspect of the invention, this substituent will generally be a l-mono-olefin or oligomers, prepolymers or low molecular weight polymers thereof. Representative examples of such l-monoolefins include ethylene, propylene, l-butene, isobutene, l-hexene, l-octene, 2-methyl-1-heptene,

3-cyclohexyl-1-butene, 2-methyl-5-propyl-1-hexene and the like. Medial monoolefins, i.e., olefins in which the ole-finic linkage is not at the terminal position, and oligo-5 mers, prepolymers and low molecular weight polymers and lowmolecular weight polymers thereof are also useful. Illus-trative examples of such medial olefins include 2-butene, 3-pentene and 4-octene.
Although both unsubstituted succinic acylating agents and aliphatic hydrocarbon based substituted succinic acylating agents can be used in preparing the additive compositions of this invention the aliphatic hydrocaxbon based substituted succinic acylating agents are preferred.
They are well-known and can be prepared by various known 15 procedures. one particularly useful procedure is to react a monoolefin monomer or oligomer, prepolymer or low molecular weight polymer thereof as described above with maleic anhy-dride at 100C to 200C with or without a catalyst to form the corresponding substituted æuccinic anhydride. The 20 monoolefin also can be replaced by an alkyl halide which is capable of being substituted onto the unsaturated anhydride or the equivalent free acid thereof.
The aliphatic hydrocarbon based substituent can be saturated or unsaturated, straight-chain or branched-chain 25 and may contain polar groups provided, however, that such groups are not present in significantly large proportions as to alter the hydrocarbon character of the substituent~
Polar groups are typified by halo, carbonyl, nitro and similar groups, In a preferred embodiment, the aliphatic 30 hydrocarbon based substituent is a polyisopropenyl radical containing 12 carbon atoms.
The amines which are useful in preparing the additive compositions are monoamines which have the formula iZ~lYZ36 wherein Rl is a hydrocarbon based radical and R2 and R3 are independently hydrogen or hydrocarbon based radicals with the proviso that when R2 and R3 are both hydrogen, Rl is a hydrocarbon based radical selected from the group consist-ing of tertiary alkyl, cycloalkyl, aryl, alkaryl and aralkylradicals. In the inventions broader scope, the monoamines of the formula above can be straight~chain or branched-chain aliphatic, alicyclic and aromatic amines; mono-amines wherein each of Rl, R2 and R3 are dissimilar such as aliphatic-alicyclic, aliphatic-aromatic and alicyclic-aromatic amines and substituted amines such as aliphatic substituted ali-cyclic, aliphatic substituted aromatic, alicyclic substi-tuted aliphatic, alicyclic substituted aromatic, aromatic substituted aliphatic and aromatic substituted alicyclic amines. Moxe specifically, the monoamin2s useful in pre-paring the compositions comprising one aspect of the in-vention are those amines defined by the above formula wherein Rl is a hydrocarbon based radical containing from 1 to about 24 carbon atoms selected from the group consisting 20 of straight-chain and branched-chained alkyl radical~ con-taining from 1 to abouk 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 ~o about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to 25 about 20 carbon atoms and R2 and R3 are hydrogen or hydro-carbon based radicals selected from the group consisting of straight-chain or branched alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals con-30 taining from about 6 to about 14 carbon atoms and alkaryland aralkyl radicals containing from about 7 to about 20 carbon atoms. When R2 and R3 are both hydrogen, thereby making the amine defined above a primary amine, then Rl is a hydrocarbon based radical selected from the group consisting 35 of tertiary alkyl radicals containing from about 5 to about 7 carbon atoms, cycloalkyl radicals containing fxom 4 to about 24 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 5 to about 7 carbon atoms. The pur-pose of the proviso described above is to ensure that Rl will possess sufficient inherent stearic hindrance to in-5 hibit any imide formation, the additive compositions of thepresent invention being primarily amidic acid salts or mixtures of amidic acid and amidic acid salts depending on the nature of the starting reactants and the relative ratios employed thereo. The amines will be free of any acetylenic 10 unsaturation in the event any of the R groups of the amine should be unsaturated.
Representative, but nonlimiting examples of mono-amines useful in the preparation of the additive composi-tions comprising one a~pect of this invention include di-15 methylamine, triethylamine, diethylamine, triethylamine,dipropylamine, tripropylamine, diisopropylamine, dibutyl-amine, tributylamine, diisobutylamine, triisobutylamine, tertiary butylamine, ethyl-n-butylamine, dimethyl butyl-amine, di-n-amylamine, tri-n-amylamine, dihexylamine, tri-20 hexylamine, dioctylamine, trioctylamine, N-dodecyl-l-do-decanamine, N-octadicyl-l-octadecanamine, N,N-dimethyl-l-octadecanamine, cyclopentylamine, cylopentenylamine, cyclo-hexylamine, dicyclohexylamine, methyl ethanolamine, ben-zylamine, aniline, o-phenylaniline, diphenylamine, 2-methyl-25 diphenylamine, 3-methyldiphenylamine, 4,4'-dimethyldiphen-ylamine, 2,2'-diethyldiphenylamine, 4,4'-dioctyldiphenyl-amine, N-phenyl-l naphthylamine, N-phenyl-2-naphthylamine and the like.
In one embodiment, the additive compositions are 30 prepared by the reaction of the succinic acylating agent with secondary amines, or mixtures of secondary and tertiary amines in the manner described hereinbelow. In a preferred embodiment the additive compositions are prepared by the reaction of the succinic acylating agent with secondary 35 amines. A most preferred secondary amine for use i2~8~236 in preparing the additive compositions comprising one aspect of this invention is dicyclohexylamine.
The corrosion inhibiting additive compositions of the presen~ invention may be readily prepared by heating mixtures of the unsubstituted or aliphatic hydrocarbon based substituted succinic acylating agent with the amine at elevated temperatures ranging from about 30C to about 200C. A more preferred range of temperatures is from about 50C to about 150C. Generally, however, very reasonable rates of reaction can be achieved from about 50C to about The proportions of the reactants can vary widely.
For example, the molar ratios o the unsubstitut~d or ali-phatic hydrocarbon-based substituted succinic acylating agent to the monoamine can range from about 1.0/0.5 to about 1.0/3Ø However, the preferred molar ratios range from about 1.0/1.0 to about 1.0/2.0 with the most preferred molar ratio being 1.0/2Ø
The preparation of the addi~ive compositions herein described can be carried out either in the absence or presence o a solvent. Preferably the compositions are prepared in the presence of solvent. Useful solvents can be hydrocarbon or polar solvents including, for example benzene naphtha, toluene, xylene, n-hexane, dioxane, chlorobenzene, kerosene, gasoline or a fuel oil or oil of lubricating viscosity, The following examples illustrate the preparation of the additive compositions comprising one aspect of this invention and the improved cor~osion inhibiting character-istics of alcohol or alcohol containing normally liquidfuels containing these compositions t which fuels comprise another aspect of this invention. In the following examples all parts are by weight unless otherwise specified.

1;2~3G

Example 1 Three hundred sixty-seven parts of tetrapropenyl-substituted succinic anhydride (prepared by reacting maleic anhydride with a polypropylene tetramer and having an av-S erage M.W. of about 248) is charged to a reaction vesselequipped with a stirrer, thermometer, reflux condenser and addition funnel. Starting at room temperature, 500 parts dicyclohaxylamine is added over a period of 0.5 hour. The temperature of the reaction mixture rises to 45C during the 10 addition. The reaction is continued for 4.5 hours at 45C.
The temperature is increased to 60C. over 0.5 hour. The reaction product is then filtered and collected.
Example 2 Two hundred sixty-five parts of tetrapropenyl-sub-15 stituted succinic anhydride, as described in Example 1, ischarged to a reaction vessel equipped with a stirrer, ther-mometer, reflux condenser and addition funnel. Three hun-dred sixty-two parts of dicyclohexylamine is then added to the reaction vessel over a period of 2 hours while heating 20 the reaction mixture to 120C. The addition of the amine to the succinic anhydride is exothermic. The reaction is continued for 3 hours at 120C. Three hundred twenty two parts kerosene is then added to the reaction mixture. The materials are mixed thoroughly, filkered and collected.
Two hundred sixty-six parts of tetrapropenyl-sub-stituted succinic anhydride, as described in Example 1, and 333 parts of xylene are charged to a reaction vessel as described in the previous examples. The mixture is heated to 110C. with stirring, followed by the addition of 362 parts dicyclohexylamine over a period of one hour at 110-120C. The reaction is continued for 3.25 hours at 110C.
The reaction mixture is then filtered and collected.

IZq;~8~3tj Example 4 Two hundred forty-eight parts of an oil solution of tetrapropenyl-~ubstituted succinic acid (prepared by reacting tetrapropenyl-substituted succinic anhydride with 5 water) are charged to a reaction vessel equipped as de-scribed in Example l. Two hundred parts of dicyclohexyl-amine are then added over a period of 0.5 hour. The tem-perature of the reaction mixture rises from room temperature to 49C. during the amine addition. One hundred sixteen 10 parts of mineral oil are then added and the mixture stirred for an additional 0.5 hour. The materials are then filtered and collected.
Example 5 Two hundred sixty-six parts of tetrapropenyl-15 substituted succinic anhydride is charged to a reactionvessel as described in Example 1. The anhydride is heated to 100C., followed by the addition of 20 parts of distilled water. The materials are reacted for 1.75 hours at 100C.
The reaction product (i.e., tetrapropenyl-substituted suc-20 cinic acid) is then cooled to 55C., at which time 362 partsdicyclohexylamine are then added to the acid. The addition of the amine is exothermic and the temperature o the re-action mixture increases to about 65C. The reaction mix ture is then heated to 70C~ and reacted at this temperature 25 for 4 hours. After cooling, 349 parts xylene are added.
The xylene solution of reaction product is stirred thor-oughly, filtered and collected.
Example 6 A reaction vessel equipped in the manner as de-30 scribed in Example 1 is charged with 98 parts of tetra-propenyl-substituted succinic anhydride (average M.W. 268) and 60 parts xylene. A solution consisting of 134 parts dicyclohexylamine and 65 parts xylene is then added over 0.5 hour. With addition of the amine solution the temperature 35 of the reaction mixture increases from room temperature to 120~36 about 34C. The reaction mixture is then heated to 75C.
and reacted at that temperature for a total of 5 hours. The solution containing the reaction product is then cooled, 5 filtered and collected.

Two hundred sixty-six parts of tetrapropenyl-substituted succinic anhydride are charged to a reaction vessel equipped as described in Example 1. Then 374 parts 10 Primene 81R (a mixtur~ of C12-14 t-alkyl primary amines available commercially from Rohm & Haas Co.) are added dropwise over 3 hours. The reaction is exothermic and the temperature of the reactant increases from room temperature to about 59C, over the course of the amine addition. One 15 hundred sixty parts of diluent oil are then added to the reaction product and stirring is continued ~or an additional hour at 55C. After cooling to 40C~ the material is filtered and collected.
Ex~ple 8 Two hundred twenty-six par~s of tetrapropenyl-~ubstituted succinic anhydride is charged to a reaction vessel as described in Example 1. Then 362.6 parts of dicyclohexylamine is added dropwise to the reaction vessel over one hour~ The reaction of the anhydride and amine is 25 exothermic and the temperature of the reaction mixture increases to 36C. The mixture is reacted at 36-45C. while heating for one hour. The product is then filtered and collected.

To a solution of 266 parts tetrapropenyl-sub-stituted succinic anhydride in 253 par~s xylene con~ained in a reaction vessel as described in Example 1 is added a solution of 362.6 part~ dicyclohexylamine in 85 parts xylene over a period of one hour. The temperature increases exo-35 thermically to 32C. during the addition. The materials are then reacted at 32-50C. for one hour, filtered and col-lected. Sixty parts of this product is then diluted further with 40 parts xylene and mixed thoroughly.
* trade mark ~2~Z36 Exam~le 10 A series of alcohol fuels are prepared by blending from 35 to 450 part~ by weight of one of the reaction pro-ducts of Examples 1 through 9 with hydrated ethanols con~
5 taining about 7~5 percent by weight watert Exam~le 11 A series of alcohol containing gasoline fuels is pxepared by blending from 35 to 450 parts by weight of one of the reaction products of Examples 1 through 9 with a 10 gasohol which comprises 20 percent by volume of hydrated ethanol and 80 pexcent by volume of a gasoline having an ASTM distillation range of from about 60C. at the lO per-cent di~tillation point to about 205Co at the 90 percent distillation point.
The corro~ion inhibiting effectiveness of the additive compositions were tested in accordance with Method K, Test C of the Brazilian Association of T~chnical Norms (ABNT). In this test, various metal specimens (e.g. steel, brass and zinc/aluminum alloy) are immersed in commercially 20 available hydrated ethanol for a continuous period of 144 hours at a temperature of 50C + 3C. At the end of the test period each test specimen is then rinsed first with water and then with a ketone or other suitable solvent and dried~ After drying, each test specimen is weighed and its visual appearance noted. The weight loss, if any, and visual appearance of the Cpecimens are then compared to those of specimens treated in the same manner in a control or reference gasoline/alcohol blend comprised o~ 78 to 82 percent by volume of gasoline and 22 to 18 percent by volume 30 of 100 percent absolute ethanol. For a corrosion inhibiting additive composition to be considered effective, neither the weight loss nor the visual appearance of specimens tested with additive containing hydrated ethanol can vary from those treated in the control or reference gasoline/alcohol blend 35 by more than 10 percent. Th~ corrssion inhibiting additive compositions described in Examples 1 through 9 above are i2~ 3~;j found to be effective when tested in accordance with this Brazilian method. Another aspect of this invention com-prises fuel compositions for use in internal combustion engines comprising tA) a major portion of a fuel containing (i) at least one alcohol having from l to about five carbon atoms and (ii) a normally liquid hydrocarbonaceous petroleum distillate fuel and (B) a minor portion of a corrosion inhibiting reaction product as described hereinabove, i.e.
the reaction product of (i) at least one succinic acylating agent selected from the group consisting of unsubstituted and aliphatic hydrocarbon based substituted succinic acy-lating agent and (ii) at least one amine of the formula Rl ~ N-R3 wherein Rl, R2 and R3 have the same meanings as set forth above, Alcohol fuels useful in combination with the corrosion inhibiting reaction products of ~uccinic acylating agents and amines as described herein to provide fuel compositions having improved corrosion inhibiting charac-teristics include such commercially available alcohols as methanol, ethanol, propanol, isopropanol, butanol and its isomer and amyl alcohol and its isomers and mixtures of these various alcohols. As produced commercially the pre-ferred alcohols are methanol and ethanol.
The normally liquid hydrocarbonaceous petroleum distillate fuels which are useful in combination with al-cohols and the corrosion inhibiting reaction products de-scribed herein above include motor ga~oline as defined by ASTM Specification D439 and diesel fuel or fuel oil as defined by ASTM Specification D396O A particularly pre-ferred petroleum distillate uel, however, is gasoline, that is, a mixture of hydrocarbons having an ASTM distillation range of from about 60C at the lO percent distillation point to about 205C at the 90 percent distillation point.

~2~8'~3t;

The fuel portion of the fuel compositions of this invention comprise from about 2.0 to 100 percent by volume of at least one alcohol containing from 1 to about 5 carbon atoms and from about 98.0 to 0 percent by volume of the 5 normally liquid hydrocarbonaceous petroleum distillate fuel.
In a preferred embodiment, this fuel portion will comprise from about 10.0 to 100 percent by volume of at least one alcohol containing from 1 to about 5 carbon atoms and from about 90.0 percent to 0 percent of the petroleum distillate 10 fuel. In a more preferred embodiment, the ranges of the alcohol and petroleum distillate fuels employed in the fuel compositions of this invention will be from about 20.0 to 100 percent by volume and from about 80.0 to 0 percent by volume respectively. Particularly preferred fuel composi-15 tions are tho~e based on a mixture of an alcohol, especiallymethanol or ethanol, and a petroleum distillate fuel, especially gasoline, in which mixture the alcohol component ranges from about 10.0 to about 20.0 percent by volume and the petroleum distillate fuel ranges from about 90.0 to 20 about 80.0 percen~ by volume.
The amount of the additive reaction product of the succinic acylating agent and amine added to the above de-scribed fuel portion to provide the fuel compositions of the invention will be an amount sufficient to impart improved 25 corrosion inhibiting characteristics to these fuel compo-sitions~ ~roadly this amount will range from about 10 to about 1000 parts by weight of said additive reaction product per million parts by weight of the fuel portion. Preferably this amount will range from about 10 to about 450 parts by 30 weight with a range of from about 175 to about 450 parts by weight of said additive reaction product per million parts by weight of said fuel portion being most preferred.
The fuel compositions of this invention can be prepared by merely adding the reaction product of the suc-35 cinic acylating agent and amine directly to the fuel portionor it can be diluted with a substantially inert, normally i2~ 3~

liquid organic diluent such as naphtha, benzene, toluene, xylene, or a petroleum distillate fuel as described above, to form a concentrate of said reaction product which is then added to the fuel portion. These concentrates, which 5 constitute yet another embodiment of the invention, gen-erally contain from about 20 percent to about 90 percent of the additive reaction products of the invention.
The fuel compositions described hereinabove, may also contain additional materials normally added to liquid 10 fuels to obtain specific benefits. Therefore, the fuel compositions, representing one aspect of this invention, may contain antiknock agents such as tetraalkyl lead compounds, lead scavengers such as haloalkanes (e.g., ethylene di-chloride and ethylene dibromide) deposit preventers or 15 modifiers such triaryl phosphates, dyes, octane improvers, antioxidants such as Z,6-di-tertiary-butyl-4-methylphenol, bacteriostatic agents, gum inhibitors, metal deactivators, demulsifiers, upper cylinder lubricants and anti-icing agents.
The compositions for use in alcohol and alcohol containing normally li~uid hydrocarbonaceous petroleum dis-tillate fuels and the fuel compositions based thereon as well as their methods of preparation have been specifically set forth above to assist those skilled in the art in 25 understanding and practicing the invention. Based on the teachings herein, many variations and departures from these specific disclosures will be obvious to those skilled in the art. Such variations and departures are contemplated as being within the scope and spirit of the present invention 30 as defined by the appended claims.

Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. Compositions for use in alcohol and alcohol containing normally liquid hydrocarbonaceous petroleum dis-tillate fuels comprising a reaction product of (A) at least one succinic acylating agent selected from the group con-sisting of unsubstituted and aliphatic hydrocarbon based substituted succinic acylating agents and (B) at least one amine of the formula wherein R1 is a hydrocarbon based radical and R2 and R3 are independently hydrogen or hydrocarbon based radicals with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl, cycloalkyl, aryl, alkaryl and aralkyl radicals to provide said alcohol and alcohol containing normally liquid hydrocarbonaceous petroleum distillate fuels with improved corrosion inhibition.

2, The compositions of Claim 1 wherein the succinic acylating agent (A) is an aliphatic hydrocarbon based substituted succinic anhydride or acid.

3. The composition of Claim 2 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (A) is a straight-chain or branched-chain alkyl or alkenyl radical containing from 3 to 100 carbon atoms.

4, The compositions of Claim 2 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (A) is a straight-chain or branched-chain alkyl or alkenyl radical containing from about 8 to about 30 carbon atoms.

5. The compositions of Claim 2 wherein the aliphatic hydrocarbon based substitutent on the succinic anhydride or acid acylating agent (A) is a straight-chain or branched-chain alkyl or alkenyl radical containing from about 9 to about 15 carbon atoms.

6. The compositions of Claim 3 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (A) is a straight-chain or branched-chain alkenyl radical.

7. The compositions of Claim 4 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (A) is a straight-chain or branched-chain alkenyl radical.

8. The compositions of Claim 5 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (A) is a straight-chain or branched-chain alkenyl radical.

9. The compositions of Claims 6, 7 or 8 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (A) is polypropenyl radical containing 12 carbon atoms.

10. The compositions of Claim 1 wherein (B) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

11. The compositions of Claim 2 wherein (B) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

12. The compositions of Claim 3 wherein (B) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

13. The compositions of Claim 4 wherein (B) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

14. The compositions of Claim 5 wherein (B) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

15. The compositions of Claims 10, 11 or 12 wherein R2 is a hydrocarbon based radical and R3 is hydrogen.

16. The compositions of Claims 13 or 14 wherein R2 is a hydrocarbon based radical and R3 is hydrogen.

17. The compositions of Claim 10 wherein the hydro-carbon based radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals having from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing about 7 to about 20 carbon atoms.

18. The compositions of Claim 11 wherein the hydro-carbon based radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals having from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen and hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing about 7 to about 20 carbon atoms.

19. The compositions of Claim 12 wherein the hydro-carbon based radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals having from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 car-bon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing about 7 to about 20 carbon atoms.

20. The compositions of Claim 13 wherein the hydro-carbon based radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals having from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 car-bon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing about 7 to about 20 carbon atoms.

21. The compositions of Claim 14 wherein the hydro-carbon based radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals having from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 car-bon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing about 7 to about 20 carbon atoms.

22. The compositions of Claim 17 wherein R2 is a hydrocarbon based radical selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radi-cals containing from about 7 to about 20 carbon atoms, and R3 is hydrogen.

23. The compositions of Claim 18 wherein R2 is a hydrocarbon based radical selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radi-cals containing from about 7 to about 20 carbon atoms, and R3 is hydrogen.

24. The compositions of Claim 19 wherein R2 is a hydrocarbon based radical selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radi-cals containing from about 7 to about 20 carbon atoms, and R3 is hydrogen.

25. The compositions of Claim 20 wherein R2 is a hydrocarbon based radical selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radi-cals containing from about 7 to about 20 carbon atoms, and R3 is hydrogen.

26. The compositions of Claim 21 wherein R2 is a hydrocarbon based radical selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radi-cals containing from about 7 to about 20 carbon atoms, and R3 is hydrogen.

27. The compositions of Claim 22 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

28. The compositions of Claim 23 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

29. The compositions of Claim 24 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

30. The compositions of Claim 25 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

31. The compositions of Claim 26 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

32. The compositions of Claim 27, 28 or 29 wherein R1 and R2 are cyclohexyl radicals.

33. The compositions of Claim 30 or 31 wherein R1 and R2 are cyclohexyl radicals.

34. Compositions for use in alcohol and alcohol containing normally liquid hydrocarbonaceous petroleum distil-late fuels comprising a reaction product of (A) at least one straight-chain or branched-chain alkenyl substituted succinic anhydride or acid and (B) at least one amine of the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals having from about 4 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals having from about 6 to about 14 carbon atoms, and alkaryl and aralkyl radicals having from about 7 to about 20 carbon atoms to provide said alcohol and alcohol containing normally liquid hydrocarbonaceous petroleum distillate fuels with improved corrosion inhibition.

35. The compositions of Claim 34 wherein R2 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R3 is hydrogen.

36. The compositions of Claim 34 wherein the hydro-carbon based radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals having from 1 to about 24 carbon atoms, cycloalkyl radicals having from about 5 to about 7 car-bon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl or aralkyl radicals containing from about 7 to about 20 carbon atoms.

37. The compositions of Claim 36 wherein R2 is a hydrocarbon radical selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals contain-ing from about 5 to about 7 carbon atoms, aryl radicals con-taining from about 6 to about 14 carbon atoms and alkaryl and aralkyl containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

38. The compositions of Claim 37 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

39. The compositions of Claim 38 wherein R1 and R2 are cyclohexyl radicals.

40. The compositions of Claim 34 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 3 to about 100 carbon atoms.

41. The compositions of Claim 35 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 3 to about 100 carbon atoms.

42. The compositions of Claim 36 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 3 to about 100 carbon atoms.

43. The compositions of Claim 37 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 3 to about 100 carbon atoms.

44. The compositions of Claim 38 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 3 to about 100 carbon atoms.

45. The compositions of Claim 39 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 3 to about 100 carbon atoms.

46. The compositions of Claim 40, 41 or 42 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 8 to about 30 carbon atoms.

47. The compositions of Claim 43, 44 or 45 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 8 to about 30 carbon atoms.

43. The compositions of Claim 40, 41 or 42 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 9 to about 15 carbon atoms.

49. The compositions of Claim 43, 44 or 45 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) contains from about 9 to about 15 carbon atoms.

50. The compositions of Claim 40, 41 or 42 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) is polypropenyl radical containing about 12 carbon atoms.

51. The compositions of Claim 43, 44 or 45 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid (A) is polypropenyl radical containing about 12 carbon atoms.

52. Fuel compositions for use in an internal com-bustion engine comprising (A) a major portion of a fuel con-taining (i) from about 2.0 to 100 percent by volume of at least one alcohol containing from 1 to about 5 carbon atoms and (ii) from about 98.0 to 0 percent by volume of a normally liquid hydrocarbonaceous petroleum distillate fuel and (B) a minor portion of a corrosion inhibiting reaction product of (i) at least one succinic acylating agent selected from the group consisting of unsubstituted and aliphatic hydrocarbon substituted succinic acylating agents and (ii) at least one amine of the formula wherein R1 is a hydrocarbon based radical and R2 and R3 are independently hydrogen or hydrocarbon based radicals with the proviso that when R2 and R3 are both hydrogen, R1 is a hydro-carbon based radical selected from the group consisting of tertiary alkyl, cycloalkyl, aryl, alkaryl and aralkyl radicals.

53. The fuel compositions of Claim 52 wherein the succinic acylating agent (B)(i) is an aliphatic hydrocarbon based substituted succinic anhydride or acid.

54. The fuel compositions of Claim 53 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is a straight-chain or branched-chain alkyl or alkenyl radical containing from about 3 to about 100 carbon atoms.

55. The fuel compositions of Claim 53 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is a straight-chain or branched-chain alkyl or alkenyl radical containing from about 8 to about 30 carbon atoms.

56. The fuel compositions of Claim 53 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is a straight-chain or branched-chain alkyl or alkenyl radical containing from about 9 to about 15 carbon atoms.

57. The fuel compositions of Claim 54 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is a straight-chain or branched-chain alkenyl radical.

58. The fuel compositions of Claim 55 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is a straight-chain or branched-chain alkenyl radical.

59. The fuel compositions of Claim 56 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is a straight-chain or branched-chain alkenyl radical.

60. The fuel compositions of Claim 54, 55 or 56 wherein the aliphatic hydrocarbon based substituent on the succinic anhydride or acid acylating agent (B)(i) is poly-propenyl radical containing 12 carbon atoms.

61. The fuel compositions of Claim 52 wherein (B)(ii) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from about 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen, R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals, containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

62. The fuel compositions of Claim 53 wherein (B)(ii) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from about 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen, R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals, containing from about 4 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

63. The fuel compositionsof Claim 54 wherein (B)(ii) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from about 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen, R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals, containing from about 4 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 car-bon atoms.

64. The fuel compositions of Claim 55 wherein (B)(ii) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from about 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen, R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals, containing from about 4 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 car-bon atoms.

65. The fuel compositions of Claim 56 wherein (B)(ii) is an amine having the formula wherein R1 is a hydrocarbon based radical containing from 1 to about 24 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon based radicals containing from about 1 to about 24 carbon atoms with the proviso that when R2 and R3 are both hydrogen, R1 is a hydrocarbon based radical selected from the group consisting of tertiary alkyl radicals containing from about 4 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 car-bon atoms.

66. The fuel compositions of Claim 61, 62 or 63 wherein R2 is a hydrocarbon based radical and R3 is hydrogen.

67. The fuel compositions of Claim 64 or 65 wherein R2 is a hydrocarbon based radical and R3 is hydrogen.

68. The fuel compositions of Claim 61, wherein the hydrocarbon radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from about 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

69. The fuel compositions of Claim 62, wherein the hydrocarbon radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from about 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

70. The fuel compositions of Claim 63, wherein the hydrocarbon radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from about 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

71. The fuel compositions of Claim 64 wherein the hydrocarbon radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from about 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

72. The fuel compositions of Claim 65 wherein the hydrocarbon radical R1 is selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals con-taining from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms, and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydrogen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from about 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

73. The fuel compositions of Claim 68 wherein R2 is a hydrocarbon based radical selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radi-cals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

74. The fuel compositions of Claim 69 wherein R2 is a hydrocarbon based radical selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radi-cals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

75. The fuel compositions of Claim 70 wherein R2 is a hydrocarbon based radical selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radi-cals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

76. The fuel compositions of Claim 71 wherein R2 is a hydrocarbon based radical selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radi-cals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

77. The fuel compositions of Claim 72 wherein R2 is a hydrocarbon based radical selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radi-cals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

78. The fuel compositions of Claim 73 wherein R1 and R2 are cycloalkyl radicals having from about 5 to about 7 carbon atoms.

79. The fuel compositions of Claim 74 wherein R1 and R2 are cycloalkyl radicals having from about 5 to about 7 carbon atoms.

80. The fuel compositions of Claim 75 wherein R1 and R2 are cycloalkyl radicals having from about 5 to about 7 carbon atoms.

81 The fuel compositions of Claim 74 wherein R1 and R2 are cycloalkyl radicals having from about 5 to about 7 carbon atoms.

82. The fuel compositions of Claim 77 wherein R1 and R2 are cycloalkyl radicals having from about 5 to about 7 carbon atoms.

83. The fuel compositions of Claim 78, 79 or 80 wherein R1 and R2 are cyclohexyl radicals.

84. The fuel compositions of Claim 81 or 82 wherein R1 and R2 are cyclohexyl radicals.

85. Fuel compositions for use in an internal com-bustion engine comprising, (A) a major proportion of a fuel containing (i) from about 10 to 100 percent by volume of methanol or ethanol and (ii) from about 90 to 0 percent by volume of a normally liquid hydrocarbonaceous petroleum dis-tillate fuel and (B) a minor portion of a corrosion inhibiting reaction product of (i) at least one straight-chain or branched-chain alkenyl substituted succinic anhydride or acid acylating agent and (ii) at least one amine of the formula wherein R1 is a hydrocarbon based radical and R2 and R3 are independently hydrogen or hydrocarbon based radicals with the proviso that when R3 and R3 are both hydrogen, R1 is a hydro-carbon based radical selected from the group consisting of tertiary alkyl, cycloalkyl, aryl, alkaryl and aralkyl radicals.

86. The fuel compositions of Claim 85 wherein R2 is a hydrocarbon based radical and R3 is hydrogen.

87. The fuel compositions of Claim 85 wherein the hydrocarbon based radical R1 is selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radi-cals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms, and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R2 and R3 are independently hydro-gen or hydrocarbon radicals selected from the group consisting of straight-chain or branched-chain alkyl radicals containing from about 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radi-cals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms.

88. The fuel compositions of Claim 87 wherein R2 is a hydrocarbon based radical selected from the group con-sisting of straight-chain or branched-chain alkyl radicals containing from 1 to about 24 carbon atoms, cycloalkyl radicals containing from about 5 to about 7 carbon atoms, aryl radicals containing from about 6 to about 14 carbon atoms and alkaryl and aralkyl radicals containing from about 7 to about 20 carbon atoms and R3 is hydrogen.

89. The fuel compositions of Claim 88 wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms.

90. The fuel compositions of Claim 89 wherein R1 and R2 are cyclohexyl radicals.

91. The fuel compositions of Claim 85 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 3 to about 100 carbon atoms.

92. The fuel compositions of Claim 86 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 3 to about 100 carbon atoms.

93. The fuel compositions of Claim 87 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 3 to about 100 carbon atoms.

94. The fuel compositions of Claim 88 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 3 to about 100 carbon atoms.

95. The fuel compositions of Claim 89 wherein the straight-chain or branched-chain alkenyl substituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 3 to about 100 carbon atoms.

96. The fuel compositions of Claim 90 wherein the straight-chain or branched-chain alkenyl substituent on the succinc anhydride or acid acylating agent (B)(i) contains from about 3 to about 100 carbon atoms.

97. The fuel compositions of Claim 91, 92 or 93 wherein the straight-chain or branched-chain alkenyl sub-stituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 8 to about 30 carbon atoms.

98. The fuel compositions of Claim 94, 95 or 96 wherein the straight-chain or branched-chain alkenyl sub-stituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 8 to about 30 carbon atoms.

99. The fuel compositions of Claim 91, 92, or 93 wherein the straight-chain or branched-chain alkenyl sub-stituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 9 to about 15 carbon atoms.

100. The fuel compositions of Claim 94, 95 or 96 wherein the straight-chain or branched-chain alkenyl sub-stituent on the succinic anhydride or acid acylating agent (B)(i) contains from about 9 to about 15 carbon atoms.

101. The fuel compositions of Claim 91, 92 or 93 wherein the straight-chain or branched-chain alkenyl sub-stituent on the succinic anhydride or acid acylating agent (B)(i) is polypropenyl radical containing 12 carbon atoms.

102. The fuel compositions of Claim 94, 95 or 96 wherein the straight-chain or branched-chain alkenyl sub-stituent on the succinic anhydride or acid acylating agent (B)(i) is polypropenyl radical containing 12 carbon atoms.

103. Fuel compositions for use in an internal combustion engine comprising (A) a major portion of a fuel containing (i) from about 20 to 100 percent by volume of ethanol and (ii) from about 80 to 0 percent by weight of a normally liquid hydrocarbonaceous petroleum distillate fuel and (B) a minor portion of a corrosion inhibiting reaction product of (i) at least one straight-chain or branched-chain alkenyl substituted succinic anhydride or acid acylating agent wherein said alkenyl substituent contains from about 9 to about 15 carbon atoms and (ii) at least one amine of the formula wherein R1 and R2 are cycloalkyl radicals containing from about 5 to about 7 carbon atoms and R3 is hydrogen.

104. The fuel compositions of Claim 103 wherein the normally liquid hydrocarbonaceous distillate fuel (A)(ii) is gasoline and the corrosion inhibiting reaction product (B) is the reaction product of (i) a straight-chain or branched-chain alkenyl substituted succinic anhydride or acid acyla-ting agent wherein said alkenyl substituent is polypropenyl radical containing 12 carbon atoms and (ii) dicyclohexylamine.