Processing Swedish lignocellulosic residual material to furan pre-cursors. Furu2Furan

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1 Processing Swedish lignocellulosic residual material to furan pre-cursors Furu2Furan Dennis Jones, Bror Sundqvist SP Wood Technology / EcoBuild Sune Wännström SP Energy Technology William Mackintosh, Johan Malmberg, Anna Stenemyr SP Process Development

2 Furu2Furan Consortium comprising whole value chains Companies members of EcoBuild Competence Center (Competence centre for eco-efficient and innovative wood-based materials)

3 SP A uniting hub in Bioeconomy Vision SP shall be a uniting force and a central resource contributing with knowledge, research resources and management, test facilities and coordination of bioeconomy initiatives in Sweden BIO- ECONOMY SP PROCESS DEVELOPMENT

4 Why are we doing this? Today: too much focus on biofuel production (which may not be the optimal use of the whole biomass) The furanic route to platform chemicals and high-value commodities is almost neglected in current biorefinery development There are some potential winners for the future biobased economy but need to secure that enough chemicals for these is produced in future biorefineries

5 The biorefinery concept Jan van Dam, COST FP1205 presentation 2013

6 The biorefinery concept Furu2Furan High value chemicals Jan van Dam, COST FP1205 presentation 2013

7 Furu2Furan concept

8 Softwoods yield hexoses

9 Hardwoods and agri-fibres yield pentoses

10 Some pathways

11 Conversion of HMF 2-hydroxymethylfuran Platform chemical 2,5-Furandicarboxylic acid Monomer for polymer production 2,5-Dimethylfuran Bio-fuel Methylfuran Bio-fuel 5-hydroxymethylfurfural (HMF) 2,5-Dimethyltetrahydrofuran Solvent 2,5-bis(hydroxymethyl)furan Monomer for polymer production Levulinic acid Bulk chemical Formic acid Bulk chemical

12 High-value end products of the F2F project Furfurylated wood (Kebony) with aesthetic appearance and performance similar to durable tropical timbers (and preservative treated timbers) - European market for durable hardwood (tropical timber): 6 million m³/year => value: 6 billion Euro - European market for preservative treated wood: 6 million m³/year => value: 1.5 billion Euro Coil Coatings (currently 99.9% fossil resource based). BioCoilCoat aims at 60% biobased. SSAB alone use 4 kton/year (?): worth 20 million Euro European market: 100 kton/year (?): worth 550 million Euro Thermoset composites today 99% fossil based European market: 10 billion Euro worth? bioderived resins can replace fossil based resins for many products

13 Possible high-value bulk chemicals from the F2F project Maleic anhydride (currently 100% fossil based) - Global production: worth 550 million Euro Thermoset polyesters & polymerisat. catalyst Adipic acid (currently 100% fossil based) Global annual production: 2.3 million ton Worth: 845 million Euro Caprolactone (currently 100% fossil based Perstorp production (largest producer globally): 12 kton/year? Perstorp caprolactone sales worth 60 million Euro/year Hexane diol (currently 100% fossil based) BASF production (largest producer globally): 50 kton/year Worth: 310 million Euro Polyamide (Nylon) Aviation fuel (currently 100% fossil based). Possibly DMFu Global annual prod of Jet fuel: 5 million barrels worth 500 million Euro e.g. Shoe soles, Medical plastics Polymer building block for e.g. PUR and PE ( Green aromatic solvents ) Global prod. of BTX: 87 Mton worth 91 billion Euro (BTX means Benzene, Toluene, Xylenes)

14 Starting materials A. Under-utilized forest products streams Saw dust Residuals from forest harvesting (stubs, tops and branches) Prehydrolysate from dissolving pulp production TMP and CTMP process water

15 Starting materials B. Under-utilized agricultural byproduct streams Wheat straw Wheat bran Straw and bran from other Lantmännen crops

16 Lab scale work: SP-PD Chemical Processes: Xylose to Furfural Furfural From Hemicellulose Furfuryl alcohol Furfural: Extracted from hydrolysate or transformed from isolated sugar Industrial production in China, South Africa, Dominican republic

17 Lit review from C5, xylose and furfural Showed that furfural is currently being produced commercially from bagasse and/or corn stover Inexpensive, high yields, tuned catalysts and conditions However not from wheat straw. Patents and publications containing furfural and wheat straw Conclusions from literature More severe conditions, time, temp, acid: more furfural Milder conditions: more xylose to then produce furfural in a 2nd step.

18 Experimental Step 1: Wheat straw and dilute sulfuric acid added to a microwave vial (10-20 ml) run under mild conditions. The slurry was filtered, the filtrate analyzed, then used in step 2. Microwave reactor Step 2: Filtrate & methyl isobutyl ketone (MIBK) combined in microwave vial (2-5 ml) High temps and short reaction time Analysis of furfural yield by HPLC and/or LCMS RP-HPLC

19 Results- mild prehydrolysis of wheat straw on the lab scale Step 1: From mild conditions: A range of results is observed in furfural and xylose content The filtrate was then further reacted in step 2

20 Filtration:Processum Pilot Park - Örnsköldsvik Liquid-liquid extraction Filter press Reactor system for synthesis Spinning unit

21 Results step 2-Conversion of xylose to furfural Higher temperatures: Highest yields of furfural were achieved from the mildest hydrolysis runs from step 1. 72% yield obtained (78% in total, Aq phase included) Yield in organic phase

22 Literature Study of C6 sugars to HMF Glucose is a sugar from cellulose and hemicellulose Similar to mannose found in hemicellulose Fructose to HMF Vast amount of information in literature- 8 k items in scifinder. Little in terms of Scaling up and production processes Many catalysts for fructose to HMF Not much reported regarding glucose to HMF Fewer catalysts to convert glucose to HMF Lower yields from glucose

23 Experimental Work Flow for C6 sugars Conditions and catalysts screened on a small scale Via microwave in 2-5 ml vials Analysis of HMF performed by HPLC and/or LCMS Reaction of fructose to HMF first investigated Higher yields and much broader range of possibilities Catalysts screened Then glucose to HMF investigated With use of knowledge obtained from fructose trials

24 Outline of the Experimental Parameters Considered Catalyst Soluble or insoluble Reaction phase biphasic (both water and solvent) vs. single phase Ratio of water to solvent in biphasic system Aqueous Phase Ionic Strength Agitation Solvent type Concentration of sugar in the water phase Temperature Time Replacing the solvent at intervals

25 Screening of Catalysts Less than desirable yields from: Zeolites, Ag and Cs based polyacids, phosphorylated niobium oxide, sulphuric acid 2 Best performers with fructose: Phosphorylated Tantalum hydroxide vs. Calcium phosphate (CaP 2 O 6 ) Next in trials with glucose: Only 20% yield compared to 27% yield w same conditions Glucose to HMF, 190 o C, 20 min, 3 ml MIBK to 2 ml H 2 O *Daorattanachai, P. et al. Conversion of fructose, glucose, and cellulose to 5-hydroxymethylfurfural by alkaline earth phosphate catalysts in hot compressed water, Carbohydrate Research, 363 (2012) * Yang, F. et al. Tantalum compounds as heterogeneous catalysts for saccharide dehydration to 5-hydroxymethylfurfural. Chemical Communications, 47 (2011)

26 Reaction phases Biphasic gave the best yields, with the solvent extracting HMF Inhibits degrading/polymerizing of HMF in the water phase as it is extracted HMF + hydrated HMF Polymer (Humins) formation HMF + glucose Ratio of solvent to water likely requires optimization depending on the system solvent:h2o optimum at 3:2 or 4:1 Higher concentrations of sugar in water does create more insoluble hummins and side reactions * Rasmussen, H. et al. Formation of degradation compounds from lignocellulosic biomass in the biorefinery: Sugar reaction mechanisms, Carbohydrate Research, 385 (2014)

27 Agitation Agitation is very important Creates maximum contact between the 2 phases. Important to transfer HMF from the aqueous phase Decreases HMF degradation and polymerization Catal yst *More humins with scale up in 20 ml microwave vial Alternative to agitation in larger scale processing could be sonication

28 Solvent type Extraction solvent is important Extracts HMF from water M-THF: 8% HMF yield from glucose MIBK: 27% 2-butanol: 30%, and 2% less HMF in water phase Catal yst 2-butanol gave best results, but similar to MIBK or Glucose Is MIBK better for continuous processing? water -2-butanol dissolves a large amount of

29 Concentration of Sugar in the Aqueous Phase The higher the concentration, the lower the yield Due to HMF coming in contact with glucose and itself to form humins This will also require optimization depending on the system 30 wt% glucose in water creates a large amount of side products Determined by HPLC Also much lower yields 6 wt% glucose in water used in most trials to provide high yields of HMF

30 Scaling up: Pretreatment reactor Built for 230 C and 30 bar Heated by steam (22bar) Used for batch reactions

31 Both Mild and Harsh systems for wheat straw scaled up in the Demo-Plant Test Production time Demo Run Plan Target: collecting 100 litres of xylose rich hydrolysate and 100 litres of furfural rich hydrolysate after dilute acid hydrolysis of wheat straw. Temperature Acid Load Residence time Sampling Unit h C % min Litres , , ,2-0, ,

32 Biorefinery Demo Plant

33 Demo plant Domsjö Biorefinery site

34 Demo Plant Facts Fully integrated process from feedstock to distilled product Operated 24h/ 7d Two continuous flow-through hydrothermal reactors One or two step acid hydrolysis Dilute acid pretreatment + enzymatic hydrolysis Five 10 m 3 bio-reactors Enzymatic hydrolysis Fermentation Cultivation GMM certified Flexible Process configurations Forest and agro feedstocks Biorefinery applications (sugar platform) Capacity, 2 tons of dry wood chips / 24 h

35 Layout 1. Raw material intake 2. Feeding vessel 3. Steaming and impregnation 4. Pretreatment 5. Neutralisation and inhibitor control 6. Enzymatic hydrolysis and fermentation 7. Yeast propagation 8. Distillation 9. Product tank 10. Filter press 11. Solid material to incineration 12. Liquid to incineration/ biogas production 13. Evaporation Equipment

36 Hydrothermal Pre-treatment of Lignocellulose Feedstock Feed stock wood chips screw-s impregnation tank horizontal reactor steam screw-s 1 H 2 SO 4 steam screw-s vertical reactor filtrate sample position slurry tank

37 Earlier experiences (not targeting high yield of furans) Wheat straw Mild pretreatment; ~2-6 g/l furfural, ~0-1 g/l HMF. Harsh preteratment >10g/l Spruce chips Mild - medium pretreatment; ~2g/l furfural, ~3 g/l HMF Pine chips Medium harsh pretreatment; ~4 g/l furfural, ~8-10 g/l HMF.

38 Process Sawdust and Wheat Straw Fermentation & distillation Ethanol Pretreatment & fractionation less hydrolysed Cellulose Enzymatic treatment Sugars Chemical Processes HMF Furfuryl alcohol Dimethylfuran (fuel) Ligno-cellulosic Biomass (sawdust) Sugars and furans Fractionation Chemical Processes Furfural Furfuryl alcohol FA/Furfural-mix C5 & C6 (oligo- & polysacharides) Lignin-rich solid residue Or further hydrolysis to furans Pellet processsing Energy

39 Discussion Understanding of the different streams. Contents, Assays, purity, analytical methods and control. Control of hydrolysis and extraction of Furans (Pilot/Demo plant) How to process the different streams before chemical processing if needed. Filtration, extraction, other methods Defining Target furans of value based on the different streams and demand. No industrial process available for HMF from lignocellulose

40 Separation Development Feed stream: Sawdust hydrolysate containing furans, excluding lignin (from Örnsköldsvik). Membrane filtration to separate furans from hydrolysate Laboratory tests either at SPPD or at Alfa Laval Pilot scale tests at Örnsköldsvik Purified streams used for downstream chemistry Extraction to separate furans from hydrolysate Investigate downstream separation of product streams (when applicable)

41 Reason for using filtration technology Less chemicals in aqueous streams Greater ease of disposal Less need for additional chemical adidtional for clean up Typically a TMP mill will release approx 3-5kg carbohydrates per m3 of water This means approx kg of carbohydrates per hour Potentially 3500 tonnes per annum lost

42 Potential of processing

43 Concept of process

44 Plant design

45 Microwave applications Lab scale Up to 10 ml Pilot scale Potential up to 0.6 m 3

46 Glucose/Fructose to HMF and downstream H 3 C O OH OH OH O O HO OH Fructose HMF From Cellulose H 3 C O OH OH OH O O HO OH Fructose HMF Fructose is more reactive and selective to make HMF than glucose i.e. higher yield Starting from glucose likely involves isomerization to fructose before dehydration to HMF FDCA Dimethyl furan & Other Chemicals 2,5-bishydroxymethyl furan

47 Conclusions of Furu2Furan Literature review, lab based experiments, pilot scale experiments and demo plant runs carried All in a period of 9 months Additional work Environmental aspects Financial aspects Logistics Devising alternative pathways to new chemical derivatives Investigating pilot scale microwave processing Strong links built between industry partners New projects underway (OptiFuran, Furan2Market)

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