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Alberta Chemistry 30

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Unit 5 - Organic Chemistry

Unit 6 - Chemical Energy

Unit 7 Electrochemistry

Unit 8 Chemical Equilibrium Focusing on Acid-Base Systems

Unit 5 - Organic Chemistry

Chapter 10 Hydrocarbon Derivations, Organic Reactions, and Petrochemicals

p. 64 Career Connection: Chemical Engineer

The chemical industry is Canada 's most knowledge-based industry. About 30% of workers in the chemical industry have university degrees. The salaries in the chemical industry are, as expected, among the highest in Canada .

Alberta Occupational Profiles

Search the Alberta Learning Information Site for "Chemical Engineer."

Native Access to Engineering Programme

This site features Aboriginal engineers and scientists. Click on "Types of Engineering" at the top of the screen, and select "Chemical Engineering."

p. 68 Section 10.1 Questions

2.   Create a graph of your choice to communicate the relative quantities of petrochemicals produced in Canada (Table 4). Follow the link below to update the data from Statistics Canada.

Table 4 Petrochemical Production in Canada , 2004

Petrochemical

Production (Mt)

benzene

  10

ethene (ethylene)

  57

1,3-butadiene

  3

butene (butylene)

  3

propene (propylene)

  11

methylbenzene (toluene)

  3

dimethyl benzenes (xylenes)

  4

phenylethene (styrene )

  9

Industry Canada-Petrochemicals Production

A chart gives the most recent data.

3.    Alberta has many industrial chemical plants spread throughout the province. Follow the Web link to Alberta Chemical Operations .

(a)   Find the chemical plants nearest to your home or school. List their names and (if possible) the chemical formulas for the products they make.

(b)   Find the use(s) for the chemicals you identified in (a).

Alberta Chemical Operations

Alberta's Chemical Industry

The Canadian Chemical Producers Association provides information on what is produced, where, throughout Canada .

Alberta, Canada ¾ Chemical and Petrochemical

The official Web site of Alberta Economic Development promotes all types of industries in the province, including the Chemical industry.

p. 71 Web Activity: Reactions of Hydrocarbons with Bromine

(Ignore the text on the Chemistry Education Web site; it is not relevant for the Web Activity.)

Pentane and 1-pentene are added to bromine dissolved in an inert solvent in the two dishes shown in this movie. Do these two hydrocarbons react in the same way? What is similar and what is different? Suggest a hypothesis to explain your observations.

Photochemical Bromination of an Alkane

This Web Activity requires Apple QuickTime. You may need to download QuickTime first, with your teacher's permission. Then click on Large QuickTime Movie. It will take a few seconds to download.

p. 76 Section 10.2 Questions

3.    Research examples of the use of organic chemistry to address health, safety, or environmental problems, and write a report or present one such case study. Examples of topics include leaded and unleaded gasoline, solvents in dry cleaning, aerosol propellants, and pesticides and fertilizers.

Green Chemistry

This pdf file contains a four-page overview of green chemistry.

Los Alamos National Lab-Green Chemistry

This site introduces green chemistry and outlines some of the successes by the Los Alamos Lab.

4.    Why was mustard gas such an effective weapon, both during the First World War and more recently? Research its properties and effects, and defences developed against it.

Mustard Gas

This researcher at Bristol University in England explains the composition and past use of mustard gas, and then goes on to explore the use of mustard gas as a therapeutic agent for cancer patients. The article also provides many links to other articles and websites that relate to mustard gas.

Mustard Gas: Toxicity Frequently Asked Questions
This list of frequently asked questions about mustard gas is provided by the Agency for Toxic Substances and Disease Registry. It provides lots of information, especially for someone who thinks they might have been exposed to mustard gas.

Mustard Gas Exposure and Long-Term Health Effects
The Department of Veteran Affairs provides this Fact Sheet regarding the long-term effects of mustard gas on war veterans.

5.    Why are some organic halides toxic while others are not? And why are some organisms affected more than others? Find out, using the following key words: bioaccumulation; fat soluble; food chain. Report on your findings in a short article for a popular science magazine or Web site.

University of Guelph-Bioaccumulation

This university site provides a definition of bioaccumulation, an outline of the process, and factors that affect the process.

Sample solution regarding DDT Bioaccumulation and Biomagnification
This Web site summarizes the manner in which pollutants enter an ecosystem, as well as their tendency to concentrate as they move through trophic levels. It provides case studies on DDT and the Long Island Estuary, and mentions various federal acts relating to heavy metal pollution.

Bioaccumulation
This Oregon State University site defines bioaccumulation, explains its process, and talks about the subject in terms of the dynamic equilibrium hat exists both within individual organisms, but also throughout an entire ecosystem.

Bioaccumulation Studies in Streams
This site provides links to the results of monitoring projects that keep track of certain bioaccumulation markers in certain streams across the United States .

Sediment Toxicity and Bioaccumulation Testing
Coastal Bioanalysts Incorporated is a company that performs bioaccumulation testing, and in this Web site they explain the various methods that they use to complete this testing.

6.    Shortly after the connection was made between the "hole" in the ozone layer and the release of chlorofluorocarbons, many manufacturers stopped using CFCs as propellants in aerosol cans.

(a)   Research what alternatives were developed, and the effectiveness of each in the marketplace. Are the alternatives still in use? Have any of them been found to cause problems?

(b)   Design a product (one that must be sprayed under pressure) and its packaging. Plan a marketing strategy that highlights the way in which your product is sprayed from the container.

Aerosols in the Stratosphere
This Web site provided by the United States Environmental Protection Agency (EPA) explores the link between aerosols in the stratosphere and ozone depletion. It not only provides useful graphs, but also several links to other EPA pages with information about ozone depletion.

Aerosol Propellants
This information page is provided by the Alliance for Responsible Atmospheric Policy. It explains the preponderance of aerosol products in consumer goods, and proposes that substituting HFCs into such products is the environmentally responsible solution.

Aerosol Propellants
This page is part of a series entitled "The Plain Man's Guide to Aerosols." It explains how aerosol propellant cans work, and introduces the various propellant liquids and gases that are used within them.

Energy and Global Warming Impacts of CFC Alternative Technologies

This lengthy paper outlines, with graphs, the impact of replacing CFCs with HFCs in Section 1.5: Major Findings.

Doctor's Guide ¾ CFC Alternative Causes Liver Disease

This short summary report of a medical case reported in the prestigious journal The Lancet urges a CFC replacement better than HCFCs.

8 .   Long-term replacements for CFCs and HCFCs include hydrofluorocarbons (HFCs), which have no chlorine atoms. HFCs are now being used in refrigerators, automobile air conditioners, aerosol cans, and as foaming agents.

(a)   Draw the structural formula for CH 2 FCF 3 (l) (also called HFC-134a).

(b)   Research the latest information on HFCs and on alternative chemicals or technologies that are being used in refrigerators and air conditioners. Present your findings in a brief report.

Environmental Health Perspectives

Read about the "Rock 'n' Roll" refrigerator, which uses a thermoacoustic design to replace traditional refrigerator coolants.

Greenfreeze: A Revolution in Domestic Refrigeration

This site discusses the use of butane and propane-Greenfreeze technology-in refrigerators.

Heating, Refrigeration and Air Conditioning Institute of Canada

The HRA institute outlines alternatives to HCFSs.

p. 84 Career Connection: Chemical Employees

According to Statistics Canada, the chemical industry in Alberta employs 8000 full-time people directly. Each job in the chemical industry creates 2.5 additional jobs in the local economy; e.g., engineers, scientists, technologists, and trades and support personnel.

Research a chemical career that you might be interested in at the Alberta Learning Information Service (ALIS) Web site. Report on the type and years of education required and the expected salary.

Alberta Learning Information Service

There are several ways of searching for careers. Try a number of them.

p. 86-87 Section 10.3 Questions

8.    Alcohols have gained increased popularity as an additive to gasoline, as a fuel for automobiles. "Gasohols" may contain up to 10% methanol and ethanol, and are considered more environmentally friendly than gasoline alone.

(a)   Write balanced chemical reactions for the complete combustion of methanol and ethanol.

(b)   Although methanol is less expensive to produce, ethanol is blended with methanol in gasoline because methanol does not mix well with gasoline, and ethanol is used as a co-solvent. Explain, with reference to molecular structure, why ethanol is more soluble than methanol in gasoline.

(c)   Methanol and ethanol are considered to be more environmentally friendly than gasoline. Research, and explain why.

(d)   When small amounts of water are present in the gasoline in the gas lines of a car, the water may freeze and block gasoline flow. Explain how using a gasohol would affect this problem.

Ethanol General Information
This site is maintained by the Alternative Fuels Data Center . It provides essential information on the potential use of ethanol as an energy source in transportation. It provides many links to the major industry players that recommend ethanol use in vehicles.

Ethanol Information
Hosted by the American Coalition for Ethanol, this site advocates the many benefits of blending ethanol with the currently used form of gasoline. It outlines the economic, agricultural, energy, and environmental benefits of making the change. Start by clicking on "All About Ethanol."

Global Climate Benefits of Methanol
This page hosted by the Methanol Institute briefly explores the climatic advantages that might result by the adoption of methanol as an energy source for vehicles. To access information on methanol fuel cells, click on "fuel cells" on the left of the page and then click on "fact sheets."

9.    Considering the technological difficulties and the economic cost of producing ethene, which of the following solutions would you choose? Justify your selection:

•  burn and/or export the natural gas without removing the ethane
•  remove the ethane and export it separately in a special pipeline
•  crack the ethane to ethene and export it by pipeline
•  use the ethene in Alberta to produce tertiary products, such as plastics

Ethene Production

This Web site discusses one way ethene is produced and outlines some of its uses.

Ethylene

Under "Production" are two methods of producing ethylene (or ethene): steam cracking and catalytic cracking.

10.    Radiator antifreeze and coolant is 1,2-ethanediol (ethylene glycol). Ethylene glycol is usually mixed 50:50 with water for use in the radiator. Large quantities of this chemical product are produced near Fort Saskatchewan and Scotford , Alberta . Ethene reacts with oxygen in one reactor to produce ethylene oxide (C 2 H 4 O(g)). The ethylene oxide then reacts with water in a second reactor to produce ethylene glycol.

(a)   Write displayed formula equations for these reactions.

(b)   Explain why ethylene glycol is a better choice as a radiator antifreeze and coolant than ethanol.

(c)   Explain why methanol, rather than ethylene glycol, is used as a windshield wiper antifreeze.

(d)   Which is more toxic, methanol or ethylene glycol?

(e)   Use a reference to find the freezing point of a 50:50 mixture of ethylene glycol and water.

MSDS ¾ Ethylene Glycol

This is an MSDS fact sheet for ethylene glycol, showing properties and toxicology.

MSDS ¾ Methanol

This is an MSDS fact sheet for methanol, showing properties and toxicology.

Freezing and Boiling Points of Antifreeze

In this article on how car cooling systems work there is a table showing the freezing and boiling points of the 50:50 mixture of ethylene glycol and water as well as a 70:30 mixture of ethylene glycol and water.

13 .   Research the progress of chemists and chemical engineers on ways to convert cellulose into ethanol. The results could mean a new market for Northern Alberta 's tree resources. Summarize your findings in a brief report.

Iogen Corporation ¾ Cellulose Ethanol

Iogen Corporation's Web site promotes the benefits of using agricultural biomass into ethanol.

Innovation Alberta

Transcript of Q&A with Dr. David Layzell, Founder and Research Director, BIOCAP Canada Foundation. Towards the end of the transcript Dr. Layzell talks about the prospects of this technology.

Creating Cellulosic Ethanol

This BioCycle article explains the differences and similarities between conventional ethanol and "cellulosic" ethanol.

p. 95-96 Section 10.4 Questions

10.    Tannic acid, originally obtained from the wood and bark of certain trees, has for centuries been used to "tan" leather. [O12, 68, 9]

(a)   Give the chemical formula for tannic acid.

(b)   What effect does tannic acid have on animal hides? Explain your answer with reference to the chemical reactions that take place.

Wikipedia ¾ Tannic Acid

Wikipedia provides a clear definition, describes sources, and links to further information.

MSDS ¾ Tannic Acid

A chemical supply company has an on-line MDSD for tannic acid.

Phytochemicals

Tannic acid is one of many phytochemicals ¾ chemicals that are derived from plants.

Leather Tanning
This site explains the origins of leather and the tanning process. The cleaning, depilation, sweating, liming processes, as well as the two methods of tanning are described.

p. 101 Web Activity: Recycling Plastics

Go to the Canadian Plastics Industry Association Web site and gather information to write a procedure for processing recycled plastic. Also collect some pros and cons from multiple perspectives concerning the use of plastics.

Canadian Plastics Industry Association

Understandably, this industry Web site tends to be on the "pro" side of the use of plastics.

The Plastics Recycling Process

This teaching package is produced by the Environment and Plastics Industry Council (EPIC) ¾ a council of the Canadian Plastics Industry Association (CPIA).

p. 102 Biology Connection: Correlation versus Cause and Effect

Many biochemistry studies related to food are correlational studies. These studies look for a correlation (relationship) between two variables (without being able to control all other variables-as a cause-effect study would). For example, scientists found a strong correlation between saturated fats (and transfats) and artery and heart diseases. Chemists responded with creative solutions ( Figure 7 ).

[Link to pdfs of pages from Nelson Biology Alberta 20-30 - to come (later!)]

Mayo Clinic

In this article a nutrition specialist gives her opinion on the butter versus margarine question.

Discovery Channel

From Discovery Health, this article provides the pros and cons of both butter and margarine.

p. 104 Web Activity: Natural Polymers

Investigate one natural polymer. Prepare a presentation, including text and graphics, to describe the use or importance of the natural polymer, the type of polymer, and the polymerization reaction. Choose one of rubber, silk, cellulose, starch, or DNA, or find your own example.

Wikipedia

The Wikipedia online encyclopedia site has entries for all the examples included in the activity.

The Rubber Association of Canada

This industry association Web site has pages on History, Recycling, and Safety.

The Silk Association of Great Britain

The various associations can provide helpful information on the importance of the example chosen as well as its history.

p. 104 Web Activity: Molecular Modelling

Molecular modelling has become more of a computer activity than a physical activity. Check out some of the molecular modelling Web sites.

Amino Acids

This site uses Jmol modelling software, which requires that Java applets are enabled on your browser.

Chemistry, Structures and 3D Molecules

Models of scores of compounds are provided on this site. You will need Java on your computer to view and interact with the models.

p.107 Explore an Issue: Natural or Artificial Polymers for Diapers?

CHEC's Healthehouse

This U.S. pro-environmental site gives what appears to be a balanced viewpoint on the diaper debate, and comes out in favour of cloth diapers. Make your own decision about the validity of their arguments.

The Great Disposable Diaper Debate

Taking a slightly wider viewpoint, this article quotes some diaper studies, but fails to draw a conclusion.

The Ecological Debate: Cloth vs. Disposable

Several articles are collected together, providing a range of viewpoints.

p. 109 Biology Connection: Glycogen

Animals also produce a starch-like substance, called glycogen, that performs an energy storage function. Glycogen is stored in the muscles as a ready source of energy, and also in the liver, where it helps to regulate blood glucose levels.

[Link to pdfs of pages from Nelson Biology Alberta 20-30 - to come (later!)]

Work and Energy in Muscles

At this site there is an explanation, using data from the 1964 Olympics, of why we have to run slower in order to run longer.

Glycogen Metabolism

At this University of Waterloo site there is information on glycogen metabolism as well as a figure of the structure of glycogen.

p.109 Mini Investigation: Starch and Cellulose

Use a molecular model kit and/or a computer program to construct molecular models of glucose, sucrose, starch, and cellulose.

Food Molecules

Scroll down to the Carbohydrates section to select the molecules you want.

Cellulose

The Virtual Chembook gives lots of information, as well as line structural diagrams.

p. 44 Biology Connection: Glycogen

Animals also produce a starch-like substance, called glycogen, that performs an energy storage function. Glycogen is stored in the muscles as a ready source of energy, and also in the liver, where it helps to regulate blood glucose levels.

Work and Energy in Muscles

At this site there is an explanation, using data from the 1964 Olympics, of why we have to run slower in order to run longer.

Glycogen Metabolism

At this University of Waterloo site there is information on glycogen metabolism as well as a figure of the structure of glycogen.

p. 109 Mini-Investigation: Starch and Cellulose

Use a molecular model kit and/or a computer program to construct molecular models of glucose, sucrose, starch, and cellulose.

Chemistry, Structures and 3D Molecules

Models of scores of compounds are provided on this site. You will need Java on your computer to view and interact with the models.

p. 110 Web Activity: Cellulose Acetate

This activity illustrates the extent of historical and current work done by polymer chemists to use natural polymers to produce synthetic polymers with desired characteristics and applications.

1.   What are some of the properties of cellulose acetates?

2.   What are some of the technological applications of cellulose acetates?

3.   What is a natural products chemist?

Biopolymers

What are biopolymers, and what problems may they help to solve? This Web site provides some answers, and includes links to related sites.

Cellulose Acetate1

Cellulose acetate was one of the earliest synthetic polymers, and is still widely used today.

Cellulose Acetate2

The Plastics Historical Society has a fascinating Web site, well worth browsing around.

Natural Products Chemistry

The Department of Industry and Resources of Western Australian provides a brief description of various branches of chemistry.

Chemical Ecology

The Proceedings of the National Academy of Sciences of the United States of America present an article about the future of the new field of chemical ecology. As the introduction states: "Chemical ecology is the product of a partnership between biologists and natural products chemists united by a shared vision and empowered by complementary skills."

p. 112 Section 10.5 Questions

19.    Raymond Lemieux, from Lac La Biche AB, was the first chemist to artificially synthesize sucrose (in 1953). Consult the biographical information of Lemieux. Describe his interest in science and one of his other accomplishments (other than the synthesis of sucrose).

Science.ca Profile

Raymond U. Lemieux

Both the above sites list the considerable accomplishments of this distinguished Canadian chemist.

20.   Natural rubber is made from resin produced by the rubber tree, Hevea brasiliensis .

(a)   Research the history of the use of rubber by Aboriginal peoples long before Europeans came to the Americas .

(b)   Research the commercial invention, production, and use of natural rubber, and the circumstances that stimulated the development of synthetic rubber.

(c)   Write a brief report on your findings.

Aboriginal Innovations-Rubber

This Lakehead University site includes an interesting science section with information on the history of rubber.

Everything You Ever Wanted to Know About Rubber

As the site name suggests, this site includes a lot information, including a brief history of Mesoamerican civilizations of Central America .

A Brief History of Rubber
From the Rubber Association of Canada, this site provides in chart form a timeline of major events relating to rubber and its past uses.

Charles Goodyear and the Strange Story of Rubber
Read about Charles Goodyear, the man credited with discovering the vulcanization of rubber.

21.    Find the latest research on saturated and unsaturated fats and transfats in processed foods.

Trans Fatty Acids and Coronary Heart Disease

The famous U.S. Harvard University provides a clear and well-presented explanation of what trans fats are, and what their effects are thought to be.

U.S. Food and Drug Administration

The well-known USFDA presents a page "to Provide Better Information to Consumers on Trans Fats."

Harvard School of Public Health ¾ Interpreting News on Diet

The example used on this site is the butter versus margarine question.

p. 119-125 Unit 5 Review

44.   Methane is produced naturally by a number of sources and becomes part of the hydrocarbon component in the atmosphere of Earth. Human technologies, such as dams, also contribute to atmospheric hydrocarbons. A typical value for atmospheric methane, as measured by an analytical chemist using a gas chromatograph, is 1650 ppb (by volume). [N]

(a)   Name four of the natural sources of atmospheric methane.

(b)   List two technological sources of atmospheric methane.

(c)   Methane is a greenhouse gas. What is a greenhouse gas?

(d)   List some other greenhouse gases and their sources.

(e)    What actions can you take to reduce the quantity of hydrocarbon molecules that you may allow to escape into the atmosphere?

Sources of Atmospheric Methane

Several sources of atmospheric methane are listed on this page from NASA.

Methane Emissions

This page details a specific source of atmospheric methane, rice fields, and the dilemma of needing more rice to feed the world population and the subsequent increase in methane emission.

55. The One-Tonne Challenge asks individuals to reduce their GHG emissions by one tonne. If there are 30 million people in Canada , how many tonnes of GHGs per capita are emitted from road transportation? (If possible, find a more accurate number for the Canadian population and/or total carbon-dioxide-equivalent emissions.)

Canada at a Glance, 2005

The Statistics Canada publication has many useful tables, including population statistics based on the 2001 census. A similar publication may become available after the 2006 census.

56.   Ethene has many uses, including the ripening of fruit and vegetables. List six examples of fruit and vegetables that you eat, along with ethylene production by the fruit or vegetable, and the ethylene sensitivity of the fruit or vegetable.

Ethylene Gas

Scroll down the page (a part of the mindfully.org Web site) to find the sensitivity chart.

57.   Describe the process of vacuum distillation in the refining of crude oil. Include the major types of products produced and the three types of high-vacuum units.

Vacuum Distillation

The Students' Guide to Refining has a page on vacuum distillation.

58.   Alberta has an extensive chemical industry that is the second-largest manufacturing industry in the province, producing about ten billion dollars' worth of products annually. List the four main segments of the Alberta chemical industry. Which one is the largest of the four? What is the main basis of this segment? Describe some employment opportunities in the Alberta petrochemical industry.

Alberta Canada ¾ Chemical & Petrochemical

The official Web site of Alberta Economic Development promotes all types of industries in the province, including the Chemical industry.

59.   BP Amoco has a linear alpha olefin (LAO) plant in Joffre AB that is producing 250 kt of LAO annually. What are LAOs ? Write the IUPAC name and draw the displayed formula for a few simple LAOs . Describe some major applications for small, medium, and large LAOs . [N]

Alpha Olefins

The Nexant site provides a wealth of details on this branch of chemical technology.

Chevron Phillips

This industry Web site has a glossary of terms, with brief descriptions.

60.   Research matters. Research is at the heart of all advances and innovations in science and engineering. Search the Internet for information on E10 and E85 ethanol blends, oxydiesel, and/or P-series fuels to gain an understanding of the current research programs involving gasohols. [N]

Alternative Fuels

This Canadian site includes several relevant links for research.

Natural Resources Canada ¾ Vehicle Fuels

Information is provided on just about any alternative fuel you could imagine.

Fact Sheet ¾ Low-Level Ethanol Fuel Blends

This U.S. Department of Energy-sponsored publication gives lots on information on fuels containing low percentages of enthanol.

Alternative Fuels ¾ P-Series

The "P" stands for pentanes. This informative Web site is also part of the U.S. Department of Energy.

62.   Summarize the arguments for private versus public ownership of oil and gas reserves below the ground in Alberta . What is the situation in most countries? In the U.S. ? In Canada ? Describe three ways in which the petroleum and natural gas ownership in Alberta is unique.

Privately Held Subsurface Hydrocarbons

The Freehold Owners Association produces information for landowners about their rights (or lack of rights) concerning the minerals in and under their land.

63.   Treated lumber (for building structures such as decks) contains two organic halides: pentachlorophenol (PCP) and 2,3,4,6-tetrachlorophenol. These organic halides are pesticides that are used as a herbicide (to eliminate plants), an insecticide (to control insects), a fungicide (to preserve wood and seed), and a molluscicide (to control snails). [N]

(a)   Draw line-structural formulas for these two organic halides. Their parent compound is phenol, C 6 H 5 OH(l).

(b)   Chemists warn against burning treated wood. They have gathered evidence to suggest that, when heated, two molecules of PCP can react to produce two molecules of HCl and one other molecule in the potentially toxic dioxin family of chemicals. Write a structural formula equation to deduce this chemical reaction. Include a structure for the new molecule formed.

(c)   Report on the structures of PCBs and dioxins. Are all molecules in these families of organic halides toxic?

GreenFacts ¾ Dioxin

GreenFacts is based in Brussels , Belgium . This page gives explanations/descriptions with three levels of complexity.

Wikipedia ¾ Dioxin

Wikipedia provides a definition, a diagram, and links to further information.

PCBs and Dioxin May Cause Diabetes

An activist organization in Wisconsin presents the case for a possible link between PCBs and dioxins and diabetes. If you go to the home page you will find a link to PCB Chemistry, Sources and Laws. Remember, though, that this is not a refereed source of information.

PCBs

At this site, produced by the Global Programme of Action for the Protection of the Marine Environment from Land-Based Activities, there is a link to PCB chemical structure and some brief details.

64. Report on the structures of PCBs and dioxins. Are all molecules in these families of organic halides toxic?

Texas A&M Toxicologist Studying Dioxin's Anticancer Effects

While he doesn't argue that dioxin is nontoxic, this researcher proposes that certain dioxins may have certain beneficial effects.

PCBs

GreenFacts.org describes two classes of PCBs: toxic and nontoxic.