Category Archives: Chemical Industry

Getting product out the door

Manufacturing is all about getting product onto a truck and watching it leave the gates of the plant. Because after the shipping documents are given to the driver, the invoicing begins.  This is a very time sensitive action.  The customer can’t pay until the invoice is received and the 30-days-net countdown begins.

It is deeply satisfying to package a chemical product that you have prepared with your hands and your wits.  I find the act of packaging product after it has passed QA appproval to be my favorite part of the process. It also means that I can start something new.  Rarely does one hear anything from the customer if the product is satisfactory.  The only time you hear from the customer is when something has gone wrong.

The bean counters will render the process into some bland abstraction that has inputs and outputs. They’ll yammer on about ROI and earnings before taxes, interest, and … whatever.  I’m glad to see that the MBA’s learn something in business school besides how to manage their IRA’s. But there is more to business than the electronic transfer of funds.

What really matters to me is that I did something useful this day. It matters that my hand-made product is useful to someone else and performs as required. Making things and stuff contributes to the ongoing process of civilization.  I feel sorry for the pure finance people.  They don’t know the satisfaction of isolating a water-white product in 99 % purity and slapping a label on the bottle and giving it to the shipping folks. I still get a  kick out of it.

Carbonylated Surf and Turf

As a desperate strategy to fight insomnia, Th’ Gaussling often finds himself watching C-Span at 1 AM.  Congressional testimony or a televised speech at the International Museum Docent Convention by the Acting Assistant Deputy Undersecretary of the Stratosphere is often enough to initiate somnolence.

But early this morning was different. A panel of FDA administrators were before a House Committee on Commerce Chaired by Rep. Bart Stupak, D-Michigan. At issue was H.R. 4167, the National Uniformity for Food Act. Apparently, the proposed law will remove requirements for certain kinds of food labeling, in particular the presence of certain additives may not be part of manditory labeling.

What has come to light is the industrial practice of exposing meats and fish to an atmosphere of dilute carbon monoxide (CO, ca 0.4 %) in order to maintain a red color in the flesh.  Meat naturally turns brown on exposure to air over a short period. Industry has been wrestling with this for a long time, adopting and subsequently abandoning various schemes for maintaining the reassuring red color of meats and certain fish. Carbon monoxide coordinates with iron in haemoglobin to afford a complex that renders the tissues red in color. The FDA defines CO as a fixative in this application, rather than a preservative.

As a result of the use of this scheme, it is possible to keep meats and fish with a saleable red appearance for much longer. This reduces store losses due to the non-marketability of brown meat.

The House Commerce Committee was split down the isle in terms of its concern for this matter. Democratic committee members voiced considerable concern over the subterfuge of artificially reddening meat, allowing unwary consumers to falsely conclude that the meat could be fresher than it really is. Republican members seemed disinterested in the matter and several voiced concern that the FDA should spend it’s time with Salmonella rather than CO. The honorable Republican member from Kentucky tried to suggest that as a “simple country doctor”, he was having trouble understanding the issues and pronouncing the words (Rep. Elmer T. Bonehead, R-KY).

Whereas many of the members soft pedaled their questions, Rep. John Dingell, D-Michigan, offered no quarter to the FDA group. In particular he focused his attention of Director of Food Additive Safety, Laura Tarantino.  In earlier testimony, Tarantino was a picture of confidence. Her knowledge of the statutes and the Byzantine procedural details as well as her confidence and instant recall was impressive. However, when Dingell’s time for questions came along, he went after her with rapid fire questions, not allowing time for her to qualify her answers or fend off subtext.  “Just answer the question, yes or no”. It was interesting to see.  Dingell was obviously disgusted with the FDA.  The regulations and protocols that govern FDA movement are very complex and apparently even the administrators have faint grasp on much of it.

Director Tarantino stated that no specific rule-making concerning CO fixatives had been completed because it was still under study.  The working assumption was that CO was considered GRAS- Generally Recognized as Safe. These assumptions are often advanced by industry and accepted with scant examination by FDA.

When asked about the general safety of CO in the product, one FDA manager stated that the added CO posed no hazard. I have no reason to doubt this. But the real issue is consumer deception. I think even libertarians would have to agree that without disclosure of food additives, the market cannot rationally award its demand to preferred providers. You can bank on the notion that consumers are particular about meat and freshness. HR 4167 is a step backwards for consumers and we can only hope that good sense prevails in the House.

Evonik Absorbs Degussa

Another venerable corporate identity has been rendered obsolete.  Evonik Industries AG has acquired Degussa to form what they call the Chemicals Business Area. Evonik has interest in energy and real estate as well.

It always surprises me to see a buyout that includes the retirement of an entire corporate identity. It’s the same with Union Carbide or Hoechst AG (now Aventis). There is so much name recognition with company’s like this that I really wonder what the rationale is for the change.

I recall one evening at a bar in Houston we were drinking with some Degussa business develpment guys after a tedious day at a conference. After listening to these German guys griping about American drivers, I took a sip of my gin and tonic and asked the question-

“So, was there a founder named Herr Degussa somewhere, sometime in the past?” They looked at me for a moment and then began to laugh. Turns out that the word Degussa  comes from “Deutsch Gold and Silver” in some fashion.  Or, so they said.

Best wishes to the good folks at (former) Degussa in their new adventure.

Management Recruiter Buggery

High on the list of exciting professional experiences is the job interview process.  I just spent the weekend updating my resume. It is good to do this now and then if for no other reason than it forces you to recall just what the hell you’re good for.  As I performed this task, I was flooded with a stream of memories, both good and bad. 

I’ve had great interviews, ho-hum interviews, and a few awful experiences. My greatest interviews were from my stint in academia. Of the 7 interviews, I received 5 offers.  Not bad for a rythmically disabled Iowegian. But a few years later my smug confidence was to be shaken by an whole body dose of reality.

Academia is not reality, it is a sort of intellectual Hollywood. A la la land of frog princes and preening fussbudgets, special effects and make-believe. It is a pageant of grant-writing rock stars and untenured showboats on parade waving their tail feathers at all who would watch. I who had earlier embraced that world would later be out in the catabatic winds of big time management recruiting.

I won’t write a tedious valentine about my slender portfolio of actual talent.  Instead, I’ll tell of an experience with those bottom feeders of the job world- recruiters. 

In the frantic world of job placement, there are several kinds of recruiters. There are the recruiters that place at the highest levels of play, and there is everyone else. In my view they are all shady operators.  They will drop a line with bait on the end right in front of your face. Poachers they are. They’ll feign an excuse to call you at your office and query for associates –wink wink, nod nod- who may be looking for other work.

You’ll send a resume and there will be some back and forth. The recruiter will get to know you a bit.  Then one day you’ll receive an email invitation to interview at their office suite in Watercloset, PA.  You’ll fly to Philly, the city of brotherly shove, and navigate your rental car to their office.  The waiting room will have that dental office smell that’ll make your flesh crawl and your molars throb.

A smarmy receptionist will hand you off to a smarmy executive recruiting specialist. For me, this is where it all went down the toilet.  I sat in an expensive office near the Delaware River while the recruiter reviewed my resume, my buttocks reflexively clenched in the way countless other buttocks have been so clenched in that leather chair while enduring the first 2 hours of detailed questioning- “drilling in” they call it.  All the while, she was quietly building a case for yea or nay.

Here is where I went wrong. It was utterly and comically naive.  I thought that the recruiters job was to get me an interview for a management slot with an international chemical company. Fancy that! As I was to learn, my assumption was wildly and insanely in error. The recruiters, you see, only get paid when they deliver a candidate who gets hired.  So, they prescreen over the telephone and only bring in final candidates for the slot.  I was a final candidate for Sales and Marketing Director, but that is still far from the finish line.

As I sat through the meeting, it dawned on me that I was not being coached to give an award winning interview with the unseen client, but rather, I was being slowly skinned alive. 

Based on earlier conversations with this recruiter, I thought that they would deliver me to an interview with the company looking to fill the position. Instead, I was brought into the recruiters office for a much closer inspection on behalf of the customer. I was to have my professional colon inspected, so to speak, by these savage HR mercenaries.

After the early morning session with the contact recruiter, a real heavyweight was brought in- a partner of the firm. He was apparently an alumnus of HR at Merck and was accustomed to body slams in Big Pharma. He was a sort of “Refrigerator Perry” in the recruiting world.  There were no pleasantries, only an immediate start to some pretty rough play.  There was a long succession of close and bluntly skeptical questions about my experience and abilities. The two recruiters did a bit of good cop, bad cop along the way.  They were a team and played a disciplined game of question and answer, drilling ever deeper to what they were looking for.  The refrigerator lectured me at length like I was some kind of rube from up the holler, giving me the facts of life in Big Business. 

I guess I really was a rube from up the holler.

It didn’t take very long for me to see that not only would I not advance forward in this game, but I would have my head lopped off and handed to me on a greasy wooden plate.  And that is what happened.  After 90 minutes of questions and thinly veiled accusations of weakness, inexperience, and retarded professional development, the Refrigerator stood up and left the room. As the other recruiter fumbled with her notes, I sat there in silence like a stunned carp floating on the lake surface after dynamite fishing. After a moment she suddenly became matronly and bleated out consolation.  I was stunned and shocked from the rapid fire rude questions and the careless dissection of my very being. I had never been treated in this manner before, not even in grad school.

After my “case” recruiter made a brief show of effort to salve the wounds, I put my severed head under my arm and was shown the door. It was a long, depressing trip back home. I have had plenty of time to mull it over and can only conclude that I was treated badly.  As for the chemical company, I have had the chance to shun them as a supplier in subsequent years.  My indulgence in pettiness is one more scar from the experience.

Possible Signs of a Slowdown

Hmmm. Some early indications of a slowdown are out there in certain commodity markets.  Purchasing people getting conservative and skittish with forecasts. When buyers revise their projections downward or say that they’ll ride on their inventory for a while longer, you can bet that rougher sledding is ahead. Just a question of magnitude.

The signs come a day after Bernanke suggested that a slowdown was possible. Cause? Effect? Hard to say.

The picture will begin to resolve over the next few months. The first quarter of the year often sets the pace for the year in markets that I’m familiar with. The chemical manufacturing market is so global and the dollar is so low that it is hard to determine if some of the latest conservative buying behavior is an actual indicator or not of business slowdown.  Hmmm. 

Toward the Green Manufacturing Ideal

In the waters that I swim within, the term “Green Chemistry” is often derided as an environmental extremist codeword used by chemical technology Luddites. I’m sure there are anti-chemical purists who view Green Chemistry as a kind of natural alternative to the use of man-made, unnatural substances. Biodiesel is is commonly held as one example of a green alternative.

The merits of Green vs non-Green, or the inherent Greenness of Green technology is a contraversy too large for this blog. Instead, I would rather turn my attention to the merits of Green thinking in chemical process development.

Specialty chemical manufacture begins with relatively simple raw materials and produces more complex and more valuable compounds.  Limiting the topic to synthesis as opposed to formulation, specialty chemical manufacture relies on the application of functional group manipulation to achieve an end product with the desired features and connectivity. 

In chemical manufacture, there are several general ways to improve process economics. The most general term is process intensification, which describes the overall effect of maximizing the conversion of raw materials into product per volume or per dollar of capital equipment.  This can be done by a) running reactions at more concentrated levels, b) the application of heat and pressure, c) the elimination of solvents altogether, d) the use of more reactive species, or e) telescoping. 

a) Of the many kinds of reaction optimization schemes that we learn in grad school, perhaps the least explored is space yield improvement. Space yield is just the kg of product obtained per liter of reaction mixture used.  In manufacturing, the goal is to maximize the number of kg of product obtained per plant man-hour for a given piece of equipment.  Raw material costs are only slightly adjustable, whereas labor hours can often be lowered with the application of better technology. Labor costs are among the highest costs in a plant, so the goal is to produce the most kg of product per man-hour.  

Intensification by increasing space yield simply means that a solution reaction is run at the highest reasonable concentration. The benefit is that a reactor is run at the highest mass yield per batch.  Since the corresponding increase in labor to run the higher space yield is near zero, the resulting labor costs are spread over a greater quantity of mass- the labor $/kg go down.

b) Most people come out of college with precious little experience or appreciation for the benefits of high temperature and pressure in chemical synthesis. Continuous high temperature short time (HTST) reactions are out there, but require specialized equipment and expertise. Engineers love this kind of processing. For an optimized process, HTST systems have comparitively small reaction zones that are relatively inexpensive and take advantage of the economics of continuous flow chemistry. Good examples are ammonia production or Petroleum refining.

c) The elimination of solvents is a tricky thing. Gas phase chemistry is well known and quite mature technology. It is also amenable to continuous flow processing.  Elimination of solvents in condensed phase chemistry is a bit different problem.  Solvent molecules are like tiny sand bags in their ability to absorb energy.  Neat reactions may be prone to exotherms, so the calorimetry of any given proposed neat reaction needs to be examined carefully.

On the plus side of solventless processing, the space yields are at maximum and reaction rates are not diminished by dilution effects.

d)  The use of more reactive materials in a process can have benefits in time savings if a particular step is slow or does not go to completion. If the reactive reagent affects the rate limiting step, then time and yield savings may be had. On the down side, increased reactivity may offer decreased selectivity. Increased hazards will have to be calculated into the value proposition as well.

e) Telescoping refers to the combination of multiple steps in one reactor.  In it’s best incarnation, telescoping may afford the direct reaction of a product in the reaction mixture of the previous reaction. The benefit is in the savings of man-hours in vessel cleanout and preparation time, minimized hazwaste, and minimum handling.  Another form of telescoping would be that pot residues are left in the vessel and reagents from the next step are charged in without extra transfers and new vessels.  This tends to minimize the number of vessels needed for a process and minimizes the opportunity costs of having empty vessels standing by for use.

The goal of green chemistry as I see it is to minimize environmental insult by the reduction of consumables and the discharge of hazardous waste streams from a plant to the outside world of waste treatment.  The reduction of consumables like solvents, reagents, or electrical power reduces hazards and pollution up and down the value chain. The reduction of hazardous wastes minimizes the mass that has to be consolidated for eventual incineration or burial.

The reduction of consumables is entirely compatible with the economic goals of business.  Process intensification points to the same general direction as the goals of Green Chemistry and should be considered a type of Green activity.  If one draws a picture of the ideal state of any chemical manufacturing process, it surely would include intensification with sustainable raw materials and with maximized throughput and minimized risk.

Japanese Trading Companies

Selling goods to Asia can be challenging for westerners. End users of chemicals in Asia often use trading companies to do their buying.  Selling to an Asian consumer of chemicals via the usual tools of marketing- cold calls, advertising, etc.- is complicated by the fact that the buyer may not be the end user. A call to an end user, if you can find their identity, may be politely declined. Instead, you might be referred to the allied trading company or just shown the door.

Th’ Gaussling is not an expert in this area of business. But I have more than a passing interest. Under the egg on my face are plenty of black and blue marks from my latest lesson. I should be receiving a certificate for 2 credit hours from the correspondence school of hard knocks.

Outwardly, chemical trading companies often look like end-users of chemical products. If you visit their websites, they’ll promote the manufacturing capacity of their customers and the impressive list of fine chemical products. In reality, they are located in a cramped office suite with fax machines and a server that projects the image onto the internet.  Their activity is limited to buying, selling and arranging logistics. Trading companies are part of the social custom of strategic alliances in Japanese business. They may buy and resell with a markup. They may provide contract buying services. There are numerous ways to do the deed.

For a factory, this arrangement allows managers to focus on manufacturing. Since trading companies only get paid if they hand over their deliverables, there is always a productive stress on the procurement people to look after their cadre of customers. 

One big problem from the vendors perspective is negotiation.  Negotiating with an end-user through an intermediary trading company is complex and time consuming. It’s best to do this face to face. Negotiation over the internet is not the best method. Trust is an issue and one gains trust by direct meetings.

The discussion of technical issues may also proceed through the trading company. This is can be a nightmare. I have wasted far too many precious heartbeats trying to noodle information from the end user through the mouthpiece of the trader. But from their side, this amounts to providing needed service to the customer.

It is difficult for western suppliers to penetrate the mind of customers in the east and discover how to market their wares in that part of the world. The trick for western business development people is to invest time and effort in understanding Asian trading practices.  Pick up some books on the topic. Go to trade shows and talk to Asian exhibitors. Read the trade publications.  Develop personal relationships.  Price wins the day, but trust is part of the calculation.

The Scariest Stuff- Pu and Phosgene

Has anyone else noticed how people behave when they describe plutonium?  Invariably, it is described as the most 1) toxic, 2) hazardous, 3) dangerous material on earth. It seems that no matter the context, these adjectives or strings of other adjectives are used in the preamble. (See! I just did it.)  It is though plutonium really is thought of as a manifestation of the dark forces thrusting upward from the underworld. Certainly the name and applications infer some malevolent attributes.

I think this curious attitude to a chemical element exists because most people have no other reference point. In reality, plutonium is a dense radioactive metal, grey in color and sensitive to water and oxygen. It is/was produced by the reduction of plutonium  cation with metallic calcium. Like a number of other metals you can’t handle it in the open or without protective garb and inert atmosphere.

I have never heard a credible comparison of it’s chemical vs radiological hazards.  Is it chemically toxic, or does the radiological hazard drive the issue.  My guess is that the radioctivity dominates.

Its radioactivity (Pu-239) and chemical reactivity render it useless for much of anything outside of fission-related uses. It’s not even a good paperweight. You wouldn’t want to have a criticality accident on your desk when you spilled coffee on it. Think of the paperwork. Blue flash and heat pulse …

The same curious treatment is afforded phosgene.  Any mention of this substance outside of a chemistry journal invariably recalls the early uses in trench warfare.  The one time I used it as a post-doc, the purchase order for one mole of phosgene in toluene came back to me in the perspiring hand of the Dean of the College. He called me to his office and wanted to know precisely what kind of harm was I inviting to the University. Literally, he wondered what the neighbors would think.

This university was in a wealthy and exclusive neighborhood of a large city in Tejas. What would the neighboring plutocrats think of having research done with a WW-I war gas in their neighborhood? What if *gulp* there was a release?  That’s a fair question.

I was requested and required to write a letter describing the proper emergency response to a spill and what procedures I would put in place to prevent a mishap. This was not a memo of understanding, but rather it was CYA for the Dean in the case of an accident. He could wave the letter around in the inevitable investigation after an incident. He would pass it to my one remaining hand so I could read it publically from my hospital bed for maximum effect.

Oh yes, at near-threshold levels, phosgene has a fragrance very similar to lilac.

The Nanny State. Gaussling’s 5th Epistle to the Bohemians.

“We live in an age of miracle and wonder” is the refrain from Paul Simon’s album Graceland. All around us and through us are engineered materials devised for their specific physical and chemical properties. Time-released magic bullet drugs that inhibit specific enzymes. Flavorants, colorants, rheology modifiers, and manufactured food substances are engineered and marketed to satisfy our lizard brain’s willingness to shell out cash-for-calories and stimulate our limbic system’s emotive triggers. 

It is nearly impossible to avoid contact with manufactured goods that aren’t modified by chemistry. A century and a half of tinkering with substances at the nanometer scale has given us the ability to optimise the composition and performance of products that make our lives easier and safer.  Microprocessors and Lycra, Hastelloy and Lipitor. The chemical industry has evolved to produce the raw materials and finished goods needed for the performance we have come to expect.

However, history provides a record of the problems associated with the exuberant but uncritical acceptance of this flood of manufactured goods.  From radium poisoning of watch dial painters to chromium VI to asbestos, there is a long list of negligence and environmental insult. The trail blazing of chemical industry leaves behind it a chronicle of tragedy as well as benefits.

The result of the checkered past of industry is a growing (some would say “metastisizing”) intertwined web of state, federal, and international regulatory oversight and requirements. And with it- perhaps as a result of it- has come institutional risk aversion

In general way, risk aversion is a type of survival trait and is probably hardwired into our brains. It is hard to blame people for being wary or fearful of risks, especially those they do not understand. But on the other hand, risk aversion is also a type of inertia. It is a fulcrum from which metaphysical rather than physical justifications are leveraged.  

At what point does concern for safety become excessive and how does one go about commenting on it? In a sense, it is similar to being critical of a religion. Similar to interpreting religion, we interpret that safety is important, but we do not often have a clear path mapped out for us through the maze of details and choices.

It is possible for organizations to be dominated by confident voices that are risk averse. Meeting facilitators will piously intone that “safety first” is our policy.  Detailed SOP’s will issue, dragging out the most elementary actions into numerous steps.  There is great merit to SOP’s, but enlightened and proactive management of hazardous operations personel is more important.

Organizations can find themselves spiraling into micromanagement of even the smallest details for fear that a regulatory or liability hammer will fall at any moment. Indeed, if one studies the regulations in detail, it is easy to fall into this habit. Risk aversion isn’t just a personality issue, it is statutory.

Statutory risk aversion is the domain of the Nanny State. The name “Nanny State” refers to the sum total of regulated actions and conditions in our lives as well as the set of penalties.  Though perhaps well intended, the Nanny State seeks to zero out risk, even for the less risk averse.

The Nanny State makes the startup of new chemical technology companies prohibitively expensive.  Nobody advocates the idea that we should be free to pollute and risk the lives of workers and communities.  But even for the most skillful and well intended, there are too many regulatory landmines to dodge: air, water, and waste permits; local zoning; OSHA; EPA (TSCA); fire codes; insurance inspections; MSDS’s in multiple languages; ITAR; and DEA. All have reporting requirements, statutes, and paper trails to maintain.

The plant is the domain of the chemical disaster. The inner offices are the domain of the administrative disaster.  Executives fear being out of regulatory compliance almost as much as an exploding 1000 gallon Pfaudler reactor (alright, I exaggerated … slightly).

In my view, the USA is becoming ossified in Nanny State paralysis in much the same way the EU has.  The combination of technological risk aversion along with the popular sport of outsourcing by our nations corps of MBA wizards only serves to accelerate the de-industrialization of the USA and the EU.

In Memoriam. Professor Albert I. Meyers.

[Note: An announcement is posted in this blog on 27 January, 2008 concerning a gathering at CSU on 22 Feb., 2008.]

This morning I learned of the passing of one the great pioneers of asymmetric organic synthesis- Dr. Albert I. Meyers, University Distinguished Professor of Chemistry at Colorado State University, on mole day, October 23, 2007.  I do not know the cause of death this moment, but he did suffer from heart problems for quite some time.

Professor Meyers got his PhD at New York University under Ritter in 1957 and later did a post-doc with E.J. Corey. He wrote a book on heterocyclic chemistry and got the highest synthetic chemistry honor of all- a named reaction; The Meyers Aldehyde Synthesis.

Meyers was best known for his developmental work with stereodirecting, chiral auxiliaries. The Meyers group developed asymmetric C-C bond forming reactions with oxazolines, formamidines, and bicyclic lactams. Enantiomeric carboxylic acids, amines, cyclopentenones, etc, were prepared by his group. Numerous natural products, including Maytansine, were the result of methods development from this group.

While asymmetric catalysis would eventually capture more attention later on, the early work with chiral auxiliaries helped to develop a more solid understanding of the mechanics of asymmetric induction or chiral transfer as some put it. The specialized vocabulary of stereochemistry was the norm within the group. Napkins at the local drinking establishments were often covered with scribbled drawings of diastereomeric transition states and arrow pushing over chemical structures.  AIM in particular had a knack for 3-D chalk sketches of chiral alkaloids.

The Meyers group at Colorado State in Ft. Collins was typically rather large and quite international. There was a time in the 1980’s and 1990’s when a special magic permeated the department. This was the era of Jack Norton, Louis Hegedus, John Stille, and Al Meyers- heavy hitters all and located at a northern Colorado Ag school.  It was a time of organometallic chemistry and asymmetric synthesis.  For the student, it was an exciting time and place to be doing chemistry. I count myself as extremely fortunate to have been there.

His love for his mistress- chemistry (as he put it)- was all consuming.  AIM had a sort of panache that generated enthusiam among the group. AIM loved the science and the people of chemistry.  Lunch with AIM was story time. He was very convivial and would regale his audience with amusing anecdotes of his travels and brushes with some of the larger-than-life characters in our field.

The Meyers group was a colorful lot. Multiple languages and strident voices could be heard in the lab against the tapping of chalk on the blackboard. AIM loved nothing more than to be engaged in a blackboard discussion with his sharpest students trying to noodle out some mechanistic or stereochemical problem.

He was a great guy and we’ll all miss him.