Fuel and related compositions – Liquid fuels – Organic nitrogen compound containing
Reexamination Certificate
1999-11-23
2001-05-01
Medley, Margaret (Department: 1714)
Fuel and related compositions
Liquid fuels
Organic nitrogen compound containing
C044S331000, C044S385000, C044S388000, C044S389000, C044S418000
Reexamination Certificate
active
06224642
ABSTRACT:
TECHNICAL FIELD
This invention relates to compositions which are useful as fuel additives and, more particularly, to fuel additives which are useful in reducing engine wear.
BACKGROUND OF THE INVENTION
The reduction of engine wear in internal combustion engines is a continuing problem. Many engine wear problems are addressed through the use of appropriate lubricating oil applications. However, engine wear reduction also often necessitates the formulation of fuels such as diesel fuel and gasoline with enhanced lubricity characteristics. The present invention provides a solution to the problem of reducing engine wear by providing a fuel additive combination that enhances the lubricity characteristics of fuels such as diesel fuel, gasoline, and the like.
U.S. Pat. No. 5,089,029 discloses a fuel oil composition which comprises fuel oil and 0.1 to 50,000 ppm of an additive compound having the formula
R—O—(AO)
m
—(C
3
H
6
NH)
n
H
in which R is a hydrocarbyl radical having 10 to 50 carbon atoms, A is an alkylene group having 2 to 6 carbon atoms, m is an integer of 10 to 50, and n is an integer of 1 to 3.
U.S. Pat. No. 5,660,601 discloses fuels for gasoline engines which contain small amounts of polyetheramines represented by the formula
R
1
—(OBu)
n
—NR
2
R
3
(I)
where: R
1
is C
2
—C
30
-alkyl; R
2
and R
3
, independently of one another, are each hydrogen, C
1
-C
6
-alkyl, aminoalkylene of the general formula
—R
4
—NR
5
R
6
(II)
or polyaminoalkylene of the general formula
—R
4
—NR
5
)
m
—R
6
(III)
where: R
4
is C
2
-C
10
-alkylene; R
5
and R
6
, independently of one another, are each hydrogen or C
1
-C
6
-alkyl; m is from 2 to 8; and Bu is a butylene radical derived from butylene oxide and n is from 12 to 28.
SUMMARY OF THE INVENTION
This invention relates to a composition, comprising:
(A) a compound represented by the formula
RO(C
4
H
8
O)
n
CH
2
CH
2
CH
2
NH
2
(I)
wherein in formula (I), R is an aliphatic hydrocarbyl group of about 8 to about 30 carbon atoms, an n is a number in the range of about 12 to about 30; and
(B) a compound selected from the group consisting of: a fatty acid; a fatty acid amide; a fatty acid ester; an amide, imide or ester derived from a hydrocarbyl substituted succinic acid or anhydride wherein the hydrocarbyl substituent has about 8 to about 30 carbon atoms; an alkoxylated amine; and mixtures of two or more thereof.
The invention also relates to concentrates and fuels containing the foregoing composition.
The inventive compositions are useful in enhancing the lubricity characteristics of fuels such as diesel fuel, gasoline, and the like. The inventive compositions, in one embodiment, are also useful in reducing intake valve deposits. The inventive compositions, in one embodiment, are useful in improving fuel economy.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
As used herein, the terms “hydrocarbyl substituent,” “hydrocarbyl group,” “hydrocarbyl substituted,” “hydrocarbon group,” and the like, are used to refer to a group having one or more carbon atoms directly attached to the remainder of a molecule and having a hydrocarbon or predominantly hydrocarbon character. Examples include:
(1) purely hydrocarbon groups, that is, aliphatic (e.g., alkyl, alkenyl or alkylene), and alicyclic (e.g., cycloalkyl, cycloalkenyli groups, aromatic groups, and aromatic-, aliphatic-, and alicyclic-substituted aromatic groups, as well as cyclic groups wherein the ring is completed through another portion of the molecule (e.g., two substituents together forming an alicyclic group);
(2) substituted hydrocarbon groups, that is, hydrocarbon groups containing non-hydrocarbon groups which, in the context of this invention, do not alter the predominantly hydrocarbon nature of the group (e.g., halo, hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulfoxy);
(3) hetero substituted hydrocarbon groups, that is, hydrocarbon groups containing substituents which, while having a predominantly hydrocarbon character, in the context of this invention, contain other than carbon in a ring or chain otherwise composed of carbon atoms. Heteratoms include sulfur, oxygen, nitrogen. In general, no more than two, and in one embodiment no more than one, non-hydrocarbon substituent is present for every ten carbon atoms in the hydrocarbon group.
The term “lower” when used in conjunction with terms such as alkyl, alkenyl, and alkoxy, is intended to describe such groups that contain a total of up to 7 carbon atoms.
Component (A) is a compound represented by the formula
RO(C
4
H
8
O)
n
CH
2
CH2CH
2
NH
2
(I)
wherein in formula (I), R is an aliphatic hydrocarbyl group of about 8 to about 30 carbon atoms, and n is a number in the range of about 12 to about 30. R can be an straight chain or branched chain alkyl or alkenyl group. In one embodiment, R is a branched chain alkyl groups consisting of a straight chain back bone with one or more methyl groups, and in one embodiment 2 to about 6 methyl groups, and in one embodiment about 4 methyl groups, attached as side chains to the back bone. In one embodiment, R has 8 to 15 carbon atoms, and in one embodiment 12 to 14 carbon atoms, and in one embodiment 13 carbon atoms. In one embodiment, n is a number in the range of about 18 to about 22. In one embodiment, R has 13 carbon atoms, and n is about 20. In one embodiment, component (A) is a compound represented by the formula
wherein in formula (I-A), n is a number in the range of about 12 to about 30, and in one embodiment n is about 18 to about 22, and in one embodiment n is about 20.
The compound represented by the formula (I) may be prepared by cyanoethylating an adduct of an alcohol, having about 8 to about 30 carbon atoms and an alkylene oxide with acrylonitrile and hydrogenating the obtained product, if necessary, followed by the repetition of the cyanoethylation and the hydrogenation. The cyanoethylation is conducted by stirring the reaction system under heating in the presence of a strong base catalyst such as caustic alkali. The hydrogenation may be conducted in the presence of a hydrogenation catalyst such as Raney nickel.
When the compound represented by the formula (I) is prepared by the above process, the alcohol ROH [wherein R is the same as that defined for the formula (I)] to be used as a raw material has about 8 to about 30 carbon atoms. Examples of the alcohol include branched-chain monohydric alcohols prepared by the Oxo process. These include tridecyl, isodecyl, 2-ethylhexyl alcohols, and the like. Examples of the alcohol also include straight-chain even carbon numbered alcohols prepared by the Ziegler process such as octyl, decyl, dodecyl, tetradecyl, and the like. Also contemplated are various saturated and unsaturated natural alcohols.
Component (B) is a fatty acid; a fatty acid amide; a fatty acid ester; an amide, imide or ester derived from a hydrocarbyl substituted succinic acid or anhydride and an amine or an alcohol; an alkoxylated amine; or a mixture of two or more thereof.
The term “fatty acid” as used in the specification and claims refers to acids which may be obtained by the hydrolysis of a naturally occurring vegetable or animal fat or oil. These acids usually contain from about 8 to about 22 carbon atoms and include, for example, caprylic acid, capric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, etc. Acids containing from about 10 to about 22 carbon atoms are useful, and in one embodiment, those acids containing from about 16 to about 18 carbon atoms can be used.
The hydrocarbyl-substituted succinic acid or anhydride used in making the amides, imides and esters derived from such acid or anhydride may be represented by the formulae
wherein R is a hydrocarbyl group of about 8 to about 30 carbon atoms, and in one embodiment about 8 to about 18 carbon atoms, and in one embodiment about 12 carbon atoms. In one embodiment R is an alkyl or an alkenyl group. The hydrocarbyl group R may be derived from ethylene, propylene, 1-butene, isobutylene, 1-pentene, 2-methyl-1-butene, 3-methyl-1-buten
Adams Paul E.
Daly Daniel T.
Jackson Mitchell M.
Esposito, Esq. Michael F.
Medley Margaret
The Lubrizol Corporation
Toomer Cephia D.
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