Efficient Telomerization of Butadiene with Starch in Water: The Role of the Surfactant

Mesnager, Julien; Lambin, Anne; Quettier, Claude; Rataboul, Franck; Pinel, Catherine

doi:10.1007/s11244-010-9583-8

Cited by 6 publications

(3 citation statements)

References 8 publications

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“…dimethylacetamide . Other attempts to bridge the polarity gap between 1,3‐butadiene and the polar carbohydrates involve surfactants for the etherification of starch or the use of (aqueous) biphasic reaction mixtures for isosorbide using the trisulfonated triphenylphosphine derivative TPPTS ( L3 ) . Starch occupies a special position in this list because it is a solid under reaction conditions, but naturally present in the aqueous phase, which inhibits the reaction with 1,3‐butadiene.…”

Section: Nucleophilesmentioning

confidence: 99%

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

2019

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Telomerization is a versatile tool for synthesizing unsaturated ethers, amines and other molecules starting from 1,3‐dienes and respective nucleophiles. The homogeneously catalyzed reaction has been the subject of academic and industrial research for over 50 years, offering a broad variety of substrates, catalysts and process concepts. This Minireview presents the advances and developments in this field over the last decade. The focus was on the conversion of renewable resources, the synthesis of promising new products and the development of efficient process concepts to combine these.

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Section: Nucleophilesmentioning

confidence: 99%

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

2019

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“…It was also used with N-methyl glucamine and the renewable polyene -myrcene [181] (see section on N-containing compounds). This reaction has attracted significant interest due to its wide scope, efficiency and ability to undergo in clean and safe conditions [182][183][184][185][186]. Carbohydrate ethers can also be prepared by reductive cleavage of acetals ( Figure 22).…”

Section: Glycosidesmentioning

confidence: 99%

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

Wang¹,

Queneau²

2018

Encyclopedia of Sustainability Science and Technology

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GLOSSARY Carbohydrates are a family of biomolecules, ubiquitous in Nature, based on a common polyhydoxylated backbone though varying in size (from small molecules to macromolecules), in fine structure (configuration and functionalization), and possessing a wide range of biological properties and roles making them indispensable to life. Amphiphiles are molecular architectures with parts exhibiting different types of polarity, generally including hydrophilic and hydrophobic groups. Surfactants are molecules possessing the ability to modulate interfacial tension, notably water surface tension. Bio-based chemicals are chemical products which are obtained by transformation of a starting material arising from biomass, such as carbohydrates, fats, proteins, terpenes. DEFINITION OF THE SUBJECT Surfactants are commodity chemicals used in an incredibly wide range of situations of the everyday life, and must therefore be improved constantly in terms of environmental impact, sustainability and performance. One way towards more sustainable surfactants is the use of renewable resources as raw materials for their manufacture, in place of fossil ones. Since the structure of surfactant combines a polar part to a hydrophobic one, carbohydrates, which are very polar molecules, appear as ideal candidates for serving as renewable building blocks in the synthesis of bio-based surfactants. Developed first with the aim of providing added-value to some agricultural crops and by products, this strategy shows nowadays a rebirth in the context of green and sustainable chemistry. The chapter illustrates, from the chemical point of view, the diversity of molecular structures which belong to the family of carbohydrate-based surfactants.

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“…After optimization of the reaction parameters, high butadiene conversions (up to 93%) could be obtained, while maintaining the granular structure of starch. Secondly, the addition of a strong neutral or cationic surfactant, such as IGEPAL ® CO-890 or cetyltrimethylammonium bromide (CTAB), greatly enhanced reactivity at low 1,3-butadiene concentrations and negated the need of isopropanol as co-solvent (Table 6) [110,111]. The authors explain this effect by the formation of 1,3-butadiene-filled micelles, which are closely associated with the palladium catalyst, de facto creating a local high concentration of 1,3-butadiene.…”

Section: Telomerization With Starchmentioning

confidence: 99%

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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Efficient Telomerization of Butadiene with Starch in Water: The Role of the Surfactant

Cited by 6 publications

References 8 publications

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

The Telomerization of 1,3‐Dienes – A Reaction Grows Up

Carbohydrate-Based Amphiphiles: Resource for Bio-based Surfactants

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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