Sciencemadness Discussion Board

Hydrogen peroxide synthesis - 2-ethyl-9,10-dihydroxyanthracene

Saber - 5-5-2009 at 12:03

I am a fan of taking industrial procedures and downsizing them to lab size for producing extremely useful chemicals, which are normally expecive/hard to get, eg, Oleum.
I have been looking into H2O2 manufacture for a while. This is solely for fun however seeing as I can buy 30% H2O2 cheaply and easily.
The route via 2-ethyl-9,10-dihydroxyanthracene seems the most interesting. The only difficult part of this reaction would be the hydrogenation of the 2-Ethylanthraquinone produced, however, this is manable seeing as I have recently invested in Raney Nickle and a hydrogen tank. I plan on using a 2l buchner funnel for the hydrogenations, as I have found in the past these have been more than suitable for the pressure/temperature required.
Now I know the procedure seems simple, and the reagents reusable, I need to buy/synthesize some 2-ethyl-9,10-dihydroxyanthracene. This reagent is nearly impossible to buy, and it is extremely expensive! Has anybody had a go at synthesising this compound, and if so how would I go about doing this?
I guess a alkylation of anthracine, followed by oxidation, any ideas?
Thanks for any ideas,
H2O2 for everyone!

-TheMadMen- - 31-5-2009 at 06:37

Hi, i too was once fascinated with making H202, as it is indeed a very useful, and fabulous chemical, with multiple uses. But as i'm sure you also figured out, it is difficult to make, which is a pissoff, since it's just water with an added oxygen atom.

If you have raney nickle and a hydrogen tank, i feel that you are insane pursuing the manufacture of H202, why not just try and make it by passing an ultraviolet lamp through DH20 ? Doesn't that work? I Hear.

Saber - 31-5-2009 at 10:40

@-TheMadMen- Sorry I must of put my question out badly in the beginning, I am not at all interested in getting hold of lots of H2O2, I can buy it extremely easily and cheaply (500ml of 30% is £5 per litre). The only reason I wanted to try this out is for fun, however being able nto produce H2O2 at any concentration will be a bonus.

I guess, seeing as nobody has replied to my question that nobody knows how to make 2-ethyl-9,10-dihydroxyanthracene, guess its back to the drawing board… it doesn’t look that difficult!
I am gonna order some Anthracene in and start from there…

Formatik - 31-5-2009 at 14:46

Look especially in the patent literature. E.g. see example 3 of the attached patent below.

Attachment: GB465070.pdf (374kB)
This file has been downloaded 601 times

unionised - 1-6-2009 at 09:52

How good is your French?

Saber - 1-6-2009 at 10:31

Sweet, thanks Formatic and unionised! great patents!
@unionised- google translate worked perfectly for it!
Here is what im going to do, buy Fisher lab grade styrene (or it can be made by pyrolysis of polystyrene = cheap!), then hydrogenate it with raney nickle to produce ethylbenzene.
This is reacted with phthalic anhydride (Fisher A.R). The patent mentions that it must be done in HF and BF3. The BF3 I can deal with but the HF I simply cant, that stuff will eat away at my glassware if hydrated and is highly TOXIC. Luckily enough the patent mentions nothing about water so I guess if I do it in anhydrous HF it will be fine (HF doesn’t attack glass when dry :) )
The next step requires 20% oleum, this should be fine, will just get my contact process up and running :D

Here is the tranlated version of the patent;

[Edited on 1-6-2009 by Saber]

pHzero - 1-6-2009 at 10:31

Quote: Originally posted by unionised  
How good is your French?

"Procedure for the synthesis of 2-ethylanthraquinone

This invention concerns a procedure for the synthesis of 2-ethylanthraquinone (EAQ) from ethylbenzene (EB) and phthalic anhydride (AP) reacted in a liquid mixture of HF and BH3 in order to make a complex of 2-(4-ethylbenzyl)benzoic acid (EBB) of the molecular formula EBB.nHF.mBH3 where n and m are between roughly 1 and 3. The 2-ethylanthraquinone is used in the industrial synthesis of H2O2, as previously mentioned..."

Then I got bored
If anyone needs a specific section translated, let me know. I'm sure I'm not the best at french on this forum, but I'm not too bad at it and I dont mind translating a bit.

Edit: damn. Google translate. I wish I'd thought of that.

[Edited on 1-6-2009 by pHzero]