Search Images Maps Play YouTube News Gmail Drive More »
Sign in
Screen reader users: click this link for accessible mode. Accessible mode has the same essential features but works better with your reader.

Patents

  1. Advanced Patent Search
Publication numberUS3873278 A
Publication typeGrant
Publication dateMar 25, 1975
Filing dateNov 29, 1973
Priority dateNov 29, 1973
Also published asCA1008664A, CA1008664A1, DE2456574A1, DE2456574B2
Publication numberUS 3873278 A, US 3873278A, US-A-3873278, US3873278 A, US3873278A
InventorsPerry Polss
Original AssigneeDu Pont
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Gasoline
US 3873278 A
Abstract
Composition exhibiting good anti-stalling, anti-icing, anti-rust, detergent and water interaction properties and comprising a hydrocarbon mixture boiling in the gasoline range and an effective amount, usually 0.004-0.02% by weight, based on the weight of the hydrocarbon mixture, of an amine carboxylate salt of the formula WHEREIN R is C11-21 saturated or unsaturated aliphatic hydrocarbyl, R1 is C8-24 saturated or unsaturated aliphatic hydrocarbyl, each of R2 and R3 is selected from H and CH3, each of a and b is 1-14 and the sum of a and b is 2-15, said salt having at least two (CH2CH2O) groups, said composition having a Federal water rating of 1.
Images(6)
Previous page
Next page
Claims  available in
Description  (OCR text may contain errors)

United States Patent 1 Polss Mar. 25, 1975 GASOLINE [75] Inventor: Perry Polss, Wilmington, Del.

[73] Assignee: E. I. du Pont de Nemours and Company, Wilmington, Del.

22 Filed: Nov. 29, 1973 121 App]. No.: 419,973

Primary [:Imminer-Delbert E. GantZ ,ltprixrunl [i.\'an1inerl. Vaughn [57] ABSTRACT Composition exhibiting good anti-stalling, anti-icing,

anti-rust, detergent and water interaction properties and comprising a hydrocarbon mixture boiling in the gasoline range and an effective amount. usually 0.0040.02% by weight, based on the weight of the hydrocarbon mixture, of an amine carboxylatc salt of the formula 9 /(CHR c11 0) n a-c-o-NH(R (caR cH 0) H wherein R is C saturated or unsaturated aliphatic hydrocarbyl, R is C saturated or unsaturated aliphatic hydrocarbyl, each of R and R is selected from H and CH each of a and b is l-l4 and the sum of a and b is 2-15, said salt having at least two (CH CH O) groups, said composition having a Federal water rating of l.

6 Claims, N0 Drawings GASOLINE BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to improved gasolines having good anti-icing, anti-rust, anti-stalling, detergent and water interaction properties.

2. Description of the Prior Art In the operation of spark ignition internal combustion engines, as in motor vehicle uses, numerous operational difficulties may preclude trouble-free operation. One difficulty is encountered when an internal combustion engine is operated under cool, humid atmospheric conditions, especially when the fuel is a winter grade gasoline having a 50 percent ASTM distillation point of 220F. or below. Under such conditions engine stalling may occur at idling speeds during the warm-up period, particularly when such idling follows a period of light load. Generally, too, the above type of stalling occurs when the atmospheric relative humidity is greater than about 65% and the ambient temperature is in the range 30-60F. Such conditions are conducive to the deposition of ice on the throttle plate and on the adjacent carburetor walls so that, when idling with the throttle plate substantially closed, the ice deposits restrict air intake and cause stalling.

Engine stalling may also be encountered by the accumulation of deposits other than ice in the carburetor, for example, on the throttle plate and on the surrounding walls. These deposits are believed to be derived from contaminants in the fuel and in the air, including the fumes vented from the engine crankcase. The accumulation of deposits around the throttle plate results in rough idling and frequent stalling. In contrast to stalling caused by icing, which difficulty is usually eliminated when the engine warms up sufficiently to melt the ice, the difficulty caused by the non-ice deposits is more permanentv Corrective measures include costly carburetor cleaning or increasing the idling speed; the latter results in greater difficulty in handling the vehicle and loss of fuel.

The engines in the automotive vehicles presently being produced may provide additional problems, particularly during the engine warm-up periods, which problems may be manifested as frequent engine stalling, rough idling and hesitation. Such problems are generally recognized as consequences of the various engine modifications and the added devices designed to control exhaust emissions of hydrocarbons, carbon monoxide and oxides of nitrogen. These difficulties may be compounded by the aforesaid operational difficulties brought about by the accumulation of ice and other deposits in the carburetor.

Since motor fuels are unavoidably contacted with water and ferrous metal surfaces during processing, transportation, storage and use, the inclusion of an effective corrosion inhibitor in the fuel is considered essential. Another essential requirement of a commercially acceptable motor fuel additive is that it not interfere with the separation of the fuel from any aqueous phase with which it may come in contact. Moreover, such contacts with water should not lead to extraction of any additive from the fuel or emulsification of water into the motor fuel phase. The presence of appreciable amounts of internal water in the fuel is undesirable because of its corrosive effect on metal engine parts and 2 because of the possibility of its forming ice crystals in cold weather.

For simplified handling and economy the desired properties in gasoline should be provided with a minimum number of additives which are effective in small amounts; most desirable in a single multifunctional additive, that is, one which provides a number of properties. Although many multifunctional additives for gasoline are known in the art, they may not be commercially acceptable either because they introduce some undesirable side effects or because they must be used in excessive amounts to provide all the desired properties. Thus, for example, if an additive provides exceptional anti-icing protection at a relatively low concentration but must be used at a considerably greater concentration to provide anti-corrosion protection as well, much of the multifunctional benifit may be lost if it is more economical to add an independent, more effective corrosion inhibitor.

SUMMARY OF THE INVENTION In summary, this invention resides in a composition exhibiting good anti-stalling, anti-icing, anti-rust, detergent and water interaction properties and comprising a hydrocarbon mixture boiling in the gasoline range and an effective amount, usually 0004-00271 by weight, based on the weight of the hydrocarbon mixture, of an amine carboxylate salt of the formula 2 2 CHR c11 0) a R-c-0-NH(R (cim ca o) a wherein R is C saturated or unsaturated aliphatic hydrocarbyl, R is C saturated or unsaturated aliphatic hydrocarbyl, each of R an R is selected from H and CH each ofa and b is 1-14 and the sum of a and b is 2l5, said salt having at least two (CH- Cl-I O) groups, said composition having a Federal water rating of 1.

DETAILED DISCUSSION OF THE INVENTION As used in the context of the following description the minimum amount of amine carboxylate salt required for imparting an anti-corrosion property to the gasoline refers to the least amount of the salt which will provide satisfactory inhibition of rusting in ASTM D665 (Procedure A) test method of the American Society ofTesting Materials. By the minimum amount required to impart anti-icing protection is meant the least amount of the salt required in gasoline to provide at least 25 cycles without stalling in an anti-icing test hereinafter described. Water interaction properties de-v scribed herein are measured according to Federal Test Method Standard No. 7918 Method 3251.7, with a rating of I considered satisfactory in the context of this invention.

The amine salt, as defined above, is multifunctional in that it provides desirable anti-stalling, anti-icing, anti-corrosion and detergent properties in gasolines at low concentrations without adversely affecting the desirable water interaction properties of the gasoline, that is, good separation of the hydrocarbon phase from water is maintained. The preferred amine carboxylate salt is derived from tall oil fatty acid and a C alkyl or alkenyl amine containing about 3-7 oxyethylene groups. Most preferred is a reaction product of tall oil fatty acid and a C alkyl or alkenyl amine containing about 46 oxyethylene groups.

The amine component of the amine carboxylate salt is a tertiary monoamine of the formula 2 (can CH O) H wherein R, R R, a and b are as previously defined. Examples of the above-defined R groups include alkyl, alkenyl, alkadienyl and alkatrienyl groups, such as octyl, nonyl, decyl, decenyl, undecyl, dodecyl, tridecyl. tetradecyl. tetradecenyl, pentadecyl, hexadecyl, hexadecenyl, heptadecyl, octadecyl, octadecenyl, octadecatrienyl, nonadecyl, eicosyl, heneicosyl, docosyl, 9-phenyloctadecyl and IO-phenylocatodecyl. straight chain groups are preferred. Mixtures of R groups may be present; such mixtures may be derived from mixed amines. Useful mixed amines include those derived from certain naturally occurring fats and oils, such as coconut oil, corn oil, cottonseed oil. tallow and soybean oil. The amines prepared from tallow are ordinarily mixtures wherein the aliphatic hydrocarbyl groups are tetradecyl, tetradecenyl, hexadecyl, hexadecenyl, octadecyl, octadecenyl, octadecadienyl and eicosyl; those prepared from soybean oil are mixtures containing hexadecyl, octadecyl, octadecenyl, octadecadienyl and eicosyl groups; those prepared from cottonseed oil are mixtures ordinarily containing tetra decyl, hexadecyl, octadecyl, octadecadienyl and eicosyl groups; and those prepared from coconut oil are mixtures containing octyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, octadecenyl and octadecadienyl groups. The amines derived from naturally occurring fats and oils are commercially available and for reason of economy are preferred for the preparation of the amine carboxylate salts employed herein. Preferred R groups include alkyl and alkenyl groups of 12-18 carbon atoms.

The oxyalkylene portions of the aforesaid tertiary monoamine are produced by reacting an appropriate primary amine with an alkylene oxide under either acidic or alkaline conditions, alkaline conditons being preferred. The reaction of a primary amine and an alkylene oxide is well known in the art. In such a process a single product generally is not obtained; the product is usually characterized as having an average number of oxyalkylene groups, the average number depending upon the molar ratio of the alkylene oxide to the amine. Thus, in the context of the present invention the values of a and b in the aforesaid formula represent average values. An amine containing oxyethylene groups can be readily prepared by reacting the appropriate primary amine with the requisite amount of ethylene oxide. Amines containing both oxyethylene groups and oxypropylene groups can be readily prepared by reacting the primary amine with ethylene oxide and 1,2- propylene oxide, such reaction being carried out by condensing the primary amine initially with ethylene oxide and then further condensing the reaction product with 1,2-propylene oxide; by initially condensing the primary amine with 1,2-propylene oxide and then further condensing the reaction product with ethylene oxide; by condensing the primary amine with a mixture of ethylene oxide and propylene oxide; or by combinations of any two or more of the above sequences.

In order for a salt, as described above, to have maximum utility as a practical multifunctional additive for gasoline, that is, providing the properties of antistalling, anti-icing, anti-corrosion, detergency and good water interaction, the total number of oxyalkylene groups present should be 2l5; at least two oxyethylene groups must be present. The oxyethylene groups in the amine confer anti-corrosion and anti-icing properties on the amine carboxylates prepared therefrom; the oxopropylene groups, when present, contribute to antiicing but have little anti-corrosion effect. When only oxyethylene groups are present and when the number of oxyethylene groups is greater than about 0.7 per carbon atom of the amine R group, unfavorable water interaction properties may be obtained and the minimum amount ofthe amine carboxylate salt required for satisfactory anti-icing and anti-corrosion properties may exceed the maximum amount of the salt at which satisfactory water interaction is obtained. Oxypropylene groups are not deleterious to water interaction and, therefore, can be incorporated into the molecule to mitigate the tendency of the oxyethylene groups to adversely affect the water interaction rating. Thus. it is possible to have more oxyethylene groups than the above indicated 0.7 oxyethylene group per carbon atom of the R aliphatic hydrocarbyl group provided one or more oxypropylene groups are also present. The maximum allowable number of oxyethylene groups in combination with oxypropylene groups can be determined readily by those skilled in the art by following the teachings given herein. Preferably, the amine carboxylate salt contains 3-7 oxyethylene groups, more preferably, 46 oxyethylene groups.

The carboxylic acid component of the amine carboxylate salt employed in this invention is an aliphatic hydrocarbon monocarboxylic acid of l222 carbon atoms; the acid may be saturated or unsaturated. lncluded are dodecanoic, tridecanoic, tetradecanoic, tetradecenoic, hexadecanoic, hexadecenoic, octadecnoic, octadecenoic, octadecadienoic, eicosanoic, uneicosanoic and doeicosanoic acids. Mixed acids can be employed. Acid mixtures, such as those obtained by hydrolysis of natural fats and oils, containing alkyl, alkenyl and alkadienyl groups, such as those enumerated above for the amine mixtures from these same sources, are useful. A particularly useful and preferred acid mixture is tall oil fatty stearic, acid obtained from tall oil. Tall oil is a mixture of rosin and fatty acids released by acidulation of the black liquor soap skimmed off the black liquor from the sulfate process in the manufacture of Kraft paper. Crude tall oil is commonly fractionally distilled to provide cuts wherein the ratio of fatty acids to rosin acids varies from 1:99 to 99: 1. ln the context of this description tall oil fatty acid is intended to include tall oil compositions having a fatty acid content of at least about 50% by weight, the balance being mainly rosin acids in admixture with minor amounts of unsaponifiable materials of unknown chemical composition. The fatty acids in tall oil fatty acids consist mainly of oleic, linoleic, conjugated linoleic, palmitic, steric, palmitoleic, arachidic and behenic stearic, Tall oil fatty acids which are commercially available include those with the following compositions: palmitic (OJ-5.3%); palmitoleic (OJ-2.1%); stearic (2.l2.6%)', oleic (39.349.5%); linoleic (38.l4l.4% eicosanoic (l.2l.9%); eicosadienoic (O.53.2% eicosatrienoic (0.4-2.9%); and behenic (0.4-0.97r) acids, with the balance being rosin acids, unidentified acids and unsaponifiable materials.

The amine carboxylate salts employed in this invention are produced by reacting the above-described tertiary monoamine and the carboxylic acid. Generally, one mole of the acid is used with one mole of the amine but up to a molar excess of either the acid or the amine can be present. The reaction of the amine and the acid is that of neutralizaton, with the formation of the amine salt of the acid, and can be carried out in known manner. If desired, the reaction can be accelerated by employing slightly elevated temperatures of l00200F. Solvents, such as methanol, ethanol, isopropanol, butanol, acetone, methyl ethyl ketone chloroform, carbon tetrachloride, benzene, toluene and xylene, as well as mixtures of solvents, can be used. For ease of handling and subsequent incorporation into gasoline, the amine carboxylate salt is dissolved in a suitable solvent, such as one of those recited above. Such solutions or concentrates generally contain l090% by weight of salt, preferably 4080%. The preferred solvent is xylene.

The amine carboxylate salt is added to gasoline, that is, a mixture of hydrocarbons boiling in the gasoline boiling range. The base fuel can consist of straight chain or branched chain paraffins, cycloparaffins, olefins and aromatic compounds or any mixture of such hydrocarbons obtainable from straight run naphtha, polymer gasoline, natural gasoline, thermally or catalytically cracked hydrocarbon stocks and catalytically reformed stocks. The gasoline can also contain varying amounts of conventional fuel additives, such as antiknock compounds, including tetramethyllead, tetraethyllead and mixed alkyllead, scavenging agents, dyes, antioxidants, anti-icing agents, rust inhibitors, detergents and anti-preignition agents. Generally, the concentration of amine carboxylate salt in the gasoline is about 0.004-0.02% by weight (10 to 50 pounds per thousand barrels of gasoline), preferably 0.0060.008% by weight to pounds per thousand barrels of gasoline).

The anti-rust properties of the salts employed in this invention are determined according to the method of ASTM D-665 (Procedure A). In this test 300 ml. of the gasoline containing the additive under test is stirred with 30 ml. of distilled water at a temperature of 32C. (90F.) with a cylindrical steel specimen completely immersed therein. The test is carried out for 20 hours. With the base fuel alone the steel specimen usually has about 80% of the surface covered with rust spots after 20 hours. For the purpose of this invention and for the comparison of anti-corrosion efficiency, the minimum amount of the amine carboxylate salt required to afford substantially complete rust protection was determined.

before stalling. The test is carried out with a Chevrolet,

230 cubic inch, 6 cylinder engine. The environment of the carburetor is maintained at 40F. (4C.) and relative humidity. At these conditions essentially water saturated cool air is drawn through the carburetor. The test consists of running the engine on a two part cycle, namely, 20 seconds with open throttle at an engine speed to 1,600 r.p.m. and 10 seconds with the throttle almost closed at 400 r.p.m. (idling speed). During the test ice forms on the throttle plate and on the surrounding carburetor walls and causes the engine to stall by blocking the flow of air when the throttle plate is almost closed during the idling portion of the cycle. The base gasoline is chosen so that, normally, in the absence of an effective anti-icing additive, engine stalling occurs in about 3-5 cycles. Generally, an additive is considered effective if it prevents stalling to about 10 cycles; an excellent anti-icing agent prevents stalling to at least about 25 cycles. The base gasoline used has a 50% distillation point of 197F. (92C.) according to ASTM Method D-86. To illustrate the anti-icing efficiency of the amine carboxylate salts employed in this invention, minimum concentrations of the salts to prevent stalling to at least 25 cycles were determined. REpresentative results are tabulated in the examples which follow.

The water interaction properties (United States Federal Water Rating) of gasoline containing the amine carboxylate salts employed in this invention were determined according to Federal Test Method Standard No. 7918 Method 325l,7 wherein the gasoline containing the additive is vigorously shaken with an aqueous phosphate buffer solution (pH 7) and after standing for 5 minutes the change in volume of the aqueous phase and the condition of the interface is observed. The condition of the interface is reported in terms of the following ratings:

Rating Appearance bu k) The Federal Water Rating provides a measure of the ease of separation of the gasoline from water after vigorous mixing. It is generally considered that a rating of lb is required for a satisfactory separation involving commercial fuels. For the purpose of the present invention a rating of l was chosen as representing satisfactory water interaction properties. The maximum concentration of the amine carboxylate salt in gasoline which still provides a water rating of 1 was determined. If this maximum concentration is exceeded, water interaction is excessive in the context of this invention. The maximum concentration which provides a rating of l is important for commercially practical multifunctional gasoline additives since an additive which imparts, for example, outstanding anti-corrosion and antiicing properties, would be of little value if the maximum concentration of the additive at which a water rating of l is obtained is considerably lower than the minimum concentration required to provide effective carburetor clean. In the first test deposits are initially accumulated in the carburetor under specified conditions. The effectiveness of an additive as a carburetor detergent is then determined by operating the engine anti-corrosion and anti-icing protection. Results obwith fuel containing the additive and measuring the tained with amine carboxylate salts employed in this amount of accumulated deposit removed. invention are tabulated in the examples which follow. Chevrolet, 6 cylinder. 230 cubic inch engines having Carter No. 351 1-5 carburetors and ice tow rs with EXAMPLES 1-9 j j y L heaters were used. One engine was used to produce. in These examples illustrate the multifunctional activithe shortest time, sufficient throttle body deposit for ties of the amine carboxylate salts employed in this inthe cleanup phase of the test. Since the deposit accu vention. The salts were prepared by mixing a molar mulation phase of the test is carried out o\er a period equivalent amount of the amine with a molar equivaof about 10 hours and the clean-up phase ofthe test relent amount of tall oil fatty acid. The amines are desigquires about 50 hours, by utilizing one engine for denated in Table l in terms of the initial amine followed posit accumulation and several engines for the clean-up by the number of oxyalkylene groups incorporated, portion of the test the testing may be accomplished in ether ethylene oxide (E0) or propylene oxide (PO). a relatively short time. ln the deposit accumulation en Thus. in Example I, the initial amine is cocoamine, a gine the ring gap of the top piston ring was increased mixture of amines derived from coconut oil, into which by 0.125 inch (0.32 cm.) to 0. l 38 inch (0.35 cm.) and an average of2 units of ethylene oxide have been incorthe ring was installed in place of the second compresporated. The tall oil fatty acid is a commercially availsion ring, leaving the top ring groove empty and thus able composition containing 44% oleic acid, 32% nonincreasing the blowby. The total blowby was directed conjugated linoleic acid, 8% conjugated linoleic acid, to the carburetor air cleaner from the dome cover. The 5% saturated acid (palmitic and stearic) and 11% uniair cleaner element was eliminated. The exhaust line dentifred acids and unsaponifiable material. Additive was modified to supply engine exhaust to the carbureconcentrations are given in the table in terms of 72 by tor air cleaner. The engine was operated under the folweight and pounds per thousand barrels (PTB). lowing conditions: the distributor vacuum advance was TABLE l Anti-rust Anti-icing lall ()il Fatty (oncn for (ASTM [16651 Conch. l Acid ('urhoxylatc Federal Water ('onc'n to Proudc No of Rating of l for 0' Rust 15 Cycles Wt PlB Wt. w PTB vii P18 (oeoamlnc 2E0 0.02 50 0.008 20 0006 I5 I l irllouammc 2E0 002 50 0.006 [5 0009 22, 3 ()lcylammc 5E0 0 008 20 0.006 15 0 006 I5 4 lallouammc 5E0 0 0| 2 0.006 15 0 00K 20 5 Stearylamme 5F() 0 008 20 0.006 15 0 008 20 h Phenylslearyl- 0 02 0.006 l5 0 011 30 amine 5E0 A l.lll\ .lllllnc l5l-'() onus rs (mun I5 u out I 7 Z-l-thylhuylamrne 2H) 0.03 250 0,012 30 0 02 530 K ('ocoamlne (ZPUZEO) 0.02 250 0,0l2 S30 00: S30 9 ('ocoamme (|0P() 5P0] 0.02 250 0,012 30 0 02 530 le than 2 Uqual In or greater than 5 equal to in IL'\\ than The above results show that the amine carboxylate eliminated to maintain spark advance of 4 before top salts provide outstanding corrosion and icing protec- 50 center; engine speed at 700 i 10 r.p.m.; water outlet tion at very low concentrations. The results also show temperature I: 2.5F. (79: l.5C.); air/fuel mixthat water interaction (Federal Water Rating of l) is ture at maximum vacuum; carburetor air cooled by good at the minimum concentrations to provide antipassage through an ice tower and then reheated to rust and anti-icing protection. Comparative Example A -95F. (32-35C.); and engine exhaust supplied to shows that when the number of ethylene oxide groups 55 carburetor air inlet as described below. The fuel used is greater than about 0.7 per carbon atom of the amine R group, poor Federal Water Rating is obtained even though anti-rust and anti-icing properties are satisfactory.

EXAMPLE 10 The usefulness of the amine carboxylate salts employed in this invention as carburetor detergents is demonstrated by two series of tests. The first test measures the effectiveness of the salts in removing deposits already present in the carburetor. The second test measures the effectiveness of the salts in keeping the was MS-OS, an industry standard fuel used for Sequence MS oil testing.

The engine was started with the exhaust feed valve to engine inlet air closed. The speed was adjusted to 700 r.p.m. at maximum vacuum. The exhaust feed valve was opened and the engine speed was maintained at 700 r.p.m. (the exhaust feed valve setting is critical). The setting was such as to feed the maximum amount of exhaust that the engine would accept and still operate smoothly without stalling. The engine was operated for about 10 hours or until it could no longer be kept running under these conditions. The carburetor was removed and rated using a visual rating chart. A rating of I is considered as clean. If a rating cleaner than 30 is obtained. additional deposit accumulation is required.

For the clean-up phase of the test, the dirty carburetor was installed in another engine and the operating conditions described above were used except that normal piston rings were used and the blowby and exhuast were not fed into the air inlet. Before the test new spark plugs were installed, SAE 30 low detergent oil was placed in the crankcase and the air cleaner housing and exhaust system were cleaned. The clean-up procedure was carried out for 50 hours in five lO-hr. segments, the ratings beng made at appropriate intervals to determine the amount and speed of clean-up. The percent cleanup was determined according to the following formula wherein R,, is the carburetor rating after deposit accumulation and R,, is the carburetor rating after clean-up.

The second test. the carburetor keep-clean test (Onan is carried out in a single cylinder engine to which a controlled amount of exhaust gas from another engine is mixed with air supplied to the test carburetor. THe test carburetor throat consists ofa two piece stainless steel liner fitted around the throttle plate shaft. The liner is easily removed for inspection and rating. The

engine is operated under cycling conditions of one min- The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. Composition exhibitng good anti-stalling, antiicing, anti-rust, detergent and water interaction properties and comprising a hydrocarbon mixture boiling in the gasoline range and 0.0040.02% by weight, based on the weight of the hydrocarbon mixture, of an amine carboxylate salt of the formula .9 CHIR CH 0) H R-C-O-NH(R (caR cH 0) H wherein R is C saturated or unsaturated aliphatic hydrocarbyl, R is C saturated or unsaturated aliwherein R is C saturated or unsaturated aliphatic hydrocarbyl, R is C saturated or unsaturated aliphatic hydrocarbyl, each of R and R is selected from The above results show that the amine carboxylate salts employed in this invention are also effective as a carburetor detergent, not only inhibiting deposit formation but removing deposits already present. The carburetor detergency activity is demonstrated at the concentration level found to be effective for anti-corrosion and anti-icing protection as shown in Table I. Table II also shows that neither the amine nor the carboxylic acid component of the amine carboxylate salt is as effective as the salt as a carburetor detergent at the same molar concentraton. Thus, oleylamine 5E0 increases the Onan rating l.6 over the control fuel (Run 2) and tall oil fatty acid increases the Onan rating 1.4 (Run 3) over the control fuel whereas the amine salt produced from the amine and the carboxylic acid increases the rating by 4.2 (Run 4) which is 1.2 units greater than the expected rating increase of 3.0.

represents the acyl moiety of tall oil fatty acid.

6. Additive of claim 4 wherein R is C n-alkyl or nalkenyl and the sum of a and b is 4-6.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2862800 *Nov 6, 1956Dec 2, 1958Gulf Oil CorpGasoline fuels
US2902353 *Jun 29, 1956Sep 1, 1959Socony Mobil Oil Co IncAnti-stall gasoline
US2906613 *Jun 21, 1956Sep 29, 1959Sun Oil CoSuppression of fuel icing
US3429673 *Mar 14, 1967Feb 25, 1969Henkel & Cie GmbhCorrosion inhibiting additive compositions for fuel oils
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US4010007 *May 14, 1975Mar 1, 1977Rohm And Haas CompanyThermally labile rust inhibitors
US5248315 *Feb 26, 1993Sep 28, 1993Euron S.P.A.Detergent additive for fuels
US5968211 *May 26, 1998Oct 19, 1999Exxon Research And Engineering Co.Gasoline additive concentrate
US6277158Sep 11, 1997Aug 21, 2001Exxon Research And Engineering CompanyAdditive concentrate for fuel compositions
US7402185Mar 26, 2003Jul 22, 2008Afton Chemical Intangibles, LlcAdditives for fuel compositions to reduce formation of combustion chamber deposits
US7435272 *Apr 22, 2003Oct 14, 2008Afton Chemical IntangiblesFriction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof
US7846224Dec 19, 2006Dec 7, 2010Afton Chemical Intangibles, LlcMethods to improve the low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers
US8343901Oct 12, 2010Jan 1, 2013Chevron Oronite Company LlcLubricating composition containing multifunctional hydroxylated amine salt of a hindered phenolic acid
US20030159340 *Feb 12, 2003Aug 28, 2003Clayton Christopher WilliamGasoline compositions
US20040010966 *Mar 26, 2003Jan 22, 2004Aradi Allen A.Additives for fuel compositions to reduce formation of combustion chamber deposits
US20040010967 *Apr 22, 2003Jan 22, 2004Aradi Allen A.Friction modifier alkoxyamine salts of carboxylic acids as additives for fuel compositions and methods of use thereof
US20070094921 *Dec 19, 2006May 3, 2007William ColucciMethods to improve the low temperature compatibility of amide friction modifiers in fuels and amide friction modifiers
EP0117108A2 *Feb 13, 1984Aug 29, 1984Nippon Oil And Fats Company, LimitedMethod for improving cold flow of fuel oils
EP0117108A3 *Feb 13, 1984Nov 7, 1984Nippon Oil And Fats Company, LimitedMethod for improving cold flow of fuel oils
EP0237356A2 *Mar 13, 1987Sep 16, 1987Exxon Research And Engineering CompanyImproved fuel composition for multi-port fuel injection systems, and use thereof.
EP0237356A3 *Mar 13, 1987Jan 7, 1988Exxon Research And Engineering CompanyImproved fuel composition for multi-port fuel injection systems, and additive concentrates therefor
EP0707058A1Sep 15, 1995Apr 17, 1996AGIP PETROLI S.p.A.Fuel composition
EP1462506A1 *Jul 30, 2003Sep 29, 2004Ethyl CorporationAdditives for fuel compositions to reduce formation of combustion chamber deposits
WO1996021709A1 *Jan 9, 1996Jul 18, 1996Exxon Chemical Patents Inc.Fuel compositions
WO2003068895A1 *Feb 11, 2003Aug 21, 2003Shell Internationale Research Maatschappij B.V.Gasolinen compositions
WO2012051075A2Oct 7, 2011Apr 19, 2012Chevron Oronite Company LlcLubricating composition containing multifunctional borated hydroxylated amine salt of a hindered phenolic acid
Classifications
U.S. Classification44/408, 252/392
International ClassificationC10L1/222
Cooperative ClassificationC10L1/2225
European ClassificationC10L1/222B2