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Extraction of Bio-Based Glycolaldehyde from Wood-Derived Pyrolysis Oils

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Extraction of Bio-Based Glycolaldehyde from Wood-Derived Pyrolysis Oils Extraction of bio-based glycolaldehyde from wood-derived pyrolysis oils Citation for published version (APA): Vitasari, C. R. (2012). Extraction of bio-based glycolaldehyde from wood-derived pyrolysis oils. Technische Universiteit Eindhoven. https://doi.org/10.6100/IR738958 DOI: 10.6100/IR738958 Document status and date: Published: 01/01/2012 Document Version: Publisher’s PDF, also known as Version of Record (includes final page, issue and volume numbers) Please check the document version of this publication: • A submitted manuscript is the version of the article upon submission and before peer-review. There can be important differences between the submitted version and the official published version of record. People interested in the research are advised to contact the author for the final version of the publication, or visit the DOI to the publisher's website. • The final author version and the galley proof are versions of the publication after peer review. • The final published version features the final layout of the paper including the volume, issue and page numbers. Link to publication General rights Copyright and moral rights for the publications made accessible in the public portal are retained by the authors and/or other copyright owners and it is a condition of accessing publications that users recognise and abide by the legal requirements associated with these rights. • Users may download and print one copy of any publication from the public portal for the purpose of private study or research. • You may not further distribute the material or use it for any profit-making activity or commercial gain • You may freely distribute the URL identifying the publication in the public portal. If the publication is distributed under the terms of Article 25fa of the Dutch Copyright Act, indicated by the “Taverne” license above, please follow below link for the End User Agreement: www.tue.nl/taverne Take down policy If you believe that this document breaches copyright please contact us at: [email protected] providing details and we will investigate your claim. Download date: 07. Oct. 2021 Extraction of Bio-based Glycolaldehyde from Wood-derived Pyrolysis Oils C. R. Vitasari Doctoral committee Chairman prof. dr. ir. R. A. J. Janssen Eindhoven University of Technology Promotor prof. dr. ir. A. B. de Haan Eindhoven University of Technology Co-promotor dr. ir. G. W. Meindersma Eindhoven University of Technology Examiners prof. dr. ir. S. R. A. Kersten University of Twente prof. dr. ir. H. J. Heeres University of Groningen prof. dr. ir. E. J. M. Hensen Eindhoven University of Technology prof. dr. J. P. M. Sanders Wageningen UR dr. Yrjö Solantausta VTT Technical Research Centre of Finland dr. T. A. Nijhuis Eindhoven University of Technology The research presented in this thesis was financially supported by the BIOCOUP project 518312, which was supported by the European Commission through the Sixth Framework Programme for Research and Development. Extraction of Bio-based Glycolaldehyde from Wood-derived Pyrolysis Oils Vitasari, C.R. ISBN: 978-94-6108-340-1 A catalogue record is available from the Eindhoven University of Technology Library. Cover photo: Antonius Palintin Printed by Gildeprint Drukkerijen - Enschede Copyright © C.R. Vitasari. The Netherlands. 2012. All rights reserved. Extraction of Bio-based Glycolaldehyde from Wood-derived Pyrolysis Oils PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Technische Universiteit Eindhoven, op gezag van de rector magnificus, prof.dr.ir. C.J. van Duijn, voor een commissie aangewezen door het College voor Promoties in het openbaar te verdedigen op donderdag 25 oktober 2012 om 16.00 uur door Caecilia Rining Vitasari geboren te Tanjung Karang, Indonesië Dit proefschrift is goedgekeurd door de promotor: prof.dr.ir. A.B. de Haan Copromotor: dr.ir. G.W. Meindersma Summary Biomass is a potential source of renewable energy and chemicals. Biomass pyrolysis yields oil, gas, and char. Pyrolysis oil contains water and a considerable amount of bio- based platform chemicals, such as acetic acid, glycolaldehyde, acetol, levoglucosan, sug- ars, and phenolic compounds. Glycolaldehyde is one of the most abundant compounds in pyrolysis oil (5-13 wt%). It is a promising intermediate for producing bio-based ethylene glycol via fermentation. This research focuses on the isolation of glycolaldehyde from wood-derived pyrolysis oils, i.e. forest residue- and pine-derived pyrolysis oils. Glycolaldehyde recovery is challenging since pyrolysis oil is a complex mixture of more than 300 oxygenated compounds with close boiling points. Furthermore, pyrolysis oil is chemically unstable, which makes distillation unfeasible. Therefore, extraction is expected to be a more promising separation method. To address these technical challenges, this research aims to develop an extraction-based separation process to isolate glycolaldehyde from wood-derived pyrolysis oils. In this thesis wood-derived pyrolysis oils are represent- ed by forest residue- and pine-derived pyrolysis oils. Direct glycolaldehyde extraction from pyrolysis oil with sodium bisulfite is not appli- cable due to the stable glycolaldehyde-bisulfite adduct. Therefore, water extraction of pyrolysis oil is employed as the initial step where glycolaldehyde and other polar com- pounds are isolated in the aqueous phase. The investigation was done at various stirring rates and water-to-oil ratios. The stirring rate does not affect either the equilibrium com- position or the extraction performance. Van Krevelen diagrams show that the elemental distributions of pyrolysis oil between the two phases are independent of the water-to-oil ratio. These diagrams also indicate that water extraction is able to significantly decrease the hydrogen and oxygen contents of the forest residue- and pine-derived pyrolysis oils. The characteristics of pyrolysis oil feedstock determine the optimum water-to-oil ratio, which is in the range of 0.65-0.7 for forest residue-derived pyrolysis oil and 0.5 for pine- derived pyrolysis oil. Water extraction is not selective but capable to extract 80-90% of the polar com- pounds present in the pyrolysis oil feedstocks in the aqueous extract phase. This aqueous mixture is the starting material for further treatment to isolate a particular bio-based chemical. On the other hand, the organic raffinate phase can be further extracted to re- cover phenolic fractions, which can be applied in the production of plywood and particle board. The first alternative to extract glycolaldehyde from the pyrolysis oil-derived aqueous phase is reactive extraction with primary amines dissolved in organic diluents. Glycolalde- hyde dissolves in the organic phase where it reacts with a primary amine extractant to form a corresponding imine according to the Schiff-base mechanism. Several combina- tions of amine extractants and organic diluents have been investigated to select promising solvent candidates. The ability of long chain alkane and alcohol diluents to dissolve glycolaldehyde reduc- es with the chain length in the following order: 1-octanol > 1-decanol > oleylalcohol > n-hexane > dodecane. The extraction capability of amine extractants declines as follows: octylamine > 4-ethylaniline > phenylethylamine >> Primene JM-T > 2-ethylaniline. Taking into consideration the reversibility of the Schiff-base formation, Primene JM-T and 2-ethylaniline are chosen as promising extractant candidates. An excess amount of amine is necessary to significantly improve the distribution coef- ficient and achieve maximum single stage extraction yield. When a particular extractant is supplied in excess, for example at a concentration of 2 M Primene JM-T or 2-ethylaniline and a solvent-to-feed ratio of 2, the diluent has a minor influence on the extraction per- formance. Thus, in this case any organic diluents can be used as long as they are insoluble in water and able to dissolve the formed imine. In addition, 1H NMR spectra confirm that only Schiff-base formation takes place. E/Z isomerisation also occurs, but it does not form a new substance. The Schiff-base formation is theoretically reversible and selective with a relatively high glycolaldehyde yield. However, the regeneration process is challenging, mostly due to imine stability and the nature of the organic phase. Thus, an antisolvent-induced regener- ation method has been proposed. Imine solubility in the organic phase could be decreased by adding an antisolvent. The precipitated imine could be then stripped with a mixture of water and catalyst to enhance imine hydrolysis. The second alternative is to extract the pyrolysis oil-derived aqueous phase with either 2-ethyl-1-hexanol or a solution of tri-n-octylamine (TOA) in 2-ethyl-1-hexanol. Both solvents are able to extract acetic acid and co-extract glycolaldehyde simultaneously. The effects of feed and TOA concentrations on the extraction performance have been investi- gated in a mixture of up to 12 wt% acetic acid and glycolaldehyde in water. In the physical extraction with 2-ethyl-1-hexanol, acetic acid has about a fourfold higher distribution coefficient than glycolaldehyde within the studied concentration range. These distribution coefficients are only slightly affected by the feed composition. Furthermore, it has been proven that acetic acid and glycolaldehyde are extracted inde- pendently from each other. Besides acetic acid and glycolaldehyde also water is co- extracted into the organic phase with a concentration higher than its saturated concentra- tion of
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