Has a carbon analogue of poly(dimethylsiloxane) been synthesized?

Question

Consider poly(dimethylsiloxane) (PDMS), a member of the family of silicone polymers:

Now, imagine its carbon analogue:

I've not been able to find any evidence that this carbon analogue has been experimentally prepared. Searching for "poly(dimethylalkoxane)" got me nowhere. I eventually searched for "dimethyl polyoxymethylene," which turned up the unsubstituted variant of the above, polyoxymethylene (POM):

as well as methyl-capped POM oligomers, polyoxymethylene dimethyl ethers:

But, no "poly(dimethyloxymethylene)" was forthcoming.

Has the carbon analogue of poly(dimethylsiloxane) been synthesized? If so, what name has it been given?

What you are looking for is the polymer of acetone, not "poly(dimethylalkoxane)". — DHMO, Jan 21 '17 at 15:04
@DHMO Sure! Whatever it would be called, I haven't found the name yet. If you find it and post an answer with a link & description... winner! — hBy2Py, Jan 21 '17 at 15:05
I have not been able to find anything... acetone does have dimers and trimers but those are not what you would expect... — DHMO, Jan 21 '17 at 15:07
http://www.sciencedirect.com/science/article/pii/0032386170900807 http://onlinelibrary.wiley.com/doi/10.1002/apmc.1996.052360101/pdf — Mithoron, Jan 21 '17 at 15:12
So, if I read those links correctly, @Mithoron, the acetone polymerization apparently goes to products other than the polymer of interest? — hBy2Py, Jan 21 '17 at 15:28
http://chemistry.stackexchange.com/questions/25115/acetone-and-sodium-hydroxide/ — Curt F., Jan 21 '17 at 18:22
So, @CurtF., this is just supporting the argument that polymerization of acetone does not yield the polymer of interest? — hBy2Py, Jan 21 '17 at 18:25
The dimer exists, at least in chemical databases, and it is called 2,2'-oxydipropan-2-ol. However, according to ChemDoodle the proper IUPAC name is 2-(1-hydroxy-1-methylethoxy)-2-propanol. I didn't find any evidence for the existence of the trimer or polymer in any databases, though. — Curt F., Jan 21 '17 at 21:36

score 4 · Accepted Answer · edited May 29 '17 at 09:24

The comments to the original question do well to demonstrate that acetone polyacetal (or polyacetone; names in the literature vary, but these are the most common) is extremely difficult to produce by typical polymerization methods; this is mainly due to thermodynamic reasons, though acetal dimers and trimers of acetone have been produced at very low temperatures.¹

Polyoxymethylene is the polymeric form of paraformaldehyde (formaldehyde oligomers), which forms spontaneously in aqueous solutions of formaldehyde. The methyl-capped paraformaldehyde and polyoxymethylene would form if methanol is added to the solution; indeed, this is actually typically done to limit the length of paraformaldehyde oligomers. Polyoxymethylene, as a homopolymer, is quite stable and machinable, provided end-capping is performed; this is typically done with acetic anhydride.²

Burnop, V. C. E. Polymer 1965, 6 (8), 411-417. DOI: 10.1016/0032-3861(65)90025-X
Boyer, Lyndon D.; Sorenson, Wayne R.. Polyoxymethylene process. U.S. Patent 3355428, issued November 28, 1967.

Has a carbon analogue of poly(dimethylsiloxane) been synthesized?

1 Answers1