Sciencemadness Discussion Board

Separation of Guaiacol & P Methoxy Phenol

Shrinivas - 29-8-2013 at 02:56

Hi Friends

I have a crude organic mass containing Guaiacol, Di Methoxy Phenol, HQ & P Methoxy Phenol. I wish to separate these components.

I have tried distillation (vacuum) but the organic mass is getting charred.

Looking for alternative suggestions to separate these fractions.

regards
Shrini

Crowfjord - 29-8-2013 at 17:25

If vacuum distillation is not working, chromatography is probably the only other other option. Crystallization would probably be a pain with such a mixture.

How did this "crude organic mass" come about? Synthesis? If so what is the target compound? Maybe an alternative can be suggested with more information.

killer_lapin - 29-8-2013 at 18:08

If they are insoluble or slightly soluble in water you could melt the mixture in neutral or slightly acidic water then let it cool slowly. Then they should start to solidify accoring to their melting point.
Since their melting point are between 24C and 75 this procedure might be feasable.

sonogashira - 3-9-2013 at 00:27

It is probably being oxidized rather than charred, and probably looks more extensive than it is. What temperatures are they distilling at?

Shrinivas - 3-9-2013 at 20:50

Quote: Originally posted by Crowfjord  
If vacuum distillation is not working, chromatography is probably the only other other option. Crystallization would probably be a pain with such a mixture.

How did this "crude organic mass" come about? Synthesis? If so what is the target compound? Maybe an alternative can be suggested with more information.


TARGET COMPOUND IS 4-METHOXY PHENOL BUT GUAIACOL ALSO GETS GENERATED DURING REACTION. I HAVE TRIED TO HYDROXYLATE THE ANISOLE WITH ZEOLITE CATALYST USING H2O2 AS OXIDISING AGENT. MEDIUM IS LOW BOILING SOLVENT. SOLVENT GETS SEPARATED EASILY IN DISTILLATION. BUT THE ORGANIC MASS DOESNT.

Shrinivas - 3-9-2013 at 21:44

Quote: Originally posted by killer_lapin  
If they are insoluble or slightly soluble in water you could melt the mixture in neutral or slightly acidic water then let it cool slowly. Then they should start to solidify accoring to their melting point.
Since their melting point are between 24C and 75 this procedure might be feasable.


pH is acidic. Entire mass is mixture of aqueous and organic phase (but doesnt show separate layers, as it got emulsified. i tried your suggestion but it doesnt work. nothing solidifies. please suggest

Crowfjord - 3-9-2013 at 21:51

You would be better off starting with hydroquinone using methanol and sulfuric acid, ala this thread. Oxidizing anisole will give 50% yield of the para-methoxy compound at best, where the stated method has pretty high yields and only starting material to separate at the end.

[Edited on 4-9-2013 by Crowfjord]