Titre :

Trialkylamine-Catalyzed Aldolization of Unprotected 1,3-Dihydroxyacetone (DHA) toward C–C Bond-Linked Tetraol Surfactants

Auteur(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]

Titre de la revue :

ACS Sustainable Chemistry & Engineering

Numéro :

6

Pagination :

2630-2640

Éditeur :

ACS

Date de publication :

2018-01-23

Mot(s)-clé(s) en anglais :

Aldolization
Surfactants
Tetraols
Trialkylamines
1,3-Dihydroxyacetone

Discipline(s) HAL :

Chimie/Chimie organique

Résumé en anglais : [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 ...
Lire la suite >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.Lire moins >

Langue :

Anglais

Comité de lecture :

Oui

Audience :

Internationale

Vulgarisation :

Non

Établissement(s) :

ENSCL
CNRS
Centrale Lille
Univ. Artois
Université de Lille

Collections :

• Unité de Catalyse et Chimie du Solide (UCCS) - UMR 8181

Équipe(s) de recherche :

Colloïdes catalyse oxydation (CÏSCO)

Date de dépôt :

2019-09-25T14:37:46Z
2021-03-12T13:55:08Z
2023-11-09T08:28:35Z