Green synthesis of glycerol 1,3-bromo- and iodohydrins under solvent-free conditions

Green Chemistry Letters and Reviews

article

Priscila Faustino dos Santos¹  Sara Raposo Benfica da Silva¹  Fernanda Priscila Nascimento Rodrigues da Silva¹  Jeronimo da Silva Costa²  Jane Sayuri Inada²  Vera Lúcia Patrocinio Pereira¹ 

[1] Instituto de Pesquisas de Produtos Naturais, Universidade Federal do Rio de Janeiro (UFRJ);Instituto Federal de Educação

关键词: Solventless reaction;    KI/Al 2 O 3;    Finkelstein reaction;    green chemistry;    nucleophilic substitution reaction;   

DOI  :  10.1080/17518253.2019.1679265

学科分类：化学（综合）

来源: Taylor & Francis

【 摘 要 】

New eco-friendly conditions for Finkelstein reaction employing homogeneous media or alumina-supported reagents, both solventless, were utilized in the bromohydrins and iodohydrins synthesis from 1,3-dichlorohydrin (1,3-DCH), obtained from glycerol. Thus, the trans -halogenation of glycerol-1,3-dichlorohydrin ( 1 ) in homogeneous media, using NaI, NaBr salts and organic additives (TBAI, TBAB), led to the synthesis of four different glycerol halohydrins ( 2a , 2b , 3a , 3b ) in regular to excellent conversions (43–96%) and good selectivities to 3a and 2b . Already, the alumina-supported reagents such as KI, KBr, NaBr were used for glycerol-1,3-dichlorohydrin trans -halogenation, in the absence of solvent, producing halohydrin mixtures in high conversions (77–99%) and very good selectivity (82%) to 1,3-diiodo-2-propanol ( 2b ).

【 授权许可】

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