Raffination von Pflanzenölen für die Chemie durch Olefinmetathese

Chikkali, Samir H.; Mecking, Stefan

doi:10.1002/ange.201107645

Cited by 38 publications

(10 citation statements)

References 71 publications

(72 reference statements)

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“…Amongt hem, unsaturated long-chain aliphatic carboxylic acids, esters, and triglyceridesare of major interest as they can be derived from abundant feedstocks such as vegetable oils and animal fats. [26] However,n umerous byproducts were formed concomitantly,w hich thus limits the interest of such an approach. The introductiono f at erminal C=Cb ond within these molecules has been envisaged using several approaches.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Decarbonylation of Biosourced Substrates

et al. 2015

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Linear α-olefins (LAO) are one of the main targets in the field of surfactants, lubricants, and polymers. With the depletion of petroleum resources, the production of LAO from renewable feedstocks has gained increasing interest in recent years. In the present study, we demonstrated that Ir catalysts were suitable to decarbonylate a wide range of biosourced substrates under rather mild conditions (160 °C, 5 h reaction time) in the presence of potassium iodide and acetic anhydride. The resulting LAO were obtained with good conversion and selectivity provided that the purity of the substrate, the nature of the ligand, and the amounts of the additives were controlled accurately. The catalytic system could be recovered efficiently by using a Kugelrohr distillation apparatus and recycled.

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Section: Introductionmentioning

confidence: 99%

Catalytic Decarbonylation of Biosourced Substrates

et al. 2015

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“…[8] Nevertheless, the economical viability of industrial processes at multi-tons cale depends not only on the catalyst efficiency and selectivity, [9] but also on the quality of the involved raw materials. [11] Severalm ethodologies to trap catalyst poisoning species present in vegetable oils (e.g.,p eroxides, phosphates, sulfates, soap, etc.) Because the pre-treatment of the oleo-raw materials represents ak ey success factor for ac ost-effectivem etathesisp rocess, many efforts have been made to address this concern.…”

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confidence: 99%

Bleaching Earths as Powerful Additives for Ru‐Catalyzed Self‐Metathesis of Non‐Refined Methyl Oleate at Pilot Scale

Allard

Curbet

Chollet

et al. 2017

Chemistry A European J

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A practical and cost-effective ruthenium-catalyzed self-metathesis of non-refined methyl oleate (85 %) derived from very high oleic sunflower oils was demonstrated at pilot scale using a robust and kg-scale commercially available SIPr-M71 pre-catalyst. The simple addition of 1 wt % bleaching earths (Tonsil 110FF) to a thermally pretreated oil could efficiently prevent catalyst deactivation. Remarkably, without the need for filtration, the catalytic system was able to achieve a turnover number (TON) of more than 744 000 at a catalyst loading of only 1 ppm. At large scale (up to 200 kg), the equilibrium of the self-metathesis reaction was reached within 1 hour at 50 °C under neat conditions at a very low 5 ppm catalyst loading to produce the expected primary metathesis products (PMP), that is, 9-octadecene and dimethyl-9-octadecenoate, with a productive TON of 94900.

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“…[11,12] This species belongs to the group of diatoms, ubiquitously present in aquatic and unicellular microalgae, which are major players in the global carbon cycle with an estimated share of up to 20 % of total global carbon fixation. [16] In contrast to traditional plant oils, [17][18][19] algae do not contain fatty acids primarily in the form of triacylglycerides, but rather as diacylglycerides substituted with polar substituents such as galactosyl or phosphate groups on the third hydroxy moiety of glycerol ( Figure 1). [16] In contrast to traditional plant oils, [17][18][19] algae do not contain fatty acids primarily in the form of triacylglycerides, but rather as diacylglycerides substituted with polar substituents such as galactosyl or phosphate groups on the third hydroxy moiety of glycerol ( Figure 1).…”

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confidence: 99%

Synthetic Polyester from Algae Oil

et al. 2014

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Current efforts to technically use microalgae focus on the generation of fuels with a molecular structure identical to crude oil based products. Here we suggest a different approach for the utilization of algae by translating the unique molecular structures of algae oil fatty acids into higher value chemical intermediates and materials. A crude extract from a microalga, the diatom Phaeodactylum tricornutum, was obtained as a multicomponent mixture containing amongst others unsaturated fatty acid (16:1, 18:1, and 20:5) phosphocholine triglycerides. Exposure of this crude algae oil to CO and methanol with the known catalyst precursor [{1,2-(tBu2 PCH2)2C6H4}Pd(OTf)](OTf) resulted in isomerization/methoxycarbonylation of the unsaturated fatty acids into a mixture of linear 1,17- and 1,19-diesters in high purity (>99 %). Polycondensation with a mixture of the corresponding diols yielded a novel mixed polyester-17/19.17/19 with an advantageously high melting and crystallization temperature.

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Raffination von Pflanzenölen für die Chemie durch Olefinmetathese

Cited by 38 publications

References 71 publications

Catalytic Decarbonylation of Biosourced Substrates

Catalytic Decarbonylation of Biosourced Substrates

Bleaching Earths as Powerful Additives for Ru‐Catalyzed Self‐Metathesis of Non‐Refined Methyl Oleate at Pilot Scale

Synthetic Polyester from Algae Oil

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