Process development for the synthesis of saturated branched fatty derivatives: Combination of homogeneous and heterogeneous catalysis in miniplant scale

Haßelberg, Jennifer; Behr, Arno; Weiser, C.; Bially, J.B.; Sinev, Ilya

doi:10.1016/j.ces.2015.12.007

Cited by 9 publications

(7 citation statements)

References 40 publications

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“…Behr [31][32][33][69][70][71] pp / p peptide synthesis 2002 Chiba [36] p --telomerization 2003 Behr [72][73][74] p --hydroacylation 2004 Jun [75] pp --…”

Section: Càcc Ross-couplings 2000mentioning

confidence: 99%

“…However,n either the TOF nor TON values for the process were calculated. [70] As olventc ombination consisting of PEG 1000 and water was used for the rhodium-catalyzed codimerization of 1,3-butadiene with ethylene to trans-1,4-hexadiene ( Figure 15) by Behr et al in 2005. [71] The catalyst RhCl 3 •3H 2 O( 0.07 mol %) was successfully recycled in ten sequential runs.…”

Section: Codimerization/co-oligomerizationmentioning

confidence: 99%

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Thermomorphic Multiphase Systems: Switchable Solvent Mixtures for the Recovery of Homogeneous Catalysts in Batch and Flow Processes

Bianga

Künnemann

Gaide

et al. 2019

Chemistry A European J

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Over the past 20 years, thermomorphic multiphase systems (TMS) have been used as a versatile and elegant strategy for the recovery and recycling of homogeneous transition‐metal catalysts, in both batch‐scale experiments and continuously operated processes. TMS ensure a homogeneous reaction in a monophasic reaction mixture at reaction temperature and the recovery of the homogeneous transition‐metal catalyst through liquid–liquid separation at a lower separation temperature. This is achieved by using at least two solvents, which have a highly temperature‐sensitive miscibility gap. The suitability of commercially available solvents makes this approach highly interesting from an industrial point of view. For the first time, herein, all studies in the area of TMS are reviewed, with the aim of providing a concise and integral representation of this approach for homogeneous catalyst recovery. In addition to the discussion of examples from the literature, the thermodynamic fundamentals of the temperature‐dependent miscibility of solvents are also presented. This review also gives key indicators to compare different TMS approaches, for instance. In this way, new solvent combinations and in‐depth research, as well as improvements to existing approaches, can be addressed and promoted.

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“…Behr [31][32][33][69][70][71] pp / p peptide synthesis 2002 Chiba [36] p --telomerization 2003 Behr [72][73][74] p --hydroacylation 2004 Jun [75] pp --…”

Section: Càcc Ross-couplings 2000mentioning

confidence: 99%

Section: Codimerization/co-oligomerizationmentioning

confidence: 99%

Thermomorphic Multiphase Systems: Switchable Solvent Mixtures for the Recovery of Homogeneous Catalysts in Batch and Flow Processes

Bianga

Künnemann

Gaide

et al. 2019

Chemistry A European J

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“…An interesting process for the production of branched fatty compounds based on renewable resources was recently reported by Behr et al . This new process entails the combination of homogeneously catalyzed co‐oligomerization, initial catalyst recycling using the TMS‐technique, heterogeneously catalyzed hydrogenation in a trickle bed reactor and subsequent catalyst extraction from the saturated branched compounds.…”

Section: Discussionmentioning

confidence: 99%

“…Homogeneous catalyzed co‐oligomerization of fatty acids has been reported by Behr et al . A synthesis route to saturated branched fatty compounds was investigated successfully in miniplant scale .…”

Section: Synthesis Routesmentioning

confidence: 99%

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Saturated branched fatty compounds: Proven industrial processes and new alternatives

Haßelberg

Behr

2015

Euro J Lipid Sci & Tech

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This paper reviews properties and synthesis of saturated branched fatty compounds and their application. Especially industrially established processes based on the Guerbet reaction, Fatty acid isomerization, Oxo‐ and Koch synthesis will be presented. Also new laboratory methods will be discussed, e.g., the Lewis acid‐induced hydroalkylation of oleic acids. Recently, another new process has been developed and tested in miniplant scale, the homogeneously catalyzed co‐oligomerization of linoleic acid with ethylene. This process combines the co‐oligomerization step with the heterogeneously catalyzed hydrogenation and an additional extraction to recycle the catalyst. Practical applications: This review presents synthesis routes of saturated branched fatty compounds based on both, established processes in industry and recent research results on alternative routes. A new developed process on the co‐oligomerization of fatty acids or esters is highlighted as an alternative route to form saturated branched fatty compounds. Reformulation of mineral oil based lubricants for improved biodegradability in, e.g., high‐loss lubrication systems and high‐risk hydraulic systems is highly encouraged by the oleo industry. Therefore, chemical modification of vegetable oils is also interesting for recent research on biolubricants. In addition the paper reviews latest scientific papers and patents on already industrially established processes or synthesis routes, like the fatty acid isomerization, hydroformylation, and the formation of Guerbet alcohols or Neo acids. Covering the respective reactions this review combines interesting synthesis routes for both, oleo‐ and petrochemistry. Saturated branched fatty compounds can be synthesized from both, petro‐ and oleochemical feedstock. Respective industrial processes and new synthesis routes are reviewed. New modification methods of vegetable oils represent interesting alternatives for, e.g., the formation of biolubricants.

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Oleochemistry

Vorholt¹,

Behr²

2017

Applied Homogeneous Catalysis With Organometallic Compounds

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Process development for the synthesis of saturated branched fatty derivatives: Combination of homogeneous and heterogeneous catalysis in miniplant scale

Cited by 9 publications

References 40 publications

Thermomorphic Multiphase Systems: Switchable Solvent Mixtures for the Recovery of Homogeneous Catalysts in Batch and Flow Processes

Thermomorphic Multiphase Systems: Switchable Solvent Mixtures for the Recovery of Homogeneous Catalysts in Batch and Flow Processes

Saturated branched fatty compounds: Proven industrial processes and new alternatives

Oleochemistry

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