Synthesis of fragrance compounds from acyclic monoterpenes : rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and B-citronellene.
dc.contributor.author | Vieira, Camila Grossi | |
dc.contributor.author | Santos, Eduardo Nicolau dos | |
dc.contributor.author | Gusevskaya, Elena Vitalievna | |
dc.date.accessioned | 2015-09-22T19:06:38Z | |
dc.date.available | 2015-09-22T19:06:38Z | |
dc.date.issued | 2013 | |
dc.description.abstract | Rhodium-catalyzed hydroformylation of acyclic monoterpenic compounds, i.e., linalool and _- citronellene, was studied in toluene and ethanol solutions in the presence of PPh3 or P(O-o-tBuPh)3 ligands. Although both substrates have a monosubstituted terminal double bond, they show different behavior under the hydroformylation conditions. In toluene, linalool gave almost quantitatively a cyclic hemiacetal; whereas the hydroformylation of _-citronellene resulted in two isomeric aldehydes also in a nearly quantitative combined yield. The reactions occurred approximately two times faster in ethanol than in toluene giving the corresponding acetals even in the absence of additional acid co-catalysts. In the absence of phosphorous ligands, linalool (differently from _-citronellene) was very resistant to hydroformylation probably due to the binding with rhodium through both the double bond and the hydroxyl group to form stable chelates. The P(O-o-tBuPh)3 ligand exerted a remarkable effect on the reactivity of both substrates accelerating the reactions by 5–20 times as compared to the system with PPh3. Several fragrance compounds were obtained in high yields through a simple one-pot procedure starting from the substrates easily available from natural bio-renewable resources. | pt_BR |
dc.identifier.citation | VIEIRA, C. G.; SANTOS, E. N. dos; GOUSSEVSKAIA, E. V. Synthesis of fragrance compounds from acyclic monoterpenes: rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and B-citronellene. Applied Catalysis. A, General, v. 466, p. 208-215, 2013. Disponível em: <http://www.sciencedirect.com/science/article/pii/S0926860X13003785>. Acesso em: 22 mai. 2015. | pt_BR |
dc.identifier.doi | https://doi.org/10.1016/j.apcata.2013.06.037 | |
dc.identifier.issn | 0926-860X | |
dc.identifier.uri | http://www.repositorio.ufop.br/handle/123456789/5610 | |
dc.language.iso | en_US | pt_BR |
dc.rights.license | O periódico Applied Catalysis A: General concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 3637061429444. | pt_BR |
dc.subject | Acetalization | pt_BR |
dc.subject | Citronellene | pt_BR |
dc.subject | Hydroformylation | pt_BR |
dc.subject | Linalool | pt_BR |
dc.subject | Monoterpenes | pt_BR |
dc.title | Synthesis of fragrance compounds from acyclic monoterpenes : rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and B-citronellene. | pt_BR |
dc.type | Artigo publicado em periodico | pt_BR |
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