Challenge in the speciation of nitrogen-containing compounds in heavy petroleum fractions by high temperature comprehensive two-dimensional gas chromatography.

Extending the knowledge related to nitrogen-containing compounds presents an important interest for the petroleum industry due to their implication in atmosphere pollution as well as their inhibitive or refractive behaviour towards hydroprocessing. Most of the nitrogenated species are concentrated in heavy petroleum cuts. As no analytical method is resolutive enough for these heavy cuts, particularly regarding nitrogen-containing compounds, a new approach is needed. For this reason, this study focuses on the development of a GC×GC technique, through the hyphenation of a specific NCD detector with a GC×GC system at high temperature. The performances of highly polar thermally stable stationary phases, in particular those composed of promising ionic liquids, were monitored in normal and reversed configurations. Subsequently, after the extraction of neutral or basic compounds by adsorption on an ion-exchange resin, a first quantitative determination was attempted for a straight-run and a direct coal liquefaction vacuum gas oils. This study led to a better understanding of the behaviour of highly aromatic N-compounds by 2D-GC including an ionic liquid phase as well as a deeper N-characterization of heavy petroleum fractions.

[1]  M. Hennion,et al.  Supercritical fluid chromatography hyphenated with twin comprehensive two-dimensional gas chromatography for ultimate analysis of middle distillates. , 2010, Journal of chromatography. A.

[2]  M. Hennion,et al.  High-temperature two-dimensional gas chromatography of hydrocarbons up to nC60 for analysis of vacuum gas oils. , 2009, Journal of chromatography. A.

[3]  Richard B. Gaines,et al.  Temperature requirements for thermal modulation in comprehensive two-dimensional gas chromatography. , 2004, Journal of separation science.

[4]  U. Brinkman,et al.  Comprehensive two-dimensional gas chromatography with atomic emission detection and correlation with mass spectrometric detection: principles and application in petrochemical analysis. , 2003, Journal of chromatography. A.

[5]  D. Armstrong,et al.  Immobilized ionic liquids as high-selectivity/high-temperature/high-stability gas chromatography stationary phases. , 2005, Analytical chemistry.

[6]  M. Hennion,et al.  Improved hydrocarbons analysis of heavy petroleum fractions by high temperature comprehensive two-dimensional gas chromatography , 2010 .

[7]  Paul T. Williams,et al.  Aromatic and hetero-aromatic compositional changes during catalytic hydrotreatment of shale oil , 1999 .

[8]  D. Espinat,et al.  Physicochemical Characterization of Petroleum Fractions: the State of the Art , 2007 .

[9]  D. Armstrong,et al.  Trigonal tricationic ionic liquids: a generation of gas chromatographic stationary phases. , 2009, Analytical chemistry.

[10]  J. Zumberge,et al.  Detailed compositional comparison of acidic NSO compounds in biodegraded reservoir and surface crude oils by negative ion electrospray Fourier transform ion cyclotron resonance mass spectrometry , 2007 .

[11]  C. Lopez-Garcia,et al.  Kinetic Modeling of Vacuum Gas Oil Hydrotreatment using a Molecular Reconstruction Approach , 2011 .

[12]  P. Fischer,et al.  Analysis of high-boiling petroleum streams by high-resolution mass spectrometry. , 1974, Talanta.

[13]  P. Marriott,et al.  Development of a resolution metric for comprehensive two-dimensional chromatography. , 2007, Journal of chromatography. A.

[14]  M. Rodrigues,et al.  Identification of alkyl carbazoles and alkyl benzocarbazoles in Brazilian petroleum derivatives. , 2006, Journal of chromatography. A.

[15]  M. Santra,et al.  Effects of organic nitrogen compounds on hydrotreating and hydrocracking reactions , 2005 .

[16]  J. Vial,et al.  Pharmaceutical quality of docetaxel generics versus originator drug product: a comparative analysis , 2008 .

[17]  U. Brinkman,et al.  Simple, non-moving modulation interface for comprehensive two-dimensional gas chromatography. , 2001, Journal of chromatography. A.

[18]  P. Marriott,et al.  Qualitative and quantitative study of nitrogen-containing compounds in heavy gas oil using comprehensive two-dimensional gas chromatography with nitrogen phosphorus detection. , 2007, Journal of separation science.

[19]  C. Cordero,et al.  Comprehensive two-dimensional gas chromatography in the analysis of volatile samples of natural origin: a multidisciplinary approach to evaluate the influence of second dimension column coated with mixed stationary phases on system orthogonality. , 2006, Journal of chromatography. A.

[20]  D. Armstrong,et al.  Increasing selectivity in comprehensive three-dimensional gas chromatography via an ionic liquid stationary phase column in one dimension. , 2010, Journal of chromatography. A.

[21]  J. Beens,et al.  Chapter 7 Petrochemistry , 2009 .

[22]  Johanna Smeyers-Verbeke,et al.  Handbook of Chemometrics and Qualimetrics: Part A , 1997 .

[23]  G. G. Stokes "J." , 1890, The New Yale Book of Quotations.

[24]  Hernan J Cortes,et al.  Comprehensive two dimensional gas chromatography review. , 2009, Journal of separation science.

[25]  Guy Marin,et al.  Challenges of Modeling Steam Cracking of Heavy Feedstocks , 2007 .

[26]  E. Caramão,et al.  Ion-exchange resins in the isolation of nitrogen compounds from petroleum residues. , 2004 .

[27]  M. Hennion,et al.  Comprehensive two-dimensional gas chromatography for basic and neutral nitrogen speciation in middle distillates , 2009 .

[28]  P. Schoenmakers,et al.  Gas chromatographic methods for oil analysis. , 2002, Journal of chromatography. A.

[29]  D. Armstrong,et al.  Comprehensive two-dimensional gas chromatography using a high-temperature phosphonium ionic liquid column , 2008, Analytical and bioanalytical chemistry.

[30]  G. Derringer,et al.  Simultaneous Optimization of Several Response Variables , 1980 .

[31]  P. Marriott,et al.  Characterization of nitrogen-containing compounds in heavy gas oil petroleum fractions using comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry , 2010 .

[32]  F. Jiménez,et al.  Modeling of industrial reactor for hydrotreating of vacuum gas oils Simultaneous hydrodesulfurization, hydrodenitrogenation and hydrodearomatization reactions , 2007 .

[33]  W. Robbins,et al.  Speciation of nitrogen-containing compounds in diesel fuel by comprehensive two-dimensional gas chromatography. , 2004, Journal of separation science.

[34]  M. Hennion,et al.  New benchmark for basic and neutral nitrogen compounds speciation in middle distillates using comprehensive two-dimensional gas chromatography. , 2007, Journal of chromatography. A.

[35]  M. Hennion,et al.  Extended characterization of a vacuum gas oil by offline LC-high-temperature comprehensive two-dimensional gas chromatography. , 2010, Journal of separation science.

[36]  Norman C. Li,et al.  Role of nitrogen- and sulphur-containing compounds in the ageing of liquid fuels , 1985 .

[37]  L. Fang,et al.  Germania-based, sol-gel hybrid organic-inorganic coatings for capillary microextraction and gas chromatography. , 2007, Analytical chemistry.

[38]  Philip Marriott,et al.  Orthogonality considerations in comprehensive two-dimensional gas chromatography. , 2005, Journal of chromatography. A.

[39]  J. Jose,et al.  Specific Nitrogen Boiling Point Profiles of Vacuum Gasoils , 2005 .

[40]  D. Armstrong,et al.  Characterization and utilization of a novel triflate ionic liquid stationary phase for use in comprehensive two-dimensional gas chromatography. , 2008, Journal of separation science.

[41]  J. Giddings Concepts and comparisons in multidimensional separation , 1987 .