Rhodium‐catalysed cyclisation by addition of unsaturated 1,4‐dicarbonyl compounds to oleic acid methyl ester

Eschig, Steven; Schirp, Claudia

doi:10.1002/ejlt.201500191

Euro J Lipid Sci & Tech

2015

DOI: 10.1002/ejlt.201500191

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Rhodium‐catalysed cyclisation by addition of unsaturated 1,4‐dicarbonyl compounds to oleic acid methyl ester

Steven Eschig

Claudia Schirp

Abstract: The Rh-catalysis allows the one-step synthesis of Diels–Alder-like cycloadducts from mono-unsaturated fatty acid and 1,4-dicarbonyl components. In this article we report on the addition of maleic acid-, fumaric acid- and acetylene dicarboxylic acid dimethyl ester to oleic acid methyl ester. In previous studies, Rh(OAc)2 showed the highest selectivity of the investigated catalysts towards the 3,6-disubstituted-1,2,3,6-tetrahydro-phthalic acid derivatives (THPA) for the addition of maleic anhydride to oleic acid… Show more

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Cited by 2 publications

References 28 publications

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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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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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Highly Water‐Soluble Amphiphilic Cyclodextrins Bearing Branched and Cyclic Oleic Grafts

et al. 2019

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Amphiphilic β‐cyclodextrins bearing various amounts of branched and cyclic oleic grafts are synthetized. The first step of this synthesis is the alkenylation of maleic anhydride by oleic acid derivatives, in the presence of a rhodium catalyst, to produce oleic succinic anhydrides with different ratios of cyclic to branched groups. The second step is the grafting of the oleic succinic anhydrides mixtures on β‐cyclodextrin. The obtained cyclodextrins are highly water‐soluble and surface active.

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Rhodium‐catalysed cyclisation by addition of unsaturated 1,4‐dicarbonyl compounds to oleic acid methyl ester

Cited by 2 publications

References 28 publications

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

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

Highly Water‐Soluble Amphiphilic Cyclodextrins Bearing Branched and Cyclic Oleic Grafts

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