Zum Einfluß von Schutzgruppen bei der Metathese fettchemischer Verbindungen

Warwel, Siegfried; Döring, N.; Biermanns, F. J.

doi:10.1002/lipi.19870890902

Cited by 3 publications

(3 citation statements)

References 16 publications

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“…6 Other long chain alcohols, such as 10-undecenol that can be derived from castor oil, were also investigated in metathesis reactions. Warwel et al could show that protecting groups have a large influence on the reactivity of these chemicals in cross-metathesis reactions with ethene or 4-octene 7 and that it is possible to use silylated fatty alcohol derivatives to yield chain shortened fatty alcohols upon metathesis with hexenes. 8 In both cases heterogeneous rhenium catalysts were applied.…”

Section: Introductionmentioning

confidence: 99%

Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

Rybak

Meier

2008

Green Chem.

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The synthesis of a,w-difunctional monomers from the renewable resource oleyl alcohol via a cross-metathesis reaction with methyl acrylate is described. The reaction conditions were optimized for high conversions in combination with high cross-metathesis selectivity. The introduction of a protecting group for the alcohol functionality of oleyl alcohol was found to be a necessary step in order to significantly reduce the amount of metathesis catalyst required to obtain full conversions and good selectivities. All reaction conditions were compared to each other in a quantitative fashion with the program EATOS (environmental assessment tool for organic syntheses) revealing the environmentally most benign approach for the synthesis of the desired a,w-difunctional monomers. These calculations also clearly revealed that the introduction of the protecting group was a necessary step in order to minimize the amount of the produced waste and to use the raw materials more efficiently.

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Section: Introductionmentioning

confidence: 99%

Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

Rybak

Meier

2008

Green Chem.

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“…Protected oleyl alcohols are known to produce α , ω ‐diols 11, 12. Acetylated oleyl alcohol subjected to metathesis gives nearly the same yield as oleic acid esters.…”

Section: Resultsmentioning

confidence: 99%

Self Metathesis of Fatty Alcohols and Amines to Provide Monomers for Polyester and Polyamide Products

Riepl¹,

Pettrak²,

Faulstich³

et al. 2010

Macromolecular Symposia

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Self metathesis of oleochemicals offers a variety of bifunctional compounds, that can be used as monomer for polymer production. Many precursors are in huge scales available, like oleic acid ester (biodiesel), oleyl alcohol (tensides), oleyl amines (tensides, lubricants). We show several ways to produce and separate and purify C 18 -a,v-bifunctional compounds, using Grubbs 2 nd Generation catalysts, starting from technical grade educts. Ã using VTA thin film evaporation apparatus VKL 70, 4 dm 2 evaporation surface; Octadec-9-ene is obtained at 100 8C at 0.033 mbar; Oleic acid ethyl ester is obtained at 120 8C at 0.0008 mbar; Octadec-9-ene-1,18-dioic acid diethyl ester is obtained at 130 8C at 0.0008 mbar, yielding a small residing fraction, containing nearly all ruthenium.

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“…Deactivation by complexation of a functional group can be prevented by the introduction of a protecting group, prior to metathesis. For example, Warwel et al (24) obtained rather high conversions in the metathesis of an unsaturated alcohol when the alcohol group was converted into a trimethyl silyl ether, whereas the alcohol itself deactivates the catalyst immediately and does not show any conversion.…”

Section: Reaction Mechanism Of Metathesismentioning

confidence: 99%

Technological and economical aspects of the metathesis of unsaturated esters

Sibeijn¹,

Poels²,

Bliek³

et al. 1994

J Americ Oil Chem Soc

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The metathesis of alkenes is a well‐established reaction that is applied in various commercial processes. The meta‐thesis of functionalized olefins has not yet been commercialized despite its considerable potential. The conversion of oleochemical feedstocks into specialty chemicals appears especially attractive. In this paper, a process scheme is proposed for the production of 1,18‐dimethyl octadecanedioate from pure methyl oleate by metathesis. The chemical and technological bottlenecks are explored, and a rough economic evaluation of this route is given. From these considerations, it is concluded that such a process for the metathesis of functionalized alkenes could be viable only if certain conditions are met. Rapid catalyst deactivation is identified as one of the main obstacles. Feedstock purity, efficient recycling of unreacted feed and multiple catalyst regeneration are crucial for economic feasibility. Rhenium‐based catalysts are to be preferred over molybdenum ones because their activation is easier and regenerability is superior. Finally, the direction for future technological and catalysis research is given based upon the results of this work.

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Zum Einfluß von Schutzgruppen bei der Metathese fettchemischer Verbindungen

Cited by 3 publications

References 16 publications

Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

Self Metathesis of Fatty Alcohols and Amines to Provide Monomers for Polyester and Polyamide Products

Technological and economical aspects of the metathesis of unsaturated esters

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