Zweiphasenkatalyse: eine Strategie zur Vermeidung von Konsekutivreaktionen am Beispiel der Telomerisation von Butadien und Ammoniak

Prinz, Thomas; Keim, Wilhelm; Drießen‐Hölscher, Birgit

doi:10.1002/ange.19961081533

Cited by 33 publications

(6 citation statements)

References 10 publications

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“…The reaction of butadiene with ammonia [Eq. (8)] was studied by Drießen-Hölscher et al [106][107][108][109] To avoid consecutive reactions to the secondary and tertiary amines a biphasic method was chosen, which involves a palladium/TPPTS catalyst, which is retained in the aqueous phase. As shown in Table 9 the selectivity towards the primary and secondary amines could be significantly increased by this approach.…”

Section: Telomerization Of Butadiene With Aminesmentioning

confidence: 99%

Telomerization: Advances and Applications of a Versatile Reaction

et al. 2009

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The transition-metal catalyzed telomerization of 1,3-dienes with different nucleophiles leads to the synthesis of numerous products, such as sugar ethers, substituted lactones, or terpene derivatives, which can be applied in the cosmetic and pharmaceutical industry as well as in polymers and flavors. The reaction can be controlled by the choice of the catalytic system, the feedstock, and the reaction conditions. Since telomerization was developed in 1967, there have been many efforts to utilize this reaction. Herein we give an overview of the versatility of telomerization based on examples from research and industry, particular emphasis is placed on catalyst and process development as well as mechanistic aspects.

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Section: Telomerization Of Butadiene With Aminesmentioning

confidence: 99%

Telomerization: Advances and Applications of a Versatile Reaction

et al. 2009

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“…These aspects will now be discussed. However, as stated before, several catalytic investigations concerning the telomerization of 1,3‐butadiene with methanol4–7 or ammonia2, 3 exist and report mass transport limitation at lower stirring rates. To avoid any mass transport limitations a stirring rate of 1200 rpm was chosen in all the experiments discussed.…”

Section: Resultsmentioning

confidence: 88%

Palladium‐Based Telomerization of 1,3‐Butadiene with Glycerol Using Methoxy‐Functionalized Triphenylphosphine Ligands

Palkovits

Nieddu

Kruithof

et al. 2008

Chemistry A European J

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Glycerol is considered a potential renewable building block for the synthesis of existing as well as new chemicals. A promising route is the telomerization of 1,3-butadiene with glycerol leading to C8 chain ethers of glycerol with applications in, for example, surfactant chemistry. Recently, we reported a new set of palladium-based homogeneous catalytic systems for the telomerization of 1,3-butadiene with glycerol and found that palladium complexes bearing methoxy-functionalized triphenylphosphine ligands are highly active catalysts capable of converting crude glycerol without any significant loss of activity. Herein, we present a detailed account of these investigations by reporting on the influence of the butadiene/glycerol ratio, temperature, and reaction time on product selectivity and activity allowing further optimization of catalyst performance. Maximum activity and yield were reached for high 1,3-butadiene/glycerol ratios at a temperature of 90 degrees C, whereas the selectivity for mono- and diethers of glycerol could be optimized by combining high reaction temperatures and short reaction times with low butadiene/glycerol ratios. Variation of the PdII metal precursors and the metal/ligand ratio showed that palladium precursors with halogen ligands gave unsatisfying results, in contrast to precursors with weakly coordinated ligands such as [Pd(OAc)2] and [Pd(acac)2]. [Pd(dba)2], the only Pd0 precursor tested, gave the best results in terms of activity, which illustrates the importance of the ability to form a Pd0 species in the catalytic cycle. Finally, base addition resulted in a shortening of the reaction time and most likely facilitates the formation of a Pd0 species. Based on these results, we were able to realize the first attempts towards a rational ligand design aimed at a high selectivity for mono- and diether formation.

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confidence: 99%

“…[1] Since then, numerous studies have appeared concentrated on monofunctional alcohols and other simple nucleophiles such as ammonia. [2][3][4][5] So far, the only industrial application is the telomerization of butadiene with water leading to 2,7-octadien-1-ol. [6][7][8] Surprisingly, not much work has been done on multifunctional nucleophiles, [9] besides a few studies concerning the telomerization of sugar components or starch.…”

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confidence: 99%

Highly Active Catalysts for the Telomerization of Crude Glycerol with 1,3‐Butadiene

et al. 2008

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The chain gang: Crude glycerol, a by‐product in the production of biodiesel, can be telomerized with 1,3‐butadiene to form C8‐chain ethers. The development of suitable catalyst systems for the direct telomerization of crude glycerol at the biodiesel plant provides a route to useful building blocks from cheap starting materials for commercially valuable products such as detergents and surfactants.

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Zweiphasenkatalyse: eine Strategie zur Vermeidung von Konsekutivreaktionen am Beispiel der Telomerisation von Butadien und Ammoniak

Abstract: ZUSCHRIFTEN[lo] Fur I und 4 1st r = 0.07 bzw. 0.03, mit 0 oder 1, entsprechend einer idealen quadratisch-pyramidalen bzw. trigonal-bipyramidalen Geometrie: A. W. Addison. T. N. Rao, J. Reedijk, J. van Rijn, G. C. Verschoor, J. Chem. Soc. Dalron Trans. 1984, 1349-1356

Cited by 33 publications

References 10 publications

Telomerization: Advances and Applications of a Versatile Reaction

Telomerization: Advances and Applications of a Versatile Reaction

Palladium‐Based Telomerization of 1,3‐Butadiene with Glycerol Using Methoxy‐Functionalized Triphenylphosphine Ligands

Highly Active Catalysts for the Telomerization of Crude Glycerol with 1,3‐Butadiene

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