Author Topic: Synthesizing Trimethyl Phosphate  (Read 109 times)

LYC

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Synthesizing Trimethyl Phosphate
« on: March 17, 2009, 11:18:57 PM »
Trimethyl phosphate is one of the safer methylating agents around, it is still toxic, but not as bad as the methyl halides or dimethyl sulfate. I haven't seen any ways to make it so do you guys have any ideas?


You would hope it were as easy as mixing phosphoric acid with methanol, but I'm pretty sure it isn't, maybe you know otherwise?


I had two ideas that I think could produce TMP.


The obvious one is to heat phosphoric acid into (HPO3)n, which is either called polyphosphoric or metaphosphoric acid. (HPO3)n is a solid, and I think it is a polymer, but the important thing is that it has an extremely high dehydrating potential. I think it would be able to form TMP by refluxing with methanol. This  reaction would produce not only the TMP but also some phosphoric acids which could be separated by distillation and dehydrated to (HPO3)n again by heating.


The disadvantage to doing it this way is that you need a really resistant vessel to heat the phosphoric acid in and it requires quite a bit of heat.



The other idea I had was mixing pure phosphoric acid with glycerol and heating. Glycerol and phosphoric acid have higher boiling points then water and I think phosphoric acid and glycerol would form an ester that could then react with methanol to form glycerol and trimethyl phosphate. This reaction happens with boric acid and glycerol.


This seems to easy to work, so I'm sure something is up? I fear that maybe acrolein would be produced instead, or phosphoric acid may not fully form an ester with the glycerol.


Any other ideas? I'd like to get a hold of this chemical!

Vesp

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Re: Synthesizing Trimethyl Phosphate
« Reply #1 on: March 17, 2009, 11:29:54 PM »
Interesting ideas!

Here are some patents that are probably useless since it involves making it, or similiar compounds with phosphorous oxychloride but I figured I'd post them anyways.
. http://www.freepatentsonline.com/6673955.html
http://www.freepatentsonline.com/6034260.html


What about the possibility of making TMP by forming phosphate esters with fatty alcohols and phosphoric acid and then performing a transesterification with methanol? The fatty alcohols boiling points are a lot higher then that of waters, and I'm sure the esters would be significantly higher so this would allow them to form easily. I suggest using the fatty alcohols  since they are a lot more stable, and heat resistant then glycerol is, after all, what could they decompose into?

You'd probably want to use a saturated fatty alcohol, maybe phosphoric acid could react with the double bond, or they could get oxidized in the process and lead to some problems?

Good thread though.
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LYC

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Re: Synthesizing Trimethyl Phosphate
« Reply #2 on: March 19, 2009, 02:13:11 AM »
Hmm seems my idea isn't to crazy, the can produce trimethyl and triethyl phosphite via transesterification of triphenyl phosphite.  Trimethyl phosphite might be just as useful.