Hydrogen evolution from organic "hydrides"

Daniel E. Schwarz, Thomas M. Cameron, P. Jeffrey Hay, Brian L. Scott, William Tumas, David L. Thorn

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

New concepts of hydrogen storage are being explored for applications from portable power to transportation for the future hydrogen economy. The exergonic evolution of hydrogen gas at room temperature via catalysis from reduced organic compounds was studied. Hydrogen elimination from 2-(1,3-dimethylbenzimidazoline-2-yl)benzoic acid comprised the catalyzed reaction between the "hydride" from the unique C-H of the imidazolidine and a "proton" from the carboxyl group. This reactivity was confirmed by the reaction of 1,3-dimethyl-2-phenylbenzimidazoline (3) with acetic acid or benzoic acid under an inert atmosphere in the presence of finely divided palladium to afford hydrogen and the phenylbenzimidazolium cation. Compound 3 was stable toward these acids for days when no catalyst was present. 1,3-Dimethylbenzimidazoline (5) evolved hydrogen in the presence of acetic or benzoic acid and catalyst, similar to compound 3. Ambient-temperature hydrogen formation from benzimidazolidines and carboxylic acids was strongly favored and using hydrogen pressure alone to drive the reaction backwards would be extremely difficult. Water was sufficiently acidic for Pd-catalyzed hydrogen evolution from compounds 3 and 5. However, in the presence of water, the reactions were far more complex than the reactions involving carboxylic acids due to further reactions of water and hydroxide with the phenylbenzimidazolium and 1,3-dimethylbenzimidazolium cations. This is an abstract of a paper presented in the ACS Fuel Chemistry Meeting Fall 2005 (Washington, DC Fall 2005).

Original languageEnglish
Title of host publicationACS Division of Fuel Chemistry, Preprints
Pages544-545
Number of pages2
Volume50
Edition2
Publication statusPublished - 2005

Fingerprint

Hydrides
Hydrogen
Benzoic acid
Carboxylic acids
Acetic acid
Positive ions
Water
Catalysts
Hydrogen storage
Organic compounds
Palladium
Catalysis
Protons
Temperature
Acids
Gases

ASJC Scopus subject areas

  • Energy(all)

Cite this

Schwarz, D. E., Cameron, T. M., Hay, P. J., Scott, B. L., Tumas, W., & Thorn, D. L. (2005). Hydrogen evolution from organic "hydrides". In ACS Division of Fuel Chemistry, Preprints (2 ed., Vol. 50, pp. 544-545)

Hydrogen evolution from organic "hydrides". / Schwarz, Daniel E.; Cameron, Thomas M.; Hay, P. Jeffrey; Scott, Brian L.; Tumas, William; Thorn, David L.

ACS Division of Fuel Chemistry, Preprints. Vol. 50 2. ed. 2005. p. 544-545.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Schwarz, DE, Cameron, TM, Hay, PJ, Scott, BL, Tumas, W & Thorn, DL 2005, Hydrogen evolution from organic "hydrides". in ACS Division of Fuel Chemistry, Preprints. 2 edn, vol. 50, pp. 544-545.
Schwarz DE, Cameron TM, Hay PJ, Scott BL, Tumas W, Thorn DL. Hydrogen evolution from organic "hydrides". In ACS Division of Fuel Chemistry, Preprints. 2 ed. Vol. 50. 2005. p. 544-545
Schwarz, Daniel E. ; Cameron, Thomas M. ; Hay, P. Jeffrey ; Scott, Brian L. ; Tumas, William ; Thorn, David L. / Hydrogen evolution from organic "hydrides". ACS Division of Fuel Chemistry, Preprints. Vol. 50 2. ed. 2005. pp. 544-545
@inproceedings{bb0a49c0cc89439da2d29b7c92e44c44,
title = "Hydrogen evolution from organic {"}hydrides{"}",
abstract = "New concepts of hydrogen storage are being explored for applications from portable power to transportation for the future hydrogen economy. The exergonic evolution of hydrogen gas at room temperature via catalysis from reduced organic compounds was studied. Hydrogen elimination from 2-(1,3-dimethylbenzimidazoline-2-yl)benzoic acid comprised the catalyzed reaction between the {"}hydride{"} from the unique C-H of the imidazolidine and a {"}proton{"} from the carboxyl group. This reactivity was confirmed by the reaction of 1,3-dimethyl-2-phenylbenzimidazoline (3) with acetic acid or benzoic acid under an inert atmosphere in the presence of finely divided palladium to afford hydrogen and the phenylbenzimidazolium cation. Compound 3 was stable toward these acids for days when no catalyst was present. 1,3-Dimethylbenzimidazoline (5) evolved hydrogen in the presence of acetic or benzoic acid and catalyst, similar to compound 3. Ambient-temperature hydrogen formation from benzimidazolidines and carboxylic acids was strongly favored and using hydrogen pressure alone to drive the reaction backwards would be extremely difficult. Water was sufficiently acidic for Pd-catalyzed hydrogen evolution from compounds 3 and 5. However, in the presence of water, the reactions were far more complex than the reactions involving carboxylic acids due to further reactions of water and hydroxide with the phenylbenzimidazolium and 1,3-dimethylbenzimidazolium cations. This is an abstract of a paper presented in the ACS Fuel Chemistry Meeting Fall 2005 (Washington, DC Fall 2005).",
author = "Schwarz, {Daniel E.} and Cameron, {Thomas M.} and Hay, {P. Jeffrey} and Scott, {Brian L.} and William Tumas and Thorn, {David L.}",
year = "2005",
language = "English",
volume = "50",
pages = "544--545",
booktitle = "ACS Division of Fuel Chemistry, Preprints",
edition = "2",

}

TY - GEN

T1 - Hydrogen evolution from organic "hydrides"

AU - Schwarz, Daniel E.

AU - Cameron, Thomas M.

AU - Hay, P. Jeffrey

AU - Scott, Brian L.

AU - Tumas, William

AU - Thorn, David L.

PY - 2005

Y1 - 2005

N2 - New concepts of hydrogen storage are being explored for applications from portable power to transportation for the future hydrogen economy. The exergonic evolution of hydrogen gas at room temperature via catalysis from reduced organic compounds was studied. Hydrogen elimination from 2-(1,3-dimethylbenzimidazoline-2-yl)benzoic acid comprised the catalyzed reaction between the "hydride" from the unique C-H of the imidazolidine and a "proton" from the carboxyl group. This reactivity was confirmed by the reaction of 1,3-dimethyl-2-phenylbenzimidazoline (3) with acetic acid or benzoic acid under an inert atmosphere in the presence of finely divided palladium to afford hydrogen and the phenylbenzimidazolium cation. Compound 3 was stable toward these acids for days when no catalyst was present. 1,3-Dimethylbenzimidazoline (5) evolved hydrogen in the presence of acetic or benzoic acid and catalyst, similar to compound 3. Ambient-temperature hydrogen formation from benzimidazolidines and carboxylic acids was strongly favored and using hydrogen pressure alone to drive the reaction backwards would be extremely difficult. Water was sufficiently acidic for Pd-catalyzed hydrogen evolution from compounds 3 and 5. However, in the presence of water, the reactions were far more complex than the reactions involving carboxylic acids due to further reactions of water and hydroxide with the phenylbenzimidazolium and 1,3-dimethylbenzimidazolium cations. This is an abstract of a paper presented in the ACS Fuel Chemistry Meeting Fall 2005 (Washington, DC Fall 2005).

AB - New concepts of hydrogen storage are being explored for applications from portable power to transportation for the future hydrogen economy. The exergonic evolution of hydrogen gas at room temperature via catalysis from reduced organic compounds was studied. Hydrogen elimination from 2-(1,3-dimethylbenzimidazoline-2-yl)benzoic acid comprised the catalyzed reaction between the "hydride" from the unique C-H of the imidazolidine and a "proton" from the carboxyl group. This reactivity was confirmed by the reaction of 1,3-dimethyl-2-phenylbenzimidazoline (3) with acetic acid or benzoic acid under an inert atmosphere in the presence of finely divided palladium to afford hydrogen and the phenylbenzimidazolium cation. Compound 3 was stable toward these acids for days when no catalyst was present. 1,3-Dimethylbenzimidazoline (5) evolved hydrogen in the presence of acetic or benzoic acid and catalyst, similar to compound 3. Ambient-temperature hydrogen formation from benzimidazolidines and carboxylic acids was strongly favored and using hydrogen pressure alone to drive the reaction backwards would be extremely difficult. Water was sufficiently acidic for Pd-catalyzed hydrogen evolution from compounds 3 and 5. However, in the presence of water, the reactions were far more complex than the reactions involving carboxylic acids due to further reactions of water and hydroxide with the phenylbenzimidazolium and 1,3-dimethylbenzimidazolium cations. This is an abstract of a paper presented in the ACS Fuel Chemistry Meeting Fall 2005 (Washington, DC Fall 2005).

UR - http://www.scopus.com/inward/record.url?scp=32244445158&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=32244445158&partnerID=8YFLogxK

M3 - Conference contribution

VL - 50

SP - 544

EP - 545

BT - ACS Division of Fuel Chemistry, Preprints

ER -