Metathesis of renewable raw materials—influence of ligands in the indenylidene type catalysts on self-metathesis of methyl oleate and cross-metathesis of methyl oleate with (Z)-2-butene-1,4-diol diacetate

Kajetanowicz, Anna; Sytniczuk, Adrian; Grela, Karol

doi:10.1039/c3gc42194e

Cited by 31 publications

(35 citation statements)

References 39 publications

(44 reference statements)

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“…Addition of 1,4-benzoquinones cannoto nly help prevent C-C double bond migration (isomerization) [53] but also, as we provedi no ur previous studies, it can lead in some www.chemsuschem.org cases to higherc onversions of as ubstrate. [11] In the next experiment (entry 4) the addition of TFQ was tested and an increaseofthe RCM selectivity was observed. Then, temperature influence on the reaction yield was investigated to find that 50 8Ci st he optimal value.…”

Section: Resultsmentioning

confidence: 97%

“…[1][2][3] The most important in this respect are edible and nonedible oils obtained from variousc ultivars and from algae. [9][10][11] All of these transformationsl ead to valuablep roducts or co-products and have found applications in the industry.O ne of the successful examples is the Arkema process of converting castor oil into valuable speciality polyamide Rilsamid PA12. [9][10][11] All of these transformationsl ead to valuablep roducts or co-products and have found applications in the industry.O ne of the successful examples is the Arkema process of converting castor oil into valuable speciality polyamide Rilsamid PA12.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

et al. 2018

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Macrocyclic musk belongs to a well-known and valued class of the fragrance family. Originally, natural musks were obtained from rectal musk glands which often led to the death of the animals. Recently, a lot of effort was invested to obtain such macrocycles in a synthetic way. This research presents a study on the preparation of macrocyclic lactones with the musk scent by ring-closing metathesis (RCM) using biomass-derived starting materials: oleic and 9-decenoic acid. An experimental rule correlating the C-C double bond substitution pattern in the starting diene and the yield for the RCM macrocyclization was proposed.

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Section: Resultsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

et al. 2018

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“…Utilization of renewable resources by the use of olefin metathesis reactions is a research topic of many groups including ours …”

Section: Resultsmentioning

confidence: 99%

In a Quest for Selectivity Paired with Activity: A Ruthenium Olefin Metathesis Catalyst Bearing an Unsymmetrical Phenanthrene‐Based N‐Heterocyclic Carbene

Dąbrowski

Wyrebek

Trzybiński

et al. 2020

Chemistry A European J

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Robust, selective, and stable in the presence of ethylene, ruthenium olefin metathesis pre‐catalyst, {[3‐benzyl‐1‐(10‐phenyl‐9‐phenanthryl)]‐2‐imidazolidinylidene}dichloro(o‐isopropoxyphenylmethylene)ruthenium(II), Ru‐3, bearing an unsymetrical N‐heterocyclic carbene (uNHC) ligand, has been synthesized. The initiation rate of Ru‐3 was examined by ring‐closing metathesis and cross‐metathesis reactions with a broad spectrum of olefins, showing an unprecendented selectivity. It was also tested in industrially relevant ethenolysis reactions of olefinic substrates from renewable feedstock with very good yields and selectivities.

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“…These fatty α‐hydroxyketones were prepared from the corresponding diols, either by oxidation using a homogeneous palladium‐neocuproine complex or by dehydrogenation using a heterogeneous ruthenium catalyst . Symmetrical α‐hydroxyketones 4 and 5 , derived from self‐metathesis products of methyl oleate, gave nonanal 2 and methyl azelaaldehydate 3 with 88 and 80 % isolated yields, respectively (Table , entries 1–2). This protocol was also applied to other fatty acid derivatives.…”

Section: Resultsmentioning

confidence: 99%

Robust Organocatalysts for the Cleavage of Vegetable Oil Derivatives to Aldehydes through Retrobenzoin Condensation

Bah

Deruer

et al. 2018

Chemistry A European J

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A series of thiazolium salts was prepared and tested for the cleavage of the α-hydroxyketone derived from methyl oleate. The robustness of these precatalysts was determined by dynamic thermogravimetric analyses (TGA). It has been shown that the stability of these species is mainly governed by the nature of the counter-anion and some of them were found to be stable until 350-400 °C. The α-hydroxyketone derived from methyl oleate was cleaved under reactive distillation conditions using optimized, thermally robust N-butylthiazolium triflate to give the cleavage product, namely, nonanal and methyl azelaaldehydate, with 85 and 70 % yields. A range of α-hydroxyketones derived from several fatty acids was cleaved to give the corresponding bio-based aldehydes with up to 98 % isolated yields. Finally, this protocol was successfully applied to a high-oleic sunflower oil derivative.

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Metathesis of renewable raw materials—influence of ligands in the indenylidene type catalysts on self-metathesis of methyl oleate and cross-metathesis of methyl oleate with (Z)-2-butene-1,4-diol diacetate

Cited by 31 publications

References 39 publications

Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

Preparation of Musk‐Smelling Macrocyclic Lactones from Biomass: Looking for the Optimal Substrate Combination

In a Quest for Selectivity Paired with Activity: A Ruthenium Olefin Metathesis Catalyst Bearing an Unsymmetrical Phenanthrene‐Based N‐Heterocyclic Carbene

Robust Organocatalysts for the Cleavage of Vegetable Oil Derivatives to Aldehydes through Retrobenzoin Condensation

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