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I have a compound, dimethylaminoethanol (DMAE) bitartrate, which I originally purchased as a supplement and possible smart drug. I bought an absurd amount of it. It didn’t do anything for me as a supplement. I understand that DMAE, not the bitartrate salt, is commonly used in cosmetics, & I’d like to play with it for that purposes, maybe mixing it with glycerin, etc. Is there a simple way to strip off the bitartrate anion and have it precipitate or sublimate or something, leaving the DMAE behind? Or otherwise separating the DMAE out from the salt?

I have a strong preference for any other reactants and reaction products being non-toxic

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I see on Wikipedia: "Dimethylethanolamine (DMAE or DMEA) is an organic compound with the formula (CH3)2NCH2CH2OH. It is bifunctional, containing both a tertiary amine and primary alcohol functional groups. It is a colorless viscous liquid. It is used in skin care products."

Now the fact that it is used in skin care products does not make it safe: the SDS (https://www.fishersci.com/store/msds?partNumber=AC116180010&productDescription=N%2CN-DIMETHYLETHANOLAMINE+1LT&vendorId=VN00032119&countryCode=US&language=en) shows these pictograms:

enter image description here

Uh oh! Oh, well.

Well, let's forget that for a minute. DMAE is a liquid, boiling at 134C. Bitartrate anion is very insoluble if attached to potassium (potassium bitartrate is cream of tartar). If you added a stoichiometric amount of potassium bicarbonate (KHCO3, quite safe) to an aqueous solution of DMAE, you would precipitate almost all of the bitartrate, leaving the DMAE in water. Filter off the ppt and distill off the water and then distill and collect the DMAE. It will probably be a little wet and you will hate the overwhelming fishy smell.

Oh, and use a respirator (from the SDS: "Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.")

Good luck. Actually, I think you will have better luck if you do something else.

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  • $\begingroup$ You have persuaded me that this is a bad idea. Thank you. Though I admit that I am a little puzzled by something acutely toxic if swallowed being readily available as a supplement, and often used in cosmetics as a severe skin irritant. $\endgroup$ – andrewH Mar 21 '20 at 20:35
  • $\begingroup$ Preumably used at very low concentrations in cosmetics as it causes burns $\endgroup$ – Waylander Mar 21 '20 at 22:05
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This might work: Make a solution of NaOH in absolute ethanol, e.g. at a 1 mol/L concentration. Suspend the DMAE bitartrate in ethanol, and add 2 equivalents of the NaOH solution slowly to the suspension, making sure it doesn't heat up too much. After everything is added, stir or agitate it for a while. Then filter off the solids and wash them with some ethanol. Add the washings to the ethanol solution. From this solution, let the ethanol evaporate, and only DMAE should remain. The solids are sodium tartrate.

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  • $\begingroup$ SAFETY - I'd be very wary of using NaOH one step before collecting the product which is to be used in some cosmetic formulation. It is highly doubtful that the OP has the right equipment/techniques to test the collected product for a NaOH impurity. $\endgroup$ – MaxW Mar 21 '20 at 9:21
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    $\begingroup$ I assume people attempting any chemistry know about safety. Would you put safety statements in the electronics forum when people ask questions about voltages higher than 40 V and would you vote down answers that are "unsafe"? IMO personal responsibility and knowledge of basic safety is assumed on an exchange like this. $\endgroup$ – René Becker Mar 29 '20 at 21:52

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