Org Prep Daily

August 6, 2008

Raising the stink

Filed under: industry life — milkshake @ 2:46 pm

A colleague stank up the lab at my previous company with a disposable pipette tip from ethanedithiol. He dropped the tip into a trash bin outside his hood; people soon complained so he dumped the bin content into a big garbage container located in our parking lot. It was a searing-hot Arizona summer day with no wind - and the stink got taken in by the A/C system of our neighbour, a robotic engineering company.

The robotic company owned the whole building and needed more space to expand their business. They wanted us out but we had a long-term lease signed with them. For years the robotic guys have been coming up with arguments about how we violated the lease terms. They reported us to EPA repeatedly, for problems like “burying chemical waste in the desert” (they could not provide information where the stuff was burried or the witness that actually saw the incident). We had EPA on us all the time - and whenever the inspectors gave us a surprise visit it was always the robotic company that ended-up fined instead (machine oil spilled on the ground, etc) while we managed a passing grade with each inspection…

This time the robotic guys reported us to the Poison Control Center. Without telling anyone at our company, they complained that we sickened their employees (they instructed their employees to take the day off - and recommended them to report to a hospital for a check-up: they told them otherwise they wouldn’t be eligible for a work-disability compensation in case they would become later ill). The poison control in turn called the military and advised them about a “poison gas release” contaminating the place - and soon the experts from the nearby Air Force base arrived in full gear. Men in bunny suits appeared on the scene, walking slowly about our parking lot and taking samples of everything with the utmost care. 

There was a fire station located right next door too and these firemen were not that busy in the spread-out Oro Valley suburbs - they were usually putting out the brush fires on the Catalina foothills and when the desert was not burning they were there at their station hanging about. Their chief was organising drills and sports-like competitions to keep up the morale - occasionaly they were rolling fire hoses or running in their gear up and down our parking lot. So when the space-suit men showed up we were not concerned; and we were rather curious, watching them - we thought the firestation dudes were finally doing something interesting! Then a $50,000 bill came - and with it a lively debate commenced, about who is paying the astronauts.

March 25, 2008

Bleak chemistry

Filed under: industry life — milkshake @ 1:38 am

orac.jpg

Last week I run a reaction in molten imidazole without a solvent, at 240C in a pressure vessel. This reminds me – in Prague we would heat quantities of beta naphtol with neat hydrazine hydrate in a “Bombenrohr” in the electrical oven at 150C, and we were taking that alarming thing periodically out and giving it a hard shake while hot. (Bombenrohr is a fancy German word for a pipe bomb, a steel  tube with screws at ends).  The resulting ooziness was then poured and spooned out into vats of boiling water, to extract away the unreacted hydrazine, naphtol and the sideproduct - betanaphtylamine (I know how it smells so I am gonna die) - and the leftover slime was then repeatedly precipitated as HCl salt, to get 1,1′-binaphtyl-2,2′-diamine. We were making 50 g batches of the racemic stuff that way and we were then resolving them with CSA.

The meanest reaction I did was melting binaphtol with 3 equivalents of Ph3PBr2 without solvent, to get binaphtyl dibromide. The procedure called to “dilute the melt with equal volume of dry Celite, cool the mixture to solidification, break the flask and peal off the glass, crush the solidified reaction mixture into half-inch sized chunks and extract them in Soxhlet” – which I managed, except that hammering the mean black 250mL tar-ball into chunks produced lots of corrosive bits flying everywhere while I was choking on the HBr fumes.

There is no moral to this sad story.

February 24, 2008

Such, such were the joys

Filed under: industry life — milkshake @ 8:07 pm

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When I was laid off 2003 by a giant pharma company, we were told that – because we were getting a better severance payment than the absolute minimum required by law - we must sign a gag agreement. The agreement was that we won’t say anything negative about being fired and about the company that fired us. In this gag agreement we also promised that we would not disclose the severance amount and the existence of the gag agreement.

Since our closed site was quite large, they did not fire us all at once but they divided us into “waves” . I was lucky to get out early so I still got what was promised - but the colleagues fired few weeks afer me were screwed. Someone at the headquarters figured out that they were giving away too generous severance so they cut it. Many of my colleagues ended up suing the company: their class-action dragged on for years but eventually the company coughed up the rest of the promised money to settle.

I soon found a job at a medium-sized company in South San Francisco. The place was crazy – they drove us extremely hard there because the company was in trouble and we needed to save it or we would lose our jobs. So we were working like nuts “to have a clinical candidate by the end of the year”and the biggest problem was our management: they were very nervous, they made all kinds of unrealistic promises to appease their superiors but wouldn’t spend money on equipment we needed for the candidate scale-ups. The management was setting us for failure – we were short of people but they would always come up with ridiculous new ideas what else we should do for somebody, ontop of our work. So our medicinal chemistry group ended up doing the scale up, the bulk purifications, the process optimisation, and the formulation work also - while trying to find the best candidate. After 10 months I got tired of this baloney (and our boss) and since I got a job offer I prepared to quit. There was plenty of good chemists there and I talked to some friends discreetly - to see if they would like to go with me – but not discreetly enough and our management found out. And so they decided to fire me preventively. The problem was that they did not have an official reason for firing me – and they would have to pay a severance if they fired me.

The way it happened was rather entertaining: our evil boss came and asked me if the rumor was true - that I would be leaving. I said yes but I would want to stay for another 6 weeks or so, before my new job starts. She said they needed to find a replacement for me and they couldn’t advertise my job because they did not have an open position. So as a favour, please would I write an informal note about the timing so that they could start the hiring process? I wrote the e-mail and the next morning I found myself fired on moment notice. I was called into HR office in administrative building and told I cannot go back because my “written resignation was accelerated” by the HR, and my poor boss could do nothing about it “because it was a standard industry practice”. They would box and mail my stuff.

I asked HR whose idea it was – they told me our boss wanted me out. So I explained the HR that this was a manifest scam: the real reason why they fired me was the argument between me and my group leader. I told the HR the boss was going after me for some time because I criticised her management style and the decisions she made which delayed our project and hurt our company. In these difficult circumstances I did what I could to save our company and was working 14 hours a day including the weekends and I was punished for it - while my boss was trying to fabricate any reasons to fire me in order to cover up her mistakes. Now she did it in a sleazy way and she also manipulated the HR in the process. It was a textbook wrongful dismissal.

The HR immediately called my boss and overruled the firing and I went back to work. The victory lived short: the same evening the boss called an emergency management meeting - all the senior staf, with site director, etc – and she went about the terrible danger that I would steal the company’s intellectual property and lure other employees away. I found myself fired the next Monday.

It took several letters to the company director with “wrongful dismissal” prominently in them – and suddenly I got a check in the mail - over $7000 – and it was much more than they owed me for my unused vacation; it was the money that I would make if I stayed for another 2 months.  Incidentally, two months is the minimum severance required by law to be paid to dismissed employees (in California). After the check cleared I got a phone call from the headquarters: their HR boss explained that someone has made a clerical error and they overpaid me by mistake but they did not want me to return their money. You see - they could not call it severance “because I resigned voluntarily and they accelerated it” but they decided to pay my lost income to shut me up.

Some time after I left, my colleagues in South San Francisco were told that there were going to be “some limited job cuts in the future” and they needn’t to worry as the downsizing would affect only few people in some groups but the company was required by law to give a notice of possible job cuts to everybody. What the top management did not tell the employees was that the headquarters already decided to axe the company site no matter what. The top company decision was to quit the pharma business altogether – the only problem was that their research projects were unfinished. To get the best value for their research, the management needed its employees to take the projects to some reasonable stage before they could sell it to other companies. So the harder the people in the labs worked the sooner they would find themselves out of job…

And the notice was a ploy also: the legal minimum severance counts from the moment of the written notification. The employees believed the management promises that their jobs were not in danger (despite the notice) and that they were protected by the company written policies. They were told that those few people who would lose their jobs would get much better severance than the legal minimum. In fact, they did not. One day the employees were invited for all hands meeting in the administrative building and there they were told there that they can’t go back to lab again. Suddenly guards and boxes appeared at the chemistry building and the chemists were given only few minutes to pack their office belonging. They were constantly watched as to not to sabotage anything.  Despite the assurances, they all got just the minimum, which turned out to be less than 1 month salary because the notice was already in effect. (The group bosses were employed few weeks or months longer, in the empty building, in order to wrap up the projects and put the documentation together. I suppose they got a better deal.)

So as you can see, the industry has various ways of maximising the shareholders’ value. There is probably someone at your company who will get a bonus for firing you and then screwing you out of your severance.

January 23, 2008

Awful Seminars

Filed under: industry life — milkshake @ 11:18 pm

When sitting through job interview seminars sometimes one gets a speaker who struggles with the language, presents messy slides or his chemistry seems unremarkable. Please be tolerant - it is the speaker in this case who suffers more than his audience. (I still remember the shivers during my own initial presentations. When I came to US nobody could understand a word of what I was saying- except for the “beta sheet” which was causing people to giggle).

The worst speakers are experienced men - It takes plenty stubborn practice and vanity to arrive at your very own terrible presentation style. Famous men are just as susceptible to the PowerPoint bad habits (5 different font sizes in 5 mismatching colors including the “invisible yellow” favorite, with the bullet points, campy clip-art and artful themes) - and they usualy take themself seriously so they invite you to be awed, by re-emphasizing every aspect and detail of their contributions. Some people are naturally uninspiring or disorganised speakers - but the essence of giving truly awful lecture lies in one’s preparedness to be selfish and inconsiderate. When I hear “First let me very briefly outline” a FEAR strikes me because when the speaker is already apologetic at the beginning of the seminar he is most likely going to mumble through twenty introductory slides and read them out verbatim. Then after 50 minutes of incessant dribble he would look at his watch and say: “Since we don’t have much time if there are no questions I will quickly move onto the second part of my talk…”

The most nauseating seminar I have seen was given by a junior chemistry prof at a Ivy League University: His work was nice and logically presented but he tried hard to connect every tiny detail of his presentation to the precedents from his ilustrious colleagues who were about to decide on his tenure  – and who all happened to be in the audience. He would loudly and frequently praise every single one of them and then again all of them collectively - for their sheer brilliancy and fatherly guidance. This level of sycophancy would be perhaps great during award acceptance speech in Pyongyang - but on this chemistry seminar with the student audience interested in the synthesis talk the outright servility was making one cringe. (Yes it worked. He got his tenure).  Another memorable speaker that I remember listening to in despair was La Clair giving his non-hexacyclinol presentation at ACS in San Francisco in 2006.

Credit: Chad Orzel has a post on terrible seminars in physics. For the bad speakers who want to become more terrible the guidelines can be found here.

January 20, 2008

Wrestling with a robot

Filed under: industry life — milkshake @ 1:35 am

resslin.jpg credit: Adolf Born

The Varian NMR autosamplers that I worked with in my previous jobs had an oversized robotic arm grabbing on samples from a rack and then swinging around wildly, loading them into the magnet hole. The system punished users for making errors. A part of the problem was that the acquisition queue allowed the users to run the samples out of sequence and to occupy any arbitrary position in the large and rather poorly numbered rack. Absent-minded people would always enter an incorrect position or leave their sample in a wrong place.

When the robot would try to pick a sample that was missing and could not find any, it would freeze and sound angry alarm - this held up the queue until our NMR man came and re-set the damned bot. Things got worse when a sample was left in the rack position reserved for the preceding sample that was in the magnet – upon return the robotic arm would shatter both samples by smashing them one into another; this created awful mess that had to be cleaned up before the instrument could be re-set. (Also the mishap could damage the arm or ruin the spinners that cost few hundreds apiece). Sometimes I would see the dreadful thing just happening and I would run to deflect the steely arm – but you know, robots are strong and a man is no match…

November 8, 2007

Dioxins Are Us

Filed under: industry life — milkshake @ 2:18 am

mile-deti.jpg

The main dioxin-cotaminated active component of Agent Orange, 2,4,5-trichlorophenoxyacetic acid, was manufactured in Czechoslovakia from 1965 to 1968, for US military use, and supplied directly to South Vietnam. There were other suppliers but the Czech-made 2,4,5-T was the cheapest- and it also had an exceptionally high dioxin content.

Spolana Neratovice is a large organochlorine plant that manufactures bulk chemicals and vinyl plastics. For a long time it also served as the main producer of insecticides in the Eastern Bloc. A popular insecticide  hexachlorocyclohexane is made by photochlorination of benzene; HCH has several stereoisomers and only one of them, gamma-HCH aka Lindane, has the useful activity/toxicity profile - the undesired isomers are removed by crystallization. As the purified Lindane constitutes only a fraction of the crude chlorinated mixture, the Lindane manufacture generates a huge waste stream. The chemists in Neratovice were offered bonuses and other incentives to find ways of using the HCH waste for anything of value. One solution of the problem was to treat the undesired HCH isomers with alkali at high temperatures to bring about elimination+hydrolysis. This was done chiefly because one of the products, 2,4,5-trichlorophenol, was the key intermediate for production of a potent herbicide used in agriculture, 2,4,5-T. And  suddenly there was a growing demand for 2,4,5-T and the Czechs were eager to earn some hard currency…

2,4,5-trichlorophenol when heated under strongly basic conditions readily cyclizes to TCDD - the most dangerous dioxin, as we know now. But at the time, long before Seveso and Yuschenko, dioxin formation was considered just a nuisance -one of many yield/purity-affecting side-reactions. (The US military was not picky about the product purity.) 

The communist government of Czechoslovakia never acknowledged its part in the dioxin disaster -  we were told that Agent Orange was an especially terrible poison invented by the imperialists… There has been a substantial direct economic aid to Vietnam over many years though, this included also visitor-worker jobs and student visas (so there is now a substantial Vietnamese community in the cities). I wondered why Vietnam was the recipient of Czech help - but not Cuba, Angola, Syria, North Korea or any other friendly totalitarian regime. Now I think it was quite likely the bad conscience about the Spolana war legacy - and that’s how we got our great & fun-loving Vietnamese students in the Charles Uni organic chemistry class.

Credit: Drugs and Poisons for bringing up the subject of the Rainbow Herbicides

Addendum: A massive Seveso-like poisoning of about 60 workers from 2,4,5-T reactor explosion in Spolana in 1968 ended the production of this material there. The Spolana plant used to have a huge site contaminatition problem; some dioxin-and-mercury buildings were closed off but the cleanup got undeway only after the summer of 2002 when a record flood washed everything into Elbe river. The rising water in 2002 floods also lifted the massive storage tanks for liquified chlorine.  The connecting pipes tore off and about 100 tons of chlorine got out. The yellow cloud fortunately missed the nearby towns. (The slow rate of the underwater release also helped.) The typical inventory at the plant used to be 1000 tonns of liquified chlorine. The main process using chlorine - vinyl chloride production - was taken down some time before the flood because the hydrocarbon cracking unit that provided ethylene for the process blew up. Workers ignited heating gas in the furnaces – a gas that was already mixed with air – and they landed away in some distance but alive. To repair the damage the production got delayed and the electrolysis was halted also. And so by enormous luck the chlorine tanks stood near-empty when the flood ripped them from the pipes.

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