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Title: The thermodynamic properties of 2-aminobiphenyl (an intermediate in the carbazole/hydrogen reaction network)

Abstract

Catalytic hydrodenitrogenation (HDN) is a key step in upgrading processes for conversion of heavy petroleum, shale oil, tar sands, and the products of the liquefaction of coal to economically viable products. This research program provides accurate experimental thermochemical and thermophysical properties for key organic nitrogen-containing compounds present in the range of alternative feedstocks, and applies the experimental information to thermodynamic analyses of key HDN reaction networks. This report is the first in a series that will lead to an analysis of a three-ring HDN system; the carbazole/hydrogen reaction network. 2-Aminobiphenyl is the initial intermediate in the HDN pathway for carbazole, which consumes the least hydrogen possible. Measurements leading to the calculation of the ideal-gas thermodynamic properties for 2-aminobiphenyl are reported. Experimental methods included combustion calorimetry, adiabatic heat-capacity calorimetry, comparative ebulliometry, inclined-piston gauge manometry, and differential-scanning calorimetry (d.s.c). Entropies, enthalpies, and Gibbs energies of formation were derived for the ideal gas for selected temperatures between 298.15 K and 820 K. The critical temperature and critical density were determined for 2-aminobiphenyl with the d.s.c., and the critical pressure was derived. The Gibbs energies of formation are used in thermodynamic calculations to compare the feasibility of the initial hydrogenolysis step in the carbazole/H{submore » 2} network with that of its hydrocarbon and oxygen-containing analogous; i.e., fluorene/H{sub 2} and dibenzofuran/H{sub 2}. Results of the thermodynamic calculations are compared with those of batch-reaction studies reported in the literature. 57 refs., 8 figs., 18 tabs.« less

Authors:
; ; ;
Publication Date:
Research Org.:
National Energy Technology Lab. (NETL), Bartlesville, OK (United States). National Inst. for Petroleum and Energy Research (NIPER)
Sponsoring Org.:
DOE/FE
OSTI Identifier:
6307021
Report Number(s):
NIPER-482
ON: DE91002209
DOE Contract Number:  
FC22-83FE60149
Resource Type:
Technical Report
Country of Publication:
United States
Language:
English
Subject:
02 PETROLEUM; 01 COAL, LIGNITE, AND PEAT; 04 OIL SHALES AND TAR SANDS; AMINES; THERMODYNAMIC PROPERTIES; BITUMENS; DESULFURIZATION; COAL LIQUIDS; PETROLEUM; SHALE OIL; BENZOFURANS; BIPHENYL; CALORIMETRY; CARBAZOLES; CHEMICAL REACTION KINETICS; COMPARATIVE EVALUATIONS; CRITICAL PRESSURE; CRITICAL TEMPERATURE; CRYSTALLIZATION; DATA; DENSITY; ENTHALPY; ENTROPY; EVAPORATION; FLUORENE; FORMATION FREE ENERGY; HIGH TEMPERATURE; HYDROGENATION; MEASURING METHODS; MEDIUM TEMPERATURE; MELTING; PHASE TRANSFORMATIONS; REACTION INTERMEDIATES; SPECIFIC HEAT; VAPOR PRESSURE; AROMATICS; AZAARENES; AZOLES; CHEMICAL REACTIONS; CONDENSED AROMATICS; ENERGY; ENERGY SOURCES; FLUIDS; FOSSIL FUELS; FREE ENERGY; FUELS; FURANS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; INFORMATION; KINETICS; LIQUIDS; MINERAL OILS; OILS; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANIC OXYGEN COMPOUNDS; OTHER ORGANIC COMPOUNDS; PHYSICAL PROPERTIES; REACTION KINETICS; TAR; TRANSITION TEMPERATURE; 020400* - Petroleum- Processing; 010402 - Coal, Lignite, & Peat- Purification & Upgrading; 040404 - Oil Shales & Tar Sands- Purification

Citation Formats

Steele, W V, Chirico, R D, Knipmeyer, S E, and Nguyen, A. The thermodynamic properties of 2-aminobiphenyl (an intermediate in the carbazole/hydrogen reaction network). United States: N. p., 1990. Web. doi:10.2172/6307021.
Steele, W V, Chirico, R D, Knipmeyer, S E, & Nguyen, A. The thermodynamic properties of 2-aminobiphenyl (an intermediate in the carbazole/hydrogen reaction network). United States. https://doi.org/10.2172/6307021
Steele, W V, Chirico, R D, Knipmeyer, S E, and Nguyen, A. 1990. "The thermodynamic properties of 2-aminobiphenyl (an intermediate in the carbazole/hydrogen reaction network)". United States. https://doi.org/10.2172/6307021. https://www.osti.gov/servlets/purl/6307021.
@article{osti_6307021,
title = {The thermodynamic properties of 2-aminobiphenyl (an intermediate in the carbazole/hydrogen reaction network)},
author = {Steele, W V and Chirico, R D and Knipmeyer, S E and Nguyen, A},
abstractNote = {Catalytic hydrodenitrogenation (HDN) is a key step in upgrading processes for conversion of heavy petroleum, shale oil, tar sands, and the products of the liquefaction of coal to economically viable products. This research program provides accurate experimental thermochemical and thermophysical properties for key organic nitrogen-containing compounds present in the range of alternative feedstocks, and applies the experimental information to thermodynamic analyses of key HDN reaction networks. This report is the first in a series that will lead to an analysis of a three-ring HDN system; the carbazole/hydrogen reaction network. 2-Aminobiphenyl is the initial intermediate in the HDN pathway for carbazole, which consumes the least hydrogen possible. Measurements leading to the calculation of the ideal-gas thermodynamic properties for 2-aminobiphenyl are reported. Experimental methods included combustion calorimetry, adiabatic heat-capacity calorimetry, comparative ebulliometry, inclined-piston gauge manometry, and differential-scanning calorimetry (d.s.c). Entropies, enthalpies, and Gibbs energies of formation were derived for the ideal gas for selected temperatures between 298.15 K and 820 K. The critical temperature and critical density were determined for 2-aminobiphenyl with the d.s.c., and the critical pressure was derived. The Gibbs energies of formation are used in thermodynamic calculations to compare the feasibility of the initial hydrogenolysis step in the carbazole/H{sub 2} network with that of its hydrocarbon and oxygen-containing analogous; i.e., fluorene/H{sub 2} and dibenzofuran/H{sub 2}. Results of the thermodynamic calculations are compared with those of batch-reaction studies reported in the literature. 57 refs., 8 figs., 18 tabs.},
doi = {10.2172/6307021},
url = {https://www.osti.gov/biblio/6307021}, journal = {},
number = ,
volume = ,
place = {United States},
year = {Sat Dec 01 00:00:00 EST 1990},
month = {Sat Dec 01 00:00:00 EST 1990}
}