Transformation of lignocellulose into aromatic building blocks
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1 , snabrück Transformation of lignocellulose into aromatic building blocks Rainer Schweppe, Gerd Unkelbach, Ulrich Fehrenbacher Fraunhofer ICT, Pfinztal Thomas Hirth Fraunhofer IGB, Stuttgart
2 Contents 1. Introduction 2. Sugar based aromatics 3. Lignin separation and transformation 4. Summary and conclusions
3 Introduction - Potential of Lignocellulose-Feedstock's (LCF) -
4 Vision Exploration of new synthesis strategies and development of new production sites for the partial substitution of fossil to renewable resources within the middle of the 21 century.
5 Raw material Processing - Grinding - Extraction - Digestion Biotechnological Transformation Chemical Transformation Building Block Material From feedstock to product
6 Cellulose Hemicellulose Lignin Glucose Xylose ligo-phenol Hydroxymethyl- Furfural (5-HMF) Furfural Monophenol H CH 2 CH H C CH 2 H CH CH CH 2 H CH CH H H H H H
7 Ligno-Cellulosic Feedstock (LCF) Fractionation (e.g. rganosolv- Process) Cellulose ligomers a. Polymerisation Technical Lignin Hemicellulose / Polyoses Cellulose Alkaline Hydrolysis xidation Vaniline and Deriv. Vanilin and Deriv. Vanilic Acid Syringa aldehyde Reductive Hydrothermolysis Phenols and Deriv. Phenols, Benzene Resins, il Lignin Polymers and Resins for: Bonding Material Artificial Resin Resinous Exchanger Hydrolysis Acid Treatment Furfural Furan and Deriv. THF -Butanediol THF- Polyurethane Furan Resins Hydrolysis / Ferm. Ethanol and Deriv. Hydrothermolysis Polyalcohols Reductive Amination Diamins, Diisocyanates ( Polyurethanes ) Acid Treatment HMF and Derivatives Levulinic Acid (LEVA) (+ Formic Acid) LEVA-Esters Ethyl levulinate higher esters (Fuel additive, Solvents) Angelica lactones (Solvents) Poly-(α-angelica lactone)(polymers, Plasticizers) Polycarbonate Source: DW
8 Sugar based aromatics Biorefinica 2009
9 Glucose, Fructose Hydrothermolysis reductive Hydrothermolysis H H H-CH 2 CH H H H H H H Compressive strength _ _ rise for reference #1 and formulation #3 5-HMF 5-Hydroxymethylfurfural H H DHD 2,5-Dihydroxydioxan H H Mannit H H Sorbit Polyalcohols Comp. stress (kpa) % compression Reference #1 Formulation #3
10 Purification of 5-Hydroxymethylfurfural via distillation 5-HMF 5-HMF residue (raw) (purified) DBU-Vorhaben Synthesebausteine aus nachwachsenden Rohstoffen Aktenzeichen: HMF residue (raw material)
11 ICT Synthesis of 2,5-Furanedicarboxylic acid (FDCA) H H 2 Pt auf C H H xidation of 5-Hydroxymethylfurfural in water Batch size max. 2,5 kg 5-HMF Yield FDCA > 98 %
12 5-Hydroxymethylfurfural Furandicarboxylic Acid 2,5-Dihydroxymethylfurane 2,5-Diaminomethylfurane Polyesters, Polyamides, Thermoplastic Elastomers Polyesters, Polyurethanes Polyamides, Polyurethanes
13 Biopolymers based on Furanedicarboxylic acid Polyamides R R + H 2 N CH 2 x NH 2 * N N CH 2 * x n Polyesters R R + H CH 2 H x * CH 2 * x n
14 Thermal properties polyamides of glucose based polyamides N H N H * n * Tm = 250 C * N N n H H * Tm = 175 C Fibres * N N n H H * Tm = 125 C
15 Thermal properties of glucose based polyesters * n Tm = C Fibres from melt * * n Tm = 120 C * * n Tm = C * * n Tm = C
16 Glucose DHD Glykolide Polyglykolide H H H H sc. H 2 H H xid. * n * H Polyester T m ( C) Poly(3HB) 178 Poly(3HV) 110 Poly(L-lactid) 185 Poly(glycolid)
17 Lignin separation and transformation
18 Lignin 18 H 2C H 16 H 2C H C HC CH H 2C H HC H H 2CH 1 H 2C H 3 C HC CH H CH 2C H 2 15 H 3C CH 3 H 2C H HC CH 3 HC CH CH HC 1/2 1/2 CH 3 HC 4 HC H 2C H CH 3 H 3C H 2C H H HC HC H CH (CH 3) 1/2 HC C H 2C H CH 3 HC H HC 10 H 3C HC H C CH 2 5 HC CH CH H 2C H CH H 2C H HC HC H HC H 2C CH CH H 3C HC (C 6H 10 5) nh HC CH 11 HC 12 CH 3 CH 3 HC 6 CH2 H H 2C H 13a H 3C 14a CH 7 H 2C H CH 3 H HC H HC 8 HC H 3C H CH 3
19 Lignin release from wood Sulfate or sulfite process Acid wood digestion Ionic liquids Hydrothermal Treatment (Aquasolv-Process) rganosolv-process (Ethanol, ) Enzymatic cleavage (+ Fraunhofer IGB)
20 Lignin production: The RGANSLV-Process Temperature: C Exraction time: 1 hour Solvens: Ethanol/Water Separation Solvent Regeneration Autoclave (13 L) Beech wood
21 Nanosized rganosolv-lignin
22 Lignin Transformation: Hydrothermolysis Process parameter max. temperature: 400 C max. pressure: 250 bar max. flow rate: 7,3 L/h Reactor length: 8-12 m Reactor diameter: 9 mm Residence time: 15 min
23 Chemical composition of the products Fraction of oligomers Fraction of monomers CH 3 H CH 3 H CH 3 H 3C H CH 3 H H CH 3 CH 3 CH e e e+07 1e H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H H CH3 H CH 3 H CH 3 CH 3 H CH 3 CH 3 H H H H 3C CH 3 H 3C H H 3 C CH 3 H H 3C H H H CH 3 CH H H H H Abundance Mass selective detector H H = ISTD Flam ionization detector Time [min]
24 Poplar lignin phenol guajacol & monomethoxyphenols syringol & dimethoxyphenols o-hydroxyphenol derivatives m-hydroxyphenol derivatives benzene; 1,2,3- triol derivatives alkylphenols di.- and trimethoxy-alkylbenzenes; alkylbenzenes unknown compounds Beech wood lignin il composition after hydrothermal treatment
25 Lignin in composites
26 Summary and conclusions Biorefinica 2009
27 Cellulose, Hemicellulose und Lignin are already used in industrial scales Increasing use of Lignocellulose is detectable There exist several ways for the production of lignocellulosic products. Lignin based products could partially substitute fossil resources. Technical feasibility studies are still running. High grade of functionality needs special conversion technologies.
28 Acknowledgment: Deutsche Bundesstiftung Umwelt (DBU) Fachagentur Nachwachsende Rohstoffe (FNR) Thank you for your attention!
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