Diels‐Alder‐Reaktionen auf dem Fettgebiet

Kaufmann, h. c. H. P.

doi:10.1002/lipi.19620641209

Fette, Seifen, Anstrichm.

1962

DOI: 10.1002/lipi.19620641209

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Diels‐Alder‐Reaktionen auf dem Fettgebiet

h. c. H. P. Kaufmann¹

Abstract: Vf. bespricht die Diels‐Alder‐Reaktionen auf dem Fettgebiet und behandelt in systematischer Reihenfolge „Diene”︁ (Konjuen‐Fettsäuren, Konjuen‐Fettalkohole, Konjuen‐Fettaldehyde) und „dienophile Partner”︁. Anschließend wird auf die Bedeutung der Dien‐Synthese für die Fettanalyse, die Strukturforschung und die Anwendungsmöglichkeiten der Dien‐Systeme auf dem Fettgebiet zu technischen und präparativen Zwecken eingegangen.

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Cited by 6 publications

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Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives byDiels-Alder reactions at unsaturated fatty esters

Behr¹,

Fiene²,

Naendrup³

et al. 2000

Eur. J. Lipid Sci. Technol.

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Diels‐Alder reactions of conjugated linoleic acid ethyl ester (1) with different quinones and with a variety of α/βunsaturated aldehydes and ketones are described in this paper. Using Sc(OTf)3 or Cu(OTf)2 as catalysts the reactions can be carried out at 25—40 °C with good yields. For the first time in oleochemistry it is possible to prepare Diels‐Alder cycloadditions with catalyst concentrations of 10 mol‐% instead of stoichiometric amounts of Lewis acids. Furthermore, the reaction time was partly shortened drastically. The catalyst Sc(OTf)3 can be removed by a simple extraction of the organic layer with water. After evaporation of the aqueous phase to dryness the catalyst can be reused without loss of yield.

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Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives byDiels-Alder reactions at unsaturated fatty esters

Behr¹,

Fiene²,

Naendrup³

et al. 2000

Eur. J. Lipid Sci. Technol.

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An Industrial Applicable Method for the Synthesis of N‐alkylated Maleimides Based on Fatty Amines

Schmidt

Eschig

2018

Euro J Lipid Sci & Tech

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A simple and economic two step synthesis of N‐alkylated maleimides with repeatable recycling of recovered starting materials from the second step is developed. In the first step, maleic anhydride is reacted with different natural mixtures of bio‐based fatty amines to give the corresponding maleic acid alkyl amides. The formation of the 5‐membered maleimide‐rings is achieved via acid‐catalyzed intramolecular condensation. However, in this step only 50–64% of the used alkyl amides are converted toward the required N‐alkylated maleimides. The novelty of our approach is the continuous recycling of recovered non‐converted amides for additional cyclization steps. These steps are repeated several times, whereby the yields of maleimides for each step leveled off at 46–50%. Practical Applications: Click reactions have become more and more prominent in the field of material science. A relevant used example is the [4 + 2]‐cycloaddition of maleimides and furans, whereby both moieties can be attached to the polymer backbone. This is a promising approach for the introduction of new functionalities to a polymer by a simple addition reaction. For this purpose a polymer, which contains furan groups and a functionalized maleimide are needed. For example, the use of fatty acid based maleimides allows the introduction of hydrophobic properties to a furan‐functionalized polymer, due to their long alkyl chain. However, the functional group of the maleimide can be varied to introduce other properties, like antimicrobial, hydrophilic or combinations thereof. This technique is interesting for coatings and allows the adaption of surface properties in a wide range. Moreover, maleimides can be used as polymerizable monomers to synthesize high performance macromolecular systems like polymers with high thermal stability. Synthesis of fatty acid based maleimides starting from maleic anhydride and fatty amines. This technique is interesting for coatings and allows the adaption of surface properties in a wide range. Moreover, maleimides can be used as polymerizable monomers to synthesize high performance macromolecular systems like polymers with high thermal stability.

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Dien‐Synthesen auf dem Fettgebiet, VII. Mitteilung: Die Reaktion trocknender Öle mit Äthylen und Homologen

Kaufmann

Büscher

1963

Fette, Seifen, Anstrichm.

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Azis dern Deutschen Institut fur Fettforschung, Munster (Westf.) Niedere, gasformige Olefine -Athylen, Propylen und Butylenwurden bei erhohtem Druck und erhohter Temperatur nach Art der DIELS-ALDER-Synthese unter Ausbildung hydroaromatischer Systeme an ungesattigte Fettsaure-methylester und Polyenole addiert. La reaction Diels-Alder dam le domaine des lipides. Communication 2. La reaction des huiles siccatives avec l'ethylhne et ses homologues Des olefines inferieures gazeuses: ethylene, propylene et butylene ont ete condensees sous une pression et h una temperature elevees, suivant la synthPse Diels-Alder, sur des esters methyliques d'acide gras insature et des huiles polyeniques et ont fourni des systemes hydroaromatiques.

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Diels‐Alder‐Reaktionen auf dem Fettgebiet

Cited by 6 publications

References 48 publications

Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives byDiels-Alder reactions at unsaturated fatty esters

Transition-metal trifluoromethane-sulphonates-recyclable catalysts for the synthesis of branched fatty derivatives byDiels-Alder reactions at unsaturated fatty esters

An Industrial Applicable Method for the Synthesis of N‐alkylated Maleimides Based on Fatty Amines

Dien‐Synthesen auf dem Fettgebiet, VII. Mitteilung: Die Reaktion trocknender Öle mit Äthylen und Homologen

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