Liquid polyfunctional additives for improved fuel lubricity

Details Liquid polyfunctional additives for improved fuel lubricity Liquid polyfunctional additives for improved fuel lubricity

1998-02-02

2001-10-02

Medley, Margaret (Department: 1714)

Fuel and related compositions

Liquid fuels

Plant or animal extract mixtures or extracts of...

C044S329000, C044S330000, C044S333000, C044S334000, C044S340000, C044S341000, C044S386000

Reexamination Certificate

active

06296677

ABSTRACT:

The present invention relates to anti-wear fuel compositions comprising a fuel, preferably a diesel and other fuels having lower sulfur and/or aromatic contents and a liquid polyfunctional additive, and to the use of the liquid polyfunctional additive as anti-wear agent and lubricity improver for an engine fuel system.
The United States Government has mandated a reduction in the sulfur and aromatic content of commercial diesel fuels. Regulatory agencies in other countries have either introduced such a requirement or are contemplating doing so. This regulatory regime causes a problem insofar as the fuel industry recognises that fuels which comply with the regulation will exhibit reduced lubricity. The refining processes needed to produce these fuels require more severe hydrotreatment which removes polar species from the fuel and reduces its lubricity. Lubricity is a measure of the capacity of the fuel to flow through the engine without causing excessive wear. Even marginal changes in lubricity may be significant in increasing wear of fuel pumps, valves and injector nozzles over an extended period of use.
WO 96/16143 discloses that specific phosphorus esters improve the lubricity (anti-wear properties) of hydrocarbon fuels, oxygenate fuels or mixtures thereof, particularly diesel or aviation fuels having reduced sulfur and/or aromatic content.
EP-A-0 565 487 which is related to U.S. Pat. No. 5,478,875 discloses liquid antioxidants as stabilizers for polymers and lubricants.
Surprisingly, it has now been found that these liquid antioxidants possess also anti-wear, lubricity improving and corrosion inhibiting properties in fuels having lower sulfur and/or aromatic contents.
Accordingly, the present invention relates to an anti-wear fuel composition comprising
&agr;) a fuel and
&bgr;) at least a product obtainable by reacting components a), b) and c), where component a) is a compound of the formula I or a mixture of compounds of the formula I, component b) is a compound of the formula II or a mixture of compounds of the formula II and component c) is a compound of the formula III or a mixture of compounds of the formula III,
in which, in the compound of the formula I,
the radicals Y independently of one another are OH, (HOCH
2
CH
2
)
2
N— or —HNR
1
and
the radicals R
1
are hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl,
C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl, phenyl, or phenyl which is substituted by 1 to 3 radicals A
1
, the radicals A
1
independently of one another being C
1
-C
12
alkyl, halogen, hydroxyl, methoxy or ethoxy, in which
R
2
is hydrogen, C
1
-C
8
alkyl, O
19
, OH, NO, —CH
2
CN, C
1
-C
18
alkoxy, C
5
-C
12
cycloalkoxy, C
3
-C
6
alkenyl, C
7
-C
9
phenylalkyl or C
7
-C
9
phenylalkyl which is mono-, di- or trisubstituted on the phenyl ring by C
1
-C
4
alkyl, or R
2
is furthermore C
1
-C
8
acyl or HOCH
2
CH
2
—, and a is the number 1, 2, 3, 4 or 6, where,
if Y is OH and a is 1,
X is C
1
-C
45
alkyl, C
3
-C
18
alkenyl, —CH
2
CH
2
T
1
(CH
2
CH
2
O)
b
R
4
or
 in which R
2
is as defined above, and
T
1
is oxygen, sulfur or
R
4
is C
1
-C
20
alkyl,
b is an integer ranging from 0 to 10 and
R
5
is hydrogen, C
1
-C
18
alkyl or phenyl, or,
if Y is OH and a is 2,
X is —CH
2
CH
2
T
2
(CH
2
CH
2
O)
b
CH
2
CH
2
—, in which b is as defined above,
 in which
T
2
is oxygen, sulfur,
 and R
5
is as defined above,
R
6
is hydrogen, C
1
-C
18
alkyl or phenyl,
c is an integer ranging from 2 to 10,
d is an integer ranging from 2 to 6 and
R
7
and R
8
independently of one another are hydrogen, C
1
-C
18
alkyl or phenyl, or R
7
and R
8
together with the C atom to which they are bonded form a C
5
-C
12
cycloalkyl ring, or
if a is 3,
X is C
3
-C
10
alkanetriyl or N(CH
2
CH
2
—)
3
, or,
if Y is OH and a is 4,
X is C
4
-C
10
alkanetetray,
 in which
R
9
is C
1
-C
4
alkyl, or,
if Y is OH and a is 6,
X is
 or C
6
-C
10
alkanehexayl, or,
if Y is HNR
1
and a is 1,
X is C
1
-C
18
alkyl, C
3
-C
18
alkenyl, C
5
-C
12
cycloalkyl, C
7
-C
9
phenylalkyl, phenyl,
 in which R
2
is as defined above or X is furthermore
or X together with R
1
is a group of the formula —CH
2
CH
2
CH
2
CH
2
CH
2
— or
—CH
2
CH
2
OCH
2
CH
2
—, in which
R
10
is hydrogen or methyl and
e is 2 or 3, or,
if Y is —HNR
1
and a is 2,
X is —C
f
H
2f
—,
 in which
f is an integer ranging from 2 to 10 and
g is an integer ranging from 1 to 6, and,
in the compound of the formula II,
the radicals Z are hydrogen or a group of the formula
 and
k is an integer ranging from 0 to 6, in which
h is 2 or 3,
i is an integer ranging from 0 to 12 and
R
11
is C
1
-C
30
alkyl, C
8
-C
30
alkenyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl, with the proviso that the compound of the formula II has a group
in the compound of the formula III,
R
12
is C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl,
R
15
is hydrogen, C
1
-C
18
alkyl, C
5
-C
12
cycloalkyl, phenyl or C
7
-C
9
phenylalkyl,
s is 0, 1 or 2,
Q is —C
m
H
2m
—,
 in which R
15
is as defined above,
m is an integer ranging from 0 to 3,
R
16
is C
1
-C
8
alkyl and
n is an integer ranging from 1 to 6, where,
if n is 1,
R
17
is hydrogen, C
1
-C
45
alkyl, C
5
-C
12
cycloalkyl, C
2
-C
18
alkenyl, a monovalent radical of a hexose, a monovalent radical of a hexitol,
 in which
R
2
is as defined above, or furthermore R
17
is —CH
2
CH
2
—T
3
—R
19
or
 in which
T
3
is oxygen, sulfur or
R
19
is
 in which R
12
and R
15
are as defined above, or R
19
is furthermore hydrogen, C
1
-C
24
alkyl, phenyl, C
5
-C
12
cycloalkyl or
 in which
p is an integer ranging from 2 to 4,
q is an integer ranging from 2 to 20,
R
22
is C
1
-C
18
alkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A
1
, in which the radicals A
1
independently of one another are C
1
-C
12
alkyl, halogen, hydroxyl, methoxy or ethoxy, or R
22
is furthermore C
5
-C
8
cycloalkyl,
R
23
and R
24
independently of one another are hydrogen or methyl, with the proviso that
R
23
and R
24
are not simultaneously methyl;
R
25
is hydrogen or C
1
-C
24
alkyl, or,
if n is 2,
R
17
is a divalent radical of a hexose, a divalent radical of a hexitol,
 in which p and q are as defined above, —CH
2
CH
2
—T
4
—CH
2
CH
2
—, —CH
2
—CH═CH—CH
2
—, —CH
2
—C≡C—CH
2
—,
 in which
R
18
and R
20
independently of one another are hydrogen or C
1
-C
12
alkyl or together are the radical —CH
2
CH
2
CH
2
CH
2
CH
2
—,
r is an integer ranging from 2 to 10,
T
4
is sulfur,
 in which R
7
and R
8
are as defined above, and
R
26
is hydrogen, C
1
-C
18
alkyl, phenyl or phenyl which is substituted by 1 to 3 radicals A
1
, in which the radicals A
1
are as defined above in formula I, or R
26
is furthermore
C
5
-C
8
cycloalkyl or
 in which R
2
is as defined above, or,
if n is 3,
R
17
is a trivalent radical of a hexose, a trivalent radical of a hexitol,
 in which
R
27
is hydrogen, CH
2
OH, C
1
-C
4
alkyl, C
1
-C
18
alkylamido or
 in which Q, R
12
and R
15
are as defined above, or,
if n is 4,
R
17
is a tetravalent radical of a hexose, a tetravalent radical of a hexitol,
C
4
-C
10
alkanetetrayl,
 or,
if n is 5,
R
17
is a pentavalent radical of a hexose or a pentavalent radical of a hexitol, or,
if n is 6,
R
17
is a hexavalent radical of a hexitol or
Alkyl having not more than 45 C atoms is a branched or unbranched radical such as, for example, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethyl-butyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, docosyl or pentacosyl. One of the preferred meanings of R
1
, R
4
and R
16
is, for example, C
1
-C
4
alkyl, of R
2
methyl, of R
11
C
1
-C
20
alkyl, of R
12
and R
15
C
1
-C
4
a

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