Category Archives: Chemical Industry

Specification Creep

Back in grad school, when I was a younger and more innocent chemist, I never gave the matter of purity specifications much thought. Well, let me qualify that.  If my Aldrich reagent was 98 % or greater, I was usually happy.  Yeah, there is the matter of water and a few other things, but for the most part specs didn’t pop into my radar very much.  The other cats and dogs in the material usually washed out somewhere along the reaction sequence.

The issue of specifications in the fabulous world of industry, however, is a really big deal. Indeed, for a company that does custom synthesis or is otherwise agreeable to starting up production of a new product, the matter of negotiating specifications is strangely complex.  Customers have expectations of how pure their product should be and the manufacturer, that is, those who are grounded in the bitter reality of chemical processing, may be far less certain as to what constitutes a reasonable specification. This is nothing new or secret.  All other manufacturing industries have the same issue. 

I previously said that the matter was strangely complex.  Before the customer and the manufacturer can agree on a deal, they have to resolve the matter of what is needed vs what is wanted

Here is a case study: the customer initially specifies 99.0 % purity, white crystalline solid, and no greater than 0.2 % residual solvent. And they want it for $100/kg for a metric ton.  Fine, you say, it’s a hundred kilobucks worth of business. We’ll go in the lab and front run a process. This way we’ll be able to give the customer a qualification sample, and just as importantly, get an idea of the process economics.

The chemist does a representative front run and reports the following.  The process produces 68 % isolated yield of off-white powdered solid that has clumps, 1H-NMR shows that it is 98.3 % pure and it has 0.5 % residual solvent.  The product is a first crop and the solvent is a high boiler like toluene. Analysis of the mother liquor shows that there is an additional 21 % of product remaining with the balance of the mass as unidentified colored components. 

This is a node in the decision process for the manufacturer.  From this result, we have to make a business case to go forward or decline and offer a “No Quote”.

The customer has expressed a preference for a pricing set point of $100 per kg for a metric ton.  It is hard to know if this price and volume are just posturing or if they are firm numbers.  More often than not, the customer will decline to disclose an upper price limit.  Remember, the buyer’s job is to get the lowest price and the sellers job is to get the highest profit.  It is common for a buyer to ask for a quote on a volume higher than they intend to order just to see where the price/volume curve flattens.

The first thing to notice is that the first crop fails to meet the specifications all around. Low purity, high residual solvent, off color, and clumps of powdery material instead of free flowing crystalline product. A estimate of the cost of manufacture suggests that the raw material cost is about $38 per kg and the labor and overhead cost is $52 per kg. The first pass doesn’t look good- estimated costs are ~$90/kg for off spec stuff.  Irrespective of the product’s compliance with the spec, if your sample is truly representative it might be worth sending a sample to the customer anyway.  You never know. The customer may recoil in horror or find that it works in their process despite being “off-spec”. 

It is at this point that the sales or business development manager has to make a decision- Are there any insurmountable problems with the front run?  If not, we have to decide if we want to risk R&D time to do process development to tweak the process to give product that meets the spec.  Remember, time = money.

The good news is that the purity is only slightly low, the residual solvent can be pumped down in a vacuum oven, and the clumps can be sieved out. But remember, too much “polishing” will tend to increase labor costs per kg of product. 

The color appearance is another matter.  It might be resolvable within the customers price constraint, or not. The transition from off-white to just white can be a difficult change. Whiteness is surprisingly subjective and dependent on particle size. And, particle sizing can involve a lot of art.  If the product were a $100,000 per kg pharmaceutical, there would be much more motivation to get the color right. Remember, it is only a $100,000 sale. One could easily burn up all of the profit in an prolonged period of process development and pilot plant time before you even sell the first kilogram. 

Product appearance would be a good candidate for negotiations with the customer. Try to get them to give up white for “white to off-white”.

The price is another problem.  It is too low.  It is desirable to have 20 % profit after interest and taxes, just like the pharmaceutical folks report.  A good rule of thumb is that the total manufacturing cost should be approximately 50 % of the price or less.  This is highly variable and subject to the company’s accounting practices.  So, just for arguments sake, let’s say that we need to get the price to equal twice the cost. 

To come in with a reasonable profit, we have to get the manufacturing cost down to $50 per kg.  The raw material costs were calculated at $38 per kg. Raw material costs are the least flexible, so that leaves little room for labor costs at a targeted $50/kg mfg cost.  The good news is that the labor costs are higher than the raw material costs, so at least there is some hope for bringing the total cost in line.  Labor costs can be brought down with processing experience and innovation. The learning curve is real and good plant manager can bring labor costs down over the product lifetime. 

In this circumstance, I would vote that we go forward with the product if we can initially keep the mfg costs at 65 % of the price or lower.  I would also vote that we send a representative sample to the customer for evaluation. In the mean time, we can do a bit of R&D to find a better process. 

Finally, one of the business risks for a manufacturer is the issue of “specification creep”.  Initially, a manufacturer will agree to produce a new product with a particular set of specifications. However, if the customer is simultaneously developing their use of this chemical in their new product while you are developing this chemical process, a gap in specifications might occur.  In other words, the customer might begin to tweak the product specs while you are in the middle of process development. 

The customer will call one day and try to add a specification. They will find that a previously obscure side product will present a big problem for them and they’ll indicate that the project will require higher purity.  Well, this might be a big problem, or not.  If it requires a tighter fractional distillation, assuming you can do it, this will probably add labor costs. If it requires further decolorization or reduction of residual solvent, R&D will be required to validate the changes to your process.  It is actually a big deal.

So, why not just say “NO”?  Well, in all likelihood, you have not been paid yet.  Few customers will pay for development in advance. Those costs have to come out of future sales.  It is a lot like boiling the frog. You just ramp up the temperature imperceptably and the frog never notices that he is being cooked.  The same effect can happen with specification creep.  By being willing to work with the customer you’ll find that at some point it becomes too costly to go forward at the arranged price. 

At this point you have arrived at the hardest part of doing business- the part where you have to say NO to a customer.  Some people can’t do it. Honestly. But if you want to survive, you have to set boundaries. The customer will understand.  This is where good communication skills come in. It is always desirable to give bad new earlier than later.

NaBH4 Reduction of Esters

What new things are there to say about sodium borohydride?  Very little, really.  I have to say that I was generally unaware that NaBH4 had utility in the reduction of esters.  The Gray Beast or Lucifer’s Hydride- LiAlH4- has always been the reagent of choice for carboxylates.  But while enroute to other applications of NaBH4, I stumbled upon a few recent references.  This is why I like to browse.

A 2006 article by de Souza in ARKIVOC, reports that aliphatic and aromatic esters are cleanly and rapidly reduced by NaBH4 in methanol/THF.  OK, that’s nice (yawn). Other references to ester reduction can be found dating back at least to Persterfield in 1965 and references therein to 1961.  It’s obviously not new, but I do think that it is relatively obscure.

Reduction of benzylic ketones and alcohols as well as assorted amides in acidc media to form the corresponding -CH2- or N-alkylation product was reviewed by Gribble at Dartmouth in 1998. 

Well, here is the reason for my excitement.  I did some pricing and found that the $/hydride cost of NaBH4 is approximately 25 % that of LiAlH4 at the bulk scale.  That’s a big deal.  What is a bigger deal is that NaBH4 is arguably safer to use than LAH and you can run reactions in water, MeOH, and various combinations of other solvents.  Kill the excess hydride with aq NH4Cl and you’re off to the races.  Though I dearly love and respect LAH, handling bulk material as the solid or as an Et2O or THF soln brings unfortunate hazards to the plant. And, LAH quench can lead to large volumes of pasty aluminate solids that present serious filtration issues. 

I’m sure that a lot of hot shots out there knew this, but it was new to me.  The great breadth of reactivity of NaBH4 as well as its stability to protic solvents provides many useful possibilities for the process chemist. The ability to run a reaction in methanol as opposed to anhydrous ether or THF can provide cost, safety, and competitive advantages for a manufacturer.

1/25/09. Update. US patent 2,765,346 teaches a process wherein Na or K BH4 in THF is treated with LiCl to form a composition that reportedly reduces a variety of esters to the corresponding alcohols. Examples of selective ester reduction are ethyl benzoate, butyl stearate, and ethyl p-nitrobenzoate. While I have not personally tested this process, it seems plausible enought to try.

Hu- The Human Element

We’ve all seen the ad on television with it’s folksy music and mosaic of compelling images while the voice-over waxes philosophic about the “Human Element”. It is a very well done piece of public relations art.  The theme is that the practice of chemistry is ultimately about serving people.  I’m inclined to agree, though the ad does gloss over the imbalance between service to the stakeholders and the shareholders.  But that is the general state of affairs with the whole of the corporate world.  We’re all stakeholders, but only a few are actual shareholders.

Few people outside our field associate chemistry with the term “high technology”.  That is commonly reserved for medicine, electronics, and aerospace.  Just look at any news outlet or magazine. If it ain’t happenin’ in space or in the hospital or it doesn’t involve TV or cell phones, it is too boring for words. 

But in fact, chemistry deserves to be in that elite group as well.  We chemists know that the ballyhoo about advances in medicine typically resolve to advances in the chemical sciences.  It’s the same for electronics and even aerospace because they rely heavily on the material sciences. OK, so our chosen field is not the object of admiration. We’re probably better off for it.

It is an understatement to say that the human element is important.  My observation is that resolving issues with the other elements is almost always easier than issues relating to this one element- Hu.  Using it to titrate buy-in, cooperation, or just help often requires the most subtle interactions and the results can be spectacularly non-linear. 

Sometimes Hu is refractory, other times it is pyrophoric.  It can be most agreeable, or not.  I still do not understand it very well.  But I’ll keep trying. 

Chemical Business Development People

Any chemical manufacturing business has a sales group.  Sales people will sell existing products, that is, products for which the manufacturing facility already has a process.  It is relatively straightforward to sell existing products.

If your company is so disposed, the sales group might also market its ability to take on new projects.  To sell this kind of capability you need a special kind of sales person.  Many companies call such sales people “Business Development” managers. Such people almost always have a strong technical background and a desire to interact with customers. 

A business development manager is a special kind of animal.  In addition to their technical ability they must have a wide range of general business skills.  Such a person must have a thorough grasp of all phases of manufacturing- R&D, pilot plant, semi-works, and production.  This intimate understanding of manufacturing is not limited to just the technical aspects of making a proposed material to specifications.  There is raw material sourcing to be done as well as the generation of an economic model of the proposed process.  And, before you can even offer a product you have to do your due diligence in the intellectual property arena. 

The business development person must somehow mesh the customers price and delivery requirements with the company production timeline. For the development of a new product,  a company needs a process that operates at scale.  To get a scaled-up process, it has to have a process validated at the pilot plant scale.  To get a pilot scale process, the company needs its process bench chemists to pony up a process that is cost efficient and safe. 

The practice of business development will involve math.  Costing and pricing are two economic activities that will put you in contact with accounting and with upper management.  This is where the job can become highly stressful.  Your company will probably have costing numbers that are reasonably accurate.  I say probably because there is some philosophy involved. 

Your accountants will use GAAP- Generally Accepted Accounting Principles.  I’m not an accountant and I have no aspirations to be one.  All I can say is that the allocation of costs to a given product, at least in a multipurpose facility, will involve some assumptions about how to partition resource costs to any given process.  The previous sentence can be the source of incredible confusion for companies.  The method by which costs are allocated can lead to numbers that are unrealistic on either the high or low side.  Overly low numbers can lead to pricing that is too low to sustain the operation.  Overly high numbers can lead you to offer quotations that are not competitive. Both circumstances are not desirable.

A business development person must be intimately familiar with all phases of manufacture.  Fundamentally, business development people are show horses.  They represent their company on site and at meetings and conferences off-site.  A business development person must have excellent communication skills, be an effective public speaker, and be in command of details in diverse fields.  And, it really helps if you have some savoir-faire.   Personal skills like the ability to listen, to carefully drill into customers and competitors for specific details without being rude or creepy.  It helps to be able to dress well, understand decorum, and display good manners.  It is better to be sincere and risk being taken advantage of on occasion than be cagey and deceptive. This kind of thing does really matter. 

Many chemists out there who have yet to hatch from the academic and post-doc world may not have heard of this job description. Other manufacturing arenas may use engineers in this capacity. In the chemical manufacturing field, chemists can step into this type of activity and be in the center of the activity and at the edge of technology all at once. Having done it, I can only encourage fellow chemists to consider it as a career path. 

Isotope Mojo Blues

Near as I can tell, there is some kind of demand in the marketplace for all of the elements from 1 through 92, with the exceptions of Pm, At, and Rn, I suppose. It is hard to gauge the trade in actinides since precious little gets outside the realm of government regulatory frameworks. Clearly there is demand for certain isotopes of Th, U, and Pu.  But the nuclear regulatory people keep a tight reign on that stuff.

I remember a pottery class I took some years back in a nearby town. I was snooping through the pottery stockroom looking for glazes and what did I find? I found a sizeable quantity of Thorium nitrate.  These hapless middle-aged, post-hippy era, meadow muffin starving artisans running the co-op clearly had no idea that they had an actinide a nuclear-age artifact in their midst. Obviously, it had been secured for colored glaze applications.  I warned them about it but was met with the cow-in-the-headlights-look. I call it the “bovine stare”.  So, I brought a GM survey meter the next week and opened up the jar with a few of them standing there. As the clicks ramped up from the beta’s and as I switched the attenuation to keep the needle on scale, I thought I heard the unmistakeable faint slapping sound of multiple sphincters slamming shut.

The first question was “Would I like to have it?”.  Pppffffttttt!  “Hell no!” says I.  Nuclear cooties. Jesus H. Crimony!!  I did a careful survey with the GM counter and found that the surrounding area was clean. The material (early 1960’s vintage by the looks of the label) had hardly been used, so I was confident that contamination was not too bad, if indeed there was any. There may have been alpha emitters but this counter wouldn’t pick them up.  I gave some names of hazardous waste vendors and a stern warning not to drop it or spill it.  That’s the last I heard of it.

I remember a seminar in grad school when a visiting rock star from ETH gave an organic seminar detailing the use of Li-6 in NMR studies.  The fellow lamented in his fastidious German/Swiss accent that it was difficult to get Li-6.  He also said that for a time much of the refined Lithium in the market place was depleted of Li-6.  It would be interesting to hear someone comment on the accuracy of this. 

Bloggenvolk- ACS Chicago Meeting Minus Gaussling

Sadly, regrettably, and with heavy heart Th’ Gaussling must disclose that he was asked to cancel his trip to the ACS meeting in Chicago. The clarion call of duty has sounded for all hands on deck.  Mister midshipman Gaussling will take heed and report to battle stations.  Ours is not to wonder why.

It is probably a good thing. I always spend way too much money on books at these meetings anyway.   There is always the Gordon Conference ….

Perhaps other bloggenvolk can meet in Chicago.  I think it is important for people to socialize.

Cash is King

It is tough being a small company or start-up.  You have perpetual cash flow concerns and maintaining a big enough plug of working capital is always difficult. Add to this the fact that larger companies tend not to take you seriously on either the buy or sell side. 

Selling to a company that is much larger is often challenging.  They are often skeptical of your ability to deliver; they want to throw their weight around by dumping outrageous terms and conditions on the table; and they may want you to “invest in the relationship” with freebies like holding inventory, unpaid R&D, free R&D samples, or a dozen other things. 

One of the common purchasing tricks is to ask for wide range of volume pricing. That is, ask for the pricing of 1, 10, 100, and 1000 kg of a product.  What they will do is to look at the largest volume price as a sort of floor or asymptote price and then begin to ask for lower quantities at that price.  They know that you can offer the material at the low unit price one way or another, so why not ask for smaller quantities there as well?  This can be a very effective leverage when negotiating price with a vendor, that is, the knowledge of their fall-back pricing. 

As the manufacturer you are well aware that the economy of scale only works if you actually manufacture at scale.  Many manufacturers of specialty chemicals may not actually keep certain products in inventory. If their sales history is spotty or if it is relatively obscure, there is no way to predict demand.  So, dumping capital into finished goods that sell poorly is a bad decision most of the time.  When you do not carry a product in inventory, that is, you only make it on demand, your hands are tied in price negotiations.  You just can’t rationally offer 10 kg at 1000 kg pricing.

Another difficulty is invoicing.  It is almost always the case that the vendor will have to pay for raw material in advance, hopefully with commercial credit terms like 30 days net.  And no matter what, payroll has to be met.  So the manufacturer has to commit resources up front for a given sale. Only when the product goes on the truck can the vendor issue an invoice.  This is all reasonable and expected.

It is possible to go to your banker with a purchase order in hand and apply for a short term loan to fund the manufacturing costs.  It is important to get to know your banker well. If they have confidence in you they can help you out during tough times.

Typically, payment is due 30 days after the product ships.  Some companies will insist on starting the clock when the shipment arrives. For shipments in the states, this isn’t such a problem. But for shipments involving boats it can present cash flow problems given the month-long transit time.  Incidentally, companies that use the SAP accounting system will have requirements that will be as fixed and unchangeable as the very ground you stand on. 

It will usually transpire that the manufacturer will have to pay for raw materials and payroll well in advance of payment.  This is normal.  One of the ways you get into trouble is when raw mats show up too early or too late. Raw mats that show up too early will require payment sooner and raw mats that show up too late will delay manufacture.  Timing is important. 

Another kind of financial trouble you can encounter is from late payment or even nonpayment from a customer. Late payment gives rise to all kinds of trouble for any company, but especially for small, capital-deficient companies.  Receivables accountants maintain an aging chart for invoices.  After 30 days, the receivables person will begin to get nervous and get on the phone to roust the customer for payment. After 60 days, people are getting jumpy about payment and after 90 days there may be calls to the customers president or controller. 

When a company has a cash flow problem, they will direct whatever cash they have into their most critical expenses in order to keep the place running.  Your invoice may not be at the top of the list.  When you encounter this problem with a customer, it is important to keep your cool and try to get whatever they can afford to send. Chances are good that they are already twittered about it so threats and heavy handedness may be a waste of time.  But often it is the squeaky wheel that gets the grease (or lucre) in these circumstances. So it is always worth talking to the customer about payment.

This whole business of pricing, invoicing, and getting paid is deadly serious and the inability to do it well will shut a company down quickly.  We technical people often discount the accounting end of our business, perhaps believing that it is the domain of lesser skilled persons.  Successful companies, however, know that a good accounting group and clear policies are crucial for stable operation.

Start-up companies, however, may not pour resources into accounting systems as generously as they should.  Often, it is the founders who do the accounting themselves in the early days.  Eventually, the founders realize that they need book keepers and accountants to manage all of the cash flow issues.

Purchasing- The Dark Side of Business

All sales people have to deal with purchasing people in some way or other.  In the B2B chemical business, where you never really meet the ultimate end user, sales people can be found to populate two levels.  Non-technical and technical.  Non-technical sales people are, in my experience, relatively scarce in the chemical field.  Yes, you do find people with degrees in business doing chemical sales, but without any technical savvy they are at a distinct disadvantage.  Most of the people in chemical sales tend to be technical types of one stripe or another- engineers, technicians, or chemists.

What has always struck me about business is the dramatic differences in culture and operating policies between companies in a given market.  Some companies make it nearly impossible for sales people to contact employees and other companies seem indifferent.  I have noticed that pharma companies are particularly stringent about employees meeting with sales people.  Of course, this may just be an artifact of my sampling experience.

There is a reason, of course, for a company to make it difficult for sales people to contact its staff.  They want their purchasing “professionals” to be present and/or in control during such encounters.  This is not unreasonable.  Some large pharma houses for instance have contracted other companies to do their purchasing for them.  This being the case, uncontained or off-line purchasing may be redundant, uneconomical, or a breach of contract. 

But the other reason for discouraging staff from meeting with sales people is this- purchasing people are skilled in the art of procurement.  They are familiar with company policies regarding suppliers and negotiation.  And, not insignificantly, they tend to be a bit more refractory to the enchanting ways of sales folk. 

A well run purchasing department is a type of profit center.  Not only are they required to get the cheapest and most stable supplier, but they are also tasked with extracting other concessions as well. Other concessions may include custom shipping & packaging details; custom specifications; an agreement to maintain inventory; special price/volume arrangements; or long term pricing agreements. A good purchasing manager is worth their weight in gold.  Over their career a good procurement staff can save a company vast sums of money and secure strateginc reserves of raw materials for competitive advantage. 

I joke about purchasing as the “dark side” because a good purchasing person can be a really tough sell.  They make sales people work hard for their money but in the end everyone is better off because it makes businesses more resilient and competitive.  They raise the bar and, painful as it may be, in the end we all benefit from excellence in business.

Whereupon Gaussling spoke in allegory

After a deep but unrestful slumber, I awoke to find myself in a dark wood. I cannot account for exactly how I came to be in this gloomy place. It is a hard thing to grasp even now.  As I look back to that dark encampment, my heart quickens at the knowledge of what is to follow.  

After many hours of climbing through the dense thicket, I chanced upon a path that lead through the gloom to a valley whose hilltops glistened in the morning sunlight.  As I trod over a small hillock to the opening of the valley, I spotted a jackal some distance ahead in the path before me.  I stopped to rest for a while and ponder the situation. As I rested, the fearful animal disappeared into the tall grass of the glade.  Having lost some of my weariness, I again took to the sinuous path in the direction of the now rising sun.

The day wore on and the shadows retreated to their origin under the noonday sun. I began to notice large, flat field stones along the path.  As I continued my journey, they became greater in number and were festooned with a great many lichen encrusted runes. The stones were partially buried and had evidently been organized at some time in the distant past.  I am familiar with many styles of writing and symbols, but these marks were decidedly odd. Not only were they unfamiliar, but they were chisled by a hand accustomed to a wholly different way of using language.  I found one particularly large stone with a great many markings on it.  As I looked at the marks, I stepped around it to view the runes from different directions, trying to ascertain some form of structure and syntax.

What could these stones represent? After some time, I began to note that certain markings were found elsewhere, though in different combinations. Perhaps through inattention I wandered from the path for some distance into the glade.  Finally, shaken from the enchantment of these stones I tried to regain my bearings. I struck off in the direction of a nearby col in the mountains, hoping to intercept the path by sundown. 

As I broke a trail through the high grass a moving shape caught my attention.  It was on the left side of my view and may have only been a bird taking flight from a shrub. I had nearly forgotten about the curious animal I spotted earlier in the day, so the movement startled me.  Was it a shy visitor or a predator? Trying to take my mind off this unpleasant topic, my mind returned to the runes. What could they be saying?

[With apologies to Dante Alighieri- Th’ Gaussling]

Bloggenvolk Chicago ACS Meeting

A group photo at the Chicago ACS meeting.  That would be fun and blessedly easy.  If bloggenvolk want to linger and talk, they could do that. (If you haven’t been to the Art Institute, I heartily advise a visit.)  It’ll be Chicago in March, so that means outdoors may be nasty.  We just need someone to shoot the photo and post it somewhere on the web. 

What about monday noon, at the convention center, in the entrance near that rotating product literature carosel they always have? Any takers?? C’mon.  Be a sport! I’ll be wearing a badge that says “Gaussling”.