Sustainable, Safe and Scalable Stationary Energy Storage

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1 rganic edox-flow-batteries Sustainable, Safe and Scalable Stationary Energy Storage Dr. laf Conrad, Managing Director

About JenaBatteries Gmb (JB) Founded in 2012, JB holds the global patent for Polymer-based-edox-Flow-Batteries and filed further patents in

2016, JB attracted two new investors with comprehensive expertise in &D, engineering and business development.

producing stationary energy storage systems (with a capacity above 40 kwh).

2 About JenaBatteries Gmb (JB) Founded in 2012, JB holds the global patent for Polymer-based-edox-Flow-Batteries and filed further patents in the field of organic radical redox flow batteries we won the IQ Innovationspreis 2015 (Mitteldeutschland). 2016, JB attracted two new investors with comprehensive expertise in &D, engineering and business development. JenaBatteries is growing rapidly (5 employees in August 2016 to currently 16 employees) JenaBatteries ist focused on developing and producing stationary energy storage systems (with a capacity above 40 kwh). Currently delivering pilot installations in Germany and The etherlands Actively building a global network of project development and technical support partners based on a collaborative licensing business model JB is supported by: omepage:

near-neutral p o toxic heavy metals, no critical raw materials Inexpensive raw materials and

3 JenaBatteries Cost effective organic based redox flow batteries Metal-free energy storage system based on patented organic, redox-active energy storage materials Water based, near-neutral p o toxic heavy metals, no critical raw materials Inexpensive raw materials and membranes > cycles 10 kw to 2 MW and 40 kwh to 10 MWh Targeted installation cost < 500 /kwh

4 Management Team & wners Management Team: Dr. laf Conrad Managing Director Carsten der System & Electronics Dr. orbert Martin Electrolyte & Material Tobias Janoschka Corporate Development Michael-Lothar Schmidt BD & Marketing wners: Wirthwein AG anft Gruppe

5 Current material basis & challenges Cobalt (Lithium) Lead are earth elements (i-me) Vanadium (FB) Plus icd o sustainable raw material basis Important battery issues: Safety Sustainability Scalability Cycle Stability

6 rganic Active Materials and their edox Potentials Viologen TEMP 2 evolution Water stability 2 evolution 0.0 V Water based flow batteries desireable due to higher safety, higher conductivity and price despite lower cell voltage TEMP / Viologen systems utilize a large portion of the potential available in water J. Winsberg et al. Angew. Chem. Int. Ed.,2017, 56,

poly(pyrrole)/lithium (1987) Commercial button cells flopped Bridgestone-Seiko poly(aniline)/lithium

7 Conductive polymers & batteries poly(acetylene) poly(pyrrole) poly(aniline) n n n Discovered 1977, obel price in Chemistry 2000 ( for the discovery and development of conductive polymers ) VATA/BASF poly(pyrrole)/lithium (1987) Commercial button cells flopped Bridgestone-Seiko poly(aniline)/lithium ( ) J. S. Miller, Adv. Mater. 1993, 5, ; D. aegele,. Bittihn, Solid State Ionics 1988, 28-30,

Conductive polymer battery Desired discharging behavior Capacity / % sloping redox potential (redox

8 Polymer-based energy storage? conductive polymers redox polymers Cell voltage / a.u. Conductive polymer battery Desired discharging behavior Capacity / % sloping redox potential (redox potential gradually changes upon charging/discharging) useless for numerous applications polymers with distinct redox potential attributed to localized redox sites stable cell voltage Adv. Mater. 2012, 24,

9 Bi-Polar Polymers - Poly(BDIPY) rganic Solvents J. Winsberg. et al. Chem. Mater., 2016, 28 (10), pp

10 Polymer design for aqueous systems TEMP- and viologen-polymers for water-based redox-flow batteries A + A + A + A + + m n 2 2 a 2 W 4 m 450 g mol = a -(C2C 2 ) -1 nc 3 = b 950 g mol 2C 2 ) -1 nc 3 = c -(C 2C 2 ) 2 C 3 = d - 2 = e -(C + Cl- 2)2(C3)

1 1 10 100 < h > n,app / nm T. Janoschka,. Martin, U. Martin, C. Friebe, S. Morgenstern,.

11 Design criteria for TEMP and Viologen Polymers n m X Polar group Energy Storage Monomer (EM) Solubilizing Monomer (SM) n m Polar group P1 P2 Cl Intensity / a.u. Energy Storage Monomer (EM) Cl < h > n,app / nm T. Janoschka,. Martin, U. Martin, C. Friebe, S. Morgenstern,. iller, M. D. ager, U. S. Schubert, ature 2015, 527,

12 Co-Polymer for TEMP and Viologen Polymers + 1. Cl/ 2 2. ABCVA/SC a/ 2 n m a 2 W 4 / 2 2 n m Cl Cl 1 2 P1 Cl + DMS AIB n m n m I ion exchange Cl Cl Cl Cl Cl Cl 3 4 P2 Cl T. Janoschka,. Martin, U. Martin, C. Friebe, S. Morgenstern,. iller, M. D. ager, U. S. Schubert, ature 2015, 527,

13 heological Data and Charge / Discharge Behavior in Flow Cells Viscosity / Pa s Shear rate / s -1 P1 P2 Cell voltage / V P1: - e - + e - TEMP TEMP + P2: + e - - e - Viol ++ Viol ,000 10,000 15,000 Time / s Viscosity in flow range (shear rate > 1 s -1 between 5 and 20 mpas Stable redox cycling in water based solutions confirmed T. Janoschka,. Martin, U. Martin, C. Friebe, S. Morgenstern,. iller, M. D. ager, U. S. Schubert, ature 2015, 527,

solubility will lead to higher capacity, ion mobility, current density more

14 Small molecules -based FB active material aqueous electrolyte catholyte tank anolyte tank Cl Cl electrode ion-selective membrane low viscosity and good solubility will lead to higher capacity, ion mobility, current density more expensive ion-selective membrane simplified synthetic access allows for lower-cost electrolyte

Cathode commercially available low-cost low retention by membrane C expensive anionic species low retention by membrane 2 expensive low retention by membrane not commercially available high retention

15 Cathode commercially available low-cost low retention by membrane C expensive anionic species low retention by membrane 2 expensive low retention by membrane not commercially available high retention by membrane low solubility of TEMPL of only 0.5 mol/l in 1.5 mol/l acl aq 13 Ah/L high solublity of MV, but only 0.5 mol/l demonstrated high amount of supporting electrolyte (1.5 mol/l acl aq ) T. Liu, X. Wei, Z. ie, V. Sprenkle, W. Wang, Adv. Energ. Mat. 2015, DI: /aenm

16 Improved synthesis route Me 2 (gas), 2, Pd/C, Me C 3 Cl MeC/toluene Cl 2 2/MgS4 Cl up-scaling to kg-scale by substitution of dimethylammonium hydrochloride (difficult purification procedure) with dimethylamine gas substitution of expensive, B-based reduction agent with hydrogen direct methylation with chloromethane and substitution of C 3 I low-cost oxidation catalyst simple purification procedures T. Janoschka,. Martin, M. D. ager, U. S. Schubert, Angew. Chem. Int. Ed ov 7;55(46):

17 igh cyclability of the storage material Capacity / mah esidual Capacity [%] Coulombic efficiency / % -e - +e - Zyklus Cycle number Facile one-electron transfer reactions without ion insertion/intercalation on charge and discharge no mechanical stress, no volume change high cycle stability Molecular structure unchanged during charging/discharging no degradation from conformational changes Excellent cross-over characteristics due to size and charge of storage material T. Janoschka et al. Angew. Chem., Int. Ed.2016, 55,

Practical energy density > 20 Wh/l esting Voltage [V] Leerlaufspannung [V] 1,40 1,35 1,30 1,25 1,20 1,15 1,10 0 20 40 60 80 100 State Ladezustand of Charge [%] [%] Supporting electrolyte [wt-%] 17 10

18 Practical energy density > 20 Wh/l esting Voltage [V] Leerlaufspannung [V] 1,40 1,35 1,30 1,25 1,20 1,15 1, State Ladezustand of Charge [%] [%] Supporting electrolyte [wt-%] rganic storage material [wt-%] esting voltage at SC = 50% is 1.25 V, compare to im-battery 1.2 V Solubility of organic storage material is > 50 wt-% ptimization with acl concentration viscosity <-> conductivity <-> energy density Design point for product at 20 Wh/l, lab scale demonstration of up to 35 Wh/l T. Janoschka et al. Angew. Chem., Int. Ed.2016, 55,

heological behaviour allows for wide operating

viscosity results in low pumping losses Viscosity at

mpas (catholyte) at 25 C, respectively Compare

10.000 mpas At 5 C viscosity remains suitably low at

19 heological behaviour allows for wide operating window Viscosity is impacting the pumping losses low viscosity results in low pumping losses Viscosity at design point (20 Wh/l) is 3 mpas (anolyte) and 6 mpas (catholyte) at 25 C, respectively Compare water: 1 mpas, grape juice mpas, syrup approx mpas At 5 C viscosity remains suitably low at 5 mpas (anolyte) and 12 mpas (catholyte), respectively

20 Stack efficiency > 85% at rated stack power of 5 kw Verlustanteil (%) Leistung Entladen (kw) Leistung Laden (kw) Leistung Stack (kw) Widerstand [hm*cm²] Ladegrad (SoC): % esults from laboratory installation Temperatur [ C] Stack design allows high efficiency at rated power with ability to deliver 2x peak power peration at higher temperatures improves stack efficiency and overall system efficiency Elevated temperature reduces ohmic stack losses and pumping losses

Pilot Installation I 10 kw / 40 kwh Project targets Development of new organic storage materials Mass production ready stack design Development of a

initial tests at the end of 2017 Installation in the field in Q1/2018 Collaboration with regional development and production partners Dieses Projekt wird

21 Pilot Installation I 10 kw / 40 kwh Project targets Development of new organic storage materials Mass production ready stack design Development of a battery management system Extended operation data Containerised solution Coupling to a PV-installation in Thuringia/Germany Status Final assembly and initial tests at the end of 2017 Installation in the field in Q1/2018 Collaboration with regional development and production partners Dieses Projekt wird von der Europäischen Union (EFE) und dem Freistaat Thüringen (Thüringer Ministerium für Wirtschaft, Wissenschaft und Digitale Gesellschaft) kofinanziert

Pilot Installation II 100 kw / 350 kwh Scale up of

organic FB with a Smart Grid Wind, PV, biomass

agricultural enterprise Development of business

Battery introduced via Plug & Play-capability Status

Setup and operation planned for Q3/2018 10 partners

received funding from the European Union s orizon

22 Pilot Installation II 100 kw / 350 kwh Scale up of pilot installation I by factor of 10 Coupling of an organic FB with a Smart Grid Wind, PV, biomass BEV-Charging station, residential building, agricultural enterprise Development of business models Development of an energy management system Battery introduced via Plug & Play-capability Status ardware and software engineering nearing completion Setup and operation planned for Q3/ partners from 5 EU-countries + Israel This project has received funding from the European Union s orizon 2020 research and innovation program under grant agreement o

23 Thank you for your attention!

Organic / Polymer Redox-Flow-Batteries for Stationary Energy Storage Applications

Organic / Polymer Redox-Flow-Batteries for Stationary Energy Storage Applications Ulrich S. Schubert Laboratory of Organic and Macromolecular Chemistry (IOMC) Center for Energy and Environmental Chemistry