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Propylene Carbonate (An underappreciated polar aprotic solvent)

Category: Synthesis
Posted on: April 13, 2007 9:16 PM, by Molecule of the Day

Propylene carbonate is a very polar aprotic organic solvent. Usually, this makes synthetic chemists think of DMSO, then DMF, then maybe acetonitrile or HMPA. Not many people will get down far enough on their list to get to name propylene carbonate.

InChI=1/C4H6O3/c1-3-2-6-4(5)7-3/h3H,2H2,1H3

It is the cyclic ester of propylene glycol and carbonic acid. It's surprisingly robust - if propylene carbonate hydrolyzed appreciably, the container would hiss a bit when you opened it (due to CO2 release). I've actually held some propylene carbonate and 6M HCl in a sealed container for a week accidentally; no hiss.

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Comments

Chiral, too.

Propylene carbonate is the nappy-haired ho of solvents. Everybody should be MADE to use it by heinous legislation, jackbooted State compassion, virulent enforcement, star chamber courts, and protracted incarceration for violation of celebrating solvent rights.

Propylene carbonate is an honorary Solvent of Colour.

Posted by: Uncle Al | April 13, 2007 9:45 PM

Uncle Al, I saw how you started and was looking forward to one of your more intelligent and well informed posts and was pretty disappointed when you turned it into some tirade about a current event. Have you no concept of time and place? There are countless other blogs out there which deal with media issues. Heck, even this one deals with them when a particular chemical is in the news, but there is no reason go dragging political views into a post on propylene carbonate!

Posted by: Jon | April 14, 2007 12:58 PM

I don't see you defending the rights of N,N'-dimethylpropylene urea. Solventist!

When I cannot purchase halogenated solvent at market price given the Ozone Hole or Global Warming, some idiot slactivist is assassinating the future. When I pay $3.70/gallon for gasoline with "oxygenates" and the Carbon Tax on Everything while China brings an additional gigawatt of unscrubbed coal-fired power generation on-line each and very week... Bullshit!

http://en.wikipedia.org/wiki/Slacktivism
http://www.mazepath.com/uncleal/wind.htm

Sen. Edward Kennedy's kids don't get bussed or shaken down for lunch money. Support evolution - shoot back. Shoot to kill every moron with a torch or pitchfork storming the scientists' castle, for if you do not you will be dragged screaming into the village square and be burned alive while the mob cheers.

Posted by: Uncle Al | April 15, 2007 4:19 PM

I took a peek at the price difference between propylene carbonate and DMF, b/c as scientists we are always scraping for $$$: My research into this area provided some astonishing results....racemic anhydrous PC is $80 for 2 litre. ACS reagent grade DMF goes for $57/2 litre. In a cheapskate lab like mine, PC might be a "special treat" solvent (although the price diff is not that great).

Posted by: Organic Chemistry Help | April 15, 2007 6:20 PM

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