On the Road in the Land of GM

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Th’ Gaussling has been on the road the last few days visiting one of the states shaped like an oven mit up along the north coast.  This is my first visit to this area during the summer. It is very beautiful country.

We had an inflight medical emergency enroute to a stop in the Windy City.  The call came over the PA “Is there a doctor on the plane?”.  Two vacationing MD’s, one in a fishing vest, rendered aid to a fellow who had a seizure.  They had the poor sod on the floor with a saline i.v. and O2 for 90 minutes. The guy was lucky that he had more than an Untied (Airline name purposely altered) Stewtron to look after him. A business associate had the same experience the same day on the same route, but on a different flight. Curious.  [Note to self: Bring meds on trip.]  

Late Night Thoughts on Twisters

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Now that we are well into tornado season in North America, I thought I’d dredge this old post up out of the cobwebs in the dungeon. As Uncle Al pointed out in the comments, Middle Easterners did have dust devils so a vortex of wind was not unknown there. These, however, are no match for a full-blown F4 tornado.

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One has to wonder what the original inhabitants of North America thought of the tornado (how do you say “WTF” in Lakota?). I have visited a few museums in my travels but have never seen any artifacts or heard of any references to Native American perceptions of the tornado phenomenon.  Without a doubt, Native Americans were visited by tornadoes. The experience must have certainly left an impression. It would be interesting to hear any stories that may be out there.  An internet search just offers a Mulligan stew of hits with tired references to Pecos Bill or to the odd disaster in Kansas.

North America is climatically privileged in that there is the possibility that overland southerly flows of cold dry air from the north can readily contact flows of warm moist air from the Pacific, Gulf of Mexico, or the Atlantic.   Vertical mixing of unstable humid air results in convection cells that are further driven by the latent heat of condensation.  These humid flows are spun up by the coriolis effect and wind shear to afford monster anvil storm cells that can tower to 50,000 ft or higher.

Like many places, here in Colorado we often see lines of isolated storm cells in the early evenings of summer, red in color at low altitude changing to a billowy yellow-white at altitude near sunset. Very often you can see mammatocumulous features signifying violent mixing activity. It’s no place for an airplane.

It is interesting to speculate as to how our modern mythologies and iconographies might have been different if the tornado phenomenon had been common in the Mediterranean and the middle east.  Would Charleton Heston have summoned a tornado to smite Yule Brynner’s Egyptians rather than parting the Red Sea and drowning the buggers?  Perhaps the Pharaohs might have built great stone helices rather than oblisks.  Aristotle might have written a treatise on the handedness of helical flows or whether the air flowed radially into or out of a tornado.

If the tornado had been a common phenomenon in the middle east during the iron age would the “Big Three” Abrahamic religions today feature tornadic themes in their texts and monuments? If so, perhaps the great cathedrals of Europe might today have relief sculptures or stained glass windows portraying the Israelites or Philistines being driven hither and thither by the swirling wrath of the Almighty’s cyclone.

Well, that’s enough of that.

Nitroalkenes

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A nice preparation of nitroalkenes appeared in the latest JOC.  The work was reported by Concellon, et al., JOC, 2007, 72, 5421-5423.

I like the two obvious aspects of this work- catalytic use of NaI and the use of SmI2 for functional group modification.  The use of 0.15 eq of sodium iodide to catalyze the condensation is really clever.  The yields are reported to range from 55 % to 96 %. A few yields are in the mid 50’s range yet no mention is made of dimerization of the bromonitromethane, so I can assume that is not much of an issue. 

Nitroalkene prep

The process uses an excess (2.5 eq) of SmI2 to afford overall 2 electron transfer to the substrate, resulting in loss of Br dot and oxygen, yielding an olefin with good stereospecificity.  For the examples given, the E/Z ratios were all 98/2. 

There are some downsides to the chemistry, I’ll admit. Plant management may not be keen on nitromethane derivatives.  I know that nitromethane has been shown to be shock sensitive in the BOM impact test (personal communication).  Depending on their threshold for these things, the plant safety patrol boys may have misgivings. 

The economic merit of scaling up a process that uses SmI2 depends entirely on the value proposition, which can be readily calculated.  Rare earths are reportedly of low toxicity, though I have not seen a primary reference for that assertion.

Most of the rare earth elements come from FSU or China. There is an accessible supply outside of the usual catalog companies, though you may have to do an electronic funds transfer in advance to some cramped office in Shanghai with a rep named Sylvia or Frank.  Advanced payment and sketchy D&B data will make your accountants skittish. But it could be worth it for bulk material.

I’m increasingly aware of the interesting utility of more than a few of the rare earth elements.  My work post-academia has taken me to many far off and exotic locations on the fabulous periodic table.  The rare earth group is not the featureless corridor of nondescript trivalent cations that this organikker once believed.  Fancy that.

Good Customers and Bad Customers

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Even the biggest pollyanna in the sales group will discover one day that it is possible to have a bad customer.  Yes Johnny, it is a fact that not all customers are desirable.  Oh I know, in sales one is always rabid to close the deal. Get the sale and move on to the next prospect with a pulse. But what is the difference between a good customer and a bad customer if their money spends the same?

Ideally, a “Great” customer comes back for repeat business, is flexible on terms and conditions, pays 30 days net, gives long lead times for delivery, accepts FOB terms, accepts delays and price increases without protest, and picks up the dinner tab when out for a visit.  [~~Sound of needle scraping across phonograph album~~]

If only such compliant customers existed (Sigh).  In reality, most chemical customers are in what I would call the “Good” category.  That is, they have reasonable expectations of price and delivery as well as an understanding of what constitutes fair business practice.

But on occasion one runs into what you might call a “bad” customer.  Such customers are found across the entire spectrum of size and business model. 

A bad customer is one that consumes excessive resources during the course of service.

A small bad customer might want you to do free product development for them, or may try to negotiate bulk pricing only to turn around and try to get bulk pricing on small quantities. Bad customers may finagle front-run samples from you and then disappear for months or years without a peep.

Large bad customers like to throw their weight around.  They know they are above you on the food chain and behave accordingly.  They dangle promises of big and long term sales and wangle free services from you. Services like gratis process development, holding inventory for free, tolling or other business agreements that tie your hands and force you to open your books for their auditors.

Bad customers large and small have other maddening habits that consume resources.  Specifications that change over time, always to the side of higher stringency, are a favorite of bad customers.  Bad customers will discover that they can shave costs by elaborate just-in-time delivery schemes with favored shippers, a circumstance that will require full time attention by logistics people and production managers.

Bad customers want the transaction to follow their particular terms and conditions. Bad customers will want 60 days net- a particularly transparent scheme to float their resources in interest bearing accounts while the vendor has to finance manufacture up front.  The fetid odor of MBA finance people lingers here.

Bad customers will want their vendors to provide indemnity to shield them against any conceivable liability related to the product.  Bad customers will want to own any and all inventions pertaining to process improvements relating to the product. They’ll want to be free to take this improvement and hand it to your competitors in order to generate a tidy little bidding war over their business. 

Practices that I have been calling “bad” are generally accepted in the business world.  On the buy-side they are considered good practices.  On the sell-side they are arguably bad practices because they increase risk and expense related to the transaction. A good buyer tries to implement these bad attributes.  A good seller tries to eliminate or minimize these bad attributes. 

In the real world, one rarely has the option of walking away from bad customers.  But it is possible to stand firm and prevent profit erosion.  Very often a customers apparent demand is just a straw man.  If not entirely a bluff, it might be negotiable to some reasonable concession.  The best practice is to be up front with your concerns and communicate with the customer. They are nearly always reasonable.

The 80/20 rule often applies to customer service:  20 % of your customers will take 80 % of your time. This is life in the fabulous world of sales.  Every sales person must eventually come to terms with it.  Sales consultants talk about “qualifying” sales prospects, but that only applies to real estate and vacuum cleaners.  The world of custom business-to-business chemical sales is such that if someone can identify your product and seek your services, they are almost always a legitimate player.

National Aphorism Day

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Below are a few quotations that patch together is a particular way.  

Here is a great quote lifted from the internet. With any luck it is accurate-

 “They lied to you. The Devil is not the Prince of Matter; the Devil is the arrogance of the spirit, faith without smile, truth that is never seized by doubt. The Devil is grim because he knows where he is going, and, in moving, he always returns whence he came.” (Umberto Eco, The Name of the Rose)

Here is another good one-

“When a government is dependent upon bankers for money, they and not the leaders of the government control the situation, since the hand that gives is above the hand that takes. Money has no motherland; financiers are without patriotism and without decency; their sole object is gain.” (Napoleon Bonaparte)

And then there is this-

“Ask a Soviet engineer to design a pair of shoes and he’ll come up with something that looks like the boxes that the shoes came in; ask him to make something that will massacre Germans, and he turns into Thomas F–king Edison.” (Neal Stephenson, Cryptonomicon)

Neal Stephenson’s book, Cryptonomicon, is quite good though ponderously large.

B-24 Liberator in the Morning Sky

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This morning while on a pleasant bike ride through the countryside I chanced to hear a familiar rumbling noise.  Not seeing anything immediately, I stopped to look at a pony and a mule that had gotten loose from a pasture.  Moments later, over the cottonwood trees there appeared a B-24 Liberator flying overhead not more than 1000 ft above ground.  This is something you don’t see every day. 

Turns out that the owners of this aircraft were flying out of a local airport over the holiday selling $400 rides in this lumbering relic of another age.  Hell, if I could justify it to my wife, I’d have taken a ride too.

M.S. Kharasch, Merthiolate, and Autism

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One of my most prized books is a tattered copy of Grignard Reactions of Nonmetallic Substances, by M.S. Kharasch and Otto Reinmuth, published in 1954 by Prentice-Hall.  It is a 1384 page tome containing a vast number of examples of Grignard reagent chemistry and reaction chemistry with extensive references through 1954.

Morris Selig Kharasch was a professor at the University of Chicago and is primarily known for his work with free radical chemistry.  To Kharasch is credited much of the early work in sorting out the mechanism of anti-Markovnikov addition of HBr to olefins. Reinmuth was the second Editor of the Journal of Chemical Education (1933-40).  Two coworkers, Frank Mayo and Cheves Walling, went on to make contributions toward the development of vinyl polymerization.

Later in his career Kharasch turned to the examination of the Grignard reagent and many of its reactions.  Among the list of his students and post-docs are H.C. Brown and George Buchi.  Kharasch was instrumental in the founding of the Journal of Organic Chemistry and served on the Editorial Board for many years.

It is interesting to note that Kharasch is credited with the patenting of Thimerosal in 1927, a product also known under the trade name Merthiolate which has been used as an antimicrobial additive in vaccines.

Rhubarbarita Organoleptic Trials

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Th’ Gaussling has been a lazy blogger lately.  Life has been intruding into my blogging time. 

This weekend I’m gonna try ginnin’ up a batch of Rhubarbarita’s. Rhubarb is a good natural source of oxalic acid (for the uninitiated, that was a joke).

Being from the Iowegian belt of middle earth, I have a fondness for porkchops and rhubarb pie.  I know- it’ll kill me eventually. 

Rhubarbarita Update.  I prepared ca 500 mL of rhubarb juice for formulation experiments. To a stainless steel 2 quart pot was added ~500 g of rhubarb stalks cut into chunks ~2 cm in length and taken to a reflx in a 2:1 mixture of water:Karo corn syrup with a lid on the pot to help retain volatile flavorants.  The chunks were boiled for 10 minutes whereupon they began to disintegrate.  The stalks were crushed and the resulting slurry was separated via metal strainer. The greenish solids were discarded and the resulting cloudy pink extract was charged into a sealable container and refrigerated. 

The purpose was to obtain a rhubarb syrup suitable for formulation with various liquors, Tequila in particular. Corn syrup was chosen for sweetness and viscosity. Some observations from the organoleptic trials-

  • Rhubarb juice prepared in the fashion described (vide supra) has a low flavor potency with only a small amount of tartness. It has a distinct flavor and agreeable color, but does not jump out at you.
  • Rhubarb juice has little natural sweetness, so a sweetner must be added to provide the expected mouthfeel and sweet aspect worthy of a drink fitted with an umbrella.
  • The 2:1 ratio of water to syrup is not satisfactory in regard to sweetenss or viscosity.  A 1:1 ratio should be tried.
  • As the sole flavorant, the rhubarb extract is not flavor-intense enough or exotic enough to expect repeat consumption from foo-foo umbrella drink consumers when used for Margharita formulation.
  • A properly formulated Margharita on the rocks should have good mouthfeel with sweet and tart attributes as well as a jab of citrus in addition to the exotic agave flavor of the Tequila. 
  • The addition of lime juice was found to markedly improve the organoleptic test. 

In summary, the experimental Rhubarbarita described above was judged to have an acceptable flavor, though hardly exciting or memorable.  It was found empirically that the addition of fresh lime juice contributed substantially to the overall impact of the formulation. The impact of a “bottom shelf” Tequila for the experiment is unclear at this time.

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.