Woody Biomass Conversion: Process Improvements at ESF

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1 Woody Biomass Conversion: Process Improvements at ESF Shijie Liu Biorefinery Research Institute Department of Paper and Bioprocess Engineering SUNY College of Environmental Science and Forestry

2 Outline Introduction Hot-Water Extraction Wood Extract Hydrolysis Membrane Separation Fermentation Conclusion

3 Woody Biomass 21% hardwoods 25% softwoods Chemical components of wood wood Lignin extractives 2-8% carbohydrates 35% hardwoods 25% softwoods hemicellulose cellulose 45%

4 Incremental Deconstruction Maximize value achievable Minimize energy loss Minimize waste byproducts generation Multiple product mix

5 Wood Components: Inorganic Components K & Ca (400 ~ 1000 ppm); Mg & P (100 ~ 400 ppm) ; and 70 others Extractives Aliphatic and alicyclic: Terpenes; terpenoids; esters; fatty acids; alcohols; Phenolic: phenols; stilbenes; lignans; isoflavones; Others: sugars; cyclitols; tropolones; amino acids, Hemicellulose Lignin Cellulose

6 Lignin Three precursors a. trans-coniferyl b. trans-sinapyl c. trans-p-coumaryl alcohol alcohol alcohol Guaiacyl Syringyl p-hydroxyphenyl

7 Hemicellulose Common among angiosperm woody biomass:

8 Hemicellulose Type Soft wood Hard wood 1 5 ~ 8% ~15% ~ ~ 10% Trace 5 Trace 15~30%

9 Cellulose

10 Woody Biomass Hot-Water Extraction Residual Woody biomass Co-Gen or CHP Gasification Feedstock Extraction Liquor Unbleached Pulp Alkaline Puling Pulping Chemicals Fuel Pellets Reconstituted Wood Products Electricity and Steam Methanol Acetic Acid Hydrolysis / Separation Food additives: sugar oligomers Sugars Bleached Pulp Paper products or Cellulose products Black Liquor Carbohydrates Separation or Co-Gen Aromatics Plastics Adhesives Solvent Surface agents Xylitol Ethanol Butanol Acetone Hydrogen Lactic Acid PHA

11 Hot-Water Extraction

12 Maple Wood Extract Acetic Acid, Methanol Acetyl, Polysaccharides Aromatics, Furfurals Monomeric Sugars Concentration, mm Methanol, mm time, min Acetyl Aromatics Furfurals Starting conditions: g OD Maple Woodchips g water, 28 C HAc MeOH Sugars time, min Acetic Acid, mm

13 Autocatalytic Extraction Dissolution of acetyl groups produces Acetic acid (HAc) Acetic acid ionizes in Water HAc H + + Ac Acidity or proton catalyzes extraction L-OX n + H + == L-OX n H + L-OX n H + + H 2 O == L-OH + X n OH H + X n OH H + == X n OH + H + - Ka = + [H ][Ac [HAc] ]

14 ph in Extract liquor (10,50) (5,50) (5,100) (5,200) ph (10,1000) (5,1000) (C +0, C HOAc ) T, C

15 Mass Balance Glucan: g Xylan: g Mannan: 2.13 g Galactan: 0.80 g Arabinan: 0.58 g Rhamnan: 0.42 g Acetyl: 2.17 g Woodchips: 100 g Klason Lignin: g Acid Soluble Lignin: 2.94 g Unidentified: g = Glucose: g = Xylose: g = Mannose: 2.37 g = Galactose: 0.89 g = Arabinose: 0.66 g = Rhamnose: 0.47 g = Acetic acid: 3.57 g Hot-Water Extraction at 160 C for 2 hours with Water to Solid ratio of 4:1 Residual Woodchips: g Glucan: g Xylan: 4.14 g Mannan: 1.10 g Galactan: 0.92 g Arabinan: 0.04 g Rhamnan: 0.12 g Acetyl: 0.89 g Klason Lignin: 20.0 g Acid Soluble Lignin: 0.89 g Unidentified: g Extract: g Glucan: 0.88 g Xylan: 8.94 g Mannan: 0.94 g Galactan: 1.31 g Arabinan: 0.55 g Rhamnan: 0.82 g Acetyl: 1.07 g = Glucose: g = Xylose: 4.70 g = Mannose: 1.22 g = Galactose: 1.02 g = Arabinose: 0.04 g = Rhamnose: 0.14 g = Acetic acid: 1.46 g = Glucose: 0.98 g = Xylose: g = Mannose: 1.04 g = Galactose: 1.46 g = Arabinose: 0.62 g = Rhamnose: 0.92 g = Acetic acid: 1.76 g Degredated Lignin: 3.27 g Unidentified: 5.22 g

16 ESF Biorefinery: Hot-Water Extraction Hydrolysis Fractionation Acetic Acid Methanol Reducing Sugars Aromatics, Furfurals Xylan Fermentation to Ethanol, Plastics,

17 Theoretical Considerations: 200 DP of the Extractable Polymers k E = k H DP in extract liquor DP in solid phase Time

18 Hydrolysis Extract or Dissolved woody biomass solution Dissolved carbohydrates and lignin in liquid Monomeric sugars (~1/3) and polysaccharides Hydrolyzate Monomeric sugars (> 80% of all carbohydrates) Hydrolysis

19 Hydrolysis Depolymerize macromolecules (of carbohydrates) by inserting water molecules between the monomeric units Enzymatic hydrolysis Using a hydrolytic enzyme as catalyst Acid Hydrolysis Using acid (proton) as catalyst

20 Enzymatic Hydrolysis Substrate specific Cellulase, xylanase, Endo, exo, Inhibition Acid phenolics

21 Enzymatic Hydrolysis ph = No ph adjustment Reducing Sugar Concentration, g/l Hydrolysis Time, Days B C D

22 Enzymatic Hydrolysis ph = 5.5 Reducing Sugar Concentration, g/l Hydrolysis Time, Days B C D

23 Acid Hydrolysis Glycosidic bonds Proton is the active catalyst No preference on first, second, or any bond Dehydration Undesirable dehydration reactions with monomeric sugars as initial reactants Acid recover / reuse

24 Acid Hydrolysis Dehydration reaction Reaction Rate Hydrolysis Reaction [H + ]

25 Acid Hydrolysis Dilute acid Lower ph, but not high concentration HCl, H 2 SO 4, HNO 3, Furfural, HMF and further dehydration products Lignin / aromatics - deposition

26 Acid Hydrolysis: 95 C Xylose Concentration, g/l % H 2 SO 4 1.5% H 2 SO 4 3.0% H 2 SO 4 6.0% H 2 SO Time at temperature, minutes

27 Acid Hydrolysis: 105 C Free Acetic Acid Concentration, g/l % H 2 SO 4 1.5% H 2 SO 4 3.0% H 2 SO 4 6.0% H 2 SO Time at temperature, minutes

28 Hydrolysis: 105 C % H 2 SO 4 Precipitates, g/l % H 2 SO 4 3.0% H 2 SO 4 6.0% H 2 SO Time at temperature, minutes

29 Fractionation Solid-liquid separations Aromatics and/or degraded lignin recovery Xylan or xylo-oligomer recovery Catalyst recovery Liquid-liquid separations Membrane separations for Sugar stream purification Recovery of chemicals

30 Nano-Filtration Membrane System

31 Experimental Set-up: Membrane Separation

32 Schematic Diagram P Permeate Holding Tank Feed and Concentrate Tank

33 Samples of fractionation

34 Membrane Separation Resistances: Osmotic Pressure Friction Porous Solids Model: μ U Δp = π + U 1+ k a + U 2 2 bu

35 Osmotic pressure Osmotic Pressure, psi Apple Juice Orange Juice Glucose Sucrose Solids, %

36 Flux versus Pressure 500 Permeate Rate, ml/min Pressure, PSI

37 First pass: Permeate Rate, ml/min V 0 = 66L V f = 28L [HAc] 0 : 4.62 g/l [HAc] f : 5.19 g/l P = 150 psi V 0 /V

38 Second pass: Permeate Rate, ml/min V 0 = 66 L V f = 28 L [HAc] 0 : 2.20 g/l [HAc] f : 3.3 g/l P = 150 psi V 0 /V

39 Third Pass: Permeate Rate, ml/min V 0 = 66 L V f = L [HAc] 0 : 1.40 g/l [HAc] f : 2.64 g/l P = 150 psi V 0 /V

40 Osmotic Pressure Change π, psi V 0 /V

41 Fractionation of wood extracts Time, minutes C, g/l 10 5 Concentrate Stream Permeate Stream C, g/l Time, Minutes

42 Reducing sugars as xylose: Starting point First pass g/l Second pass 18.2 g/l Third pass 16.0 g/l Reducing Sugars, g/l V 0 /V

43 Acetyl Free Acetic Acid Bond Acetyl, as acetic acid C, g/l V 0 /V

44 Acetic acid concentrations C, mol/l Concentrate Stream Permeate Stream Time, minutes

45 Minors C, g/l Methanol HMF Furfural Formic Acid V 0 /V

46 Separation Efficiency Xylose 0.95 R s 0.90 Aromatic Compounds Time, minutes

47 Separation Efficiency Acetate Methanol Furfural HMF R s Time, minutes

48 Fermentation Ethanol E. Coli Pichia Stipitis Butanol Clostridium acetobutylicum PHA

49 Conclusions Wood Extracts contain more oligmers than monomeric sugars Acid hydrolysis is currently preferred NF-Membrane can be employed to purify sugar stream; Osmotic pressure plays an important role;

50 Acknowledgements Thomas E. Amidon Christopher D. Wood Raymond Appleby Zhijie (Jeff) Sun Jennifer Putnam Alan Shupe Tingjun Liu Dave Kiemle Kathryn Gratien Mitchell Graves Ruofei Hu Yang Wang

51 Thanks!

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