Nitrogen-containing aromatic compounds: quantitative analysis using gas chromatography with nitrogen phosphorus detector
Tóm tắt
The nitrogen-containing aromatic compounds found in the petrochemical industry are varied and extend beyond classes such as the anilines, pyrroles and pyridines. Quantification of these nitrogen-containing compounds that may occur in complex mixtures has practical application for quality assurance, process development and the evaluation of conversion processes. Selective detection of nitrogen-containing species in complex mixtures is possible by making use of gas chromatography coupled with a nitrogen phosphorous detector (GC-NPD), which is also called a thermionic detector. Despite the linearity of the NPD response to individual nitrogen-containing compounds, the response factor is different for different compounds and even isomers of the same species. Quantitative analysis using an NPD requires species-specific calibration. The reason for the sensitivity of the NPD to structure is related to the ease of forming the cyano-radical that is ionized to the cyanide anion, which is detected. The operation of the NPD was related to the processes of pyrolysis and subsequent ionization. It was possible to offer plausible explanations for differences in response factors for isomers based on pyrolysis chemistry. Due to this relationship, the NPD response can in the same way be used to provide information of practical relevance beyond its analytical value and a few possible applications were outlined.
Tài liệu tham khảo
Waddams AL (1973) Chemicals from petroleum, 3rd edn. John Murray, London, pp 209–212
Goe GL (1982) Pyridine and pyridine derivatives. Kirk-Othmer encyclopedia of chemical technology, 3rd edn, vol 19. Wiley, New York, pp 454–483
Kaiser MJ, De Klerk A, Gary JH, Handwerk GE (2020) Petroleum refining. Technology, economics, and markets, 6th edn. CRC Press, Boca Raton
Prado GHC, Rao Y, De Klerk A (2017) Nitrogen removal from oil: a review. Energy Fuels 31:14–36
Albert DK (1978) Determination of nitrogen compound distribution in petroleum by gas chromatography with a thermionic detector. Anal Chem 50:1822–1829
Bakel AJ, Philip RP (1990) The distribution and quantitation of organonitrogen compounds in crude oils and rock pyrolysates. Org Geochem 16:353–367
Frame GM, Carmody DC, Flanigan GA (1978) An atlas of gas chromatograms of oils using dual flame-ionization and nitrogen phosphorus detectors. Report of the United States Coast Guard Research and Development Center, CGR/DC-3/78, USCG-D-A054966
Li N, Ma X, Zha Q, Song C (2010) Analysis and comparison of nitrogen compounds in different liquid hydrocarbon streams derived from petroleum and coal. Energy Fuels 24:5539–5547
Machado ME (2019) Comprehensive two-dimensional gas chromatography for the analysis of nitrogen-containing compounds in fossil fuels: a review. Talanta 198:263–276
Von Mühlen C, De Oliveira EC, Morrison PD, Zini CA, Caramão EB, Marriott PJ (2007) Qualitative and quantitative study of nitrogen containing compounds in heavy gas oil using comprehensive two-dimensional gas chromatography with nitrogen phosphorus detection. J Sep Sci 30:3223–3232
Poole CF (2015) Ionization-based detectors for gas chromatography. J Chromatogr A 1421:137–153
Kolb B, Bischoff J (1974) A new design of a thermionic nitrogen and phosphorus detector for GC. J Chromatogr Sci 12:625–629
Carlsson H, Robertsson G, Colmsjö A (2001) Response mechanisms of thermionic detectors with enhanced nitrogen selectivity. Anal Chem 73:5698–5703
Sternberg JC, Gallaway WS, Jones DTL (1962) The mechanism of response of flame ionization detectors. In: Brenner N, Callen JE, Weiss MD (eds) Gas chromatography. Academic Press, New York, pp 231–267
Scanlon JT, Willis DE (1985) Calculation of flame ionization detector relative response factors using the effective carbon number concept. J Chromatogr Sci 23:333–340
Jorgensen AD, Picel KC, Stamoudis VC (1990) Prediction of gas chromatography flame ionization detector response factors from molecular structures. Anal Chem 62:683–689
Katritzky AR, Ignatchenko ES, Barcock RA, Lobanov VS, Karelson M (1994) Prediction of gas chromatographic retention times and response factors using a general qualitative structure-property relationships treatment. Anal Chem 66:1799–1807
Tenenbaum LE (1961) Alkylpyridines and arylpyridines. In: Klingsberg E (ed) Pyridine and its derivatives. Part II. Interscience, New York, pp 155–298
Hurd CD, Simon JI (1962) Pyrolytic formation of arenes. III. Pyrolysis of pyridine, picolines and methylpyrazine. J Am Chem Soc 84:4519–4524
Mackie JC, Colket MB III, Nelson PF (1990) Shock tube pyrolysis of pyridine. J Phys Chem 94:4099–4106
Terentis A, Doughty A, Mackie JC (1992) Kinetics of pyrolysis of a coal model compound, 2-picoline, the nitrogen heteroaromatic analogue of toluene. 1. Product distributions. J Phys Chem 96:10334–10339
Doughty A, Mackie JC (1992) Kinetics of pyrolysis of a coal model compound, 2-picoline, the nitrogen heteroaromatic analogue of toluene. 2. The 2-picolyl radical and kinetic modeling. J Phys Chem 96:10339–10348
Ikeda E, Mackie JC (1995) Thermal decomposition of two coal model compounds—pyridine and 2-picoline. Kinetics and product distributions. J Anal Appl Pyrolysis 34:47–63
Jones J, Bacskay GB, Mackie JC (1996) The pyrolysis of 3-picoline: ab initio quantum chemical and experimental (shock tube) kinetic studies. Isr J Chem 36:239–248
Memon HUR, Bartle KD, Taylor JM, Williams A (2000) The shock tube pyrolysis of pyridine. Int J Energy Res 24:1141–1159
Blanksby SJ, Ellison GB (2003) Bond dissociation energies of organic molecules. Acc Chem Res 36:255–263
Moreea-Taha R (2000) NOx modelling and prediction. IEA Coal Research, London, p 12