Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins
Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterificati...
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Published in | RSC advances Vol. 11; no. 24; pp. 14453 - 14458 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
England
Royal Society of Chemistry
16.04.2021
The Royal Society of Chemistry |
Subjects | |
Online Access | Get full text |
ISSN | 2046-2069 2046-2069 |
DOI | 10.1039/d1ra01980e |
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Abstract | Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields.
Glycerol, a by-product of biodiesel production, can be efficiently converted into α-monobromohydrin or α,γ-dibromohydrin with trimethylsilyl bromide (TMSBr), in solvent-free and mild reaction conditions. |
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AbstractList | Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields. Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields. Glycerol, a by-product of biodiesel production, can be efficiently converted into α-monobromohydrin or α,γ-dibromohydrin with trimethylsilyl bromide (TMSBr), in solvent-free and mild reaction conditions. Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields.Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields. |
Author | Salvini, Antonella Giomi, Donatella Ceccarelli, Jacopo Brandi, Alberto |
AuthorAffiliation | Università degli Studi di Firenze Laboratorio congiunto VALORE, "Valorizzazione di masse algali e sottoprodotti agro-industriali e riduzione di gas serra in atmosfera" Dipartimento di Chimica 'Ugo Schiff' |
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Cites_doi | 10.15227/orgsyn.016.0030 10.1071/CH9942123 10.1055/s-1987-27988 10.1021/jo00087a048 10.1186/1754-6834-5-13 10.1039/C5RA12756D 10.3390/molecules25010221 10.1039/c1gc15053g 10.1039/C9CC09643D 10.2174/1876973X01003010017 10.1590/S0103-50531998000300002 10.1007/BF02540998 10.1016/j.biortech.2003.08.014 10.1016/S0960-8524(99)00025-5 10.1039/C4RA08240K 10.1055/s-0034-1379226 10.1021/jo00113a055 10.3389/fchem.2020.00069 10.1016/j.tetlet.2016.04.083 10.15227/orgsyn.014.0042 10.1039/c2ra20558k 10.1186/2043-7129-2-1 10.1166/jnn.2017.14768 10.1021/ie403268b 10.1039/C4RA00758A 10.1055/s-1983-30320 10.1080/17518253.2019.1679265 10.1021/ja00905a001 10.1021/jo00250a048 |
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SubjectTerms | biodiesel Biodiesel fuels byproducts Castor oil Chemistry Conversion Fine chemicals Glycerol NMR Nuclear magnetic resonance Reagents Transesterification |
Title | Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins |
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