Category Archives: Chemistry

Halogenate with extreme prejudice

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Reacting one element with another to make a compound. How much more “elemental” can it get? No solvent and no waste, just element on element at Venusian temperatures. But, an organikker doing inorganic synthesis?  Is this a Coen brothers movie? What strange overlap of events lead to this redox redux?

Paracelsus would have been pleased at this transformation, though his interests with this compound might have diverged from mine. Whereas I as a modern chemyst would add a nucleophile to my blessed conjugation of elements, Philippus Theophrastus Aureolus Bombastus von Hohenheim (Paracelsus) would probably have more mundane applications like the treatment of consumption or perhaps an indelicate medicament for that tell-tale abscess.

After a career of conducting elaborate procedures for the preparation of strange organic compounds, it is refreshing to spend a month performing a non-incandescent combustion of elements.  There is joy in doing a thing well, taking the elements to their endpoint as fast as the equipment will allow. Squeezing maximum performance from the system and myself. It is a kind of poetry in motion. 

Frequently wrong, but never in doubt

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More and more I find myself afflicted with fellow travellers along the timeline who are never in doubt of their judgement, but they are frequently wrong nonetheless.  There has to be some archetype from literature or Greek mythology that symbolizes this. Maybe there is some character from a Greek tragedy who, as a leader, was destined for a fall as a result of such a trait. Perhaps someone out there has a nominee for this position.

One sees examples of this in business organizations not infrequently. Some openly discuss their views, but often with the presumption of making a disclosure of “what we’re going to do”.  Others sit quietly, rarely contributing to open discussions where ideas are put on the table for dissection.  These fellows might listen to others debate, but they prefer to sit quietly and observe while others reveal the content of their thinking. Rather than adopt or synthesize new concepts openly, they will tend to note commentary that aligns with their pre-existing view. This is where that most loathsome of characters, the yes-man, can gain a strong foothold in an organization. 

Howard be thy name

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A few posts ago I wrote about buying chemicals from Asia. I mentioned the weakness with shipping. But there are other snags in the system to contend with.  Recently I received a parcel of non-hazardous material that I bought from China. I have been trying to source this stuff for years and I finally found a candidate vendor. We already make the stuff, but we’re short on capacity.  The qual sample was a white granular product and was packed in thin plastic zip-lock sandwich baggies jammed into a used stereo speaker box (!!@#*!). Hell, the foam part for protecting the speaker was still in the box. OK, not smart. And it was mislabeled as some other product. That was the really dumb part.

Torqued about this, I fired off a grim and terse torpedo-gram expressing my shock and dismay at their poor judgement in these matters.  The vendor rapidly replied, exclaiming in much poorer English this time, that since it was a colorless solid product, they believed there would be “problems” shipping it to the USA.  Well, let’s see … hmmm.  It is TSCA listed, it is non-hazardous, no conceivable abuse issues, it is a salt so it won’t burn, but if you dropped a 200 kg drum of it on a cockroach, the cockroach might die.  Yeah, they thought it would be suspected as an illegal substance so they would be clever and ship it under another name. But it is ACS grade material completely innocent of any conceivable abuse potential.  So by being “clever” about it, they revealed their facility with underhandedness.  How can I go forward with a vendor willing to do this crap?

So, you might be tempted to think “Golly, they’re some pretty dishonest chaps”. Well, I’m not sure yet. They may be redeemable. Thank Howard, I myself have been given many second chances. It’s a karma thing. So we’ll inch along and see how they do on the next round. I suspect they’re just naieve in these matters.  Never attribute to malice what you can first explain by ignorance.

Moral of the story- just be honest and above board in all of your business dealings. Ya can’t fall off the floor.

Update:  It was suggested that this is actually a ploy by the exporter to get around import duties.  Well, I’ll happily pay the duties rather than monkey with this sort of thing. Crimony.

Chemical Logistics

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Any chemical company manager will have to admit that order fulfillment isn’t over until the product is in the hands of the customer.  Chemical manufacturing isn’t just about running reactions in big pots.  It’s about attracting a skilled, reliable, and safe work force. It is about building a supply chain for the timely delivery of raw materials. It is about executing the manufacture of products in spec the first time through. It is about warehousing raw mats and products and keeping the stream of wastes moving through the system.

Chemical manufacturing requires the careful management of cash flow by minimizing costs and maximizing profits. The business office must attend to receivables and collect payments in the most expeditious way that customers will tolerate. This is no different that any other manufacturing arena- sprockets, fur caps, or rocket motors.

One of the key jobs required of any chemical company is the matter of managing logistics.  That is, managing the timely transport of raw materials onto the site and the transport of products off the site. So how does this affect the chemist??

The tender shoot studying chemistry in their junior year of college may not know it yet, but if their path is in the fabulous world of business, then some aspect of logistics may be in their future.  What kind of chemist would need some knowledge of shipping? Well, project managers, sales managers, business development managers, plant managers, procurement managers, etc.  All these positions are often filled with chemists and all have to have some knowledge of this topic.  And how does one get this knowledge? Why, on-the-job training, of course.

If you have read many of my posts, you know that I tend to prattle on about this. There is a reason. It is not uncommon for a sales person or a business development manager to spend no small amount of time with a customer trying to work out how the product will be delivered.  The transport of materials is complicated in proportion to the hazard and the chemical sensitivity to decomposition. 

Let’s say that you are in the chemical business and you are just starting the custom mfg of a trialkylphosphine.  The customer will state that they want say, 100 kg, of their R3P with a list of specifications (e.g., 99% in R3P, oxides < 0.1 %, etc, Karl Fisher water 200 ppm) for their new product. The customer has accepted the quoted price and the delivery date. Hmmm. Price, delivery, and specs. Sounds like everything is in place.

So, the question then arises: How are you going to ship it? Glass bottles? Drums? Polyethylene totes? Whoops, the material is excruciatingly air sensitive, so charging and discharging the product will have to be done airlessly. Sounds like a cylinder is just the thing. But what are the materials of construction? I seem to recall that phosphines are ligands, so can we really use a steel cylinder? Soft steel? Stainless steel?

But there is yet another question.  Do we offer the phosphine neat or as a solution? If the neat R3P is a liquid, we can move it around airlessly and charge a cylinder with it. If it is a solid, then it could be a serious problem to transfer it from a filter to a shipping container. How will you or the customer actually handle it? This is the kind of detail that chemists might find themselves groping with. If it is a solid, the customer might have to consider receiving it as a solution in a non-interfering solvent.

Then the matter of transporting it arises. In the present epoch of security theatre, air transport of any quantity might be banned. So, surface shipment will be needed. The matter of heated shipment may arise if freezing or precipitation is an issue. The last thing anybody needs is a cylinder full of precipitated solids in it.  Remember, if you are shipping product in a heated trailer in the winter, you may have stiff competition from other customers who need to ship their lettuce or strawberrys. In some locations, reefer trucks as they are sometimes called may be in short supply.

OK. So you’ve specified a reefer trailer for heated transport of the goods. Let’s say that the product solution will crash out precipitate at 15 C. In the trailer everything is just fine. Fine that is until the shipper reaches a transfer point and moves the product out onto the loading dock where it sits in the freezing weather for a few hours waiting to be put into another trailer. Or it sits in unheated warehouse space for a while.

Eventually, the cylinder of R3P solution arrives and, sadly, has precipitated and won’t come out of the cylinder. So there you are. The customer is unhappy and you now face having to haul it back and recover the product. These are the kinds of problems that chemists on the business side (the plow horses) can find themselves dealing with. Of course, the R&D chemists (the show horses) are rarely bothered with such things.

On Extracting Abstractions from the Abstracts

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One of the chores that must be done when developing a new technology is “Due Diligence” as applied to intellectual property.  In the fabulous world of industrial chemistry, there is an overlapping of the three great magisteria- Business, Chemical Science, and Law.  In order to get a new product or process on stream, we must find a line of sight through the many hoops and past the many gatekeepers of those magisteria that can obstruct our path the fame and fortune. 

First, allow me to pay homage to two great and wondrous database services- the United States Patent and Trademark Office (USPTO) and Chemical Abstracts Service (CAS).  They are the custodians of data generated by some of the most cantankerous and unruly people on earth- lawyers and chemists.  Their task is complex and effectively endless. 

In actually trying to do a reliable due diligence analysis, a searcher must ascertain that a proposed bit of IP does not conflict with claims in valid patents owned by others.  In a chemical IP search, one can divide the claim universe into 2 domains- composition of matter claims and process claims.  In the patent, the first sentence will state whether a composition is being claimed or that a process is being claimed. Some patents have both composition claims and process claims.

So here is the problem.  Let’s say that you are trying to determine whether or not you have the right to manufacture a particular molecule. This apparently simple question actually deconvolutes to two fundamental questions: 1) Is the composition of matter in the public domain? And, 2) are there claimed processes for it’s manufacture? 

There is a third domain and that relates to the use of the composition.  However, this does not impinge on the right to manufacture the material, just it’s use.

If the material is claimed as a 1) composition of matter in a valid patent, then you cannot lawfully make it or possess it (for commercial use, though precendence is being set for a bar on R&D use as well) without the permission of the assignee of the patent. Note that the owner of the patent is the assignee, not the inventor(s). If the composition of matter is not claimed, then it is in the public domain, assuming that you did not learn of it under trade secrecy. 

So, let’s say then that your target material is in the public domain. Now the question is 2); does your proposed method for its manufacture infringe on claimed methods? This may be a hard or expensive question to answer, and the reason is plain.  When you execute a search for IP issues related to a substance, you search path is limited to fields, key words, structures, CASRN’s, etc. that are flagged in the major databases. 

A CAS search on a given compound will lead to patent families that mention the compound, its preparation, or its use. But you have no way of knowing whether the patent reference claims the composition, its preparation, or its use.  It could very well be that there are no claims pertaining to the compound of interest- it was just cited as an example of some sort.

A CAS search is highly accurate in terms of the focus on a particular compound.  However, a USPTO search is not. A chemical search of the USPTO public database (USPTO.gov) is pretty much limited to a search for specific character strings.  It is possible to narrow down the scope of a search by concentrating on classification numbers, but I have never been convinced of its thoroughness.

After all of this set up, here is my point.  The problem we all face in doing our IP due diligence is that there is no direct means for determining from an indication in a database search report whether or not a composition is in the public domain. A CAS search will not yield a clear yes or no, and the USPTO database search only retrieves hits that have the requested strings.  Despite the advances in database technology, the user still has to collect all of the patent citations pertaining to the material and sift through them and interpret the claim language. 

Wouldn’t it be useful to the public if an applicant for a US patent were required to collate the claimed compositions for uplink into a database?  With such a “field” in a CAS or Beilstein search, you could tell in an instant if the composition was claimed. The same argument holds true for processes.  At present, the “retrievability” of claimed art is poor.

Patent attorneys are likely to object along the following arguments: not all patents that you retrieve from a search on CAS or USPTO will be valid.  Some patents will have expired naturally, others will have expired for non-payment of fees, and still others will have serious weaknesses that will only be apparent from an examination of the prosecution history as revealed in the file wrapper.  Abandonment may be difficult to detect for abstracting services, as would flaws in the prosecution as documented by the wrapper.

Another objection that is unlikely to be openly identified is the matter of clarity.  There is may be advantage conferred to assignees when a claim is a bit fuzzy.  This may afford some manuevering room during an infringement action, though it might be hard to say who the beneficiary would really be. I would estimate that whomever had the most persuasive attorneys would prevail.

It would be interesting to hear from others about this matter.

Importing Chemicals From Asia

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When you are involved with sales, you have to wake up with three words on your mind every morning- Sell, Sell, Sell. In the fabulous world of chemical business you can either make stuff or re-sell stuff. Sometimes you do both. After all, you can’t make everything.

A well run mature chemical business will have more opportunities than capacity. By contrast, an immature company may have more capacity than opportunities.  Many companies get to the point where they have to start choosing which customers they want to make the happiest because they are low on capacity. During the ups and downs of the business cycle, plant capacity goes from abundant to slim and back. It is the job of the sales person to keep the plant booked solid.

When your plant is at capacity, a funny thing happens.  It occurs to people that not all products are equally desirable. That is, some products are more profitable than others. When this is the case, management will start to wonder why they are spending scarce reactor time with products that are the least profitable.  Suddenly, products that have been steady money makers over the years begin to look a little anemic.  Pretty soon, these products are seen to be liabilities of a sort.  There is loose talk about pushing them back on the timeline; of offering 12 week lead times rather than 4-6 weeks. Then one day, they are off the production schedule. It has been decided that we can no longer afford to “neglect” other products because of these lower dollar products.

So what do you do? There is still a market out there for these orphaned products. Here is one option.  You outsource the product and resell it.  The trick is to find a supplier whose price is low enough to allow for a decent profit when you resell it.  In fact, this is a way to increase plant capacity without having to buy any real estate or pots & pans. If you can pull it off, you might even come out looking like a flippin’ genius.

The trick is to find a low cost source- preferably one whose selling price is less than or equal to your old manufacturing cost. This allows for the profits that are the same or better than before. So where do you go?  Commodity feedstock costs tend to be similar around the world. But in some countries, labor costs and overhead may be dramatically lower.  At the present time, Asia- China and India- are attractive locations for low cost manufacturing.

But, buying from Asia may be trickier than you think and for reasons that you have not considered.  Neglecting import duties which may add 0 % to 10 % (or much higher) to the cost, and neglecting tranportation costs and delays, you have to think about how the actual business transaction is going to work. 

Here is the problem:  You want to start buying from a new manufacturer or trading company in Asia.  Now, I’m not talking about the the pharma business- I’m talking about fine chemicals. There is a good chance that whomever you contact on the web is not going to be a factory person. It is likely that your contact will be a trader of some kind. This is very common in Asia. My experience has been that these traders will represent a “stable” of manufacturers who have some kind of agreement with the trading firm.  In fact, making a direct manufacturer could prove to be difficult if you are limited to internet searches.  The best way to meet manufacturers is at a trade show.

The contact is likely to want prepayment at least initially, unless your name is Pfizer or DuPont. So, you will have to send a purchase order and do a wire transfer of some funds. That’s easy enough.

The question is, do you really want to do a prepayment? What if there is a SNAFU and your payment is taken, but the product isn’t shipped? In the US, you’d have some recourse in the civil courts.  Or, what if the quality is inferior?  You might find that getting a replacement or a refund is … difficult.

I have not yet had a really terrible experience with importing. At least not involving anything underhanded. Most of the problems that I have seen involve logistics. Yes Mr or Ms chemist, if you are to be involved with outsourcing in a non-trivial way, you will have to learn about the transport of hazardous goods. International transport of chemicals, hazardous or not, is a multimodal affair involving ground transport on both sides and air or ocean in between- trucks, planes, container ships, FedEx, UPS, DHL, etc.  Some things you can ship internationally by air and others have to go by boat. Remember, there is no overnight to Asia or Europe. At least without hiring a private jet.

Outsourcing involves way more than just finding a vendor and a good price.  Before you commit funds to the purchase, you MUST ascertain that the stuff will arrive in a timely fashion.  It has been my experience that Asian chemical suppliers I am familiar with  have gotten really good in the manufacturing part, but they are often lacking in the logistics part. 

When you contact a new Asian supplier from the USA, it is critical to drill in to find out just how they intend to ship the materials and what the Incoterms are. And here is a really important part, so put down your yogurt and pay attention. You have to get familiar with Incoterms. It is critical that you understand who is responsible for arranging for what and where you take ownership of the goods.  The sellers price will vary depending on the Incoterms. 

A common term might be “Ex-Works”, meaning that the seller makes the goods available on the sellers premises, and it is the buyers responsibility and risk to arrange for transport from there.  EXW strongly favors the seller.  Other terms include CFR, “Cost and Freight”; CIF, “Cost, Insurance, and Freight”; FOB, “Free on Board”; DDU, “Delivered, Duties Unpaid”; and DDP, “Delivered, Duties Paid”.  All of these terms have specific meanings with the responsibilities and liabilities defined. These terms may be negotiable.

For an R&D sample, these transportation details are not a big deal.  But for bulk materials, you can experience failure modes you never dreamed existed. There are companies that specialize in the international movement of materials. It is always best to engage a logistics firm to help with the coordination. For example, if you were going to send a cylinder of butyllithium to Argentina, how would you do it?  See what I mean?

Gaussling’s First Epistle to the Bohemians

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Like nearly all chemists practicing today, I was hatched from a university chemistry department and tossed into the big, big world.  Like most Ph.D. hatchlings, I had developed a bit of a swagger. I somehow managed to get into and survive a good research group with more than a third of my sanity and ego intact. Part of the real value of an advanced degree is the fact that you have survived a very elaborate ordeal and gotten across the finish line. Yes, I was able to drag my battered remains across the finish line with my remaining good arm. 

University training doesn’t exactly prepare you for all of the outrages challenges that lie in waiting for you.  And, it really can’t do that.  University training does give a basic skill set from which you can build upon.  Which brings me to the point of this little epistle.  What you’ll find when you get into the world is that there are many more really smart people walking around that you might have considered.  Not all of the smart people actually matriculated and studied chemistry.

One of the smartest people I know is an electrician friend.  I worked for him for a while during some hard times and he actually tolerated my presence with grace, useless though I might have been at bending pipe and pulling wire. He has this uncanny ability to get things done.  This is an attribute that is absolutely golden.  Crimony, I nearly killed him one day when the backhoe I was operating swung out of control when some frozen ground gave way suddenly, causing an unplanned control input.  The bucket swung over and stopped short right at his chest.  He didn’t bat an eye.

He once pointed out that you have to expect to take a lot of hits. The goal was to minimize the number of hits you take below the waterline. 

It’s good advice and I’ve never forgotten it.

Chemical Advertising

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For the past eight years I have been involved in advertising the goods and services of my company.  I have designed a series of ads you’ve seen in C&EN and I’ve just recently gotten a trade name through the trademark process at the USPTO.  I have been deeply involved in the design several iterations of chemical catalogs and web-sites. 

What has been interesting about this experience is the chance to witness up close how the advertising business works.  I have been an industrial chemical sales manager, so I can spot salesmanship a kilometer away.  In some respects, my chronic exposure to it has built up a resistance to the enchanting ways of the art.  But I have nothing over advertising account managers (a.k.a, advertising sales people).  These people are smooth.

It has been said that 50 % of all advertising is wasted effort and money. The trick is to figure out which 50 %. Advertising is something you know you should do, but the question is, how much should you spend and what should the message be?  Ah, that is the trick.  An advertising rep will encourage you to spend as much as possible.  They understand your uncertainty and trepidations, but they are in the job of selling ink & space.

The uncertainty over what and how to advertise is always there, but it is possible to put some boundaries around it. You do this by having an advertising budget. At minimum, this limits the cash bleed out in advertising costs.  Pretty elementary so far.  Next you have to decide on a message and an image.  Sometimes the image is the message. Other times, you will want to trot out specific goods and services. 

Within your company, just as everyone believes that they are an expert in pricing, everyone will have the same certainty that they are an expert in how to design ads.  I bring this up because rarely will someone have complete and solitary control over the design of an ad campaign.  There will be input from all levels- from the janitor to the CEO- however, some opinions are more important than others. If the CEO or other officers of the company don’t like the ad campign, then no matter how brilliant or clever it is, the thing is dead.  Like death and taxes, it is an elementary fact of life.

Selling chemicals is not quite like selling fragrances, apparel, or cars.  In advertising chemical goods and services, you can’t overtly appeal to the vanities controlled by the gonads.  People do not buy chemicals to fulfill some notion about their identity.  They buy chemicals for the same reason people buy cordless drills, 2×4’s, and bolts.  They are going to make something else or use the chemical to achieve some purpose other than simply being in possession of the material.  Owning a pile of KOtBu or a drum of DMF does not confer any upper eschalon status that I am aware of. It might alarm the local authorities, though.

But there is one vanity that a chemical sales campaign can appeal to: that is the need to have achieved a good “buy”.  Being a smart buyer feels good. Having a track record of being a smart buyer will help your company and will give bouyancy to your career.  People are always looking for a good deal and the advertiser needs to focus on this need.

But a smart buy isn’t simply about low unit price.  Availability and quality are important as well.  Nothing sours people quicker than the realization that they have been duped with an inexpensive purchase of low quality chemicals or late delivery. So there is always the need to balance price with quality and delivery.

Some companies are very smart about this.  Take SAFC (“Aldrich”) for instance.  Aldrich tends to be a premium supplier of chemical products.  While their catalog prices tend towards the higher side of average, at least by my observation, you can depend on high quality and fast delivery. They have built a successful institution on high quality and excellent service.  When you pay $80 for a gram of something, you are paying for good quality stuff and the price of near instant availability.  The fact is, most people are willing to pay the price for availability.

So, while you can’t take the “Give Her Diamonds” approach of DeBeers, your chemical advertising campaign can appeal to the need to be smart and to look smart.  The way to make a buyer look smart is to offer a service that gives competitive pricing and timely delivery of quality goods.  Buyers always have a list of difficult-to-find materials as well, so advertising unique reagents and intermediates is often worthwhile.