Process Wednesday: Claisen's alkali

It's time again for another one of Kilomentor's questions. He asks of a potential process chemist:

24. What is Claisen’s alkali? For what separations can it be used?

Well, according to Purification of Laboratory Chemicals (a useful text if there ever was one (and it's free right now to Division of Organic Chemistry members!)), it's a water/methanol solution of KOH. As for its uses, it's probably Kilomentor himself who should answer that question:

Phenols may be separable from neutral substances by liquid/liquid extraction with aq. base, if the molecular weight is not too high. This is not a guaranteed success because phenols are only weak acids and the alkali phenolate, particularly as the molecular weight increases, may simply be water insoluble. Because the free phenol in this situation is lipophilic, the phenolate in the presence of both water and an organic phase may substantially hydrolyse back to sodium hydroxide and the free phenol. the neutral phenol “happily” jumps into the organic layer. For example, if a 10 ml. solution of 0.01 mol of 2,4-dimethylphenol is reacted with one equivalent of alkali in water and is then shaken with 20 ml of ethyl ether for about 10 minutes, the amount of the phenol found in the ether is 43% and the water is strongly basic. The amount extracted depends upon the ratio of alkali to phenol, the ratio of the phases, and the particular organic solvent used. In the case of 2-isopropyl-5-methyl-phenol (thymol) the amounts extracted by different solvents under the above conditions are: ether, 88; benzene, 38; carbon tetrachloride, 25; and pet. ether 22 percent. 

In the extreme case of di-ortho substituted phenols there is steric hindrance to the solvation shell that is needed around the oxygen anion, which makes the anion formation energetically disfavoured. With di-ortho phenols, even when the molecular weight is rather low- the phenol will not dissolve in aqueous sodium hydroxide. For that reason such species were called cryptophenols in the days before spectroscopic testing, because these phenols did not give the characteristic qualitative test for a phenol. Cryptophenols can be dissolved in methanolic-KOH called Claisen’s alkali. 

So I suspect that Claisen's alkali can be used in the extraction of phenols and other somewhat acidic functional groups (carboxylic acids) from fairly non-polar solvents? I confess, I'm not completely sure on this one.  

2010 ACS ChemCensus: Industrial salary quintiles, inequality

Among the interesting tidbits that the ChemCensus brings is the full-time industrial chemist salary quintiles. I'll just let you sit and read that table. For my industrial readers, of course, there will be the natural tendency to look at how your salary compares to that of your fellow chemists.

But what I'm most interested in is the change over time of the top, median and bottom salaries between the 2010 ChemCensus and the 2005 ChemCensus. With that in mind, I've prepared a Google document that indicates the change between the 90th, 50th and 10th percentiles in the last 5 years for B.S., M.S. and Ph.D. chemists that are 20-24 years after their bachelor's degree. That amount of experience was basically chosen at random -- readers can disagree about the variables that introduces or excludes.

It appears to me that, over the past 5 years, the 90th percentile of chemist salaries is pulling away from the 10th percentile of chemists. The fall in the 10th percentile of chemist salaries is perhaps shocking.

I note that 1) I don't know if my calculations are correct, 2) if correct, what it means and what should be done (if anything?) about it. I find it fascinating that the median salaries have actually increased healthily (noting, of course, that the 90th percentile is doing even better, with the exception of M.S. chemists. Huh?) I think I need more data.

Readers, what do you think? 

A good start

3 years ago today.

I'm on record saying that that I'd like to blog at least "until this unemployment thing comes around." (2nd to last paragraph) Considering that doesn't really look like it's going to happen anytime soon, I guess you all are stuck with me.

Thank you so much for reading, commenting, e-mailing, correcting me, critiquing me, Tweeting and linking.

Daily Pump Trap: 12/13/11 edition

Good morning! Between December 8 and December 12, there were 27 new positions posted on the ACS Careers website. Of these, 9 (33%) were academically connected.

Andover, MA: Cambridge Isotopes is hiring B.S. chemists with 2-4 years of experience for batch synthesis of isotopically-labeled compounds. Not exactly a growth field, but nice to hear. GMP experience desirable.

And in other news: Cambridge Isotopes is hiring a Ph.D. analytical/organic chemist for a senior QC chemist position.

Similarly named...: Cambridge Major Laboratories (in Germantown, WI, I believe) is hiring B.S./M.S. analytical chemists and a Ph.D. analytical chemist for a senior regulatory position. (Scroll down, past the 2nd shift operator position.)

Cheese: The Hilmar Cheese Company (Hilmar, CA) is looking for a M.S./Ph.D. research chemist for research and quality control work. Apart from the typical chemist requirements, you need a "[b]asic knowledge of dairy chemistry, specifically in the field of dairy protein and lactose chemistry."

Zeroes!: Agrium Agriculure Technologies (Sycalauga, AL) is looking for a Ph.D. chemist (0-5 years experience) to become a product development chemist; the company appears to make fertilizers and other products for agriculture.

Saskatchewan!: For my readers north of the border, the government of Saskatchewan would like to hire a B.S. chemist to be a hazardous materials/spill Environmental Project Officer; you will be based in Regina, Saskatoon or Prince Albert. I'm going to guess that this is a pretty thankless position, really, considering that you're going to be trying to keep the potash industry from doing the wrong environmental thing.

Ann Arbor, MI: Wacker Chemicals is looking for a M.S./Ph.D. chemist to be a production manager for their silicone/silica-based business. 5+ years experience.

Albuquerque, NM: Sandia National Laboratories is looking for a B.S. chemist to be an electrochemical technologist. Curious what the pay level for this is.

AMRI/Lilly: When should public shaming of execs start?

Can anyone give a defense of either AMRI or Lilly in this (IMHO) execrable "AMRI at Lilly" deal? I suppose it's "hey, we could just not hire anyone." I find this whole thing odious.

That said, here are the links to the 20 new B.S./M.S. positions and the 14 experienced (2-5 years) B.S./M.S. positions being advertised. 

At what point do we as a community of chemists start advocating public shaming of managers/executives who put together these deals? Are there lines to be drawn? Have they already been crossed?

Best wishes to us all. 

2010 ChemCensus is out: not much good news.

Credit: Chemical and Engineering News

The results of the ACS ChemCensus that was held in 2010 is out in this week's issue of Chemical and Engineering News in the writeup by David Hanson.

It's going to take a while to wade through all the data, but here are the important details (to me, anyway):

• Reported salaries were all down, with the exception of median B.S. chemist salaries. 
• As we've known for a while, the unemployment rate of all respondents in March 2010 was 3.8%, which is 0.1% lower than 2009. That 2009 was a 20-year high for the ACS Salary Survey. 
• The "U6-like" number for the ACS Salary Survey data (including part-time, post-doc and unemployed) is the highest in ten years, at 11.9%. Hanson notes the other side of this statistic, the lowest full-time employment of chemists since at least 2010. I'll note that I predicted a U6-like number at 12% way back in 2009. Good to know I'm only a year late. 
• Unemployment is negatively correlated with education, with B.S. chemists at 5.1% unemployment and Ph.D. chemists at 3.2%. M.S. chemists (the legendary 'most employable') come in at 4.8%. 
• The "ten year" rule still holds; among age cohorts, the 30-39 age group has the lowest unemployment at 2.5% and the 40-49 age group jumps to 3.6%. The bad news isn't over yet -- the 50-59 age group has the highest unemployment at 4.7%. This is lower than 2009's 5.0%, but not by much. 
• I note that the "small company discount" is alive and well. Median Ph.D. salary for a company of 10 or fewer employees? $49,200. Median Ph.D. salary for a company of 11-20 employees? $86,200. That's close to a 50% discount. Wow. 

More soon. Readers, here's the article. What do you see? 

The Eka-Silicon caveat: The ACS Salary Survey and the ChemCensus have both had relatively low response rates from members, which limits the extrapolatability of the data. This year's response rate for the ChemCensus was 47%, which is much lower than the 80% that professional survey types like to see. A discussion of this can be found here. At the same time, ACS unemployment numbers for their members more-or-less track the BLS survey data for chemists (see linked graph). 

One more thing: All of the 40,480 responses were hand-entered by the ACS' Deparment of Research and Member Insights. Research associate Gareth Edwards (I believe) was responsible for much of that. This is a huge undertaking, and he should be commended for it. 

[Ding ding ding] Could I have your attention, please?

...It's been a tough year at PharmaCorp and I just wanted to say a few words...

(Thanks to lurkertech's Buzzword Bingo generator)

Who's the Albert Pujols of pharmaceutical chemistry?

Oh, Pujols! Credit: Wikipedia

Albert Pujols was a star first baseman for the St. Louis Cardinals. After winning his second World Series with the Cardinals this fall, he decided to sign with the California Anaheim Los Angeles Angels of Anaheim for 254 million dollars. (Sorry, Cardinals fans -- I feel for ya.) 

I'm relatively unaware of any pharmaceutical process or medicinal chemistry departments that have made similarly large personnel moves, even in the good ol' days. I'm sure there were many behind the scenes maneuverings back in the day, with directors moving from company to company, bringing along their best lieutenants. I'm going to guess such moves just don't happen these days. 

By contrast, there always seems to be a veritable "hot stove league" of chemistry professors moving from department to department. While I'm sure that those older and wiser than I can name even older precedents, the move of Peter Schultz to Scripps seems to have been accompanied by a significant financial commitment to building laboratories, etc. People have followed the move of John Hartwig from Yale to Illinois to Cal with some amusement.* 

Readers, any stories of the good ol' days of pharma and big personnel moves? (other than mass layoffs, that is

*Sincere condolences for those who have to pack up the gloveboxes and put them on the moving trucks. It seems that professors never seem to hire movers for that sort of thing.

Arrrrrrrrrrrgggggghhhh! CEOs and their broad-brush employment statements

An irritating set of statements from CEOs gathered before a informal Congressional panel:

“It’s really disappointing for companies like mine, when every single headline is about joblessness, to know that there are actually hundreds of thousands of jobs that are going without being filled,” said Lisa Hook, CEO of Neustar Inc., a Sterling, Va.-based telecommunications company. “Get me qualified people, and we’re taking qualified applications in the back of the room,” she added, drawing a round of laughter from the congresswomen and audience. “Because we never miss an opportunity.” “It’s incredibly challenging to get good technical people,” said Alison Brown, CEO of Navsys Corp., a Colorado Springs, Colo.-based GPS technology company. “There’s an enormous amount of demand, there’s competition, quite frankly between industries and labs and federal institutes.”

Navsys appears to have 5 (five) openings on their website. Neustar appears to have 32 openings on their website. Job growth must be happening at other companies, I suppose.

We also get the huge conflation of the "S" with the "TEM". It seems like TEM jobs are well-paid and regularly looking for people, while there's plenty of labor supply of the "S" and relatively few openings.

The problem, the business leaders said, boils down to the dearth of qualified people with expertise in science, technology, engineering and math, collectively known as STEM. Hook, the telecommunications executive, ticked off what she called troubling statistics: By 2018, there will be 1.4 million computing job openings in the United States, but given graduation rates, only 29 percent of those jobs will be filled by U.S. graduates; 40 states produce fewer computing graduates than needed to fill projected openings in their states; and the number of girls studying computing has declined 13 percent in the past 10 years. 

The statistics come from the National Center for Women & Information Technology, which culled the numbers from various government departments. “We need a lot of federal assistance in encouraging children to go into STEM, we need to make it accessible and available starting in the ninth grade,” Hook said.

Nothing quite like lobbying Congress to cut your business costs -- sigh.

I think my opprobrium is best held for Ms. Janet Trautwein, who exemplifies every irritating HR manager in the history of corporate America:

Not all the CEOs at Monday’s panel need STEM graduates for their companies. Echoing some of her colleagues, Janet Trautwein, head of the National Association of Health Underwriters, said her professional association has many more applicants that it has jobs to offer. And she had some bad news for overqualified workers. “I do have a lot of people applying for positions that are really entry-level positions with way too much experience, and frankly I can’t hire [them] for those positions because I can’t pay them what they need, and also they won’t like it,” she said. “They wouldn’t be satisfied with that.” 

After the panel, Trautwein said she had hired highly experienced people for low-level positions, only to have them quit two months later. Her advice to people applying to jobs for which they are overqualified: Explain yourself up front, either in the cover letter, or at the beginning of the interview, and make a case for why you are willing to take a position far beneath your skill level.

Sowhatyou'resayingis, people need to drop their dignity and grovel a little harder. 

Daily Pump Trap: 12/8/11 edition

Good morning! Between December 6 and December 7, there were 12 new positions posted on the ACS Careers website. Of these, 6 (50%) were academically connected.

Adhesives!: Adhesives Research, Inc. is once again looking for a M.S./Ph.D. chemist with experience  "in the formulation and synthesis of pressure sensitive and laminating adhesives." You'll be working in the industrial tape division -- it's kind of amusing to learn that there is such a thing.

Ink!: DuPont is looking for a M.S./Ph.D. chemist for a technical supervisor position in their photovoltaic ink section (?); 5+ years experience in the chemical industry, with QA experience is desired.

Glass!: Solutia is a company that makes the polymer layer in safety glass; they're looking for a Ph.D. organic/polymer chemist to perform R&D for them.

A broader look: Monster, Careerbuilder, Indeed and USAjobs.gov show (respectively) 247, 676, 3025 and 40 positions for the search term "chemist." 

Sometimes it feels this way, doesn't it?

Parody of this parody by HeyOkay.com

This is not really how I feel. (mostly)

Process Wednesday: TLC

One thing that I love about Organic Process Research and Development is the editorials by Trevor Laird. I suspect that Dr. Laird has been proto-chemblogging since 2000 or so. A bit of a gem on the organic chemist's favorite bench-scale analytical technique [1]:

I had finished my Ph.D. in 1970 and worked for many years in industry before the technique of HPLC became routinely used: first, in the analytical laboratory and subsequently by process chemists as a tool for following reactions as well as analysing products. I still remember the days when TLC was used, not just for qualitative analysis but also for accurate quantitative analysis of finished APIs. It is still useds in its HPTLC modes by some companies, particularly in Germany, as an accurate quantitative method of analysis, but the technique has been forgotten as a quantitative method by many younger chemists.  

TLC has some major advantages over HPLCs -- cost being an important one. This means that it can be used in all circumstances, such as on the manufacturing plant. Since it is simple to use, process operators can easily perform the technique accurately. The second major advantage is that you see everything -- if you use correct visualisation (spraying and heating as well as UV visualisation) whereas with HPLC it is possible for impurities either to be retained on the column or to be late eluters which impatient organic chemists, but hopefully not analysts, might miss. 

On a consultancy project in which I was recently involved, TLC was the only way in which a particular impurity could be detected and quantified. It is a useful adjunct -- or a reality check -- to HPLC in many instances. 

[snip] So those of you who have abandoned TLC -- particularly quantitative TLC -- in favour of only HPLC, remember that TLC also can mean: The Lowest Cost.

I'm intrigued by the concept of having process operators perform TLC in the manufacturing plant; I think it's doable, but I think it would take a good bit of training to have relatively new operators correctly interpret TLCs. 

1. Laird, T. Org. Process. Res. Dev. 2006, 10, 1. 

Finding a job/postdoc during graduate school

In the recent reader request thread, MB writes: 

As a young graduate student, I would love some advice on how and when to participate in certain "career milestones" so that I can at least be proactive about my job prospects later on. For instance, if I want to pursue an academic career, what should I be doing at certain points in graduate school, at what point should I start thinking about post-docs, when should I apply for them, and how should I go about finding them, etc, and how does this compare to an industrial route? Once graduate school is done, how can I put myself in the best position not to be unemployed? We see a lot of forecasting on this blog and a lot of "what to do after the fact," but I would find it really useful to have some perspective on how to pre-empt some of these issues.

There's a lot of good questions in there. The basic gist is this: you need to start preparing for post-graduate school employment at least a year in advance, if not more. 

If you want to go the academic route, I believe that you're supposed to send your application package (cover letter, CV, research summary) to your professor a year before you'd like be there. (This means, of course, that you need to have a decent idea of when you're done with your thesis, when your committee is agreeable for you to defend, etc.) It also means that you need to have to have accomplished something of substance by that point; a couple of papers' worth of material is probably a nice minimum goal to shoot for, although some of our more august readers will probably say that you need more. 

For the industrial route, there's probably not too much difference between what I've laid out for the academic route. That said, larger companies tend to hire on a cycle that starts with campus interviews and other applications in the autumn and ends up with site interviews (and hiring!) in the winter and spring.* The academics tend to go off of a "rolling admissions" basis, to borrow a phrase from the undergraduate admissions world. 

Readers, what do you think of my recommendations? What would you recommend to MB? 

*That also means (for site interviews) that you need to be able to give a 45 minute presentation on your work. 

Daily Pump Trap: 12/6/11 edition

Good morning! Between December 1 and December 5, there were 311 new positions posted on the ACS Careers website. Of these, 14 (5%) were academically connected.

West Chicago, IL: Blachford, Inc. is a company that makes noise absorbers from polymers; they're looking for a B.S. chemist with 1 year of laboratory experience. Polymer chemistry coursework is "essential"; sounds interesting.

York, PA: Adhesives Research, Inc. is a company that develops adhesives for the medical device and pharmaceutical worlds. They're looking for a M.S. chemist with a background in polymer analysis.

Well, then, sign me up!: The American University in Beirut, Lebanon is looking for a non-tenure-track professor of analytical chemistry.

Kelly: Holy Kelly, folks. 281 (90%) positions posted by Kelly Scientific Resources, the majority of them chemistry and/or tech-related. There's a few synthetic positions buried in there -- looks like Dow Agrosciences in Indy is hiring temps now.

China Corner: Haisco Pharmaceutical Group (located in sunny Chengdu, China) is hiring, well, everyone. Synthetic organic chemists welcome, too. 

Great analysis of UK chemistry grads' fate

over at Lab Monkey For Hire's. I'm posting (stealing!) the best graphic here:

I should really attempt one for ACS data -- I think it might be a little more difficult to develop, but we'll see. 

Chemistry Nobelists doing their prize-winning work later

Credit: Chemical and Engineering News

From this week's Chemical and Engineering News, an article by Bethany Halford on the productive years of Nobel-winning chemists:

"According to a study by economists Benjamin F. Jones, of Northwestern University, and Bruce A. Weinberg, of Ohio State University, the average age at which Nobel Laureates in Physiology or Medicine, Physics, and Chemistry do their prizewinning work is on the rise (Proc. Natl. Acad. Sci. USA, DOI: 10.1073/pnas.1102895108) More than half of the Nobel Laureates in Chemistry from 1901 to 1960 did their prizewinning work by the time they were 40. Since 1961, prizewinners were more likely to have done their acclaimed work after their 40th birthday. 

At first blush, Jones and Weinberg’s study may seem like good news for researchers who don’t have to think of themselves as past their prime just because they’re past their 40th birthday. But Jones tells C&EN that the implication of his finding is a bit less rosy: Scientist may be spending their most creative years being trained, as doctoral students and as postdocs, rather than doing their own innovative research. 

“There’s a long-standing view that people are at their most productive as innovators early in their life cycle,” Jones says. But, he points out, if it’s true that people have to become experts before they can innovate, then scientists are spending more of their years training and less of their time innovating. Consequently, their lifetime contributions as scholars are going to be smaller. Jones estimates the decline in a given researcher’s career output is as high as 30%."

I used to have a biochemistry professor who would mutter to his classes, when covering a fundamental topic, "...And Professor X won the Nobel Prize for this -- shows how little you had to do to win the Nobel Prize back then..."

I'm reminded of him when you look at the graph -- it's fairly obvious that there was either 1) a couple generations of geniuses from 1921 to 1960 or 2) lots of fundamental discoveries to be made at that time.

Presumably, there are ways of short-circuiting the graduate education process to give especially talented researchers access to funding for their ideas sooner rather that later. But that's no guarantee, I suspect, that the next block on that graph won't see the yellow bar get bigger or the red bar get smaller...

Ring clamps

A list of small, useful things (links):

• David (and Deborah Blum!) on pepper spray
• Excimer has language issues.
• Adam's latest on the higher education bubble. (?)
• Th'Gaussling on the rare earth boom.  
• Dr. Freddy's self-portrait.
• An interesting contrast in opinions on work-life balance. 

A note to any bloggers out there -- want me to link to your post? Just e-mail me! 

See you on Monday!

Living and dying with your project? Hmmm....

Two readers have mentioned this interesting development at GSK:

Six months ago, Roberto Solari talked eagerly about his research into the mechanisms that govern asthma. Now he must let someone else finish the job.  

Solari, who until last month headed one of GlaxoSmithKline Plc (SAN)’s targeted research units, is one of the casualties of the company’s new approach to drug discovery. Chief Executive Officer Andrew Witty turned up the dial on an overhaul initiated by his predecessor after he took over in 2008, dividing six disease-focused research centers into smaller teams known as Discovery Performance Units. The teams, or DPUs, compete for funds bestowed every three years after a review. Those that fail to meet their targets may get disbanded. 

Solari, an unassuming 55-year-old scientist of Italian origin, is still working at the company and no longer heads the team, Morgan said. She declined to comment on the reasons for the change. So did Solari.

So what could possibly happen when you divide your company into little units that might have to compete for resources to keep their positions? Well, they compete for resources!:

Glaxo has been hunting for ways to encourage teams to cooperate, according to Vallance. One example, he says, is to give credit for inventing a molecule that gets picked up by another one of the company’s 38 DPUs. 

“We need to keep working on that because I think 38 silos is a disaster,” he said in a May 13 interview. “It’s not what we got, it’s not what I want. It’s not a sort of bear pit with everyone fighting each other.”

I cannot imagine the infighting that's resulting from this. I might note that the higher management seems to think that this is a good way of growing and picking good leaders of scientists. I'm a little skeptical. (Also, what's the likelihood that the executives will be facing a similar judgment?)

ACS Webinar: "How to Secure and Nurture a Vibrant Chemistry Career in the 21st Century"

ACS is hosting Brian Fahie, Senior Director, Analytical Science R&D, at Eli Lilly; he is responsible for Lilly’s global analytical efforts supporting small molecule active pharmaceutical ingredient (API) development.

He'll be talking about growing your career in the 21st century with Patricia Simpson, director of career services at UIUC's Department of Chemistry. 

The Layoff Project: "I feel frustrated that I cannot help anyone"

BQ is a longtime pharmaceutical chemist who writes in with their layoff story. [CJ's note: this story has been fairly heavily [redacted] to protect anonymity.]:

Previously, I had a terrific career at [large pharmaceutical company], where I was an organic/ medicinal chemist of excellent standing (going by what my associates think of me).  After stellar years (18+, in these times it is embarrassing to talk about your experience as it also speaks of your age!), [Large Pharma] separated from me (3 years back) and there were many other friends of mine in that list.  I have to say that [Large Pharma] treated me reasonably well (as opposed to other horror stories, I have heard) and as a matter of fact my boss accompanied me (his eyes were bloodshot, I recall) on that day of my departure to the exit gate.  That said, it does not take away the fact that, I was mad as hell.  I was angry for the simple reason that the years of training in several programs had given me an air of confidence (ahead of the curve in terms of understanding the science at the interface of biology, chemistry, ADME, DMPK etc.) and it felt good.  During those years at [Large Pharma], I had worked on and impacted on many programs that delivered varied molecules for clinical studies (Rheumatoid arthritis (Phase-2), Obesity (Phase-3), and a macrolide antibiotic, [redacted] for veterinary use).  Then there were other programs that petered out,  but important lessons were garnered.   Imagine my frustration, when I thought I could deliver lot more and then this parting happened.  In many ways I felt like, I was nipped off even before I fully bloomed.