1. The Soybean Project JOSHUA POTVIN

2. Overview Introduction Background AESBO/PAESBO ◦Experimental ◦Results/Discussion Personal Experience Questions?

3. Introduction Freshman Honors Program ◦First-Year Mentor Program Soybean Project ◦Goals ◦Acrylation ◦Polymerization ◦Optimization For pilot plant

4. Background Soybean Oil ◦In pilot plant phase Acrylation ◦Kinetics Polymerization ◦RAFT ◦Crashing/Recovery

5. AESBO- Experimental Setup: ◦Originally ◦Everything at once ◦Including solvent ◦Longer Big Reactor Aliquots and NMR ◦Terminal Methyl ~ 9 ◦Glycerol back bone ~ 4 New Setup (Kinetics) ◦ESBO and Ethanox 330 ◦Melt ◦Amberlyst 15 ◦Mix ◦1 st Magnetic Stir Bars ◦2 nd Mechanical Stirring ◦Acrylic Acid (2.5 functionality) ◦8 hrs

6. AESBO-Experimental Three Reactions 1.Acrylation 2.Hydrolysis 3.Polymerization

7. PAESBO- Experimental Second Part of Semester Big Reactor RAFT- ◦4:1 Solvent to Monomer ◦CTA and Initiator ◦1 : 0.65 ◦Purging ◦Polymerization ◦2 hr 20 min. Ethanox ◦Crashing ◦2 hrs 30 min. ◦Water/ Methanol ◦Recovery ◦AESBO settled at the bottom ◦Crosslinking

8. AESBO- Results First Trial: ◦Cross-linked Kinetics

9. AESBO-Results

12. ESO-Viscosity 30ºC50ºC65ºC75ºC80ºC 1750625500250 5450150 100 1037512575 20337.5112.562.550 33090554035 10032585503527.5 Viscosity c Pa RPM

13. PAESBO-Mechanism RAFT Mechanism ◦Initiator ◦Free Radicals ◦Attacks Monomer ◦CTA ◦Adds monomer ◦Propagates ◦Continues until all monomer is used up ◦Crosslinking Crashing ◦Goal ◦What helps crash PAESBO the best? ◦Many ways ◦Methanol ◦Water ◦Methanol/water ◦Methanol/Ethanol/Water ◦Retrieval

14. PAESBO-Results ChemicalRatioMASS [gram]Volume (Monomer)AESBO ~2.5 Functionality 90.81 by mol of CTA173190.32 (Initiator) AIBN.65 by mol of CTA.184Solid (CTA) ETMP1.508.452 (Solvent) MeTHF4 by mass of monomer690810.30

15. PAESBO-Results Experimental runReaction sizeYield MW PAESBO 140 gram65%330 kDa PAESBO 240 gram60%100 kDa PAESBO 3 (Big reactor)1700 gram80%100 kDa PAESBO 4 (Chlorination)40 gram50%100 kDa

16. PAESBO-Results Viscosity 30 °C 60 °C 75 °C

17. PAESBO- Results GPC is unavailable for my samples since the GPC machine was down while I have been working on polymerization.

18. Personal Experience THINGS I LIKED Independence First-hand experience Working as a group Working with Austin The project as a whole THINGS I DID NOT LIKE “Too much” independence at times

19. Personal Experience What I learned: ◦My career interests ◦How polymerization works ◦What research in chemical engineering is like ◦How to think better for myself ◦How to better work in a group

20. Questions?