Hydrogenolysis

Hydrogenolysis is the cleavage of a single bond in an organic chemical compound between a carbon atom and a heteroatom or between two carbon atoms with hydrogen under catalysis according to the scheme

${\displaystyle \mathrm {R{-}X\ +\ H_{2}\longrightarrow R{-}H\ +\ H{-}X} }$ or.

${\displaystyle \mathrm {R^{1}{-}R^{2}\ +\ H_{2}\longrightarrow R^{1}{-}H\ +\ R^{2}{-}H} }$

history

The term hydrogenolysis was coined by Carleton Ellis in relation to the hydrogenolysis of carbon-carbon bonds. Paul Sabatier had previously observed the hydrogenolysis of benzyl alcohol to toluene and as early as 1906 Padoa and Ponti had observed the hydrogenolysis of furfuryl alcohol . Homer Burton Adkins and Ralph Connor were the first to call carbon-oxygen bond cleavage hydrogenolysis .

application

Such hydrogenolysis play a role in the desulfurization of petroleum - fractions , the reductive removal of halogens in haloalkanes and the spin-off of certain amino - protecting groups in the peptide synthesis . Frequently, catalysts are used to increase the reaction rate. These are often sub-group elements, especially the platinum metals such as palladium and platinum , but also nickel in the form of Raney nickel , dinickel boride or copper chromite .

Individual evidence

1. ↑ Ralph Connor, Homer Adkins: Hydrogenolysis of Oxygenated Organic Compounds , J. Am. Chem. Soc., 1932, 54 (12), 4678-4690, doi : 10.1021 / ja01351a026 .
2. ^ Siegfried Hauptmann : Organic Chemistry , VEB Deutscher Verlag für Grundstoffindustrie, Leipzig, 2nd edition, 1988, p. 204, ISBN 3-342-00280-8 .
3. ^ K. Peter C. Vollhardt: Organische Chemie , VCH Verlagsgesellschaft, 1990, pp. 1285-1286, ISBN 3-527-26912-6 .