so this is not a cherry phosphate recepie?

[vaskidmark]

http://orgprepdaily.wordpress.com/2008/08/02/a-phosphine-that-will-get-you-fired/

This phosphine will get you fired
Filed under: lab destruction, lit highlights, mechanisms — milkshake @ 11:32 pm


Beautiful asymmetric transition metal-catalysed chemistry with phosphine ligands chiral on phosphorus dates back to Knowles and Mislow. But these P-stereogenic homochiral phosphines are usually harder to make, so they were eventually supplanted by ligands with chirality on carbon. As a freshman I used to work for a young assistant prof in Prague - and since I was very interested in asymmetric synthesis, he suggested that I could do a thesis work with him on these ligands; We would put some chiral but racemic phosphine building block onto optically active binaphtyl piece derived from BINOL, and we would get BINAP-like ligands with both axial chirality and chirality on phosphorus. We would then try to separate the stereoisomers and see which one worked better in Rh and Ru-catalysed asym hydrogenations, and we would try to interconvert the stereoisomers to see how the kinetic vs thermodynamic induction control looks like, etc. (Chiral phosphines are conformationally labile on phosphorus above 100C whereas the 2,2′-disubst binaphtyl pieces are fairly stable and should not racemize).

It goes on for quite a bit more.  And then there are the comments.

IIRC there are a few APSers who not only understand this stuff but have played with something like this.  What I want to know is, besides a really bad smell, will there be an earth-shattering kaboom?

stay safe.

[AJ Dual]

Sounds like some smart cookie should start mailing this stuff around rather than the idiots making barn-grade Ricin. 

[Bob F.]

Huh??

[Physics]

Huh??

A chemist made some REALLY smelly stuff.  Smelly enough that he was fired from the lab he worked in.  Which takes the cake, because chemists make some crap that smells really freaking bad. 

[AJ Dual]

A chemist made some REALLY smelly stuff.  Smelly enough that he was fired from the lab he worked in.  Which takes the cake, because chemists make some crap that smells really freaking bad. 

Yeah, and it's not like skunk-bad, or worst rotten body/animal/poop/barf you can imagine-bad...

It's like the olfactory version of nails on a blackboard, or electric shocks/funnybone nerve feeling.

Unnatural-bad. Because it's something that no common biological process or peutrification would come up with on it's own.

[brimic]

I used to synthesize this stuff:
http://en.wikipedia.org/wiki/Tetrakis(triphenylphosphine)palladium(0)

Neat stuff. Its a tennis ball bright yellow green in color, it gives off bright yellow sparks when you shake a flask of it, and breaks down rapidly when exposed to oxygen.

Some of the phosphines were horrendous smelling.
I've worked with many thiols which smell very very bad- bad enough that someone a 1/2 mile downwind called the fire department when a drop of the stuff was spilled. I got an accidental whiff of a phosphine once  (I didn't let the lab clear out long enough after opening up a distillation) and immediately puked my guts out.

At least this stuff only smelled bad and wasn't esplody. Most of the stuff I worked with were Boranes, silanes, and grignards. We used to do some incredibly dangerous stunt chemistry for about what mcDonalds workers get paid these days.

[brimic]

Yeah, and it's not like skunk-bad, or worst rotten body/animal/poop/barf you can imagine-bad...

It's like the olfactory version of nails on a blackboard, or electric shocks/funnybone nerve feeling.

Unnatural-bad. Because it's something that no common biological process or peutrification would come up with on it's own.

There was a lady I worked with in the last place I worked that absorbed something that she was working with just by being in the same room as it. She thought it was on her shoes/ labcoat/clothes or something and discarded them all, but she stunk like a corpse for about a month.

[AJ Dual]

Not in the smell department, but I've worked IT with several guys over the years who'd been stationed at Aldrich Chemical by their various firms.

They had a lot of stories.

One guy who'd come from Aldrich, the first week at my jobsite, we were walking down the hall to check on something at St. Luke's Aurora, the floor was freshly polished and kind of sticky in the clean sense of the word, and suddenly there was this squish noise, and he stumbled.

Both of his shoe soles had peeled off, and stuck to the floor. 

He wasn't that surprised, but said he thought the shoes had another month left in them. 

[brimic]

Not in the smell department, but I've worked IT with several guys over the years who'd been stationed at Aldrich Chemical by their various firms.

They had a lot of stories.

Both of the Milwaukee and Sheboygan sites are pretty exciting places to work.

We had 2 fires in my building when I worked in Sheboygan back in 98 or 99. The first fire started in our pyrophoric storage room, which we think was started by one of several 50L flasks containing triethyl arsenate spontaneously combusting. There were probably 100 or more cylinders of various angry chemicals in that room, some of them launched a  1/4 mile into neighboring farm fields, some exploded days later. They ended up digging a huge pit, and bring a robot in to remove all of the damaged cylinders, then drill holes in them to allow them to burn off in the pit.

The second was caused by a chemist on 3rd shift. He was on what we called our 'diborane' generator. He laots of experience, but thought he knew everything before he came to our lab. To make a long story short, he pulled a piece of tubing that was blowing diborane gas out of a flask full of ether. He spent many months in the burn ward and is damn lucky to be alive.