Amino phenols useful as additives for fuels and lubricants
AssigneeThe Lubrizol Corporation
InventorRichard M. Lange
Life of this patent
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Abstract
Amino phenols of the general formula ##STR1## wherein R is a substantially saturated, hydrocarbon-based group of at least about 30 aliphatic carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants. These amino phenols can be conveniently prepared by nitrating an appropriate hydroxy aromatic compound and reducing the nitro groups to amino groups. Typically such amino phenols are formed by nitration and reduction of alkyl phenols having an alkyl or alkenyl group of at least about 50 carbon atoms.
Claims25
A compound of the formula ##STR20## wherein R is a substantially saturated hydrocarbon-based substituent of at least 30 aliphatic carbon atoms;
- a, b, and c are each independently an integer of 1 up to three times the number of aromatic nuclei present in Ar* with the proviso that the sum of a, b, and c does not exceed the unsatisfied valences of Ar*;
- and Ar* is a single ring or fused ring aromatic moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, halo, or combinations of two or more of said optional substituents;
- with the proviso that when Ar* is a benzene nucleus having only one hydroxyl and one R substituent, the R substituent is para to said hydroxyl substituent.
An amino-containing composition made by
- (I) nitrating with at least one nitrating agent at least one compound of the formula ##STR21## wherein R is a substantially saturated hyrocarbon-based group of at least 30 aliphatic carbon atoms;
- a and c are each independently an integer of 1 up to three times the number of aromatic nuclei present in Ar" with the proviso that the sum of a, b and c does not exceed the unsatisfied valences of Ar";
- and Ar" is a single ring or fused ring aromatic moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, nitro, and halo, or combinations of two or more optional substituents, with the provisos that (a) Ar" has at least one hydrogen atom directly bonded to a carbon atom which is part of an aromatic nucleus, and (b) when Ar" is a benzene having only one hydroxyl and one R substituent, the R substituent is para to said hydroxyl substituent, to form a first reaction mixture containing a nitro intermediate, and
- (II) reducing at least about 50% of the nitro groups in said first reaction mixture to amino groups.
An amino-containing composition made by reducing at least about 50% of the nitro groups to amino groups in a compound or mixture of compounds of the formula ##STR22## wherein R is a substantially saturated hydrocarbon-based substituent of at least 30 aliphatic carbon atoms;
- a, b, and c are each independently an integer of 1 up to three times the number of aromatic nuclei present in Ar* with the proviso that the sum of a, b, and c does not exceed the unsatisfied valences of Ar*;
- and Ar* is a single ring or fused ring aromatic moiety having 0 to 3 optional substituents selected from the group consisting of lower alkyl, lower alkoxyl, halo, or combinations of two or more of said optional substituents;
- with the proviso that when Ar* is a benzene nucleus having only one hydroxyl and one R substituent, the R substituent is para to said hydroxyl substituent.
Dependencies are inferred from the claim text.