Category Archives: Chemistry

Lawyers and Plain Talk

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I am one of the odd characters who rather admires lawyers.  I have had a few occasions to be on both sides of a lawyers gun barrel and have come to admire them as a group for what they do.  Contrary to what most people believe, they do much more than simply provide exquisite obfuscation. Yes, they can generate plenty of fear, doubt, and anger. Divorce lawyers generally have a stable of enemies. But more to the point they are trained to drill down to the facts of the case.  They can pierce through the knotted fur ball of imperfect memory and slanted testamony to find the thread that connects the facts.  Well, at least some of them can.

But what is perhaps more interesting than how lawyers perform is how their clients behave around them.  If two parties are trying to plow through a complex negotiation without lawyers, for instance, it is likely that the tone of the proceedings will differ from a meeting with lawyers present.  It is practically axiomatic that once one side has their attorney present, the other side feels compelled to have theirs present as well.  This only makes sense.  If the meeting concerns contractual issues or matters of liability or indemnity, it is best to have some legal firepower to oversee agreements or disclosures. 

What happens when the attorneys are present is this. Like a startled bivalve, each side clamps down their shell and communication becomes a thin gruel of vague and hesitant exchanges.  Suddenly everthing takes twice as long because both sides have to hunker down with counsel to discuss the plan off-line.  Everyone is afraid of a slip up. Representatives of each company not only fear the other sides attorney, but their own as well.  They fear the other sides attorney for advantages they might seize, but fear their own attorney for the consequences of a blunder on their side.  Your own attorney will be able to describe your blunder in living color to management in the postmortem, so everyone is super cautious. 

What is often missing in negotiations involving lawyers is plain talk.  It often happens that in trying to be careful with disclosures and declarative statements, both sides fail to actually make a clear statement of what they want.  Consequently, each side ends up negotiating a slightly different problem.  It can take multiple meetings before everyone is on the same page negotiating the same deal. 

Sales people are configured by nature to bring home the deal.  They are inclined to do and say what it takes to git’er done. Procurement people are coy by nature and acclimated to their companies policy on purchasing. They want the best price, terms, and delivery possible.  They will want concessions from the vendor and firm agreements on inventory and pricing schedules.  They want and want and want. But in the end they have to get.  They have to make the deal because raw materials have to arrive before invoices can go out for finished goods.

In negotiation, both sides bring their magic to the table.  When lawyers are present, in my experience at least, everyone becomes so bloody careful and hesitant that a spirit of distrust can form. People become reticent to engage in plain talk. Lawyers are concerned with the “what if’s” and in fact it is their duty to make their client aware of such things. Soon after the lawyers jump in, people begin behaving like first year medical students who startle at every twinge and sniff.

The lawyers bring up the issues, but it is the duty of the experienced business manager to step back and assess the likelihood of a breach.  The mistake people often make is to get the lawyer to make the decision for them rather than use the lawyers input to assess the big picture. The lawyer gets paid irrespective of the outcome of the decision. In the end, the business person must make the business decision and live with it.

Because lawyers are involved in key negotiations, they accumulate considerable “combat time” in business transactions.  This is partly why lawyers end up on the board of directors of corporations. People feel more comfortable having them in the loop for the dicey decisions. 

Chemical Safety- Taking the Dragon Out for a Walk

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Safety is something that everyone who handles chemical substances must come to grips with. That’s pretty obvious.  It is possible to structure prudent handling practices into policies that control how people come into contact or proximity with chemicals.  While I can’t speak for the rest of the world, in the US and EU virtually all of academia and industry have rules that govern the use of personal protective equipment (PPE) and hazardous material storage. 

As a group, I have known chemists to span the range of chemical aversion from compulsive chemophobia to stuntman fearlessness.  Most chemists are in the middle ground in regard to what toxicological or energetic hazards they’ll unleash at arms length behind the sash.  

But there is risk and there is perceived risk and the difference can be quite large.   Research laboratories are places where we try to achieve understanding about the unknown.  Material hazards may not be readily apparent in advance of an experiment.  We all have our sensibilities about what’s hazardous- call it “intuition” or just “experience”- but in reality most workers need to get an occasional recalibration.  Our perception of a given risk can be spot on, overly conservative, or overly lax. 

Institutions eventually have to put boundaries on the definition of acceptable risk. In innovative industry, companies want employees to try new things. Being overly conservative with risk can lead to time consuming procedural gymnastics that accomplish only delay.  Being overly lax with risk can lead to the loss of life and facilities.  The necessary administrative skill is to encourage safe innovation. 

Researchers have physical hazards to contend with. Managers must dodge administrative hazards that can blow a project out of the water. Reseachers operate within the bounds of physical law. Managers have the fundamental forces of economics, politics, and CYA (cover your a**) in addition to physics. 

In candid moments, R&D chemists may admit that much of research seems to entail the discovery of new failure modes. The broad search of reaction space can lead the researcher into patches of higher risk activity.  It is quite possible to blunder into energetic hazards or unwittingly generate highly toxic moieties that you were heretofore unaware of.  The abstracts from a SciFinder search don’t always offer notification of such hazards, especially if you are making new chemical compounds.

I know more than a few reasonable chemists who work for companies that have attempted to extract all risk of R&D scale incidents.  All experiments have to be planned and approved by some overseeing body.  Any incident involving a fire or spill is subject to an investigation and disciplinary action is meted out based on the in-house definition of negligence. Large publically-owned commodity producers seem to be the most onerous in this regard. (This is my opinion and the reader is free to take exception).

As is not untypical of large irritable mammals, Th’ Gaussling doesn’t automatically welcome visits by the safety goonsquad.  One of my many festering conceits is that I write procedures, I don’t follow them.  Unfortunately, this is a card that you can play once or twice at most.  The best strategy for long term employment is to stay off the safety radar screen. If you have to take the dragon out for a walk, have your route planned and for gawds sake, keep it on the leash.

Dark Energy and the Corporate Cosmology

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It is a wonder indeed to behold the awsome forces of the corporate cosmos.  Against the vacuous backdrop of mom & pop businesses and meager franchise operations are the corporate galaxies in this business universe.  There are the super massive galaxies consisting of giant business units orbiting around the central holding company. On occasion, these galaxies collide, sending fragments hurtling into space and leaving a merged core of black holes sucking dividends into the shareholder event horizon to points unknown.

I said it is a wonder to behold. But I didn’t say it is necessarily a “good” wonder.  Occasionally a fellow gets a look into that gaping maw, the churning core of the organizational furnace and sees more than he bargained for. 

To perpetuate the methodical ratcheting in of ever more profit, large corporations filter the continuous stream of applicants for people who can administer the hard-as-steel facts of corporate life.  Certain personality profiles, or folks with certain predilections, need to be advanced in the system to promulgate the mechanical and financial needs of the corporate entity.  Hatchet men and enforcers, rain-makers, and sneering sycophants seem to find these organizations and achieve buoyancy.

At some point a person will run into the reptilian brainstem (management) of the corporation.  Large, impersonal corporate management is the perfect venue for many of our brothers and sisters to express their most antisocial and misanthropic inner selves.  As long as the behaviour is in parallel with the fiduciary goals of the organization, the most vile actions are validated with flippant phrases like “business is business” or “nothin’ personal, it’s just business”. 

The seasoned employee knows that the Human Resources department, for all of the caring talk, really isn’t your friend.  HR is the mechanical arm of the corporate entity that dips into the human melting pot to stir things up from time to time, occasionally pulling out the unsuitable or the plain unlucky for a “rightsizing” exercise.  If you’re aged 50 and well up the pay scale, look out.  That mechanical arm is never far away.

Corporate life has its rewards for certain kinds of people.  Some corporate cultures are better than others. Some understand that they are institutions and have a beneficial role in the advancement of civilization. Other corporate cultures are driven only by the mathematics of growth and are essentially extractive industries charged with the rapid accumulation of wealth by the end of the present quarter.  There is always a rationale for ugly corporate behaviour and there always hordes of aspiring hard-asses trying to get in to do it.  The greedy corporation is a physical manifestation of dark human desires which supplies the tools and opportunities for the acquisitive. 

If some recent experiences are any guide, I have to conclude that civilization is still paper thin. To paraphrase a comment by another blogger, we’re only three missed meals away from anarchy.

PhD Disease. Gaussling’s 2nd Epistle to the Bohemians.

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As I continue to cross off yet more days behind me in the great calendar of life, I am increasingly aware of just how truly strange and perhaps artificial my station in life is. Occasionally I detach my consciousness from the abstractions of my work and intellectual life and join those who live in the “eternal now” of daily life.  It is the world of real estate, car repair, and weeds. 

Having an advanced degree in anything marks a person as a kind of freak.  Not automatically in a pathological sense, though that is possible.  A freak in that to have gotten from freshman year through PhD is unusual in the statistical sense.  Not a large fraction of the population even try to do it.  To have done this is to be relegated to the far end of the bell curve by virtue of low frequency. 

Many people seem to be overly impressed by someone with a PhD.  To be sure, there are many PhD’s who are extraordinarily bright people.  But it takes more than just smarts for most of us.  It requires focus, tenacity, and endurance.  It takes a willingness to absorb abuse as well.  Getting through grad school has a large political component and a wise player learns how to negotiate with difficult people- advisors, post docs, and other faculty. 

Speaking only for myself, I have become quite aware that my path on this adventure will not be followed by any family members. My love affair with the science of chemistry is my lone passion and the wonders and elegance of its form cannot be fully shared with loved ones. That is a shame.

This lurking sensation of strangeness is especially noticeable at parties.  Say you spent the week trying to isolate a new product; noodled through numerous GCMS fragmentation patterns; or attempted to find meaning in the oddities of phosphorus NMR.  Suddenly friday night you find yourself at a party nursing a Fat Tire in a crowd where most of the people are in construction or real estate.  All of the conversations are about, well, construction or real estate. You find a friendly group and try to fit into the conversation. 

But here is the hard part.  You’re not running a construction site and you don’t deal with construction workers.  The price of copper pipe or the vagaries of the uniform building code have no impact in your life.  You’re just a freakish white collar worker who uses vocabulary that means almost nothing to nearly everyone on earth. You worry about selectivity, isomerization, and line broadening.  It really is a bit odd.

So, after you’ve made a few wry comments and patiently listened to the conversation, someone asks the question “What do you do?”.  This is where everything can fall apart.  You want to be accurate, but concise.  You can’t use obtuse language. If you are a synthetikker, you don’t want to say merely “I’m a chemist” because it is certain that the questioner will imagine that you wear a lab coat while you pour test tubes of “toxins” into the river to mutate the poor fishes.  And, for the love of god, you can’t let them think you’re an … analyst.  Good gravy, what would the neighbors think?

No, you say something to the effect that you make some product or other and it is used for ____.  This is that fork in the road that someone will take to get another beer or suddenly recognize some lost associate across the room.  Others will notice that something is wrong with their watch and pull out the cell phone to get the time, feigning discovery of a voicemail that they have to get. There many ways to eject from a conversation gone bad.  I have seen many of them and invented a few myself.

What I hate to see is the person who wears their PhD degree on their sleeve.  The blatant insertion of this status into the mix is like a turd in a swimming pool. Once it’s spotted, nobody wants to jump in.  For myself, I only use the title of “Dr.” in official company correspondance where I have to establish some credibility to weigh in on a certain range of matters.  Otherwise, I will admit that I have this degree only if people ask. The effect of title dropping on certain groups of people is that they shut down discussion when you walk into the room.  This is bad if the goal is to brainstorm or do a debriefing and the result is that people clam up. 

It’s best to let the strength of your arguments advance your cause. I don’t have a PhD in life- just a thin slice of chemistry.  And that slice seems to get narrower all the time.

Scale-Up and the Three Pillars of Chemistry

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The practice of chemistry rests upon three pillars- Theory, Synthesis, and Analysis.  To bring a chemical product into the market place efficiently, a program of development must evolve that rests upon the three pillars.

Ostensibly, in order to rationally synthesize- that is, conceive of a new substance and design a means to bring it into being- it is advantageous to have some kind of theoretical background in order to take advantage of the orbital formalisms of bond making and bond breaking.  It is certainly possible to do chemical synthesis without even a clear notion of atomic theory.  William Perkin was able to embark on a synthesis of quinine and (end up with a synthesis of Mauve Dye) in 1856 without the benefit of molecular orbital formalism. Of course, if he had the formalisms and the analytical technology, he might have actually come up with quinine and would henceforth been known as the father of pharmaceuticals rather than the father of the synthetic dye industry.

I have been witness to numerous product development cycles in the fabulous commercial world of specialty chemicals. If there has been one underlying theme to all of this product development that I have been a part of, it is that synthesis development is typically years ahead of the analytical devlopment.  Allow me to elaborate. 

[Please note that I am not talking about pharmaceutical product development.  I do not operate in that strange universe and I do not pretend to understand it or even desire to be in it.]

Somewhere a company with lots of R&D money to spend and dash of vision will arrive at a stage-gate in its new product development.  A collection of compounds will be identified as having solid potential for use in a profit making chemical enterprise.  Project managers will have to decide on a molecule to launch the project.  The molecule can be a final product with a specific identity, or it can be a substance used to facilitate a technology platform.

The drivers of the project will invariably be synthesis chemists and engineers.  They may choose to make the molecule of interest in-house.  If the molecule or material is the product to be sold, they will almost aways make it in house to capture the economies of vertical integration and scale.  But if the molecule of interest is a reagent, catalyst, initiator, or specialized intermediate requiring some black art, the developers may choose to farm out the molecule. 

In the latter case of reagent, intermediate, etc., farming out the molecule to a specialist vendor requires that the company disclose the identity of the species and probably a synthetic pathway.  Like dogs sniffing one another, a customer and vendor will circle around each other for a short while trying to assess the merits of the relationship.  Once an agreement to move past the disclosure stage is agreed upon, the vendor will set upon the task of noodling out a process. 

I believe it is axiomatic that analytical culture is different from synthetic culture.  Analytikkers live in a world of validation, significant figures, calibration curves, error analysis, and standard test methods.  Synthetikkers live in a world of space yields, solvent effects, reagents, exotherms, hazmats, filtration, distillation, etc.  Each group looks at product development from a different angle and imperative.

Here is the point I wish to make.  Compounds that have been recently discovered and submitted for scale-up are very often “new species”. That is, molecules that are not fully understood in terms of stability, contaminant profile, and importantly, analytical signature.  It would be best to take the time to fully investigate the compound. But to fill out the data table on a species that may not actually go forward is to commit precious time in a very risky way.  Usually, it seems, a candidate for process development is minimally characterized and put on a frantically short timeline for commercialization. 

Another axiom: If there is a hole, someone will fall in it.  Scale-up is often the beginning of the period I refer to as FMD, or “Failure Mode Discovery”.  During this FMD period up to and including pilot scale processing, it invariably transpires that in-process checks and analyses of intermediates is complicated by the improper choice of analytical method and failure to characterize side products. 

In their frenzy to meet deadlines and goals, synthetikkers may not be able to complete a crucial aspect of their job.  That would be to form a complete understanding of the process.  It includes the identification of side products and the fullest characterization of the product as possible.  It is crucial to find in-process markers that indicate that a reaction is proceeding swimmingly or that it is going afoul.  I believe it is squarely the responsibility of the synthesis chemist to survey the composition of critical intermediates and the final product mixture. 

While the preceeding seems obvious and even pedantic, the cost pressures on new product development are often severe and accordingly, processes are rushed out of R&D without much attention to the analytical issues.  I have seen new products from some of the world’s greatest R&D groups hit with severe quality issues in commercialization because analysts weren’t brought in to help with the characterization.

Analysts frequently need input with the development of quality control test methods for new substrates.  This is where the synthetikker can provide the crucial input.  Synthetic chemists must be well versed in the Three Pillars of Chemistry.  We acquire a theoretical background to support our synthetic activity, but we have the critical responsibility of knowing a variety of analytical techniques to validate our assertions that we have made a particular molecule.

Many times in our haste to get a project wrapped up, we rely on NMR for primary analytical data. Very often, NMR is perfectly satisfactory as a stand alone spec, as long as you do not need reliable data below 0.1 %. 

But NMR doesn’t always tell the whole story.  In fact, I have often seen fellow chemists throw up their hands in a gesture of complete frustration and give up when NMR fails to afford a clue to a process or product problem.  Basically, NMR is fast and affords structural details that are unavailable any other way.  Everything else is a science project.  

Having served in business development and product management, I can testify that unforseen quality issues can become show stoppers. It is not unusual to spend as much R&D time trying to noodle out unanticipated quality issues as it took to develop the product in the first place.

It is good to have two or three ways to quantitate purity. I’ve found it useful to have a good relationship with the analytikkers- one that allows for brainstorming and problem solving. 

Contrarian Views on Corn-Based Ethanol

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If you travel through the American midwest, you cannot help but notice that corn-based ethanol is in the news. Over at the Oil Drum blog there is a good post on the merits of corn-derived ethanol (EtOH).  One of the important points that was made is that EtOH will be replacing MTBE as an oxygenating additive. This is an important point. For the near term, as MTBE is phased out EtOH is taking its place.  Therefore, the net effect on imported oil volumes may be nil. 

Then there is the matter of the energy balance for EtOH production.  There is no clear consensus on whether or not corn EtOH production is a net gain in BTU’s.  And then there is the matter of unintended consequences in shunting large mass flows of corn into energy production.

Modern agriculture has been characterized as the process of converting diesel fuel into food. High yield crop production also requires large machinery for efficient cultivation, soil amendments, advanced corn breeding, crop rotation, and specialized pesticides.  And this is just the farming part. Modern grain production requires substantial distribution infrastructure as well as financing for the upfront seed and fuel costs.

By unintended consequences the writer of the Oil Drum post means the possibility of ecological insult resulting from intensification of corn production.  Intensified corn production may result in reduced soybean production in the US, resulting in increased production in Brazil. US farmers may simply choose to grow fewer soybean acres. Increased soybean production in Brazil could result in accelerated deforestation to meet the demand uptick. 

What the writer did not mention is that reduced US soybean production could mean reduced crop rotation, placing increased demand on synthetic ammonia (NH3) production to make up the demand for fixed nitrogen.  Ammonia production uses natural gas (CH4) as the source of hydrogen, and the carbon is lost as CO2.  Increased nitrogen fertilizer use may result in greater run-off into the watershed, placing the aquatic ecosystem under increased stress and polluting drinking water supplies. 

Increased ammonia demand will stress the natural gas market to some extent and result in increased greenhouse gas emissions. 

In addition to ecological insult, there will be a shift of wealth associated with increased diversion of corn to fuels.  If corn yields and acreage cannot be increased to make up for increased fuels demand on corn supplies, the food product chain could be subject to greater scarcity with an increase cost to consumers for everything associated with corn- corn oil, high fructose corn syrup, starch, beer production (!!) with corn starch, cereal products, animal feeds and the associated price uptick that would cause for meat products. 

It is worth remembering that corn is one of the major inputs to our food manufacturing complex. It enters directly as whole corn or as separated corn germ and corn starch, and indirectly as food for hogs, cattle, and poultry.

Many of the choices we have in the supermarket are largely based on what you can do cheaply and on a continuous process basis with grain products.  Stress on this supply will be passed along to the consumer.

One fresh approach is from a start-up company called Zeachem who aims to produce cellulosic ethanol from biomass other than just the corn kernel.  In this process, all fermentable sugars as well as cellulosic hydrolyzates can be converted to acetic acid by fermentation and the lignin sidestream can be processed to yield hydrogen.  Esterification with process ethanol to afford ethyl acetate followed by hydrogenation yields EtOH.  This process is currently in scaleup and may prove to be a major improvement in the otherwise anemic economics of EtOH. 

Adventures with Chemical Customer Service

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For novelty I like to do raw material sourcing from time to time.  Trying to find exotic materials, equipment, or services is a sort of treasure hunt.  Like everyone else, I enjoy the thrill of the hunt and the satisfaction of finding a good buy.  What is striking is the great variation in helpfulness among customer service people.  Just today I encountered a customer service rep who was most helpful (Company W), and one who was, how shall I say, a miserable and unhelpful little snit (Company A). 

I’ll do a compare and contrast.  The helpful rep from Company W listened to my recitation of requirements and offered the best fit from their extensive collection of products.  We discussed the parameters and came to a conclusion. The rep offered to send a free test sample of product which will arrive by mail in a few days.  I’ll do a benchtop test and we’ll see if it works.

The insufferable snit from Company A listened to my requirements and, because I didn’t have a specific particle size to offer, just a SWAG (Scientific Wild-Assed Guess), was unable to make any kind of suggestion at all.  Because I did not input exact information so this person could go to an specific location in the table, the entire collection of products from Company A were made unavailable to me. 

I was shopping for filter media.  I’m interested in coarse, medium, or fine.  Because Company A offered 20 products specified to the nearest 0.1 micron, and because I could not offer an exact match, the Company A snit rep was unwilling (unable, perhaps) to help me make some educated guesses as to which product was most satisfactory.  What really irritated me was that there was not a smidgeon of help.  Just silence interrupted with staccato bursts of “I can’t help you if I don’t know the particle size…” from the other end.  Sigh.

You know, I have been filtering things since the early Disco Epoch, and until just today I did not know that ignorance of particle size was a show stopper.  

Thus begins the take-home lesson. I’ve spent many hours doing customer service, so here are some observations.  Very often a potential customer does not know what they really need.  Remember, there are wants and there are needs. They’ll call with some vague notion of what they want, but it might be very superficial.  They’ll pose and swagger like they know what they want, but chances are that they are fishing for clues from you, the customer service rep.

A good customer service rep has to know a great deal about the products and their typical use. A good rep will ask probing questions that drill into the customers knowledge and begin to find patterns and show stoppers. the good rep helps the customer sort between wants and needs. 

A customer service rep is also a sales person, whether that is openly acknowledged or not. The rep should try to find the best fit for the customer from the company selection of products. But now and then, the company may not be able to offer exactly what the customer needs and should just say so at that point.  The customer will leave with a good impression of the company and may return one day with a spec that matches your products. 

The rep from Company A did a disservice to his/her company by prematurely cutting off the shopping phase of my query.  It boils down to simple ignorance and the lack of basic curiosity.  There was no offer to ask someone else nor was there an offer of a reasonable substitute. They will miss out on a sale and will never know that their loss was self imposed.

J.Org. Chem. Git ‘er done!

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Citations taken from JOC, 2007, 72, 3981-3987, by Bruce Ganem and Roland R. Franke.

Where observation is concerned, chance favors only the prepared mind.  -Louis Pasteur

Necessity is the mother of invention.  -Anonymous Latin saying

Git ‘er done!  -Southern country male expression (recently popularized by Larry, the Cable Guy)

That’s hilarious!  I’m not sure, but this may be the first reference to a Comedy Central character in an ACS publication.  Well, I’m fairly sure.