#chemjobs-related Writers/Reporters of the Year, 2013

I wanted to repeat something I did last year and recognize people who I feel have moved the conversation about #chemjobs-related issues forward in the last year:

Robert N. Charette of IEEE Spectrum, for his August article "The STEM Crisis Is A Myth." I think it's terribly important to address the STEM shortage myth issues from the IT/computers side, and Charette's article did just that. It has quotes from the usual suspects (the Ron Hiras and Michael Teitelbaums of the world), but it also pulls in a lot of serious policy analysis from RAND and other august institutions. A really helpful article, I thought. 

For the second year in a row, Sophie Rovner, Susan Ainsworth and Linda Wang of Chemical and Engineering News for their tireless coverage of chemist employment and unemployment. I really liked Sophie Rovner's article in the Employment Outlook edition this year, probably more than I expressed on the blog at the time. I'm planning on returning to this article, especially as 2014 progresses.  

These reporters have a much bigger microphone than I do. I tend to yell at reporters when they get things wrong; it makes me happy when I feel that writers and reporters get things right.

2013 was a weird year, especially with all the rumblings about hiring at the same time as actual layoffs increased. 

Best wishes to all of us for a less-weird, more happy new year in 2014. Talk to you then. 

December 29, 2008

I would be remiss in not mentioning that yesterday marked the 5-year anniversary of the fire that ultimately killed Sheharbano (Sheri) Sangji while she was transferring t-butyllithium in the laboratory of Professor Patrick Harran at UCLA.  

Stay safe in the lab, folks. 

A long-ago mysterious death at the South Pole

Over the break, I read this account of scientists at the South Pole and a mysterious death from methanol poisoning that happened in 2000. As someone who's not much of a drinker, South Pole scientists' reliance on alcohol is remarkable, in terms of volume. That said, it's certainly understandable.

Hard to say why Rodney Marks died; the article doesn't shed much light on it, other than a potential that Dr. Marks purchased a bottle of methanol-spiked alcohol from another country and brought it with him. An interesting story, for those who are looking for a longer article to read. 

Unlabeled flasks

Hope everyone enjoyed the Christmas break. We're mostly back to work here:

• I thought this gift of 3-D printed molecules was nice. 
• A fascinating chemical mystery from John Spevacek. (That's a very educated household, btw.)
• C&EN's year-end issue, lots of good stuff in there. 
• Hey, this "multidrug resistance gene found in Chinese wastewater plants" story sounds really bad. (by Dierdre Lockwood)
• LOLmythesis is funny, a good time waster. 

On an unrelated note, congratulations to Professor Paul Bracher, who got married over the weekend. Best wishes to the happy couple. 

What Santa brought me

I don't know why, but I was tempted by this memory game, highlighted by the Newscripts team at C&EN.

I suggested it to my wife, and lo! Here it is on my coffee table. Very fun. 

Merry Christmas!

Merry Christmas, everyone. Thanks for another great year.

Here's wishing that you are at home with your loved ones, resting and not thinking too too much about chemistry.

Everyone loves a posed picture

This Quartz piece on the misadventures of a battery/electrochemistry startup that worked with GM on some of the technology for the Volt is pretty interesting. Seems to me that the GM side was quite new to battery chemistry and did not know the right questions to ask or specifications to set.

One little detail I really liked from the story was the posed picture of the two managers from Envia. Of course, it's a posed picture, but the best part is the creases in the brand-new-from-the-wrapper paper lab coats that they decided that both folks should wear. 

The 12 Days of Aldrich Christmas Index

I really love Christmas music (listening to some Johnny Cash Christmas right now), but I roundly detest the "12 Days of Christmas." Nothing quite like a really, really repetitive song to capture your ears. But I thought it might be fun to do a little tracking index, so I present the 12 Days of Aldrich Christmas Index, to be done annually, the Friday before the week of Christmas:

12 drums (25 L) of (undrinkable) booze ($21,540)
11 postdocs pipetting (NIH year 0 postdoc stipend, $431,904)
10 grams of RuPhos (2 5 gram bottles, $514)
9 can openers (extra hard cutting wheel!, $146.70)
8 DEA forms (free!)
7 Schlenks inerting (3 port, Ace vacuum manifold, $4935)
6 ground glass joints (reducing adapter, 14/20 to 24/40, $180)
5 Cork Rings (30 mm X 80 mm, $59.50)
4 Trifluoromethylators (1 gram, 90%, $800)
3 Grignard bottles (800 mL, 1.0M PhMgBr in THF, $222.60)
2 Kugelrohrs (glassware set, $387.40)
And a 1 gram bottle in a huge box (99%, 1 gram, Pd(PPh₃)₄, $37)

The grand total for the 12 days of Aldrich Christmas is $460,726.20. (Most of the cost is the 11 postdocs pipetting. Labor costs, you know.) 

A Chemjobber holiday tradition

As a public service to chemistry graduate students everywhere, I'm rerunning this post. (It's been updated.) Feel free to e-mail/print out and give to your family. 

Interesting news tidbit

Don't know what to think of it, but from the inbox, a (lightly edited) comment from a reader in India:

After shutting down CNS in US, Biocon Bristol Myers-Squibb Research Centre (BBRC) Bangalore, India has laid off about 30% of its work force in medicinal chemistry including the director. This centre was CNS centric, most of the work was on CNS diseases.

Anyone else have a similar story to report?  

From your keyboard to God's ears, Luke Timmerman

In an article titled "12 things the pharma industry can do to rebuild real public trust", a rather inspiring section here:

7. Invest in your own employees. The biomedical industrial complex has educated lots of young graduate students and postdocs over the past decade, during the boom in NIH funding from the late-90s to the early 2000s. Many of these people are stuck with no job prospects, because they can’t get the precious few faculty gigs at cash-strapped universities, and most haven’t gotten all the training and mentoring they need to be relevant for jobs in industry. Ethan Perlstein, a former Princeton University postdoc who struck out recently on his own as an independent scientist, has referred to this phenomenon as the “postdocalypse.” This is a huge recruiting opportunity for pharma, to snap up lots of bright people at entry and mid-levels and train them for long careers in industry.  

Instead, you just see wave after wave of layoffs in R&D, as companies seem to be almost throwing in the towel on all their good medicinal chemists, molecular biologists, biochemists, and more. It’s short-sighted, and unfair to those people. This isn’t a poverty-stricken industry like my former world of newspapers, which can’t afford to hire people. Pharma can and should do this for its long-term survival.

The bit about the difference between the newspaper industry and pharma industry is really true. There have been no disruptive technologies that have annihilated pharma's revenue sources, and yet, the layoffs continue... 

Process Wednesday: Stupid reactor cleaning solvents!

Bert Hulshof's* "Right First Time in Fine-Chemical Process Scale-up" has a rather wonderful chapter of "non-flyers", as he calls them. These are reactions/processes that worked well in the lab, but not in the plant. Here's one about a Grignard that I found hilariously funny:

- Pilot-plant scale 

9. The pilot plant results were identical to those in the lab.
10. However, on plant-scale, the Grignard reaction could not be initiated.  

 - Review 

11. Back in the lab, it was demonstrated that small quantities of acetone are the real cause of this Grignard initiation problem.
12. Acetone was a cleaning solvent, frequently used to dry reactors, condensers and piping. Usually final traces of this solvent could be removed by applying vacuum on various equipment sections.  

 - Solution 

13. After the make-up of magnesium and THF, a certain quantity of Grignard solution of the previous batch was added to destroy remaining acetone...

I can only imagine the irritation of the chemists upon learning of this stumbling block.

Grignard initiation on plant scale can be tricky and potentially quite dangerous (in terms of adding a bunch of halide and magnesium together that might react all-at-once and spray hot flammable solvent out of the rupture disk.) I've heard of SOPs where a verifiable initiation (as measured by exotherm or other in-process check) must take place before the full quantity of halide can be added.

*Sadly, Dr. Hulshof's passing was noted in OPRD recently. 

Why I Do Not Like LinkedIn Groups

I don't find this particularly helpful, but maybe that's just me. 

Professional Science Master's in Chemistry?

Does anyone have experience with Professional Science Master's Degrees in chemistry?

(I recently chatted on Twitter with Jeff Terry (a physics professor at IIT) and he was pretty supportive of their PSM in analytical chemistry.)

There are 11 programs listed on the PSM degree website for chemistry: Case Western Reserve University, Illinois Institute of Technology, Indiana University of Pennsylvania, Missouri Western State University, Rutgers, The State University of New Jersey-New Brunswick, State University of New York at Buffalo, State University of New York at Oswego, Stony Brook University, Temple University, University of Massachusetts Lowell, University of North Texas.

I have some questions for readers:

• Have you heard of any graduates of these programs? How are they fairing? 
• Do these programs charge their students tuition, or is tuition paid for by company, or through the TA/RA route like more academic master's programs? 
• What are these programs' track records in placing their graduates? Do they track their employment histories? 

Daily Pump Trap: 12/17/13 edition

Good morning! Between December 12 and December 16, there were 65 new positions posted on the C&EN Jobs website. Of these, 15 (23%) were academically connected. 34 positions (52%) were from Kelly Scientific Resources.

Lake Zurich, IL: Fenwal is looking for a B.S./M.S. analytical chemist with ICP experience.

Rolla, MO: Brewer Science is looking for a B.S.-level analytical chemist. At its Springfield, MO site, Brewer is also looking for a Ph.D.-level analytical chemist. 

Ridgefield, CT: Boehringer Ingelheim is looking for a M.S./Ph.D. process chemist. The list gets weirdly specific (emphasis mine):

Must possess graduate college coursework/project or work exp. with the following: Heterocyclic & esters/ethers containing organic compounds; using high technological instruments such as NMR, HPLC-MS, GC, GC-MS, HPLC-prep, LCMS & IR spectrometer; using pressurize reactor such as for hydrogenation; drug design & development; synthesis & purification of RNA linkers; design & development of solvent free environmentally friendly green chemical processes, e.g. one-pot synthesis of Acetaminophen, Tylenol®; design and synthesis of N-aminated heterocyclic compounds;

Huh?

Newark, DE: Lightwave Logic is hiring an experienced organic chemist to synthesize new dye chromophores. 

Ivory Filter Flask: 12/17/13 edition

Good morning! Between December 10 and December 16, there were 35 academic positions posted on C&EN Jobs. The numbers:

Postdocs: 4
Tenure-track: 21
Temporary faculty: 1
Lecturers: 5
Staff: 4
US/non-US: 28/7

San Luis Obispo: Cal Poly-San Luis Obispo is hiring two assistant professors of wine chemistry. I have no idea what a world-class program in wine chemistry is, but I'd sure like to find out.

Danbury, CT: Western Connecticut State University is hiring an assistant professor of organic chemistry.

Houston, TX: The University of Houston desires an assistant professor of synthetic inorganic chemistry.

Atlanta, GA: Oglethorpe University is also looking for an assistant professor of organic chemistry.

Athens, GA: The University of Georgia needs an NMR manager.

Dartmouth, MA: ...as does the University of Massachusetts-Dartmouth.

If you see Richard Kiel, run: Osaka University is hiring assistant professors for the "Frontier Research Base for Global Young Researchers." Sounds like something from a James Bond movie. 

Worth thinking about: the Survey of Earned Doctorates in 2012, gender outcomes

Beth Haas has posted a very interesting analysis of new Ph.D. graduates in chemistry (via the 2012 Survey of Earned Doctorates.)

My thoughts:

• It'd be interesting to see the gender differences for the "further study" (i.e. postdocs) category, as well as the "employment" category. 
• I wonder if there's a difference in self-reporting with men and women? 

Hmmmmmm. It's definitely worth your time.

An interesting correction

In this week's C&EN's letters section, an interesting correction from this article by Sophie Rovner:

In the same article, C&EN incorrectly characterized Pfizer’s medicinal chemistry hiring plans. Pfizer is looking to enhance its in-house synthetic organic chemical capabilities to complement the talents of its contract research partners. The goal is to build internal synthetic problem solving for particularly challenging molecules.

I have to go hunting in my garage for this issue to figure out what Pfizer objected to... 

The used plant market

From this week's C&EN, a fascinating article by Marc Reisch on the used plant equipment market:

...In June, the biotechnology firm Affymax auctioned off pharmaceutical equipment at its Palo Alto, Calif., facility, raising $1.4 million. Earlier in the year, Affymax recalled its only product, a drug to treat anemia. The company announced it would restructure itself and might declare bankruptcy. 

Idle equipment from firms such as Hoku and Affymax was once likely destined for the scrapyard or a ship bound for China, but these days it may end up back on U.S. production lines. Used equipment dealers are anticipating a resurgence in U.S.-based manufacturing brought on by cheap energy and raw materials derived from shale gas. 

Right now, dealers have huge inventories of unused plants and equipment. Although some of that inventory comes from recent bankruptcies or business reversals, even more idle equipment is sitting around because of mergers and industry consolidations, some of those going back to the Great Recession of 2008. 

International Process Plants, which buys petrochemical, pharmaceutical, fertilizer, and oil-refining plants, owns 100 complete process plants for sale, according to IPP President Ronald H. Gale. 

IPP’s inventory includes methanol, hydrogen, polyester, and polyethylene facilities. Until recently, a lot of used plants and equipment went from the U.S. and Europe to buyers in the developing world, Gale says. But low-cost U.S. natural gas is beginning to change the flow of asset purchases. 

In what he hopes may be a harbinger of things to come, Gale says some used plants and equipment are being shipped to the U.S. from overseas. His firm recently sold a pharmaceutical-grade glycerin purification plant in the U.K. to a customer who relocated it to the U.S. 

But the cost of moving large equipment over long distances can be high. Gale is counting on the planned buildup of shale-gas-fueled petrochemical facilities by firms such as Dow Chemical, Shell Chemicals, and Braskem to drive up U.S. demand for some of the downstream plants that IPP owns.

If I had all the time in the world, I would keep track of this more closely than I do. It's always interesting to me, the secondary markets in used equipment. 

2 inch octagonal stir bars

A list of small, useful things (links):

• Quintus comments on the filibuvir papers.
• Over at Chemistry Blog, chemistry Advent poems.
• John has goofy thoughts about plastic bags.
• Vittorio is very clever with his TLCs.
• This post about trailing spouses by @belehaa was really thought-provoking.
• Kilomentor moved a while back to a new site; still posting! 
• I really enjoyed Deborah Blum's thoughts about Yasser Arafat and polonium.
• Jess' top 10 chemistry papers of 2013.
• Did you know there's a German chemistry job blogger? You do now!
• Chad Jones does really good chemistry podcasts; his interview with Carmen Drahl and his sons were both worth a listen. 

Did I miss anything? Put it in the comments. Have a great weekend! 

"Civility and Legality in Hiring"

I was recently made aware of an article by Professor Dave Reingold titled "Civility and Legality in Hiring" [1] Here's an interesting excerpt from it: 

11. How often should you communicate with candidates waiting to hear from you?  What information should you provide? 

After spirited discussion, the consensus of the group was that you should tell your candidates as much as possible, as often as possible.  Applications should be acknowledged, and if possible candidates should be told when their files are complete, or, as the deadline approaches, what they are missing.   

Then comes the waiting game:  we have all been through this process, and we know that the hardest part is waiting around for someone to tell you what is happening.  The group concluded that every time a decision is made, all active candidates should be told about it.   

When you make the first selection from 100 down to 15, you should tell the 15 that they are in the top 15, and the rest that they are not (I have made up these numbers, and do not mean to imply that there is any correct number or size of cuts).   

Note that this does not constitute rejection, and the communication should carefully say so, but on the other hand it is clearly exceedingly rare for someone who does not make the top 15 to eventually receive an offer.  When you get down to six, the other nine should be told that they are not in the top six, and so on.  Most places interview three candidates in the first round.
During the interview, it is appropriate to tell the candidates when you expect a decision to be made, and when that day comes, contact the candidates!  If the decision was not made, say so; if it was, go ahead, tell them what it was.   

Tell them if the decision is in the hands of the VP.  Tell them what your recommendation to the VP was.  If an offer is out, tell them when the first candidate has to respond, and tell them when the first candidate does respond.  If you know who is second and third, tell them.  If you don’t, tell them that!   

When you get a verbal commitment, tell the others.  Young faculty in the room all agreed that they would want to know that there was an offer out to someone else, but that there was not yet a response, and there was certainly a chance of a “no” answer at which point they were next in line, etc. There was no suggestion from the group that this policy would make a candidate less likely to accept an offer if one came later.  Quite the contrary, some believed they would be more likely to accept an offer, because the communication suggested an open and fair department and institution.   

The unanimous opinion of the group was that all aspects of the search should be conducted with the maximum possible openness.  Candidates will feel positively towards a department that is open with them, and increasingly negative towards a department that leaves them dangling for long periods of time. 

We realize that we have recommended a lot of communication, which would be very expensive in time and money if done by letter.  But e-mail lists work great for updating applicants on their status, and it is free (for now!).  However, remember our earlier admonition: e-mail is not private.  The candidate may not appreciate an electronic status update.  The point is, do the best you can to keep applicants informed of progress; we see no point in hiding information.

The article was published in 1998 and aimed at faculty positions. I think keeping people informed as much as possible is pretty wonderful; it's a real shame that it doesn't happen more often. In the great day when I'll hold sway over hiring (this is after the Cubs win their 3rd back-to-back World Series), I'll plan to stick to this. 

1. “Civility and Legality in Hiring,” Reingold, I. D., CUR Quarterly 1999, 19, 180.

How to break into venture capital and the like?

I don't know the first thing about management consulting or finance (private equity or venture capital), so I thought I would ask. (I should note that I do understand that all three areas are separate, distinct and necessarily related.)

I am sure there are Ph.D. chemists in the field -- one of my first fun posts was tracking down the factlet that 25% of Harvard's chemistry Ph.D. class between 2005 and 2008 ended up in business/finance of some sort.

So I have a few questions:

• The big management consulting firms (the McKinseys of the world, etc) are still hiring, and still hiring new Ph.D. graduates, right? Probably from top-tier programs? 
• I presume that breaking into venture capital requires some amount of technical education (i.e. a M.S. or Ph.D.), but also some job experience in the relevant field (biotech, pharma, whatever?)
• What do you do all day if you're in venture capital? I assume that you're constantly sifting through proposals from various people, looking for organizations that have a good idea that might make money. 
• What entry-level positions in private equity firms would be relevant for new Ph.D. grads? 

Readers, any thoughts? Much appreciated. 

ACS/NESACS sponsoring small chemical business pitch/investment competition

From Jennifer Maclachlan (analytical chemist, and part of the ACS Small Business Division), a very interesting idea:

ACS ENTREPRENEURIAL RESOURCES CENTER SHOWCASE EAST 

The  ACS - in cooperation with The Northeastern Section of the  American Chemical Society, the ACS Small Chemical Businesses Division, and the Nova Biomedical Corporation - is sponsoring a one-day business competition with a cash prize for the  winning pitch delivered to investors and potential commercial partners on Wednesday, April 9, 2014 at the headquarters of Nova Biomedical Corporation at 200 Prospect Street, Waltham MA, 02454. 

Entrepreneurial candidates must be ACS members and have an early-stage chemistry based startup that is investor ready. 

To qualify for participation in this business competition, candidates must complete our investor readiness survey. Access the survey  here. Survey closes January 20, 2014. Note: There are only 20 slots available. Candidates who are selected for participation will  work with an assigned mentor to develop a winning pitch.

Details are here, here and here. It seems to me that this is one of those things where you should think about entering, even if you're not sure you're ready. Best wishes! 

Job posting: Perkin-Elmer Informatics looking for a marketing specialist on the West Coast

From friend of the blog Philip Skinner (an executive director of marketing at Perkin Elmer Informatics), a job posting:

We are looking for a West Coast junior life scientist who can travel the country to evangelize the use of Spotfire in R&D and clinical lifescience organizations. We probably want someone with a bio more than a chem background but his would be an interesting opportunity for a lifescientist looking for a different career. 

The ideal candidate will have a background in life science research, either in discovery, pre-clinical, clinical or translational research, ideally within an industry setting. A broad  understanding of the processes involved in clinical and/or translational research would be an advantage. They will be familiar with creating and authoring visualizations on the Tibco Spotfire platform to progress life science research. Prior experience with other Enterprise scientific software such as E-Notebook, LIMS, Columbus, Empower, R, SAS, etc. would be a plus.

See here for details. E-mail Philip at philip.skinner -at- perkinelmer.com if you're interested. 

Daily Pump Trap: 12/12/13 edition

Good morning! Between December 10 and December 11, there were 36 new positions posted on the C&EN Jobs website. Of these, 19 (53%) were academically connected and 14 (38) were from Kelly Scientific Resources.

Not much, really: Kelly positions and academic slots. Sigh.

Blacklight Power!: Blacklight Power will post jobs everyonce in a while; they're looking for a senior mechanical engineer. For more information on this rather dubious organization, see Derek Lowe's posts.

Huh: I'm probably going to cover this in next week's IFF, but Shenzhen University is hiring a crap ton of professors (30 openings), some for chemistry. Shenzhen isn't a very nice part of China, but it likely is very exciting to be there.

A broader look: Monster, Careerbuilder, Indeed and USAjobs.gov show (respectively) 206, 700, 2593 and 19 positions for the search term "chemist." LinkedIn shows 149 positions for the job title "chemist", with 12 for "research chemist", 19 for "analytical chemist", 3 for "organic chemist" and 1 for "synthetic chemist." 

Special orders don't upset us

A reader sends in a recent Simply Hired search:

Think of the transferrable skills! Network to your next position! 

How do you stop high school chemistry demonstration accidents?

Thanks to Jyllian Kemsley, I see that the CSB has a new video out, and it's about a chemistry demonstration gone horribly awry. It ended in severe burns to the face of one of the students:



This Cleveland Plain Dealer article has a fairly detailed look at the story (the demonstration was the classic methanol flame/various salts experiment) and subsequent settlement. The details are gruesome and the teacher in question was grossly irresponsible, to say the least. (She paid a tragic price, in that her son was part of the permanently injured group.)

Like Jyllian, it seems to me that there are a lot of alcohol fires reported in school settings (as crudely measured by Jyllian's chemical safety roundups.) I wish I knew how I could help the situation; by putting this on YouTube, it seems like CSB has put their best foot forward.

There's a lot of great things that can come out of high school chemistry demonstrations. My high school chemistry teachers would put on the classic flame/explosion show (magnesium/dry ice, hydrogen balloons, they did a thermite reaction one year) and it was freakin' awesome. I loved it. They managed to do things the right way; they were fairly serious about safety (PPE for them, keeping us a fair distance away). In the case in the video, there wasn't an adequate enough amount of administrative supervision. There never is, I suppose.

How to prevent a Western Reserve-type accident (or another bugaboo, the exploding nitric acid waste bottle) from happening? I don't know, but I'd sure like to try. 

Process Wednesday: a LiHMDS mystery

Peng et al. OPRD

In the midst of 3 very interesting papers [1] on the process development for the compound filibuvir, a fascinating comment from some Pfizer process chemists on Dieckmann cyclization (see figure to right) yield variation due to the source of lithium hexamethyldisilazide:

We also observed a source-dependence for the LHMDS, similar to that observed with the oxazolidinone substrate. (CJ's note: the authors had an oxazolidinone in place of the ethyl ester in structure 23 in a previous route.) With LHMDS prepared from n-BuLi and HN(TMS)₂ the yield was consistently 88−90%. However, in the case of one supplier using a lithium metal process (Li metal, 2-methyl-1,3-butadiene, HN(TMS)₂), a consistently lower yield of 81% was observed.
Similar observations with LDA prepared from n-BuLi vs Li metal/styrene have also been reported. In the course of investigating the cause of this variation, we identified two additional suppliers who used the lithium metal process, but with those sources the higher yield was consistently obtained (88−90%). We also found that if the “low olefin content” grade of LHMDS was used from the initial supplier, the yield improved to 85−87%. 

We studied several potential culprits, including the presence of residual 2-methyl-2-butene and small quantities of other metal contaminants (e.g., sodium amide bases, LiCl, and Li-alkoxides), but none of these accounted for the observed discrepancy. In all cases where the yield decreased, an increased level of elimination impurities was observed (i.e., the total mass balance was consistent). While these results continue to intrigue us, our successful identification of at least three viable commercial suppliers (Optima, BASF, and Chemetall “Low Olefin Content” LHMDS) for the reagent and the relatively modest yield variations have attenuated our concern with this unexplained LHMDS source variation.

Below, the proposed elimination pathways and accompanying text that were in the oxazolidinone route (which was covered in the first paper in the series):

Singer et al. OPRD 

The two elimination pathways are shown in Scheme 6. The first involves elimination of acetic acid from the cyclization substrate 24, to form a mixture of acrylamides 28. An E1CB mechanism via the lithium enolate is shown, but this could also proceed through an E2 elimination in the presence of a weaker base such as the lithiated oxazolidinone generated during the cyclization. The second pathway is a ring-opening elimination of the β-keto lactone product to generate a β-keto acid, which undergoes decarboxylation to generate a mixture of enone isomers 29. The top elimination pathway predominates in “normal addition” mode, i.e. addition of LHMDS to the substrate. We estimate the pKa values of the relevant protons at ∼25 for C3′ and ∼23 for C2. The use of a strong, hindered base such as LHMDS and the low reaction temperature (−20 °C) favor kinetic deprotonation at the more sterically accessible position (C3′). Nonetheless, direct enolization at C2 remains a possibility, and intramolecular proton transfer from the desired C3′ enolate to C2 is also feasible.

I don't have any good answers for their questions either. Why would the method of preparation of LiHMDS matter? What is in there that is promoting elimination? Why is potassium and lithium tert-butoxide much worse? Readers, any ideas?

1. (a) Singer, R.A.; Ragan, J.A.; Bowles, P.; Chisowa, E.; Conway, B.G.; Cordi, E.M.; Leeman, K.R.; Letendre, L.J.; Sieser, J.E.; Sluggett, G.W.; Stanchina, C.L.; Strohmeyer, H.; Blunt, J.; Taylor, S.; Byrne, C.; Lynch, D.; Mullane, S.; O’Sullivan, M.M.; Whelan, M. "Synthesis of Filibuvir. Part I. Diastereoselective Preparation of a β‑Hydroxy Alkynyl Oxazolidinone and Conversion to a 6,6-Disubstituted 2H‑Pyranone." Org. Process Res. Dev. ASAP dx.doi.org/10.1021/op4002356 (b) Peng, Z.; Ragan, J.A.; Colon-Cruz, R.; Conway, B.G.; Cordi, E.M.; Leeman, K.; Letendre, L.J.; Ping, L.-J.; Sieser, J.E.; Singer, R.A.; Sluggett, G.W.; Strohmeyer, H.; Vanderplas, B.C.; Blunt, J.; Mawby, N.; Meldrum, K.; Taylor, S. "Synthesis of Filibuvir. Part II. Second-Generation Synthesis of a 6,6-Disubstituted 2H‑Pyranone via Dieckmann Cyclization of a β‑Acetoxy Ester." Org. Process Res. Dev. ASAP dx.doi.org/10.1021/op400236r (c) Ide, N.D.; Ragan, J.A.; Bellavance, G.; Brenek, S.J.; Cordi, E.M.; Jensen, G.O.; Jones, K.N.; LaFrance, D.; Leeman, K.R.;  Letendre, L.K.; Place, D.; Stanchina, C.L.; Sluggett, G.W.; Strohmeyer, H.; Blunt, J.; Meldrum, K.; Taylor, S.; Byrne, C.; Lynch, D.; Mullane, S.; O’Sullivan, M.M.; Whelan, M. "Synthesis of Filibuvir. Part III. Development of a Process for the Reductive Coupling of an Aldehyde and a β‑Keto-lactone" Org. Process Res. Dev. ASAP dx.doi.org/10.1021/op400237j

Daily Pump Trap: 12/10/13 edition

Between December 5 and December 9, there were 51 positions posted on the C&EN Jobs website. Of these, 14 (27%) were academically connected and 31 (61%) were from Kelly Scientific Resources. 

South San Francisco, CA: Genentech is looking for a B.S./M.S. research associate in drug delivery; chemical and polymer synthesis experience desired. 

Irvine, CA: Allergan is looking for a process chemistry manager. This seems very interesting, in that it's all about outsourcing API manufacture: 

...The Process Chemistry group (Prochem) is responsible for supply of small molecule, drug substance for all phases of Allergan’s research and development activities.  This includes Medchem/Discovery support, sample synthesis, early development chemistry, process research, scale-up and process validation.   These synthetic chemistry projects are done entirely by outsourcing with various contract research or manufacturing organizations (CRO/CMO).  Prochem is responsible for providing quality assurance and global CMC regulatory guidance to CRO/CMO’s.... 

Ph.D. + 4 years specific experience in a chemistry related field in the pharmaceutical or API manufacturing industry; MS +7 years specific experience in a chemistry related field in the pharmaceutical or API manufacturing industry; or BS + 9 years specific experience in a chemistry related field in the pharmaceutical or API manufacturing industry.   Ph.D. strongly preferred. Must be willing to travel up to 20%.

Santa Clara Valley, CA: Via the inbox, a LinkedIn posting for an analytical chemistry position at Apple:

Provides expertise in the acquisition and interpretations of data using analytical chemistry tools including: FTIR, TOC, LIBS, ICP-MS, etc. 

Key Qualifications 

5 years of laboratory experience relating to inorganic chemistry and/or materials characterization
Data validation and method development/method validation experience
Hands-on experience with numerous analytical tools

 BS/MS in Chemistry desired. Huh. Did not know they hired chemists. 

Ivory Filter Flask: 12/10/13 edition

Between December 3 and December 9, there were 24 academic positions posted on the C&EN Jobs website. The numbers:

Postdocs: 2
Tenure-track: 13
Temporary faculty: 4
Lecturers: 5
Staff: 0
US/non-US: 22/2

Huh: I'm surprised that positions for tenure-track positions are still being posted.

Raleigh, NC: I confess I wasn't aware of a College of Textiles, but they're hiring an assistant professor of analytical chemistry for it.

Irvine, CA: Chapman University is setting up a School of Pharmacy; looks like they're looking for assistant professors to staff it. Pharmacy degrees desired, among others.

Ulsan Metropolitan City, South Korea: This sounds very futuristic (emphasis mine):

The Ulsan National Institute of Science and Technology (UNIST) and the Institute for Basic Science (IBS) are proud to announce the establishment of “The Center for Multidimensional Carbon Materials” (CMCM) in Ulsan, South Korea. A primary objective of the Center is to design and develop the next generation carbon materials, and a prominent chemist is needed to lead synthetic and characterization efforts. 

Multidimensional carbon! A clever scifi writer could come up with a good story around that.

Charlottesville, VA: An astrochemistry research scientist position is being offered at the University of Virginia. It sounds complicated, for sure. (Note that it requires an astrochemistry postdoc.) Another one of these formal-ads-that-aren't-really-ads? Probably. 

Placeholder

Busy this morning, but for your consumption, the latest data from the Survey of Earned Doctorates for 2012. Things look about the same as 2011, but still a little grim. Here's the data for employment for chemistry PhDs. Sure looks to me like the modal outcome of a chemistry PhD is a postdoc. 

The latest #chemjobs frontier: medical marijuana testing?

Beth Halford has a very intriguing look at the analytical testing of medical marijuana in this week's C&EN. She ends the piece with a comment on how some of the chemists in this field might be concerned about their how their work is viewed by science:

Before opening ProVerde Labs in September, Hudalla spent 14 years developing instruments and analytical methods with Waters Corp. “I’m a chemistry nerd at heart,” he says. “I am probably the least likely person in the world to have anything to do with a drug, so my friends think it’s a big joke. But it’s really the chemistry that drives me. I learn so much every day.” 

The scientists who spoke with C&EN have spent years working in more traditional chemical careers in academia, industry, and government. Many say that they do at times worry about how the scientific community will perceive their work with marijuana. But all say that the work is rewarding, particularly when they hear from patients how the drug has transformed their lives. As Hudalla puts it, “I feel like this is part of my contribution back to mankind.”

If you'll forgive me for donning my political pundit hat for a brief moment, it seems to me that we are much closer to something akin to legislatively-driven federal marijuana decriminalization than we were 10 years ago. With that in mind, it seems that analytical testing of marijuana is a growth field and something that just might employ more chemists 10 or 20 years from now than it does today.

There's going to be a raft of new regulation to go around it, which will be interesting. What is marijuana? A recreational drug? A pharmaceutical? If FDA gets involved, will we have cGMP cannabis farms? Will the pharma industry get into marijuana (doubt it.)  Hmmmm. 

Are research scientists being replaced by mathematicians?

In Rick Mullin's year-in-review article on pharma, he talks more about big data (emphasis mine):

The main front in data, however, continues to be “big data” in the laboratory. Information technology firms responded in 2013 with a new generation of electronic lab notebooks and other software for collecting, storing, and analyzing data in drug discovery and development. Drug firms are seeking statistical analysis skills in the lab. Some even claim that research positions once filled by scientists who are taught statistics on the job are now filled with mathematicians who learn the science in the lab.

I would like to know, are there any recently-hired mathematicians working in bench-level (or bench-adjacent) positions in the life sciences industry, i.e. "a research position once filled by scientists"? I offer a shiny Sacagawea dollar to the first five people who can comment or privately e-mail me evidence of this (evidence being a verifiable LinkedIn profile).  I am defining "mathematician" as someone whose terminal degree (B.S./M.S. or Ph.D.) was "mathematics." I am defining "recently hired" as "hired since January 1, 2010."

I presume, though I do not know, that this is somehow related to this Ian Shott interview from earlier this year.

Either way, a very interesting development. 

This week's C&EN

Lots of newsworthy tidbits in this week's C&EN:

• Rick Mullin's cover story is full of DOOOOOOOM for the pharma industry. 
• I found this editorial by Roald Hoffman about a Middle East chemistry conference worthwhile and sad. Students doing molecular modeling in Syria in the middle of a civil war is just an awful picture. 
• Carmen Drahl looks over the latest numbers from NSF on academic R&D spending from 2011; the chemical R&D spending rankings are interesting.  
• The European chemical sector does not love Europe's higher energy prices. 

Dictation software: still not quite there yet for chemistry

Thanks to an excellent suggestion by Layne Morsch, I decided to put my iPad's voice recognition software to the test. Below is a recording of me reading the Evans aldol procedure to my iPad, and the untouched,  unedited text is below:

The boron out all reaction into the dry 2 L flask equipped with a large my next during bar is introduced 21.2 g 0.091 moles of the a slated oxazole the flask a sealed with a rubber septum and swept without you can solid is dissolved into hundred milliliters of anhydrous dichloromethane which is introduced via syringe. 

I thermometers inserted through the rubber septum and the contents of the Flasseur cool to 0°C with a nice bath to this cool solution is added via syringe 27 mL 0.107 moles of dibutyl boron true flight followed by 16.7 mL 0.1020 moles of triethylamine drop wise at such a rate as to keep the internal temperature below 3°C. 

The solution may turn slightly yellow or green during the dibutyl more Entre plate addiction and then to light yellow one triethylamine it's added the ice bath is then replaced with the dry ice chest that when the internal temperature drops below -65°C 10.3 mL 0.10 moles of freshly distilled benzaldehyde is added over a five minute. Via syringe the solution astir for 20 minutes in the drive sasktel bath then for one hour at icepack temperature. 

The reaction mixtures quenched by the addition of 100 mL of the pH 7 aqueous phosphate buffer and 300 mL of methanol to this Claudy solution is added by syringe 300 mL of a Toodle one methanol 30% aqueous hydrogen peroxide at such a rate as to keep the internal temperature below 10°C. 

After the solution Strid for additional one hour the vault materials removed on a rotary evaporator out of bath temperature of 25 to 30°C the resulting slurries extract with three 500 mL portions of diethylether the combined organic extracts are washed with 500 mL of 5% aqueous sodium by carbonate and 500 mL of brine dried over anhydrous magnesium sulfate filter and concentrated on a rotary evaporator to 435 to 36° 35 to 36 g White solid be on purified aldol adduct has a nice turmeric purity of greater than 97% as determined by gas chromatography the solidus recrystallize from circa 500 mL of 1 to 2 at the last eight hexane to yield 25.8 g or 84% yield of the desired aldol at with a melting point of 92 93°C 

the mother liquor is purified by flash chromatography column dimensions 8 x 20 cm with flash great silica gel.  The mother liquor is purified by flash on Aleutian with 25% of lasted hexing additional 2.8 g 9% die Stermara leaps dais there you Merickel he pure material is obtained.

I don't think Siri is quite ready yet to run a reaction in the lab, although perhaps I could use better diction.

Have a great weekend! Toodle!  

What happens after you leave your on-site?

A recent discussion with a friend commiserating job prospects left me with a few questions for discussion :

• What happens after a candidate leaves an on-site, and the overall impression is positive? 
• Presumably, the chemists get together and nod and say, "Yeah, that's our guy/gal." Then what? 
• Do they talk to the boss? 
• How does HR get involved? 
• Who holds the power, HR or "the boss", however he or she may be defined? 
• What explains long delays that don't end in "No" after an on-site? 
• Are long silences (without an outright "we are not hiring you") to do with money ("Do we have the money for this position?"), or that they're looking for another candidate? 
• Should the candidate keep contacting the potential employer to remind them that they're still interested? 
• What explains the change in hiring between modern times (2009-present) and the boom times of the late 1990s? Is it simply that the balance between employer and potential employee is so off-kilter that behavior that would be considered really rude/unkind is now de rigeur? 

I'd be curious to hear the opinions of hiring managers, or those who have participated in the hiring process. 

November jobs report: 0.3% drop in national unemployment rate, 203,000 non-farm payroll jobs added

Fresh electrons from the Bureau of Labor Statistics: the National Unemployment Rate fell 0.3% in November to 7.0%. The broader U6 rate dropped 0.6% to 13.2%. 203,000 non-farm payroll jobs were added to the economy.

The unemployment rate of college graduates was 3.4%, down 0.4% from October. The unemployment rate for non-high school graduates was 10.8%, down 0.1% from October.

Employment in the chemical manufacturing subsector was up 2,200 jobs to 795,700 jobs.

Revisions for September and October were relatively modest, with a total increase for those months of 8,000 positions.

This looks like good news; the media may be focused on the labor-force participation rate and the employment/population ratio, both of which increased.

When the boss is wrong about chemistry

How do readers handle it when senior chemist managers routinely give bad (as defined by irrelevant, against literature precedent or simply wrong-on-first-principles) chemistry advice?

There are a number of tactics, all of which I have employed at one time or another:

• Ignore the bad advice. Keep doing what you're doing, show milestone success (however defined) and move on. 
• Nod noncommittally at the bad advice, run a few experiments to placate the manager, keep doing what you're doing. 
• Quiet, subtle resistance. Questions like "are there concerns about neighboring-group participation?" 
• Open, direct confrontation. "I don't think that's correct, and here's why..." 

Obviously, Tactic Four is to be deployed on a limited basis only. 

I'd like to hear reader experience and advice with these problems, if you have them. 

[When I hear incorrect chemistry counsel, it can really frustrate me and knock me off my flow. Speaking the chemical truth is important to me, and it makes me unhappy when senior people do not. (That was one of the really wonderful things about graduate school -- the likelihood that your professors knew exactly what they were talking about was better than 95%. In industry, it's... lower than that.) I should really learn to deal.]

UPDATE: Before anyone trots out the old, old joke about Rule 1 and Rule 2, I note I've been there already.

Job posting (?): freelance writer, Motley Fool

I was contacted by Motley Fool and asked to post ad for bloggers on biotech:

Motley Fool Freelance Network – Healthcare/Pharma/Biotech Writers
Love investing? Love to write? Love the healthcare industry and/or science?

Then you might make a great contributor to our Motley Fool Freelance Network.

The Motley Fool’s Healthcare Bureau Provides original analysis on stocks in the healthcare sector (pharmaceuticals, biotechs, health insurance companies, PBMs, etc.)  Our Freelance Network has two goals:

• To share your sharp analysis and compelling writing with thousands of individual investors;

• To help you develop your analysis and writing to the point that you can earn a contract writing with Fool.com (a role that can mean more than $100,000 a year!). Together, we'll be helping the world invest better.

Our Freelancers are encouraged to build a partnership with Fool.com editors and analysts and build expertise in financial analysis, storytelling, and the Foolish writing style that has served as the foundation of our company's success. 

We offer a pay structure that is clear, transparent, and, we hope, generous. If you write a post that is thoughtful, well-written, and makes specific and relevant mention of businesses and their tickers, we’ll publish it and pay you $50. If you develop a track record of high performance and if your posts are viewed as top-notch by our team at the Fool, you will be paid $100 per post. 

As many of our successful freelancers can attest, that might just be a starting point for your relationship with the Fool. We keep an eye out for the best writers and analysts -- those who truly work with us as partners -- and offer writer contracts to the best of the best. And that can lead to even bigger things. 

If you’re ready to get started, just head to http://fool.com/join and you’re on your way. If you have questions, shoot us an email at writeforhealthcare@fool.com.

As most of you know, I'm not much of one for individual stock purchases. That said, I know plenty of my readers might be. Sounds like an interesting way to write about your investing hobby. Best of luck! 

Daily Pump Trap: 12/5/13 edition

Good morning! Between December 3 and December 4, there were 27 new positions posted on the C&EN Jobs website. Of these, 11 (41%) were academically connected and 7 (26%) were from Kelly Scientific Resources.

Monroeville, PA: PPG is hiring an experienced Ph.D. synthetic organic chemist for a position working on optical materials. 3+ years industry experience desired.

Cincinnati, OH: Well, that 55+ position B.S. chemist position I was talking about a week or two ago was posted on C&EN Jobs. Do I see that correctly that it is for $12.72/hour? Oh, dear.

Atlanta, GA: I have no idea what this UL technical manager position is about, although it probably has something to do with being an analytical chemist. Good luck!

Cincinnati, OH: Procter and Gamble is looking for a Ph.D. analytical chemist to be its atomic spectroscopy group leader.

Indianapolis, IN: Kelly Scientific posts a position for what can only be Dow Agrosciences; they desire a very specific kind of synthetic organic chemist:

Kelly Services is in need of Synthetic Organic Chemist to join the team at a top-tier agricultural company, located in the Indianapolis area.

Requirements: Must have Bachelor’s degree in Chemistry, along with up to 10 years relevant experience in an industry or research setting OR Master’s degree in Chemistry and up to 5 years experience in an industry or research setting. Prefer experience with Discovery Chemistry, or heterocyclic chemistry.

**Candidates with a PhD would be considered over qualified for the position**

Most of the time, posting B.S./M.S. or "senior research associate" would be enough to stave off the Ph.D. resumes. To me, this is more anecdotal evidence of a Ph.D. organic chemist surplus. 

A Modest Proposal: ACS Download Christmas/New Year's Jubilee

If you're an ACS member, that means that you get 25 free downloads of documents from ACS Publications. Some people (like me) use some of them for work, some don't.

The benefit runs out at the end of the year. Wouldn't it make sense for the benefit to carry over? Or, if not, wouldn't it make sense for a group of enterprising ACS members to congregate online and, say, burn through them before the end of the year? Just askin'. 

A good point by Freddie deBoer: the median, not the star student

Freddie deBoer is a humanities graduate student and a commentator on politics from a left perspective. He's been writing on-and-off on the myth of a STEM shortage and has an interesting point in Medium, looking at Silicon Valley's latest push for MOAR WORKERS (emphasis mine):

I was talking about this issue with a friend of mine, a brilliant PhD student in Electrical and Computer Engineering. We were walking by the quad during one of the big tech job fairs here at Purdue University, where some of the most powerful and profitable companies in science and technology come to entice Purdue students to apply for jobs. Purdue is a good school generally, but its reputation largely comes from its top-flight engineering and computer science programs. Looking at all of these billion-dollar companies spending time, money, and energy on developing elaborate booths, all to attract applications for employment, it was hard not to believe in the notion of a STEM shortage. 

When I mentioned that point to my friend, he laughed and said, “These companies are all trying to get the same 50 students.” This, more than anything, may be the source of the persistent STEM shortage myth: the inarguable value of being a star in a STEM field. There’s little doubt that people at the top of the food chain in computer science or electrical engineering or biomedical engineering, etc., often enjoy fantastic material and economic gain.  

But this is a banal point: it’s good to be a star. It’s good to be a star engineer in the same way it’s good to be a star musician or a star psychologist or a star writer. What public policy and politics demand is that we pay attention not to stars but to the median person. And the median American is facing a world of stagnant wages, the arbitrary nature of the employment market, and the constant fear of our financial system’s boom and bust cycle. The problem is that by definition, very few people get to be stars. I don’t doubt that the median Purdue STEM graduate is doing well. But Purdue is a top-flight STEM school, and half of our graduates will be below the median, and many who start those majors fail out of them, and the country is filled with schools who graduate STEM students who can’t get jobs. Basing our perception of the employment market on the outcomes of those 50 star students is pure folly.

I think Freddie's friend is probably right -- all those companies aren't trying to get warm bodies, they're trying to get star students. I think we've seen this with (my old nemesis) and Dow CEO Andrew Liveris, who was commenting about paying new chemical engineers $120,000 a year. Let's leave aside the question of whether or not it was accurate; it's likely that Dow has the money to chase the new star graduate and pay them a top salary, whatever the number. I wonder if those CEOs and their minions see what they're paying their new people and say, salaries are going up! We must have a shortage!

This doesn't excuse the behavior of the STEM shortage folks, but I wonder if it explains the nature of the distorted claims that they routinely make. 

Bonus Process Wednesday: The US Navy's newest chemical plant

From the Reuters wire comes news that the U.S. Navy is planning to actually be deploying the Field Deployable Hydrolysis System (that I had blogged about) on the MV Cape Ray to destroy Syria's nerve agents (emphasis mine):

The U.S. government has begun outfitting a ship in its reserve ready force with equipment to enable it to destroy some of Syria's chemical weapons at sea in the event Washington is asked to assist in the effort, a defense official said on Sunday. 

The Maritime Administration vessel MV Cape Ray is being equipped with the newly developed Field Deployable Hydrolysis System, which was designed by the Defense Department to neutralize components used in chemical weapons, a defense official said on condition of anonymity. 

The Organization for the Prohibition of Chemical Weapons, which supervising the disposal of Syria's chemical arms, said last week the United States had offered to destroy some of the components on a U.S. ship and was looking for a Mediterranean port where the work could be carried out.

Say, what's that boat ship doing over there? Oh, it's just neutralizing chemical weapons. (Does a Pfaudler warranty for a titanium reactor cover saltwater exposure?) The Washington Post says that 2 of the units will be installed on the Cape Ray.

(The Beeb has some nervous questions about it, specifically how Syria's chemical weapons are going to get from where they're stored now to the Cape Ray. Details, details.)

UPDATE: The Guardian says that a Danish ship will be used to transfer the chemical weapons from the harbor to the Cape May. Wow. 

Process Wednesday: Merck's prep-scale safety review

From the Organic Process Research and Development ASAP stream, a overview of Merck's internal reviews for safety at prep scale [1] (as defined as 500 grams to 5 kilograms). It partially stemmed from an incident with a serious hand injury with a diazonium salt: 

In 2009, the decision was made to formalize this process to complement the Pilot Plant review and better ensure the safety of all chemists running reactions on prep lab scale. An additional element of the new review process was a formal Hazardous Reaction Review, which applied to a much smaller scale than that employed in the prep laboratories. The necessity of this component was realized when a senior-level scientist in the department incurred a serious hand injury upon isolating a diazonium salt on less than 5 g scale.¹  

1. The published procedure he was following was somewhat ambiguous, only specifying not to use a metal spatula, with no indication of the serious hazards of isolating the diazonium salt. While scraping the material on the fritted funnel with a Teflon spatula, the material exploded, leaving the chemist with multiple lacerations requiring sutures to mend and nerve damage requiring surgery to fix.

The process to go to prep scale seems fairly methodical:

Prep lab scale is defined as reactions run in a vessel >5 L, even if the actual reaction volume is less. Note that the largest vessel size available for Merck prep lab use is 100 L. All prep lab scale experiments that involve a chemical reaction are covered by this policy. The policy requires the chemist to do the following prior to running the reaction: 

(a) Discuss with supervisor.
(b) Complete a “Paper Assessment”: Consult literature, Bretherick’s,3 MSDSs. Consider reaction type, functional group instabilities, known hazards.
(c) Chemistry Assessment: Complete probe reactions, documenting exotherms, addition times, cooling used,
workup procedures, etc.
(d) Acquire Differential Scanning Calorimeter (DSC) data on starting material(s) and product(s).4
(e) Submit completed “Reaction Review and Approval Form”.
(f) Obtain approval from both one SAC (Scientific Advisory Committee) designee and one EPSE (Environmental and Process Safety Engineering) designee before performing the experiment.

The authors note that they've found little delay using this process, with only one day's further testing on average. (They also note that more hazardous reactions have required longer turnaround times, which is understandable.)

The authors included some case studies with IBX, azide reactions and one (rather frightening-looking) decarboxylation, where an alternate route was found. Also, an example of a Blaise reaction, where the key to avoiding a runaway reaction was to look for reaction initiation, and not keep slowly adding starting material, if the chemist was not sure that the reaction had started:

A chemist experienced a runaway reaction at small scale when carrying out a Blaise reaction. EPSE found that this runaway can be easily reproduced if the bromoester is added rapidly. Calorimetry testing with slow addition showed that the decomposition was unusually vigorous, with an adiabatic ΔT of ∼200 K, and that there can be a delayed and autocatalytic initiation of the desired reaction. Approval was given to run this reaction on prep lab scale with the following provisions to prevent an overly vigorous delayed initiation: 

(1) After 3% of the acetate has been added, assay the batch for both consumption of starting material and formation of product (no quantitative assay was available for the intermediate). Do not add more acetate until confirming that the desired chemistry has been initiated.
(2) Repeat after the addition of acetate is 10% complete, and again after it is 40% complete.
(3) For deployment at pilot plant and manufacturing scale, investigate use of online instrumentation to monitor the reaction.

The last note I'll make about this paper is an interesting observation that I had not heard about aluminum pans in DSC measurements:

For safety screening, a special DSC cell that can withstand a significant amount of pressure is used. The standard crimped Al pan may leak at relatively low pressure, enabling the volatile components generated to escape the system. However, when a very rapid exothermic decomposition occurs at larger scale, the gases will often not have time to escape the system (even if it is not rated for pressure) before the remaining reaction mixture further reacts at higher temperature, which can lead to additional heat and pressure generation. In order to best balance resources and expertise, two to five chemists per research site were trained to run DSCs with the special cells. These cells are made of Hastelloy C rather than Al, as Al
reacts with many chemicals, thereby generating false positive or false negative results.

I don't think our pans are aluminum, but I had not heard that aluminum pans can deliver false positives or negative. Huh.

All in all, a worthwhile read.

1. Bassan, E.,Ruck, R.T.; Dienemann, E.; Emerson, K.M.; Humphrey, G.M.; Raheem, I.T.; Tschaen, D.M.; Vickery, T.P.; Wood, H.B.; Yasuda, N. "Merck’s Reaction Review Policy: An Exercise in Process Safety." Org. Process. Res. Dev., 2013, ASAP. doi: dx.doi.org/10.1021/op4002033

Ask CJ: How does a US-based B.S. chemist find a job in Germany?

From the inbox, a really interesting question (redacted to protect anonymity) 

I am beginning my search for a chemical related job in Germany. I graduated with a B.S. in Chemistry from [a well-known state university in the U.S.], and will be graduating in May 2014 with a Masters in [field related to biomedicine, etc.] I have good analytical chemistry based research experience along with a very good working knowledge of how American hospital emergency departments work as I have worked in one for about a year. I am very committed to learning German, which I began about one month ago. 

Since I will be graduating with my masters in May of 2014, do you have any recommendations on how to search/find potential employees who will take me beginning around June 2014? I have been doing research on the internet, and have found a few jobs which want to hire immediately, but I have not found any information on how to find a job for a few months in advance.

Most of the e-mail requests I get are from international readers, asking "How do I get a job in the US?", not the other way around. So, I suppose the questions that our reader is asking is:

• Where should I look for chemistry jobs in Germany? 
• How far in advance can I apply for these jobs? 

I have a few questions of my own, the main one being: what is the experience of the readership in getting hired in chemistry in Germany? How does it work, being an non-German citizen? 

Job posting: formulation chemists, Toronto/Guelph, Ontario

From the inbox, formulation chemist positions at Vive Crop Protection, a junior and a senior one. First position desires 3-5 years in the field, the second one requires a minimum of 5-8 years in a related field.

Here's one of the job descriptions:

We are looking for a Chemist – Formulations. The Chemist is part of the formulations research team and reports to a Senior Chemist and/or Team Lead. This position provides technical support of the company’s product development by conducting experiments, performing research and development activities and reporting on performance and results. This is a bench position helping development of new aqueous particle-based formulations of agricultural active ingredients.

Click on the links above for the contact e-mails. Good luck! 

Daily Pump Trap: 12/3/13 edition

Good morning! Between November 26 and December 3, there were 48 new positions posted on the C&EN Jobs website. Of these, 26 (54%) were academically connected and 10 (21%) were from Kelly Scientific Resources. 

Seattle, WA: Seattle Genetics looking for a B.S./M.S. senior research associate in process chemistry, 3-8 years experience desired.

Monroeville, PA: Axiall Corporation desires a Ph.D. inorganic chemist with 5-10 years experience for a Development Chemist II position; looks to be related to water treatment research.

Makeup?: Cosmopolitan USA is looking for a consulting colloid/surface chemist; $75-150/hr consulting rate?

Shamrock Technologies is back!: Not looking for a Scientist Friday this time, but still writing the ads floridly, desiring a lab tech. $35-45/hr, not bad.

Wilmington, NC: Gotta love this ad for Next Glass for a LC/MS chemist (M.S./Ph.D., 5+ years exp.):

Next Glass, Inc. (www.nextglass.co), is a Wilmington, NC-based company developing a wine and beer recommendation engine application (think Pandora for wine and beer).  The company is seeking a Senior Analytical Chemist excited about the prospect of creating methods for, and overseeing the testing of, 20,000+ plus bottles of wine and beer using a Thermo Fisher Benchtop Orbitrap Exactive LC-MS system, as well as other instruments.  The Next Glass team loves hard-working team players who want to contribute to demystifying the wine and beer selection process! 

Compensation: We pay top-dollar salaries (competitive with the pharma industry for Analytical Chemists) to attract “A” players.  The stock options aren’t bad either! 

Benefits: Family Health Insurance • Gym Membership • Fully-stocked Pantry • Lunches on Next Glass (you choose where, Monday - Friday) • $50/month for Wine and Beer Exploration • Unlimited Vacation • Massage Wednesdays • Company Credit Card

If this is really true, this is a great job for someone (or a potential way to earn yourself a sobriety coin.) 

Ivory Filter Flask: 12/3/13

Good morning! Between November 26 and December 2, there were 26 academic positions posted on C&EN Jobs. The numbers:

Postdocs: 0
Tenure-track: 18
Temporary faculty: 2
Lecturers: 4
Staff: 1
US/non-US: 21/5

Akron, OH: Looks like the University of Akron's college of polymer science and engineer is looking for a new dean. Wonder who they'll choose? 

Fairbanks, AK: The University of Alaska-Fairbanks desires two assistant professors of organic chemistry. 

Cookeville, TN: Tennessee Technical University, hiring an assistant professor of biochemistry. 

ست وظائف!: The Qatar University College of Arts and Sciences is hiring half a chemistry department, it seems, with plenty of lecturer and tenure-track positions. Good luck! 

C&EN on contract employees

C&EN's Linda Wang does an impressive job, as usual, in getting people to talk frankly about temporary/contract employment in the pharmaceutical industry. The article starts off with a terrible (and terribly common) anecdote: 

After being laid off in 2010 from the pharmaceutical company Roche, where he had worked for nearly 14 years, Paul Oleas thought it would only be a matter of time before he found another permanent position. 

But after six months of searching, and no full-time opportunities in sight, the pharmaceutical chemist accepted a six-month contract position with MAP Pharmaceuticals. At the end of the contract, Oleas was offered a full-time position. His relief was short-lived, however, as the company was acquired by Allergan, and Oleas was laid off again. 

Oleas is now in his third short-term contract position in as many years, and he’s accepted the possibility that he may never attain the sense of permanency he once had. “You have to roll with the punches,” he says. “And you have to try to make the best out of it that you can.”

Interesting comments on people with contigent positions:

Within the American Chemical Society membership, roughly 3% of industrial members who responded to the 2013 ACS Comprehensive Salary & Employment Survey reported being in a temporary or fixed-term contract position (C&EN, Sept. 23, page 9). Although this percentage has stayed relatively flat in recent years, new graduates, with a current unemployment rate of more than 12%, may in fact experience a higher rate of temporary work, says Gareth Edwards, senior research associate in the ACS Research & Brand Strategy department. 

Gold says that five years ago, Fairway Consulting Group wasn’t involved in providing contractors, only full-time employees. Now, he says, filling these positions brings in 15–20% of the company’s revenue. 

Similarly, Marc Miller, senior director of medicinal and process chemistry at life sciences recruiting firm Klein Hersh International, has seen an uptick in contract and temporary hiring. Approximately 20–25% of the firm’s placements are for contract positions, and he anticipates that percentage will grow. “I think you’ll see it move toward almost a 50-50 split between permanent and contract hiring into 2014 and 2015,” he says.

What is weird about contract positions is that my impression is that they are paid lower, not higher than full-time positions. You would think (and for some organization (i.e. hospital nurses), it is) that this would not be true, that the temps make more money to compensate them for taking on a more contingent position. That doesn't seem to be the case in the pharmaceutical industry, although perhaps I am wrong.

The professor quoted in the article echoes my concerns fully:

The growth of a contingent workforce worries Erin Hatton, an assistant professor of sociology at the University at Buffalo, SUNY, and author of the book “The Temp Economy: From Kelly Girls to Permatemps in Postwar America.” “Not only do these jobs not offer any sense of job security, these jobs also pay lower wages and offer worse benefits,” she says. 

Permanent employees could also be affected by the rise of contingent workers, Hatton says. “When workers are worried about being replaced by contingent employees, they’re more willing to accept lower wages and worse benefits packages.”

Quite so. Thanks to Linda for a worthwhile article, if a bit depressing. Best wishes to the permatemps, and to all of us. 

This week's C&EN

Little tidbits in this week's C&EN:

• Worthwhile article by Celia Arnaud on pre-eclampsia early detection.
• Dow pulls out of battery collaboration -- does anyone remember the brief bump in hiring for battery manufacturers in 2009 or 2010? (article by Melody Bomgardner)
• Maureen Rouhi talks about Kennedy's moon shot speech -- I didn't realize how specific he got. 

Happy (early) Thanksgiving!

Here we are again at another Thanksgiving (well, tomorrow, anyway). Once again, I am incredibly thankful to be part of an excellent chemistry blogging/Tweeting community.

To the people who read and comment on this blog, I am so incredibly thankful for each and every one of you. Your clicks, comments, tweets, and e-mails (especially the skeptical ones!) give me motivation and joy.

If you are in the US, may you and your family have a wonderful, happy Thanksgiving.

(And if you're not in the US, may you and your family have a wonderful, happy Thursday/Friday. Back Monday.)

Note on TMS diazomethane

Thanks to a tweet last night, I was reminded of the death of chemist Roland Daigle in 2009. Unbeknownst to me (even though I remember reading Jyllian Kemsley's article on the fines of Sepracor Canada that resulted from his death), there was a Clinical Toxicology report on what happened, including scale. I reproduce it here as a public service to chemists:

Fatal Occupational Exposure to Trimethylsilyl-Diazomethane 

Murphy NG,¹ Varney SM,² Tallon JM,¹ Thompson JR,¹ Blanc PD.³ 

¹IWK Regional Poison Centre, Halifax, NS, Canada; ²Rocky Mountain Poison & Drug Center-Denver Health, Denver, CO, USA; ³Division of Occupational and Environmental Medicine, UCSF, San Francisco, CA, USA. 

Background: Diazomethane (DM) is a highly explosive, toxic methylating reagent causing severe pulmonary injury. Trimethylsilyl-diazomethane (TSDM) is a less explosive analogue that may not be less toxic. We describe the first documented case of a fatality following TSDM exposure. 

Case report: A 46 year-old male pharmaceutical chemist presented to the ED with progressive dyspnea. At noon on the prior day, as part of a chemical analysis, he had mixed 2 mL of acetone with 25 mL of L-Malic acid to which was added TSDM dissolved in n-hexane. After 1 hour this mix was combined with an inert gas and a small amount of methylene chloride under a fume hood that was later reported to be nonfunctioning. 

Although he experienced no immediate mucous membrane irritation, 8 hours post-exposure he developed cough, pleuritic chest pain, hemoptysis, and progressive shortness of breath; by 15 hours, he presented to the ED in respiratory distress, hypoxic (PaO2 67), hypercarbic (PaCO2 46), and acidemic (pH 7.26). A chest radiograph showed an acute lung injury pattern. By 23 hours he required intubation. 

At 26 hours postexposure he developed profound bradycardia, refractory hypotension, and asystole. 

Case discussion: DM inhalation is known to cause fatal pulmonary edema without an immediate irritant prodrome and with a similar time course to this case. Structural modification of DM with an added trimethylsilyl group makes TSDM less explosive, but its propensity for lung injury is unclear. The chemical admixture as described in this case may have liberated nitrogen gas, but this should not have led to pulmonary injury; nitrogen dioxide should not have evolved. The toxicity may stem from residual DM present in the reagent or a direct effect of TSDM, its metabolites or breakdown products, or potential intracellular formaldehyde formation. 

Conclusion: The temporal relationship to exposure with inadequate ventilation and clinical effects similar to the analogue toxicant DM support a causal relationship between TSDM and acute lung injury. Additional safety data for this chemical is warranted, including experimental inhalation testing in animals.

The conclusion that I draw from this is not that chemists should not use TMS-diazomethane, but that they should exercise due caution with respect to the potentially fatal consequences of inhaling it. Work practices, engineering controls and PPE are all a part of that.

(Does anyone wonder if there's a misreporting of the scale of whatever test Mr. Daigle was performing? 2 mL of acetone and 25 mL (?) of malic acid does not make a ton of sense.)