Trialkylamine-Catalyzed Aldolization of ...
Document type :
Article dans une revue scientifique
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Title :
Trialkylamine-Catalyzed Aldolization of Unprotected 1,3-Dihydroxyacetone (DHA) toward C–C Bond-Linked Tetraol Surfactants
Author(s) :
Zhu, Biwen [Auteur]
Belmessieri, Dorine [Auteur]
Ontiveros, Jesus [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Aubry, Jean-Marie [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Chen, Guo-Rong [Auteur]
Duguet, Nicolas [Auteur]
Lemaire, Marc [Auteur]
Belmessieri, Dorine [Auteur]
Ontiveros, Jesus [Auteur]

Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Aubry, Jean-Marie [Auteur]

Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Chen, Guo-Rong [Auteur]
Duguet, Nicolas [Auteur]
Lemaire, Marc [Auteur]
Journal title :
ACS Sustainable Chemistry & Engineering
Volume number :
6
Pages :
2630-2640
Publisher :
ACS
Publication date :
2018-01-23
English keyword(s) :
Aldolization
Surfactants
Tetraols
Trialkylamines
1,3-Dihydroxyacetone
Surfactants
Tetraols
Trialkylamines
1,3-Dihydroxyacetone
HAL domain(s) :
Chimie/Chimie organique
English abstract : [en]
The aldolization of unprotected 1,3-dihydroxyacetone (DHA) was studied under mild conditions (20 °C) in a mixture of water/EtOH using hydrocinnamaldehyde as a model substrate. It was shown that trimethylamine is the most ...
Show more >The aldolization of unprotected 1,3-dihydroxyacetone (DHA) was studied under mild conditions (20 °C) in a mixture of water/EtOH using hydrocinnamaldehyde as a model substrate. It was shown that trimethylamine is the most effective base for this transformation, giving the corresponding aldol with up to 98% selectivity and 82% yield. The method was extended to a range of (biobased) aldehydes to give α-hydroxyketones with 29–70% isolated yields. These α-hydroxyketones were reduced under hydrogen using 5%-Ru/Al2O3 in EtOH at 100 °C to give tetraols with 79–97% isolated yields. The physicochemical properties of these tetraols were studied (CMC, Krafft point, PIT-slope method), and these studies revealed that this new class of C–C bond-linked nonionic surfactants exhibits high effectiveness, reducing the surface tension of water.Show less >
Show more >The aldolization of unprotected 1,3-dihydroxyacetone (DHA) was studied under mild conditions (20 °C) in a mixture of water/EtOH using hydrocinnamaldehyde as a model substrate. It was shown that trimethylamine is the most effective base for this transformation, giving the corresponding aldol with up to 98% selectivity and 82% yield. The method was extended to a range of (biobased) aldehydes to give α-hydroxyketones with 29–70% isolated yields. These α-hydroxyketones were reduced under hydrogen using 5%-Ru/Al2O3 in EtOH at 100 °C to give tetraols with 79–97% isolated yields. The physicochemical properties of these tetraols were studied (CMC, Krafft point, PIT-slope method), and these studies revealed that this new class of C–C bond-linked nonionic surfactants exhibits high effectiveness, reducing the surface tension of water.Show less >
Language :
Anglais
Peer reviewed article :
Oui
Audience :
Internationale
Popular science :
Non
Administrative institution(s) :
ENSCL
CNRS
Centrale Lille
Univ. Artois
Université de Lille
CNRS
Centrale Lille
Univ. Artois
Université de Lille
Collections :
Research team(s) :
Colloïdes catalyse oxydation (CÏSCO)
Submission date :
2019-09-25T14:37:46Z
2021-03-12T13:55:08Z
2023-11-09T08:28:35Z
2021-03-12T13:55:08Z
2023-11-09T08:28:35Z
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