N -ethyl carbazole

Structural formula
General
Surname	N -ethyl carbazole
other names	1-ethyl carbazole 9-ethyl carbazole ECZ
Molecular formula	C 14 H 13 N
Brief description	brown solid
External identifiers / databases
CAS number 86-28-2 EC number 201-660-4 ECHA InfoCard 100.001.510 PubChem 6836 Wikidata Q291377
properties
Molar mass	195.27 g mol −1
Physical state	firmly
density	1.059 g cm −3 (80  ° C )
Melting point	68-70 ° C
boiling point	> 240 ° C
solubility	practically insoluble in water (0.03 mg l −1 at 20 ° C)
Refractive index	1.6394 (80 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 411 P: 273
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N -Ethylcarbazole is a chemical compound from the group of carbazole derivatives .

Extraction and presentation

N -Ethylcarbazole can be obtained by ethylating potassium carbazolate with diethyl sulfate .

properties

N -Ethylcarbazole is a flammable brown solid which is practically insoluble in water.

use

It is currently being investigated whether this compound or similar (such as N -methyl carbazole or phenylene carbazole ) in perhydro form as a liquid, pressureless hydrogen transport and storage media are suitable for vehicle propulsion with fuel cells or internal combustion engines. For this purpose, N -Ethylcarbazol under pressure and with the aid of a suitable catalyst (eg. Ruthenium or platinum ) at the site of hydrogen generation for perhydro-form hydrogenated :

${\displaystyle \mathrm {\ C_{14}H_{13}N+6\ H_{2}\ {\underset {>100\ ^{\circ }C}{\overset {Kat}{\rightleftharpoons }}}\ C_{14}H_{25}N} }$

This reaction can be reversed by heating the liquid perhydro compound to more than 100 ° C. In this way, the hydrogen can be recovered in the vehicle and used to drive the vehicle, with the waste heat from its oxidation ensuring the release of more hydrogen. The carbazole is returned to be recharged with hydrogen. The existing filling station network can continue to be used almost unchanged. The comparison with other energy densities is interesting .
When storing electrical energy with the help of N- ethyl carbazole, a significantly higher energy efficiency can be achieved than with comparable approaches such as the Sabatier process .

In addition, N- ethyl carbazole is used as a plasticizer .

During the First World War, a mixture of anthracene oil and N -ethyl carbazole was used as a nose and throat warfare agent in the blue cross grenade . N- ethyl carbazole acted as an irritant, which was supposed to trigger a sneeze and force the soldiers to take off their gas masks .

Individual evidence

1. ↑ ^{a b c d e f} Entry on N-Ethylcarbazole in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
2. ↑ ^{a b} David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-240.
3. ↑ Patent DE 255304, filed December 24, 1911 for N-methylcarbazole
4. ↑ Jason R. Buck, Minnie Park, Zhiwei Wang, Daniel R. Prudhomme, Carmelo J. Rizzo: 9-Ethyl-3,6-dimethylcarbazole (DMECZ) In: Organic Syntheses . 77, 2000, p. 153, doi : 10.15227 / orgsyn.077.0153 ( PDF ).
5. ↑ Carbazole: The Electric Gasoline? ( Memento of March 30, 2012 in the Internet Archive ), June 30, 2011, accessed on July 6, 2011.
6. ↑ Tom Grünweg: Alternative fuel carbazole: magic fuel from the gas pump. In: Spiegel Online . June 30, 2011, accessed December 3, 2015 . 
7. ↑ Katarzyna Morawa Eblagon: Study of Catalytic Sites on Ruthenium For Hydrogenation of N-ethylcarbazole: Implications of Hydrogen Storage via Reversible Catalytic Hydrogenation . In: J. Phys. Chem. C . No. 114 (21) , 2010, pp. 9720-9730 , doi : 10.1021 / jp908640k .
8. ↑ Hydrogen energy: Design and Development of New Carbon-based Sorbent Systems for an Effective Containment of Hydrogen (PDF; 846 kB)
9. ↑ Hydrogen energy: Hydrogen Storage by Reversible Hydrogenation of Liquid-phase Hydrogen Carriers (PDF; 442 kB)
10. ↑ B. Müller, K. Müller, D. Teichmann, W. Arlt, "Energy storage using methane and energy-carrying substances - a thermodynamic comparison", Chemie Ingenieur Technik, 2011, 83, no. 11, pp. 1-13, doi : 10.1002 / cite.201100113
11. ^ Peter Günter, Jean-Pierre Huignard: Photorefractive Materials and Their Applications 2 . Springer, 2006, ISBN 978-0-387-33924-5 ( page 519 in the Google book search).
12. ↑ Defense Threat Informations Group: Warfare agent - first deployments during World War I ( Memento from February 19, 2009 in the Internet Archive ) (PDF; 70 kB), accessed on July 8, 2011
13. ↑ EM Cowell et al., "WAR WOUNDS AND AIR RAID CASUALTIES - CHEMICAL WARFARE AND THE DOCTOR", The British Medical Journal, 1939 Kampfstoff (English)