Production of Biobased Butadiene for Paper Coatings (and other applications)
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1 Production of Biobased Butadiene for Paper Coatings (and other applications) Hussein Abdulrazzaq, Thomas J. Schwartz Department of Chemical & Biomedical Engineering The University of Maine Paper Days 218
2 The Need for Butadiene Alternatives
3 The Need for Butadiene Alternatives
4 Returning to an Historic Process Butadiene produced from ethanol industrially until the 196s Soviets (Lebedev Process) Union Carbide Yields were poor: ~6-7% How to improve?
5 Returning to an Historic Process Butadiene produced from ethanol industrially until the 196s Soviets (Lebedev Process) Union Carbide Yields were poor: ~6-7% How to improve? Ethanol for this process could come from pulp mill liquors, esp. sulfite (see, e.g., Aditya Birla mill in Örnsköldsvik, Sweden)
6 Improving on the Lebedev Process? Butadiene produced from ethanol industrially until the 196s Soviets (Lebedev Process) Union Carbide Yields were poor: ~6-7% How to improve?
7 Improving on the Lebedev Process? Butadiene produced from ethanol industrially until the 196s Soviets (Lebedev Process) Union Carbide Yields were poor: ~6-7% How to improve? Reaction is catalyzed by MgO-SiO 2, which is surprising. What makes this catalyst active? Will that help with the rest of the reaction scheme?
8 SiO 2 Improving on the Lebedev SiO MgO 2 SiO 2 MgO MgO MgO MgO MgO MgO MgO MgO MgO MgO MgO MgO SiO MgO SiO 2 2 SiO 2 Process? Butadiene produced from ethanol industrially until the 196s Soviets (Lebedev Process) Union Carbide Yields were poor: ~6-7% 3 wt% MgO/SBA-15 How to improve? Reaction is catalyzed by MgO-SiO 2, which is surprising. What makes this catalyst active? Will that help with the rest of the reaction scheme?
9 Selectivity (%) Acetaldehyde Selectivity Acetaldehyde Ethylene Time On Stream (hr) Selectivity to acetaldehyde is stable at ~9% for approx. 3 days on stream Reaction conditions:.2g of catalyst, reaction temperature 723 K, WHSV =.6.36 min -1, ethanol partial pressure kpa, and total pressure 11 kpa.
10 STY (hr -1 ) Selectivity (%) Acetaldehyde Selectivity Acetaldehyde Selectivity remains constant even at infinite space velocity 3 2 Ethylene E+1 2.5E+1 Time On Stream (hr) 2E+1 1.5E+1 Selectivity to acetaldehyde is stable at ~9% for approx. 3 days on stream Reaction conditions:.2g of catalyst, reaction temperature 723 K, WHSV =.6.36 min -1, ethanol partial pressure kpa, and total pressure 11 kpa. 1E+1 5E WHSV -1 (hr -1 )
11 Observed Rate (µmol g -1 min -1 ) Catalyst Stability 12 1 Rapid deactivation during first ~8 hrs Acetaldehyde Time on Stream (hr) Ethylene Reaction Conditions:.67g catalyst, WHSV = min -1, ethanol partial pressure 3.7 kpa, reaction temperature 723 K, and total pressure kpa.
12 Observed Rate (µmol g -1 min -1 ) Catalyst Stability 12 1 Rapid deactivation during first ~8 hrs Acetaldehyde Time on Stream (hr) Ethylene Reaction Conditions:.67g catalyst, WHSV = min -1, ethanol partial pressure 3.7 kpa, reaction temperature 723 K, and total pressure kpa.
13 Observed Rate (µmol g -1 min -1 ) Observed Rate (µmol g -1 min -1 ) Catalyst Stability 12 1 Rapid deactivation during first ~8 hrs Fit remaining deactivation assuming two parallel 1 st -order processes Time on Stream 1 (hr) Acetaldehyde Ethylene Acetaldehyde Ethylene Time On Stream (hr) Reaction Conditions:.67g catalyst, WHSV = min -1, ethanol partial pressure 3.7 kpa, reaction temperature 723 K, and total pressure kpa.
14 Prod. Rate (µmol g -1 min -1 ) Influence of ethanol on reactivity K Ethanol Partial Pressure (kpa) Reaction Conditions:.67g of catalyst, WHSV = min -1, ethanol partial pressure kpa, total pressure kpa.
15 Prod. Rate (µmol g-1 min-1) Influence of ethanol on reactivity K 698 K 673 K 648 K Ethanol Partial Pressure (kpa) Reaction Conditions:.67g of catalyst, WHSV = min -1, ethanol partial pressure kpa, total pressure kpa.
16 Prod. Rate (µmol g-1 min-1) Prod. Rate (µmol g-1 min-1) Influence of ethanol on reactivity 723 K 698 K 673 K 648 K Ethanol Partial Pressure (kpa) 723 K Ethanol Partial Pressure (kpa) Reaction Conditions:.67g of catalyst, WHSV = min -1, ethanol partial pressure kpa, total pressure kpa.
17 Prod. Rate (µmol g-1 min-1) Prod. Rate (µmol g-1 min-1) Influence of ethanol on reactivity 723 K 698 K 673 K 648 K Ethanol Partial Pressure (kpa) 723 K 698 K 673 K Ethanol Partial Pressure (kpa) Reaction is essentially zero-order wrt. ethanol surface is highly covered by ethanol-like species? Reaction Conditions:.67g of catalyst, WHSV = min -1, ethanol partial pressure kpa, total pressure kpa.
18 Normalized Prod. Rate (µmol g -1 min -1 ) Normalized Prod. Rate (µmol g -1 min -1 ) Searching for a 1 st -order regime? Ethanol Partial Pressure (kpa) Reaction is zero-order even when dropping to the lowest pressures we can reliably measure! Reaction Conditions:.67g of catalyst, WHSV = min -1, ethanol partial pressure kpa, total pressure kpa Ethanol Partial Pressure (kpa)
19 Prod. Rate (µmol g-1 min-1) Prod. Rate (µmol g-1 min-1) Influence of ethanol on reactivity 723 K 698 K 673 K 648 K Ethanol Partial Pressure (kpa) 723 K 698 K 673 K Ethanol Partial Pressure (kpa) Apparent activation barrier for dehydrogenation is much lower than that for dehydration. Reaction Conditions:.67g of catalyst, WHSV = min -1, ethanol partial pressure kpa, total pressure kpa.
20 Further probing the mechanism Kinetic Isotope Effect Reactant CH 3 CH 2 OD CD 3 CD 2 OD ethylene KIE (r H /r D ) acetaldehyde KIE (r H /r D ) Observed KIE for dehydration, not for dehydrogenation! Reaction Conditions:.67g of catalyst, 698 K, 3.8 kpa ethanol, total pressure kpa.
21 Observed Rate (µmol g -1 min -1 ) Further probing the mechanism Kinetic Isotope Effect Reactant CH 3 CH 2 OD CD 3 CD 2 OD Pyridine Titration Acetaldehyde ethylene KIE (r H /r D ) acetaldehyde KIE (r H /r D ) Ethylene Observed KIE for dehydration, not for dehydrogenation! Reaction Conditions:.67g of catalyst, 698 K, 3.8 kpa ethanol, total pressure kpa. Time On Stream (hr) Rapid deactivation in the presence of pyridine suggest involvement of acid sites (surprising for Mg-containing catalyst!)
22 Reaction Mechanism?
23 Reaction Mechanism? rate = K 1 k 2 P C2H5OH ( 1 + K 1 P C2H5OH ) 2
24 Summary Production of butadiene from pulp mill liquors is limited by our understanding of the Lebedev reaction Dehydrogenation over an irreducible oxide catalyst is surprising Reactivity is driven by cooperation between basic and Lewis acidic sites Reactivity is limited by strong adsorption of reactive intermediates Improved catalysts must decrease the binding energy of ethoxide to Mg sites
25 Summary Production of butadiene from pulp mill liquors is limited by our understanding of the Lebedev reaction Dehydrogenation over an irreducible oxide catalyst is surprising Reactivity is driven by cooperation between basic and Lewis acidic sites Reactivity is limited by strong adsorption of reactive intermediates Improved catalysts must decrease the binding energy of ethoxide to Mg sites
26 Summary Production of butadiene from pulp mill liquors is limited by our understanding of the Lebedev reaction Dehydrogenation over an irreducible oxide catalyst is surprising Reactivity is driven by cooperation between basic and Lewis acidic sites Reactivity is limited by strong adsorption of reactive intermediates Improved catalysts must decrease the binding energy of ethoxide to Mg sites
27 Summary Production of butadiene from pulp mill liquors is limited by our understanding of the Lebedev reaction Dehydrogenation over an irreducible oxide catalyst is surprising Reactivity is driven by cooperation between basic and Lewis acidic sites Reactivity is limited by strong adsorption of reactive intermediates Improved catalysts must decrease the binding energy of ethoxide to Mg sites
28 Summary Production of butadiene from pulp mill liquors is limited by our understanding of the Lebedev reaction Dehydrogenation over an irreducible oxide catalyst is surprising Reactivity is driven by cooperation between basic and Lewis acidic sites Reactivity is limited by strong adsorption of reactive intermediates Improved catalysts must decrease the binding energy of ethoxide to Mg sites
29 Acknowledgements UMaine Catalysis Research Group Students: - Hussein Abdulrazzaq - Jalal Tavana - Elnaz Jamalzade - Daniela Stuck - Christopher Albert Group Alumni: - Meredith Allen - Mohammed Al-Gharrawi Funding:
30 Questions?
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