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Patent US5856524 - Process for preparing compositions useful as intermediates for preparing ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inAdvanced Patent SearchPatentsA process for preparing compounds useful as intermediates used for preparing lubricant and fuel additives. The intermediates include the products prepared by the process and dilactones....http://www.google.com/patents/US5856524?utm_source=gb-gplus-sharePatent US5856524 - Process for preparing compositions useful as intermediates for preparing lubricating oil and fuel additivesAdvanced Patent SearchPublication numberUS5856524 APublication typeGrantApplication numberUS 08/993,816Publication dateJan 5, 1999Filing dateDec 18, 1997Priority dateAug 22, 1995Fee statusLapsedAlso published asCA2183612A1, DE69611011D1, DE69611011T2, EP0759435A2, EP0759435A3, EP0759435B1, US5739356, US5786490Publication number08993816, 993816, US 5856524 A, US 5856524A, US-A-5856524, US5856524 A, US5856524AInventorsPaul E. Adams, Mark R. Baker, Jeffery G. DietzOriginal AssigneeThe Lubrizol CorporationExport CitationBiBTeX, EndNote, RefManPatent Citations (14), Non-Patent Citations (16), Referenced by (14), Classifications (58), Legal Events (5) External Links: USPTO, USPTO Assignment, EspacenetProcess for preparing compositions useful as intermediates for preparing lubricating oil and fuel additivesUS 5856524 AAbstract A process for preparing compounds useful as intermediates used for preparing lubricant and fuel additives. The intermediates include the products prepared by the process and dilactones.
What is claimed is: 1. A composition comprising compounds of the formula ##STR13## wherein n=0; y=0 or 1; wherein X is a divalent hydrocarbyl group selected from the group consisting of ##STR14## when y=0, and ##STR15## when y=1 wherein R.sup.1 is H or a hydrocarbon based group;each R.sup.3 is independently H or hydrocarbyl; each R.sup.4 is independently a divalent hydrocarbylene group; R.sup.5 is H or hydrocarbyl; each of R.sup.6, R.sup.7 and R.sup.8 is independently H or a hydrocarbon based group, and T is --OH. 2. The composition of claim 1 wherein each of R.sup.1 and R.sup.3 is independently H or a lower alkyl or alkenyl group.
3. The composition of claim 1 wherein each of R.sup.1 and R.sup.3 is H.
6. The composition of claim 1 wherein at least one of R.sup.1, R.sup.6, R.sup.7, and R.sup.8 is a hydrocarbyl group containing from about 7 to about 5000 carbon atoms.
7. The composition of claim 6 wherein R.sup.6 is an aliphatic group containing from about 10 to about 300 carbon atoms.
8. The composition of claim 7 wherein R.sup.6 contains from 30 to about 100 carbon atoms and is derived from a polymer selected from the group consisting of homopolymerized and interpolymerized C.sub.2-10 olefins.
9. The composition of claim 6 wherein at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from about 10 to about 300 carbon atoms.
10. The composition of claim 9 wherein at least one of R.sup.7 and R.sup.8 contains from about 30 to about 100 carbon atoms and is derived from a polymer selected from the group consisting of homopolymerized and interpolymerized C.sub.2-10 olefins.
15. The composition of claim 1 wherein at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from 8 to about 24 carbon atoms.
16. The composition of claim 1 wherein at least one of R.sup.7 and R.sup.8 contains from 12 to about 50 carbon atoms.
17. The composition of claim 1 wherein R.sup.6 is an aliphatic group containing from 8 to about 24 carbon atoms.
18. The composition of claim 1 wherein R.sup.6 contains from 12 to about 50 carbon atoms.
19. The composition of claim 1 wherein R.sup.1 is H or lower alkyl.
20. The composition of claim 19 wherein one of R.sup.1 and R.sup.3 is H and the other is lower alkyl.
21. The composition of claim 3 wherein R.sup.6 is an aliphatic group containing from about 8 to about 150 carbon atoms.
22. The composition of claim 1 wherein R.sup.5 is H or a lower alkyl group.
23. A composition comprising compounds of the formula ##STR18## wherein n=0; y=1; wherein X is a divalent hydrocarbyl group; ##STR19## wherein R.sup.1 is H or a hydrocarbon based group; each R.sup.3 is independently H or hydrocarbyl;each R.sup.4 is independently a divalent hydrocarbylene group; R.sup.5 is H or hydrocarbyl; each of R.sup.6, R.sup.7 and R.sup.8 is independently H or a hydrocarbon based group, and T is selected from the group consisting of --OH and R.sup.5. 24. The composition of claim 23 wherein each of R.sup.1 and R.sup.3 is independently H or a lower alkyl or alkenyl group.
25. The composition of claim 23 wherein at least one of R.sup.1, R.sup.6, R.sup.7, and R.sup.8 is a hydrocarbyl group containing from about 7 to about 5000 carbon atoms.
26. The composition of claim 25 wherein R.sup.6 is an aliphatic group containing from about 10 to about 300 carbon atoms.
27. The composition of claim 26 wherein R.sup.6 contains from 30 to about 100 carbon atoms and is derived from a polymer selected from the group consisting of homopolymerized and interpolymerized C.sub.2-10 olefins.
28. The composition of claim 25 wherein at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from about 10 to about 300 carbon atoms.
29. The composition of claim 28 wherein at least one of R.sup.7 and R.sup.8 contains from about 30 to about 100 carbon atoms and is derived from a polymer selected from the group consisting of homopolymerized and interpolymerized C.sub.2-10 olefins.
34. The composition of claim 23 wherein at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from 8 to about 24 carbon atoms.
35. The composition of claim 23 wherein at least one of R.sup.7 and R.sup.8 contains from 12 to about 50 carbon atoms.
36. The composition of claim 23 wherein R.sup.6 is an aliphatic group containing from 8 to about 24 carbon atoms.
37. The composition of claim 23 wherein R.sup.6 contains from 12 to about 50 carbon atoms.
38. The composition of claim 23 wherein R.sup.1 is H or lower alkyl.
39. The composition of claim 26 wherein R.sup.6 is an aliphatic group containing from about 8 to about 150 carbon atoms.
40. The composition of claim 23 wherein R.sup.5 is H or a lower alkyl group.
41. A composition comprising compounds of the formula ##STR20## wherein n=0; y=0 or 1; wherein X is a divalent hydrocarbyl group selected from the group consisting of ##STR21## when y=0, and ##STR22## when y=1 wherein R.sup.1 is H or a hydrocarbon based group;each R.sup.3 is independently H or hydrocarbyl; each R.sup.4 is independently a divalent hydrocarbylene group; R.sup.5 is H or hydrocarbyl; wherein R.sup.6 contains from 10 to about 300 carbon atoms; each of R.sup.7 and R.sup.8 is independently H or a hydrocarbon based group, and T is selected from the group consisting of --OH and R.sup.5. 42. The composition of claim 41 wherein each of R.sup.1 and R.sup.3 is independently H or a lower alkyl or alkenyl group.
44. The composition of claim 41 wherein each of R.sup.1 and R.sup.3 is H.
47. The composition of claim 41 wherein R.sup.6 contains from 30 to about 100 carbon atoms and is derived from a polymer selected from the group consisting of homopolymerized and interpolymerized C.sub.2-10 olefins.
51. The composition of claim 41 wherein R.sup.6 contains from 12 to about 50 carbon atoms.
52. The composition of claim 41 wherein R.sup.5 is H or a lower alkyl group.
53. A composition comprising compounds of the formula ##STR25## wherein n=0; y=0 or 1; wherein X is a divalent hydrocarbyl group selected from the group consisting of ##STR26## when y=0, and ##STR27## when y=1 wherein R.sup.1 is H or a hydrocarbon based group;each R.sup.3 is independently H or hydrocarbyl; each R.sup.4 is independently a divalent hydrocarbylene group; R.sup.5 is H or hydrocarbyl; R.sup.6 is H or a hydrocarbon based group, at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from 10 to about 300 carbon atoms, and T is selected from the group consisting of --OH and R.sup.5. 54. The composition of claim 53 wherein each of R.sup.1 and R.sup.3 is independently H or a lower alkyl or alkenyl group.
58. The composition of claim 53 wherein at least one of R.sup.7 and R.sup.8 contains from 12 to about 50 carbon atoms.
59. The composition of claim 53 wherein R.sup.5 is H or a lower alkyl group.
FIELD OF THE INVENTION This invention relates to a process for preparing compositions which are useful as intermediates for the preparation of low chlorine containing additives for lubricating oils and normally liquid fuels, compounds prepared by the process, and dilactone compounds.
BACKGROUND OF THE INVENTION Numerous types of additives are used to improve lubricating oil and fuel compositions. Such additives include, but are certainly not limited to dispersants and detergents of the ashless and ash-containing variety, oxidation inhibitors, anti-wear additives, friction modifiers, and the like. Such materials are well known in the art and are described in many publications, for example, Smalheer, et al, "Lubricant Additives", Lezius-Hiles Co., Cleveland, Ohio, USA (1967); M. W. Ranney, Ed., "Lubricant Additives", Noyes Data Corp., Park Ridge, N.J., USA (1973); M. J. Satriana, Ed., "Synthetic Oils and Lubricant Additives, Advances since 1979", Noyes Data Corp., Park Ridge N.J., USA (1982), W. C. Gergel, "Lubricant Additive Chemistry", Publication 694-320-65R1 of the Lubrizol Corp., Wickliffe Ohio, USA (1994); and W. C. Gergel et al, "Lubrication Theory and Practice" Publication 794-320-59R3 of the Lubrizol Corp., Wickliffe, Ohio, USA (1994); and in numerous United States patents, for example Chamberlin, III, U.S. Pat. No. 4,326,972, Schroeck et al, U.S. Pat. No. 4,904,401, and Ripple et al, U.S. Pat. No. 4,981,602. Many such additives are frequently derived from carboxylic reactants, for example, acids, esters, anhydrides, lactones, and others. Specific examples of commonly used carboxylic compounds used as intermediates for preparing lubricating oil additives include alkyl-and alkenyl substituted succinic acids and anhydrides, polyolefin substituted carboxylic acids, aromatic acids, such as salicylic acids, and others. Illustrative carboxylic compounds are described in Meinhardt, et al, U.S. Pat. No. 4,234,435; Norman et al, U.S. Pat. No. 3,172,892; LeSuer et al, U.S. Pat. No. 3,454,607 and Rense, U.S. Pat. No. 3,215,707.
SUMMARY OF THE INVENTION This invention provides a process for reacting, usually in the presence of an acidic catalyst,
(R.sup.1)(R.sup.2)C&#9552;C(R.sup.6)(CH(R.sup.7)(R.sup.8))   (III)
wherein each of R.sup.1 and R.sup.2 is, independently, hydrogen or a hydrocarbon based group and each of R.sup.6, R.sup.7 and R.sup.8 is, independently, hydrogen or a hydrocarbon based group, and
R.sup.3 C(O)(R.sup.4).sub.n C(O)OR.sup.5                   (IV)
and compounds of the formula ##STR1## wherein each of R.sup.3, R.sup.5 and R.sup.9 is independently H or a hydrocarbyl group, R.sup.4 is a divalent hydrocarbylene group, and n is 0 or 1, wherein the reactants are reacted in amounts ranging from more than 1.5 moles up to about 3 moles (B) per equivalent of (A), wherein equivalents of (A) are defined hereinafter.
The present invention also provides a composition comprising regiosomers selected from the group consisting of ##STR2## wherein each R.sup.1 is H or a hydrocarbon based group, each R.sup.3 is H or hydrocarbyl;
each R.sup.4 is a divalent hydrocarbylene group;
wherein X is a divalent hydrocarbyl group selected from the group consisting of ##STR3## each R.sup.5 is H or hydrocarbyl; and each of R.sup.6, R.sup.7 and R.sup.8 is independently H or a hydrocarbon based group, and T is selected from the group consisting of --OH and R.sup.5.
The Process The present invention relates to a process comprising reacting, usually in the presence of an acidic catalyst, more than 1.5 moles, preferably from about 1.6 to about 3 moles of (B) at least one carboxylic reactant per equivalent of (A) at least one olefinic compound wherein (A) and (B) are defined in greater detail hereinbelow.
The Catalyst The process of this invention is optionally conducted in the presence of an acidic catalyst. Acid catalysts, such as organic sulfonic acids, for example, paratoluene sulfonic acid and methane sulfonic acid, heteropolyacids, the complex acids of heavy metals (e.g., Mo, W, Sn, V, Zr, etc.) with phosphoric acids (e.g., phosphomolybdic acid), and mineral acids, for example, H.sub.2 SO.sub.4 and phosphoric acid, are useful. The amount of catalyst used is generally small, ranging from about 0.01 mole % to about 10 mole %, more often from about 0.1 mole % to about 2 mole %, based on moles of olefinic reactant.
In one embodiment, the olefinic compounds are substantially hydrocarbon, that is, each R group in (III) is H or contains essentially carbon and hydrogen. In one aspect within this embodiment, each of R.sup.1, R.sup.2, R.sup.7 and R.sup.8 is hydrogen and R.sup.6 is a hydrocarbyl group, frequently containing from 7 to about 5,000 carbon atoms, more often from about 30 up to about 200 carbon atoms, preferably from about 50 up to about 100 carbon atoms. In another aspect of this embodiment, each of R.sup.1 and R.sup.2 is hydrogen, R.sup.6 is H or a lower alkyl group and the group (CH(R.sup.7)(R.sup.8)) is a hydrocarbyl group, frequently containing from 7 to about 5,000 carbon atoms, more typically from about 30 up to about 200 carbon atom, preferably from 50 up to about 100 carbon atoms.
Preferably, the hydrocarbyl groups are aliphatic groups. In one preferred embodiment, when an R group is an aliphatic group containing a total of from about 30 to about 100 carbon atoms, the olefinic compound is derived from homopolymerized and interpolymerized C.sub.2-18 mono- and di-olefins, preferably 1-olefins. In a preferred embodiment, the olefins contain from 2 to about 5 carbon atoms, preferably 3 or 4 carbon atoms. Examples of such olefins are ethylene, propylene, butene-1, isobutylene, butadiene, isoprene, 1-hexene, 1-octene, etc. R groups can, however, be derived from other sources, such as monomeric high molecular weight alkenes (e.g. 1-tetracontene), aliphatic petroleum fractions, particularly paraffin waxes and cracked analogs thereof, white oils, synthetic alkenes such as those produced by the Ziegler-Natta process (e.g., poly-(ethylene) greases) and other sources known to those skilled in the art. Any unsaturation in the R groups may be reduced by hydrogenation according to procedures known in the art, provided at least one olefinic group remains as described for (III).
In one preferred embodiment, at least one R is derived from polybutene, that is, a polymer of C.sub.4 olefins, including 1-butene, 2-butene and isobutylene. Those derived from isobutylene, i.e., polyisobutylenes, are especially preferred. In another preferred embodiment, R is derived from polypropylene. In another preferred embodiment, R is derived from ethylene-alpha olefin polymers, particularly ethylene-propylene-diene polymers. Molecular weights of such polymers may vary over a wide range, but especially preferred are those having number average molecular weights (M.sub.n) ranging from about 300 to about 20,000, preferably 700 to about 5000. In one preferred embodiment, the olefin is an ethylene-propylene-diene copolymer having M.sub.n ranging from about 900 to about 2500. An example of such materials are the Trilene marketed by the Uniroyal Company, Middlebury, Conn., USA.
A preferred source of hydrocarbyl groups R are polybutenes obtained by polymerization of a C.sub.4 refinery stream having a butene content of 35 to 75 weight percent and isobutylene content of 15 to 60 weight percent in the presence of a Lewis acid catalyst such as aluminum trichloride or boron trifluoride. These polybutenes contain predominantly (greater than 80% of total repeating units) isobutylene repeating units of the configuration ##STR5## These polybutenes are typically monoolefinic, that is they contain but one olefinic bond per molecule.
Specific characterization of olefin reactants (A) used in the processes of this invention can be accomplished by using techniques known to those skilled in the art. These techniques include general qualitative analysis by infrared and determinations of average molecular weight, e.g., M.sub.n, number average molecular weight, etc., employing vapor phase osmometry (VPO) and gel permeation chromatography (GPC). Structural details can be elucidated employing proton and carbon 13 (C.sup.13) nuclear magnetic resonance (NMR) techniques. NMR is useful for determining substitution characteristics about olefinic bonds, and provides some details regarding the nature of the substituents. More specific details regarding substituents about the olefinic bonds can be obtained by cleaving the substituents from the olefin by, for example, ozonolysis, then analyzing the cleaved products, also by NMR, GPC, VPO, and by infra-red analysis and other techniques known to the skilled person.
and compounds of the formula ##STR8## wherein each of R.sup.3, R.sup.5 and R.sup.9 is independently H or a hydrocarbyl group, R.sup.4 is a divalent hydrocarbylene group, and n is 0 or 1. Specific embodiments of the groups R.sup.3 and R.sup.5 are set forth hereinabove where corresponding groups in the compound (I) are described. R.sup.9 is H or hydrocarbyl, preferably H or lower alkyl.
Reactant (B) may be a compound of the formula ##STR9## wherein each of R.sup.3 and R.sup.5 is independently H or alkyl. Such compounds arise when the carbonyl reactant is hydrated. Glyoxylic acid monohydrate is a representative example.
The process of this invention is conducted at temperatures ranging from ambient up to the lowest decomposition temperature of any of the reactants, usually from about 60 often from about 120 about 160 from about 1.6 to about 3 moles of reactant (B) per equivalent of reactant (A), more often from about 1.8 to about 2.5 moles of (B) per equivalent of (A) and preferably from about 1.9 to about 2.1 moles (B) per equivalent of (A).
The Compounds In another embodiment, this invention relates to a composition comprising regioisomers selected from the group consisting of compounds of the formula ##STR10## wherein y=0 or 1, n=0 or 1 and X is a divalent hydrocarbyl group selected from the group consisting of ##STR11## when y=0, and ##STR12## when y=1, and T is selected from the group consisting of --OH and R.sup.5. More often T is --OH.
Each R.sup.1 is independently H or a hydrocarbon based group. In one particular embodiment, each R.sup.1 is independently H or a lower alkyl group. As used herein, the expression "lower alkyl" refers to alkyl groups containing from 1 to 7 carbon atoms. Examples include methyl, ethyl and the various isomers of propyl, butyl, pentyl, hexyl and heptyl. In one especially preferred embodiment, each R.sup.1 is H.
Each R.sup.3 is independently H or hydrocarbyl. These hydrocarbyl groups are usually aliphatic, that is, alkyl or alkenyl, preferably alkyl, more preferably, lower alkyl. Especially preferred is where R.sup.3 is H or methyl, most preferably, H.
Each R.sup.4 is independently a divalent hydrocarbylene group. This group may be aliphatic or aromatic, but is usually aliphatic. Often, R.sup.4 is an alkylene group containing from 1 to about 10 carbon atoms, more often from 1 to about 3 carbon atoms. The `n` is 0 or 1; that is, in one embodiment, R.sup.4 is present and in another embodiment, R.sup.4 is absent. More often, R.sup.4 is absent.
R.sup.5 is H or hydrocarbyl. When R.sup.5 is hydrocarbyl, it is usually an aliphatic group, often a group containing from 1 to about 30 carbon atoms, often from 8 to about 18 carbon atoms. In another embodiment, R.sup.5 is lower alkyl, wherein "lower alkyl" is defined hereinabove. Most often, R.sup.5 is H.
When at least one of R.sup.6, R.sup.7 and R.sup.8 is a hydrocarbyl group, it preferably contains from 7 to about 5,000 carbon atoms. More often, such groups are aliphatic groups. In one embodiment, R.sup.6 is an aliphatic group containing from about 10 to about 300 carbon atoms. In another embodiment, R.sup.6 contains from 30 to about 100 carbon atoms and is derived from homopolymerized and interpolymerized C.sub.2-18 olefins.
In a further embodiment, at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from 10 to about 300 carbon atoms. Often, at least one of R.sup.7 and R.sup.8 contains from about 30 to about 100 carbon atoms and is derived from homopolymerized and interpolymerized C.sub.2-18 olefins. The polymerized olefins are frequently 1-olefins, preferably ethylene, propylene, butenes, isobutylene and mixtures thereof. Polymerized olefins are frequently referred to herein as polyolefins.
In yet another embodiment at least one of R.sup.7 and R.sup.8 is an aliphatic group containing from 8 to about 24 carbon atoms. In another embodiment at least one R.sup.7 and R.sup.8 is an aliphatic group containing 12 to about 50 carbon atoms. Within this embodiment, most often one of R.sup.7 and R.sup.8 is H and the other is the aliphatic group.
In one preferred embodiment, each of R.sup.1, and R.sup.3 is independently hydrogen or a lower alkyl or alkenyl group. In one especially preferred embodiment, each of R.sup.1 and R.sup.3 is hydrogen and each of y and n=0.
In another preferred embodiment, R.sup.6 is an aliphatic group containing from about 8 to about 150 carbon atoms, R.sup.5 is H, n is 0 and R.sup.3 is H.
EXAMPLE 1 A reactor is charged with 450 parts of polyisobutene having M.sub.n about 1000 and 92 parts 50% aqueous glyoxylic acid. The materials are heated under N.sub.2 at 200 collecting 35 parts distillate in a Dean-Stark trap. The materials are stripped to 180 filtered at 150 spectrum shows prominent C═O absorption. saponification No.=36. Total acid No.=5.5
EXAMPLE 2 A reactor is charged with 380 parts polyisobutene having M.sub.n about 1000 and 75 parts glyoxylic acid monohydrate. The materials are heated under N.sub.2 at 200 distillate in a Dean-Stark trap. The materials are filtered at 150
EXAMPLE 3 A reactor is charged with 300 parts polyisobutene (CE5203, BASF) having a M.sub.n about 1000 and containing about 49 mole % terminal vinylidene groups, 88.8 parts 50% aqueous glyoxylic acid and 1 part sulfuric acid and a few drops of silicone antifoam agent. Under N.sub.2, the materials are heated to 100 125 150 total of 49 parts distillate in a Dean-Stark trap. The materials are filtered at 150 Saponification No.+71.4; total acid no.=27, 7% unreacted polyisobutene determined by thin layer chromatography using a flame ionization detector (TLC-FID).
EXAMPLE 4 A reactor is charged with 1360 parts polyisobutene (Glissopal ES3250) having M.sub.n about 1000 and containing about 87 mole percent terminal vinylidene groups, 250 parts glyoxylic acid monohydrate and 1.35 parts 70% aqueous methane sulfonic acid. The materials are heated under N.sub.2 for 4 hours at 155 distillate in a Dean-Stark trap. The materials are filtered at 155 spectrum: very strong lactone C═O at 1774 cm.sup.-1. Saponification No.+107; Total acid no+31.8, 9% unreacted polyisobutene (TLC-FID).
EXAMPLE 5 A reactor is charged with 500 parts of the polyisobutene of Example 3 and 148 parts 50% aqueous glyoxylic acid. The materials are heated to 150 distillate. Unreacted polyisobutylene (TLC-FID)+29.2% The materials are mixed at 150 filtered employing a diatomaceous earth filter aid. Saponification No.=46; total acid No.=13.
EXAMPLE 6 To a reactor are charged 1000 parts of the polyisobutene of Example 4, 296 parts 50% aqueous glyoxylic acid and a few drops silicone antifoam agent. The mixture is heated to 160 hours while removing aqueous distillate. The material contains by TLC-FID 22% unreacted polyisobutene. Diluent oil, 287 parts, is added, the materials are heated to 110 earth filter aid. Saponification No.=57, Total acid no.=11.5.
EXAMPLE 7 A reactor is charged with 300 parts polyisobutene (Glissopal ES 3252, BASF) having M.sub.n about 2400 and containing about 70 mole percent terminal vinylidene groups and 35.8 parts 50% aqueous glyoxylic acid. The materials are heated to 160 Unreacted polyisobutene (TLC-FID)=24%. Mineral oil diluent, 84 parts, is added and the materials are mixed at 110 diatomaceous earth filter aid. Saponification No.=22.4,Total acid No.=6.9.
EXAMPLE 8 A reactor is charged with 500 parts of polyisobutene (Ultravis 10, BP Chemicals) having M.sub.n about 1000 which is heated to 100 then 9 parts 70% aqueous methanesulfonic acid are added followed by dropwise addition of 148 parts 50% aqueous glyoxylic acid over 0.5 hour. The temperature is increased to 150 at 150 polyisobutene. The materials are mixed with 144 parts mineral oil diluent and filtered with a diatomaceous earth filter aid. Saponification no.=44, total acid no.=17.5.
EXAMPLE 9 The procedure of Example 1 is repeated replacing the polyisobutylene with an equivalent amount, based on C═C, of C.sub.16-18 alpha olefin.
EXAMPLE 10 The procedure of Example 2 is repeated replacing the polyisobutylene with equivalent amounts (based on C═C) of C.sub.24-28 alpha olefin.
EXAMPLE 11 The procedure of Example 1 is repeated replacing glyoxylic acid with an equivalent amount, based on --COOH, of pyruvic acid.
EXAMPLE 12 The procedure of Example 1 is repeated replacing glyoxylic acid with an equivalent amount (based on COOH) of levulinic acid.
EXAMPLE 13 A reactor is charged with 3000 parts of polyisobutylene having a number average molecular weight of about 2400 (Glissopal ES 3252, BASF), 230.3 parts glyoxylic acid monohydrate, 17.5 parts 70% aqueous methane sulfonic acid and a few drops of a silicone antifoam agent. The materials are heated under N.sub.2 purge (0.3 cubic feet per hour) to 130 then are heated at 130 a total of 140 parts aqueous distillate. The materials are cooled to room temperature, 2093 parts mineral oil diluent are added and the solution is stirred while heating to 130 with a diatomaceous earth filter aid. Saponification no.=20.2; Total acid no.=6.7. Unreacted polyisobutylene=11% (TLC-FID).
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Chem., vol. 52, pp. 1186-1189, 1987.* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS6211122 *Jul 27, 1998Apr 3, 2001The Lubrizol CorporationCarboxylic compositions and derivatives thereof and use as lubricating oil and fuel additivesUS6245721Nov 2, 1999Jun 12, 2001Peter ChunLubrication additive compositionWO2009045979A1Sep 30, 2008Apr 9, 2009Lubrizol CorpLubricants that decrease micropitting for industrial gearsWO2011059626A1Oct 14, 2010May 19, 2011The Lubrizol CorporationLubricant system clean-up compositions and methods thereofWO2011146289A1May 11, 2011Nov 24, 2011The Lubrizol CorporationMethods and compositions that provide detergencyWO2011149799A1May 23, 2011Dec 1, 2011The Lubrizol CorporationMethod to provide power gain in an engineWO2011159742A1Jun 15, 2011Dec 22, 2011The Lubrizol CorporationMethods of removing deposits in oil and gas applicationsWO2012084906A1Dec 20, 2011Jun 28, 2012Rhodia OperationsFuel additive composition containing a dispersion of iron particles and a detergentWO2012162020A1May 15, 2012Nov 29, 2012The Lubrizol CorporationStabilized blends containing antioxidantsWO2012162027A1May 15, 2012Nov 29, 2012The Lubrizol CorporationStabilized blends containing friction modifiersWO2012162219A1May 21, 2012Nov 29, 2012The Lubrizol CorporationStabilized blends containing friction modifiersWO2012162282A1May 22, 2012Nov 29, 2012The Lubrizol CorporationStabilized blends containing friction modifiersWO2012177529A1Jun 18, 2012Dec 27, 2012The Lubrizol CorporationLubricating compositions containing salts of hydrocarbyl substituted acylating agentsWO2013043332A1Aug 29, 2012Mar 28, 2013The Lubrizol CorporationQuaternary ammonium salts in heating oils* Cited by examinerClassifications U.S. Classification549/283, 549/285, 549/306International ClassificationC10L10/08, C10L1/24, C07D493/04, C08L23/00, C10L1/188, C10L1/14, C10L1/18, C10L1/19, C10M129/95, C10M159/12, C08L23/26, C10L1/238, C10L1/198, C08F8/00, C10M129/93, C10L1/22Cooperative ClassificationC10M2207/286, C10L1/238, C07D493/04, C10M129/95, C10M2207/122, C10M2207/282, C10M2207/125, C10L1/19, C10L1/231, C10M2207/283, C10L1/2418, C10M129/93, C10L1/2286, C08F8/28, C10M2207/289, C10L1/1881, C10N2210/01, C10M2207/129, C10M2207/281, C10M2207/121, C10M2207/22, C10L1/198, C10M2207/123, C10L1/2475, C10L1/222, C10L1/1817, C10L1/1855, C10M2207/124, C10L1/143European ClassificationC08F8/00, C10L1/198, C10L1/185B1, C10L1/24P3, C10L1/18W, C10M129/95, C07D493/04, C10L1/14B, C10L1/238, C10M129/93Legal EventsDateCodeEventDescriptionMar 6, 2007FPExpired due to failure to pay maintenance feeEffective date: 20070105Jan 5, 2007LAPSLapse for failure to pay maintenance feesJul 26, 2006REMIMaintenance fee reminder mailedJun 14, 2002FPAYFee paymentYear of fee payment: 4Dec 18, 1997ASAssignmentOwner name: LUBRIZOL CORPORATION, THE, OHIOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:DIETZ, JEFFRY G.;BAKER, MARK R.;ADAMS, PAUL E.;REEL/FRAME:008911/0581Effective date: 19951019RotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services©2012 Google