Article: Selective palladium nanoparticles-catalyzed hydrogenolysis of industrially targeted epoxides in water
Journal of catalysis. 2021 Apr., v. 396
2021
Abstract: Palladium nanoparticles, with core sizes of ca. 2.5 nm, were easily synthesized by chemical reduction of Na₂PdCl₄ in the presence of hydroxyethylammonium salts and proved to be efficient for the selective hydrogenolysis of various aromatic, alkylphenyl, ... ...
| Abstract | Palladium nanoparticles, with core sizes of ca. 2.5 nm, were easily synthesized by chemical reduction of Na₂PdCl₄ in the presence of hydroxyethylammonium salts and proved to be efficient for the selective hydrogenolysis of various aromatic, alkylphenyl, aliphatic epoxides in water as green solvent. Capping agents of the metal species were screened to define the most suitable micellar nanoreactors on two target substrates of industrial interest, epoxystyrene and 7,8-epoxy-2-methoxy-2,6-dimethyloctane. In our conditions, the hydrogenolysis of epoxystyrene proved to be pH-dependent, producing either the diol under acidic conditions, or the sweet-smelling 2-phenylethanol in the presence of a base. Promisingly, 7,8-epoxy-2-methoxy-2,6-dimethyloctane was completely and selectively hydrogenated into Florsantol®, a sandalwood odorant at a multigram scale (40 g and up to 175g). A general mechanism for the palladium nanoparticles-catalyzed hydrogenolysis of terminal epoxides was proposed according to steric and electronic properties and finely corroborated with deuterium labelling experiments. |
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| Keywords | catalytic activity ; chemical reduction ; deuterium ; epoxides ; odor compounds ; pH ; palladium ; phenylethyl alcohol ; solvents |
| Language | English |
| Dates of publication | 2021-04 |
| Size | p. 261-268. |
| Publishing place | Elsevier Inc. |
| Document type | Article |
| ZDB-ID | 1468993-5 |
| ISSN | 1090-2694 ; 0021-9517 |
| ISSN (online) | 1090-2694 |
| ISSN | 0021-9517 |
| DOI | 10.1016/j.jcat.2021.02.027 |
| Database | NAL-Catalogue (AGRICOLA) |
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