[shelley]

Hi, can you tell me from the list below which of the listed chemicals are able to go through sublimation besides water?
Reagent   Formula
Acetic acid, glacial (conc.)
17.4 M   CH3CO2H
Isoamyl alcohol
(3-methyl -1-butanol)   (CH3)2CH(CH2)2OH
Sulfuric acid, conc.
18 M   H2SO4
Distilled water
   H2O
Diethyl ether
   
5% sodium carbonate (aq)
   Na2CO3 (aq)

Sat. sodium chloride (aq)
(brine)   NaCl(aq)
Calcium chloride (anhydr)
   CaCl2
acetone, wash
   
Isoamyl acetate   CH3CO2C5H11

[curiouscat]

What did Mr. Google say?

[solyaris]

sublimation =
solid--->gas--->solid
so...
none of the above (liquids)
unless you have a different definition where liquid--->gas--->liquid--->solid is called sublimation.

But then I would check your definition of sublimation - and perhaps correct the person who asked you the question, if they think that any of those liquids sublime.

[Dan]

none of the above (liquids)

Not true. Being liquid at 1 bar and 20°C does not mean it cannot be sublimed at lower pressure. Water sublimes below 6 mbar - this occurs in freeze drying.

http://en.wikipedia.org/wiki/Phase_diagram

[solyaris]

Ok, fair enough. If temperatures and pressures can be changed then...

But in a practical setting, I would melt the sample anyway.. only then it isn't a 'true' sublimation.... but it can be a more efficient sublimation.... especially with an entrainer gas...
but the question wasn't about practical application - so..

[Arkcon]

We really don't know enough context from the O.P. to determine that this is a practical or theoretical application.  Although I'd love to see the technical definition of 'true'  or 'efficient' sublimation.

[solyaris]

I'll give you my technical definition, if I wasn't clear:
"True" sublimation = solid ---> gas ---> solid (with no liquid phases either on heating or cooling).
"Efficient" relates to the degree of separation of compounds/enantiomers/whatever.

Entrainer sublimation is the most efficient means of purification - there's a good chapter in a book Chemical Separations by Clifton E. Meloan - with numbers and equations too!

In practical application, the degree of separation is increased by melting the solid first - so that this is then not a "true" sublimation. But only to a pedant! 

"Ultra-purification" of metals etc. is typically done using entrainer sublimation - because of its "efficiency". 
I believe that the original question was a homework question - and thankfully I don't have to answer it!
Why has someone taken a mole snack?! Is it to discourage contributions or something??? I can take a hint! Bye!

[curiouscat]

Not true. Being liquid at 1 bar and 20°C does not mean it cannot be sublimed at lower pressure. Water sublimes below 6 mbar - this occurs in freeze drying.

If that's true what does the phase diagram of substances that don't sublime look like?

The Solid-Vapor Phase Transition Line (Red in fig. below) will always exist, won't it, unless the Triple Point goes all the way down to 0 K? If that's so every substance will sublime, if only at very low pressures?



What am I getting wrong?

[Dan]

The Solid-Vapor Phase Transition Line (Red in fig. below) will always exist, won't it, unless the Triple Point goes all the way down to 0 K? If that's so every substance will sublime, if only at very low pressures?

That is also my understanding. Though I think helium is the exception, perhaps there are more.

[solyaris]

The wording of the original question -- "besides water" -- suggests that changes in temperature and pressure are to be considered also - in which case the answer is "they all sublime" - but that rather defeats the purpose of the question - and the solutions would sublime twice - as it were!