Multiple metal deactivators, method for preparing, and use thereof
AssigneeAshland Oil, Inc.
InventorTheodore C. Shields
Life of this patent
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Abstract
Disclosed is a reaction product and method for making same for use in suppressing the ability of solubilized copper, iron, cobalt, nickel, chromium and manganese present in hydrocarbon liquids, such as gasoline and fuel oil, to catalyze oxidative degradation. The reaction product is obtained by reacting 1,2-alkane diamine, a 2,4-dione and an ortho-hydroxy aromatic aldehyde, in stoichiometric proportions, preferably in an inert liquid medium. A preferred reaction product is that obtained by reacting ethylenediamine, 2,4-pentanedione and salicylaldehyde in a 1 to 1 to 1 mole ratio.
Claims12
A method for making a metal deactivator composition comprising:
- a. partially reacting in a liquid solvent at a temperature below about 200.degree. C., an aliphatic polyamine selected from the the group consisting of ethylenediamine, 1,2-propanediamine, 1,2-diaminocyclohexane, 2,3-diaminobutane, 1,3-propanediamine, 1,3-butanediamine, 2,4-pentanediamine, 1,6-hexanediamine, diethylenetriamine and mixtures of these, with a beta-diketone selected from the group consisting of 2,4-pentanedione, 2,2,6,6-tetramethyl-3,5-heptanedione, 2,6-dimethyl-3,5-heptanedione, 3,5-heptanedione, 2,4-hexanedione, 5-methyl-2,4-hexanedione and 5,5-dimethyl-2,4-hexanedione;
- and
- b. reacting the resulting product in a liquid organic solvent completely with salicylaldehyde at a temperature below about 60.degree. C., the mole ratio of said beta-diketone to said aliphatic polyamine of (a) being between about 0.6 to 1 and about 1.4 to 1, the mole ratio of said salicylaldehyde of (b) to said aliphatic polyamine of (a) being between about 1.4 to 1 and about 0.6 to 1, and the ratio of the total moles of said beta-diketone and said salicylaldehyde to the total moles of said ethylenediamine being about 2 to 1.
A method for making metal deactivator compositions comprising reacting a 1,2-polyamine selected from the group consisting of ethylenediamine, 1,2-propanediamine, 1,2-diaminocyclohexane, 2,3-diaminobutane, and mixtures thereof with a 1,3-polyamine selected from the group consisting of 1,3-propanediamine, 1,3-butanediamine, 2,4-pentanediamine and mixtures thereof, and subsequently reacting a beta-diketone selected from the group consisting of 2,4-pentanedione, 2,2,6,6-tetramethyl-3,5-heptanedione, 2,6-dimethyl-3,5-heptanedione, 2,4-hexanedione, 5-methyl-2,4-hexanedione and 5,5-dimethyl-2,4-hexanedione, said method further comprising;
- a. reacting the 1,2-polyamine with the beta-diketone in a mole ratio of said 1,2-polyamine to said diketone of about 1 to 1 at a temperature below 200.degree. C.
- b. adding the 1,3-polyamine to the reaction mixture thus obtained;
- c. reacting substantially to completion the 1,3-polyamine and unreacted 1,2-polyamine at a temperature below 60.degree. C. with an ortho-hydroxybenzaldehyde having the structural formula:
- ##STR10## where R and R' are hydrogen, or aliphatic hydrocarbons having a total of 0 to 12 carbon atoms;
- and
- d. recovering the liquid organic mixture resulting.
Dependencies are inferred from the claim text.