Aromatic Mannich compound-containing composition and process...

Fuel and related compositions – Liquid fuels – Organic nitrogen compound containing

Reexamination Certificate

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C528S129000, C528S152000, C528S162000, C524S765000, C524S767000, C044S412000, C044S417000, C044S436000, C044S450000, C044S639000

Reexamination Certificate

active

06179885

ABSTRACT:

TECHNICAL FIELD
The invention relates to aromatic Mannich compound-containing compositions and to a process for making these compounds. The aromatic Mannich compounds are dispersed in alcohol, and are useful as detergent additives for hydrocarbon fuels.
BACKGROUND OF THE INVENTION
Hydrocarbon fuels generally contain numerous deposit-forming substances. When used in internal combustion engines, deposits tend to form on and around constricted areas of the engine in contact with the fuels. In diesel engines, deposits tend to accumulate in the fuel injection system, thereby hampering good performance of the engine. In spark ignition engines deposits can build up on engine intake valves leading to progressive restriction of gaseous fuel mixture flow into the combustion chamber and also to valve sticking. It is common practice therefore to incorporate a detergent in the fuel composition for the purpose of inhibiting the formation, and facilitating the removal, of engine deposits, thereby improving engine performance. Mannich condensation products, obtained by reacting hydrocarbon-substituted phenols with aldehydes and amines, are known as detergents for fuels.
SUMMARY OF THE INVENTION
This invention relates to a composition, comprising
(I) an aromatic Mannich compound derived from:
(A) a hydroxy containing aromatic compound having the formula
 wherein in Formula (A-1): Ar is an aromatic group; m is 1, 2 or 3; n is a number from 1 to about 4; with the proviso that the sum of m and n does not exceed the number of available positions on Ar that can be substituted; each R
1
independently is a hydrocarbyl group of up to about 400 carbon atoms; and R
2
is H, amino or carboxyl;
(B) an aldehyde or ketone having the formula
 or a precursor thereof; wherein in Formula (B-1): R
1
and R
2
independently are H or hydrocarbyl groups having from 1 to about 18 carbon atoms; and R
2
can also be a carbonyl-containing hydrocarbyl group having from 1 to about 18 carbon atoms; and
(C) a mixture of water and an amine, said amine containing at least one primary or secondary amino group; and
(II) alcohol.
This invention also relates to a process, comprising:
reacting (A) a hydroxy containing aromatic compound having the formula
 wherein in Formula (A-1): Ar is an aromatic group; m is 1, 2 or 3; n is a number from 1 to about 4; with the proviso that the sum of m and n does not exceed the number of available positions on Ar that can be substituted; each R
1
independently is H or a hydrocarbyl group having from 1 to about 400 carbon atoms; and R
2
is H, amino or carboxyl;
with (B) an aldehyde or ketone having the formula
 or a precursor thereof; wherein in Formula (B-1): R
1
and R
2
independently are H or hydrocarbyl groups having from 1 to about 18 carbon atoms; and R
2
can also be a carbonyl-containing hydrocarbyl group having from 1 to about 18 carbon atoms; and
(C) a mixture of water and an amine, said amine containing at least one primary or secondary amino group;
in the presence of alcohol.
These aromatic Mannich compound-containing compositions are characterized by relatively high nitrogen levels which provide for enhanced detergent properties when used in fuels.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
As used herein, the term “hydrocarbyl substituent,” “hydrocarbyl group” or “hydrocarbon group” is 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, cycloalkenyl) 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.
The term “fuel-soluble” refers to materials that are soluble in a normally liquid hydrocarbon fuel (e.g. gasoline or diesel fuel) to the extent of at least one gram per 100 milliliters of fuels at 25° C.
In Formula (A-1), Ar may be a benzene or a naphthalene nucleus. Ar may be a coupled aromatic compound, the coupling agent preferably being O, S, CH
2
, a lower alkylene group having from 1 to about 6 carbon atoms, NH, and the like, with R
1
and OH generally being pendant from each aromatic nucleus. Examples of specific coupled aromatic compounds include diphenylamine, diphenylmethylene and the like. m is usually from 1 to 3, and in one embodiment 1 or 2, and in one embodiment 1. n is usually from 1 to 4, and in one embodiment 1 or 2, and in one embodiment 1. R
2
may be H, amino or carboxyl, and in one embodiment R
2
is H. R
1
is a hydrocarbyl group of up to about 400 carbon atoms, and in one embodiment up to about 250 carbon atoms, and in one embodiment up to about 150 carbon atoms. R
1
can be an alkyl group, alkenyl group or cycloalkyl group.
In one embodiment, R
1
is a hydrocarbyl group derived from an olefin polymer. The olefin polymer may be derived from an olefin monomer of 2 to about 10 carbon atoms, and in one embodiment about 3 to about 6 carbon atoms, and in one embodiment about 4 carbon atoms. Examples of the monomers include ethylene; propylene; butene-1; butene-2; isobutene; pentene-1; heptene-1; octene-1; nonene-1; decene-1; pentene-2; or a mixture of two or more thereof.
In one embodiment, R
1
is a polyisobutene group. The polyisobutene group may be made by the polymerization of a C
4
refinery stream having a butene content of about 35 to about 75% by weight and an isobutene content of about 30 to about 60% by weight.
In one embodiment, R
1
is a polyisobutene group derived from a polyisobutene having a high methylvinylidene isomer content, that is, at least about 70% methylvinylidene. Suitable high methylvinylidene polyisobutenes include those prepared using boron trifluoride catalysts. The preparation of such polyisobutenes in which the methylvinylidene isomer comprises a high percentage of the total olefin composition is described in U.S. Pat. Nos. 4,152,499 and 4,605,808, the disclosures of each of which are incorporated herein by reference.
Examples of suitable polyisobutenes having a high methylvinylidene content include Ultravis 10, a polyisobutene having a number average molecular weight of about 950 and a methylvinyidiene content of about 82%, and Ultravis 30, a polyisobutene having a number average molecular weight of about 1300 and a methylvinylidene content of about 74%, both available from BP Amoco.
The polyisobutene contemplated for use in the present invention may have a number average molecular weight in the range of about 200 to 5,000, and in one embodiment in the range of about 250 to 3,000, and in one embodiment the range of about 300 to 2,500, and in one embodiment in the range of about 500 to about 2300, and in one embodiment about 750 to about 1500.
In a preferred embodiment, component (A) is a polyisobutene-substituted phenol wherein the polyisobutene substituent is derived from a polyisobutene having a number average molecular weight in the

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