demystifying green chemistry my goal today371.82 atom economy = 41% 154.24 three levels of green...

10
1 Demystifying Green Chemistry Bob Hanson Department of Chemistry St. Olaf College Northfield, MN 55057 [email protected] Michigan State University Aug. 10, 2005 My Goal Today Tell you a bit about St. Olaf and our Green Chemistry project Present a brief introduction to Green Chemistry Introduce a new way of working with Green measures Founded in 1874 by Norwegian immigrants Liberal arts college Known for music, international, and science- mathematics programs 2900-3000 students – 40% majoring in science and mathematics Average of 45 chemistry majors/year Construction on Phase 1 of new science facilities will begin in June 2007 St. Olaf College www.stolaf.edu Boe Chapel Holland Hall Old Main St. Olaf Chemistry Green Chemistry Group not shown: Paul Campbell, Paul Jackson

Upload: others

Post on 30-Jul-2020

0 views

Category:

Documents


0 download

TRANSCRIPT

Page 1: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

1

� � � � � � � � � � � �

Demystifying Green Chemistry

Bob Hanson

Department of Chemistry

St. Olaf College

Northfield, MN 55057

[email protected]

Michigan State UniversityAug. 10, 2005

� � � � � � � � � � � �

My Goal Today

�Tell you a bit about St. Olaf and our Green Chemistry project

�Present a brief introduction to Green Chemistry

�Introduce a new way of working with Green measures

� � � � � � � � � � � �

�Founded in 1874 by Norwegian immigrants

�Liberal arts college

�Known for music, international, and science-mathematics programs

�2900-3000 students – 40% majoring in science and mathematics

�Average of 45 chemistry majors/year

�Construction on Phase 1 of new science facilities will begin in June 2007

St. Olaf College

� � � � � � � � � � � �

www.stolaf.edu

Boe Chapel Holland Hall Old Main

� � � � � � � � � � � � � � � � � � � � � � � �

St. Olaf Chemistry Green Chemistry Group not shown: Paul Campbell, Paul Jackson

Page 2: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

2

� � � � � � � � � � � �

“ Green Chemistry Throughout the Curriculum” Project Goals

�Design a suite of experiments that exemplifies the principles of GC for use at all levels of our laboratory curriculum.

�Develop these experiments in such fashion that they demonstrate an intentional thread, illustrating GC principles throughout the chemistry curriculum.

�Design these experiments such that they are based upon work reported in the contemporary chemical literature.

� � � � � � � � � � � �

�Increase student awareness of the principles of GC throughout our curriculum

�Produce future scientists who will be leaders in the implementation of GC in their workplace.

�Tie in the principles of GC with the ethical perspective central to St. Olaf College’s mission statement.

“ Green Chemistry Throughout the Curriculum” Project Goals

� � � � � � � � � � � �

�Demonstrate that the use of GC provides a guiding principle for the design and use of our new science building and other future science buildings.

�Provide a model for a green chemistry laboratory experience suitable for use at other colleges and universities.

“ Green Chemistry Throughout the Curriculum” Project Goals

� � � � � � � � � � � �

“ Green Chemistry Throughout the Curriculum” Timeline

�Organic lab (2003)

�WM Keck Foundation Grant (2004)

�Chemistry 121 pilot (2005)

�Chemistry 125 (2006)

�Analytical Chemistry (2007)

� � � � � � � � � � � �

My Role

�Bring Green Chemistry ideas into the first-year curriculum

�Use Green Chemistry as a means of introducing a wide range of ideas

�Design a web-based introduction to Green Chemistry measurements

� � � � � � � � � � � �

So, What is “ Green Chemistry” ?

Page 3: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

3

� � � � � � � � � � � � � � � � � � � � � � � �

� � � � � � � � � � � � � � � � � � � � � � � �

� � � � � � � � � � � �

Three Levels of Green Chemistry

Equations

HCl (aq) + NaOH (aq)�

NaCl (aq) + H2O (l)

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reactions

http://www.uncw.edu/smec/gk_fellows/askscience.html

Page 4: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

4

� � � � � � � � � � � �

Three Levels of Green Chemistry

Processes

www.shelldeerpark.com/chemical.htm

� � � � � � � � � � � �

Three Levels of Green Chemistry

Equation – PCC Oxidation of Menthol

Atom Economy = 41%371.82

154.24

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction

Atom Economy = 41%

theoretical yield

0% reaction

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction

25% reaction

coproducts

desiredproduct

Atom Economy = 41%

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction

50% reaction

coproducts

desiredproduct

Atom Economy = 41%

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction

75% reaction

coproducts

desiredproduct

Atom Economy = 41%

Page 5: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

5

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction

Atom Economy = 41%100% reaction

coproducts

desiredproduct

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction

Atom Economy = 41%

before… …after

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction – Limiting Reactant

Experimental Atom Economy = 26%

before… …after

excess PCC

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction – Actual Yield

Reaction MassEfficiency = 13%

before… …after

50% Product Loss

� � � � � � � � � � � �

Three Levels of Green Chemistry

Reaction – General Measures

Reaction Mass Eff iciency = 13%Exper. Atom Economy = 26%Atom Economy = 40%

� � � � � � � � � � � �

Three Levels of Green Chemistry

Process – Includes all inputs

Process MassEff iciency = 1%solvent silica gel

Page 6: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

6

� � � � � � � � � � � �

Three Levels of Green Chemistry

Process MassEff iciency = 13%

Process – May involve more than one step

David Harris, ’ 06

Atom Economy= 81%

catalysts

bypoduct (H2O)

� � � � � � � � � � � �

Three Levels of Green Chemistry

H2O2/Na2WO4

Process MassEff iciency = 13%

…allows for comparison

Process…PCC

Process MassEff iciency = 1%

� � � � � � � � � � � �

Three Levels of Green Chemistry

E-factor = 0.3:1

Process – Allowing for solvent recovery

E-factor = 6.5:1

solventlost

solvent recovered

� � � � � � � � � � � �

Three Levels of Green Chemistry

Equation, Reaction, and Process

Wouldn’t it be nice to have access to a tool that would allow us to quickly make comparisons like this?

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

�Based on the EPA “Green Chemistry Expert System”

�User-friendly interface designed to assist students in analyzing the atom economy, and safety of chemical processes

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Page 7: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

7

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Page 8: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

8

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Page 9: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

9

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

http://fusion.stolaf.edu/gca

http://fusion.stolaf.edu/gca?file=samples/menthol_pcc.htm

http://fusion.stolaf.edu/gca?file=samples/menthol_h2o2.htm

http://fusion.stolaf.edu/gca?file=samples/uo_aldol.htm

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Lessons learned:�

Students need help just writing the balanced chemical equations.

�Process is important, as most realexperiments involve more than one process step.

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Lessons learned:�

Introducing Green Chemistry provides a context for discussing safety, including MSDS sheets, health, and environmental hazards.

� � � � � � � � � � � �

Green Chemistry Assistanthttp://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.

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Lessons learned:�

Web applications can provide accessible methods of introducing students to Green Chemistry calculations and issues.

�The key is a smooth, well-tested interface, utilizing lots of student feedback.

� � � � � � � � � � � �

Green Chemistry Assistanthttp://fusion.stolaf.edu/gca

Things to do:�

Add the final post-process analysis page “Account for Material Recovery”

�Generate Final Green Process Reports

�Get ideas from user feedback!

Page 10: Demystifying Green Chemistry My Goal Today371.82 Atom Economy = 41% 154.24 Three Levels of Green Chemistry Reaction Atom Economy = 41% theoretical yield 0% reaction Three Levels of

10

� � � � � � � � � � � �

St. Olaf Faculty

St. Olaf Students

St. Olaf Technology Support

U.S. EPA

Financial support

Acknowledgments

Gary Spessard, Marc Klingshirn, Paul Jackson

Paul Campbell, Allison Christensen, Tim Barker, Tyler Drake, David Harris

Dan Beach

Rich Engler

WM Keck FoundationHoward Hughes Medical Institute

� � � � � � � � � � � �

St. Olaf Chemistry Green Chemistry Group not shown: Paul Campbell, Paul Jackson