Synthesis and characterization of trans-2-(N-methyl-N-phenylamino) cyclohexanol for the fabrication of a novel high performance liquid chromatography column
An organic amine known as trans-2-(N-methyl-N-phenylamino)cyclohexanol, MPAC, was synthesized, resolved and used to make silica based Chiral Stationary Phases, CSPs. CSPs are capable of separating racemic mixtures of non-superimposable mirror images called enantiomers by interacting preferentially more with one enantiomer than the other. Single enantiomer drugs, collectively known as chiral drugs, have created enormous economic growth in excess of hundreds of billions of dollars in the area of pharmaceuticals and medicine. Three different methods were employed in the synthesis of CSPs. One method used MPAC bonded covalently to silica via a carbamate to make what is known as a Pirkle type column. Electron Diffraction Spectroscopy, EDS, confirmed the incorporation of MPAC onto silica, but this material did not separate racemic trans-cumylcyclohexanol, TCC, a chiral standard used throughout this study. Next, the laurate ester byproduct of the resolution of MPAC by Candida rugosa lipase was used as an ammonium template to form chiral zeolitic material after calcination. This material was not porous and did not separate racemic TCC. In the third approach, MPAC was used as an ammonium template to make chiral zeolitic material from sodium silicate after calcination. The optimum calcination temperature was found to be 550°C to make a most porous material. The porosity of this material was shown by Scanning Electron Microscopy, SEM. This material was capable of separating several racemic mixtures when packed into a High Performance Liquid Chromatography (HPLC) column. The MPAC/sodium silicate mole ratio and the packing of the column were studied.
Refaei, Mohd N, "Synthesis and characterization of trans-2-(N-methyl-N-phenylamino) cyclohexanol for the fabrication of a novel high performance liquid chromatography column" (2007). ETD Collection for University of Texas, El Paso. AAI3262909.