Final Study Guide c 5/20/05



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Final Study Guide C 5/20/05

The final consist of two 100 point sections. The first section is basically a midterm which covers the last third of the class (since the last midterm). This study guide covers this information. The other 100 points on the test will be comprehensive from the first two exams. You should look back through the first 2 study guides.


Lecture 18: Low Molecular Weight Chemicals from Trees - Part III


  1. Tannins

    1. Why is this class of compounds named tannins?

    2. Where can you find tannins? (what plants, etc)

      1. Where do you find tannins in grapes? Why are they there?

    3. What is their function in plants?

      1. How do they affect different organisms?

    4. Can you list the commercial uses of tannins besides tanning?

      1. How long have tannins been used for tanning?

    5. How are tannins isolated from plant material?

    6. What are the supposed health benefits of tannins in a diet?

      1. Which are better for you, tannins or tannin like compounds?

        1. This question has to do with our discussion on why red wine is aged…..why it tastes better after aging.

        2. What is astringency? What does this have to do with tannins?

      2. What theory was presented in class on how tannins might help with clogging or the arteries?

  2. I presented you with 2 slides containing structures of chemicals that can contribute to the aromatic odor of some trees. These compounds are usually found in fairly small amounts in plants and therefore most are made synthetically for commercial applications.

    1. Salicylic acid, which was originally obtained from willow bark, has been used as a pain killer. What current pain killer is a derivative of this tree extractive?

      1. This pain killer is now commercially produced starting with a petroleum derivative. Why isn’t it produced from salicylic acid obtained from willow bark?

    2. Which of the these small molecules is sold as a flavor and can be manufactured from petroleum, lignin, or can be isolated directly from a plant?

    3. How would I go about isolating one of these small compounds from a plant in order to create a flavoring ingredient? (like vanilla extract)

      1. In this extract you just produced, how many different flavor chemicals will be present?

  3. Alkaloids are interesting chemicals because they are often sold commercially in the natural form isolated from plants. Two of these alkaloids, quinine and strychnine are presented. Do you know what these alkaloids are typically used for?

    1. I mentioned another 2 alkaloids that everyone had heard of…..do you remember what these were?

  4. Fats

    1. Fats are typically triglycerides consisting of long chain fatty acids hooked to what chemical?

    2. What types of plants have higher levels of fats? Where is the fat located in plants?

    3. What is the function of fat in plants?

    4. How are fats obtained from plant material?

    5. What is saponification?

      1. What are the products of this reaction?

    6. What is the difference between a saturated and an unsaturated fatty acid?

    7. How do fats react during Kraft pulping?

    8. How are fatty acids recovered from black liquor?

    9. Industrial uses of fatty acids

      1. Why are they used instead of petroleum based materials as lubricating oils in metal working?

      2. What laundry detergent was originally made from tall oil fatty acids?

      3. Do lacquers dry or cure?

  5. Sterols

    1. What are sterols used for in trees?

    2. What does the fact that sterols are fish narcotics have to do with the pulp and paper industry?

    3. Although it is possible to manufacture most sterol based pharmaceuticals from petroleum based chemicals, most start with natural sterols. Why is this?

    4. What is Benecol?

      1. What is it used for?

      2. The sistanol that is the active ingredient in Benecol is produced from Nordic Pine in Finland. Why don’t pulp mills in Washington produce this compound?


Lecture 19: Commercial Biopolymers


  1. Cellulose

    1. Cellulose is the most abundant organic polymer and also the largest selling polymer. What percentage of cellulose that is sold is sold into chemical applications (not paper)?

    2. Chemical cellulose is sold into many applications. Is most chemical cellulose modified or unmodified?

      1. Modification of cellulose changes the properties of cellulose so that it becomes more like a plastic (petroleum polymer). What groups on cellulose are modified and how many of these groups are present on each glucose molecule?

      2. How does the analogy about poorly cooked spaghetti relate to the fact that natural cellulose has different properties than plastic like modified cellulose?

    3. Rayon

      1. What is rayon?

        1. How is it made?

        2. What is dissolving pulp and how is it made?

      2. The demand for rayon is quite variable year to year. Why is this?

      3. What types of products does rayon compete with?

    4. Cellulose nitrate

      1. What type of material is produced if one of the hydroxyl groups on each glucose unit of cellulose is nitrated?

      2. How about if 2 hydroxyl groups are nitrated?

      3. How about all three?

    5. What is cellulose acetate used for?

    6. What does carboxymethyl cellulose have to do with cheap ice cream?

  2. Starch

    1. What is starch used for in plants?

    2. Is most starch water soluble or water insoluble?

    3. The largest use of isolated starch is in food applications (thickening, etc). Can you name 3 other commercial non food use of starch?

    4. Both starch and cellulose are polymers of glucose. What makes these 2 polymers different?

    5. Humans can use starch as a food source but not cellulose. Why is this?

  3. Hemicellulose type polymers

    1. These materials typically don't have large markets also they are sold into specialty markets. Can you name a couple of examples of these type of polymers (I know they are listed below but could you name them if I asked on June 12th).

    2. Pectins:

      1. There is a lot of this thickener used in various food applications. Pectin is most often isolated from citrus peels and apple pomace. There is quite a bit of pectin available at reasonable prices. Why is this?

    3. What are uses for alginates (from seaweed) and for Guar gum (plant exudates)?

      1. How can these products compete with petroleum based products/

  4. Chitin

    1. What is chitin and where is it produced?

    2. Relative to cellulose and lignin, how much chitin is there?

    3. Why have crab canneries supported research into the use of chitin?

  5. Protein

    1. Protein is a polymer made up of various amino acids. Enzymes are proteins. A certain amount of protein such as casein and soy protein find industrial uses.

      1. What did casein (milk protein) have to do with plywood? Why do you think that casein is not used in this application anymore?

      2. Gelatin is a protein isolated from animal cartilage. There are industrial non food uses for this material even though it is relatively expensive compared to petroleum based materials. Why then can gelatin be sold into these markets?

  6. Rubber

    1. Where does natural rubber come from (both the actual source and geographically)?

    2. Natural rubber was not a great product until Mr. Goodyear changed it through vulcanization. What is this process?

    3. What is the source of the largest percentage of rubber?

    4. Why is natural rubber still a viable product?


Discussion on Labels


  1. In this label we discussed the ingredients found in cleaning products and what makes up a tennis ball. I was hoping that it would be clear that many of the “SUPER SECRET NEW NEW NEW AND IMPROVED!!!!!!!” ingredients are not all that exciting and new. Most products have a few well known materials in them a large number of which come from petroleum. There are often chemicals from biomass in these products often to try to get the customer to buy the product.

  2. Comet

    1. What does the calcium carbonate do for this product?

    2. What is the calcium hypochlorite for?

  3. What is a MSDS? What are they used for?

  4. Many of these cleaning products contain anionic surfactants. This is a fancy name for soap. Why don’t they call these soap?

  5. Murphy’s oil soap contains “potassium soap of vegetable oil” as its number one ingredient. Why isn’t this listed on the label as “soap” or as an anionic surfactant?

  6. Pine Sol contains roughly 25% pine oil (terpenes). In the old days Pine Sol was pretty much all pine oil and it was a good cleaning agent. What has replaced the pine oil in Pine Sol and why was this done? Why not remove all the pine oil?



Lecture 20: Lignin


  1. Lignin is the second most abundant organic polymer. Vast amounts of this material are processed each year through pulping processes so it is available for use. Approximately how much lignin is processed each year?

    1. What is done with most of this lignin?

    2. How much is sold each year as a chemical product?

  2. Most of the lignin materials sold on the market are modified lignin products (modified by the pulping process). Why is lignin not sold as found in the tree?

    1. How are lignosulfonates different from lignin found in a tree?

      1. What chemical group is attached to the lignin

      2. Do lignosulfonates dissolve in water?

  3. Can you name 2 reasons why fermenting the sugars in lignosulfonates is a good thing?

    1. What is produced from this process besides better lignosulfonates?

  4. Lignin is either sold as a powder or as a very thick liquid (50-60% solids). Lignosulfonates are produced in the pulp mill as dilute liquids. Why is the majority of water removed before the product is sold? (I can think of at least 2 good reasons).

  5. Lignin as a dispersant

    1. Can you give a very general explanation of why lignosulfonates act as dispersants in concrete? (Think about students standing around in the front of the class).

    2. Lignosulfonates are used in concrete as dispersants so that less water is needed. Why is less water important for concrete?

      1. What 3 ingredients make up concrete?

      2. Does concrete set underwater?

      3. Besides dispersing concrete, what other important characteristic of concrete is affected by the addition of lignosulfonates?

    3. In gypsum wallboard manufacture, lignosulfonates are again used as a dispersant so that less water is needed in the manufacturing process. Why again is less water important? (it is not the same reason as concrete)

    4. What is the role of lignosulfonates in the process of dyeing cloth?

      1. Where are dye plants located and why are they located there?

      2. If lignin is used in the dyeing of cloth, why isn’t all cloth brown?

  6. Lignin as a binder

    1. Why does the EPA regulate road dust?

    2. What was used before lignosulfonates to reduce road dust? Why is this material no longer used?

    3. Why doesn’t it make sense environmentally to simply use water to keep down road dust?

    4. Besides reducing dust, what other benefit its there to the application of lignosulfonates to dirt roads?

    5. Why does shrimp feed need such a strong binder? Why won’t lignosulfonates work in this market?

      1. What is currently used as a shrimp binder and why isn’t allowed in the US?

  7. Oil Well products:

    1. Not discussed

  8. Why do people apply iron lignosulfonates to plants when they could simply add iron sulfate? Basically I am asking 2 questions here: Why do we need to add iron (or other trace metals) to plants and why do lignosulfonates help with this process?

  9. Why would anyone want to add iron lignosulfonates to the ocean?

    1. Can you describe what is the purpose of the addition of iron to the ocean and what role lignosulfonates play in this process?

  10. What 2 low molecular weight chemicals are produced directly from lignin?

    1. Which of these is the most important? Can you draw the structure?

  11. What in the world is pear flotation?

  12. Please check out slide 23 of this lecture and understand my points. The points made in this slide would make a very good short essay question.

Lecture 21: Plastics

  1. Are the starting materials for most plastics little or big molecules?

  2. Where do the starting materials from most plastics come from?

  3. Can you describe the major differences between thermoplastic resins and thermosetting resins?

    1. What is Tg? Why is it important?

    2. Polyethylene and polystyrene are what type of plastics?

    3. Epoxy resins are what type of plastic?

    4. What is the difference between a thermosetting resin and a thermoplastic resin in terms of how the monomers are linked together? I’m asking here whether you can describe in general terms how chemically these materials are different.

    5. Can thermosetting or thermoplastic resins be melted and reformed into new products?

  4. What do plasticizers do for plastics?

    1. Garden hoses and white plastic pipes are made of the same plastic. Why do they have significantly different physical properties?

  5. Reinforcements, colorants, and stabilizers are added to plastics to provide certain important properties. How do these materials (plus plasticizers) affect the recycling of plastic?

  6. I provided you with a list of 6 commonly used plastics that are used in a wide variety of different applications. Why is it that different plastics are needed? Why isn’t everything just made out of high density polyethylene?

  7. Are petroleum based plastics degraded by microorganisms?

  8. Why are companies putting money into the manufacture of bioplastics?

Lecture 22: Molecular Farming

  1. What is a transgenic plant?

    1. I don't expect you to understand the science of how genetic material is transferred from one organism to another but I expect you to understand that is what we are talking about. Taking genetic material (a trait....something we want) from one organism and putting it into another organism. An example would be taking the pest resistance of one plant and putting it another plant. This would make the second plant and its offspring pest resistant.

  2. Be prepared to discuss the benefits of transgenic plants (slide 9). You need to understand the various points on the slide; don't just memorize the list. Why is there such potential benefit to this technology?

    1. How is the formation of pest resistant plants through molecular farming, for example, good for the environment?

    2. How is the formation of a tree with lower lignin good for the paper industry? What is the downside of producing this type of tree?

  3. Slide 11 shows lists of the amount of some organic chemicals produced from biomass and some from petrochemicals. What to the amounts show you????

    1. How does the volume of chemicals produced through fermentation compare the amount obtained from fossil fuels?

  4. Does molecular farming make economic sense in all instances? (can you explain your answer?)

  5. Slide 13 is very important; I spent significant time on each bullet. You need to understand why each of these bullet points could be a problem. Why are many people opposed to the production of these types of plants?




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