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Publication numberUS3024195 A
Publication typeGrant
Publication dateMar 6, 1962
Filing dateAug 24, 1959
Priority dateAug 24, 1959
Also published asUS3024237
Publication numberUS 3024195 A, US 3024195A, US-A-3024195, US3024195 A, US3024195A
InventorsRobert G Anderson, Alan Y Drummond, Frank A Stuart
Original AssigneeCalifornia Research Corp
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Lubricating oil compositions of alkylpiperazine alkenyl succinimides
US 3024195 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United State 3,024,195 Patented Mar. 6, 1932 3,024,195 LUBRICATING OIL COMPGSKTHONS F ALKYL- PIPERAZINE ALKENYL SUCCINIMIDES Alan Y. Drummond, Richmond, Robert G. Anderson, Novato, and Frank A. Stuart, Orinda, Calif, assignors to California Research Corporation, San Francisco, Calif., a corporation of Delaware N0 Drawing. Filed Aug. 24, 1959, er. No. 835,391 9 Claims. (Cl. 252-51.5)

This invention pertains to lubricating oil compositions having incorporated therein metal-free detergents. These particular metal-free detergents are N-substituted alkenyl succinimides.

Alkenyl succinic anhydrides and numerous derivatives thereof are well known in the art. For example, alkenyl succinic anhydrides in which the alkenyl radical contains from to 20 carbon atoms are taught as corrosion inhibitors in lubricating oil compositions. Also, products obtained by reacting such alkenyl succinic acid anhydrides with non-cyclic monamines are taught as ferrous corrosion inhibitors for lubricating oil compositions.

However, the above known alkenyl succinimides are not useful as detergents in lubricating oil compositions. In contrast thereto, the N-substituted polyamine alkenyl succinimides which are described herein are new compounds which are useful as detergents in lubricating oil compositions.

Present day internal combustion engines operate at high speeds and high compression ratios. When used in the so-called city stop-and-go driving, which includes the greater part of the driving condition for a large percentage of todays automobiles, the internal combustion engines do not reach the most efficient operating temperature. Under city driving conditions, large amounts of partial oxidation products are formed, and reach the crankcase of the engine by blowing past the piston rings. Most of these partial oxidation products are oil insoluble, tending to form deposits on the various operating parts of the engine, such as the pistons, piston rings, etc. For the purpose of preventing the deposition of these products on the various engine parts, it is necessary to incorporate detergents in the lubricating oil compositions, thus keeping these polymeric products highly dispersed in a condition unfavorable for deposition on metals.

For the most part, the various detergents which are added to crankcase oils to reduce this formation of sludges and varnishes are metal organic compounds, particularly those compounds wherein the metal is linked to an organic group through an oxygen atom. Although these metal-containing organic compounds have some effectiveness as detergents for dispersing the precursors of deposits within the oil itself rather than permitting them to form added deposits on the engine parts, they have the disadvantage of forming ash deposits in the engine. These ash deposits lower engine performance 2 by fouling spark plugs and valves, and contributing to preignition.

It is a particular object of this invention to provide lubricating oil compositions which are compounded with a metal-free detergent.

Therefore, in accordance with this invention, it has been discovered that lubricating oil compositions particularly useful for heavy duty service are obtained by incorporating N-alkylpiperazine monoalkenyl succinimides in oils of lubricating viscosity.

By the use of lubricating oil compositions containing the N-substituted alkenyl succinimides described herein, diesel and gasoline engine parts remain remarkably free of deposits and varnish, even under severe operating conditions.

The N-alkylpiperazine monoalkenyl succinimides are new compounds of the formula:

wherein R is a hydrocarbon radical having a molecular weight from about 400 to about 3000; that is, R is a hydrocarbon radical containing about 30 to about 200 carbon atoms; R is a hydrocarbon radical containing from 1 to 3 carbon atoms; and R" is hydrogen or a hydrocarbon radical containing from 1 to 3 carbon atoms.

These N-substituted alkenyl succinimides can be prepared by reacting maleic anhydride with an olefinic hydrocarbon followed by reacting the resulting alkenyl succinic anhydride with an N-(p-aminoalkyl) piperazine. Such N-(B-aminoalkyl) piperazines are exemplified by N-methyl-N-(fi-aminoethyl) piperazine, N-isopropyl-N'- (fiaminoethyl) piperazine, N-(B-aminoisopropyl) piperazine, etc.

The R radical of the above formula, that is, the alkenyl radical, is derived from an olefin containing from 2 to 5 carbon atoms. Thus, the alkenyl radical is obtained by polymerizing an olefin containing from 2 to 5 carbon atoms to form a hydrocarbon having a molecular weight ranging from about 400 to about 3000, more preferably, 900 to 1200. Such olefins are exemplified by ethylene, propylene, l-butene, Z-butene, isobutene, and mixtures thereof. Since the methods of polymerizing the olefins to form polymers thereof is immaterial in the formation of the new compound described herein, any of the numerous processes available can be used therefor.

The preparation of N-substituted monoalkenyl succinimides derived from amine derivatives of piperazine can be described generally by the following equations, using a polymer of isobutene as an example of the alkenyl radical; and N-(fi-aminoethyl) piperazine as an example of an N-(aminoalkyl) piperazine:

wherein n has a value of about 7 to about 50.

The above reaction between a polyolefin and maleic anhydride is an uncatalyzed addition reaction which should not be confused with a copolymerization reaction such as that obtained with a vinyl monomer and maleic anhydride. While the general reaction of an olefin and maleic anhydride is well known for olefins of low molecular weight (e.g., olefin-s of 18 carbon atoms), no previous work has been done with maleic anhydride and the high molecular weight olefins as described herein.

The reaction set forth and described by Equation I hereinabove can proceed in a mol ratio of the polyolefin to the maleic anhydride of 1:1 to 1:10, preferably from 1: 1 to 1:5. The reaction temperature can vary from 300 F. to 450 F. Because of the greater yield of products obtained thereby, it is preferred to use the high range of temperatures (e.g., 375 to 450 F.).

In the second step of the reaction as exemplified by Equation II hereinabove, the yield of the imide is extremely high even though the reactants are used in equal molor ratios.

The reaction described by Equation II hereinabove can be made at 220 F. to 500 F., preferably from 300 F. to 400 F. The alkenyl succinic anhydride and the N-alkylaminepiperazines are reacted in about equal molar quantities.

Since the reaction between the polyolefin and maleic anhydride may not go to completion, the resulting alkenylsuccinic anhydride may contain some unreacted polyolefin. As it may not be desirable to separate out this unreacted polyolefin at this stage, the resulting imide formed by reaction of the alkenyl succinic anhydride and the diamine will contain this polyolefin as an impurity which can be a diluent in the formation of lubricating oil compositions. However, if it is so desired, this unreacted polyolefin' can be removed by precipitation, for example, by acetone or methanol from a hydrocarbon solution.

Lubricating oils which can be used as base oils include a wide variety of lubricating oils, such as naphthenic base, paraifin base, and mixed base lubricating oils, other hydrocarbon lubricants, e.g., lubricating oils derived from coal products, and synthetic oils, e.g., alkylene poly- .mers (such as polymers of propylene, butylene, etc., and the mixtures thereof), alkylene oxide-type polymers (e.g., propylene oxide polymers) and derivatives, including alkylene oxide polymers prepared by polymerizing the alkylene oxide in the presence of water or alcohols, e.g'., ethyl alcohol, dicarboxylic acid esters (such as those which are prepared by esterifying such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkanol succinic acid, furnaric acid, maleic acid, etc., with alcohols such as butyl alcohol, hexyl alcohol, 2-ethyl hexyl alcohol, dodecyl alcohol, etc.), liquid esters of acids of phosphorus, alkyl benzenes (e.g., monoalkyl benzene such as dodecyl benzene, tetradecyl benzene, etc., and dialkyl benzenes (e.g., nnonyl 2-ethyl hexyl benzene); polyphenyls (e.g., biphenyls and terphenyls), alkyl biphenyl ethers, polymers of silicon (e.g., tetraethyl silicate, tetrai-sopropyl silicates, tetra-(4-methyl-2-tetraethyl) silicate, hexyl (4-methyl-2-pentoxy) disiloxane, poly(rnethyl) siloxane, poly(methylphenyl) siloxane, etc. Synthetic oils of the alkylene oxide-type polymers which may be used include those exemplified by the alkylene oxide polymers.

The above base oils may be used individually or in combinations thereof, wherever miscible or Wherever made so by the use of mutual solvents.

The above-described alkenyl succinimides of this in vention can be used in oils of lubricating viscosity in amounts of 0.1% to by weight, preferably 0.25% to 5%, by weight.

The preparation of N-alkylpiperazine alkenyl succinimides is illustrated in the following examples.

EXAMPLE I.-PREPAR ATION OF POLYBUTENYL SUCCINIC ANHYDRIDE A mixture of 1000 grams (1 mol) of a polybutene having a molecular Weight of about 1000 and 98 grams (1 mol) of maleic anhydride was heated at 410 F. in a nitrogen atmosphere with agitation for a period of 24 hours. The reaction mixture was cooled to 150 F. and 700 cc. of hexane added; after which the mixture was filtered under vacuum. After vacuum distillation to remove the hexane from the filtrate, the product was maintained at 350 F. atan absolute pressure of 10 mm. Hg for one hour to remove traces of maleic anhydride. The crude polybutenyl succinic anhydride thus prepared had a saponification number of 79.

EXAMPLE lI.-PREPARATION OF N-ETHYLPIPER- AZINE POLYBUTENYL SUCCINIMIDE ANHY- DRIDE A mixture of 18 grams (0.14 mol) of N-(fl-aminoethyl) piperazine and 200 grams (0.127 mol) of the polybutenyl succinic anhydride of Example I hereinabove was blended with agitation in a nitrogen atmosphere. The mixture was heated at 500 F. for one hour, after which the absolute pressure was reduced to about 200 mm. Hg to facilitate the removal of water and unreacted piperazine. The reaction mixture was then allowed to reach room temperature at this reduced pressure. The reaction product contained 2.59% nitrogen (theory=2.67%). Infrared analysis showed that the reaction product was an imide containing a polybutene side chain.

Table I hereinbelow presents data obtained with lubricating oil compositions containing N-alkylpiperazine monoalkenyl succinimides.

The tests were made in a Caterpillar L-1 engine according to MilL-2104 conditions for a period of .120 hours as described in the Coordinating Research Council Handbook, January 1946.

The PD Nos. refer to the piston discoloration rating. After the engine test, the three piston lands are examined visually. To a piston skirt which is completely black is assigned a PD number of 800; to one which is completely clean, a PD number of 0; to those intermediate between completely black and completely clean are assigned PD numbers intermediate in proportion to the extent and degree of darkening.

The GD Nos. refer to the percentage deposits in the piston ring grooves; and 0 evaluation being a clean groove; and a number of being a groove full of deposits.

The base oils were California SAE 30 base oils.

Table I Additive A B C Sueclnimide, weight percent 0. 1.0 1.0 Dithiophosphate;mM./kg 0. 0 0. 0 12 st Results:

GD N o 39 1 0.3 PD N0 800, 800, 800 25, 0, 5 10, 0, 0

Table II hereinbelow presents data obtained in an FL2 test, using a 6-cylinder Chevrolet engine operating at 2500 r.p.m. for a period of 40 hours, which test is fully described in a Coordinating Research Council bulletin titled Research Technique for the Determination of the Elfects of Fuels and Lubricants on the Formation of Deposits During Moderate Temperature Operation (1948).

The piston varnish rating is a visual observation of the amount of varnish on a piston skirt, with 10 being the maximum rating for a perfectly clean piston and a 0 being the rating of a piston fully covered with black varnish. This piston varnish rating correlates with road performance in automobiles.

The base oil was an SAE 30 base oil.

The succinimide and the dithiophosphate were the same as those described for Table I hereinabove.

It is readily seen from the data set forth hereinabove in Tables I and -II that lubricating oil compositions containing the N-alkylpiperazine alkenyl succinimides as described herein are superior as lubricating oil compositions for the lubricating of internal combustion engines.

vIn addition to the dithiophosphate described hereinabove, lubricating oil compositions containing the N-substituted alkenyl succinimides of N-alkylpiperazine of this invention may also contain other detergents, viscosity index improving agents, rust inhibitors, oiliness agents, grease thickening agents, etc.

We claim:

1. A lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to 80%, by Weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:

wherein R is a hydrocarbon radical having a molecular weight from about 400 to about 3000, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.

2. A lubricating oil composition consisting essentially of an oil of lubricating viscosity and from 0.1% to by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:

wherein R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R' is a hydrocarbon radical containing from 1 to 3 carbon atoms.

3. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and firom 0.25 to 5%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:

wherein R is a hydrocarbon radical having a molecular weight from about 900 to about 1200, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms, and R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.

4. A lubricating oil composition comprising a major proportion of a petroleum lubricating oil and from 0.25% to 5%, by weight, of an N-substituted monoalkenyl succinimide of the formula:

CH; CH;

CHz-CH: CHa/n CHICHQN NH GHQ-T"? CHPCHI wherein n has a value of about 7 to about 5 0.

5. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, in an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinim ide of the formula:

wherein R is a hydrocarbon radical having a molecular weight from about 400 to about 3,000, R is a hydrocarbon radical containing from one to three carbon atoms, and R" is selected from the group consisting of hydrogen and hydrocarbon radicals containing from 1 to 3 carbon atoms.

6. A lubricating oil composition comprising a major proportion of an oil of lubricating viscosity and a minor proportion, an amount sufiicient to impart detergency to said oil, of an N-alkylpiperazine monoalkenyl succinimide of the formula:

wherein R is a hydrocarbon radical containing from about 30 to about 200 carbon atoms formed by polymerizing olefins containing from 2 to 5 carbon atoms, and R is a hydrocarbon radical containing from 1 to 3 carbon atoms.

7. A lubricating oil composition consisting essentially of an oil of lubricating viscosity and from about 0.1% to about 80%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:

wherein R is an aleknyl radical containing from 30 to 200 carbon atoms and which is a polymer of an olefin containing from 2 to 5 carbon atoms, and R is an alkyl radical containing from 1 to 3 carbon atoms.

8. A lubricating oil composition comprising a" major C II;

proportion of an oil of lubricating viscosity and from 0.25% to 5%, by weight, of an N-alkylpiperazine monoalkenyl succinimide of the formula:

wherein n has a value of about 7 to about 50.

References Cited in thefile of this patent UNITED STATES PATENTS 2,490,744 Trigg et al Dec. 6, 1949 2,604,451 Rocchini July 22, 1952 2,638,450 White et a1 May 12, 19 52 UNITED STATES PATENT OFFICE CERTIFICATION OF CORRECTION Patent No. 3,024,195 March a, 1962 Alan Y. Drummond et a1.

It is hereby certified that error appears in the above numbered patent requiring correction and that the said Letters Patent should read as corrected below.

Columns 1 and 2, bottom of the page, the front end portion of the reactant and the reaction product of the equations, and the top of column 3, two occurrences, should appear as shown below instead of as in the patent:

H CH3 n column 2, lines 18 to 24, column 5, lines 69 to 75, column 6, lines 8 to 13, lines 21 to 27, lines 49 to 55, lines 67 to 73, column '7, lines 7 to 13, and column 8, lines 4 to 9,

the left-hand portion of the formula, each occurrence, should appear as shown below instead of as in the patent:

SEAL) ittest:

IRNEST W. SWIDER lttesting Officer DAVID L. LADD Commissioner of Patents

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2490744 *Feb 8, 1947Dec 6, 1949Socony Vacuum Oil Co IncAntirust agent
US2604451 *Sep 16, 1948Jul 22, 1952Gulf Research Development CoMineral oil compositions
US2638450 *Jan 17, 1950May 12, 1953Socony Vacuum Oil Co IncReaction products of nu-alkylated polyalkylenepolyamines and alkenyl succinic acid anhydrides
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3154560 *Dec 4, 1961Oct 27, 1964Monsanto CoNu, nu'-azaalkylene-bis
US3172856 *Sep 14, 1961Mar 9, 1965 Copolymers of n-alkyl piperazine acry- late and alkyl acrylate and lubricat- ing oils containing them
US3184474 *Sep 5, 1962May 18, 1965Exxon Research Engineering CoReaction product of alkenyl succinic acid or anhydride with polyamine and polyhydricmaterial
US3185704 *Sep 4, 1962May 25, 1965Exxon Research Engineering CoFormamide of mono-alkenyl succinimide
US3194812 *Aug 31, 1962Jul 13, 1965Lubrizol CorpHigh molecular weight alkenyl-n-para amino-phenyl succinimide
US3194813 *Oct 18, 1962Jul 13, 1965Lubrizol CorpHigh molecular weight alkenyl-n-omega amino hexylsuccinimide
US3194814 *Oct 18, 1962Jul 13, 1965Lubrizol CorpHigh molecular weight alkenyl-n-allyl succinimide
US3200075 *Feb 19, 1963Aug 10, 1965California Research CorpLactone amides in lubricating oils
US3200076 *Mar 28, 1963Aug 10, 1965California Research CorpPolypiperazinyl succinimides in lubricating oils
US3219666 *Jul 21, 1961Nov 23, 1965 Derivatives of succinic acids and nitrogen compounds
US3223625 *Nov 12, 1963Dec 14, 1965Exxon Research Engineering CoColloidal molybdenum complexes and their preparation
US3224968 *Dec 3, 1962Dec 21, 1965Ethyl CorpLubricating oil compositions
US3224975 *Dec 3, 1962Dec 21, 1965Ethyl CorpLubricating oil compositions
US3272746 *Nov 22, 1965Sep 13, 1966Lubrizol CorpLubricating composition containing an acylated nitrogen compound
US3278550 *Mar 2, 1964Oct 11, 1966Lubrizol CorpReaction products of a hydrocarbonsubstituted succinic acid-producing compound, an amine and an alkenyl cyanide
US3307928 *Jan 30, 1963Mar 7, 1967Exxon Research Engineering CoGasoline additives for enhancing engine cleanliness
US3311558 *Nov 24, 1964Mar 28, 1967Rohm & HaasN-alkylmorpholinone esters of alkenylsuccinic anhydrides
US3312619 *Oct 14, 1963Apr 4, 1967Monsanto Co2-substituted imidazolidines and their lubricant compositions
US3367943 *Nov 1, 1963Feb 6, 1968Exxon Research Engineering CoProcess for preparing oil soluble additives which comprises reacting a c2 to c5 alkylene oxide with (a) reaction product of an alkenylsuccinic anhydride and an aliphaticpolyamine (b) reaction product of alkenylsuccinic anhydride, a c1 to c30 aliphatic hydrocarbon carboxylic acid and an aliphatic polyamine
US3389083 *Jan 26, 1967Jun 18, 1968Chevron ResLubricants containing alkali metal dithiophosphates
US3424684 *Mar 10, 1967Jan 28, 1969Texaco IncLubricant containing polymeric product of alkenyl succinic anhydride and hydroxy containing piperazine derivative
US3426738 *Oct 16, 1967Feb 11, 1969Chevron ResMethod of operation and lubricant for closed emission internal combustion engines
US3449249 *May 8, 1964Jun 10, 1969Shell Oil CoLubricant compositions
US3502677 *Jun 17, 1963Mar 24, 1970Lubrizol CorpNitrogen-containing and phosphorus-containing succinic derivatives
US4465606 *Jul 22, 1982Aug 14, 1984Union Oil Company Of CaliforniaStabilization of hydrocarbon oil
US4471091 *Aug 9, 1982Sep 11, 1984The Lubrizol CorporationCombinations of carboxylic acylating agents substituted with olefin polymers of high and low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4486573 *Aug 9, 1982Dec 4, 1984The Lubrizol CorporationCarboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4489194 *Aug 9, 1982Dec 18, 1984The Lubrizol CorporationCarboxylic acylating agents substituted with olefin polymers of high/low molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4559155 *Mar 12, 1985Dec 17, 1985The Lubrizol CorporationHydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4564460 *Aug 9, 1982Jan 14, 1986The Lubrizol CorporationHydrocarbyl-substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4575526 *Mar 12, 1985Mar 11, 1986The Lubrizol CorporationHydrocarbyl substituted carboxylic acylaging agent derivative containing combinations, and fuels containing same
US4596663 *Oct 19, 1984Jun 24, 1986The Lubrizol CorporationCarboxylic acylating agents substituted with olefin polymers of high molecular weight mono-olefins, derivatives thereof, and fuels and lubricants containing same
US4613342 *Oct 16, 1985Sep 23, 1986The Lubrizol CorporationHydrocarbyl substituted carboxylic acylating agent derivative containing combinations, and fuels containing same
US4749505 *Jul 8, 1985Jun 7, 1988Exxon Chemical Patents Inc.Olefin polymer viscosity index improver additive useful in oil compositions
US4824884 *Aug 12, 1987Apr 25, 1989Pennwalt CorporationCyclic anhydride derivatives of hydrazide functionalized hindered amine light stabilizers
US4946612 *May 29, 1987Aug 7, 1990Idemitsu Kosan Company LimitedLubricating oil composition for sliding surface and for metallic working and method for lubrication of machine tools using said composition
US5041622 *Nov 28, 1990Aug 20, 1991The Lubrizol CorporationThree-step process for making substituted carboxylic acids and derivatives thereof
US5171466 *Apr 19, 1991Dec 15, 1992Ethyl Petroleum Additives LimitedSuccinimide compositions
US5232616 *Aug 21, 1990Aug 3, 1993Chevron Research And Technology CompanyLubricating compositions
US5330667 *Apr 15, 1992Jul 19, 1994Exxon Chemical Patents Inc.Two-cycle oil additive
US5356552 *Oct 12, 1993Oct 18, 1994Chevron Research And Technology Company, A Division Of Chevron U.S.A. Inc.Chlorine-free lubricating oils having modified high molecular weight succinimides
US5478367 *Oct 11, 1991Dec 26, 1995Exxon Chemical Patents Inc.Fuel oil compositions
US6294506Jul 15, 1994Sep 25, 2001Chevron Chemical CompanyLubricating oils having carbonated sulfurized metal alkyl phenates and carbonated metal alkyl aryl sulfonates
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