An evening funny

Back tomorrow with more.

Stolen from synthesisman's post on the chemistry Reddit. I admit I heard this a couple of times in graduate school. 

Process Wednesday: Stopping at the right time

From a recent Org. Process Res. Dev. ASAP [1], a really great point about scaling up and reactions that are sensitive to side reactions. The authors had just developed a successful cyclization with 90% yield and 96% purity to produce 1.5 kilograms of material. And then...:

In order to test the robustness of this process, the reaction was extended for an additional 20 h. While the cyclization was complete within 2 h, the level of 18 increased almost linearly with reaction time, reaching 50% after 22 h at the expense of product 11, indicating that 18 was mainly generated from 11 (Figure 1a) [CJ's note: Left-hand graph above.] Thus, it became critical that the reaction be stopped at the right time point to minimize degradation, a challenge at plant scale. As the de-ethylation is likely acid catalyzed, base additives were considered to slow this process. The addition of 2,6-lutidine (2 equiv) was found to significantly retard the rate of the formation of 18 without a negative impact on the cyclization rate (Figure 1b) [center graph]  

Subsequently, an improved cyclization procedure was developed, using 1 equiv of p-toluenesulfonic acid (p-TSA) buffered with 3 equiv of pyridine as the catalyst and a Dean−Stark trap to remove water generated during the reaction. The cyclization of 10 was complete within 3 h, and 11 precipitated out from the reaction mixture as the p-TSA salt.  

More importantly, once the reaction was complete, no further decomposition of 11 to 18 was detected (Figure 2) [graph to right]; the levels of 11 and 18 remained essentially constant at 94% and 4%, respectively, even after heating the mixture to reflux for an additional 21 h. After cooling to room temperature, 11-TSA was isolated in 97% yield and 95.8% purity (containing 2.6% of 18). Material of this quality can be directly used in the next step. Interestingly, pyridine and p-TSA were found to be the ideal combination. Reactions catalyzed by p-TSA alone or with 2,6-lutidine in place of pyridine were observed to be slower and generated higher levels (4.8−8.8%) of 18.

I can't agree more about the difficulty of stopping a reaction at the right time. I think it's just very difficult to get that sort of thing to take place in a busy chemical manufacturing plant; it's much better to build that robustness in from the start.

1. Shu, L.; Gu, C.; Dong, Y.; Brinkman, R. "Efficient Large-Scale Synthesis of a 2,4,5-Triarylimidazoline MDM2 Antagonist." Org. Process Res. Dev. ASAP. DOI: dx.doi.org/10.1021/op300294g

Law school entrance exam takers dropping

Credit: The New York Times

From the New York Times' Economix blog, evidence of lowered interest in law degrees from Catherine Rampell:

The number of people taking the Law School Admission Test, known as the LSAT, offered in October fell sharply, down 16.4 percent from the year before, reaching its lowest level since 1999. October is usually the most popular time to take the test, too.  

No wonder, then, that law schools are cutting the size of their entering classes. Perhaps this means it’ll still be easier to get into the top schools, though, depending on how much the most elite schools decide to shrink their class sizes. 

There was a huge surge in law school applications during the recession and its immediate aftermath as people displaced by the poor economy sought the “safety” of a legal career. But now potential students seem to have wised up to the huge debt burden and poor job placement prospects.

I wonder if there's been similar evidence of smaller Ph.D. programs. I haven't heard any rumors of such, but there are other drivers of large entering grad student classes (demand for TAs, etc.)

Readers, what say you?

From the inbox: Novartis associate medchem position

From an astute reader, a position w/NIBR in Cambridge:

This position requires a B.S. or M.S. degree in Chemistry with at least 3 years experience in the synthesis and characterization of organic compounds. Experience with common spectroscopy (NMR, IR, UV, MS) and analytical techniques required. Experience with chromatography purification systems required. Good written and oral communication skills are required for effective drug discovery team participation. For faster consideration, please include your research summary as part of your resume.

Best of luck!  

Ask CJ: an immigration question

I recently received an e-mail from AS, who got a Ph.D. in chemistry in the US* and did a postdoc here as well, but through happenstance, is back in their home country in Eastern Europe. They're looking for ways to find industry jobs in the US or other countries. They have the following questions:

• Is there and difference in the difficulty level of finding employment for foreigners between US and Canada? 
• Alternatively, I can try to find another postdoc (which is something I am also working on). However, due to certain visa policies I can not return on the same academic visa I had previously. Do you happen to know if new or returning postdocs are admitted back in US on a temporary work visa? 

I confess to not being an science immigration expert, but I am sure there are some amongst my readers. It is my broad understanding that Canadian immigration is more biased towards skills-based (or $$-based) policies than those of the US, but I confess I don't really understand the issues.

Please comment, if you have expertise.

*At a very good department, not that it matters. 

Daily Pump Trap: 12/4/12 edition

Good morning! Between November 29 and December 3, there were 80 new positions posted on C&EN Jobs. Of these, 17 (21%) are academically connected and 51 (64%) are from Kelly Scientific Resources.

Philadelphia, PA: Heyyyyyy! How many chemists get to work for Delta Airlines? So a while back, Delta Airlines bought an oil refinery. And now, they're looking for a rotating-shift QC chemist:

This is a highly compensated entry level position requiring the individual to work on a rotating 12-hour shift that includes weekends and holidays. The Shift Chemist analyzes organic and inorganic compounds to determine chemical and physical properties utilizing such techniques as classic wet bench chemistry, chromatography, spectroscopy, spectrophotometry, and various physical property analytical techniques. This information is used in process control and for the certification of finished products.

0-5 years experience needed in a refinery/chemical plant area. Fascinating.

Kingsport, TN: BAE Systems is looking for a Ph.D. organic/organometallic chemist (or a B.S. chemist with 10+ years experience) with 5 years of energetic materials experience.

Plainview, NY: Certified Laboratories is looking for a M.S. analytical chemist to be an instrumentation manager with 10+ years experience in food safety. 

Birmingham, AL: Southern Research Institute is looking for a senior medicinal chemist with the experience/ability to garner grant funds.

Rockford, IL: A confidential rubber/tire company is looking for a QC manager; 45-55k desired.

Manchester, UK: Nanoco Technologies is doing thin film solar-oriented research; they're looking for, among others, synthetic and materials chemists. 

Ivory Filter Flask: 12/4/12 edition

Good morning! Between November 27 and December 3, there were 28 academically connected positions posted on C&EN Jobs. The numbers:

Total number of ads: 28
- Postdocs: 4
- Tenure-track faculty:  20
- Temporary faculty: 0
- Lecturer positions:  1
- Staff positions:  3
- US/non-US: 20/8

Pasadena, CA: The California Institute of Technology's Department of Applied Physics and Material Science is looking for an assistant professor.

St. Joseph, MO:  Missouri Western State University desires an assistant professor of biochemistry.

Gainesville, FL: The University of Florida's College of Engineering is looking for a new EH&S director; B.S./M.S. with 4-6 years relevant experience; 90-110k offered.

Orem, UT: And on the other end, Utah Valley University is looking for a chemical lab manager and a chemical hygiene & safety coordinator for 35k to 44k. Huh.

Newark, DE: The University of Delaware is looking for a organic laboratory manager; M.S./Ph.D. desired.

A morning project management laugh

Feel like this morning's posts have been bummers, so here's something amusing:

Dr. Freddy had an Ask Me Anything post recently. Here's part of his response to my question -- you'll have to go over there to read my NSFW* question, and the punch line:

There was this project which involved a super-active compound, according to the primary and cell assays, and met stab data were decent... So far however, they had only been able to isolate 6 of the enantiomers, so my assignment came to be to find the missing 2. Prio 1 and whatever they like to call it. 

I drew the compound on paper and started staring at it. That is my modus operandi. I stare problems down, if necessary for days. (I think it was Einstein who said something like: it’s not that I’m smarter than most people, I just tend to stay with problems longer.) After almost a full working day — my brain is pretty slow in 3D space — it suddenly struck me. A C2-symmetry element! There could only be 4 enantiomers!

 Seriously, the story gets better. Go over there and read it.

*I used a technical term for a project that is not going well. The Navy calls it a Charlie Fox, I believe. 

C&EN: Canadian government helping out Montreal R&D

It's hard not to see these two C&EN articles as somewhat
emblematic of the changes In These Times.* 

From this week's C&EN, an article by Lisa Jarvis talking about the Canadian government's effort to help out the struggling Montreal R&D scene:

As drug companies move their R&D operations out of Quebec in rapid succession, Canadian authorities are trying to sustain the region’s life sciences community. In the latest effort, the government, along with AstraZeneca and Pfizer, is committing $100 million over five years to establish the NeoMed Institute, a nonprofit research center in Montreal. 

NeoMed aspires to bridge the gap between basic research and early clinical studies for drug candidates by offering universities and biotech start-ups funding and services. The hope is to eventually restore some of the hundreds of R&D jobs the region has lost in the past two years. AstraZeneca and Pfizer, along with any other big pharma partners that join NeoMed, will have an option to license molecules developed there. 

AstraZeneca is kicking in its former neuroscience research facility, which was focused on developing small molecules, along with $5 million and intellectual property for three potential pain drugs. The firm values its input at $35 million...

...The research center will provide minimal relief for the victims of pharma-related R&D job losses in the Montreal region. In addition to AstraZeneca, Merck & Co., Johnson & Johnson, and Boehringer Ingelheim all have shuttered R&D sites or significantly cut the number of scientists they employ in Quebec.

Someone (myself?) should track where all these chemists that used to work in the Montreal region have ended up; this is really unfortunate, and does not bode well for pharma R&D in Canada.

Best wishes to all of us.

*Not intending offense to Nigerians or Indians, just noting the choices that multinational pharma R&D is making. 

While we're at it...

Any materials scientists out there? I have a question regarding a specific department of materials science. If you want to opine on this department (located in the northeast region of the US), please feel free to e-mail me at chemjobber -at- gmail/dot/com. 

C&EN: Opportunities in materials science

From this week's C&EN, a look at career opportunities in materials science by Shawna Williams:

The numbers bear this out: The U.S. Bureau of Labor Statistics (BLS) projects that the materials science field will grow by just over 10%—around 900 jobs—between 2010 and 2020, compared with 4% growth in chemistry jobs. But delving deeper into the BLS numbers, it’s clear there’s a significant shift under way in the field, with consulting, research and development, and academic positions on the rise, while most jobs in manufacturing are expected to decline. 

Despite these changes, and the weak economy, heads of materials science departments around the country report that their graduates have, by and large, continued to find employment in recent years....  

[snip] Today, some of the hottest areas are gallium nitride and its role in solid-state lighting; oxide semiconductors, which hold promise for electronics; hybrid structures of organic and inorganic components, which are ultralightweight or have unusual mechanical, thermal, or energetic properties; additive manufacturing, in which products are made in layers by a printerlike machine; and energy-related materials such as organic photovoltaics and thermoelectrics, according to UCSB’s Pollock. 

Dow Corning is looking to fill positions in specialties such as ceramics, solid-state chemistry, and metallurgy, according to Michele Stafford, a recruiter with the firm. In addition, she says, “we have a large need for materials scientists who have a focus on doing device development. Not only would they synthesize the materials, but they would look at how those materials fit into electronic devices.”  

The competition among companies for scientists with the right backgrounds—whether they’re old hands or newly minted Ph.D.s—is quite stiff, says Dow Corning’s recruiting manager for North America, Jason Saavedra. In response, many firms partner with universities and offer internships to cultivate relationships with students doing research in desired areas, he says.

Not to be particularly repetitive on this point, but I find it amusing and irritating that department heads cannot simply tell Ms. Williams what the employment rate of their graduates is.

(I wonder who Dow Corning is working with?)

Age discrimination in pharma discussion

An important discussion on age discrimination in pharma is going on below, if you should choose to join in. 

Thank you note etiquette

Because I can't send each and every one of 
you a thank you note, I've appended one above. 

I've also typed it out for comparison. 

I am a big believer in writing 'thank you' notes (by e-mail or in person.) I also think that it's important for job candidates to send thank you notes after on-site interviews. After a long discussion recently elsewhere online*, it seemed like the general consensus was:

• Send an e-mail note as soon as possible after the interview. 
• Write a physical thank you note (on nice stationery?) as well, to be sent after you return home. 
• Send to all relevant people (at least your immediate 'host' and head honcho). 
• Add personal details, or reinforce a point that you'd like to make again. 

There was some pushback about whether or not a physical thank you note was necessary or relevant, as opposed to e-mail. I argued that a handwritten note is typically more impactful in that it is a physical object (and a tool that is not usually used, i.e. handwriting, and thank you notes.) I am not sure that the detractors felt that physical thank you notes were worth the effort and expense. 

Perhaps things have changed, and thank you e-mails are now de rigueur. Readers, what say you? 

*Being oblique to protect the innocent

Book review: "The Elements: An Illustrated History of the Periodic Table"

Image credit: Amazon

I was recently sent a review copy of "The Elements: An Illustrated History of the Periodic Table" by UK author Tom Jackson. It's certainly a beautiful book to look at, filled with interesting facts about the history of chemistry (and science in general.) The structure is unique; it is structured as a list of 100 mileposts in history, it starts with "Stone Age Chemistry" as item #1 and ends with "The Higgs Boson" as item #100.* The book teaches a variety of chemically-related concepts (e.g. temperature, disproving vitalism, chirality (!), x-ray crystallography) in very accessible but accurate language.

Since I assume that I am not the target audience of this book, I passed along my review copy to a couple of adolescents (ages 9 to 12) that I know. Two of them were somewhat intimidated by the book, I think ("I would probably read it... if I had to") while one of them paged through it for a few minutes and said, "Pretty neat!" I thought so, too.

I would recommend Tom Jackson's "The Elements: An Illustrated History of the Periodic Table" for adolescents, especially those who are getting into chemistry for the first time. Those young people who already have a love of history will really enjoy this book.

Other than the physical copy of the book, Chemjobber has received no compensation for this review.

*The enterprising purchaser/reader will have to find the latest developments with the Higgs Boson elsewhere, as item #100's blurb begins "In 2011, scientists became hopeful that they could would get an answer to one of the big questions in science: does the Higgs Boson exist?" Short answer: yes, we think so. 

Age discrimination in Silicon Valley

I don't really know very much about age discrimination, but I assume that it does happen. (My short experience observing large pharma layoffs tells me it might, in its weird legal fashion.) The San Jose Mercury News has an interesting article about it, with plenty of quotes about investors and executives ideas that young software developers are more knowledgeable about modern software protocols and have more time on their hands:

Some technology recruiters say unequivocally they see bias at work. Marta Fuentealba, a principal at start-up specialist Talent Farm, says she's encountered it many times. 

She recalls a meeting at a software company a few years ago, when the human-resources executive told her he would like to find somebody "around age 26 or so" to fill a job. An age requirement along those lines would violate both state and federal laws on discrimination, California labor lawyers say. 

"You mean, somebody less jaded?" Fuentealba recalls asking, hoping to jolt the executive back into legal territory. "And he said, 'No, I mean somebody young, probably no older than 26.'" Back at the office, she sent the executive resumes from a variety of candidates. 

..."I am just an incredibly enthusiastic fan of very talented 20-somethings starting companies," Sequoia Capital's Mike Moritz, 58 years old and a top VC, once said at a conference, echoing similar comments he has made over the years. "They have great passion. They don't have distractions like families and children and other things that get in the way of business." He was 49 at the time.

Yikes. Remind me not to try to become a Silicon Valley entrepreneur anytime soon; seems like being a husband and a father could be a liability.

I've never really worked with older chemists as peers for an extended amount of time; I've mostly had them as bosses. I don't really think there's a significant creativity difference between younger and older chemists.*

This bit in the article about certain cosmetic changes during job hunting I found particularly distasteful:

Silicon Valley veterans try to adapt as best they can. Adams of Socialdial ticks off a list of faux pas that he believes peg older jobseekers as outsiders. "You can't have an AOL email," he says. "That's horrible. A Gmail address is okay. What's really cool is an email with your name on it," as part of the domain. 

In person, older job applicants should carry a backpack, not a briefcase, he says. Avoid Blackberries and Dell laptops in favor of Android phones and Apple products. And above all, steer clear of wristwatches, which most younger people have replaced with the clocks on their phones. "The worst would be a gold Rolex," he says. "Tacky, and old."

I wonder if similar (and stupid) age-related cosmetic issues are at work in the chemistry world -- I tend to think not, but I dunno. It seems that we have a culture that values wisdom and experience (relative to Silicon Valley, anyway). But I haven't been in the big world of the pharma/chemical industry very long. Readers, please feel free to correct me.

*I have, on occasion, found older chemists who have failed to keep up with the chemical literature in any serious fashion. (Around the time of Suzuki's Nobel prize, I was amused to talk to one manager who found palladium-catalyzed chemistry to be a cute academic oddity, as opposed to a technology that should be seriously considered.) I don't think that's really age-related, so much as it is about failing to exercise an important prerogative of a Ph.D. chemist's life: to keep current with important, job-relevant literature. I assume that these mental discipline issues are found in both the young and the old.

How many 1st year grad students will get their Ph.D. in chemistry?

A little evening tidbit: Dan Drezner is a professor of international political economy and a longtime foreign policy blogger. He's been involved in an interesting debate about whether or not a Ph.D. is required for going into policy in the Washington, D.C. area. He is pushing back strongly against any encouragement of a doctorate as a terminal degree. Here is a tibdit from his latest long post about it that I found stunning:

Furthermore, not finishing a Ph.D. is not exactly uncommon.  Click on this slide show about Ph.D. attrition rates from the Council of Graduate Schools, and note the following three facts: 

1)  Only 46% of all entrants finish their Ph.D. after seven years in a program.
2)  For social science Ph.D.s, that figure is even lower -- 41%
3)  If you extend it out to ten years, the lowest completion rate among the social sciences is political science -- only 44% complete a doctorate after a decade.  In other words, entering a Ph.D. program and then not finishing is the modal outcome. 

From that report (written in 2008, collected from data before then) the 10-year completion rate was 62% for a doctoral degree in chemistry. (I wonder what that number is now? To SESTAT!)

Job posting: B.S. analytical chemist, Cincinnati, OH

From the inbox:

This hands-on Analytical Technician position will be responsible for performing sample preparation and analytical testing in support of research scientists.
- Hands-on operations of advanced analytical equipment
- Role may include support of testing demand in any lab and may include Microscopy, IR, DSC, chromatography/separations and similar and even lab work in other site labs....

B.S. chemistry desired. 40-60k for Cincinnati? Sounds okay -- readers, what say you?

Daily Pump Trap: 11/29/12 edition

Good morning! Between November 27 and November 28, there were 30 new positions posted on ACS Careers. Of those, 13 (43%) were academically connected and 13 (43%) are from Kelly Scientific Careers.

Yuurrrggghhh: Tiring to wade through all of these academic and Kelly postings.

Denver, CO: Leprino Food is searching for a carbohydrate chemist to be a food scientist; B.S./M.S./Ph.D. desired, with rising levels of experience. (0-2 years for Ph.D.) They're a cheese company (among other items.)

Orange, TX: Invista is searching for an experimental technician (associates/B.S., with 2+ years experience); they have advertised this position at least 5 times this year, which is indicative of either growth or high turnover. Probably the latter. (Glassdoor, for what it's worth, says 50-55k. I am skeptical, but hopeful.)

"Harrisonburg, VA or Menlo Park, CA": SRI International is looking for a director for medicinal or biological chemistry, which they put at associate or full professor level. They want 8-10 years experience, with a requirement of previously getting funding. Huh.

St. Louis, MO: Ameren (a power utility, I believe) is looking for a B.S./M.S. analytical chemist to be a laboratory supervisor. 4+ years experience desired.

Gray absorbent pads

A long list of small, useful things (links):

• Stories of scientists in East Germany, from Sarah Everts. 
• Welcome, "Not the Lab", to the chemblogosphere! This post on utility in federally-funded research has stuck with me. 
• Jess writes about carbon capture technology; I think there's real work here for organic chemists. 
• Which celebrity would you like to be in your lab photo shoot? 
• 10 nitrogens in a row!
• I loved this post on a flame by Th'Gaussling.
• C&EN's Christmas gift guide, including elemental Uncle Goose blocks. (Very sturdy, high quality.)
• Chemical-free food (yikes!)
• A great article on polonium-210 by Deborah Blum
• Milkshake's post on ultrafiltration in polymer chemistry was excellent. 
• Looking forward to answers from Dr. Freddy's AMA.
• John thinks about reshoring, and whether it will happen. I am skeptical, but hopeful. 
• This Dennis Curran commentary in Nature Chemistry (subscription needed) was very pointed, I thought, and only sort of jokey . It came with a fun picture from the journal's hard working staff. 
• Via Liberal Arts Chemistry, this story of a young woman who just wanted her B.Sc. in chemistry is really lovely. 

Did I miss anything? Readers, let me know in the comments. 

A passage that has stuck with me for a while now

This Paul Krugman blogpost on economic insecurity rings really true to me:

Every time you read someone extolling the dynamism of the modern economy, the virtues of risk-taking, declaring that everyone has to expect to have multiple jobs in his or her life and that you can never stop learning, etc,, etc., bear in mind that this is a portrait of an economy with no stability, no guarantees that hard work will provide a consistent living, and a constant possibility of being thrown aside simply because you happen to be in the wrong place at the wrong time.

There are a lot of political responses to this paragraph (Krugman argues for stronger state benefits in his post), but that's not what I am focused on. I do this that it is a remarkably apt counterpoint to Professor Whitesides' call for chemical entrepreneurship, or Madeleine Jacobs' comments about "thriving in the global workforce."

I think that this sentence says something true about industrial chemistry as an enterprise, and what the future might hold. Best wishes to all of us.