Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1998-08-05
2001-03-27
Kight, John (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C544S171000, C544S171000, C544S171000, C544S320000
Reexamination Certificate
active
06207839
ABSTRACT:
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 coupled lactone 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.
Many carboxylic intermediates used in the preparation of lubricating oil additives contain chlorine. While the amount of chlorine present is often only a very small amount of the total weight of the intermediate, the chlorine frequently is carried over into the carboxylic derivative which is desired as an additive. For a variety of reasons, including government regulation, environmental concerns, and commercial reasons the industry has been making efforts to reduce or to eliminate chlorine from additives designed for use as lubricant or fuel additives.
Accordingly, it is desirable to provide low chlorine or chlorine free intermediates which can be used to prepare low chlorine or chlorine free derivatives for use in lubricants and fuels.
The present invention provides a method for preparing compounds which meet this requirement.
B. B. Snider and J. W. van Straten, J. Org. Chem., 44, 3567-3571 (1979) describes certain products prepared by the reaction of methyl glyoxylate with several butenes and cyclohexenes. K. Mikami and M. Shimizu, Chem. Rev., 92, 1021-1050 (1992) describe carbonyl-ene reactions, including glyoxylate-ene reactions. D. Savostianov (communicated by P.Pascal), C.R. Acad. Sc. Paris, 263, (605-7) (1966) relates to preparation of some &agr;-hydroxylactones via the action of glyoxylic acid on olefins. M. Kerfanto et. al., C.R. Acad. Sc. Paris, 264, (232-5) (1967) relates to condensation reactions of &agr;-&agr;-di-(N-morpholino)-acetic acid and glyoxylic acid with olefins.
SUMMARY OF THE INVENTION
The present invention relates to a process for preparing compounds useful as intermediates for preparing performance improving additives for lubricants and fuels which comprises reacting, optionally in the presence of an acidic catalyst selected from the group consisting of organic sulfonic acids, heteropolyacids, and mineral acids,
(A) at least one olefinic compound of the general formula
(R
1
)(R
2
)C═C(R
6
)(CH(R
7
)(R
8
))
wherein each of R
1
and R
2
is, independently, hydrogen or a hydrocarbon based group and each of R
6
, R
7
and R
8
is, independently, hydrogen or a hydrocarbon based group;
(B) at least one carboxylic reactant selected from the group consisting of compounds of the formula
R
3
C(O)(R
4
)
n
C(O)OR
5
(IV)
and compounds of the formula
wherein each of R
3
, R
5
and each R
9
is independently H or a hydrocarbyl group, R
4
is a divalent hydrocarbylene group, and n is 0 or 1 in amounts ranging from 0.6 moles (B) per mole of (A) to 1.5 moles (B) per equivalent of (A); and from about 0.5 to about 2 moles, per mole of (B), of
(C) at least one aldehyde or ketone;
as well as products obtained by the process of the invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
As used herein, the terms “hydrocarbon”, “hydrocarbyl” or “hydrocarbon based” mean that the group being described has predominantly hydrocarbon character within the context of this invention. These include groups that are purely hydrocarbon in nature, that is, they contain only carbon and hydrogen. They may also include groups containing non-hydrocarbon substituents or atoms which do not alter the predominantly hydrocarbon character of the group. Such substituents may include alkoxy-, nitro-, etc. These groups also may contain hetero atoms. Suitable hetero atoms will be apparent to those skilled in the art and include, for example, sulfur, nitrogen and oxygen. Therefore, while remaining predominantly hydrocarbon in character within the context of this invention, these groups may contain atoms other than carbon present in a chain or ring otherwise composed of carbon atoms.
In general, no more than about three non-hydrocarbon substituents or heteroatoms, and preferably no more than one, will be present for every 10 carbon atoms in the hydrocarbon, hydrocarbyl or hydrocarbon based groups. Most preferably, the groups are purely hydrocarbon in nature, that is they are essentially free of atoms other than carbon and hydrogen.
Throughout the specification and claims the expression soluble or dispersible is used. By soluble or dispersible is meant that an amount needed to provide the desired level of activity or performance can be incorporated by being dissolved, dispersed or suspended in an oil of lubricating viscosity or in a normally liquid fuel. Usually, this means that at least about 0.001% by weight of the material can be incorporated in a lubricating oil or normally liquid fuel. For a further discussion of the terms oil soluble and dispersible, particularly “stably dispersible”, see U.S. Pat. No. 4,320,019 which is expressly incorporated herein by reference for relevant teachings in this regard.
As noted hereinabove, provided by this invention is a process for preparing low chlorine or chlorine free compositions useful as intermediates for preparing low chlorine or chlorine free additives for lubricating oil and fuel compositions.
The Process
In one embodiment, the present invention relates to a process comprising reacting, optionally in the presence of an acidic catalyst selected from the group consisting of organic sulfonic acids, heteropolyacids, and mineral acids,
(A) at least one olefinic compound of the general formula
(R
1
)(R
2
)C═C(R
6
)(CH(R
7
)(R
8
))
wherein each of R
1
and R
2
is, independently, hydrogen or a hydrocarbon based group and each of R
6
, R
7
and R
8
is, independently, hydrogen or a hydrocarbon based group;
(B) at least one carboxylic reactant selected from the group consisting of compounds of the formula
R
3
C(O)(R
4
)
n
C(O)OR
5
(IV)
and compounds of the formula
wherein each of R
3
, R
5
and each R
9
is independently H or a hydrocarbyl group, R
4
is a divalent hydrocarbylene group, and n is 0 or 1 in amounts ranging from 0.6 moles (B) per mole of (A) to 1.5 moles (B) per equivalent of (A); and from about 0.5 to about 2 moles, per mole of (B), of
(C) at least one aldehyde or ketone.
Reactants (A), (B), and (C) may be present at the outset of the reaction or (A) and (B) may be reacted first
Covington Raymond
Fischer Joseph P.
Kight John
Shold David M.
The Lubrizol Corporation
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