FIELD: chemistry.
SUBSTANCE: invention relates to a method of producing alkylated 1,3-benzenediamine compounds of structural formula II. The alkylated 1,3-benzenediamine compound is used as a deposit growth inhibiting additive for lubricating oil for organic materials containing lubricating oil, gasoline and diesel fuel. The method of alkylating a 1,3-benzenediamine compound involves reacting a first carbonyl compound with a 1,3-benzediamine compound to form an intermediate compound, where the first carbonyl compound is substituted on the corresponding nitrogen atoms of 1,3-benzenediamine, and reacting a second carbonyl compound with said intermediate compound in the presence of hydrogen and a hydrogenation catalyst to form alkylated 1,3-benzenediamine, where the second carbonyl compound is substituted on the central aromatic ring of the alkylated 1,3-benzenediamine. The alkylated 1,3-benzenediamine has the structure (II) of general formula: (I), in which R1 and R2 are independently selected from a group consisting of hydrogen, C1-C20 alkyl, 2-methylpropenyl, benzyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; R3 and R4 are independently selected from a group consisting of C1-C20 alkyl, 2-methylpropenyl, benzyl, cyclopentyl, cyclohexyl, cycloheptyl and cycloocty; and R5 and R6 are independently selected from a group consisting of n-propyl, 1-methylethyl, n-butyl, isobutyl, sec-butyl, 1,3-dimethylbutyl, 1,4-dimethylpentyl, n-pentyl, isopentyl, 1,5-dimethylhexyl, hexyl, 2-methylpropenyl, benzyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and hydrogen, under the condition that at least one of R5 and R6 is not hydrogen.
EFFECT: method increases selectivity of alkylation on amino groups and the benzene ring; obtained compounds improve oxidation resistance of lubricant substances and fuel.
5 cl, 5 tbl, 21 ex
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Authors
Dates
2013-09-20—Published
2008-12-01—Filed