robert m. hanson , paul r. campbell, marc a. klingshirn, and gary o. spessard st. olaf college
DESCRIPTION
Using the web-based Green Chemistry Assistant to enhance understanding of chemical reactions and processes. Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College Northfield, MN 55057 [email protected] - PowerPoint PPT PresentationTRANSCRIPT
![Page 1: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/1.jpg)
Green Chemistry
Using the web-based Green Chemistry Assistant to enhance
understanding of chemical reactions and processes
Robert M. Hanson, Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard
St. Olaf CollegeNorthfield, MN [email protected]
19th Biennial Conference on Chemical Education,Purdue University
Aug 3, 2006
![Page 2: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/2.jpg)
Green Chemistry
Green Chemistry Definitions
• “The utilization of a set of principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture, and application of chemical products.” -- Anastas and Warner; Doxie and Hutchison.
• “The design of chemical products or processes to reduce or eliminate the use or generation of hazardous substances.” -- Tundo and Anastas, Green Chemistry: Challenging Perspectives, 2000.
![Page 3: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/3.jpg)
Green Chemistry
Three Levels of Green Chemistry
Processes
www.shelldeerpark.com/chemical.htm
![Page 4: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/4.jpg)
Green Chemistry
Three Levels of Green Chemistry
Reactions
http://www.uncw.edu/smec/gk_fellows/askscience.html
![Page 5: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/5.jpg)
Green Chemistry
Three Levels of Green Chemistry
Equations
HCl (aq) + NaOH (aq) NaCl (aq) + H2O (l)
![Page 6: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/6.jpg)
Green Chemistry
http://fusion.stolaf.edu/gca
http://fusion.stolaf.edu/gca/goc1.htm
http://fusion.stolaf.edu/gca/goc2.htm
http://fusion.stolaf.edu/gca/goc3.htm
![Page 7: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/7.jpg)
Green Chemistry
http://fusion.stolaf.edu/gca/goc1.htm
![Page 8: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/8.jpg)
Green Chemistry
http://fusion.stolaf.edu/gca/goc2.htm
![Page 9: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/9.jpg)
Green Chemistry
http://fusion.stolaf.edu/gca/goc3.htm
![Page 10: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/10.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Lessons learned:
• Students need help just writing the balanced chemical equations.
• Process is important, as most real experiments involve more than one process step.
![Page 11: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/11.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Lessons learned:
• Lab manuals could be more explicit in guiding students to an understanding of the overall set of process steps they will be doing in lab.
![Page 12: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/12.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Question:
What is the balanced chemical equation for this reaction?
OHTsCl / Et3N
OTs
![Page 13: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/13.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Is it this?... (atom economy = 88%)
OH
OTs
+ TsCl
+ HCl
![Page 14: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/14.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
…or this? (atom economy = 66%)
OH
OTs
+ TsCl + Et3N
+ Et3NHCl
![Page 15: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/15.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Question:
What is the balanced chemical equation for this reaction?
OH1) BH3 THF
2) H2O2/NaOH
![Page 16: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/16.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Question:
Is this one reaction or two?
OH1) BH3 THF
2) H2O2/NaOH
![Page 17: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/17.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Question:
What is the atom economy?
OH1) BH3 THF
2) H2O2/NaOH
![Page 18: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/18.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
OH
3 + BH3THF + THFB
3
3B
3
STEP 1STEP 1
STEP 2 + 3 H2O2
+ NaOH+ NaB(OH)4
Overall Atom Economy = 60%
![Page 19: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/19.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
OH
3 + BH3B
3
3B
3
STEP 1STEP 1
STEP 2 + 3 H2O2
+ NaOH+ NaB(OH)4
Overall Atom Economy = 72%
![Page 20: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/20.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
OH
3 + BH3THF + THFB
3
3B
3
STEP 1STEP 1
STEP 2 + 3 H2O2
+ NaOH+ NaB(OH)4
STEP 3 BH3THF + 3 H2O + NaOH THF + NaB(OH)4 + 3 H2 (g)
In practice, Step 3 is important!
![Page 21: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/21.jpg)
Green Chemistry
Green Chemistry Assistant http://fusion.stolaf.edu/gca
Lessons learned:• Getting students thinking about the overall
process is good.• Expecting them to do it on their own because it’s
“simple” is asking too much.• The Green Chemistry Assistant enables us to
explore the nature of green chemistry processes and green chemistry measures.
![Page 22: Robert M. Hanson , Paul R. Campbell, Marc A. Klingshirn, and Gary O. Spessard St. Olaf College](https://reader035.vdocuments.net/reader035/viewer/2022070405/56813dd0550346895da7995f/html5/thumbnails/22.jpg)
Green Chemistry
FacultyGary Spessard, Marc Klingshirn, Paul Jackson
StudentsPaul Campbell, Allison Christensen, Elizabeth R.
Johnson, Tim Barker, Tyler Drake, David Harris Technology Support
Dan Beach Financial support
WM Keck FoundationHoward Hughes Medical Institute
Green Chemistry Assistant http://fusion.stolaf.edu/gca