Addition of glyoxylic acid ethyl ester to unsaturated fatty acid derivatives

Eur. J. Lipid Sci. Technol.

Fiene

Buß

et al. 2000

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The rhodium catalysed hydroaminomethylation of the unsaturated fatty acid derivatives oleic acid ethyl ester (1) and oleyl alcohol (2) with the primary amines hexylamine (3), benzylamine (4), aspartic acid diethyl ester (5) and valinol (6), and with the secondary amine morpholine (7), respectively, proceeds with good to excellent yields. Using primary amines the structure of the reaction products depends on the stoichiometry of the reactants. Performing the reaction of (1) with (3) with an excess of the amine compound the corresponding secondary amine (9) (1:1-adduct) was observed. Working with a 2-fold excess of (1) the tertiary amine (16) (2:1-adduct) was the main product.

Section: Introductionmentioning

confidence: 99%

Hydroaminomethylation of fatty acids with primary and secondary amines — A new route to interesting surfactant substrates

Eur. J. Lipid Sci. Technol.

Fiene

Buß

et al. 2000

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“…The catalytic conversions with petrochemicals, e.g. with short-chain alkenes, is a gorgeous method to obtain branched unsaturated fatty compounds [42][43][44][45][46][47][48][49][50][51]. The starting compound is the conjugated linoleic acid methyl ester, which is formed by "thermal or catalytic" conversion of its two isolated double bonds.…”

Section: Hydrovinylationsmentioning

confidence: 99%

The refinement of renewable resources: New important derivatives of fatty acids and glycerol

Euro J Lipid Sci & Tech

Gomes

2010

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121

During the last years, the industrial significance of renewable resources has highly increased. The ever‐growing use of fossil resources for energy consumption, polymers, fine chemicals and pharmaceuticals and the therefore steadily increasing price favour the substitution of oil and gas by renewable resources. Here, especially products of catalytic functionalisations of vegetable fats and oils such as rapeseed oil, sunflower oil, palm oil or coconut oil play a decisive role. The present article gives a survey of several important catalytic functionalisations of fatty compounds and glycerol resulting in new attractive products. With their emerging properties, they could find a rapid introduction into the chemical market. Particularly the functionalisations via heterogeneous and homogeneous catalysis, like additions, reductions, oxidations and metathesis reactions, will be presented.

Lewis-acid catalysed ene reaction of electrondeficient aldehydes and ketones at unsaturated fatty acid derivatives

Eur. J. Lipid Sci. Technol.

Fiene

2000

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The SnCl4 catalysed reaction of oleic acid ethyl ester (1) with glyoxylic acid ethyl ester (2) or mesoxalic acid diethyl ester (5) proceeds with good results yielding the corresponding 1:1‐adducts. Besides the ene adducts also δ‐lactones are formed by the reaction of (1) with (5). The product yield shows a strong dependency on type and quantity of the Lewis‐acid used. A maximum yield was obtained with a stoichiometric amount of SnCl4. In contrast to the thermal ene reaction about 75% of the yield was attained already during the first 30 min of the reaction.