Fun with Measurements and Molecules

Here are a couple of fun links for Friday.

First from Neatorama, a list of Fun and Unusual Units of Measurements

Some of these are just plain silly, but there are a few legitimate chemistry-related units too, including Avogadro's number, Scoville heat units, and alcohol proof.

And also by way of Neatorama, a link to some Molecules with Silly of Unusual Names

These are all actual molecules, although some of the names might be considered more like nick-names (i.e. not the systematic, or most commonly used common names.)

I rather like penguinone - a ketone that looks vaguely like a penguin.  I'll have to share it with my daughter who is currently fixated on Club Penguin.

Biodiesel from Coffee

I don't often think about fat in my coffee (unless you like to add cream to yours - I prefer not to dilute my coffee.) If you consider that a coffee bean is just a seed for the coffee tree, it's not so surprising. The growing plant needs food and fat is a pretty good source of calories. You can see for yourself what the fat content in coffee is: the USDA has an online database you can search for nutritional info. Do a search for coffee - I chose the listing for:

Coffee, brewed from grounds, prepared with tap water

For a one cup serving, there is about 50 mg of fat, most of which is listed as "18:1 c" which means there are 18 carbons and one double bond in the fatty acids present, with a cis double bond.  The common name for this fatty acid is oleic acid.

By way of Greg Ladens blog, I came across a paper describing how Biodiesel can be obtained from coffee grounds.  Greg's post discusses some of the more practical aspects - and possible problems - in coffee being an economically useful source of Biodiesel.  I want to talk about the chemistry involved.

Spent Coffee Grounds as a Versatile Source of Green Energy describes how Biodiesel can be obtained from used coffee grounds.  Specifically they got their used grounds from Starbucks, probably a good source.  According to the paper, the used coffee grounds yielded about 15% oil which compares favorably with the yields from soybean oil and palm oil.  

So just how to you get biodiesel from coffee grounds? Surprisingly you start the same way you would if you were brewing coffee. However instead of using water, they "brewed" the used grounds with an organic solvent which would dissolve any oils remaining in the grounds. They tried three different solvents: hexane, dichloromethane and ether.  In addition to the oils, they also obtained Free Fatty Acids (FFA's), which had to be removed before they could convert the oil to biodiesel.  Hexane extracted the least amount of FFA's, so that was the solvent they chose to use.

The grounds were separated from the solvent-and-oil mixture by filtering it - again, just like brewing coffee.  The solvent was evaporated and collected for re-use and the FFA's removed from the crude oil by extracting with water and base.  This effectively converts the FFA to soap which is water soluble and can be separated from the non-water-soluble oils.  The FFA's have to be removed for two reasons.  

1. FAA's are typically solids, or become solids at temperatures you might experience while driving.  Oleic acid has a melting point of 13-15 degrees C, that's about 57 degrees F.  Having your fuel become a solid in the fuel line or engine would probably be inconvenient.
   
2. The method they use to convert the crude oil into biodiesel would not work on FFA's.

You could use the straight oil to run a diesel engine without doing anything else.  In fact, Rudolf Diesel did experiment with vegetable oils in his engine. Usually, the straight vegetable oil is converted into the methyl (or ethyl) ester and this is what is meant by "biodiesel."  The main reason for this is that the methyl ester is less viscous and stays liquid at a lower temperature than the straight vegetable oil does.

Biological fats and oils are triglycerides, which consist of a molecule of glycerol and three fatty acid molecules joined together to form a single molecule that is a triple-ester.  In making biodiesel, a transesterification reaction replaces the glycerol triple-ester with three molecules of methyl ester.

As any organic chemistry student could tell you, the transesterification reaction needs a catalyst and both acid and base will work as the catalyst.  If they had used an acid as their catalyst, they would probably not have needed to remove the FAA's, because under acidic conditions the FFA's would also have been converted into the corresponding methyl esters.  Under basic conditions the FAA's become soap instead, which is even less useful in your engine than the straight FFA.

So why did they use base as the catalyst?  The reaction is faster with the basic catalyst than with the acid catalyst, see this paper for a comparison of the two catalysts.  There might be other practical reasons, too.  KOH is a solid and not volatile. Although the KOH dust is corrosive, it is probably more convenient to handle and spills could be swept up.  Sulfuric acid would be handled as a liquid, it produces corrosive vapors and any spills would much more trouble to clean up.

Cool Google tip:  Google will calculate unit conversions for you.  I got the melting point for oleic acid from Wikipedia, which gave the mp in celcius. While I use celsius all the time in the lab, I'm not so familiar with thinking about celsius in terms of weather forcasts, so I converted it to Fahrenheit.  And I didn't need to look up the tedious equation since Google can do the work for me.  In the google search box type: "14 degrees C in F"  without the quotes and hit return.  Google will reply with: "14 degrees Celsius = 57.2 degrees Fahrenheit"

Narasimharao Kondamudi, Susanta K. Mohapatra, Mano Misra (2008). Spent Coffee Grounds as a Versatile Source of Green Energy Journal of Agricultural and Food Chemistry, 56 (24), 11757-11760 DOI: 10.1021/jf802487s

Monastic Musings: How can I be failing? - Unskilled and Unaware of It

A while back I found this article over at Researchblogging.com

Monastic Musings: How can I be failing? - Unskilled and Unaware of It In this post, Edith osb writes:

I noticed a surprising phenomenon last semester. Several first-year college students were getting consistently low scores on chapter quizzes - and they did not seem the least bit bothered or concerned about it. They were similarly unperturbed about scores below 60% on the first exam. When they received their mid-semester grade report, though, two of them came to see me, astounded to get such low grades. Their surprise was, of course, surprising to me: how could they possibly think that they were doing well when their quiz and exam scores were in the 50% to 60% range? They claimed that they were unaware that they were doing so poorly, and were somewhat angry that I had not "told them sooner."

A few years ago I had a student come to see me after final grades had been turned in.  The student had failed the class and was in tears, "Is there anything I can do to improve my grade?"  I was stunned, and explained that it was too late. Final Exams were the week before and the semester was over.  I gave 4 midterm exams and a Final Exam, this student had failed every one of them.  How could you not realize that you were failing the class?  Each of those exams was a clue that the student needed to get help.

I have always felt that college students should be treated like responsible adults.  It is their job to pay attention to their grades and get help when they need it. But reading Edith's post, and the article that inspired it, I am reminded of how easy it is to fool yourself.  I was not a particularly good student as an undergrad, and I often reassured myself that I would do better on the next exam - this did not tend to happen.  Realizing that you need help is difficult, and asking for it can be even harder still.

But there may be something else at work in addition to rationalizing and avoiding things that are difficult or uncomfortable.  In "Unskilled and Unaware of It: How Difficulties in Recognizing One's Own Incompetence Lead to Inflated Self-Assessments," Kruger and Dunning are interested in how people judge their own abilities. They looked at four different studies where the subject was given a task to complete, and then asked to predict how well they did.  

All of the subjects in all four studies tended to rate their own performance as above average! (How can everyone be above average?)  The subjects with the lowest scores thought that they had done much better that they really did.  The subjects with the best scores still rated themselves as above average, but generally below their actual scores. From this, the authors conclude:

We propose that those with limited knowledge in a

domain suffer a dual burden: Not only do they reach mistaken

conclusions and make regrettable errors, but their incompetence

robs them of the ability to realize it.

In the case of chemistry students, for example, this means that the students who don't know what they are doing also don't realize that they don't know what they are doing.  It is almost impossibe to correct your mistakes if you don't realize that you are making mistakes in the first place.

Consider American Idol.  If you have ever seen any of the audition shows you can see this in action.  The really awful contestants usually have no idea how bad they are, not a clue.  And they don't understand why the judges don't give them a ticket to Hollywood.  In contrast, a lot of the really good singers are much better at judging themselves reliably.  They know they sing well, but don't tend to over-estimate their ability.  They are often much better singers than they think they are, and seem a little surprised when the judges like their performance enough for a ticket to the next round in Hollywood.

Back to Edith's post.  She and some of the commenters suggest that some High School students - for a number of reasons - may not get trustworthy feedback on their academic skills, and because of that are not able to tell good work from bad.  They haven't learned to tell the difference. Or don't realize that it matters.

I have tended to downplay letter grades during the semester  - many things affect a student's final grade and one bad exam score can be offset by the remaining exams, quizzes and laboratory grades. I can't really predict a student's grade until everything has been graded.  I have also worked from the assumption that the student can tell that a exam grade below 70% means a D, which is close to getting an E (my school doesn't give F's, maybe the letter E is a little less judgemental) and realize that unless they do something about it they will be disappointed with their final grade. 

I think I may change that practice and start putting letter grades on exams and quizzes to help the low performing students learn to recognize unambiguously that they are not doing as well as they would like. I highly recommend reading both Edith's post (and the comments) as well as the original paper itself.

Tom Petty Finds Some Ancient Tech

Been away for a while, so I thought I would post something fun.  What is all that weird stuff the band finds in the desert, all wrapped-up in plastic?  And aren't they watching Battlestar Galactica, too?

Blogging for Extra Credit

I don't normally give extra credit assignments in my classes.  I figure that rather than doing "extra" work, the class should focus on mastering the material we work on every day.  However, we have had a challenging semester and I wanted to give the class something fun to do that might help their morale (and grade)  and encourage them to read about science outside of class.  I asked them to write to me about something interesting that they had read about science, something from my blog or any thing else that strikes their fancy.  

It's always fun to see what students find interesting when they are left to choose the topic themselves.  Here is what I learned from my class:

Mikaela wrote:
Although my intentions were to look at one article and write about it, I seem to have got lost in the wonderful world of blogging and spent a little too much time on the day before exams surfing the web. Of the several I looked at, I enjoyed three in particular. First, I read about the study on caffeine versus napping. This was interesting to me because I am a firm believe of napping! I've never really been a caffeine person; I very rarely drink pop and maybe have a cup of coffee once a month. Caffeine does not really make me feel energized or more alert so I tend to just stay away from it. Napping, on the other hand, is probably the best part of my day. Although I don't nap as much as I'd like to, I always feel completely recharged and very alert once I wake up. I often nap before tests or quizzes instead of stressing and cramming minutes before because I do best when I am relaxed. After reading, I was curious to see the whole article and different experiments they did. 

The second article I read was on the glowing mushrooms. This was interesting to me because I like hearing about abnormal things that occur naturally. I love that nature has so many undiscovered features and that it encourages us to never stop exploring. 

The third article I liked was five reasons you should pick up a pencil and draw in "Getting Things Done in Academia." I have always found drawing as a release from all my other academics. I took four years in high school and it was my favorite part of the day because I got to unwind. I like the idea of linking art with sciences (particularly anatomy) because I think once you try sketching something, you look at the object your drawing in a different way than you ever thought you would. Noticing the small details makes the animal come alive, and that much more beautiful.

From Jenna:
I read through your blog and found a few interesting things. The first thing that stood out was on Mutagen, how drugs can be very effective, yet they can also have bad side effects. It is interesting that they can predict the toxicity of the compound before making it. Since I have started college, I have had many people ask me what courses I am taking. When they hear me say chemistry, they crinkle their noses and say "Yuck! I don't understand why anyone needs to take that! What good is that going to do to help you in the real world?" That's just it, many of them do not understand, or at least do not think about it. The first thing that comes to my mind is, "How do they think aspirin and other pain relievers came to work? Along with their cholesterol meds?" Since I began taking chemistry, especially organic, I have developed a deeper understanding of how chemicals work, and I think it is important to realize that chemists really do make an important impact on the world. Now, back to your blog, I agree with what you said about media portrayal. It seems every time you watch t.v. you see commercials for a new drug and they spend over half the commercial telling you all these horrible side effects it has. It's no wonder why so many people are afraid of chemistry. The media mostly portrays things like this involving chemistry, I think they don't portray the good things about it mostly because they are not well enough educated in chemistry to understand-most of them are biologists.

I also laughed about the high fructose corn syrup. Also, the brightly colored fruits and dark leafy green being defined as a fat. Even I know that's not true! I probably have my mother to thank for that!

I found an interesting article about Lions, Tigers, and DNA.  A scientist started studying feline leukemia in the 70's and found diseases. I find this interesting since I have worked for a few vets for the past 3 1/2 years and have done multiple feline leukemia tests on cats. These tests have been made possible because of scientists who have spent years studying it. I also find DNA and reproductive traits very interesting in animals. I hope to study animal genetics and reproduction more in depth when I go to vet school. The scientist also studied feline HIV to fine a gene that might help create immunization for people. This is another example of how scientists and veterinarians can to reasearch on animals to help understand and find treatments for people.  He also found genetic mishaps during migrations of felines, and he published his research in Science.

Amanda:
I found an interesting article about finding a new earth.  They have no real evidence but the star that they did find is one third of the mass of our sun, and when they first found the star there was a planet circling it and pulling the star at the speed of a jet plane.  Then they saw another planet rotating and it was pulling the star at the speed of a race car. After the most recent observations they found a third planet circling the star much more slowly, it rotated at the speed that a man could run!  I thought it was cool because they went on to say that the planet had a rocky content similar to ours. They also said that it is 15 million light years away, so the thought of a new planet is still far away, but really cool!  I think that we should try to keep our planet and restore it but the thought of other life forms is exciting.

Carla:
I was searching online for articles about Organic Chemistry and came across a very interesting one that might be of a little interest or just a fun fact to learn about for you.

As the article says, "A discovery by a NASA scientist of sugar and several related organic compounds in two carbonaceous meteorites provides the first evidence that another fundamental building block of life on Earth may have come from outer space."

How interesting is that, that a fundamental building block of our life could come from outer space! I guess in previous research, researchers found that meteorites have organic compounds found on earth, like amino acids and carboxylic acids. This information is helping researchers understand that there could have been organic materials on earth before life. If you want to read more about it, the website is http://www.sciencedaily.com/releases/2001/12/011221082306.htm

Brad:
I thought you all might like these topics… some relate strongly to organic chemistry and its affects and some deal with chemistry and physics and some are just plain interesting facts I thought you all might like to look into….so here is a list with links…

1. Is Carbon nanotubing… I first read about this material on an article that was titled “space Elevator” why it was call that is that the unique structure of this carbon sphere was a fraction the weight of steel and was around 10x the strength of steel, which made it a good candidate. http://www.personal.rdg.ac.uk/~scsharip/tubes.htm 

2. This topic is a little hard to find…. Saw this on the history channel which was kind of cool how Hannibal in around 220 b.c. conquered Rome by attacking them through the mountain range the Alps. What made this so unique was Hannibal was said to be crazy to attempt this by taking 10,000 people and horses and war elephants on this trial over the mountain. He had no problem scaling the mountain where he ran into trouble was the descent. He ran into steep limestone rock faces they could go down and they couldn’t turn around either. As they sat there his chemist as you might call them found out if you heat limestone up and pour in their day was wine vinegar it would react and produce CO2 and H2O. Once cooled the rock became very brittle and they were able to make a zig zag path down the mountain face. As for a link with this I have looked for the story and havent found one you may be able to look up on history.com and check for times the program maybe showing.

3. This topic is just rather interesting that relates to chemistry and slighty organic chemistry if you look up the term Browns Gas you will find an interesting topic. I heard about this at work they explained it to me in the simplest way as they thought it heated up any given material to the temperature at which it melts and does just that… I guess these links will explain it in more or more accurate detail. http://www.eagle-research.com/browngas/whatisbg/whatis.html http://en.wikipedia.org/wiki/Oxyhydrogen 

4. This topic is for anyone who wants to do some good with their computer and also get a viewing of a construction of a large carbon molecule from a simple core model. This is a program you can download called Folding@Home what it does is use your computer to fold organic molecules in an attempt to develop a molecule that can help them fight cancer. If you want to do this simply google the program name and go from there. It is a good way to view large organic molecules and how organized they are, I have had this program for a year I still run it to this day.

5. Well its not a big secret that there are more bio majors than chem majors so here is something interesting for bio majors. I don’t know if this relates to chem, but people tell me they have never heard this before so here ya go. There was these two Russians playing in a chess tournament Nikolai Titov and Vladimir Dobrynin and all of a sudden while Titov was in deep concentration on the board he screamed in pain and grabbed his temples and his head blew up like a fire cracker. Now I know you may think im pulling your chain but it’s a rare condition call HCE Hyper-Cerebral Electrosis. Now not getting into to great detail the gist of the story is not to think to hard or your head may blow up…Literally! …. If you want to read the article let me know and I will bring the book in.

Chemistry Gift List

I know that everyone wants to keep-up with their chemistry studies over the holidays, and just in time the Make Blog site has a list of chemistry supplies for your Christmas list. The have descriptions of chemistry sets, as well as other chemistry-related things.

They include several chemistry sets, books about home chemistry experiments and suppliers for glassware. I had a Skilcraft chemistry set as a kid, but I don't remember much about it except that if you mixed certain chemicals together they would change colors. It is said that chemistry kits used to be much more interesting before all of the dangerous chemicals were removed. For an idea of what a do-it-yourself chemist could do in the Old Days, read Uncle Tungsten by Oliver Sacks.  

I really got a kick out of seeing The Golden Book of Chemistry Experiments, published in the 1960's. It's a collector's item now, but you can follow a link to download a pdf of the original book for free. Be aware, the file is 28 mb. There's a lot of good stuff there that would be familiar to any chemistry student. I'm not sure I would recommend making chlorine gas at home, but a lot of the experiments look like fun. You have to bear in mind how times have changed when reading this book - the list of where to buy supplies in the back of the book is pretty entertaining. I don't think I have ever seen carbon tetrachloride or manganese dioxide at a hardware store, or potassium permanganate at the drug store.

Also be sure to check out the youtube video of chemicals at a party, it's at the bottom of the page.

MAKE: Blog: The Chemistry gift guide - Celebrating chemistry and inspiring the next generation of chemists!

Need a Quick Pick Me Up? Take a Nap.

The New York Times has a short article about a study that compared caffeine with taking a short nap before doing mental and physical skills.  As it turns out, the people who took caffeine felt more awake, but they didn't score any better.  In fact the caffeine group performed worse than nappers on all three types of task that were studied:  motor skill, perceptual task, and verbal task.

I really like my coffee, but it is no substitute for getting enough sleep, and even a short nap in the afternoon will do more good for you than just caffeine.

The research paper itself is available online.  You can read the abstract for free, but to read the full paper you need to be a subscriber, or you can pay for it for $31.50.

Vital Signs - Regimens - For the Best Pick-Me-Up, Lie Down - NYTimes.com

Hat tip: Lifehacker.com