Oregon State University
Department of Chemistry
CH 692: “Environmental Transformations of Organic Compounds”
Spring 2003
Instructor: Dr. Staci Simonich, 1141 ALS, phone: 737-9194, email: staci.simonich@orst.edu
Prerequisites: CH 336 and CH 440 or instructor consent
Time and Location: MWF 11:00 – 11:50, WB205
Instructional Objectives: The intent of the course is to cover environmentally relevant chemical, photochemical, and biological transformation reactions of organic compounds and to introduce students to test methods and predictive models that can be used to determine the persistence of these compounds in the environment. Agricultural pesticides and industrial chemicals in current use will be used as case studies.
Student Learning Outcomes: Students completing the course should be able to: 1) identify the environmental compartments that are relevant for assessing transformation reactions; 2) identify potential transformation reactions, assess their relative importance, and suggest tests to conduct to determine the kinetics of these reactions; and 3) evaluate the environmental persistence of a current use chemical and suggest changes in chemical structure or release to the environment that would decrease environmental persistence.
Learning Resources: Environmental Organic Chemistry, Schwarzenbach, Gschwend, and Imboden, second edition (2002), with other supplemental texts, journal articles and models as needed. If students have already purchased the first edition text, they are not expected to purchase the second edition text and the second edition text will be on reserve at the Valley Library. However, students who have not purchased the first edition are expected to purchase the second edition text. OECD Guidelines for the Testing of Chemicals and scientific literature will be used to discuss the experimental methods used to measure transformation reaction rates of organic chemicals. A copy of these Guidelines will be available in the Valley Library. Students will be required to understand, interpret, and present to the class current scientific literature as case studies on evaluating the persistence of organic compounds (this includes articles from the ACS journals Environmental Science and Technology and Journal of Agricultural and Food Chemistry). Students will also be required to access and use a multi-media environmental fate model and a quantitative structure activity relationship (QSAR) model for predicting physical-chemical properties from the worldwide web.
Assessment of Student Performance: Student performance will be evaluated through two homework assignments (total 40% of grade), a mid-term exam (30% of grade), and a group project of a case study on the evaluation of chemical persistence that includes a written report and a presentation to the class (30% of grade). The students will be allowed to use all published resources available to them to complete the homework, mid-term exam, and group project. However, the students may not work with other students to complete the homework and mid-term exam.
Course Syllabus:
Week |
Topics and Resources |
|
1 |
Introduction to the evaluation of chemical environmental persistence and criteria used for assessing chemical persistence – “Evaluating Environmental Persistence”; Webster, Mackay, and Wania Environ. Tox. Chem. 1998, 17, 2148-2158 Review of physical-chemical properties (vapor pressure, water solubility, air-organic partitioning, air-water partitioning, organic liquid-water partitioning) and experimental methods used for measuring these properties - Environmental Organic Chemistry, Chapters 4-7 and OECD and USEPA Test Guidelines |
|
2 |
Physical-chemical property estimation methods – Environmental Organic Chemistry, Chapters 4-7, Handbook of Property Estimation Methods for Chemicals, and download and use USEPA EPI Suite Quantitative Structure Activity Relationship (QSAR) model Sorption processes involving organic matter, experimental methods for measuring sorption, and QSARs - Environmental Organic Chemistry, Chapter 9, OECD and USEPA Guidelines for measuring sorption, and Handbook of Property Estimation Methods for Chemicals. |
|
3 |
Sorption Continued Thermodynamics and kinetics of transformation reactions - Environmental Organic Chemistry, Chapter 12 Homework Assignment 1 |
|
4 |
Fugacity and multi-media environmental fate models - Environmental Organic Chemistry, Chapter 3, “Finding Fugacity Feasible”; Mackay Environ. Sci. Technol. 1979, 13, 1218-1223, “Evaluating the Environmental Fate of a Variety of Types of Chemicals Using the EQC Model”; Mackay, Di Guardo, Patterson, Cowan Environ. Tox. Chem. 1996, 15, 1627-1637, and download and use of the Equilibrium Criterion (EQC) multi-media environmental fate model. |
|
5 |
Mid-Term Exam Hydrolysis and reactions involving other nucleophilic species - Environmental Organic Chemistry, Chapter 13 and OECD Guidelines for measuring hydrolysis. |
|
6 |
Redox Reactions - Environmental Organic Chemistry, Chapter 14 |
|
7 |
Direct Photolysis - Environmental Organic Chemistry, Chapter 15 and OECD Test Guidelines for measuring direct photolysis. |
|
8 |
Indirect Photolysis - Environmental Organic Chemistry, Chapter 16 and OECD Test Guidelines for measuring indirect photolysis. Homework Assignment 2 |
|
9 |
Biological Transformations - Environmental Organic Chemistry, Chapter 17 and OECD Test Guidelines for measuring biodegradation |
|
10&11 |
Group presentations of case studies and written reports due |