1. PSE 406 - Lecture 11 Natural Product Chemistry PSE 406 Autumn Quarter 2009

2. PSE 406 - Lecture 12 Agenda l Introductions l Course syllabus » Web site http://faculty.washington.edu/renatab/courses/PSE406/ » Expectations l Rice Krispies Treats l Bioenergy

3. PSE 406 - Lecture 13 Your Instructor: Renata Bura l B.Sc.,1997, Ryerson University, Toronto, Canada, Chemistry l M.A.Sc., 2000, University of Toronto, Chemical Engineering and Applied Science and Environmental Engineering l Ph.D., 2004, University of British Columbia, Vancouver, Canada, Forestry l Post Doc., 2006, UBC, Vancouver, Canada l 2006, joined UW-Assistant Professor in Natural Products Chemistry

4. PSE 406 - Lecture 14 Renata’s Journey Toronto Vancouver Seattle

5. PSE 406 - Lecture 15 Course Information l Syllabus » Meet M/W/F 1:30-2:20pm » Office hours (….)? » Mark breakdown –Midterm 1 20% –Midterm 2 20% –Final exam 30% –Quizzes 25% –Class participation 5% l Lecture notes, practice and homework assignments-web l Reading assignments: library-Wood Chemistry, Fundamentals and Applications by E. Sjöström and web

6. PSE 406 - Lecture 16 What can you expect from me? l Starting and finishing lectures on time l Responding to your e-mails (up to 2 days) l Being in my office during office hours l Teaching the best to my ability l There are no “stupid questions”

7. PSE 406 - Lecture 17 Rules in the classroom l Cellphones l Laptops l “Daily” readers l Academic misbehavior l Rules of discussion

8. PSE 406 - Lecture 18 How is Wood like a Kellogs™ Rice Krispies Treat? l Your warped instructor needed some sort of an analogy to assist people in understanding wood. l This is it. Image borrowed from Kellogs™ web site for academic purposes

9. PSE 406 - Lecture 19 Rice Krispies Alone l At my home, a box of Rice Krispies consists of 2 things: Rice Krispies and Rice Krispies dust. l You can pour this mixture into a bowl but you cannot stand it up or make a bar. Image borrowed from Kellogs™ web site for academic purposes

10. PSE 406 - Lecture 110 Formation of the Bar l You also need something to preserve the bars….A variety of preservatives can be used. l In order to make a solid bar, you need something to glue together the Rice Krispies and the Rice Krispies dust. l Marshmallow cooked over an open flame works great.

11. PSE 406 - Lecture 111 Rice Krispies Treats The butter and the marshmallows are heated together forming a sticky glue type material. This is applied to the Rice Krispies and dust forming a bar which is solid when cooled.

12. PSE 406 - Lecture 112 What is Cellulose? l Cellulose is a large molecule made from glucose molecules (dextrose) strung together like beads on a string. l The glucose molecules are known as monomers and the cellulose chain is known as a polymer. » 1 glucose molecule= monomer » 2 linked glucose molecules= dimer » 3 linked glucose molecules= trimer » lots of linked glucose molecules = polymer

13. PSE 406 - Lecture 113 What is Cellulose? l Cellulose is straight chain polymer. In bead terms, imagine a very very long straight string of beads with 2 ends and no branching points. l In wood, cellulose chains contain typically 10,000 glucose molecules…quite a long sting of beads. Source: World Book Encycopedia

14. PSE 406 - Lecture 114 What are Hemicelluloses? l Hemicelluloses are also sugar polymers but different from cellulose because they are: » Made up glucose and other sugars. » Contain some molecules other than sugars. » Branched little polymers –Much smaller than cellulose as they are made up of between 50-300 sugars (Rice Krispies Dust) l There are lots of varieties of hemicelluloses.

15. PSE 406 - Lecture 115 What is Lignin? l Lignin is a polymer like cellulose and hemicelluloses but is made with phenolic compounds (aromatic rings) instead of sugars. l Lignins are large 3 dimensional polymers that form the glue that holds the cellulose and hemicelluloses together. l Lignin has been described as 3 dimensional chicken wire. Picture taken from Katy’s chicken page.

16. PSE 406 - Lecture 116 What are Extractives? l In the Rice Krispies model, extractives compounds were represented by preservatives added to the treats. This is a very good representation of the role of a good portion of the extractives in trees. l The term extractives refers to a large variety of different chemicals produced by the tree for a variety of reasons (protection, food storage, formation of membranes, color, etc.). l Examples: what sticks to your hand when you pick up your Christmas tree, what comes out of your tea bag with hot water.

17. PSE 406 - Lecture 117 Putting it All Together l Putting all of the components together and you get wood. The cellulose and the hemicelluloses held together with lignin. l Taking the lignin away through chemical processes (pulping and bleaching) leaves these fibers of cellulose and hemicelluloses. Picture from Focus Forest Products Web Site

18. PSE 406 - Lecture 118 Bioenergy, biochemical?

19. PSE 406 - Lecture 119 What is Bioconversion? l General: a process which uses biological agents (microorganisms or protein) to transform a feedstock into desirable products. Bioethanol l A chemical/biochemical process by which lignocellulosic materials are converted to ethanol and other co-products.

20. PSE 406 - Lecture 120 Bioconversion Process Biomass Pretreatment Hydrolysis Fermentation Distillation Ethanol

21. PSE 406 - Lecture 121 Why Bioethanol?

22. PSE 406 - Lecture 122 Why Bioconversion? l Energy » An alternative source of energy for the transportation sector produced locally l Air pollution » Reduction in greenhouse gas emissions l Waste elimination » Elimination of problems with field burning/incineration, stockpiling, etc. l Socio/economical benefits » Creation of new jobs, rural development

23. PSE 406 - Lecture 123 Summary l Your instructor likes to be referred as Dr. Bura (T/F) l I will mark the practice assignments (T/F) l Final exam-40% of your marks (T/F) l Cellulose is composed of glucose and other sugars (T/F) l Hemicelluloses is made with phenolic compounds (aromatic rings) (T/F) l During bioconversion of biomass to ethanol we have: pretreatment, hydrolysis, fermentation and distillation (T/F)