WP No.4: Innovative chemical conversion and synthesis - Highlights

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1 WP No.4: Innovative chemical conversion and synthesis - Highlights E. Papadopoulou, P. Schöenicke, B. Kamm, J. Rogut, G. Marcotullio, D. van Es, E., R. Gosselink, H. Hagen, H. Reith, B. Estrine Development of multi-product lignocellulose biorefinery technology - Results of the Integrated Project BIOSYNERGY - 17 November 2010, REIMS, FR

2 Content 1. Partners and WP Objectives 2. WP tasks 3. Highlights 4. Conclusions

3 Partners involved ECN: Energy research Center of the Netherlands (Project Coordinator) Cepsa: Compania Espanola de Petrolos, S.A. (Conventional Refinery) Dow Benelux (Bio-Polymer) Aston University (Lignin Upgrading) A&F: WUR Agrotechnology and Food Innovations B.V. (Lignin, Building Blocks and Bio-Polymers) ARD: Agro Industrie Recherches et Développements (WP Leader, Bio-Surfactants) Bioref: Biorefinery.de GmbH (Building Blocks) GIG: Glowny Instytut Gornictwa (Separation technologies) JRC: Joint Research Center (Economic assessments) Chimar Hellas S.A. (Bio-Polymer and Materials) TUD: Delft University of Technology (Building Blocks) IFP: Institut Français du Pétrole (Conventional Refinery) Greencell S.A. (Biomass feedstocks from Biorefineries)

4 WP4 RTDA partners providing data for WP5&6

5 Objectives WP 4 Definition and technical development of reaction chemistries and process designs for a well-defined portfolio of value added products Validation of commercial opportunities for the products portfolio in existing and also new industrial and consumer markets and applications For pentoses (C5 sugars): production of pentosides surfactants by a green technology in order to access the price level of petrol based competitors in the market (1,5 /kg)

6 Tasks and Subtasks 4.1 Platform chemicals (production and ) characterization => Lignin depolymerisation (A&F) & HMF (Bioref) + Furfural (TUD) production 4.2 Products from platform chemicals (reaction and process design)=> FDCA production from HMF, succinic acid production: : (A&F + Bioref) 4.3 Polymer synthesis,, polymer processing and materials from FDCA and lignin streams (derivates) materials (A&F + CHIMAR + DOW) 4.4 Applications testing and market validations (A&F + CHIMAR + DOW) 4.5 Pentoses (C5-sugars) valorization as raw materials for surfactants (ARD) 4.6 Application of innovative membrane reactor concepts for product recovery (GIG) 4.8 Review of data generated by the different project partners as input for both the conceptual design of the ABNT demo-plant (WP5) and the integral chain analysis and optimization activities (WP6) (All) 4.9 Review and assessment of progress towards the specific project objectives (All)

7 Product lines in the IP BIOSYNERGY Multi-product biorefinery, Focus on residues cellulose ethanol i.e. C5 and lignin valorisation Lignocellulosic biomass Esp. STRAW Physical chemical pretreatment & Fractionation Cellulose Hemicellulose Enzymatic Hydrolysis C6 sugars C5 sugars Fermentation Chemical Conversion Ethanol ABE Xylonic acid (HMF) > 2,5 FDCA Furfural Pentoside Surfactants Lignin SC Depolymerisation Catalytic Pyrolysis Chemical conversion Enzymatic conversion Fractionation Phenolics Activated lignins Resins / Thermosets B i o m a s s r e s i d u e s CHP Heat & Power to process

8 3. Highlights: Production of Furfural from pentoses streams (TUD)

9 Deeper understanding of the chemistry of furfural formation from D-Xylose in dilute aqueous acidic solutions (Marcotullio G. and de Jong W., 2010, Green Chem. 12, 1739) The Cl - ions favor the formation of (2) from D-Xylose (X). Halides nucleophilic character also enhance furfural formation (article in preparation). Up to 95% selectivity (from actual 75%) and 88% furfural yield (from actual 55%) could be achieve using the right mix of acid and metal halides in aqueous solutions. February 8,

10 Process for the production of furfural from pentoses based on vapor recompression Furfural PreReac PreHeat 2 React Col 3 6 Comp 4 W February 8, 2011 Pentoses containing feed Energy costs reduction 85-95%! Purification from Organic Carbon 10 ReB Acid confined section Dilute Furfural (<8wt%) Patent Pending

11 Distillation of diluted furfural also using vapor recompression This scheme can be applied to existing installations achieving significant energy savings! Comp Hrec StripCol Dec 15 ReB February 8, 2011 Dilute Furfural (<8wt%) Concentrated Furfural (95%) Patent Pending

12 3. Highlights: 4.1: Furfural production (TUD) New insides in furfural formation chemistry has been investigated regarding the influence of Chloride salts on the conversion of Xylose into furfural. Total yields as high as 85% on the theoretical have been achieved in some conditions and a paper has been published in Green Chem. journal. Based on these results work a novel process for economically sound and low energy intensive production of furfural has been designed (patent).

13 3. Highlights: Production of HMF from cellulose (Bioref.)

14 3. Highlights: 4.1: HMF production (Bioref) Cellulose isomerization, cat. cat. -3 glucose fructose 5-Hydroxymethylfurfural Focus on production of HMF from cellulose and glucose Target: Design of a simplified process allowing an efficient recovery of HMF 1) Sugars conversion > 98%, selectivity ranging 80-94% 2) Improvement made on the process simplification compared to literature data

15 3. Highlights: Lignin depolymerisation (A&F)

16 3. Highlights: 4.1: Lignin depolymerization (A&F) Lab-scale supercritical depolymerisation of selected lignins to monomeric phenolics In-depth characterization of feed and (intermediate) products Production of phenolic mixtures in lab-scale quantities

17 3. Highlights: Task 4.1: Lignin depolymerization 100 ml stirred PARR reactor (300 C, bar) CO2 feeding Product removal Lignin feeding Heater/reactor

18 3. Highlights: 4.1: Lignin depolymerization (A&F) Organosolv lignin is converted in (based on dry feedstock): wt% phenolic oil 5-10 wt% identified phenolics wt% water wt% char 10 wt% permanent gases (CH4, C2H4, CO, Aceton ) 1) Mass balance complete 2) Phenolic oil consists of oligomeric + monomers phenolics This lignin fraction can be used for eg. development of biobased resin for wood panels 3) Apply sc process for BIOSYNERGY lignin streams (in progress)

19 3. Highlights: Task 4.2: Added value chemicals from Platform chemicals: A&F-Bioref.: FDCA synthesis from HMF HO O O HO O O HMFu O FDCA HO Efficient processes designed - Quantitative yields obtained - Economics of the processes realized through WP5/6 Developments of FDCA uses as co-catalyst for acidic equilibrated reaction (joint publication A&F/ARD in preparation)

20 3. Highlights: Task 4.2: Added value chemicals from Platform chemicals: A&F: Succinic acid from biomass (A&F)

21 3. Highlights Novel thermo-chemical procedure for preparation of succinic acid from biomass From Levulinic acid; also possible from HMF, and even Cellulose Patent application filed Co-production of oxalic acid possible Approx. 50% isolated yield succinic acid Approx. 20 times higher space time yield then best practice fermentation

22 3. Highlights: Task : Polymers synthesis and applications: A&F: FDCA polymerization Furan based polymers A&F

23 3. Highlights From lignocellulose to performance polymers (polyesters) Conversion of cellulose to HMF Conversion of HMF to resin grade FDCA (>99.9% purity) Polymerisation of FDCA

24 3. Progress/Results towards the objectives Lab scale polymerisation ( g scale) 24

25 3. Progress/Results towards the objectives All polymers are colorless powders or transparent fibers after precipitation (medium MW materials; Mn 10-17,000) PBF (crude) PEF PPF

26 3. Highlights: major results Task : Polymers synthesis and applications: CHIMAR: Materials synthesis from lignin products and surfactants (from WP1-4)

27 In BIOSYNERGY project Chimar Hellas tested: A variety of samples as substitutes of phenol in resol PF resins: Phenolic fraction from wood pyrolysis liquid and the organic phase of DDGS pyrolysis oil - provided by BTG. Phenolic fraction from wood pyrolysis liquid of BTG treated with O 2 and O 2 +Laccase The treatment carried out by VTT. Phenolic fraction from lignin pyrolysis - provided by ECN. Lignin from straw derived by the organosolve and alkaline process - provided by ARD and the WUR-FBR accordingly. Lignin from ARD organosolve process treated with N 2, O 2 and O 2 +Laccase - The treatment carried out by VTT. Corn stover stillage provided by ABNT. Surfactants from C5 sugars as additives in wetting agents for paper impregnation in the wood-based panels industry.

28 Highlights - Alkyl xylosides by ARD proved effective surfactants in UF syrups used for paper impregnation in the wood-based panels industry. WA WA The phenolic fraction from BTG is a substantial phenol substitute, at least up to a 25% phenol replacement, that may be used for the synthesis of phenol-formaldehyde resins. - Lignin samples from ARD gave very promising results as phenol substitutes, at various levels up to 50%, when used in the synthesis of phenol-formaldehyde resins WA Chimar & C5 pentoside Chimar Foam heigh after 3 min (mm) WA 0397 WA Chimar & Radia 6505 WA1703 Chimar

29 3. Highlights: major results Task 4.5: Surfactants ARD Two original processes designed for production of alkyl polypentosides from various C5 streams

30 3. Highlights: major results Techno 1: Pentoses to surfactants: Unpurified Pentoses solutions from organosolv treatments or steam explosion of wheat straw have been converted in short tail surfactants (C4 and C5) with good results. Significant cost savings Confirmation of market potential of Xylosides in Wetting agent formulation for Paper impregnation on Wood panel industry Development of the technology at pilot scale One paper in preparation 100,0 90,0 80,0 70,0 % Yields 60,0 50,0 40,0 30,0 20,0 10,0 0,0 Xylose syrup AVIDEL syrup ABNT PWS Syrup Butyl Pentosides Isoamyl Pentosides Decyl Pentosides Production pentoside surfactants from C5 hydrolyzates at kg scale (ARD)

31 3. Highlights: major results Techno 2: Biomass to surfactant Technology developed on model raw materials Applications: Wheat Straw directly converted into Surfactant with high yields! H 2 SO 4 (cat.) / H 2 O (cat.) n-decanol / / t Two papers published in 2010 Carbohydr. Res; Green Chem. One submited to Tet. Let. HO HO HO HO O OH O O O HO HO O HO MeO O HOOC OH O HO O HO OH O O HOO H 2 SO 4 (cat.) / H 2 O (cat.) / t O OH + OH O HO O O O O OH HO OH n 8 OH OH O HO OH O OH

32 4. Conclusion Overall, WP4 objectives has been reached: - Significant contribution on the valorization of biomass into various green chemicals with high market potentials - Contribution to economic assessments in WP5/6 for choosing best scenarios for a multi-products lignocellulosic biorefinery.

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