New Failure Modes

Chemistry can be very humbling.  A person can be absolutely sure of how a new reaction or process will turn out and yet be absolutely dead wrong.  Process research is an engine that consumes dollars and churns out new failure modes in one big pile and positive results in a smaller, steaming heap. 

I have been working with ionic compounds that have weakly coordinating anions.  I’m finding that my finely honed intuition built from years of shame, suffering, and cruel humiliation is turning up flat wrong more times than I care to admit. A house of cards.

More than a few of these compounds seem to participate in the formation of a liquid phase in the right combination of solvents.  If I were keen on monkeying with ionic liquids, this would be just dandy.  But the product is a solid and I want to purify it by xtallization.  I’m tempted to categorize these liquid phases as clathrates, but I’m unclear if the definition will acommodate such a thing. In each case, a normally miscible solvent pair is required to split out the new phase when the weakly coordinating ion pair is dissolved in the more polar solvent. 

There is a happy ending to this.  I was able to isolate solid product from a 2-solvent system, but sadly, I would be hunted down and shot like an egg-sucking dog if I disclosed it.  Bummer.

4 thoughts on “New Failure Modes

  1. wrw

    ah yes chemical intuition. that’s what got us here isn’t it?

    I remember a perkin medalist’s comments on using alkylhalides for promoting v(2+) catalyzed Z-N polymerization.

    He had trained with Cr and for Cr alkylhalides are poisons.

    He never would have tried halogens.

    so much for intuition.

    that is what is so much fun with patents. All you have to do is show that it was unexpected – and really a lot happens that is unexpected.

    yes?

    Congratulations on getting the molecules to do what you wanted. Chemistry is all about control.

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  2. gaussling Post author

    wrw- the point about patents is a good one. Recently a patent appln I know of that had been issued in the US was bounced by an EP examiner. He (she?) said that appln had 5 separate inventions in it. There was no such observation from the US examiner. Hmmm. What could that mean??

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