Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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    Endocrine activities of phthalate alternatives; Assessing the safety profile of furan dicarboxylic acid esters using a panel of human cell based reporter gene assays
    Vugt-Lussenburg, Barbara M.A. Van; Es, Daan S. Van; Naderman, Matthijs ; Notre, Jerome Le; Klis, Frits Van Der; Brouwer, Abraham ; Burg, Bart Van Der - \ 2020
    Green Chemistry 22 (2020)6. - ISSN 1463-9262 - p. 1873 - 1883.

    FDCA esters are highly relevant biobased alternatives for currently used benzene dicarboxylic acid esters. Despite all the developments on 2,5-FDCA applications, to the best of our knowledge thus far no toxicological data were available for 2,5-FDCA esters. In the present study we aimed to fill this gap, by using an in vitro reporter gene assay approach to compare the activity profile of commonly used phthalates to that of their furan-based counterparts. The assay selection was aimed at the detection of endocrine activity, since several phthalates are heavily scrutinised for their endocrine disrupting properties. However, to avoid missing other relevant toxicological endpoints, several assays able to detect various forms of cellular stress were also included in the panel. The results showed that the (ortho)benzene dicarboxylic acid esters were predominantly active on several of the endocrine assays. In comparison, six of the seven furan dicarboxylic acid based diesters tested here showed no activity in any of the 13 assays used. Only the isobutyl derivative DIBF showed moderate estrogenic activity on one assay, compared to much more pronounced activities on four assays for the ortho-phthalate analogue. Overall, the results presented in this paper are a strong indication that 2,5-FDCA based diesters in general are not only technically viable alternatives to phthalates, but also offer significant toxicological benefits, which supports a non-regrettable substitution.

    Towards an Industrial Process for Au-Catalyzed Carbohydrate Oxidations: Evaluation of Batch- vs. Continuous Reactors
    Klis, Frits van der; Gootjes, Linda ; Haveren, Jacco van; Es, Daan van; Bitter, Harry - \ 2019
    Conversion of SBP components into value added products for home & personal care and performance materials
    Es, Daan van; Klis, Frits van der - \ 2019
    Surface active compound
    Ranoux, Adeline ; Raaijmakers, H. ; Lazeroms, R. ; Klis, F. van der; Es, D.S. van - \ 2019
    Octrooinummer: WO2019162469, gepubliceerd: 2019-08-29.
    The present invention relates to novel surface active compounds based on polyhydroxy acids. The compounds are of formula (I), where X represents hydrogen or a cation; n is 4 and Y represents a group of formula (II) or formula (III), wherein at least one one of R1, R2 and R3 is a surfactant tail group, wherein the moiety represented by formula (Ι') represents the residue of galacturonic acid, and are generally easy to prepare by derivatization of polyhydroxy acids obtained from renewable resources such as, in particular, parenchymal plant materials. The invention relates to the surface active compounds, compositions comprising the same, methods of production and different uses of the surface active compounds. (l'), (l), (ll), (lll)
    Treatment of leather including employing pectin
    Ma, Y. ; Ehrhart, W. ; Klis, F. van der; Mulder, W.J. ; Haveren, J. van - \ 2019
    Octrooinummer: WO2019185824, gepubliceerd: 2019-10-03.
    The invention concerns a method for manufacturing leather including employing pectin and leather thus obtained, in particular leather impregnated with pectin.
    Net energy in poultry: Its merits and limits
    Klis, J.D. van der; Jansman, A.J.M. - \ 2019
    Journal of Applied Poultry Research 28 (2019)3. - ISSN 1056-6171 - p. 499 - 505.
    AME - ATP - Broiler - Net Energy - Production performance

    Development of a net energy (NE) system in poultry has been a topic of research for many decades, following its successful implementation in pigs. However, up to now, no such system for poultry is in use, as the added value of a NE system in poultry over the current AME system(s) has not yet been demonstrated. In this paper, the merits and limits of a NE system in poultry are discussed for fast-growing broilers.

    The effect of me-substituents of 1,4-butanediol analogues on the thermal properties of biobased polyesters
    Klis, Frits van der; Knoop, Rutger J.I. ; Bitter, Johannes H. ; Broek, Lambertus A.M. van den - \ 2018
    Journal of Polymer Science. Part A, Polymer Chemistry 56 (2018)17. - ISSN 0887-624X - p. 1903 - 1906.
    biobased-building blocks - glass transition - polyesters - structure–property relations
    Biobased 1,4‐butanediol analogues are used to tune the glass transition temperature and crystallization in a series of polyesters, and allow for the formation of stereocomplexes.
    Base-free selective oxidation of pectin derived galacturonic acid to galactaric acid using supported gold catalysts
    Pazhavelikkakath Purushothaman, Rajeesh Kumar ; Klis, F. van der; Frissen, A.E. ; Haveren, J. van; Mayoral, A. ; Bent, A. van der; Es, D.S. van - \ 2018
    Green Chemistry 20 (2018)12. - ISSN 1463-9262 - p. 2763 - 2774.

    Agricultural residues like sugar beet pulp (SBP) are an interesting feedstock for the production of 2nd generation bio-based chemicals and materials. The pectin fraction of SBP is rich in galacturonic acid (GalA), a C6 sugar acid. The oxidation of this uronic acid at C1 yields galactaric acid (GA), which has several industrially interesting properties. It was previously shown that the Au catalysed oxidation of uronic acids under basic conditions is highly effective, yet leads to the co-production of salts. Hence, here we report for the first time on the oxidation of an acidic carbohydrate substrate, GalA, at its autogenic pH (2.2) in water, using carbon supported gold nanoparticles, under mild conditions in the presence of molecular oxygen. The comparison of the Au/C catalyst prepared by a colloidal deposition method with benchmark commercially available metal oxide supported gold catalysts shows that under acidic conditions, the Au/C catalyst is more active and more selective than Au/TiO2, and more stable than Au/Al2O3. The difference in selectivity is attributed to the H2O2 mediated chain scission reaction of the substrate (GalA) which is observed only in the case of metal oxide supported Au catalysts. The Au/C catalyst shows 100% GA selectivity at 76% GalA conversion (333 K, 21 h batch time) and a GA yield of up to 95% was obtained at 353 K. Detailed characterization of the fresh and spent Au/C catalysts by ICP-OES, TEM and XPS analyses showed no gold leaching, particle sintering or change in metal composition. The Au/C catalyst was fully regenerated by a mild alkaline wash, and used in five consecutive runs without any significant decrease in activity or selectivity. Labelling experiments with 18O2 and H2 18O2 revealed that under base-free conditions, the oxygen incorporated in the aldaric acid originates from the solvent water.

    From batch to continuous : Au-catalysed oxidation of d-galacturonic acid in a packed bed plug flow reactor under alkaline conditions
    Klis, F. van der; Gootjes, L. ; Haveren, J. van; Es, D.S. van; Bitter, J.H. - \ 2018
    Reaction Chemistry & Engineering 3 (2018)4. - ISSN 2058-9883 - p. 540 - 549.

    Currently biomass based conversions are often performed in batch reactors. From an operational and economic point of view the use of a continuous plug flow reactor is preferred. Here we make a back to back comparison of the use of a batch and plug flow reactor for the oxidation of (sodium)-galacturonate to (disodium)-galactarate using a heterogeneous Au-catalyst. We will show that the use of a three phase plug flow reactor results in enhanced O2 mass transfer which resulted in a 10-40 fold increase in productivity (up to 2.2 ton m-3 h-1). However, the product selectivity slightly dropped from >99 mol% in batch (controlled pH) to 94 mol% in packed bed (uncontrolled pH). Both reactors suffer from the low solubility of the reaction product. We will show that this solubility is the most significant challenge for performing this oxidation on industrial scale.

    Methyl Perillate as a Highly Functionalized Natural Starting Material for Terephthalic Acid
    Jongedijk, E.J. ; Klis, F. van der; Zwart, Rozemarijn de; Es, D.S. van; Beekwilder, M.J. - \ 2018
    ChemistryOpen 7 (2018)2. - ISSN 2191-1363 - p. 201 - 203.
    Renewable commodity chemicals can be generated from plant materials. Often abundant materials such as sugars are used for this purpose. However, these lack appropriate functionalities and, therefore, they require extensive chemical modifications before they can be used as commodity chemicals. The plant kingdom is capable of producing an almost endless variety of compounds, including compounds with highly appropriate functionalities, but these are often not available in high quantities. It has been demonstrated that it is possible to produce functionalized plant compounds on a large scale by fermentation in microorganisms. This opens up the potential to exploit plant compounds that are less abundant, but functionally resemble commodity chemicals more closely. To elaborate this concept, we demonstrate the suitability of a highly functionalized plant compound, methyl perillate, as a precursor for the commodity chemical terephthalic acid.
    Synthesis of Furandicarboxylic Acid Esters From Nonfood Feedstocks Without Concomitant Levulinic Acid Formation
    Klis, Frits van der; Haveren, Jacco van; Es, Daan S. van; Bitter, Harry - \ 2017
    ChemSusChem 10 (2017)7. - ISSN 1864-5631 - p. 1460 - 1468.
    Furandicarboxylic acid - Isomerization - Levulinic acid - Oxidation - Uronic acids

    5-Hydroxymethylfurfural (HMF) is a versatile intermediate in biomass conversion pathways. However, the notoriously unstable nature of HMF imposes challenges to design selective routes to chemicals such as furan-2,5-dicarboxylic acid (FDCA). Here, a new strategy for obtaining furans is presented, bypassing the formation of the unstable HMF. Instead of starting with glucose/fructose and thus forming HMF as an intermediate, the new route starts from uronic acids, which are abundantly present in many agro residues such as sugar beet pulp, potato pulp, and citrus peels. Conversion of uronic acids, via ketoaldonic acids, to the intermediate formylfuroic acid (FFA) esters, and subsequently to FDCA esters, proceeds without formation of levulinic acid or insoluble humins. This new route provides an attractive strategy to valorize agricultural waste streams and a route to furanic building blocks without the co-production of levulinic acid or humins.

    Oxidation of uronic acids to aldaric acids
    Es, D.S. van; Pazhavelikkakath Purushothaman, R.K. ; Frissen, Guus ; Klis, F. van der - \ 2016
    Octrooinummer: WO2016056907, gepubliceerd: 2016-04-14.
    Disclosed is the oxidation of uronic acids, such as galacturonic acid, to the corresponding aldaric acids, such as galactaric acid, under neutral or acidic conditions. Use is made of a supported gold catalyst. The oxidation occurs in good selectivity and yield, under unexpectedly mild conditions. A source of galacturonic acids is pectins, such as from sugar beet pulp.
    Novel catalytic route from agro-residues to furan-2,5-dicarboxylic acid
    Klis, Frits van der - \ 2016
    Novel catalytic route from agro-residues to furan-2,5-dicarboxylic acid
    Klis, Frits van der - \ 2016
    Structure-property relations of biobased polyesters from 1,4-butanediol-analogues and biobased diacids
    Klis, Frits van der - \ 2016
    Chemistry As INnovating Science (CHAINS)
    Klis, Frits van der - \ 2016
    Structure-property relations of biobased polyesters from 1,4-butanediol-analogues and biobased diacids
    24 th European Biomass Conference and Exhibition Amsterdam
    Klis, Frits van der - \ 2016
    Novel catalytic route from agro-residues to furan-2,5-dicarboxylic acid
    NCCC XVII The Netherlands' Catalysis and Chemistry Conference
    Klis, Frits van der - \ 2016
    Novel catalytic route from agro-residues to furan-2,5-dicarboxylic acid
    Integration of galacturonic acid extraction with alkaline protein extraction from green tea leaf residue
    Zhang, Chen ; Bozileva, Elvira ; Klis, Frits van der; Dong, Yiyuan ; Sanders, Johan P.M. ; Bruins, Marieke E. - \ 2016
    Industrial Crops and Products 89 (2016). - ISSN 0926-6690 - p. 95 - 102.
    Biorefinery - Cellulase - Cost estimation - Experimental design - Leafy biomass - Recycle system

    Leaf pectin can be used as a feedstock for galacturonic acid (GA) production, but high extraction costs limit economic feasibility. To improve the extraction efficiency, leaf pectin extraction was integrated with an already cost-effective alkaline protein extraction, focusing on high yield of GA without losses of protein. GA extraction efficiencies in NaOH, HCl, phosphate buffer solution, or with Viscozyme® L were determined using green tea residues (GTR) as model material. Most GA was extracted using Viscozyme® L, mainly due to its cellulase activity. Extraction yielded more than 95% GA with only 5% protein. Alternatively, GA-containing pectin can be extracted in a weak alkaline solution. Here, GA yield is dominated by the ratio of extraction volume to biomass weight. The profits of these two integrated processes can be higher than one step protein extraction. The Viscozyme® L integrated process is suitable for GA production for application in chemicals, and may have a profit of 142$/ton GTR when enzyme cost are sufficiently lowered. The profit of the weak alkaline integrated process is estimated at 118$/ton GTR.

    NCCC XVI The Netherlands' Catalysis and Chemistry Conference
    Klis, Frits van der - \ 2015
    Heterogeneous selective terminal C-C scission of C5-carbohydrates
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