Educational #Chemophobia

Usually, I use my blog as a stump to protest the branding of my chosen field as "toxic," or somehow poisonously malevolent. It's not often that I have to fight against someone who misunderstands the value of chemical education in everyday life. But, c'est la vie.

In today's Washington Post Answer Sheet, Mr. David Bernstein, a nonprofit executive from Maryland, writes in to protest an apparent state mandate that "forces" his teenage son to take chemistry. I understand that local politics get messy, and I don't presume to know the full story for his particular municipality. But why must chemistry always serve as the punching bag for what's wrong in early education?

One of Mr. Bernstein's major arguments involves future potential careers for his son: since he won't grow up to be a scientist, why take chemistry?

Suppose we argued against other required subjects (as I did earlier on Twitter):

"Why must my son take Geography? Google Maps and Garmin will always be there, right?"

"History? Not when there's Wikipedia!"

"He shouldn't take math. He'll never be an accountant, and everyone has calculators"

Chemistry boring? Sometimes, but
it's also really important.

Those arguments sound pretty far-fetched. Also, most students don't really commit to a career in Junior High, and many change their minds by college, anyway. So why not a broad education?

Second, Mr. Bernstein argues against mainstream chemistry education as "all memorization." Well, I'll agree - there's a lot to take in that first go-around. But while elemental numbering, valence electrons, and balancing equations sound rote and boring up front, the trends are the critical information. What makes atoms bigger or smaller? Why are ionic (charged) and covalent (shared) bonds so different? What does acidic or basic really mean? Once mastered, these types of rational thinking - using data to read trends - show up in all sorts of other pursuits, from buying stocks to choosing a healthy diet.

Third, Mr. Bernstein believes that his son will "suffer through" chemistry, and that he will recall little information from the course. Mr. Bernstein argues that the opportunity cost of a "painful" chemistry year will prohibit his son from taking "...subjects where he can grow and put to use one day."

I contend that a background in chemistry prepares you for all sorts of life situations. Doctors measure blood chemistry (pH, LDL / HDL ratios, chemokines, liver enzymes) to diagnose patients. Construction workers and architects rely on material properties (phase-transition temperatures, modulus, compression) to inform their building decisions. Surface area, entropy, and several organic reactions underlie cooking. Chemistry shows you why you can't clean up oil spills with water, and why a pile of salt won't dissolve in WD-40. And wouldn't it be nice to understand what all those ingredients on food labels actually are?

Boring, painful? Maybe. But useless? Definitely not.

One more thing: there are ~90* naturally-occurring elements, and a total of 118 spots (not all filled!) in the Periodic Table. I didn't have to Google it, because I took middle-school chemistry.

*Update - I originally had 92, but a curious reader corrected me - Tc and Pm are radioactive, and thus unstable in nature. So, 90. Then Stu Cantrill wrote in that several more are found in pitchblende, so I raised it to 98. Several tweets and comments have suggested numbers ranging from 84 to 98. Thus, the dreaded tilde. Good to have so many chemists about!

**Update 2 - Here's Ash at Curious Wavefunction, and Derek at Pipeline. Also see Janet over at SciAm's "Doing Good Science."

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.

Now Where Have I Heard This Before?

Yesterday morning, I heard an NPR report that detailed more strife in a typically white-collar profession. Whose field do you suppose we're discussing?

"...schools routinely said that 90 percent or more of their graduates had jobs nine months after graduation. It turns out they were including barista positions, low-level marketing gigs, or just about anything else you could call a job." [Emphasis mine]

"At some schools, less than a third of their graduating class were obtaining long-term, full-time jobs" 

"A new study reveals that since 2009, the median starting salary...has fallen 35 percent." 

Any more of these posts, and I might
have to rename the blog!
Credit: Arrested Development

Give up? It's not chemists, it's lawyers (This story does seem to spring eternal, given earlier posts by Chemjobber and myself). The comparison's just too apt to pass up: young grads consider financial security, invest their time towards an advanced degree, and later awaken to an economy facing a glut of overeducated professionals.

To their credit, at least the American Bar Association (ABA) seems aware of the risk, and wants to inform newly-admitted legal students of the economic dangers. Their Nero, unlike ours, isn't fiddling while Rome burns. So, what lessons could Ph.D.-granting chemistry departments learn from the legal profession? 


Honesty - Brian Vastag's Washington Post article from two weeks ago really struck a chord, amassing nearly 3700 comments and prompting discussion up and down the blogosphere. Although it's a political talking point (STEM STEM STEM!), chemical graduate departments must take a page from the ABA and inform new recruits that the salad days of secure scientific employment have passed.

Transparency - As Janet Stemwedel recently mused: What does a chemistry Ph.D. get you? Are alternative careers really playing out? How are pharma salaries adjusting to the recession? Are stock options, benefits, or retirement plans really going away? Where will the jobs be in 10 years?

CJ's correct to call for career tracking; after all, we have the technology! Through a combination of email surveys, social network mining, digital IDs, online CVs, and employer reporting, we should be able to paint a more complete picture of the sci-employment landscape. Using data from past students, new grads could adequately prepare themselves, and younger students could better assess their decision to attend grad school.