HYDROLYIS OF OIL-DISPERSED AMINE SALTS
NAVAL RESEARCH LAB WASHINGTON DC
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The water insoluble reaction products between a series of amines and phenylstearic acid and dinonylnaphthalenesulfonic acid were chosen as structurally determinate prototypes of ashless salt rust inhibitors. The stabilities of such additives dissolved in an organic phase in contact with aqueous phases of varying pH and CO2 content were investigated. Results were reported as percent hydrolysis, i.e., percent of nitrogen originally present in the organic phase that was found in the aqueous phase at the termination of the reaction. Salt stability depends on an acid displacement mechanism wherein a strong acid displaces the anion conjugate of weaker acid from its salt. The extent to which the amine component of the amine phenylstearate salts is extracted by water parallels the water solubility of the amine component. The effect is further enhanced by the presence of carbon dioxide. The amine component of the amine dinonylnaphthalene sulfonates is extracted by water only in trace amounts even in the presence of carbon dioxide. The presence of acids stronger than carbonic acid in the aqueous phase may result in complete destruction of the amine phenylstearate and in substantial depletion of amine from solutions of amine dinonylnaphthalene sulfonates.
- Organic Chemistry