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Archive → May, 2011

LyondellBasell Selling French Refinery

Lyondell has hired an investment banker to help it sell its refinery in Berre, France. Lyondell bought the refinery in 2008 from Shell for $700 million. The 105,000 bpd refinery “has not fulfilled economic projections made at the time of the acquisition,” the company says.

It isn’t like they gave it a lot of time to work. OK, who am I kidding? Lyondell’s refining segment, which also includes its 292,000 BPD refinery in Houston, lost $2.4 billion in 2008, and $360 million in 2009. It managed to pull in a $242 million profit in 2010 on $15 billion in sales. All of Lyondell’s business have greater operating profit margins than refining.

Lyondell is keeping the ethylene cracker, polyethylene, and polypropylene plants on the site. It so happens that I visited Berre in the late 1990s. A plant manager or someone—I’m not totally sure because he spoke only French—gave me a personal tour. We stood on a high promontory, he struck Napoleonic poses with his hand on his tummy and kept on saying “voilà.”

Anyhow, Elenac—the BASF/Shell polyethylene joint venture that is now a part of Lyondell–was constructing a plant at the site when I was there. I think there was something happening to a Montell polypropylene plant while I was there as well. My point is that the polyolefins plants are probably in good shape because they are relatively new.

I do wonder what Lyondell will do with the Houston refinery. It has been a part of Lyondell since the company was spun off of Atlantic Richfield in 1985. For most of those years, it was a joint venture with Venezuelan state oil company PDVSA and made gasoline for Citgo stations. Lyondell bought out PDVSA’s share of the JV in 2006.

The refinery gets crude under contact from PDVSA. Obviously, that isn’t a great position to be in. It got less than half of its supply from PDVSA in 2010. I recall it received much more of its feedstock from PDVSA a decade ago. Interestingly, that contract is up in July. I’m curious to see what happens.

Guest Post: Could New Tricks Turn Iron into a MedChem Champion?

Is iron on the brink of med chem stardom? SeeArrOh guest posts about the chemistry that makes it possible. SeeArrOh is a Ph.D. chemist working in industry.

Medicinal chemists know the drill: more molecules, faster please, and cheaper, if possible. A large portion of this effort goes towards making carbon “building blocks” with the correct atomic handles to link carbon atoms together, so called cross-couplings, which build the skeletons of most drugs.

“Ready for my close-up!" (photo credit: nuttakit)

Chemists have long dreamed that these well-known C-C cross couplings catalyzed by expensive precious metals could be performed by base metals such as copper or nickel.  Enter our old friend iron, that pennies-on-the-dollar redox champion and enzymatic superstar. Unfortunately, its strengths are also its weak points – paramagnetic behavior that distorts NMR signals, a tendency to oxidize readily, and ability to do 1-electron chemistry as easily as two, as opposed to the well-established 2-electron pathways for metals such as Pd, Pt, and Rh.

So, iron still has a long way to go before it’s adopted by chemists as a workhorse metal, but two new examples show that it may yet be tamed.

For iron’s first act, we go to Oregon State University. The Arp and Karplus groups (Science 2011, 332, 929) had recently collaborated to solve a crystal structure of a “highly symmetric” protein, which they dubbed symerythrin (get it?). Upon closer scrutiny, the structure contained something odd: a C-C crosslink between two otherwise unfunctionalized amino acids . . . and one side of the new bond is a methyl group, a traditionally tough substrate for this kind of reaction. Once the protein begins to organize its 3D architecture, the group hypothesizes that its di-iron core works its magic: in the presence of O2, a high-valent Fe(IV)-Fe(IV) species capable of abstracting a lone hydrogen from a valine (Val) residue is formed. The new alkyl radical reaches across the peptide chain to add to a nearby phenylalanine (Phe), and a reductant completes the cycle. The authors point out that protein cross-linking is not uncommon between sulfur, nitrogen, and oxygen-containing amino acids, but this is the first example between carbon residues. Hopefully, some new ideas about iron-catalyzed C-H activation or new ways to assemble druglike cyclic peptoids might spring out of this research.

For the encore, we travel across the country to Princeton University. Paul Chirik has recently disclosed (J. Am. Chem. Soc. ASAP DOI: 10.1021/ja202992p) a [2+2] cycloaddition catalyzed by an iron complex. The interesting twist here is that, despite the natural tendencies for dienes and olefins to form [4+2] adducts – see the disclosed Diels-Alderase from early 2011 – this reaction shows no products resulting from that pathway.  To explain the difference, Chirik provides the pièce de résistance: the crystal structure of a stable alkyliron complex that catches the two reactants in a C-C bonding “snapshot.”  Chirik admits that the reaction is fairly limited right now, since it only turns over one substrate (butadiene), but his mechanistic studies might lead to optimized catalysts for performing on-demand cyclobutane formation on more complex alkenes. Given the liberal use of cyclobutanes in medicinal leads, it’s only a matter of time before iron claims the limelight.

*Update: The Science article from ‘Act 1’ is rounding the blogosphere, having just appeared at The Curious Wavefunction and C&E News. ‘Act 2’ has garnered some attention over at Naturalproductman’s Blog.

Smart as a Whip; Dumb as a Post

Human beings are both amazingly clever and staggeringly stupid.

No other conclusion is possible given two stories on opposite pages of the May 26 Washington Post.

The story on page 2 of that day’s paper carried the headline: “Groups sue FDA to try to limit antibiotics in animal feed.” The story on page 3 had the headline: “New NASA mission will ‘kiss’ asteroid in 2020.”

Let’s do clever first. On May 25, NASA announced that it would launch a spacecraft to an asteroid in 2016 and use a robotic arm to obtain samples from the asteroid and return them to Earth in 2023. The mission is called OSIRIS-REx.

According to NASA’s website, OSIRIS-REx will travel through space for four years and approach the “primitive, near-Earth asteroid designated 1999 RQ36. Once within three miles of the asteroid, the spacecraft will begin six months of comprehensive surface mapping. The science team then will pick a location from where the spacecraft’s arm will take a sample. The spacecraft gradually will move closer to the site, and the arm will extend to collect more than two ounces of material for return to Earth in 2023. The mission, excluding the launch vehicle, is expected to cost approximately $800 million.”

That pricey space dust will be stored in a capsule that will land at Utah’s Test & Training Range in 2023. 1999 RQ36 is interesting for a couple of reasons, according to NASA. Asteroids are relics of the solar nebula from which the sun and planets formed. Their composition can tell us something about our origins. There’s also a one in 1,800 chance that 1999 RQ36 will clobber Earth in 2182. OSIRIS-REx probably can’t do anything about that.

But think of it: Humans can build a machine and launch it into space, guide it hundreds of millions of miles to rendezvous with a speck of an object, grab a little piece of that object, and return it to a precise location on Earth eight years later. That really takes brains.

It also takes brains to invent a whole range of molecular entities that we can ingest to kill many pathological bacteria without doing any damage to ourselves. They’re called antibiotics and, over the past 80 years, they’ve changed human existence.

Of course, the brilliant creatures who can build OSIRIS-REx and invent antibiotics would never do anything so stupid as to jeopardize the efficacy of those almost magical chemicals, would they?

Of course they would, if there were enough money to be made doing it. Between 70 and 80% of all the antibiotics used in the U.S. are given to healthy farm animals to promote faster growth and keep them healthy. Not to treat disease, mind you. To allow them to use food more efficiently and to prevent disease in the factory farms where most farm animals are raised in the U.S. today.

This, of course, is a prescription for promoting the development of antibiotic resistance. It’s exactly why you don’t dispense antibiotics willy nilly. It’s exactly why your doctor tells you to take every last one of the prescribed antibiotics even if you feel all better days before the bottle is empty.

Use of antibiotics useful to humans to promote farm animal growth was banned in the European Union in 1998; the use of all antibiotics for such purposes was banned in the EU in 2006. The FDA, in its inimitable fashion, has tiptoed around the issue, issuing a draft guidance last year urging “judicious use” of antibiotics in farm animals. Antibiotic manufacturers and U.S. farmers maintain that there’s not enough evidence to warrant a ban.

Look, this is a no-brainer. Antibiotic resistance among bacteria that threaten humans is rampant. There are a lot of reasons for that, all of them dumb. Using antibiotics to grow fatter hogs, cattle, and chickens is about the dumbest. There’s a bill in Congress (H.R. 1549) introduced by Rep. Louise Slaughter (D-N.Y.) that would ban nontherapeutic use of medically important antibiotics in farm animals. It ought to pass.

Thanks for reading.

When Picasso Went Industrial

Scientists are studying Picasso paintings to figure out if he used industrial paint. © Sarah Everts

Last week curators, conservators, and museum scientists congregated in Marseille, France, to discuss a quirky fad among painters such as Pablo Picasso, Joan Miró and Wassily Kandinsky. During the first half of the 20th century, these artists began using newly invented industrial paint called Ripolin, intended for walls, instead of traditional oil paints.

One major motivation was time: Industrial wall paint dries in a matter of hours, while oil paint can take months. Like the rest of us, these artists had moments of procrastination. Being able to produce work just days before the opening of a new exhibit was certainly a perk, says Francesca Casadio, an organizer of the conference From Can To Canvas, and the director of conservation science at the Art Institute of Chicago.

Artists had other motivations for using Ripolin, such as shocking the stodgy traditional art world by using an industrial product, Casadio says. Some motivations were probably purely aesthetic: Industrial paint was glossier than matte oil paint. And in addition, artists could achieve unusual textures on artwork surfaces with the quick drying paint.
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Diagnosing The Devil Inside

Using the new non-invasive technology on a plastic statue (left), the researchers were able to show that it is composed of nylon (blue) and cellulose acetate (red). Credit: Anal. Chem.

Similar to a disease, chemical degradation often advances quietly in art and artifacts, without any external warning signals. That is, until a breaking point occurs, and museum staff are suddenly faced with a faded painting or a cracked sculpture.

Like doctors who want to diagnose patients at the early stages of their illness, when treatments are more likely to work, museum conservators also want to assess the health of cultural artifacts at the initial stages of degradation, and they want to do so non-invasively–that is, without taking a blood sample.

Now Matija Strlic at UCL has just published an article about a new diagnostic tool that can visualize the internal degradation of artifacts before the damage is apparent to the naked eye.

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But In the Meantime, More CO2

While the  U.S. reviews its nuclear energy policy, countries that turn away from nuclear will have to deal with an uptick in CO2 emissions.

Japanese  Prime Minister Naoto Kan said earlier this month that the country will promote renewable energy rather than bring more nuclear reactors online. And Germany has placed a moratorium on nuclear power generation. Today’s Wall Street Journal has a useful summary of an International Energy Agency report that has quantified the increase in CO2 emissions that will result in Germany.

The story explains that “the shutdown of Germany’s nuclear plants will take out about 50 terawatt hours of low-carbon electricity a year” and says that the country will likely replace it with fossil fuel-derived power that will produce 25 million metric tons a year of CO2 emissions. Germany is subject to the EU’s emissions trading scheme, so it will have to offset those emissions. One way to do so, says the report, is for the country to substitute electricity from natural gas plants for those that use coal (or trade for permits with another country that does so).

But it’ll take a lot of swapping, the Journal finds. “An extra 90 terawatt hours of gas-fired power would be needed, replacing 40 terawatt hours of power from coal plants to offset the entire 25 million tons of CO2.”

Of course countries that want to replace nuclear power – either a little or a lot – will be looking to renewables. It’s not clear yet whether – and how much – governments will spend on incentives to increase the renewables infrastructure if nuclear is less a part of the portfolio. In January, for example, Germany started to cut back on feed-in tariffs for solar power.

Translating Documents Online, An Experiment

One thing that I do fairly often is translate documents on the internet. I normally use Babelfish and usually I am translating Spanish and Portuguese. I do have enough of a working knowledge of both languages that I can muddle through press releases without help. But it saves time and prevents possible human error if I have the translator do most of the heavy lifting and then zero in on the important parts with my own analysis.

I did recently translate some documents in Dutch and German in Google and noticed that they were better than some human translations I have seen in those languages. (Dutch and German do seem more straight forward than Romance languages.)

Anyway, I decided to do a side by side comparison. I am using a Braskem press release issued earlier this week on an accident at one of its plants. I figured I would share the result because businesspeople, scientists, and curious people of all kinds are using translation services more and more.

Braskem’s original Portuguese:

Em continuidade aos comunicados divulgados anteriormente, a Braskem esclarece que sua unidade de Cloro Soda de Alagoas permanece inativa por decisão da companhia e nenhum outro vazamento foi detectado desde o primeiro evento.

A Braskem prossegue com o trabalho de identificação das causas dos eventos e está colaborando com as autoridades e órgãos competentes no esclarecimento dos fatos.

Cinco trabalhadores da Mills, atingidos no início da manhã de hoje pelo rompimento de uma tubulação quando preparavam uma inspeção para identificação das causas do primeiro evento, receberam atendimento médico no Hospital Geral do Estado. Um deles foi liberado ainda pela manhã e os demais continuam sob cuidados médicos.

Here’s Braskem’s translation:

Complementing the notices to the market published previously, Braskem clarifies that its Chlor-Alkali in Alagoas will remain inactive by decision of the company and that no other leak has been detected since the initial event.

Braskem continues to work to identify the causes of the event and is collaborating with the applicable authorities and agencies to clarify the events.

Five workers from Mills, who were injured early this morning by the rupturing of a pipe as they were conducting an inspection to identify the causes of the initial event, received medical care at the State General Hospital. One of the workers was released this morning and the other workers remain under the care of physicians.


In continuity to the divulged official notices previously, the Braskem clarifies that its unit of Chlorine Soda water of Alagoas remains inactive for decision of the company and none another emptying was detected since the first event.

The Braskem continues with the work of identification of the causes of the events and is collaborating with the authorities and competent agencies in the clarification of the facts.

Five workers of the Mills, reached at the beginning from the morning of today for the disruption of a tubing when they prepared an inspection for identification of the causes of the first event, had received medical attendance in the General Hospital of the State. One of them was set free still per the morning and excessively they continue under medical cares.


Continuing those reported previously disclosed, Braskem explains that his unit Soda Chlorine Alagoas remains idle for the company’s decision and no further leakage was detected from the first event.

Braskem continues the work of identifying the causes of events and is collaborating with the authorities and competent bodies in clarifying the facts.

Five employees of the Mills, reached earlier this morning by the rupture of a pipe when preparing an inspection to identify the causes of the first event, received medical care in the General State Hospital. One was released later in the morning and the others remain under medical care.

I would say that Braskem’s translation wins hands down.

Babelfish and Google both make a mess of the first paragraph. I would give the nod to Babelfish because the Google version of the first phrase is completely bewildering.

I give Google a slight edge with the second paragraph. “The Braskem” sounds too much like “The Batman”. I am, however, not crazy about “competent bodies”. It works in this case, but I wonder if other senses of the word “órgãos” can be conflated. “Agencies” captures the meaning better.

Both translators confuse matters in the third paragraph. They begin by giving the impression the workers were “reached” or rescued, not “injured”, which is sort of the opposite. Google, however, makes sense towards the end of the paragraph. Babelfish makes it seem like the workers medical care was “excessive” for some reason.

Delaware’s Day For Richard Heck

Heck (right) and Theopold during the Q&A. Drahl/C&EN

These days, it’s hard to pull Richard Heck away from his orchids, from his life in a rented bungalow in the Philippines. But when you’re a Nobel Laureate, folks tend to want to meet you, to glean some wisdom from your experiences, and to shower you with still more honors.
And so it was that Heck, who shared the 2010 Nobel Prize in Chemistry for his work in organometallic chemistry, came back to the States with his wife Socorro to attend a symposium held in his honor. Over five hundred chemists from 20 states and from countries as far away as Japan packed a conference center at the event, held at the University of Delaware, Heck’s academic home from 1971 to 1989. Luminaries in catalysis, including Heck’s fellow laureate, Purdue University’s Ei-ichi Negishi, gave presentations. Via a letter, Delaware’s governor Jack Markell declared May 26, 2011 Richard Heck Day. The day truly belonged to Heck, a self-described introvert who at times seemed humbled by all the fuss.

From what little I’d interacted with Heck, this came as no surprise. In May of last year I interviewed him for a story on named reactions, where his namesake chemistry, the Heck reaction (or Mizoroki-Heck reaction, depending on who you ask) was prominently featured. He was funny and self-deprecating in our brief interview, and he seemed settled enough in that flat in Quezon City that I figured I’d never meet him in person, even after his Nobel Prize was announced. When Delaware chemist Joseph Fox told me about the Heck symposium, I jumped at the chance to attend. Continue reading →