On Jargon

While reading Gary Stix's interview with Breaking Bad scientific advisor Prof. Donna Nelson, I stumbled upon a very telling chunk of text (emphasis mine):

"...the reduction step [for methamphetamine production] can vary from one synthesis to another, and there's a lot of differences in the reducing agents. And so I said, I don't know what reagent you want. They said to send them a list, and they liked the one that was aluminum-mercury because it would be easier for the actors to say those words.

That's another example of where I let [the producers] be boss. I wouldn't go back to them and suggest another reagent because it might be safer, cheaper, or have a higher yield. I just said, 'yes, sir.'"

"Sodium cyanoborohydride? No way am I saying that!"
Credit: AMC

Food for thought, especially for those of us trying to package chemistry in a more palatable format for folks outside the lab. But, the more I scratched my head over this situation, the more I wondered...are reducing agents that tough to pronounce?

Over at xkcd, Randall Munroe cheekily trounced our current cultural fixation on trochees, spoken words with a two-syllable stressed / unstressed pattern (ninja, pizza, Wal-Mart, Ke$ha, Xbox, etc.). "Aluminum-mercury," though taken right from the periodic table, hardly rolls off the tongue: seven* syllables!

"Classic" reagents for the reaction in question, like sodium cyanoborohydride (10 syllables) or sodium tris-acetoxyborohydride (12) certainly won't get by the writers without a grumble. But what about formic acid (4, with two trochees)? Raney nickel (4, two trochees) should also pass muster. Even better, maybe you could just fold the first two reductants into the generic "borane" (2, trochee) category?

Hey, AMC: Let's do lunch.

*And, of course, 8 if you live in the UK, and add that extra "i" to aluminium!

#ChemMovieCarnival: Act Three

Click here for Part 1 and Part 2

The directors are directing, the editors editing, the key grips gripping, supporting actors supporting, and the best boy...well, whatever he does, he's doing!

17. John of It's the Rheo Thing recaps the extra-fun chemical err....duplicity, in a movie by the same name. Honestly, this might be the first silicone-meets-Hollywood post that doesn't revolve around typical body modifications (it's a hair gel, folks). Bonus points for an accurate assessment of acting talents.
Film: Duplicity

18. For a post where she's (allegedly) avoiding discussing chemistry (or physics!), Renee really captures the teen angst vs. science teacher influence angle. Not to dis Jena Malone, but antiseptics are more than just fancy soap.
Film: Donnie Darko

19. Chemically Cultured primes our minds to the existence of hardtofindium, dalekanium, dilithium, and the new vogue fake element, unobtainum. Tom, I'd really like a copy of that poster!
Films: Avatar, Star Trek, Star Wars, The Core

20. Smells like three things in this post: burning thermite, methylamine, and the start of #RealTimeChem week! At Chemistry Blog, Mark lets the sparks fly, but doesn't seem to have perfected Walter White's lock-picking technique yet.
TV Show: Breaking Bad

21. New blog alert! Tien, of Must Love Science, covers the *cough* physics *cough* of a well-loved SciFi epic. Simulated gravity? There must be an extra-large chunk of dark matter outside each ship, no?
TV Show: Battlestar Galactica

22. Next, another Chemistry Blog stalwart discusses chemistry moments cropping up in his favorite crime drama. Azmanam's doppelganger (Dr. Spencer Reid) encounters some interesting cases, like that one where the bad guy dunks his victims in methanol to preserve their scent. (Bleargh!).
Also, plywood!
TV Show: Criminal Minds

23. Curt wrote this excellent entry, and he writes a pretty good blog, too: Minglingken, Mixing Knowledge. In this post, we have Russell Crowe, a good-guy whistleblowing biochemist, up against the wall of Big Tobacco. I never knew coumarin was used in cigarettes...
Movie: The Insider

Honorable Mentions: Vittorio and Gavin Armstrong sent along these "science-y" pictures from various forensic TV shows:

Assuredly not poly(vinyl acetate)
Show: Dexter

Hey, look, it's nitrogen! At least it's not chicken soup this time...
Show: NCIS

Want to play along? There's still time! Email me at seearroh_AT_gmail, or tweet (@seearroh)

Update 4/22/13 - Added minglingken entry; assigned authorship to Curt (thanks!)

Mo' Money, Mo' Quandaries

This may be the best indirectly-chemistry-inspired video this week:

Thanks, Stephen Colbert!

Methylamine Pseudoscience

Please see updates, posted below original piece. Thanks!

Pseudoscience strikes again. About a month ago, over at Slate's Brow Beat culture blog, Mr. Daniel Lametti - he of 'Ph.D.-Waste-Of-Time' fame - wrote a piece analyzing a recurring Breaking Bad plot device: the theft of large quantities of methylamine for the characters' illegal methamphetamine operation. The meat of the post:

"As a post on Reddit asks, since Walt is a brilliant chemist, couldn’t he just synthesize the stuff himself?

Yes, and pretty easily. There are many different ways to make the compound; with little more than an introductory organic chemistry class, you could probably synthesize it in your kitchen sink. (Brow Beat doesn’t recommend trying to make methylamine in your kitchen sink). Chemically speaking, methylamine is just ammonia with one hydrogen atom swapped out for a methyl group—a carbon atom and three hydrogen atoms. Without getting into too much detail, an easy way to achieve this swap* is to “bubble” ammonia (a gas) through methanol (a liquid) that’s been laced with a dehydrating agent like Silica gel. You could probably buy these chemicals at Home Depot and CVS. Silica gel packets are often packaged with new shoes and electronics to keep them dry."

Wait, huh? Let's start from No.

As a practicing synthetic organic chemist, I agree with the statement that silica gel dehydrates solvents by water absorption. Sure. But I've heated plenty of alcohols in the presence of silica gel, and 99% of them don't spontaneously lose water! (That would be a rocking olefin synthesis, if it worked...)

Methylamine: Easy as hooking up five pressurized reactors in your kitchen sink.
Credit: Albermarle

Let's put this on firm scientific ground. The reaction in question, a nucleophilic substitution, could theoretically occur by two mechanisms: S_N1, where the -OH group of methanol dislodges to form a methyl cation (?!?!), followed by subsequent ammonia bonding; or S_N2, where the ammonia directly displaces the -OH, one step, no intermediates.

In this scenario, both are extremely unlikely, especially at room temperature and pressure.

Now let's talk practicality: which company will sell you a cylinder of ammonia gas for 'home use?' (Not Home Depot). How will you get your methanol? What's the plan to isolate the (volatile, stinky) methylamine from the complex mixture of compounds this theoretical reaction produces?

Well, how do companies make methylamine? Albemarle technical documents to the rescue! Seems that mixing methanol and excess ammonia at 300-500 degrees Celsius, under pressure, over a zeolite catalyst will produce an equilibrium mixture of methylamine, dimethylamine, and trimethylamine (favored). After fractional distillation, the trimethylamine can be streamed over an amorphous silica / alumina catalyst to disproportionate it back into methylamine.

Not a kitchen sink in sight.

Update, 8/17/13 - This piece jumped back into the spotlight as Breaking Bad winds down its 5-season run. Thanks to Dylan at WaPo's Wonkblog for linking back here.

Commenters have taken issue with my description of the reaction, so I've slightly changed the text for clarity (methods / mechanisms, "forms" cations, oxidation...)

8/19/13 - Arguments have cropped up, in multiple forums, about reagent availability, feasibility of the chemistry at small-scale, mechanism, purification, etc. I blame myself for not refining my argument well enough in the original post. Very directly, I'll re-state the major arguments:

1) The silica gel + methanol + ammonia route will not produce methylamine as stated
2) Although an experienced chemist *could* produce methylamine using different reactions in a kitchen sink, he will by no means produce enough to support a burgeoning criminal enterprise which manufactures methamphetamine at multi-kilo scale.

*Curious - Appended at the bottom of the essay is a thanks for Prof. Adam Braunschweig, faculty at NYU now UMiami.. To what extent did Prof. Braunschweig proofread this post? Did he sign off on the "kitchen sink silica gel" concept in the middle? I can't possibly imagine that he thoroughly vetted this essay.

The Simpsons: Just Like "Cooking"

Ever have that feeling like you somehow missed the boat? 

Back in 2011, TV sitcom stalwart The Simpsons aired Episode #491 (NABF20), entitled "The Food Wife." I caught it in reruns for the first time tonight. Aside from the hilarious send-ups of celebrity chefs and uptown foodies, the episode turned a truly dark corner when it compared molecular gastronomy to...cooking methamphetamine. 

Really, it's true - Gothamist and Esquire both scribed pieces about the show last year.

Credit: Simpsons Wikia | 20th Century Fox

Breaking Bad gives its swan song later this year. We know Walter and Jesse's lab work has truly permeated pop culture when references pop up on prime time comedy cartoon shows.

And how often do you get to see Homer Simpson stumble around a garage lab*? Priceless.

*(Even one that doesn't make any practical sense; are those goofy cones supposed to be filters? And why do TV writers always think we connect reflux retorts with 'mad scientist'-esque glass tubing?)

"Holy Geez" - APM's Marketplace Interviews Dow (Chemical) CEO

"oh man, whatever they make is probably toxic. It's chemicals, it's hydrocarbons - holy geez, I don't want any of that stuff."


"Holy geez," indeed. The above quote, Marketplace host Kai Ryssdal's (KR) opening volley from today's interview with Dow CEO Andrew Liveris (AL), really sets the tone for the whole conversation. From there, to summarize: there's some kitschy Australia jokes, and a truckload of corporate newspeak about Dow's re-branding efforts and American manufacturing readiness. Without further ado, here's some choice quotes:

KR - "...if I say "chemistry," what do you think? People in white lab coats, right? Vials full of liquids, maybe?"

Sure, if you're into stock photos. Don't forget to include beakers, jokes about social awkwardness, and references to Breaking Bad!

Source: Busplug

AL- "But these days, you may have seen our ads on TV. We are really branding Dow. The word "chemical," of course, from a heritage point of view is still in our name." [Emphasis mine]

Again, when a major multinational conglomerate says these kind of things on syndicated radio, how can we ever hope to fight chemophobia?

AL - "So we've got to go out there and really re-educate humanity, because at the end of the day, 95 percent of all products out there have chemistry in them"

Dare I ask? What's the other 5%? Dark matter? Pixie dust? Aether? (This sounds like a job for Dr. Rubidium over at JAYFK, or our old pal Deborah Blum)

AL - "The word manufacturing, you know, even the word industry just doesn't sit well. People think about it as a smokestack, environmental, yesterday's era; that everything should be services."

I'm a proud member of the chemical industry. I make things. So do most of my colleagues, family, and friends. I'd like to say it's part of today's era. Anyone else?

AL - "We're re-branding what science, technology, engineering, maths mean to this economy and how we can transfer that into American jobs for the next generation."

Perhaps the most galling quote of all. I can hear Chemjobber sharpening his linguistic knives from all the way across the internet. Keep 'em ready, because the fight against mainstream #chemophobia continues...