Lipase-Catalyzed Kinetic Resolution of (+/-)-Mandelonitrile under Conventional Condition and Microwave Irradiation
| Contribuinte(s) |
UNIVERSIDADE DE SÃO PAULO |
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| Data(s) |
23/10/2013
23/10/2013
2012
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| Resumo |
The kinetic resolution of (+/-)-mandelonitrile was carried out using lipase from Candida antarctica under conventional condition (orbital shaker) and microwave irradiation in toluene, producing the (S)-mandelonitrile acetate with high selectivity (up to >98% ee, enantiomeric excess). The unreacted (R)-mandelonitrile under microwave irradiation and conventional condition was partially converted into benzaldehyde by spontaneous chemical equilibrium. The (S)-mandelonitrile acetate under microwave irradiation was produced with 92% ee and 35% yield for 8 h of reaction. Conventional transesterification of (+/-)-mandelonitrile in an orbital shaker produced unreacted (R) -mandelonitrile (51% ee) and (S)-mandelonitrile acetate (98% ee) in accordance with Kazlauskas rule for 184 h of reaction. Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq) Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) FAPESP FAPESP |
| Identificador |
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, SAO PAULO, v. 23, n. 7, supl. 1, Part 1-2, pp. 1395-+, JUL, 2012 0103-5053 http://www.producao.usp.br/handle/BDPI/35597 10.1590/S0103-50532012000700025 |
| Idioma(s) |
eng |
| Publicador |
SOC BRASILEIRA QUIMICA SAO PAULO |
| Relação |
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY |
| Direitos |
closedAccess Copyright SOC BRASILEIRA QUIMICA |
| Palavras-Chave | #KINETIC RESOLUTION #CANDIDA ANTARCTICA LIPASE #MANDELONITRILE #MICROWAVE IRRADIATION #ORBITAL SHAKER #ENANTIOSELECTIVE FORMATION #MANDELONITRILE ACETATE #CANDIDA-ANTARCTICA #THERMAL-STABILITY #CYANOHYDRINS #CHEMISTRY, MULTIDISCIPLINARY |
| Tipo |
article original article publishedVersion |
