Sciencemadness Discussion Board

oxidation of anethole

ribbit - 4-9-2009 at 13:56

Hey all, I'm totally new to this scene but I think I have somewhat of a mind to be useful but first I have to learn the basics!

I am attempting to convert anise oil to anisaldehyde with minimal, hopefully no leftover contaminants with OTC materials.

The first method I discovered was oxidative cleavage, suspending 20 grams of anise oil in 150 ml water and adding 30 ml of concentrated sulfuric acid with 55 grams of sodium dichromate then pulled with toulene (I imagine Xylene would work as well) to yield around 9 grams of anisaldehyde.

The roadblock I hit with this method was acquiring sodium dichromate... so I started looking into alternatives.

The question I had to ask myself was "why sodium dichromate?" Apparently potassium dichromate is used for similar things as sodium dichromate such as oxidizing but has a different solubility in water... sodium hydroxide is also available but I fail to understand why specifically sodium dichromate is needed and I wonder if sodium hydroxide would provide the same end result.

Another option could be to synth sodium dichromate but i'd rather avoid this if possible.
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So before I go forward, is there any reason why I should not use potassium dichromate?

kclo4 - 4-9-2009 at 14:48

You need to use a dichromate of some sort at least, that is what does the oxidizing. Sodium hydroxide wouldn't do anything really...

Look into the toluene-> benzaldehyde thread and read a bunch about the Mn persulfate oxidizer for making aldehydes.

Inoxia - 4-9-2009 at 14:51

Make the dichromate from the sodium hydroxide!
buy Chromium oxide from a pottery/chemical supplier then fuse the NaOH and Cr2O3.
Acidify you sodium chromate product with acetic acid glaciel to produce you Sodium dichromate!

ribbit - 4-9-2009 at 15:44

well I was able to procure some potassium dichromate but the store didn't have chromium oxide...
is there a way to use the potassium version or a way to convert the potassium dichromate into chromium oxide to further convert into sodium dichromate?

Inoxia - 4-9-2009 at 15:54

why not use K2Cr2O4 instead of the sodium salt? they work exactly the same, just use different amounts of solvent becuase the K salt is less soluble. If not reduce the k salt with anything, say ethanol, then precipitate out the chromium hydroxide with any alkali metal hydroxide salt, then use that instead of chrome oxide with NaOH.

ribbit - 4-9-2009 at 16:01

why K2Cr2O4 as opposed to K2Cr2O7?

I feel like leonidas fighting against the 300 in-acquirable chemicals list.

Inoxia - 4-9-2009 at 16:04

Sorry yes thats what i meant, im tired :(

ribbit - 4-9-2009 at 16:05

alright i'll work with the information presented TYVM!

THIS... IS... SCIENCE!!!

kclo4 - 4-9-2009 at 16:13

Make sure you adjust for the molar ratio's.. obviously.
Hopefully you know that 10 grams of sodium dichromate is not equal to 10 grams of potassium dichromate.

ribbit - 4-9-2009 at 16:20

i was thinking about that as well ty for the reminder

zed - 9-9-2009 at 19:32

Ozone.