Tertiary alkyldimethylamines

Direct conversion of fatty alcohols to primary amines by reaction with ammonia is not commercially practised but new catalyst developments show improved yields with this technology [10]. However, production of dialkylamines from alcohols is practised particularly with C8-C10 alcohols due to the limited availability of the corresponding acids. Alcohols are commonly used in the manufacture of tertiary alkyldimethylamines either through reductive amination with dimethylamine or by conversion to the alkylhaUde followed by reaction with dimethylamine. Both primary and secondary amines can be reacted with alcohols to produce tertiary trialkyl amines [11]. The chain branching seen with some synthetic alcohols means that the derived amines are not identical to those from natural sources. 

Reductive alkylation of nitrile by secondary amines having the same or different alkyl chains is another alternative for tertiary amine preparation. Many other special cationics, N-alkyl monoaza crown ethers [53], for example, can be classified as tertiary amines. The surface-active tertiary amine compounds are used as such (as corrosion inhibitors, dopes, antistatics, reagents in mineral processing) or as semifinished products. Alkyldimethylamines and dialkylmethylamines were run on a commercial level, e.g., by Albemarle (former Ethyl Corp.) as ADMA Tertiary Amines and DAMA Tertiary Amines , respectively. 

The minimum effective chain length allowing amines to be quantitatively titrated by dodecylsulfate is 12 carbons, or 10 in the case of alkyldimethylamines titrated with tetradecylsulfate. This is true of both two-phase indicator titration and one-phase potentiometric titration. If the titrant is tetraphenylborate rather than an alkyl sulfate, the effective chain length need only be 8 for tertiary symmetric amines, while all quaternaries are titrated (87). The effective chain length concept corrects for overlapping of alkyl chains, so... 

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