Okay, So It's Been a Week and a Half Since I Last Posted

Okay, okay.... So it's been a week and a half since I suggested that my frequency of posting was going to return to normal. I've been so busy at work trying to solve another problem (which recently came to our attention) that I haven't even been keeping up with other chemistry blogs, which are often my inspiration for posts. I'm still getting up at 5 in the morning in order to work in the garden (it's the only time my wife allows me to do whatever I want), so I don't feel like staying up very late writing these things. And the Pistons are still in the playoffs, although that could end at any moment. Since I don't have anything new to post today, I'll just try to amuse you with my best sodium explosion story from grad school.

It was an organic analysis lab class and we were heating some unknown organic material with sodium for some reason. Organikers may remember why. Perhaps we were trying to convert NO2 groups to NH2, I'm too tired to look it up. Well, somebody failed to decompose the leftover sodium pellet in their testtube with ethanol, and so when they threw the products into the sink, the sodium exploded after sitting a few seconds in the bottom of the drain pipe. No big deal, really. We'd all heard explosions before, but when the TA walked back into the lab (he had been gone during the explosion), he started sniffing the air and asked if anything was burning. We could all smell the sodium in the air. We dutifully denied any knowledge of this and he let the matter drop. What made the incident memorable to me was that the bunsen burners throughout the lab were all bright yellow, a clear sign of the sodium in the air. In fact, the relative brightness of each burner throughout the room clearly identified which sink had been the site of the explosion. The TA never noticed.

It's Over!

No, not the blog. But the customer presentation which we've been spending all our time (including weekends) preparing. We gave the presentation today and it went well, including the chemistry part which required us to squeeze all the chemistry onto 5 slides. Needless to say, that was not easy at all. Anyway, I should now have time to start blogging again. I still have much to do in the garden, but until the weather starts warming up a little more, I'm afraid to actually plant anything since a sudden frost can still wipe everything out.

So start expecting this blog to come alive again!

Chemistry Before IUPAC

Things are still pretty busy around here. Next week, we should be completely finished with the big customer presentation, so I should have more time to devote to this blog.

I’ve been reading one of the books I picked up at the used bookstore several weeks ago titled “Creative Chemistry.” So far, it’s covered the invention of nitrate based explosives, the development of synthetic fertilizers, and the use of coal-tars to create a wide range of dyes. Since this book was written in 1919, there is a definite focus on World War I, as most of the chapters are devoted to describing how chemists in Germany and Britain were forced to invent new methods of creating nitrates, rubber, explosives, etc. during the war since the normal supply of these materials were being cut off by various blockades.

Due to the book’s age, the author often uses older names for some of the chemicals, like benzol for benzene and toluol for toluene. How quaint! Perhaps organikers already know what carbolic acid is, but I didn’t until I started reading this book. But thanks to the chapter on coal-tars, when an engineer asked me what carbolic acid was yesterday, I was able to answer “phenol” as if I’ve always known it. (Not sure where the engineer came up with “carbolic acid.” Apparently he was looking through some arcane list of liquids trying to find one with a certain boiling point.)

Who says you can’t learn anything from old books?

The First of Many Apologies

I would like to apologize for my lack of posting the last two weeks. My goal is to post 4-5 times a week, but lately I’ve had so many demands on my time that there simply isn’t enough left over for blogging. Back in the winter, when the kids were going to bed earlier and there wasn’t much else to do in the evening, it was easier to post on a regular basis. Now the kids have soccer, we’re doing some interior painting, and I have several projects which are sucking up all my available time. It’s not like I don’t have a backlog of things I want to post about, so I am going to make a better effort to post in a timely manner.

One of those projects which are sucking up my time is gardening. Regular readers of this blog will know that I am obsessed with colors and for that reason; I plant lots of flowers each year -- enough to drive my wife crazy. In the same way that wine connoisseurs look down upon most white wine drinkers, most “real” gardeners would consider me a novice, since I am only interested in maximizing the amount of color I can squeeze into a fixed parcel of land. “Real” gardeners worry about things like the shape and color of the foliage, the number of pastel colors, and proper color combinations. These things mean nothing to me. I judge the success of my garden by the number of traffic accidents in front of my house due to the intense color emanating from my yard. I don’t care how many awards a plant has won, if it’s not producing loads of bright colored flowers it’s useless to me and will quickly get thrown into the garbage.

I’m also not big on maintaining the garden, either. After the initial preparation, planting, fertilizing, and mulching – I’m done. I am a strong proponent of the survival-of-the-fittest school of thought. If a weed manages to prosper in my garden and it’s not blocking my view of the colors, I say “live and let live.” Unfortunately, my wife does have a running feud with weeds and takes their attempt to eke out an existence as a personal insult. As a result, I do have to spend some time monitoring her and making sure she doesn’t take out a patch of flowers in her zeal to destroy a single weed.

Anyway, I’m in the preparation and planning stage right now, so I’m going to have to work harder in order to keep this blog going for the next month.

Miscellaneous Sunday

Just two miscellaneous items tonight. First up is a report posted on Reuter’s science web site. According to the study, Drinking Dulls the Brain's Response to Threats. Well, duh! I would have thought that was already well known. Why else would I drink during long distance flights? Apparently the study is intended to demonstrate that people under the influence have difficulty picking up on the fact that other people are pissed at them. Perhaps, but I suspect that people who are drunk tend not to care when other people are getting pissed at them.

From the LA Times comes a story about low carbon foods. This seemed like a pretty restrictive diet until I released they were talking about low carbon footprint foods. For example, eating chicken results in less greenhouse emissions than eating beef. They try to take everything into account, including the methane emissions by the animal while it is living. One possible flaw here. I believe they stop calculating the greenhouse effects once you eat the food. What about afterwards? Do they consider the greenhouse gas emissions occurring after eating White Castle burgers? Seems like that could be a major factor in their calculations.

Pop Chemistry

In the seemingly never-ending series of reports on the health benefits/risks of coffee and soda, I see that drinking soda can weaken your bones. I’ve heard of this before, but this study appears to confirm it. There are basically 2 main theories about the cause. Theory 1 assumes that it’s the caffeine, since caffeine has been linked to a higher risk of osteoporosis. If so, then coffee drinkers have to worry about this too. Theory 2 suggests the phosphoric acid in soda reacts with and removes calcium from the body, which eventually results in its leeching from bones if you are not getting enough from your diet. Since I tend to snack on Tums, I’m probably in steady state with respect to my calcium. Actually I may be safe without the Tums since the article states: “The researchers didn't find an association between cola drinking and lower bone mass in men.” Woot!

I would like to propose a third mechanism for calcium removal. EDTA (ethylenediammine tetraacetic acid) is added to some sodas as a preservative. The ability of EDTA to wrap itself around metal centers would seem to make it a prime candidate for calcium removal. EDTA’s ability to tie up calcium ions is an essential part of the standard titrimetric analysis for calcium. In fact, EDTA should be able to chelate many of the metals inside our bodies provided the pH isn’t too low. So I admit to being pretty surprised the first time I saw EDTA listed as one of the ingredients in Mountain Dew back in the day. Why is EDTA added to soda in the first place? It’s there to prevent the formation of benzene, which was found to be formed by a reaction between sodium benzoate and ascorbic acid back in the late 90’s. Apparently, the reaction is catalyzed by transition metal ions such as Cu²⁺ and Fe²⁺ (usually supplied by the can) and the addition of EDTA to complex those metals solves the problem. Note: Not all sodas contain EDTA. In some cases the manufacturers just decided to remove the ascorbic acid instead.

Follow up: A little more research has revealed that the most common form of EDTA used is the disodium-calcium salt of EDTA. This means that the EDTA cannot be responsible for lowering the levels of calcium in the body. Damn, another personal theory down the drain.

The Value of Good Eyeware

When I first read this article discussing lab accidents, I couldn’t help but feel lucky that I have never been really hurt in the lab. I’ve only been involved in one serious accident – an accident which only occurred because of a momentary lapse in vigilance. I try to remember that incident every time I feel like taking a shortcut with regards to safety. Then I read this blog post which discusses the hazards of diazomethane and it reminded me so much of my “incident” that I decided to describe what happened.

I was preparing some molybdenum compound whose name I cannot recall using some reagents which I no longer remember. (The experiment was such a flop, I apparently never recorded the details anywhere) The only thing I recall is that one of the reagents was an organic azide (or something very similar). I knew about its tendency to explode and so I was very careful for 99.9% of the synthesis. I followed the prep to the letter, using inert atmosphere techniques, and dutifully wore my safety goggles throughout. After filtering the final product, which should have been very inert, I was disappointed to see only a thin layer of reddish brown material on the frit. I took the glassware apart and tried to get a closer look, but there was so little material left on the frit that seeing it was difficult with smudged goggles. Since the reaction was over and no one else was doing anything close to my bench, I foolishly removed my goggles for a better look. Bending down so that my eyes were level with the frit, about a foot or 2 away, I used a spatula to scrape the material away from the frit. The only warning was the appearance of a spark followed immediately by the detonation. Except for a minor abrasion to one of my corneas, I was totally unscathed. The glassware, however, was another story. The top 6 inches of the glass frit had been totally obliterated. No pieces were ever found, but the benchtop was covered with fine glass powder. To say I was lucky would be a huge understatement. I still don’t understand how I wasn’t blinded.

Since we’re on the topic of eye injuries, one of my former bosses was hit in the eye back when he was an organic grad student. He decided to take the bus over to a doctor to get it checked out. Apparently he had damaged the cornea, since the fluid in his eye was slowly leaking out. Ewwww! Not only was his vision in that eye getting blurry during the bus ride (which would have been freaking me out), but his fellow passengers were also treated to watching his eyeball slowly collapsing during the trip. That would have kept me off the bus for weeks.