Thermodynamics Research Center / ThermoML | Journal of Chemical and Engineering Data

Melting points of potential liquid organic hydrogen carrier systems consisting of N-alkylcarbazoles

Stark, K.[Katharina], Keil, P.[Philipp], Schug, S.[Sebastian], Muller, K.[Karsten], Wasserscheid, P.[Peter], Arlt, W.[Wolfgang]
J. Chem. Eng. Data 2016, 61, 4, 1441-1448
ABSTRACT
Liquid organic hydrogen carrier represent an attractive concept of storing hydrogen by the hydrogenation of usually aromatic compounds. One of the best investigated LOHCs is N-ethylcarbazole because of its favourable thermodynamic properties. However, its high melting point of 343.1 K could be a major drawback particularly in mobile applications. Therefore it is desired to decrease the melting point of N-ethylcarbazole without significantly changing favourable properties like the storage density or the reaction behavior of the carrier compound. In order to investigate the solid-liquid behavior during hydrogenation, the melting points of pure N-ethylcarbazole derivatives with increasing degree of hydrogenation as well as the liquidus line of the binary mixture of Nethylcarbazole and N-ethyl-dodecahydro-carbazole were measured. Due to their structural and chemical resemblance binary mixtures consisting of different alkylcarbazole combinations were analyzed regarding their potential for a melting point depression. By the appropriate combination of N-alkylcarbazoles, it is possible to achieve a considerable melting point decrease to 297.1 K.
Compounds
# Formula Name
1 C12H9N 9H-carbazole
2 C12H13N 2,3,4,9-tetrahydro-1H-carbazole
3 C13H11N 9-methyl-9H-carbazole
4 C14H13N 9-ethylcarbazole
5 C15H15N N-propyl-9H-carbazole
6 C15H15N 9-(1-methylethyl)carbazole
7 C16H17N N-butyl-9H-carbazole
8 C14H17N 9-ethyl-2,3,4,9-tetrahydrocarbazole
9 C14H21N 9-ethyl-2,3,4,5,6,7,8,9-octahydro-1H-carbazole
10 C14H25N (4aR,4bS,8aS,9aR)-rel-9-ethyldodecahydrocarbazole
Datasets
The table above is generated from the ThermoML associated json file (link above). POMD and RXND refer to PureOrMixture and Reaction Datasets. The compound numbers are included in properties, variables, and phases, if specificied; the numbers refer to the table of compounds on the left.
Type Compound-# Property Variable Constraint Phase Method #Points
  • POMD
  • 1
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 1
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 2
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 2
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 3
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 3
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 4
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 5
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 5
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 6
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 6
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 7
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 7
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 8
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 8
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 9
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 9
  • Molar enthalpy of transition or fusion, kJ/mol ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DSC
  • 1
  • POMD
  • 10
  • Normal melting temperature, K ; Crystal
  • Crystal
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 1
  • Eutectic temperature, K ; Crystal - 4
  • Crystal - 4
  • Crystal - 1
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 1
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 1
  • DTA
  • 10
  • POMD
  • 4
  • 3
  • Eutectic temperature, K ; Crystal - 4
  • Crystal - 4
  • Crystal - 3
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 3
  • DTA
  • 4
  • POMD
  • 4
  • 3
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • DTA
  • 3
  • POMD
  • 4
  • 5
  • Eutectic temperature, K ; Crystal - 4
  • Crystal - 4
  • Crystal - 5
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • DTA
  • 5
  • POMD
  • 4
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • DTA
  • 5
  • POMD
  • 4
  • 6
  • Eutectic temperature, K ; Crystal of intercomponent compound 1
  • Crystal of intercomponent compound 1
  • Crystal - 6
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 6
  • Eutectic temperature, K ; Crystal of intercomponent compound 1
  • Crystal of intercomponent compound 1
  • Crystal - 4
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 6
  • DTA
  • 7
  • POMD
  • 4
  • 6
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal of intercomponent compound 1
  • DTA
  • 6
  • POMD
  • 4
  • 7
  • Eutectic temperature, K ; Crystal - 4
  • Crystal - 4
  • Crystal - 7
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 4
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • DTA
  • 3
  • POMD
  • 4
  • 7
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • DTA
  • 3
  • POMD
  • 7
  • 5
  • Eutectic temperature, K ; Crystal - 5
  • Crystal - 5
  • Crystal - 7
  • Liquid
  • Air at 1 atmosphere
  • DTA
  • 1
  • POMD
  • 7
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 7
  • DTA
  • 9
  • POMD
  • 7
  • 5
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 5; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 5
  • DTA
  • 5
  • POMD
  • 4
  • 10
  • Solid-liquid equilibrium temperature, K ; Liquid
  • Mole fraction - 4; Liquid
  • Pressure, kPa; Liquid
  • Liquid
  • Crystal - 4
  • DTA
  • 13