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Topic: Why is the formula for Bakelite so wonky?  (Read 1486 times)

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Offline Schwarz107

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Why is the formula for Bakelite so wonky?
« on: November 07, 2019, 01:04:15 PM »
I am learning about Bakelite, and looking up the chemical structure I see something I've never seen before. A wonky structure of which I don't know what's called. Why does Bakelite have such a wonky structure, and is there a proper word to describe such 'wonkyness'?


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Re: Why is the formula for Bakelite so wonky?
« Reply #1 on: November 07, 2019, 03:30:05 PM »
First of all, this is a 3D structure - but not an ordered one. Each ring is connected to up to three others, can you see it? There is an element of randomness present, which is why it is 'wonky'.
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Offline AWK

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Re: Why is the formula for Bakelite so wonky?
« Reply #2 on: November 07, 2019, 04:04:30 PM »
Polymers as macromolecular compounds do not have a strictly defined structure, e.g. high-density polyethylene (HDPE) consists of 10,000 to 100,000 molecules of ethylene in a linear chain (we do not know the exact length of the chain, but we do know that the molecule is linear). In the case of bakelite, the matter becomes more complicated.  Phenol with formaldehyde forms 2,4,6-tris(hydroxymethyl)phenol. Each of the three hydroxymethyl groups can condense with subsequent phenol molecules in positions 2, 4 or 6 (not necessarily regularly).  Two hydroxymethyl groups by condensation form irregular chains of phenolic residues connected to each other by CH2 groups and a third reactive group connects these chains in a plane or space. The picture from Wikipedia does not yet show all the possibilities (but is therefore reasonably clear).

https://polymerdatabase.com/polymer%20classes/Phenolic%20type.html
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Offline Schwarz107

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Re: Why is the formula for Bakelite so wonky?
« Reply #3 on: November 08, 2019, 02:06:32 PM »
Thanks, both AWK and Borek!

Borek, you call this an non ordered 3d structure. Would you say amorphous would be synonymous with non ordered?

I am trying to find another compound which has the same nonorderedness to it. I have googled some, but with no luck.


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Re: Why is the formula for Bakelite so wonky?
« Reply #4 on: November 08, 2019, 05:36:48 PM »
Would you say amorphous would be synonymous with non ordered?

To some extent - yes, but I have a gut feeling it can be dangerous to treat these terms as equivalent.

I am trying to find another compound which has the same nonorderedness to it. I have googled some, but with no luck.

Probably depends on what you mean by "the same".

Trick is, this is an interconnected structure, different from a typical linear polymer. At the same time any polymer made from meres capable of connecting to at least three others will give macromolecules of similar structural properties.
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Offline Schwarz107

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Re: Why is the formula for Bakelite so wonky?
« Reply #5 on: November 09, 2019, 01:16:50 PM »
Much appreciated!

What I meant with same, was any 3D structure that looks like it's seen through a funhouse mirror, like the one for Bakelite.

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Re: Why is the formula for Bakelite so wonky?
« Reply #6 on: November 09, 2019, 01:34:30 PM »
Mix of the structure type (number of possible bonds between meres) and the way it is drawn.
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