Monthly Archives: July 2007

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.