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DBL%20Hendrix%20small.png College chemistry, 1983

Derek Lowe The 2002 Model

Dbl%20new%20portrait%20B%26W.png After 10 years of blogging. . .

Derek Lowe, an Arkansan by birth, got his BA from Hendrix College and his PhD in organic chemistry from Duke before spending time in Germany on a Humboldt Fellowship on his post-doc. He's worked for several major pharmaceutical companies since 1989 on drug discovery projects against schizophrenia, Alzheimer's, diabetes, osteoporosis and other diseases. To contact Derek email him directly: derekb.lowe@gmail.com Twitter: Dereklowe

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February 22, 2012

Max Gergel's Second Odd Book

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Posted by Derek

I mentioned the fearsome memoirs of Max Gergel here, but not many people know that he wrote another volume. "The Ageless Gergel", out of print for who knows how long, is available here in PDF form. I have to note that it's even more rambling and formless than "Excuse Me Sir, Would You Like to Buy a Bottle of Isopropyl Bromide", and one also gets the impression that he used up a lot of his show-stopping anecdotes in the first book as well. I should also mention that the entire last section of the book is an account of a European vacation, during which no chemistry intrudes, and that the whole thing ends as if Gergel suddenly looked at his watch.

But there are some interesting chemical stories buried in there, and it's worth skipping through some parts to find them. This one's pretty typical:

I had been visiting Will at the plant in Elgin, South Carolina, and noticed that he smelled goaty. For that matter, the other workers seemed to have a goaty odor, too. I inquired the reason, and he took me to the source, an isolated section of the plant, which smelled horrendous. A large glass still, one that would have delighted a moonshiner in the old whiskey-making days was stinking up Hardwicke Chemical Co. and the surrounding farms. Now fatty acids have a rank odor smelling like rancid butter. The absolute worst member of the series is isovaleric acid. This smells like rancid butter with a soupgon of goat and old sneakers thrown in for good measure. As bad as it smells, the acid chloride derived from it is worse. It is so volatile that it will chase a visitor and leave its far from subtle mark. The odor is soap, water and Lysol resistant. This acid chloride reacts with mucous membrane so that while you are rendered ill by the obnoxious odor, the acid chloride is hydrolyzing with your perspiration as a reactant and eats away your lips, eyeballs and tongue. Hardwicke, committed to make this monster, was only too happy to find' Columbia Organic Chemicals Co., Inc., as a "farmout" and once more we were making something no one else wanted to make.

We had never had such a dreadful assignment. Anyone working with this "superstink" is branded and given a wide berth. No matter how amorous his spouse may be, passion crumples despite baths, Chlorox and Dentine. For a while we made isovaleroyl chloride at Cedar Terrace. It created pandemonium among residents who first sniffed each other, came to the plant to sniff us, and then sniffled to their lawyers.

Unfortunately, I can't quite put that acid chloride on my list of things I won't work with, because I have worked with it. But I can imagine that making it by the barrel would be a pretty repellent business, for sure. A 25-gram bottle was enough for me.

Comments (11) + TrackBacks (0) | Category: Things I'm Glad I Don't Do


COMMENTS

1. RB Woodweird on February 22, 2012 2:52 PM writes...

I once made a decalin derivative which smelled exactly like our PI's body odor. I used to sneak up behind the other members of our group, uncork the flask, and unleash fear and loathing on a cruel but hilarious scale.

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2. Harry on February 22, 2012 7:00 PM writes...

I actually saw Max at the Informex 2011 show in Charlotte just over a year ago. He was frail and rather far gone in Alzheimers. I haven't heard if he had passed on, but I'm not sure if I would.

At this year's Informex show, a number of us "old-timers" ended up swapping stories about Max.

Max is/was quite a charecter. The chemical business was quite different 40+ years ago, when I first got involved in it. Much of the color has gone out of it since that time.

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3. GC on February 22, 2012 8:20 PM writes...

So after Will started smelling goaty, they started calling him "Billy"?

Thank you! Don't forget to tip your waitress! I'll be here all week!

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4. Anonymous on February 22, 2012 10:44 PM writes...

I've always been confused by the incomplete application of the "-oyl" nomenclature to acyl halides. I used to think that it applied only to acids with the "-oic" suffix and not the "-ic" suffix. Hence, "benzoyl chloride" (from benzoic acid) or "mesitoyl chloride" (from mesitoic acid). But you don't write "acetoyl chloride" (from acetic acid) or "oxaloyl chloride" (from acetic acid). Yet, for some bizarre reason, it's "isovaleroyl chloride" (not "isovaleryl") and "carbamoyl chloride" (not "carbamyl") even though neither parent acid's name ends in "-oic".

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5. midwestern on February 23, 2012 11:07 AM writes...

Kary Mullis devotes several pages in his autobiography to working at Columbia Organic with Max Gergel. He tells a hilarious story of trying to make nitrosobenzene in his garage his freshman year of college to sell to Max.

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6. InfMP on February 23, 2012 11:28 AM writes...

Thanks a lot for this, I really enjoyed reading the first book and have shared it with many older chemists who had never even heard of Max.

I was never able to find out anything about him on the internet (except the Mullis story), and so I wondered if the chemicals had ever killed him.

It's good to hear that he might still be alive because that means I can withstand many more years of small exposures to Organic chemicals

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7. exGlaxoid on February 23, 2012 11:58 AM writes...

I have a friend who knows Max well, and according to him, he was still alive and kicking a month ago or so. Not bad for a man who manufactured most of the top ten known carcinogens during his career.

When I meet him many years ago, he had a nearly photographic memory and told stories even wilder then the books. The stories about dumping waste in a hole and working with very noxious chemicals are still a bit alarming, given the messes we have had to clean up; but, during WWII, I am told that companies were told that they had to produce X and Y for the war effort by date Z, or they would be considered traitors to the US.

He had one story about moving almost 1000 pounds of one pharmaceutical intermediate in the trunk of his car, which was fortunately a large one, shoveled into plastic bags. Imagine having a trunk full of white powder nowadays...

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8. monoceros4 on February 24, 2012 12:30 AM writes...

"It's good to hear that he might still be alive because that means I can withstand many more years of small exposures to Organic chemicals."

On the other hand, the chemicals might rot your brain like they did Mullis's.

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9. exGlaxoid on February 24, 2012 1:51 PM writes...

#8 - I think that was the LSD, not the alkyl halides...

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10. newnickname on February 27, 2012 10:55 AM writes...

I had some pleasurable contacts with Max and his daughter some years back. I have both books but I think he originally planned for a trilogy. I'm also glad he's still around.

(A favorite line about making methyl isocyanide for a Professor someplace: . 'Professor, why the paucity of literature since Moissan?' 'Well, Gergel, it's the toxicity. That's what killed Moissan!')

@7: The story about filling up his trunk is in one of the books. I'd check if they were handy. He was visiting a chemical plant (to drum up business) but it had shut down. The place was empty except for a guard. There was a huge pile of that powder in the parking lot and the guard told him he could take what he wanted. It wasn't anything too bad, as I recall: maleic acid? phthalic acid?

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11. JustReadIt on January 10, 2014 10:36 PM writes...

cis delta 4-tetrahydrophthalic anhydride. http://www.chemicalbook.com/ChemicalProductProperty_EN_CB5728570.htm

Page 134 of Excuse Me, Sir...

"I asked if we might have the chemicals left over from the butadiene project and after a moment's thought he took me to the window, rolled up the blinds and I saw, glistening in the morning sun, a veritable Fuji. He explained that at war's end they had a considerable amount of butadiene left over and his job had been to find novel chemicals which could be made from it. He suggested to management that they produce cis delta 4-tetra-hydrophthalic anhydride and no one told him to stop—thus the mountain. This is an example of the excellent liaison which sometimes exists between management and research."

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