Hydroconversion catalytique de la lignine en aromatiques Lignin to aromatics by catalytic hydroconversion
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1 Lignin to Aromatics Hydroconversion catalytique de la lignine en aromatiques Lignin to aromatics by catalytic hydroconversion Partenaire 1: IRCELYN (D. Laurenti, C. Geantet, P. Fongarland (LGPC)) Partenaire 2: LAGEP (E. Gagnière, I. Pitault, M. Tayakout) Partenaire 3: Total Feluy (K. Hortmann) Partenaire 4: LGPM (F. Puel) Démarrage Nov Fin Mars 2019
2 Scientific program Task 1: Selection lignin & characterization IRCELYN Task 2: Solubility of selected lignins Dissolution kinetic rate LAGEP/LGPM Task 3: Screening of catalytic systems in batch reactor IRCELYN Partenaire 1: IRCELYN (ThanSon Nguyen, Junjie Pu, Sébastien Andry) Partenaire 2: LAGEP (Aurélie Galfré) Partenaire 3: Total Feluy Partenaire 4: LGPM Task 4: Physical and chemical modeling of the process LAGEP/IRCELYN Task 5: Catalyst testing in a semi-opened batch reactor IRCELYN/LAGEP Task 6: Technicoeconomical evaluation of the process TTAL
3 Lignin as starting biomass 5-5 H Me Me H H H Me - Me Pinoresinol substructure - H --4 H H H Me H H H H H H Me -5 Dibenzodioxocine -1 An abundant bio-resource A natural precursor for aromatics (phenols, BTX) A co-product in pulp industry and biorefinery A complex hydrophobic macro-structure H H Me 4--5 Me Valorization Depolymerization Characterization
4 Conversion of lignin e 5-5 H Me H H H Me - Me H --4 H H H -1 H Me H H H H H Pressure (MPa) Lignin Me -5 H H Me 4--5 Me Hydrothermal processing water Hydrotreatment Hydroconversion Solvolysis org. solvent H 2, catalyst Catalytic Cracking catalyst, no solvent Pyrolysis no catalyst, no solvent Fuels Chemicals (Phenolic compounds or BTX) Temperature C Thermochemical conversion with heterogeneous catalyst B. Joffres et al. il & Gas Sc. Tech. 68, 4 (2013) B. Joffres et al. Appl. Catal. B: Environmental, 145 (2014) B. Joffres et al. Appl. Catal. B: Environmental 184 (2016)
5 Catalytic hydroconversion of lignin Reactor upgrading H2 Reflux Analyse m-gc Classic batch with opened H2 ballast (B. Joffres PhD 2013) Condenseurs T= 350 C Ptotale=80 b Batch semi-ouvert Réacteur autoclave - pen on gas phase with m-gc analysis on line - Equiped with a reflux at 170 C : recycling of solvant, removing lights products and water from mixture 5
6 Wheat straw soda Lignin Normalised, a.u Masse molaire (g/mol eq PS) GPC molar mass distribution Lignin P1000 -PF Lignin P1000 -PF ace Protobind 1000 Thermogravimetric analysis (TGA) Elemental analysis/tga Analyse élémentaire (CHNS) Composition (% pds) C 61,8 H 5,6 29,5 N 0,7 S 0,9 H/C 1.09 /C 0.36 ATG sous air cendres 4,2 eau 2,2 31 P NMR after phosphytilation RMN 31 P Groupement H aliphatiques 1,11 H syringyles + unités condensées 1,59 H guaiacyles 0,96 H p-hydroxyphényles 0,41 mmol/g lignine H acides carboxyliques 0,71 4,2% pds
7 Products recovery protocol Mélange (L) au séparateur Liquide Décantation Phase aqueuse Phase organique Mélange (L+S) au réacteur Mélange (L) au séparateur 30 g de lignine 70 g de tétraline 3 g de catalyseur Gaz Conditions: P = 80 bars D H2 = 40 NL/h; T Réacteur = 350 C; T Reflux = 160 C; N = 800 rpm 7
8 Products recovery protocol Reacted mixture Gases Centrifugation Mélange (L+S) au réacteur Mélange (L) au séparateur Soxhlet THF 30 g de lignine 70 g de tétraline Solid 3 g de catalyseur THF insolubles Solid Gaz Extract Liquids Conditions: P = 80 bars D H2 = 40 NL/h; Liquid in tetralin Heptane precipitation T Réacteur = 350 C; THF T Reflux = 160 C; solubles N = 800 rpm Filtration Liquid in tetralin Solids Lignin residue 8
9 Screening of catalysts 1,2 1 0,8 0,6 0,4 0,2 characterization characterization 0 Liquid Gas Lignin residue Solids Semi-batch (volume du réacteur 300 ml) Conditions: 350 C, P tot = 80 bar, 800 rpm, t= 5h, débit H2: 50 Nl/h
10 H2 consumption (mmol/g lignin) Conversion and products distribution Yield (wt%) CoMoS/Al203 (350 C, 80 bar, DH2:40NL/h) Reaction Time (h) Ash in initial biomass Conversion (%) Liquid is the main product Solid reached initial ash content Conversion Liquid Lignin residue Gas Solid H2 consumption increased with conversion
11 Yield (wt %) Evolution of gases 12 CH4 C C2 Light alkanes (C2-C6) Reaction Time (h) Main gas: C2 decarboxylation) and CH4 (methanation, demethylation) Analysis on line shows Reproducibility Gas are formed mainly before 5h
12 Lignin residue summary 20 % remain after 13h residence time Dehydroxylation/decarboxylation : deoxygenation /C Depolymerization MW Can this residue be further converted into liquid? Pd Lignin P h 1 h 5 h 13 h %wt by CHNS 29,2 23,7 20,7 11,4 9,5 % H by 31 P NMR 9,8 7,3 8,2 6,5 4,7 ther type of H (%) ether, carbonyle, furan 19,4 16,5 12,5 4,9 4,8
13 Characterization of liquid Yield of liquid increased continuously in function of residence time In separator liquid increased especially organic Molecular masses decreased slightly GPC CMPSITIN? 13
14 Characterization of liquid : GCxGC-MS, -FID GCxGC-MS: identification GCxGC-FID: quantification with internal standard Vue 3D d une huile de lignine analysée en GCxGC Liquid in batch reactor Solvent Alkanes Phenols Aromatics & Naphthenes
15 Characterization of liquid : GCxGC-MS, -FID Liquid + tetralin Phenols are major components Alkanes and aromatics continuously increased in the separator while methoxy phenols are converted Quantification (ECN method with internal standard)
16 Characterization of liquid : GCxGC-MS, -FID Solvent 3D view : Liquid in separator phenols Aromatics & Naphthenes
17 Characterization of liquid : GCxGC-MS, -FID Naphthenes, phenols and aromatics continuously increased in the separator Quantification (ECN method with internal standard)
18 Conclusion Screening of catalysts in catalytic hydroconversion of wheat straw soda lignin Develoment of analytical tools to evaluate catalyst effect (conversion/selectivity) Establishment of kinetic model thanks several experiments with different residence time with a chosen catalyst (CoMoS/Al23) Further work. ther type of lignin will be converted (kraft, lignocellosic ethanol biorefinery..) Comparison sulfide/oxide/reduced catalyst Solubility of lignin/dissolution kinetics Technico-economical analysis of the process
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