Sciencemadness Discussion Board

Obtaining methyl methacrylate

LHcheM - 20-2-2011 at 07:24

How to obtain methyl methacrylate from household products?

can anyone show me how to do it with photos and descriptions?

thanks very much =]

unionised - 20-2-2011 at 11:02

How good is your French?
http://www.youtube.com/watch?v=L9ZAuwC8mdk

LHcheM - 21-2-2011 at 07:54

although my french is 0%, but that video helped me alot and at least I got some ideas about the distillation.

THANKS VERY MUCH!!! ^^

mr.crow - 21-2-2011 at 12:28

Smells like fun!

Is it actually the monomer or is he distilling plasticizers? I love the old style apothecary jar.

Iguanaopolis - 21-2-2011 at 12:35

In the video he demonstrates the produced liquid decolourising bromine water, so I would assume he has actually made the monomer.

Hexagon - 21-2-2011 at 13:34

Anyone knows if it is true that by fusing metacrylic acid (MMA) in alkaly one can obtain propionates?

unionised - 21-2-2011 at 13:36

Most polymethylmethacrylate hasn't got any plasticisers in it.

not_important - 21-2-2011 at 16:59

Poilyacrylic plastics and polystyrene are among the easiest plastics to depolymerise, both useful for hobby source of the monomers and for demonstrating recycling. Both plastics are generally either free of or have only low concentrations of additives, colouring and solid filler being the most common. Destructive distillation depolymerisation, collecting the distillate in a flask containing a small amount of polymerisation inhibitor (hydroquinone, BHA, ...), and then a redistillation/fractionation generally gives clean product..

smuv - 21-2-2011 at 21:18

I've made Methyl methacrylate via the procedure in vogel. I used acrylic plastic cracked into pieces big enough to fit into the flask. The flask was heated via free flame. The product which came over as a slightly colored oil was redistilled to yield what I deemed to be fairly pure methyl methacrylate as a colorless oil. The product could be kept quite some time without polymerizing, but I forgot about it and it eventually did. The reaction flask (for the depolymerization) is somewhat annoying to clean. Acetone with sand did the trick, the flask came out spotless.

Oh yeah, the stuff smells absolutely rank.




[Edited on 2-22-2011 by smuv]

mr.crow - 21-2-2011 at 21:59

Cool. It smelled pretty strong when I was using a dremel to cut plexiglass.

What could the monomer be used for?

Paddywhacker - 21-2-2011 at 22:50

Acrylates were used as stink bombs at political rallies, but that was rather a long time ago. Today's youth seems so much more housebroken by comparison.

LHcheM - 22-2-2011 at 07:09

Dear smuv you said you've made MMA by free flame? How long did you take for the distillation process?
I distilled once for the monomer but it came out as some white fumes and the fumes condensed on the side of the test tube and became the polymer again. The PMMA also chars and bubbles to give off those white fumes. But it my ice cold test tube, I received nothing @@

I got styrene monomer easily from a chemical supplier, it's denoted as SM which at first I didn't recognise it. But MMA is really hard to obtain. Wikipedia saids that Shell is one of the largest manufacturer but I phoned them and they said they don't have it.

Actually what I want for MMA monomer is that I need to for my project to produce a Unsaturated Polyester Resin, then mix it with starch (or other forms) which may possibly to make it Biodegradable. But since obtaining MMA monomer is the first crucial step, I can't start it as long as I don't have MMA...

smuv - 22-2-2011 at 08:57

As I said, follow the procedure in Vogel (forum library, book called practical organic chemistry; use the index to find the prep). The yield is quantitative but the catch is, you should interrupt heating when ~80% of the product has come over, to make it easier to clean the flask.

Mr. Cow: MMA is a reasonably activated Michael acceptor as well as a dienophile. Years ago, when I didn't have much organic experience under my belt, I began a project involving the Michael addition of activated aromatics to MMA. The project never really got off the ground and even if it had I would have been too incompetent to get any reasonable results, but...if you want to try a Michael addition or diels alder...mma is very OTC and can be rapidly made in good purity with little effort or expense.

P.S. You could probably also use a heating mantle for the depolymerization.

[Edited on 2-22-2011 by smuv]

DrRoboto - 5-9-2011 at 12:24

Is there any way to go from methyl methacrylate to methyl acrylate? Perhaps you could de-esterify it to methacrylic acid in a similar way methyl acrylate can be de-esterified to acrylic acid....and then...? Thanks.

[Edited on 5-9-2011 by DrRoboto]

Fleaker - 5-9-2011 at 16:10

This is stinky stuff and rather disagreeable to one's lungs. Be safe!

DrRoboto - 5-9-2011 at 16:22

Quote: Originally posted by Fleaker  
This is stinky stuff and rather disagreeable to one's lungs. Be safe!


Also, could one depolymerize Sodium polyacrylate (no further away than the nearest poopy diaper) into sodium acrylate monomer (which could then be converted to acrylic acid via acid base reaction perhaps?)

Thanks.


Eh, crap, the answer's no:
http://www.sciencedirect.com/science/article/pii/014139109090077K
Quote:

The degradation of sodium and potassium polyacrylate was studied under programmed heating conditions using thermogravimetry (TG), differential thermal analysis (DTA) and thermal volatilisation analysis (TVA). These materials are stable up to about 400°C under programmed heating at 10° per min in vacuo. The degradation products have been investigated by IR spectroscopy, mass spectrometry and GC-MS techniques, the volatile product fraction having first been separated by subambient TVA. Degradation of these polymers leads to a wide range of products, which include dimer and trimer fragments but only traces of monomer. A mechanism has been proposed which involves both homolysis of the chain, which may be followed by intramolecular transfer and scission, and side group scission.

Sigh.

[Edited on 6-9-2011 by DrRoboto]

Fleaker - 5-9-2011 at 16:26

I never tried. My experience was making PMMA.

I doubt it would work, if it did, it would have to be some sort of dry salt decomposition, and would probably be pretty messy and give a host of products. Might need an acid catalyst.

nezza - 7-9-2011 at 10:48

This was an experiment we did at school. Perspex is polymethyl methacrylate and careful distillation of chunks of perspex gives the monomer as a rather strong smelling liquid.

Fleaker - 7-9-2011 at 18:50

Meh, looks like I guessed right.

mr.crow - 7-9-2011 at 20:42

What could you use this compound for? Plexiglass glue sometimes has the monomer in it along with DCM

bbartlog - 14-10-2011 at 18:08

Alternatively (but rather less practically) the following synthesis could be done:
- chloroform (from bleach and acetone, the haloform reaction)
- then chloretone, from chloroform, acetone and sodium hydroxide (lye)
- finally esterification with methanol, using sulfuric acid

US patent 2226645 has some details on parts two and three, although there is also a synthesis of chloretone (aka chlorobutanol, aka 1,1,1-trichloro-2-methyl-2-propanol) on erowid, which may be superior.