Category Archives: Chemistry

Weighty Cogitations on Borohydride

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I have been making a conscious effort to find ways to use borohydride compounds rather than just default to the mighty gray sledge hammer- LAH. There are numerous reports of diverse and wonderful means of activating borohydride to reduce the more refractory functional groups. Recently I prepared and used Zn(BH4)2 on a new substrate. Initially, it appears to work poorly. The grey wall cake seems to contain metallic zinc. If preferences mattered, I’d prefer see electrons reducing my substrate rather than Zn (II) to Zn.

You can’t always get what you want.     M. Jagger

The Cost of Scientific Information. Who Pays and Who Gets Paid?

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For anyone outside of academia who has not actually received an invoice from Chemical Abstracts for literature retrieval services, let me assure you that literature searches will cost you real money.

CAS has weighted the basic search operations and defined them in a menu of task equivalents. When you subscribe, you purchase a bundle of tasks. Tasks can be used like a chit- they can be applied for a variety of search operations. Some search operations are assigned a higher value than others. Obviously, a group of big wheels at CAS sat down in a room and hammered out what they perceive the value of a given operation to be.

At this point, it is useful to remind folks that price is not properly based on cost, it is based on what the customer is willing to pay. CAS has an army of clerks punching abstracts into the database, so they do have some real overhead. While CAS honchos are mindful of paying the overhead, they are also trying to find a pricepoint for their information services. On this I do sympathize with them.

However, where I part ways with this organization relates to the monopolistic arrangement they have with information paid for by citizens of this country. The major pipelines of chemical research information seem to plumb directly into CAS and the ACS.  Research that does not get published by the ACS goes to a variety of private publishing houses. The common thread is the transfer of copyright to the publishing house. By turning over the copyright of publically funded research to these organizations, the public relenquishes the right to free access to results it has paid for.

In a very real way, the published results of our university research complex represents national treasure. What do we do with it? We hand it over to publishing organizations who print it in exchange for the copyright. In this way, we can keep paying for access indefinitely.

In fact, lets highlight some of the features of this transfer of wealth and the cost to society of scientific literature-

  1. Citizens and corporations pay taxes to support the various funding agencies like NSF, NIH, DoE, DoT, DoD, etc., as well as provide private grants.
  2. Funding agencies award grants to institutions and researchers to pay for the conduct of research.
  3. Researchers take a combination of funds and pay for stipends, fellowships, materials, and overhead to support the people who do research.
  4. Research is performed and results are communicated as publications.
  5. Researchers sign over the copyright to their work in exchange for publication.
  6. Publishers such as the ACS, Wiley, Elsevier, etc., then hold a copyright on the content in perpetuity.
  7. For the rest of time, the citizenry who paid for the results have to pay a fee to get a copy of the paper, or travel to the nearest University library and hope that the publication isn’t in deep archival storage and unavailable that day.
  8. Thanks to the Bayh-Dole Act, institutions can patent the results of federally funded work. This means that the hopeful citizens of the USA are barred from the practice of the art they paid for. In fact, they have to work out a license agreement which will include a royalty (with audit trail) and probably a hefty upfront, non-refundable, fee to get the ball rolling.
  9. Despite this royalties cash stream that universities have access to, tuition and fees continue to rise well above inflation.
  10. If you are a chemical scholar out of the cover of academic discounting, you face the full brunt of literature search costs yourself. A monograph or book on any given chemistry topic could easily cost $10,000 in non-academic SciFinder charges (ie., $68 per reaction search). A typical technical book may provide an author $3,000 to $10,000 in royalties over 5 years.

Well, you say, the benefit is to society as a whole. The science we pay for goes into society where, like an incoming tide, lifts all boats.

Nonesense! This tide lifts the good ship Elsevier and the USS Chemical Abstracts. It helps large universities get larger. The generation of information has become a cash cow for a handful of organizations who are subject to precious little scrutiny by those who freely supply the scientific content that keeps the system going.

Graphite Items

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Graphite and other refractory materials can be found at the Graphite Store. A large variety of components, crucibles, tubes, etc., fabricated from SIALON, zirconia, alumina, or graphite, can be found.  Graphite items are surprisingly inexpensive. Great for that dungeon or backyard foundry.

Notes from the A.I. Meyers Symposium

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I was able to attend only the afternoon sessions of the AI Meyers Symposium, sponsored by the Chemistry Department at Colorado State University in Ft. Collins. Peter Beak from the University of Illinois spoke about organolithium chemistry related to CIPE- Complex Induced Prioximity Effect. Along the way, Beak made a few comments about the state of the science of chemistry in America in terms of the lack of a unified voice. He pointed out that the astronomers seem to be quite successful in geting major projects funded because they band together and make a unified case for funding. Beak observed that during difficult times, chemists tend to “circle the wagons and shoot inwards”.

Beak made another point about the perpetually weak state of physical organic chemistry. He suggests that the norbornyl cation controversy between H.C. Brown and Saul Winstein in the 1960’s had a deleterious effect on the field. I have heard this argument elsewhere. I can only assume that Beak means that funding for physical organic research dried up.

Victor Sniekus, Alfred Bader Professor of Chemistry at Queens University, spoke about his work with orthometallation in various projects. Daniel Comins, a Meyers post-doc, talked about alkaloid synthesis.  Much of the work from the Meyers labs was related to directed metallation or pre-coordination of R-Li with a substrate to accomplish some kind of selectivity. It was AIM’s habit to prove the merit of a transformation with an application to some kind of natural product synthesis- usually an alkaloid. I spent a year and a half struggling unsuccessfully with tylophorine and crypotpleurine.

The afternoon was rounded off with talk by Paul Reider, formerly a VP of Process Research at Merck and now teaching at Princeton University. Reider spoke in his typical entertaining manner.  What stands out above the technical details is a statement he made in regard to getting buy in for a process. He was trying to get somebody to try a reaction series-“I said it with such sincerity, they went ahead and did it! ” This is funny because you don’t get the idea that Reider or any of his colleagues are easily swayed by sincerity.

There was a fair turnout of Meyers alumni, post-docs and grad students as well as folks from other groups in the department.

Gaussling’s 9th Epistle to the Bohemians. The Cardinal of Chemistry

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In the fabulous world of industry there are many, many job descriptions held by many, many people. The practical consequence of this is that there are a great number of channels in which the river of your career can flow. Opportunities come and go like eddies in the stream. We advance and sometimes retreat.  Our enthusiasms can reach flood stage or can reduce to a trickle in draught. Our intentions can be muddy or clear.

In the end, though, all rivers run into the sea. Careers can flow narrow and fast or broad and slow. But the unique social status and circle we enjoy in this stream of time is eventually lost into the brackish waters of retirement. 

For academicians and industrialists alike, a PhD buys a seat as a lower level dignitary- a prince. For the academic prince, with hard work and luck, one rises through rank and tenure to become a lord or cardinal living the courtly life of intellectual privilege under the glow of eternal admiration. A prince of academe has but to walk into a classroom to gather the attention and fear of post-pubescent underlings. Through midterms, they hang on your every word. You are golden, and every year brings a new crop of young admirers.

In industry, the fierce hydraulic pressure of what-have-you-done-for-me-lately constantly tips the crown from your head. An industrial prince or princess can be expected to labor in a more diverse variety of capacities. Negotiating raw material prices, feasting with customers, or building a corporate trebuchet. Ominously, an industrial prince may find him/herself in oversight of activities that might one day be filmed by helicopters from a safe distance up wind.

An industrial prince can find himself suddenly in full battle dress swinging an axe from a wounded horse. The Viking warlords of mergers and aquisitions will storm the palace with their corporate siege engines and announce a restructuring of the kingdom. Programs throughout the principality will be halted. Serfs will lay down their scythes in the field and let the barley rot where it stands. Lesser princes will be sacrificed to Odin and upper middle-age cardinals will be sent to the moors in the north to live in sanctuary with the Brothers of Eternal Consternation.

What remains will be a thinner core of chastened cubicle-courtiers huddling behind the organizational battlements. Survivors of the siege. One day the new archbishops and cardinals will arrive in their red silk vestments during the antiphon, bearing their strange implements and unfamiliar liturgy. Thus begins a new age.

Thermite Sparking

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Until recently I was blissfully unaware of the possibility of something called Thermite Sparking. It is a variety of the classic Thermite reaction, only it can happen inadvertently in the workplace by mechanical friction.

Thermite sparking is a circumstance wherein an aluminum part smartly strikes an oxidized iron component generating a momentary and highly localized spot of very hot metal. Normally, the thermite reaction is limited to the small mass of material in the impact zone and does not progress further.

What is useful to know is that aluminum and iron together constitute a sparking pair of materials and could serve as an ignition source for flammable liquids and vapor in the area. An aluminum cart or component could suffer an impact while in motion and provide an ignition source for a fire.

Spandex- Chemistry’s Gift to Mankind.

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A trip to Las Vegas serves to remind one of the very important contribution that chemistry has made to the well being of mankind. I’m not talking about pharmaceuticals or some such pedestrian material. I refer to the marvel of Spandex/Lycra. This form fitting wonder fiber continues to serve our collective betterment. It makes me proud (*sniff*) to be in this field of chemistry where our labors can make such a difference. God Bless this Land, this America!

Mole Day in the USA

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Happy Mole Day greetings from Th’ Gaussling! I’m presently in Las Vegas to serve as Parade Marshal for the Mole Day Extravaganza on Las Vegas Blvd. I’ll be riding in the honorary parade marshals car behind the Radio City Rockettes and the MIT chemistry faculty as we make our way through the ticker tape and the cheering throngs. The parade starts at 6:02 this evening and will progress to the wee hours.

NEP on Dust Explosion Hazards

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Earlier in 2008 OSHA issued directive CPL-00-008, Combustible Dust National Emphasis Program. This program is meant to induce industry to develop a greater awareness of dust explosion hazards via the threat of greater scrutiny by OSHA inspectors.

Dust explosion hazards have been poorly appreciated by plant operators in a wide range of industries. The recent explosion at Imperial Sugar in Port Wentworth, GA, on February 7, 2008, has helped to raise awareness both from regulators and plant operators. Part of the problem has to do with a poor understanding of the explosibility of dusts generally, and with the lack of data on the explosibility of a great many common products in particular. Safety consultants I know have been busy with clients from the sugar refining field. It caught their attention.