Addition Reactions of Olefins to Asphaltene Model Compounds

  • Author / Creator
    Cardozo, Samuel D.
  • Two alkyl-bridged aromatic compounds, with molecular weights of 899.70 g/mol and 1127.99 g/mol, were thermally cracked with 1-hexadecene, 1- octadecene, or trans-stilbene, in a batch microreactor at 375–430 °C for 15 to 45 min. The objective of the study was to investigate the kinetics of the addition reactions between the olefins and asphaltene model compounds. Reaction products were analyzed by gas chromatography, high-performance liquid chromatography, matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS), and proton nuclear magnetic resonance (1H-NMR) spectroscopy. Kinetic data indicate a first-order reaction in model compound concentration, with energetics consistent with a free-radical chain mechanism. Tandem MS/MS and 1H-NMR spectra of the products are consistent with olefin addition through the alkyl bridge of the bridged aromatics. The results imply that the addition products are able to abstract hydrogen to give detectable products faster than they decompose, and that they can react even more readily than the parent compounds.

  • Subjects / Keywords
  • Graduation date
    Fall 2013
  • Type of Item
  • Degree
    Master of Science
  • DOI
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.