Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: TheOrganic on December 30, 2013, 06:18:49 AM

Title: Solubility of Mono halogenated acetic acids
Post by: TheOrganic on December 30, 2013, 06:18:49 AM

Hi,

For my paper, I need to do a reaction (determination of enthalpy of solvation) of mono-halogenated acetic acids ( 2-Fluoroacetic acid, 2-Chloroacetic acid, 2-Bromoacetic acid and 2-Iodoacetic acid). I need to get the enthalpy of solvation in some aprotic solvent.

I need any source of information which gives me details about the solubility of these compounds in DMSO, DMF etc. I need an aprotic solvent in which all of these 4 compounds are soluble.

I did an extensive search, but I could not get concrete information. I tried to counter-search, by searching for solvents in which HVZ reaction takes place ( assuming that products of HVZ reactions are often mono-halo caroboxylic acids ).

Will be nice if someone throws some light.

Thanks 

Title: Re: Solubility of Mono halogenated acetic acids
Post by: billnotgatez on December 30, 2013, 08:11:08 AM

We can assume you check these sites (especially the last link)?

Haloacetic acids
http://en.wikipedia.org/wiki/Haloacetic_acids
Chloroacetic acid
http://en.wikipedia.org/wiki/Monochloroacetic_acid
Bromoacetic acid
http://en.wikipedia.org/wiki/Monobromoacetic_acid

http://lxsrv7.oru.edu/~alang/onsc/solubility/allsolvents.php?solute=chloroacetic+acid

That is all I could find quickly with GOOGLE and WIKI
Do not have access to CRC right now
I expect you did the same with greater patience with little result
I thought the WIKI would have references that might help - but it look as not so

Title: Re: Solubility of Mono halogenated acetic acids
Post by: TheOrganic on December 30, 2013, 02:39:02 PM

Quote from: billnotgatez on December 30, 2013, 08:11:08 AM

We can assume you check these sites (especially the last link)?

Haloacetic acids
http://en.wikipedia.org/wiki/Haloacetic_acids
Chloroacetic acid
http://en.wikipedia.org/wiki/Monochloroacetic_acid
Bromoacetic acid
http://en.wikipedia.org/wiki/Monobromoacetic_acid

http://lxsrv7.oru.edu/~alang/onsc/solubility/allsolvents.php?solute=chloroacetic+acid

That is all I could find quickly with GOOGLE and WIKI
Do not have access to CRC right now
I expect you did the same with greater patience with little result
I thought the WIKI would have references that might help - but it look as not so

Thanks for that. I did check the last link, however, the site does not return any search-results for fluoro,bromo and iodo acetic acid. I need a bona-fide evidence of an aprotic solvent, in which ALL four are soluble.

Further help appreciated.

Title: Re: Solubility of Mono halogenated acetic acids
Post by: BobfromNC on January 02, 2014, 04:51:09 PM

I would be surprised if they are not all soluble in DMSO, most every small organic acid I have dealt with was.   It should be easy enough to test this with a small amount in a vial or small test tube.