Notes- The Structure of "Acetone Anil," 2,2,4-Trimethyl-1,2-dihydroquinoline.

Characterization of low molecular weight polymers by liquid chromatography and field desorption mass spectroscopy

“…The monomer 2,2,4-trimethyl-1,2-dihydroquinoline (TMDQ) is prepared by the acid-catalyzed condensation of aniline with acetone (9). The structure of the monomeric condensation product has been verified spectroscopically (10)(11)(12). After purification of the monomer, the TMDQ may be polymerized to form a resinous product (poly-TMDQ).…”

Determination of the Synthetic Antioxidant Ethoxyquin and Its Metabolites in Fish and Fishery Products Using Liquid Chromatography–Fluorescence Detection and Stable-Isotope Dilution Analysis–Liquid Chromatography–Tandem Mass Spectrometry

“…Although the product of a rather simple condensation reaction, EQ’s exact chemical structure has puzzled researchers for many years. Initially referred to as “aceton- p -phenetidil” (i.e., the condensation product of p -phenetidine and acetone obtained in the presence of iodine), it was not until 1961 that Elliott and Yates were finally able to unambiguously identify its structure as 1,2-dihydro-2,2,4-trimethylquinoline, thus refuting the idea of “acetone anil” formation . Despite this problem, significant effort has been put into optimizing synthetic strategies for EQ production to meet industrial demand.…”