Back to results
US 2009/0156449 A1Published application
Alkylated 1,3-benzenediamine compounds and methods for producing same
AssigneeChemtura Corporation
InventorsRobert G. Rowland, Joseph F. Stieber, Clifford M. Pratt, Ronald D. Abbott
Life of this patent
Estimating the term…
Abstract
An alkylated 1,3-benzenediamine compound used as a deposit-control lubricant additives for organic materials including lubricating oil, gasoline, and diesel fuels. The invention improves the oxidative stability of the lubricants and fuels by adding the alkylated 1,3-benzenediamine compound. The alkylated 1,3-benzenediamine compound is formed using a catalytic hydrogenation that alkylates the 4 and/or 6 position of the central aromatic ring.
Claims26
A compound of structure (I) having the general formula:
- wherein R1 and R2 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, C5-C20 heterocyclo and hydrogen, provided that at least one of R1 and R2 is not hydrogen;
- wherein R3 and R4 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, and C5-C20 heterocyclo;
- and
- wherein R5 and R6 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, and C5-C20 heterocyclo.
1 more element
A process for alkylating a 1,3-benzenediamine compound comprising:
- providing a carbonyl compound selected from the group consisting of an aldehyde having the general formula:
- and a ketone having the general formula:
- wherein R10 and R11 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, C5-C20 heterocyclo and a ring compound formed by fusing R10 and R11 to form a C4-C20 cycloalkyl, C5-C20 aryl, or C5-C20 heterocyclo;
- and
- reacting the carbonyl compound with the 1,3-benzenediamine compound in the presence of hydrogen and a hydrogenation catalyst to form a structure (I) having the general formula:
- wherein R1 and R2 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, C5-C20 heterocyclo and hydrogen, provided that at least one of R1 and R2 is not hydrogen;
- wherein R3 and R4 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, and C5-C20 heterocyclo;
- and
- wherein R5 and R6 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, and C5-C20 heterocyclo.
6 more elements
A process for alkylating a 1,3-benzenediamine compound comprising:
- providing a first carbonyl compound selected from the group consisting of an aldehyde having the general formula:
- and a ketone having the general formula:
- wherein R10 and R11 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, C5-C20 heterocyclo and a ring compound found by fusing R10 and R11 to form a C4-C20 cycloalkyl, C5-C20 aryl, or C5-C20 heterocyclo;
- providing a second carbonyl compound selected from an aldehyde having the general formula:
- and a ketone having the general formula:
- wherein R10 and R11 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, C5-C20 heterocyclo and a ring compound formed by fusing R10 and R11 to form a C4-C20 cycloalkyl, C5-C20 aryl, or C5-C20 heterocyclo, wherein the first carbonyl compound is different than the second carbonyl compound;
- reacting the first carbonyl compound with a 1,3-benzenediamine compound in the presence of hydrogen and a hydrogenation catalyst to form an intermediate having a general formula selected from the group consisting of:
- and
- reacting the second carbonyl compound with the intermediate compound in the presence of hydrogen and a hydrogenation catalyst to form the alkylated 1,3-benzenediamine compound having a general formula selected from the group consisting of:
- wherein Z=H, and a=0, 1, or 2.
7 more elements
A lubricating oil composition, comprising:
- at least one base stock of lubricating viscosity in an amount from 80 wt % to 99.99 wt %, based on the total mass of the composition;
- and
- an antioxidant in an amount from 0.01 wt % to 6 wt % based on the total mass of the composition, the antioxidant comprising at least one compound having a structure (I) having the general formula:
- wherein R1 and R2 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, C5-C20 heterocyclo and hydrogen, provided that at least one of R1 and R2 is not hydrogen;
- wherein R3 and R4 are independently selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, and C5-C20 heterocyclo;
- and
- wherein R5 and R6 are independently selected from the group consisting of hydrogen, C1-C20 alkyl, C2-C20 alkenyl, C4-C20 cycloalkyl, C5-C20 aryl, and C5-C20 heterocyclo.
4 more elements
A N1,N3-dialkyl-4,6-dialkyl-1,3-benzenediamine.
A lubricating oil composition, comprising:
- at least one base stock of lubricating viscosity in an amount from 80 wt % to 99.99 wt %, based on the total mass of the composition;
- and
- a N1,N3-dicycloalkyl-4,6-dialkyl-1,3-benzenediamine in an amount from 0.01 wt % to 6 wt % based on the total mass of the composition.
Dependencies are inferred from the claim text.