Lauryl lactam, the nylon 12 monomer, can bc manufactured by an oxime rearrangement analogous to that used for caprolactam. Initially the cyclododecanolkyclodecanone mixture, as in the manufacture of 1,12-dodccancdioic acid, is dehydrogenatcd in the liquid phase at 230-245 °C and atrnospheric pressure in the presence of Cu/Al₂O₃ or Cu/Cr catalysts to give an almost quantitative yield of cyclododccanone:

Cyclododccanone is then oximatcd and the rearrangcmcnt is carried out in oleum at 100 to 130°C: 图29
Since lauryl lactam is insoluble in water, the neutralization step is unnccessary; the lactam can be scparated by dilution with H2O.

All three proccss steps have convcrsions of 95-100%, with selectivities of over 98%. Commercial processes are opcrated by Hüls and Nikon Rilsan.

A second pathway to lauryl lactam or its oxime precursor involves the photochemically initiated reaction of NOCl with cyclododecane at 70°C. Cyclododecane is easily obtained commercially by the trimcrization of butadiene to cyclododecatriene, which is then hydrogenated:



The conversion is almost 70%, with a selectivity of 88%.

This process is practiced in France by Aquitaine Organico (ATO) in an 8000 tonne-per-year plant.

Snia Viscosa's caprolactam manufacturing process can also be used for the reaction of eyclododccanecarboxylic acid with nitrosylsulfuric acid. Lauryl lactam is obtained directly:

A newer process is based on initial research by BP, with further development by Ube Industries, in which cyclohexanonc in the presence of NH₃ is converted to 1,1'-pcroxydicyclohexylamine in a catalytic peroxidation:

The reaction product is separated as an oily phase from the two-phase mixture, washed, and dissociated to w-cyanoundccanoic acid in a pyrolysis reactor in the presence of steam. Byproducts are ε-caprolactam and cyclohexanone. The purified crystalline ω-cyanoundecanoic acid is dissolved in a solvent and catalytically hydrogenated to ω-aminododecanoic acid, which is then purified by crystallization:

Further details of this process have not been disclosed.

Ube currently operates a plant whose capacity has been expanded to 3000 tonnes per year.