Telomerisation of 1,3-butadiene with glycerol under aqueous biphasic conditions: Influence of the reaction conditions on the products distribution

Bigot, Sandra; Lai, Jonathan; Suisse, Isabelle; Sauthier, Mathieu; Mortreux, André; Castanet, Yves

doi:10.1016/j.apcata.2010.04.039

Cited by 22 publications

(21 citation statements)

References 35 publications

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“…The reaction between 1,3-butadiene and glycerol led to various alkenyl glycerol ethers (telomers)-a class of unsaturated ethers with potentials particularly in surfactant chemistry (343,344). Such a reaction is also regarded as telomerization in which glycerol as telogen reacts with unsaturated 1,3-butadiene as taxogen molecule (Fig.…”

Section: Glycerol To Monoalkyl Glyceryl Ethersmentioning

confidence: 98%

Recent Advances in Catalytic Conversion of Glycerol

Zhou¹,

Zhao²,

Tong³

et al. 2013

Catalysis Reviews

177

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The article underlines and discusses the state-of-the-art accomplishments in the catalytic conversion of glycerol (1,2,3-propanetriol) to fuels and value-added chemicals in the past five years (2008)(2009)(2010)(2011)(2012). The reactions include steam reforming, aqueous-phase reforming, hydrogenolysis, oxidation, dehydration, esterification, etherification, carboxylation, acetalization, and chlorination. Typical products are hydrogen, propanediols, dihydroxyacetone, glyceric acid, acrolein, glyceride, polyglycerol, glycerol carbonate, acetals, ketals, and epichlorohydrine. Recent studies on the catalysts, reaction conditions, and possible pathways are primarily discussed. They indicate that major breakthroughs are achieved by the use of multifunctional catalysts, process intensification and integrated reactions. Literature survey suggests that future work on the catalytic conversion of glycerol for commercial goals particularly requires new catalysts, innovative reactor engineering, and close multidisciplinary partnership.

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Section: Glycerol To Monoalkyl Glyceryl Ethersmentioning

confidence: 98%

Recent Advances in Catalytic Conversion of Glycerol

Zhou¹,

Zhao²,

Tong³

et al. 2013

Catalysis Reviews

177

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“…Langmuir ARTICLE 3 J HÀH = 7.4 Hz and 3 J HÀH = 6.6 Hz, CHÀCH 2 ÀCH 2 ÀCH 2 ÀCH); 1.40 (tt, 2H, 3 J HÀH = 7.4 Hz, CH 2 ÀCH 2 ÀCH 2 ). 13 3 J HÀH = 6.9 Hz, CH 2 ÀCH 2 O); 3.24 (m, 1H, OH); 1.49 (tt, 2H, 3 J HÀH = 6.9 Hz, CH 2 ÀCH 2 ÀCH 2 O); 1.19 (m, 10H, CH 3 ÀCH 2 ÀCH 2 ÀCH 2 ÀCH 2 ÀCH 2 ÀCH 2 ÀCH 2 O); 0.79 (t, 3H, 3 J HÀH = 6.9 Hz, CH 3 ÀCH 2 ). 13 3 J HÀH = 6.9 Hz, 1H, OH); 1.49 (tt, 2H, 3 J HÀH = 6.9 Hz, CH 2 ÀCH 2 ÀCH 2 O); 1.18 (m, 10H, CH 3 ÀCH 2 ÀCH 2 ÀCH 2 ÀCH 2 À CH 2 ÀCH 2 ÀCH 2 O); 0.79 (t, 3H, 3 J HÀH = 6.9 Hz, CH 3 ÀCH 2 ).…”

Section: Hydrogenationunclassified

“…13 3 J HÀH = 6.9 Hz, 1H, OH); 1.49 (tt, 2H, 3 J HÀH = 6.9 Hz, CH 2 ÀCH 2 ÀCH 2 O); 1.18 (m, 10H, CH 3 ÀCH 2 ÀCH 2 ÀCH 2 ÀCH 2 À CH 2 ÀCH 2 ÀCH 2 O); 0.79 (t, 3H, 3 J HÀH = 6.9 Hz, CH 3 ÀCH 2 ). 13 …”

Section: Hydrogenationunclassified

Effect of Chain Unsaturation on the Self-Association of Tri- and Tetraethylene Glycol Octyl Ethers Obtained by Butadiene Telomerization

et al. 2011

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2,7-Octadienyl ethers of tri- and tetraethylene glycol (C(8:2)E(3) and C(8:2)E(4)) have been synthesized by the atom-economical butadiene telomerization of the corresponding poly(ethylene glycols). On one hand, this synthetic path is attractive because it is expeditious and environmentally benign, and on the other hand, it provides unconventional amphiphiles for which the lipophilic chains possess two double bonds. These two unsaturations increase the global hydrophilicity of the compound, which is also highlighted by the modelization of the compounds using the conductor-like screening model for real solvents (COSMO-RS). The behavior of C(8:2)E(3) and C(8:2)E(4) in binary amphiphile/water and ternary amphiphile/oil/water systems is therefore greatly modified compared to that of the conventional fully saturated homologues (C(8)E(3) and C(8)E(4)) that are easily obtained after hydrogenation. This results in a lowered efficiency of the unsaturated compounds for oil solubilization. The usual Winsor-type microemulsion systems are formed, and for the same oil, the DLS investigation of the microstructure of the Winsor I microemulsion does not highlight any difference in the self-association between the unsaturated and saturated compounds.

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“…9 Influence of water concentration on the concentration profiles of substrate and products in the telomerization of glycerol. Adapted with permission from [88] showed a product distribution similar to the one obtained with pure glycerol. Due to the large amount of water present, octadienol now appeared as a major by-product.…”

Section: Telomerization Of Glycerolmentioning

confidence: 56%

“…Bigot et al also used biphasic aqueous conditions for their telomerization reactions of glycerol, focusing mainly on optimization of various parameters for not only mono-, but also di-and tri-telomer production [88]. Unlike Behr, a positive influence of the base sodium hydroxide on activity was observed under their conditions (24% conversion after 2.5 h without base, 86% conversion in 1 M NaOH), with TOFs of up to 2,000 h À1 .…”

Section: Telomerization Of Glycerolmentioning

confidence: 97%

Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules

Bruijnincx

Jastrzebski

Hausoul

et al. 2012

Organometallics and Renewables

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The dimerization of 1,3-dienes (e.g. butadiene) with the addition of a protic nucleophile (e.g. methanol) yields 2,7-octadienyl ethers in the so-called telomerization reaction. This reaction is most efficiently catalyzed by homogeneous palladium complexes. The field has experienced a renaissance in recent years as many of the platform molecules that can be renewably obtained from biomass are well-suited to act as multifunctional nucleophiles in this reaction. In addition, the process adheres to many of the principles of green chemistry, given that the reaction is 100% atom efficient and produces little waste. The telomerization reaction thus provides a versatile route for the production of valuable bulk and specialty chemicals that are (at least partly) green and renewable. The use of various multifunctional substrates that can be obtained from biomass is covered in this review, as well as mechanistic aspects of the telomerization reaction.

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Telomerisation of 1,3-butadiene with glycerol under aqueous biphasic conditions: Influence of the reaction conditions on the products distribution

Cited by 22 publications

References 35 publications

Recent Advances in Catalytic Conversion of Glycerol

Recent Advances in Catalytic Conversion of Glycerol

Effect of Chain Unsaturation on the Self-Association of Tri- and Tetraethylene Glycol Octyl Ethers Obtained by Butadiene Telomerization

Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules

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