Hydrocarbons, Fuels and Feedstocks
Module Overview
This module uses transportation fuels as the theme to connect the organic concepts of hydrocarbon structure, intramolecular forces and physical properties to green and sustainable chemistry. The importance of hydrocarbons in our economy is detailed by its sourcing from fossil fuels to its use in transportation to its ultimate fate as carbon dioxide. A systems approach is used to connect chemical feedstocks and their application as transportation fuels to global environments with an emphasis on defining boundaries and components, inputs and outputs.
This module is divided into five units that can be incorporated into the first half of an Organic I lecture course. Each unit consists of a 30-minute PowerPoint lecture and associated activities that can be used in a variety of ways depending on instructor preference. The UN SDGs are presented early to emphasize the importance of organic chemistry in helping solve these sustainability challenges. Subsequent units specifically focus on Goals 7 (Affordable and Clean Energy); 12 (Responsible Production and Consumption); and 13 (Climate Action). Specifically, gasoline and gasoline blends are used to demonstrate a practical application of organic/aqueous solubility. Hydrocarbon combustion is used to introduce general reaction concepts in ideal and applied systems. Green Chemistry principles provide the framework to discuss waste, toxicity and renewable feedstocks when different fuels are used. The pros and cons of different fuels and feedstocks are discussed in terms of the different systems of the engine, and the local and global environment with an emphasis on how people and the economy impact each of these systems.
Module Goal
Given a set of structurally diverse compounds used in transportation fuels, students will be able to interpret their structures and predict their intramolecular forces and solubilities. They will be able to take this knowledge and assess the application of these organic compounds in the transportation fuel industry. Using systems thinking and sustainability considerations, students will also compare the manufacturing processes of fuels and fuel additives derived from bio-based vs. petroleum sources. Finally, students will be able to discuss the pros and cons of specific compounds used in transportation fuels based on their greenness, the systems involved and impact on one or more UN Sustainability Goals.
Audience
First-semester organic chemistry undergraduates
Class Time Requirement
Approximately five 50-minute class periods
Module Authors
Jessica Tischler, University of Michigan-Flint; Amy Dounay, Colorado College
Module Summary
Assumed Prior Knowledge
Students should be able to demonstrate the following skills and concepts to successfully begin this module:
- Writing molecular formulas and naming compounds from formulas
- Unit conversion
- Stoichiometric calculations
- Greenhouse gases and global warming
Learning Objectives
Students will be able to:
- Provide examples of how organic chemistry could be used to address the UN SDGs.
- Define what hydrocarbons are, identify their structures and provide examples.
- Describe traditional fossil fuel feedstocks used by the chemical industry and their applications.
- Discuss the sustainability concerns associated with fossil fuel feedstocks.
- Assess the impacts of different fuel types on local communities and global climate.
- Classify and rank the polarity of organic molecules based on their structures and functional groups.
- Describe the Intramolecular Forces (IMF) that occur between organic molecules.
- Identify and rank the relative strength of IMF between organic molecules.
- Predict and rank solubility of organic molecules based on the intramolecular forces involved.
- Use the structure and physical properties of organic compounds to explain and predict their use in transportation fuel or fuel blends.
- Describe the components of the combustion reaction of hydrocarbons in systems with different boundaries.
- Define Green Chemistry in terms of its goals and principles.
- Describe the different feedstocks used for transportation fuels.
- Evaluate the pros and cons of different feedstocks used in transportation fuels based on the Green and sustainable principles of waste products, toxicity to human health and environmental toxicity within different systems.
Unit Overview
Unit 1: Organic Chemistry and Sustainability
1.1 | Introductory lecture (30–40 min in class). Slides are intended for the first week of class to introduce organic chemistry and its connection to carbon dioxide, climate and general concepts of sustainability. |
1.2 | Activity: “Organic Chemistry and You” (10 min in class). This activity is intended to follow the last slide of the lecture. It can be discussed in class or in small groups. The activity can be assigned as a group or individual assignment to be turned in immediately following discussion or during the next class period. |
Unit 2: Hydrocarbons and Feedstocks
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2.1 | Lecture slides (30–40 min). Slides are intended to be presented after bond-line drawing conventions and alkanes/hydrocarbon nomenclature have been introduced. The slides connect sustainability and hydrocarbons to fossil fuel sources and their application as fuels and chemical feedstocks. |
2.2 | Activity: “Hydrocarbons and Fuels” (20–30 min out of class). This activity is intended to be given following Lecture B.1. It could be done individually or as small groups in or out of class. Students use the EPA site to better understand how fossil fuels are used in their state. |
Unit 3: Physical Properties and Applications in Fuel Chemistry
3.1 | Lecture (30–40 min): Lecture slides are intended to review the concepts of polarity, intermolecular forces and solubility of organic compounds in water. This is connected to the concept of what properties are desired for fuel used in internal combustion engines. Octane rating is introduced as a way to measure the fuel properties. Fuel additives are introduced as a method of modifying the fuel’s properties. Students are asked to make connections to the past two units to determine what properties an “ideal” fuel should have. |
3.2 | Activity: "Comparing Alcohols for Transportation Fuels" (20–30 min). This worksheet can be completed during or after class, as an individual or group assignment. It is intended to connect the physical properties of simple alcohols to their practical application as fuels while considering green and sustainable concepts from the past units. |
3.3 | Exam Question (5–10 min): Assessment that can be used on an exam or quiz that asks students to interpret physical data and structure of diesel to biodiesel FAME’s. |
Unit 4: Combustion, Energy, and Systems
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4.1 | Lecture (30–40 min): This lecture takes a closer look at the energy generated from the combustion of organic molecules. Specifically, students compare how the structure of the molecule can change the energy density of the fuel. Systems thinking is used to examine the combustion reaction and connect it to global sustainability.
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Unit 5: Green Chemistry and Biofuels
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5.1 | Lecture (30–40 min): This lecture formally introduces Green Chemistry and connects the principles to the UN SDGs. Students review the use of transportation fuels using different boundaries and are asked to compare petroleum sources to several biofeedstocks used to produce bioethanol. |
5.2 | Activity: Feedstock Questions (45–60 min): These questions can be given to students in multiple ways. They can be individual test questions or given together as an out of class assignment. It is intended as an assessment of the overall module as it asks students to relate a compound’s structure and properties to its intended use. They are also asked to evaluate the greenness and sustainability of its use in society.
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Download Module
Hydrocarbons, Fuels and Feedstocks Includes:
- Module Overview Document
- Units 1-5
- Formative Assessments
- Summative Assessments
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About the Green Chemistry Module Project
The ACS Green Chemistry Instiute has partnered with chemistry instructors from over 45 institutions to develop green chemistry education resources for undergraduate students studying general and organic chemistry.
