Talk:Trimethylolethane triglycidyl ether

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Started the article - the latest in the series about glycidyl ethers GRALISTAIR (talk) 18:22, 17 May 2022 (UTC)

Dubious

Please check the CAS name, as what is here appears to be a completely different compound with chlorine, and a diol. If you have access to CAS, can you see what 36366-26-4 is? Graeme Bartlett (talk) 22:26, 17 May 2022 (UTC)

By SciFinder, 36366-26-4 looks like the correct unified covalent structure--three glycidyl ethers off the central trimethylolethane core--whereas 68460-21-9 is "1,3-propanediol, 2-(hydroxymethyl)-2-methyl-, polymer with 2-(chloromethyl)oxirane". DMacks (talk) 13:37, 18 May 2022 (UTC)

So I disagree. I googles TME and here are just a few. Sigma Alrich uses 36366-26-4 and also 68460--21-9. The REACH Europe use that too. All the rest use 68460-21-9. Chemspider uses both. I could have attached a load more but vast majority (all) use 68460-21-9. Cargill I dont have a link too - but I have their SDS in front of me right now and it uses 68460-21-9 and their TDS matches with three oxirane rings. The same is true of Arnette Polymers with their RX44 product who also use 68460-21-9. I also googled 68460-21-9 and it comes up with TMETGE.

• TME Sigma-Aldrich
• TME Chemblink
• TME Chemspider
• TME Chemnet
• TME SRC
• TME REACH Europe

GRALISTAIR (talk) 13:56, 18 May 2022 (UTC)

References

Using those links, the -9 substance appears to be identified as I said, for example, REACH: "1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)-, polymer with 2-(chloromethyl)oxirane". Chemsrc even states it's a "1:1" combination of the triol and epichlorohydrin. We have to be careful to avoid echo-chamber among databases, especially given how poorly a common token like SMILES and InChI is for mixtures or polymers. CAS is the authority on CASNos. DMacks (talk) 14:17, 18 May 2022 (UTC)

https://commonchemistry.cas.org/results?q=36366-26-4 shows no results GRALISTAIR (talk) 14:54, 18 May 2022 (UTC)

https://commonchemistry.cas.org/results?q=68460-21-9 but 68460-21-9 does GRALISTAIR (talk) 14:56, 18 May 2022 (UTC)

http://www.chemspider.com/Chemical-Structure.2666788.html shows 68460-21-9 with the correct structure too GRALISTAIR (talk) 14:58, 18 May 2022 (UTC)

That -9 entry explicitly states "1,3-Propanediol, 2-(hydroxymethyl)-2-methyl-, polymer with 2-(chloromethyl)oxirane" and does not say it is the exact 1:3 TMETGE unit. That's what I've said three times now. And it says the molecular formula is "(C5H12O3.C3H5ClO)x", which again is not consistent with what you would want. Commonchemistry contains less than 1% of all CASNos. DMacks (talk) 09:54, 19 May 2022 (UTC)

Well in fairness I have read multiple times and full disclosure it is my job- for over 40 years. I understand the burden of Wikipedia standard of proof is on me but I think I now see where your misunderstanding is coming from. Let us take simple epoxy resin. There are usually 2 CAS numbers used in the industry. 25068-30-6 is one that is very often used. Look at page 12 of this document. If you look at the whole document though you will see the molecule drawn out and not a even a smell of a hydroxyl group - but -but -but - look at the description -- Phenol, 4,4'-(1-methylethylidene)bis-, polymer with (chloromethyl)oxirane - from that description you would think there are hydroxyl groups present and chlorine - but they are not. It is bad wording in the early days of TSCA and CAS. It was a way of using the word polymer to get round legislation etc. The European Union amended the rules in 1992 and now produce a No Longer Polymers List (attached for your reference).

However, you can argue the European Union confuse it even more- this is key. CAS Number: 25068-38-6 Molecular formula: (C15H16O2 . C3H5ClO)x IUPAC Name: 4,4'-Isopropylidenediphenol, oligomeric reaction products with 1-chloro-2,3-epoxypropane. Note in the formula and name they have hydroxyls and halogens - but look at the structure and no chlorine to be seen. This from Europe not bad either.

Anyway, I promise I will do the same exhaustive research for TMETGE. I will need to give you links where possible showing that some extremely reputable companies -Cargill ChemMod 44, Hexion Heloxy 44, Arnette Polymers RX44 and other all use 68460-21-9.

I am glad we are having this discussion and hope to reach consensus. At the moment I am refusing to pay money for CAS themselves to do the search and give a definitive answer.

Meanwhile an Australian SDS that has really been through the mill. Look in section 3 ingredients - again TMETGE is given CAS 68460-21-9 as does one in California

I typed into google the following exactly "trimethylolethane" triglycidyl ether CAS number and the absolute top hit and multiple more show 68460-21-9.

As I said, I will now try and get full SDS from 3 reputable independent respected sources to hopefully convince you. I don't want this to go to arbitration. GRALISTAIR (talk) 13:54, 19 May 2022 (UTC)

At least 1 Chinese source shows 68460-21-9 with the name TMETGE and the correct structure GRALISTAIR (talk) 15:37, 19 May 2022 (UTC)

Here is another really interesting page. Sadly it does not draw the structure but it shows the correct formula - but not a chlorine in sight. Look at the molecular weight - it balances perfectly with the stated formula -but not a chlorine in sight. If you calculated the MWt with chlorines in it would be way out of kilter. But the name has chlorine in - again it is the way CAS/TSCA were set up sadly. GRALISTAIR (talk) 16:01, 19 May 2022 (UTC)

One textbook I love and consider the bible on diluents and fillers etc is In particular check page 64 - where the information is presented again showing the CAS number 68460-21-9 GRALISTAIR (talk) 16:04, 19 May 2022 (UTC)

Here is another excellent example. Fortunately in this case they show the correct structure and namebut also show chlorine and other atoms. ChemSRC is again the culprit. GRALISTAIR (talk) 21:09, 23 May 2022 (UTC)