European Journal of Lipid Science and Technology最新文献

The widespread use of bio-derived lipids as renewable feedstock chemicals requires their synthetic modification for downstream applications. Herein, we demonstrate the use of nitroarenes as photo-responsive oxidants for the synthesis of aldehydes and 1,2-diols from unsaturated fatty acids. This approach addresses the conventional use of hazardous and toxic reagents such as ozone (O₃) and osmium tetroxide (OsO₄). The successful employment of stable and nontoxic nitroarenes in oxidation chemistry is demonstrated on a series of industrially relevant fatty acids including carboxylic acids and their methyl ester equivalents producing oxygen-enriched substrates.

Fatty acids derived from renewable resources, such as vegetable oils, serve as essential feedstocks in various industries, including surfactants, cosmetics, lubricants, and polymers. Although current industrial applications of fatty acids are mainly centered around carboxylate group transformations, recent advancements in biocatalysis have opened new possibilities for converting fatty acids into valuable chemical building blocks. This contribution critically assesses novel biocatalytic transformations of fatty acids, including hydroxylation of the alkyl chain, epoxidation of C═C double bonds, reduction of the carboxylate group, and decarboxylation. These reactions hold great potential for producing important intermediates for chemical synthesis.

Practical Application: The enzymatic valorization of fatty acids offers transformative potential for sustainable oleochemical synthesis, presenting practical applications across various industries. Hydroxylated and epoxidized fatty acids are promising precursors for the production of polyesters, bio-based lubricants, and surfactants. Sophorolipids, derived from hydroxylated fatty acids, are gaining attraction as renewable biosurfactants with applications in detergents and cosmetics. Epoxidized fatty acids serve as intermediates for eco-friendly adhesives, coatings, and polymers. Furthermore, decarboxylation reactions yield alkanes, viable as biofuels, whereas reductions of carboxyl groups enable selective synthesis of aldehydes and alcohols for fragrances and pharmaceutical intermediates. The scalability of these biocatalytic transformations, combined with their mild operational conditions and high specificity, can substantially reduce environmental impact and production costs. These applications highlight biocatalysis as a pivotal technology for advancing the chemical industry toward sustainable practices.

The substitution of depleting fossil resources by renewable resources is of paramount importance, especially for polymer chemistry with its large production volume, in order to guarantee a more sustainable future. Herein, a new three-step reaction sequence was developed to synthesize renewable fatty acid–based dimethyl esters from saturated fatty acids. The sequence consists of a catalytic dehydrogenation with molecular oxygen as oxidant, an esterification with methanol, and a dimerization reaction with dithiols via thia-Michael addition. Three new dimethyl esters were thus synthesized from lauric acid and fully characterized via infrared, ¹H NMR, and ¹³C NMR spectroscopy as well as mass spectrometry. Polyesters with molecular weights ranging from 26.0 to 31.8 kDa were obtained by polycondensation of each dimethyl ester with 1,12-dodecanediol. Methyl crotonate–based polymers were prepared for comparison with the fatty acid–derived materials. Thermogravimetric analysis revealed that the long side chains led to improved thermal stability, and differential scanning calorimetry showed side chain crystallization for one polymer.

Practical Applications Renewable dimethyl esters are valuable monomers for the sustainable synthesis of polyesters and polyamides. The herein-reported synthesis strategy valorized saturated fatty acids, a typically less useful resource for polymer chemistry.

In response to the increasing demand for sustainable materials, this study explores the structure–property relationships of 22 novel diesters synthesized from C2–C4 linear and branched diols and saturated fatty acids (SFAs), targeting the improvement of vegetable oil-based lubricants’ oxidative stability and low-temperature performance. Diesters based on pelargonic (C9), lauric (C12), myristic (C14), and palmitic (C16) acids were characterized for viscosity, crystallization temperature, and flow behavior. Branched diols significantly enhanced low-temperature properties, with 1,2-butanediol and 1,3-butanediol diesters always exhibiting the lowest crystallization temperatures. Viscosity increased with fatty acid chain length, whereas branching caused a slight reduction due to steric hindrance. Most diesters showed shear-thickening behavior, modeled by the Herschel–Bulkley equation. Additionally, all diesters demonstrated excellent oxidative stability, surpassing 300 min in accelerated aging tests. These findings suggest that the synthesized diesters, particularly those with branched diols, offer promise as sustainable, high-performance alternatives for industrial lubricant applications.

Practical Application: The diesters synthesized from saturated fatty acids and C2–C4 diols offer strong potential as bases for bio-based lubricants, particularly in applications requiring high oxidative stability. The esters, particularly those derived from branched diols, exhibit improved cold flow properties, due to their lower crystallization temperatures, making them ideal candidates for use in industries requiring lubricants that perform well in low-temperatures conditions. Their shear-thickening behavior also makes them ideal for shock-absorbing uses. The comprehensive analysis and results presented in this study provide a valuable reference for selecting the optimal combination of fatty acids and alcohols to tailor synthetic esters with specific properties, addressing diverse needs in the lubricant industry. This work serves as a practical guide for developing high-performance, sustainable lubricant formulations.

This study aimed to comprehensively analyze lipid classes after in vitro digestion of high-fat commercial dairy products. The research focused on the fatty acid (FA) profiles of triacylglycerols, diacylglycerols, monoacylglycerols (MAG), free FA (FFA), and polar lipids of digested full-fat cream, full-fat sour cream, cream cheese, and a Gouda-type cheese. We employed the INFOGEST 2.0 digestion model. The isolated lipids were fractionated by solid-phase extraction, and the FA profile of each fraction was analyzed using GC–MS. The digested dairy products revealed similar results for the relative amounts of the analyzed lipid classes. However, the cream digest had a significantly lower amount of MAG than the other products. Furthermore, the proportion of individual FAs and FA groups in the lipid classes was found to vary significantly between the digested dairy products. The replicates of cream cheese and sour cream showed a homogenous lipid digestion, whereas the lipid classes after digestion of cream and the Gouda-type cheese were more diverse. This could be due to differences in product pH and protein and calcium content.

Practical Applications: The findings of our study indicate the importance of considering lipid classes other than FFA, as well as the FA composition of these, when studying the lipid digestion of different dairy products. This is especially true for MAG, which is absorbed in the intestine along with FFA. The observed differences in the lipid profile of the digested dairy matrices explored in our study demonstrate that product pH, homogenization, texture, and calcium and protein content could impact lipid bioaccessibility, which could potentially have physiological implications. These factors should, therefore, be assessed in relation to lipid digestion.