From: Jonas Nilsson (jonni$##$ifm.liu.se)
Date: Thu Dec 21 2000 - 09:28:50 EST
A search on Beilstein gives several methods.
ethyne-d2 (650 deg C/cat.)->Benzene-d6
toluene+D2+MgO (high temp.) -> toluene-d8
ethyne-d2+charcoal->Benzene-d6+Toluene-d8
And much more. Look for yourself.
/jN
_____________________ _____________________
| Jonas Nilsson | | |
|Linkoping University | | Telephone |
| IFM | | --------- |
| Dept. of Chemistry | | work: +46-13-285690 |
| 581 83 Linkoping | | fax: +46-13-281399 |
| Sweden | | home: +46-13-130294 |
|_____________________| |_____________________|
----- Original Message -----
From: Michael Fassbender
To: Multiple recipients of list orglist
Sent: Wednesday, December 20, 2000 5:15 PM
Subject: ORGLIST: Production of deuterated solvents
Hi colleagues
After some months of recess, I am back to Orglist again. I would like
to draw the attention back to an interesting question raised by the Swedish colleague Jonas
Nilsson (Hej Jonas! Haelsningar till Sverige, min Mormor aer svensk. ;-)) quite
a while ago:
On 28-Apr-2000 14:38:16 Jonas Nilsson wrote:
> Dear Members
>
> My collegue an I was discussing over a cup of coffe about how
> isotopically enriched materials are produced. Especially deuterated
> solvents are of interest.
> I just read on the internet about how "heavy water" was made during
> world war two by careful electrolysis of large quantities of water
> which
> if I understand it right tends to make H2 leave easier than both HD
> and
> D2, thus enriching the remainder in deuterium.
>
> Questions:
> Is this still how it is made?
The question was responded to by a reference to an Oak Ridge Lab Web page,
outlining the principles of deuterium enrichment in water using H2S/NH3 exchange
equilibria. Now, since we have protic (i.e. acidic) molecules here, the issue is not
that complicated.
However, I would like to know how even non-protic, rather weakly acidic solvents are
deuterated as for instance benzene, toluene or THF. What exchange mechanism is
applicable in that cases?
These are extremely weak acids, yet they are acids, so I can imagine that treating normal
benzene or toluene with an excessive amount of solutions of e.g. NaOD (hydroxide) or even
Na ND2 (amide) would give us -after boiling long enough- a certain D-enrichment in the organic phase.
For more acidic molecules as acetone and acetonitrile these exchange rates are quite acceptable.
But is there a more viable process for the technical deuteration of benzene and toluene? I'm looking
forward to your input!
Thanks
<><><><><><><><><><><><><><><><>
Dr. Michael Fassbender
Isotope and Nuclear Chemistry
Chemistry Division, MS J514
Los Alamos National Laboratory
Los Alamos, NM 87545, U.S.A.
Phone: +1-505- 665-7306
Fax: +1-505- 665-4955
Email: mifa$##$lanl.gov
<><><><><><><><><><><><><><><><>
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