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Item type:Publication, Access status: with files , Structure-performance guided design of sustainable plasticizers from biorenewable feedstocksThe search for more sustainable solutions for plastics production, moving away from petrochemical feedstocks as today's major raw material basis, is a research area of increasing interest. This task goes far beyond the issue of designing greener polymers and their related monomers as tailor-made plastics require, besides the polymer itself, further components. These additives also need to be switched from typically fossil-based to bio-renewable raw materials. One of such necessary components for many applications are plasticizers, and a major application of them is related to polyvinyl chloride (PVC) as one of the leading polymers with a wide range of applications. Typically today‘s plasticizers are based on fossil feedstocks, and some of them such as specific ortho-phthalates as the most important product class of plasticizers are now subject to restrictions and authorization by the EU's REACH legislation due to their toxicological profile. In this contribution, we report the synthesis and technical evaluation of alternative, novel bicyclic plasticizer candidates, which are fully accessible from renewable feedstocks. In detail, these new plasticizer target molecules are based on the use of the furan-derivative 2-methylfuran, maleic anhydride and 2-ethylhexanol as bio-based starting materials. The synthetic concept consists of an initial Diels-Alder reaction with 2-methylfuran and a subsequent hydrogenation and optional esterification step. The applied reactions are well-known as economic and sustainable technologies. Thus, not only the starting materials (being of bio-based origin) but also the selected reaction technologies for the syntheses of the target molecules are sustainable. Furthermore, a range of performance tests enabled an insight into structure-performance relationships and revealed promising plasticizing properties of this new bio-based plasticizer generation with, e. g., an attractive solution temperature fulfilling the criterium for a “fast fuser” as well as good compatibility with PVC.Publicationtype: Journal ArticleScopus© Citations 4 70 277 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, Access status: without files , Towards bio-based plasticizers with reduced toxicity: Synthesis and performance testing of a 3-methylphthalate(2020-12); ; ; ; As a very durable material, soft polyvinyl chloride (PVC) is used for many applications in the field of consumer products. To enable the desired properties, for example for medical devices, the addition of plasticizers is required. For this purpose, mostly dialkyl phthalates are used being produced on a multi-million tons scale annually. Since some of these are associated with human health effects, there is an increasing demand for the search of alternatives. Besides reduced toxicity while maintaining excellent performance features, an economic access as well as biorenewable starting materials are further criteria, which should be ideally fulfilled by such a new plasticizer generation. Targeting these demands and in contrast to most available substitutes being based on petrochemical feedstock, we developed a synthetic route starting from bio-renewable platform chemicals. In detail, a Diels-Alder reaction of 2-methylfuran and maleic anhydride and subsequent dehydration leads to three phthalate derivatives with different alcohol components bearing a methyl group at the aromatic ring. As a representative substance, di(2-ethylhexyl) 3-methylphthalate was chosen for performance tests, and this new bio-based alternative offers properties similar to known plasticizers in such initial studies.Publicationtype: Journal Article158 - Some of the metrics are blocked by yourconsent settings
Item type:Publication, Access status: without files , FTIR based kinetic characterisation of an acid-catalysed esterification of 3-methylphthalic anhydride and 2-ethylhexanol(2020-06-28); ; ; ; In this study, an inline analytical method was designed and applied in process characterisation and development. The model reaction is the two-step diesterification of 3-methylphthalic anhydride with 2-ethylhexanol consisting of alcoholysis as the first step, followed by an acid-catalysed, second esterification step leading to the corresponding diester. The final product is a potential, alternative plasticiser. For the inline measurements, attenuated total reflection Fourier transformed infrared spectroscopy (ATR-FTIR) was implemented. In order to evaluate the spectra recorded during the reaction, a chemometric model was established. In this work, Indirect Hard Modeling (IHM), a non-linear modeling approach was employed. The respective model was calibrated by using offline samples analysed with gas (GC) and liquid chromatography (HPLC). After successful validation of the chemometric model, the inline measurements were utilized for reaction characterisation. The acid-catalysed, second esterification step was identified as the limiting reaction step. From batch reactions conducted at different temperatures, the energy of activation of this step was determined to be 79.5 kJ mol-1. Additionally, kinetics were shown to follow a pseudo-first order with respect to the monoester formation and a kinetic model was established. The model was validated in simulations with changed reaction conditions.Publicationtype: Journal Article111