Synthesis of fragrance compounds from acyclic monoterpenes : rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and B-citronellene.

dc.contributor.authorVieira, Camila Grossi
dc.contributor.authorSantos, Eduardo Nicolau dos
dc.contributor.authorGusevskaya, Elena Vitalievna
dc.date.accessioned2015-09-22T19:06:38Z
dc.date.available2015-09-22T19:06:38Z
dc.date.issued2013
dc.description.abstractRhodium-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.citationVIEIRA, 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.doihttps://doi.org/10.1016/j.apcata.2013.06.037
dc.identifier.issn0926-860X
dc.identifier.urihttp://www.repositorio.ufop.br/handle/123456789/5610
dc.language.isoen_USpt_BR
dc.rights.licenseO periódico Applied Catalysis A: General concede permissão para depósito deste artigo no Repositório Institucional da UFOP. Número da licença: 3637061429444.pt_BR
dc.subjectAcetalizationpt_BR
dc.subjectCitronellenept_BR
dc.subjectHydroformylationpt_BR
dc.subjectLinaloolpt_BR
dc.subjectMonoterpenespt_BR
dc.titleSynthesis of fragrance compounds from acyclic monoterpenes : rhodium catalyzed hydroformylation and tandem hydroformylation/acetalization of linalool and B-citronellene.pt_BR
dc.typeArtigo publicado em periodicopt_BR
Arquivos
Pacote Original
Agora exibindo 1 - 1 de 1
Carregando...
Imagem de Miniatura
Nome:
ARTIGO_SynthesisFragranceCompounds.pdf
Tamanho:
452.25 KB
Formato:
Adobe Portable Document Format
Licença do Pacote
Agora exibindo 1 - 1 de 1
Nenhuma Miniatura disponível
Nome:
license.txt
Tamanho:
2.57 KB
Formato:
Item-specific license agreed upon to submission
Descrição: