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Topic: Co2 converion to cyclic carbonates  (Read 3712 times)

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Offline bisilara

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Co2 converion to cyclic carbonates
« on: December 05, 2016, 04:55:23 AM »
I am a new PhD student in Chemical engineering  working on heterogeneous catalytic conversion of co2 to value added chemicals  with special focus on cycloaddition reaction of   co2 and Epichlorohydrin to produce Epichlorohydrin carbonate   (Please note that  Pure sample of Epichlorohydrin carbonate is not available from any chemical company for a standard calibration to guide my own product). From my literature review,  I come to understand that Epichlorohydrin carbonate has other names such as: Chloropropylene carbonate/ chloroprene carbonate etc. My problem and my question is:

 1) Is  Epichlorohydrin carbonate the same as  Chloromethyl ethylene carbonate?
(because Chloromethyl ethylene carbonate has a pure sample.  If they are the  same,  then I can use Chloromethyl ethylene carbonate  for calibration instead of unavailable Epichlorohydrin carbonate)     

2) If they are not the same, can I produce my own Epichlorohydrin carbonate and calibrate it? how can I do this? I am really stuck! any help at all will worth more than a gold 

Thank you in advance

Offline sjb

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Offline kriggy

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Re: Co2 converion to cyclic carbonates
« Reply #2 on: December 05, 2016, 05:24:11 AM »
I somehow fail to see how the 6 membered compound could be called epichlorhydrine carbonate. Maybe it would be helpful, if OP posted the structure he/she wants to make and then we can talk


Offline bisilara

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Re: Co2 converion to cyclic carbonates
« Reply #3 on: December 05, 2016, 06:07:47 AM »
@ Sjb, thank you, I don't think the 2 structures are the same. so Epichlorohydrin carbonate is definitely not the same  as Chloromethyl ethylene carbonate. Ok, how then do I calibrate Epichlorohydrin carbonate to be used as a pretend pure standard for my experiment?

Thank you   

Offline bisilara

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Re: Co2 converion to cyclic carbonates
« Reply #4 on: December 05, 2016, 06:11:02 AM »
I somehow fail to see how the 6 membered compound could be called epichlorhydrine carbonate. Maybe it would be helpful, if OP posted the structure he/she wants to make and then we can talk



I looked at the link but it doesn't give me an English explanation of anything...pls pardon me, I only peak english   

Offline sjb

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Re: Co2 converion to cyclic carbonates
« Reply #5 on: December 05, 2016, 06:51:30 AM »
@ Sjb, thank you, I don't think the 2 structures are the same. so Epichlorohydrin carbonate is definitely not the same  as Chloromethyl ethylene carbonate. Ok, how then do I calibrate Epichlorohydrin carbonate to be used as a pretend pure standard for my experiment?

Thank you

Assuming the structures are right, then these are isomers and have the same MW but are likely to have different retention times in HPLC, for instance. How are you planning on showing that you have formed product?

Offline bisilara

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Re: Co2 converion to cyclic carbonates
« Reply #6 on: December 05, 2016, 07:33:05 AM »
@ Sjb, thank you, I don't think the 2 structures are the same. so Epichlorohydrin carbonate is definitely not the same  as Chloromethyl ethylene carbonate. Ok, how then do I calibrate Epichlorohydrin carbonate to be used as a pretend pure standard for my experiment?

Thank you

Assuming the structures are right, then these are isomers and have the same MW but are likely to have different retention times in HPLC, for instance. How are you planning on showing that you have formed product?


This is interesting, like I mentioned, I have only just  had one month through my studies, I haven't thought about the performance of individual products   in GC analysis. But I think this is the more reason I need to get a pure sample to work with. Another literature I have seen  has used both Epichlorohydrin carbonate as a synonym of Chloromethyl ethylene carbonate. Product performance in GC is another phase of my studies I'm  planning in the new year     

Online mjc123

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Re: Co2 converion to cyclic carbonates
« Reply #7 on: December 05, 2016, 08:06:05 AM »
Like kriggy, it makes no sense to me that the 6-membered ring should be called epichlorohydrin carbonate, as it is not structurally related to epichlorohydrin. A quick google suggests that, as might be expected, CO2 reacts with epoxides (including epichlorohydrin) to give 1,2-carbonates. I'm sure that is what OP is doing and, if so, their "epichlorohydrin carbonate" must be the same as chloromethyl ethylene carbonate.

Offline sjb

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Re: Co2 converion to cyclic carbonates
« Reply #8 on: December 05, 2016, 10:45:07 AM »
Hmm, further searching around reveals http://www.chemindustry.com/chemicals/02287747.html - maybe the pubmed link is incorrect. Sorry for leading down a blind alley.

Offline bisilara

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Re: Co2 converion to cyclic carbonates
« Reply #9 on: December 05, 2016, 12:14:58 PM »
Hmm, further searching around reveals http://www.chemindustry.com/chemicals/02287747.html - maybe the pubmed link is incorrect. Sorry for leading down a blind alley.



That's ok, you're only trying to help. The link below shows that Epichlorohydrin carbonate is used interchangeably Chloromethyl  ethylene carbonate both having the same MW. This is really doing my heading

 1) http://www.chemindustry.com/chemicals/0427142.html

2) http://www.guidechem.com/reference/dic-59020.html

3) http://www.lookchem.com/Carbonic-acid-cyclic-3-chloropropylene-ester/


3) http://www.lookchem.com/Carbonic-acid-cyclic-3-chloropropylene-ester/



Offline AWK

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Re: Co2 converion to cyclic carbonates
« Reply #10 on: December 05, 2016, 07:19:55 PM »
You use commercial names. They may be ambiguous sometimes.
Quote
both having the same MW
Almost 200 years organic chemists know isomers.
AWK

Offline bisilara

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Re: Co2 converion to cyclic carbonates
« Reply #11 on: December 05, 2016, 10:07:57 PM »
You use commercial names. They may be ambiguous sometimes.
Quote
both having the same MW
Almost 200 years organic chemists know isomers.

Thank you for your reply, going forward, are these 2 compounds the same or not? Epichlorohydrin carbonate & Chloromethyl ethylene carbonate

Thank you

Online Borek

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Re: Co2 converion to cyclic carbonates
« Reply #12 on: December 06, 2016, 02:46:38 AM »
are these 2 compounds the same or not? Epichlorohydrin carbonate & Chloromethyl ethylene carbonate

As AWK told you, commercial names are ambiguous and are not guaranteed to be accurate. It may even happen that different companies use the same name for different compounds. So it is not possible to answer your query, as the only viable answer is: they can be the same, they can be not the same.

The only way to check is to use correct IUPAC names and to contact the company producing samples, asking them for clarification about structure.
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