Safety glasses are not optional!!!!

If there's one thing I do not compromise on, it's safety glasses. As soon as my students enter lab, they are required to don their safety glasses. After a few terse reminders early in the semester, they usually catch on and rarely need any reminders.

Through the course of my chemistry career, there have been a number of times I was thankful I was wearing safety glasses. Today was another.

In Organic Chemistry lab today, we were doing the oxidation of cyclohexanol to cyclohexanone using sodium hypochlorite (bleach) and then the oxidation of the ketone to adipic acid using nitric acid.


The nitric acid oxidation of cyclohexanone to adipic acid is done on a small scale. About 1 mL of concentrated nitric acid is used in the reaction. The ketone is added to the reaction, and it is heated in a sand bath for about a minute. One of my students was heating the reaction. She called me over to say it didn't seem to be reacting. The boiling chip was either floating on the surface or stuck to the wall of the tube. I tapped the reaction tube and the boiling chip sank. Suddenly, the reaction fired out of the tube like a 1 mL volcano. Some of the hot nitric acid flying through the air hit me in the face and on the arm. My student was hit on the hand. We both paused for a second and then went to the sink to wash off and neutralize any acid left with sodium bicarbonate.

Hindsight being 20/20, I realize now the sand was very hot and the reaction was probably superheated. The boiling chip sent the boiling into overdrive.

Having hot nitric acid land on bare skin feels like having an exacto knife stuck through to the subcutaneous tissue. It is unpleasant. My burgundy colored shirt was turning white in spots.

As for the safety glasses, if I wasn't wearing them, I am sure to have been in a real world of hurt. Who knows, from serious pain to blindness. I'm pretty sure hot concentrated nitric acid on the cornea is not going to do any good.

The good news is no one was seriously hurt.

The moral of the story safety glasses are NOT optional under any circumstance in a laboratory... even if you are a biochemist. Biochemists are, in my experience, the worst offenders of this policy.

UPDATE: No serious harm done. My face is in good shape. Surprisingly, only one yellowish spot formed and that was gone by today. No scars. I didn't shave today, because I didn't want to irritate the skin. My shirt survived an initial washing, but I'm not expecting it to survive too long. If experience serves me correctly, it's structural integrity has been compromised by the acid catalyzed hydrolysis of the beta-1,4-glycosidic linkages holding the glucose molecules together. Not to mention all of the other possible things boiling concentrated nitric acid can do.

Allow me to repeat the moral of the story. Safety glasses are not optional. I've had students complain about having to wear them when we weren't using anything dangerous. I tell them (and will continue to do so with renewed vigor) at that point it is not about the safety, it is about the habit. I am training my students to be habitual safety glasses wearers. You never know.

Bottling and a followup or two

Tonight I bottled my Anchor Steam clone. Before doing so, I checked the post I made about my Anchor Steam clone about 2 weeks ago and realized there were a couple of comments I had not addressed. Now, this is just a young blog (1 month old tomorrow) and I cannot allow reader comments to go unanswered.

First, the ubiquitous Milkshake wrote:

Anchor Brewery: their Liberty Ale is the most respectable from their entire offerings - the rest (including Anchor Steam) is unremarkable IMHO; I would rather have Brooklyn Lager over any of the Anchor stuff.

How do you emulate the steamy shallow vessel - that got the Anchor Steam its name - at home?

Also, if you happen to go to SF, they have tours and beer tasting, it is spiffy shiny brewery - museum like. Their copper brewing vessels are remarkably small for their throughput. The tour + tasting is free, you just have to call the brewery and make an appointment. The staff is very friendly and many of them have notable "beer bloom" red vasodilatation in their faces.

Thanks for the comment Milkshake. First, let me say... SEE, this is what I was talking about in my last post. Nothing other than Anchor Steam is available in MN. The only way to discover great beers is to tour the country. Everywhere I travel, I make it a point to discover local beers (this should be a post on its own). I've never had the chance to try anything else from the Anchor Brewery. I do not dispute your claim. I just have very little experience.

Emulating a brewing technique or environment is often difficult or impossible. The next best thing is to achieve the characteristic through other means (i.e. modification of ingredients). Sometimes, this works. Usually, it doesn't. But, my goal is to not make a perfect replica, but to use a clone as a starting point for my own recipes. Cloning just gets me closer to a taste I want.

I have been in SF and I am very ashamed to say I have not been to the brewery. I will slink away now.....

Moving on... An anonymous poster wrote:

A brew a week is a great way to start the year!

1) I assume you keg your brews... what's your setup like?

2) What's the best stout that you've brewed?

Cheers!

Let me respond to Mr. Anonymous. No, I sadly do not keg my beer. I dearly wish I did. I do however, expect to be doing so within the next year. I am building a bar in my basement and would be a fool not to. The best stout I have ever brewed is my Champion Cream Stout. It only took me a few tries to get it right, but I really like it. When I was a grad student in a state next to Iowa (I don't want to give away too many details) the fellow in charge of the NMRs was a bit of a rebel/renegade/enigmatic/genius, whatever you want to call him. After tasting a sample, he paid me to brew a batch of the cream stout. I did so and delivered it to his office. I assumed it would be taken to his home... nope. The entire 2 cases was consumed in our building. His disguise was to pour it into his coffee mug. Once the head was gone, it looked just like coffee.

Back to the Anchor Steam clone... I'm not sure if it will turn out as a match or not, but after tasting a sample before bottling, I know that this is going to be a very good beer. Now I have to wait a week before opening a bottle. I hate this part. The week usually ends up being 5 days.

Beer and geography

I live in southern Minnesota (USA). I love living here. I love the fact that a 120°F temperature range between summer and winter is normal. There are many other reasons why I love living here, but that isn't the point of this post. The point is to point out one of the things I really hate about living here. Beer distribution.

There must be some double secret embargo on the import of good beers into southern Minnesota. Sure, there are a few, but not enough. I just discovered Longshot from Samuel Adams. Longshot is six pack featuring three winners of a homebrew competition held by Sam Adams. This is fantastic and I was so excited to find it (more on this below). Then I realized, this competition has been around since 2001. I had never heard of it. The fact is, MN is not the first place they are going to distribute this beer, not by a longshot.

The bottom line is, MN beer drinkers are just too accustomed to the bland macrobrews of the mega brewers to demand better beers (in effective enough numbers, at least). Now, don't get me wrong, I do not dislike macrobrews. I drink plenty of them. I will never turn away a Bud or Miller or PBR or High Life. These are fine drinking beers, BUT THERE IS REALLY GOOD BEER OUT THERE!!!! Don't be afraid of it. A case in point:

The number one beer in Minnesota (or so the legend goes. I have no data to back this up) is Michelob Golden Light. Be honest, have any of you who living outside of MN or Iowa ever heard of Michelob Golden Light? Minnesotans cannot get enough of this stuff, and I will admit, I don't mind it. However, I believe the distribution area is primarily MN and Iowa. They stack this stuff to the ceilings in liquor stores.

Good beers will eventually find their way here. Moose Drool for example can be found in stores and on tap. Moose Drool is one of my favorite brown ales. It is from the Big Sky brewing company in Missoula, Montana. So, why is Moose Drool here and not other beers like, Mirror Pond Pale Ale from the Deschutes Brewery in Bend, Oregon or even Fat Tire from the New Belgium brewery in Fort Collins, Colorado? Well, when I lived in Montana, I noticed there were a LOT of transplanted Minnesotans in MT. I think MT is to MN what OR is to CA. The Minnesotans that came back to MN from MT begged for Moose Drool. And so, it is here. Only time and persistent requesting will improve the beer selection in southern MN.

My point of this post is that we are missing out on a lot of good beers that a lot of other people have access to. That does not mean we don't have good beer here in MN. There are in fact a few fantastic breweries in MN. Two of my favorites are the Summit Brewing Company in St. Paul and August Schell brewery in New Ulm. Summit makes my favorite pale ale. The Schell brewery is the nation's 2nd oldest family owned brewery, and they make great stuff. They also contract brew a lot of beers.

My solution to lack of access: brew my own. That's what I do.

As for the Longshot beers. I drank two of them (the Boysenberry wheat and the Dortmunder Style Export). Both were very good. I like the Dortmunder best. The maltiness and hopiness were superb. Bruce Stott, the fellow who made it, could deliver a case a week to my house and I would not complain.

Why we need scientists.

This is why we need scientists.

[Try this if the above link doesn't work.]

Bottling sucks and oxygen rocks!!!!

I hate the bottling part of homebrewing. But, until I can afford a kegging system, bottles it is. The best bottles to use are the returnable type. Returnable bottles are not as common these days, but they are still easy to find. The really "hard" part is having to buy the beer and empty the bottles. Oh my! What pains I must go through for my craft.

My beer of choice that comes in returnable bottles is Hauenstein. "Hauey" is a semi-local beer contract brewed by the fine folks at Schell's brewery. At $13 a case, the high quality bottles with beer are cheaper than buying empty bottles from a homebrew supply store. The beer isn't too bad. A typical American lager. Not exceptional, but $13 for a case of good bottles makes it worth it.

I bottled my Pilsner Urquell clone last night. As I've mentioned before, I sanitize my bottles in the dishwasher. That's a lot easier than washing them by hand. However, thanks to Chemistry, sanitizing is pretty easy.

There are a lot of sanitizing agents used in homebrewing. The cheapest and easiest to obtain is bleach (sodium hypochlorite, NaClO). However, using bleach requires a lot of rinsing. When sanitizing 50 bottles, excessive rinsing can get annoying. I prefer to use sodium percarbonate (a.k.a. One Step sanitizer). The sodium percarbonate (2Na₂CO₃•3H₂O₂ -sorry, I haven't figured out HTML subscripts yet [UPDATE: Got it. Thanks Ψ*Ψ.) releases hydrogen peroxide when dissolved in water. The H₂O₂ does its thing on the wee beasties, killing them dead. The byproducts are sodium carbonate (Na₂CO₃) water and oxygen. These don't have to be rinsed away. And that means more time for tasting.....

337 Calorie State of the Union Address

I did a little experiment tonight. I rode an exercise bike while watching the State of the Union Address to see how many Calories I could burn during the speech. I don't get political very often (I don't dislike politics, but I do tend to dislike politicians. They annoy me), but I do try to watch every State of the Union Address.

Anyways, I jumped on my recently purchased Schwinn 213 recumbent bike and started peddling. I set the bike program to "Pikes Peak." This wasn't such a good idea. The program starts out at "ahhh, what a nice ride" and over the course of an hour, ramps up the resistance to "kill me now!" Thankfully, Bush is no Clinton. A 90 minute address would have killed me. Bush's 50 minute address was just about right.

When all was said and done, the computer told me I had spent 337 Calories of energy (that's about 1400 kJ). From now on, this is how I will measure all State of the Union Addresses.

Butanedione

Butanedione, a.k.a. diacetyl, is a chemical occasionally found in beer. For most styles, it is undesired. For some styles, low levels are acceptable, but typically, high levels of butanedione (diacetyl) indicate something went wrong during the fermentation.



The first two reactions occur inside the yeast cell. They are catalyzed by yeast enzymes. The oxidation of the acetolactic acid to butanedione occurs after the acetolactic acid leaves the cell. Another fate of acetolactic acid is the formation of valine. Malt that contains high levels of valine favors the formation of more butandione.



The butanedione can be reabsorbed by the cell and enzymatically reduced to 2,3-butanediol. This usually occurs after 7-10 days, and diacetyl levels can noticeably decrease.

High levels of butanedione in the finished beer indicate either poor sanitation (which favor bacterial production of butanedione), too much oxygen, poor malt, or poor yeast.

Someday, I am going to find a procedure for the analysis of butandione. I will test all of my beer at various stages. Now all I need is the time....