Characterization studies of Waste- bio-derived feedstocks

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1 CENTRE FOR RESEARCH AND ΤECHNOLOGY-HELLAS CHEMICAL PROCESS ENGINEERING RESEARCH INSTITUTE Characterization studies of Waste- bio-derived feedstocks C. Michailof, E.F. Iliopoulou,K. Kalogiannis, M. Pachnos, M. Emmanouilidou and A.A. Lappas

2 PROJECT : WAVES - WAste bio-feedstocks hydro-valorisation processes PROJECT SCOPE Exploring established and new emerging heterogeneous catalytic technologies for the production of aviation and road transportation fuels (i.e., gasoline, kerosene, diesel) via hydroprocessing (hydro-isomerization, hydrocracking or hydrodeoxygenation) of renewable feeds. CPERI s Contribution Development of new and selective catalytic systems for diesel or aviation fuel production via hydroconversion of waste bio-feedstocks: Bio-oil Algea oil Vegetable oils F-T waxes Fundamental Prerequisite Detailed analysis of the feedstock

3 Bio-Oil (Pyrolysis oil) Biomass Pyrolysis Thermal decomposition of biomass T>500 o C Bio-oil (liquid product) Char (solid product) Gases Bio-oil carboxylic acids aromatic hydrocarbons aldehydes & ketones phenols, guaiacols, syringols sugars Complex mixture, different classes of compounds Requires analytical techniques with increased separation and resolution

4 Bio-Oils studied Selected biomasses for Thermal (non-catalytic) pyrolysis Pine Cardoon Olive Kernel Jatropha Miscanthus Elemental analysis (%) Ash Extractives Lignin Cellulose Hemicellulose C H O (%) (%) (%) (%) (%) Pine 45,54 6,37 47,79 0,30 1,33 29,40 40,46 23,72 Cardoon 38,11 5,27 41,20 15,42 3,22 34,94 34,01 28,02 Olive kernel 51,97 7,80 37,83 2,40 3,07 25,10 38,75 29,05 Jatropha 46,39 6,04 42,48 5,09 9,74 43,98 22,63 28,30 Miscanthus 45,55 6,00 45,88 2,57 2,25 28,21 39,68 27,29

5 Two dimensional Gas Chromatography coupled with Time-of-Flight Mass Spectrometry

6 Two dimensional Gas Chromatography coupled with Time-of-Flight Mass Spectrometry GC x GC =? The separation (boiling point) achieved in the first column is preserved & additional separation (polarity) in the second column is accomplished Advantages of GC x GC -ToFMS Improved Chromatographic Resolution Increased Peak Capacity Enhanced Signal to Noise More Effective Automated Qualitative and Quantitative Data Processing More Information per Analyzed Sample Separation and identification of more than 500 peaks per sample Mapping of the samples for an initial estimation of its composition

7 Chromatographic analysis of bio-oils by GCxGC - ToFMS Qualitative analysis - Identification of compounds based on NIST05 library Quantitative analysis employing Internal Standard methodology using a standard solution of 53 compounds Internal standard: phenol-d 6 Standard solutions at 5 concentration levels, each solution analysed at least 5 times Determination of the RRF (Relative Response Factor) for each compound C RRF A ANOVA and WLSLR (Weighted Least Square Linear Regression) for statistical analysis and validation of the calibration Regular verification of the calibration curves is is A C i i

8 Chromatographic analysis of bio-oils by GCxGC - ToFMS Pine bio-oil Compound % w/w Group Total %w/w Acetic acid 3,55 2(5H)-Furanone 1,98 AR 0,04 Phenol, 2-methoxy- 1,45 ALI 0,10 1,2-Benzenediol 1,39 PH 8,63 3-Furaldehyde 0,97 FUR 0,85 2-Cyclopenten-1-one, 2-hydroxy- 0,60 AC 3,55 2-Cyclopenten-1-one 0,55 EST <0,01 Furan, tetrahydro-2,5-dimethoxy- 0,45 AL <0,01 Phenol, 2-methoxy-4-methyl- 0,45 ETH 0,89 Phenol, 3-methyl- 0,41 ALD 1,63 1,2-Benzenediol, 4-methyl- 0,33 KET 5,33 2-Methoxy-4-vinylphenol 0,29 PAH <0,01 Vanillin 0,26 Eugenol 0,24 4-Ethylcatechol 0,23 Phenol, 3-methyl- 0,23 Phenol, 4-ethyl-2-methoxy- 0,23 2-Cyclopenten-1-one, 2-hydroxy-3-methyl- 0,22 Phenol, 2,5-dimethyl- 0,21 Hydroquinone 0,21 Phenol, 2-methoxy-4-(1-propenyl)- 0,20 Including the H 2 O content, 60,3% of the bio-oil is characterized Rich in phenols and carbonyl compounds High sugars content Total Top 20 compounds (wt.%) 14,45 Determined wt.% of total bio-oil 21,04 Determined wt.% of organic phase 34,66

9 Chromatographic analysis of bio-oils by GCxGC - ToFMS Olive kernel bio-oil Including the H 2 O content, 46.5% of the bio-oil is characterized Hydrocarbons are detected, both aliphatic and aromatic Increased phenolic content Compound % w/w Group Total %w/w Acetic acid 4,72 1,2-Benzenediol 0,83 AR 0,32 Phenol, 2-methoxy- 0,35 ALI 0,73 1,2-Benzenediol, 3-methoxy- 0,30 PH 5,04 Phenol, 2,6-dimethoxy- 0,28 FUR 0,29 Phenol 0,27 AC 4,72 Phenol, 3-methyl- 0,22 EST 0,12 Hydroquinone 0,19 AL <0,01 4-Ethylcatechol 0,19 ETH <0,01 Phenol, 3-ethyl- 0,17 ALD 0,23 2(5H)-Furanone 0,16 KET 1,48 2-Cyclopenten-1-one 0,16 PAH 0,08 Benzaldehyde 0,15 Phenol, 4-ethenyl-, acetate 0,11 1,2-Benzenediol, 3-methyl- 0,09 1,2-Benzenediol, 4-methyl- 0,09 Phenol, 2-methyl- 0,09 Phenol, 4-ethyl-2-methoxy- 0,08 3-Furaldehyde 0,07 2-Methoxy-4-vinylphenol 0,07 Toluene 0,07 Total Top 20 compounds (wt.%) 8,65 Determined wt.% of total bio-oil 13,08 Determined wt.% of organic phase 19,64

10 Chromatographic analysis of bio-oils by GCxGC - ToFMS Cardoon bio-oil Including the H 2 O content, 71.2% of the bio-oil is characterized Highly acidic Mainly phenols are detected Compound % w/w Group Total %w/w Acetic acid 6,42 Hydroquinone 0,87 AR 0,28 1,2-Benzenediol 0,76 ALI 0,04 Phenol 0,45 PH 4,50 2(5H)-Furanone 0,41 FUR 0,11 2-Cyclopenten-1-one, 2-methyl- 0,31 AC 6,42 Phenol, 4-ethenyl-, acetate 0,26 EST 0,26 Phenol, 3-methyl- 0,17 AL <0,01 Phenol, 2,6-dimethoxy- 0,15 ETH <0,01 1,2-Benzenediol, 3-methoxy- 0,13 ALD 0,07 Phenol, 2-methoxy- 0,13 KET 1,82 1,4-Benzenediol, 2-methyl- 0,13 PAH 0,08 Ethanone, 1-(2-furanyl)- 0,13 4-Ethylcatechol 0,12 2-Cyclopenten-1-one 0,12 Phenol, 3-ethyl- 0,12 Cyclopentanone 0,11 2-Cyclopenten-1-one, 3-methyl- 0,09 1,2-Benzenediol, 4-methyl Resorcinol 0.06 Phenol, 2,5-dimethyl Total Top 20 compounds (wt.%) 11,07 Determined wt.% of total bio-oil 13,59 Determined wt.% of organic phase 32,05

11 Chromatographic analysis of bio-oils by GCxGC - ToFMS Jatropha bio-oil Including the H 2 O content, 57.6% of the bio-oil is characterized Mainly phenolic High content of aromatic nitrogen compounds Compound % w/w Group Total %w/w Acetic acid 3,88 1,2-Benzenediol 0,81 AR 0,30 Phenol 0,43 ALI 0,15 Phenol, 2-methoxy- 0,41 PH 4,39 Phenol, 3-methyl- 0,33 FUR 0,39 Hydroquinone 0,21 AC 3,88 Phenol, 2,6-dimethoxy- 0,21 EST <0,01 Phenol, 4-ethyl-2-methoxy- 0,13 AL <0,01 1,2-Benzenediol, 3-methoxy- 0,13 ETH <0,01 Toluene 0,11 ALD 0,06 2-Methoxy-6-methylphenol 0,10 KET 0,64 Phenol, 3-ethyl- 0,08 PAH <0,01 4-Ethylcatechol 0,08 1,2-Benzenediol, 4-methyl- 0,07 2-Furanmethanol 0,07 5-tert-Butylpyrogallol 0,07 2-Cyclopenten-1-one, 2-methyl- 0,07 2-Methoxy-4-vinylphenol 0,07 2-Cyclopenten-1-one, 3-methyl- 0,06 Furan, 3-methyl Ethanone, 1-(2-furanyl) Total Top 20 compounds (wt.%) 7,41 Determined wt.% of total bio-oil 9,90 Determined wt.% of organic phase 17,84

12 Chromatographic analysis of bio-oils by GCxGC - ToFMS Miscanthus bio-oil Including the H 2 O content, 66.4% of the bio-oil is characterized High acetic acid concentration Increased phenolic content Many esters detected Compound % w/w Group Total %w/w Acetic acid 8,65 1,2-Benzenediol 1,19 AR 0,06 Phenol, 4-ethenyl-, acetate 0,99 ALI 0,08 Phenol, 3-ethyl- 0,57 PH 6,89 Phenol 0,53 FUR 0,47 3-Furaldehyde 0,51 AC 8,65 2(5H)-Furanone 0,46 EST 1,00 Phenol, 2-methoxy- 0,46 AL 0,04 Phenol, 2,6-dimethoxy- 0,34 ETH 0,09 Hydroquinone 0,32 ALD 1,04 1,2-Benzenediol, 3-methoxy- 0,32 KET 2,41 2-Cyclopenten-1-one 0,30 PAH >0,01 Phenol, 3-methyl- 0,25 2-Methoxy-4-vinylphenol 0,19 2-Cyclopenten-1-one, 2-hydroxy- 0,16 2-Furanmethanol 0,14 Benzaldehyde, 4-hydroxy- 0,13 1,2-Benzenediol, 3-methyl- 0,12 Phenol, 2-methyl- 0,12 2-Cyclopenten-1-one, 2-methyl- 0,12 Vanillin 0,11 Total Top 20 compounds (wt.%) 15,97 Determined wt.% of total bio-oil 20,65 Determined wt.% of organic phase 38,09

13 Conclusions Pine Olive kernel Cardoon Jatropha Miscanthus Group Total %w/w Total %w/w Total Total %w/w %w/w Total %w/w AR 0,04 0,32 0,28 0,30 0,06 ALI 0,10 0,73 0,04 0,15 0,08 PH 8,63 5,04 4,50 4,39 6,89 FUR 0,85 0,29 0,11 0,39 0,47 AC 3,55 4,72 6,42 3,88 8,65 EST <0,01 0,12 0,26 <0,01 1,00 AL <0,01 <0,01 <0,01 <0,01 0,04 ETH 0,89 <0,01 <0,01 <0,01 0,09 ALD 1,63 0,23 0,07 0,06 1,04 KET 5,33 1,48 1,82 0,64 2,41 PAH <0,01 0,08 0,08 <0,01 >0,01 H 2 O 39,29 33,39 57,60 44,52 45,78 Developed method allows for an increased determination of the bio-oils composition than previously reported in the literature Pine bio-oil has the highest phenolics content Olive kernel bio-oil has the lowest aqueous content. Many organic acids and hydrocarbons have been detected Jatropha bio-oil has the lowest phenolics content but an increased nitrogen compounds content Cardoon has the highest H 2 O content indicating extensive cracking during the pyrolysis Miscanthus bio-oil has the highest acetic acid content and an increased phenolics content

14 CENTRE FOR RESEARCH AND ΤECHNOLOGY-HELLAS CHEMICAL PROCESS ENGINEERING RESEARCH INSTITUTE THANK YOU FOR YOUR ATTENTION!

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