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RE: ORGLIST glycerol diglycidyl ether

From: "Ilya Avrutov" <IAvrutov>
Subject: RE: ORGLIST glycerol diglycidyl ether
Date: Tue, 12 Jul 2011 09:16:04 -0400
Hi Neil,
 
One of the refernces is Japanese patent (JP,63115877) but you could try use the procedure from its abstract:

 

Title ethers, useful as diluents for epoxy resins, are purified by neutralizing crude H2O-sol. glycidyl ethers, prepd. from glycols or glycerins, with excess H3PO4 till pH in 50% aq. soln. reaches 4-4.5 followed by treatment with acid adsorbents. Treatment of diethylene glycol with epichlorohydrin in the presence of Et2O.BF3 at 30-50 gave a chlorohydrin ether, to which aq. NaOH was added dropwise at 20-30 over 30 min to give crude diethylene glycol diglycidyl ether (I). I was stirred with an aq. H3PO4 at 75 for 1 h and the resulting cloudy mixt. was treated with Kyowaad 500SH [Mg6Al2(OH)16CO3.4H2O] (II) at 75 for 1 h to give I free of Na, which showed pH 7.1 (in 50% aq. soln.), WPE (wt. per epoxide) 149, and viscosity 23.0 cP, vs. 6.5, 149, and 23.0 cP., resp., for a control without treatment with II. After 6 mo. storage, I showed pH 7.3, WPE 152, and viscosity 23.2 cP, vs. 9.3, 158., and 24.4, resp., for the control, in which formation of gel was obsd. on a test piece.

 

And in this reference (Azerbaidzhanskii Khimicheskii Zhurnal (2006), (2), 127-131) formation of mono-, di- and tri-ethers of glycerin with epichlorohydrine are described (after dehydrogalogenation they will give appropriate glycidyl ethers). Here is the abstract:

Condensation of propanetriol (PT) with epichlorohydrin (ECH) was studied. The reaction proceeds with sequential formation mono-, di- and tri-ethers of PT. Reactivity of hydroxy groups of PT in the reaction with ECH is by 4.5 order of magnitude higher than that of triether of PT. Changing the reaction conditions the reaction can be directed towards the formation of mono-, di- and trichlorohydrines. Three-ray oligomers and its three-epoxides with different content of chlorine atoms in lateral chain were synthesized.

 It looks, that they have procedure description in the article. Try to get the paper.

Best,

Ilya

 

Ilya Avrutov, PhD
Process Development Team Leader
Dalton Pharma Services
349 Wildcat Rd., Toronto, ON
M3J 2S3 Canada

 

 


From: orglist-everybody [mailto:orglist-everybody] On Behalf Of Neil Trout
Sent: Tuesday, July 12, 2011 7:55 AM
To: orglist-everybody
Subject: ORGLIST glycerol diglycidyl ether

Dear all,
 
I'm having trouble finding a prep for glycerol diglycidyl ether. It is commercially available
but 3 weeks away and I need a prep. so I can start. Has anyone made this before or have a reliable
reference for this compound,
 
Thanks in advance,
Cheers,
Neil
 
 
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