Permethylated tertiary polyamines

To avoid confusion in describing polyamine separations, Table I shows skeletal structural formulas of the isomeric and homologous polyethylene polyamines. Included with each formula is a derived abbreviation corresponding to the N-permethylated tertiary amine counterpart of the particular structure. The abbreviations are based on the homologous relationship of the N-permethylated structures to the first member of the series, N,N,N, N -tetramethylethylenediamine, or TMED (Compound 1,... 

Dissociation of the polyamine salt adduct must be achieved to liberate the salt and recover the polyamine. With complexes of the N-permethylated polyethylene polyamines, it is convenient (on a small scale) to dissociate the complex by dissolving it in aqueous potassium hydroxide. The tertiary polyamine is generally extracted from this mixture without difficulty. Dissolution of the complexes containing primary polyamines likewise leads to dissociation. However, high solubility of the primary polyamines in water creates a recovery problem. With complexes containing primary amine functions, it is preferable, and generally... 

The same type of dissociation technique may be used to recover N-permethylated polyamines from their metal-salt complexes. The solvent is the major factor to be considered in designing such a procedure. The solvent chosen should boil near or slightly above the thermal dissociation temperature of the particular polyamine salt complex. With N-permethylated polyethylene polyamines, the final recovery of a polyamine from the extraction solvent is best done by distilling the hydrocarbon solution. Recovery by phase separation is not possible with the tertiary polyamines since these compounds generally are miscible with most hydrocarbon solvents. 

The preferred chelating agents are derivatives of ethylenediamine, higher polyamines, and isomers. The particular tertiary chelating polyamines discussed here together with their abbreviations are (they are all permethylated polyamines) ... 

Permethylation has been applied to the determination of polyamines. Permethyl derivatives eliminate the polar NH groups but retain the troublesome adsorptive properties of tertiary amines. 

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