Teaching Green and Sustainable Chemistry: A Revised One-Semester

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Teaching Green and Sustainable Chemistry: A Revised One-Semester Course Based on Inspirations and Challenges Anne E. Marteel-Parrish* Department of Chemistry, Washington College, Chestertown, Maryland 21620, United States S Supporting Information *

ABSTRACT: An elective course, Toward the Greening of Our Minds: Green and Sustainable Chemistry, has been offered at Washington College since 2005. This new course without laboratory is designed for chemistry and biology majors and minors who have previously taken two semesters of general chemistry and organic chemistry. Due to the popularity of the course, the enrollment nearly doubled since 2005. Specific changes needed to be implemented to respond to students’ feedback and needs but also to account for the expansion of the field of green chemistry. The original goals associated with this course are still incorporated yet are now addressed differently to provide students with up-to-date, quantitative, and skillful knowledge of green chemistry applications and metrics. The ultimate goal is for students to use their critical thinking skills to produce an innovation proposal and to become responsible citizens of the 21st century. KEYWORDS: Upper-Division Undergraduate, Curriculum, Problem Solving/Decision Making, Hands-On Learning/Manipulatives, Green Chemistry, Collaborative/Cooperative Learning



• The absence of coverage about the green decisionmaking process and the business component of green chemistry (identified as Gap #2), and • The difficulty keeping up with the growth of the green chemistry field and consequently with the emergence of topics such as the worldwide scope of green chemistry (identified as Gap #3) and the role of toxicology in green chemistry (identified as Gap #4). The writing-intensive nature of the course as well as the larger class size (growing from 13 students to 24 students over a period of 8 years) accentuated the need to revise the existing course. It also became essential to address the quantitative as well as the qualitative aspect of green chemistry in this course.

ORIGINAL FORMAT AND REVEALED GAPS IN THAT COURSE

An article titled “Toward the Greening of Our Minds: A New Special Topics Course” was published in 2007 by the same author.1 The course was designed around the 12 principles of green chemistry and their applications. Assignments inspired by the Presidential Green Chemistry Challenge Awards and the creation of a team miniproposal constituted the core of the original course. Since the original format and goals of the course were published in 2007, many undergraduate courses with a green chemistry focus have been developed. However, some of these courses specifically targeted nonscience majors2−4 or first-year students.5 Most of the published resources were devoted to the field of organic chemistry, explicitly using a green chemistry approach in organic chemistry courses6,7 or organic chemistry experiments.8−15 Certain courses were based on the development of a specific capstone course for undergraduate and graduate students,16 on the design of modules for teaching sustainability in a mass and energy balance course,17 or on the creation of an undergraduate course on “Catalysis in green chemistry” at the advanced level.18 In the original course, the main outcomes were improvements in effective communication and critical thinking skills. However, challenges arose due to • The lack of resources regarding the assessment of the application of the 12 green chemistry principles, and consequently how to practice green chemistry metrics (identified as Gap #1). © XXXX American Chemical Society and Division of Chemical Education, Inc.



REVISED COURSE FORMAT AND STUDENT ASSESSMENT The revised course was designed to maintain the coverage of the principles and tools of green chemistry but also to address the four gaps mentioned in the previous section. The first and second sections are identical to the ones covered in the previous course. The course starts with a historical perspective of the field of green chemistry and covers the definition, the principles and tools of green chemistry, and sustainability. Students are asked to do daily research on specific topics in order to be actively involved in the discussion the following class period. The second section focuses on some of the applications of green chemistry and sustainability in our everyday life. A list of examples is provided to the students who

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focusing on making a chemical reaction or a commonly used product more environmentally friendly (Assignment #5 counting for 35% of overall grade). Miniproposals often target the polymer industry such as the use of a renewable source of isoprene that can be polymerized on a large scale using neodymium catalysts. The bioengineering industry was also reflected in a proposal titled “The grass is always greener ... engineering slow-growing grass to reduce mowing frequency” that focus on removing or rendering nonfunctional certain enzymes in the gibberellin biosynthesis pathway responsible for grass growth. Students have often looked at how to improve treatment plants as demonstrated in a project aimed at removing and reusing 17β-estradiol from wastewater. Each team presentation was 20 min long followed by 5 min of questions and comments. The guidelines for assignments 1−5 as well as the syllabus are presented in the Supporting Information.

pick a topic of interest and then search the literature to come up with an organized plan of discussion. Relying on their plan of discussion, students have 8−9 min to lead the in-class debate on the chosen topic that includes a presentation of the traditional vs greener approach, immediate and long-term impacts, and barriers to the new implementation (Assignment #1 counting for 15% of overall grade). To address Gap #1, a new section (third section) devoted to the introduction and application of green chemistry metrics (such as E-factor, percent atom economy, experimental atom economy, life cycle analysis) was developed. Specific organic chemistry reactions are studied from a green chemistry point of view. Students choose a chemical reaction previously covered in organic chemistry, such as an electrophilic aromatic substitution, a cycloaddition, or a Suzuki coupling reaction, and build assessment tables that address calculations of atom economy and experimental atom economy as well as the energy and auxiliary substances requirements. Students use their analytical/quantitative skills to compare a traditional process vs a greener process and draw their own conclusions (Assignment #2 counting for 15% of overall grade). Two lecture sessions of 50 min each were spent on this topic. Students who worked on the same type of organic chemistry reaction were grouped for the presentation. The fourth section was restructured to fill in Gap #2 and is based on the evaluation of the political, societal, and business drivers in the success of green chemistry products and processes. Designing greener technologies and green chemistry at work in companies such as DuPont and Dow Chemical are presented. Students are asked to study the evolution of a chemical or process in the petrochemical, bulk chemical, fine chemical, or pharmaceutical sector. They are expected to address the problem(s) with the traditionally used chemical or process, the cost to industry, the environment, and health, and the strengths and weaknesses of the greener product or process. They are asked to discuss the impacts of the outcomes on economics, production, and public image (Assignment #3 counting for 20% of overall grade). Students had 10 min to present their industrial case study. The fifth section is focused on green chemistry in less developed countries. This concept was briefly approached in the original course and is now extensively covered to respond to Gap#3. Students develop an advertisement brochure emphasizing green chemistry initiatives in less developed countries. Topics covered in the brochure are the magnitude of environmental challenges (e.g., production, pollution, toxicity) and their impacts on economics, health, and society in general. The students also address the key challenges (e.g., the role of governmental organizations, lack of training and infrastructure, lack of awareness, challenges in reducing the environmental footprint while sustaining a healthy growth rate) and the current strategic and governmental initiatives in place to support green chemistry and sustainability. Conclusions regarding the approach and sustainable model adopted by this country are drawn by the students (Assignment #4 counting for 15% of overall grade). Students had about 5 to 6 min to present their brochure. The sixth section is dedicated to the discussion of emerging topics in green chemistry and sustainability. This section existed, but it was revised to specifically include the role of toxicology in green chemistry in order to address Gap #4. The last and seventh section is unchanged and includes the creation and presentation of an innovation miniproposal



OUTCOMES AND STUDENT FEEDBACK In the revised course, green chemistry metrics (Gap #1) are presented and practiced in class (three class periods focus on green chemistry principles and applications to organic chemistry synthesis, and four class periods are devoted to green chemistry metrics). The expected outcome is for students to become efficient in assessing the “greenness” of chemical reactions using metrics parameters introduced in class. Completion of Assignment #2 with a grade of 80% reveals competency in the field of green chemistry metrics. The business component of green chemistry (Gap #2) is covered in class under designing greener technologies (three class periods) and industrial case studies (four class periods). The expected outcome is for students to understand the multiple factors affecting the evolution of a product. Completion of Assignment #3 with a grade of 80% reflects a fair understanding of the green decision-making process. The international aspect of green chemistry (Gap #3) is covered during three lecture periods and three class periods led by students. Students bring their own research to light, in the form of a trifold brochure, highlighting green chemistry initiatives around the world. The expected outcomes of Assignment #4 are to learn about key challenges in less developed countries, to understand the current strategic and governmental initiatives in place to support green chemistry and sustainability, and to design a concise brochure. The expected outcome of the incorporation of a lecture session about the role of toxicology in green chemistry (Gap #4) is to expose students to the field of toxicology and to increase awareness about how chemicals are evaluated for safety and sustainability. Recent student feedback about the revised course was highly encouraging. Students liked the presentations and discussions led by the class and spread throughout the semester in addition to the regular lectures. Students commented on the fact that the course was taught in an effective manner because it was a hands-on course. It allowed students to do their own research and therefore be very independent. Students also recognized the challenging aspect of the course and mentioned that it “was taught at the highest level possible” but also noticed that they applied much of what they learned in the class. The course was portrayed as highly demanding but fair with the assistance of the professor and requiring constant participation and critical thinking. Students enjoyed the course without a textbook. Most importantly students commented on the course as a confidence B

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(3) Prescott, S. Green Goggles: Designing and Teaching a General Chemistry Course to Nonmajors using a Green Chemistry Approach. J. Chem. Educ. 2013, 90 (4), 423−428. (4) Bastin, L. Lessons Learned Incorporating Sustainability and Green Chemistry/Engineering into a Non-Majors Course Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, March 21− 25, 2010, CHED-52. (5) Apelian, D. Empowering First Year Students by Immersion in a “Grand Challenges” Course on Sustainable Development. JOM 2010, 62 (4), 8−9. (6) Green Organic Chemistry in Lecture and Laboratory; edited by Dicks, A. P., Ed.; CRC Press: Boca Raton, FL, 2011; 283 pp. (7) Montes, I. Teaching Green Chemistry in the Organic Chemistry Course Abstracts of Papers, 236th ACS National Meeting, Philadelphia, PA, August 17−21, 2008, CHED-034. (8) Valdez, L.; Rozov, M.; Upmacis, R. K. Green Chemistry: Adaptation of experiments for a laboratory course Abstracts of Papers, 244th ACS National Meeting, Philadelphia, PA, August 19−23, 2012, CHED-190. (9) Schaber, P. M.; Larkin, J. E.; Pines, H. A.; Berchou, K.; Wierchowski, E.; Marconi, A.; Suriani, A. Supercritical Fluid Extraction versus Traditional Solvent Extraction of Caffeine from Tea Leaves: A Laboratory-Based Case Study for an Organic Chemistry Course. J. Chem. Educ. 2012, 89 (10), 1327−1330. (10) Bisol, T. B.; Marques, M. V.; Rossa, T. A.; Nascimento, M.; Sa, M. M. Synthesis of Epoxone from D-fructose. A didactic experiment for organic chemistry laboratory course focusing on Green Chemistry principles. Quim. Nova 2012, 35 (6), 1260−1263. (11) Lenoir, D.; Schramm, K. W.; Koenig, B. Use and Application of the New Internet Book, NOP, a New Practical Course for Sustainable Chemistry Applied To Organic Synthesis. Fresenius Environ. Bull. 2012, 21 (8b), 2316−2319. (12) Reed, S. M.; Hutchison, J. E. Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid. J. Chem. Educ. 2000, 77 (12), 1627−1629. (13) Goei, E. R. Synthesis of Polyhydroquinolines: Green Chemistry Guided-Inquiry Materials for the Sophomore Organic Chemistry Laboratory Course Miami University, Department of Chemistry and Biochemistry, Oxford, OH, Ph.D. dissertation, 2010. (14) Fujita, M. Green Chemistry Lab and Course for Undergraduate Chemistry Majors Abstracts, 61st Southeast Regional Meeting of the American Chemical Society, San Juan, Puerto Rico, October 21−24, 2009, SRM-489. (15) Henrie, S. A. Using Green Chemistry Laboratory Manuals in High School and Non-Science Majors Regular and Web-Based College Chemistry Courses Abstracts, 60st Southeast Regional Meeting of the American Chemical Society, Nashville, TN, November 12−15, 2008, SRM-248. (16) Montes, I.: Rivera, R. Fostering Green Chemistry through a Capstone Course Abstracts of Papers, 244th ACS National Meeting, Philadelphia, PA, August 19−23, 2012, CHED-53. (17) Zheng, K. L.; Bean, D. P.; Lou, H. H.; Ho, T. C.; Huang, Y. Education Modules for Teaching Sustainability in a Mass and Energy Balance Course. Chem. Eng. Educ. 2011, 45 (4), 265−275. (18) Blakley, C. G.; Kan, G.; Lehman, M.; Patrick, A.; Curry, A.; Ison, E. A.; Ison, A. Catalysis in Green Chemistry: An Advanced Laboratory Course for Undergraduates Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, March 21−25, 2010, CHED-598. (19) AwesomeMinds.com. Change your life. http://awesomeminds. com/quotes/anatole-france-quotes (accessed May 2014).

booster in terms of improving writing and presentation skills. The structure of the course was well perceived as students appreciated how the assignments had a progression and in the end all came together. This is a discussion-based and writing-intensive course, which allows students to improve their communication skills while gaining depth of knowledge regarding the green decisionmaking process and problem solving. The main questions associated with sustainability were covered as well as the quantitative aspect of green chemistry. The students evolved from being spectators to actors and finally to producers, and they accomplished this established goal by applying their knowledge of organic chemistry and green chemistry metrics to organic chemical synthesis. Students also gained an understanding of business drivers and increased their awareness of sustainable initiatives in less developed countries.



CONCLUSIONS In the revised course students became competent in the assessment of traditional vs greener products and processes using green chemistry metrics. They also improved their grasp on the role of toxicology in green chemistry. They captured the role of economic and social factors in the development of a new and possibly more environmentally friendly product. Lastly they virtually traveled around the world while expanding their international vision of green chemistry. In any academic environment the ultimate goal is to prepare students for the future. By opening students’ minds to green chemistry, the author believes in the following quote from Anatole France: “Awaken people’s curiosity. It is enough to open minds, do not overload them. Put there just a spark”.19 This revised course highlights the necessary tools to achieve this ultimate goal. As one student summarized the course, “Green chemistry wants you to think outside the box! You need to think before you do!”



ASSOCIATED CONTENT

S Supporting Information *

A tentative syllabus is provided as well as guidelines for the five assignments covered in this course. This material is available via the Internet at http://pubs.acs.org.



AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.



ACKNOWLEDGMENTS Previous students in Green and Sustainable Chemistry at Washington College are the driving forces behind these changes. I could not thank them enough for their constructive criticism.



REFERENCES

(1) Marteel-Parrish, A. E. Toward the Greening of Our Minds: A New Special Topics Course. J. Chem. Educ. 2007, 84, 245−247. (2) Gross, E. M. Green Chemistry and Sustainability: An Undergraduate Course for Science and Nonscience Majors. J. Chem. Educ. 2013, 90 (4), 429−431. C

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