Category Archives: Chemical Industry

Thoughts on Organizations

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The management of process development in the chemical indstry is a highly specialized activity requiring skills and experience that crosses many disciplines. Many people doing such work today are practicing in a corporate environment where management structure and support services are already in place. Organization managers have a portfolio of standard operating procedures (SOP’s) and daily operation is a relatively straightforward matter of keeping the ball rolling. Individual work product contributes to a large project where many people and large streams of cash are choreographed to arrive at a well defined goal. Degrees of freedom are frozen out and the dominoes are carefully prealigned to topple to a particular spot.

Process Development Warning: Eventually you may have to shoot the chemist and get on with the project.

(Alright, it’s a joke)

In smaller organizations where individuals have greater personal influence, where money is less certain, and where fewer operational resources may be available, the end state of a technology-push project may be less certain. Choices relating to the details and specification of a product can be changed with greater ease than may be possible in a larger organization with many layers of management.  This is both a benefit and a curse for the small business.

An organization that is not yet ossified with excessive management is one that may have the structural ability to adapt to the business environment with greater ease than one that is “over managed”.  But this is conditional. A small business responding to market pull may have better survivability if it is flexible. A technology push organization that seeks to bring a new product or service to market may actually suffer from too much organizational flexibility.

Smaller organizations have to invent and implement management structure that constrains the dominoes to topple to a defined endpoint. This can be quite difficult for Explorer-Discoverer types to set into action. The key thing for technical people to consider when starting an organization is that placing an organizational person in the founding member group is critical to building management structure from the outset.

Aldrichimica Acta, Vol. 42, No. 2, 2008.

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The latest Aldrichimica Acta is out- No. 2 of volume 41. This publication was started by a friend, teaching colleague, mentor, and former boss who spent some of his best years working for Alfred Bader. He eventually retired as a VP of something or other at Aldrich. A truly great guy. For a while, the task of catalog publishing was his job. He bought paper by the rail car. Their job was to increase the size of the collection by 15 % per year.

He also invented the coffee pot kugelrohr system that Aldrich sold for a long time. It has now morphed out of recognition. But he showed me the prototype motor assembly. It consisted of a reciprocating air motor built for automotive windshield wipers wired onto some pegboard. The air motor used either air pressure or vacuum and had a metal tube that connected the vac line from one side of the motor axially to the other.  The reciprocating motor got around the need for a sealed vacuum bearing. To one side of the reciprocating tube was connected a vacuum line via flexible rubber hose, and to the other via hose and barbed connector, a series of bulb tubes and pot. 

The coffee pot came from a West Bend coffee pot plant down the road in Milwaukee. Aldrich bought the reject pots and paid a guy to refit them for kugelrohr duty in his garage. It was a very successful product. When I went to grad school we had a Buchi kugelrohr for bulb-to-bulb short path distillation. But I still remember with some fondness having to sit at the bench twiddling the Aldrich kugelrohr by hand while feeding dry ice onto the receiver. Sometimes we would drip dichloromethane in the receiver and let the evaporative cooling do the trick. We’d use the air motor for lengthy distillations.

On wrecking your career

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It’s the end of a rotten day and I’m fuming. There are many ways to see harm to or the obliteration of your career in the fabulous world of industry. It can be self-immolation or you can catch a bullet just by standing there. Sometimes you can be removed for reasons that are never clear- your division or your job description can be rendered obsolete by the geniuses driving the boat. Industry demands loyalty and the ability to absorb abuse through many forms of institutionalized intimidation.

Sometimes working in industry just sucks. There is no way around it nor is there a better description. The trick to weathering bad times is to find a way to reign in your temper when things get stupid. Speaking for myself- a large irritable mammal- this can be really hard to do. I am a smartass with a good vocabulary and a decent imagination- a detonable configuration and am unable to keep my mouth shut sometimes.

I had to learn this temper thing the hard way. I once beared my teeth and snapped back at a senior staff member who was behaving just horribly. He had a need for dominance and used his lengthy time in service to leverage it. Skipping to the conclusion, I ended up leaving and he stayed.  Moral of the story- for long term survival, find a way to let bad characters implode through their own weaknesses.  If you want to stay, then resolve to stay.

In industry it is quite important that your “deliverables” are not just visible, but also mission critical. Industry is cyclical and companies inevitably expand the head count. When times get tough, the head count is one of the first things they want to trim. While times are good, try to remain on important projects that are highly visible and valuable to management. Try to avoid being put on invisible projects.

Be judicious in how you use email. Don’t give others a stick that they can beat you over the head with. Never compose an email while you are angry. Always be fair and generous, especially to despicable characters. Even handedness in the face of conflict will always win friends and allies. Try to avoid blind copying and excessive cc’s to upper level people. Try to settle your disputes without making a comedy show of it in front of management.

You will eventually find that one of the major problems in life is the matter of control. Many kinds of conflict and ordeals derive from the need for control. Some people harbor pernicious control issues that disrupt everything around them. They are like typhoid carriers. I have yet to find a rule of thumb for such a situation. But the thing to remember is that such people could cause you to behave badly as well.  , so a person has to be on guard when certain people are around. This sounds simple, but it can be quite hard to do. I am writing this very post as a way to process my own frustrations.

A Few Thoughts on Organizations and Systems

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Being over the hump and into the 2nd half of my chemistry career, I find that more and more of my time is spent dealing with systems issues. Not fighting existing systems. Synthesizing new ones. One of the things I have come to appreciate is the value and necessity of at least some level of bureaucratic structure as an organization grows. Really, it has been an awakening.

My current project involves receiving and organizing a massive stream of diverse information. It is a taxonomic nightmare. How does one organize critical and confidential information in such a manner that it can be accessed for future reference? It is more than a matter of profligate use of file folders. I have drawers and drawers of file folders with commercial and scientific information in them, but I have lost track of what I already have. What has to shake out of my current task is a bureaucratic mechanism.

I have come to be viewed as a “resource”. This is a euphamism for “keeper of obscure information”, or more to the point, “he who knows where the bodies are buried”.

Getting back to the matter of systems generation, a problem organizations may develop is one in which valuable, painful, and expensive lessons get lost over a relatively short interval. People naturally like to get on with things. Problems in the past are just that- in the past. We overcame a challenge and now we are on to bigger things. But what folks underestimate is that past problems are often the result of habits of thought and poor adaptation to change.

It is easy to get bewildered in a conceptual space where there are no sharp edges or crisp boundaries. In the chemical business world, you find that the crowd naturally divides into science/technical people and business people. There are always a few cross-over people (freaks like myself) who defy tidy categorization.  But for the most part, when the tray stops shaking, the people settle into particular positions.

Business-types like to deal in the binary world of yes and no. Science-types accept that this is possible only from a great distance from the problem.  Business-types use the tool and toss it when done. Science-types can become enchanted with the tool and will try to make it better.

One of the tricks to system development in an organization is to define what constitutes a normal condition. Once this is defined, an off-normal condition can be recognized and SOP’s can be written to deal with it. As a psycholgical precaution, this is where you begin to get insights into the deep-seated insecurities of your colleages. Many long-time acquaintances can reveal control-freak behaviour or authority issues.  The generation and implementation of systems in an organization always involves greater control and loss of degrees of freedom for individuals. People will see this coming and things may get contentious.

As more people become involved in any endeavor, complexity inevitably arises as failure modes are uncovered and people learn to game the system. Good leadership can go a long way towards helping people keep perspective as things become more complex.

InBev Chugs St Louis Utility Beer Maker

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It is surely a sign of the End Times. Just as sure as the Four Horsemen of the Apocalypse and cats sleeping with dogs. A Belgian company buys Anheuser-Busch.  Wow.  Just the thought of it is too much for me to get my arms around. Michelob now has a kissin’ cousin named Stella Artois. 

What was that old brain teaser an Austrian colleague once asked-

Can you name 10 famous Belgians? 

I agree. It is a bit outrageous. I’m sure there are as many as 20 famous Belgians.

Who knows? This may be the European connection NASCAR has been looking for.  Watery beer, fast cars, and drunken hooligans. It’s universal.

Nuclear Chemistry Article in Daily Kos

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For those of use who carry around an interest in nuclear science, there is a short but interesting article in the Daily Kos written by a chemist on the topic of the Hanford site in Washington.  Of particular interest is the link describing a radiological assay of a chemist who died at age 76 of cardiovascular disease.  At the time of death they found 540 kBq of activity in his body- 90 % in his skeleton. The gentleman had been involved in a glovebox explosion involving exposure to 241-Am at age 64.

What do you do with a radioactive corpse? One option is to donate your body to science. The WSU College of Pharmacy maintains a registry of data culled from uranium and plutonium workers. A recent description of donated bodies is found in this pdf. One donation is from a plutonium worker who was present in the 1965 fire at Rocky Flats. He retained an estimated 6.8 kBq of lung burden. They did not specify how this was determined.  Rocky Flats did have state of the art whole-body monitoring and a substantial health physics department.

Pu detection is a little tricky because one of the important markers for Pu contamination is 241-Am, an alpha and gamma emitter (Pu is a bad actor mostly because of internal alpha exposure).  Residual and highly active 241-Pu (104 Ci/g) beta decays to the highly active 241-Am.  Unfortunately, not all Pu isotopes decay into Americium. This Am isotope allows for gamma ray spectra to be gathered so an estimate of Pu exposure can be calculated. The ever popular 239-Pu isotope alpha decays to 235-U without much gamma emission. So, the calculation of Pu exposure and dose depends on knowing the purity of the Pu at issue.

A critique on scale-up suitability

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In my quest to stimulate bench chemists to think like industrialists, I like to bring examples of chemistry from the literature to highlight a point I’m trying to make. The literature is full of transformations and research that serve as positive and negative examples of good scale-up thinking.

There are examples, however, that are less than choice in terms of green processing or good scale-up thinking. As I have said previously, green chemistry and good scale-up principles may not be equivalent concepts, but they can and often do run in parallel.

An interesting transformation is featured in the recent article entitled Efficient 1,2-Addition of Aryl and Alkenylboronic Acids to Aldehydes Catalyzed by the Palladium/Thioether-Imidazolinium Chloride System, by Kuriyama, Shimazawa, and Shirai, J. Org. Chem., 2008, 73, 1597-1600. [My apologies to the authors for their unanticipated role in this analysis.]

In this article a bond forming reaction between 1.5 eq of a boronic acid and 1.0 eq of an aldehyde is described affording a secondary alcohol. The transformation is catalyzed by 0.5 % Palladium allyl chloride dimer with 1 % of a custom imidazole carbene precursor in the presence of 2 eq CsF as base. The reaction mixture is heated to 80 C in dioxane and the chemistry is reported to be over in ca 20 minutes.

I am somewhat reluctant to be critical of chemistry that is done catalytically and is high yielding. But this transformation, solid science though it may be, would be difficult to justify taking to scale-up without an examination of alternative schemes.  Let me explain my thinking.

First, on the basis of atom efficiency alone, this process requires that a lot of different elements find their way into the pot. The tally is C, H, N, O, Cl, B, Pd, Cs, F, and S to just make a C-C bond to produce a benzyl alcohol. A scale-up chemist would have to ask, why not use a Grignard and the aldehyde? Granted, there may be incompatible functional groups on either Ar1 or Ar2 that would not tolerate a Grignard reagent. However, it is worth pointing out that the conventional way of making boronic acids is by addition of a boronic ester or fluoride to RMgX or RLi followed by hydrolysis. Compatibility is an issue there as well.

One might object that many of the diverse atoms used in the reaction are at a catalytic level and as such may not constitute a major cost or environmental insult. True enough for the user of the process. But the metal complex must be manufactured somewhere at a larger scale for distribution. Pd mining and beneficiation requires energy inputs and generates wastes. The same idea applies to the imidazolinium salt.

The reaction does seem to require 1.5 equivalents of boronic acid and 2 equivalents of cesium fluoride. Boronic acids are specialty synthetic intermediates whose manufacture generates its own waste stream. Furthermore, boronic acids can be on the expensive side. The use of a boronic acid as a latent nucleophile for a straightforward addition to an aldehyde seems somewhat extravagant.

Cesium fluoride residues (2 equivalents) will find their way into the aqueous waste stream and possibly to an incinerator where the solids may end up in roadway pavement or a landfill. While fluoride is an efficient base in this case, common sense suggests that carbonate may have a more benign fate in the environment owing to the fact that it decomposes to water and CO2. Unfortunately, the best yields are with cesium as cation.

Chemists seeking to apply this kind of coupling chemistry would be well advised to be extra careful in their IP diligence. The use of metal catalyzed coupling reactions may already be patented or applications may be pending for patents. The same comment applies to the use of imidazolinium carbenes. Industrial chemists would be well advised to look deeply into the carbene species for process and composition of matter claims. Ever since the Bayh-Dole Act, university patents have been popping up like dandelions.

I do not want to be too critical of this chemistry. It is an interesting transformation and certainly may be of use for some kind of product. But for scale-up, at first pass it seems too far from earth, air, fire, and water. I would say that for maximum profit, this process is more of a Plan B or Plan C scheme.

From NIMBY to BANANA

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The 2005 government report entitled Peaking of World Oil Production: Impacts, Mitigation and Risk Management, by Hirsch, Bezdek, and Wendling, is a sobering tally of the current picture of oil production and consumption in the world today. Often referred to as the Hirsch Report, the authors take a “now shot” of the global oil production scene and speak directly to the matter of mitigating the approaching economic disruption that must usher an unprepared nation into a future of peak and declining oil production.

If you read the Hirsch Report and pay attention to current events, you may be gripped by a kind of cognitve dissonance, or a haunting sense resembling a schizophrenic episode of contradictory voices in the collective consciousness.  While the global warming showboat is paddling up and down the Mississippi blowing steam and calliope music, nationalized oil producers are failing to answer calls for increased production in reply to a dramatic ramp-up in petroleum demand. Some call for increased exploration and others call for drop in replacements for petroleum. All the while, evidence accumulates that the ecosystem suffering from consumption and waste generation.

As with any discussion involving economics, it is possible for people to speak imprecisely when discussing supply and demand. Econobrowser takes Hirsch to task in this manner. It seems that many of us confuse demand with desire.

Supply equals demand today, supply will equal demand in 2025, and supply will equal demand in 2050. Whatever Hirsch means by “peaking of world conventional oil production,” it certainly isn’t the condition that “production will no longer satisfy demand.”

Our news media, now almost fully morphed into a perverse mix of gibbering Bill O’Reilly clones and entertainment news programming, prattles endlessly about the hurtful gasoline prices and truncated vacation plans. Government makes flatulent noises about more drilling, but hardly a peep about reduced consumption.  Where is the journalist corps? Who is asking the tough questions?

In isolation, either climate change or an exponential oil shock are more complex than nimrods leaders in the Bush administration can process. Together, these stresses add up to a major challenge to the way we live.  Maybe the situation is more complex than any nation can reasonably respond to. With global prosperity comes global demand for resources.  Western nations have built a house of cards based on cheap petroleum. Instead of wage growth in the past 20 years, we have been given easier access to credit. Instead of increased savings, we have found ways to burn up discretionary income.

A major part of what has to happen to adapt to the new reality of petroleum scarcity is a remodel of our infrastructure. We need more passenger rail lines and terminals with the necessary right-of-way issues taken care of. Workers need to live closer to their place of employment. The airlines have to figure out how to operate profitably with reduced passenger miles. We must upgrade our electric power distribution system to accommodate the increasing reliance on electrical energy. If wages do not change, we must adapt to having less discretionary income to spend. 

But a remodel of infrastructure will require that we adapt to living nearer to it. In the past, a proposal to build a power plant is met with a chorus of outrage or “concern”. It used to be called NIMBY- Not-In-My-Back-Yard.  The latest acronym is BANANA- Build-Absolutely-Nothing-Anywhere-Near-Anything. New power transmission lines and generating plants will have to go up and it will have to happen somewhere. People naturally fret about real estate prices and their view from the dining room window. I foresee more exercise of eminent domain in the future.

1950’s Chemistry

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I recently spent some time listening to an acquaintance talk about his days as a student at MIT and as a grad student at Harvard in the early 1950’s.  He had Geoff Wilkinson for inorganic chemistry at MIT as an undergrad and later did his PhD with Wilkinson at Harvard.  Curiously, Wilkinson did radiochemistry in the Manhattan Project prior to joining academia. His radiochemistry experience compelled him to work fast and in test tubes, according to my friend.

My friend’s lab mate in Wilkinson’s group was Al Cotton. They started grad school together ca 1952 or so. This was shortly after the sandwich structure of ferrocene was proposed by Wilkinson’s fellow Harvard prof R. B. Woodward. Woodwards basis for this structure was on symmetry and a single IR stretch absorption. Spectroscopically, the original sigma bonding model didn’t fit the data.  Just prior to this, Wilkinson had begun work on a variety of organometallic Cp compounds. As the story goes, when Woodward expressed interest in making more Cp compounds, Wilkinson went to his office and “had words” with Woodward. Afterwards, Woodward moved on to other things.

My friend laughingly recalls the time he was chewed out by his P-Chem prof, the great George Kistiakowski and earlier, by Arthur Cope at MIT. He recalls being summoned to Cope’s office. Cope was wearing pink slacks which contrasted with his red hair. He was displeased about the impertinent back channel invitation my friend pitched to Linus Pauling to speak to the chemistry club. (I haven’t verified the color of Cope’s hair)

My friend recalls having E. J. Corey as a lab assistant while in an undergraduate lab at MIT. He joked that he saw Corey once at the beginning of the term and once at the end. My PhD advisor, Al Meyers, did his post doc with Corey some years later. Small world.