User
Hazard to Others
Posts: 339
Registered: 7-11-2008
Location: Earth
Member Is Offline
Mood: Passionate
|
|
Ideas on forming diethylene glycol
Hello, mad scientists.
Has anyone any ideas on forming diethylene glycol from commonly available materials.
Can it be done from ethylene glycol or other simple glycols?
Any help would be much appreciated.
Greetings user.
|
|
|
Sauron
International Hazard
Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline
Mood: metastable
|
|
Djethylene glycol is also a commercially available and common solvent expecially for higher temperature reactions. AFAIK it is not under any
restrictions. If you wanted many tons, the CWC folks might ask a few questions, because it is a precursor to the oxygen analog of mustard.
HO-CH2CH2-O-CH2CH2-OH doethylene glycol, or properly bis(2-hydroxyethyl)ether
Replace those hydroxyls with chlorine and you have bis (2-chloroethyl)ether, or O-mustard, which has been used as an industrial solvent but is now
classed as a chemical weapon under CWC and I believe as an OSHA carcinogen as well. It is a vesicant (blister agent) similar to but less potent than
"mustard" or Agent HD.
So, given that diethylene glycol is an industrial chemical, why is it that you seem to think it is necessary to make your own?
It is an ether and is made much like any other ether, which is not very arcane at all.
Unlike thiodiglycol, diethylene glycol is not on any CWC schedule except as a precursor, I think on Schedule 2 or 3, and its small quantity
distribution is not curtailed.
But the way you approach us with your question rather makes me wish it were.
If you were to ask us how to make thiodiglycol, well, I doubt anyone would help you. Chemical Ali is awaiting executiuon for using what his forces
made out of THAT.
All in all I would advise the members to refrain from assisting someone this clueless about something with this sort of potential. You seem not to be
a chemist or you wouldn't have to ask whether or not DEG can be made from EG and how.
Sic gorgeamus a los subjectatus nunc.
|
|
|
sparkgap
International Hazard
Posts: 1234
Registered: 16-1-2005
Location: not where you think
Member Is Offline
Mood: chaotropic
|
|
In any case, oxirane, which is the easiest precursor to DEG and higher homologues, ain't a walk in the park either. 
sparky (~_~)
"What's UTFSE? I keep hearing about it, but I can't be arsed to search for the answer..."
|
|
|
User
Hazard to Others
Posts: 339
Registered: 7-11-2008
Location: Earth
Member Is Offline
Mood: Passionate
|
|
Well no i don't have much insight in this division of chemistry.
Although i have had 2 years of chemistry related education.
I posses i quite well equipped lab and a wide variate of chemicals, I am not really a newbee.
I am just very interested in the formation of this chemical, just curiosity.
I have done an internet search but this isn't offering much use full info.
So that is why I am posing this question.
I hope i've made the reason for asking clear and showing my good intention.
I know it isn't restricted, that does not mean it has to be more expensive to form it yourself.
Most of it's brothers and sister have commercial applications such as anti freeze etc. I don't have to tell you that 
It is possible that i haven't searched thoroughly enough but I didn't find it in regular stores.
[Edited on 14-3-2009 by User]
|
|
|
Sauron
International Hazard
Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline
Mood: metastable
|
|
When something is a cheap chemical commodity it rarely pays to make your own.
This stuff is $15-$20 a liter in packjaging of 1 to 10 liters. I see no point in preparing something this cheap.
There are much better chemistry resources on and off the Net than Google.
And sparkgap's point is well taken. Oxirane is the key, and it is nasty. If you are unfamiliar with the name, try ethylene oxide. A gas. Is your well
equipped lab outfitted with a fume hood rated for carcinogens? Have an SCBA handy?
[Edited on 14-3-2009 by Sauron]
Sic gorgeamus a los subjectatus nunc.
|
|
|
User
Hazard to Others
Posts: 339
Registered: 7-11-2008
Location: Earth
Member Is Offline
Mood: Passionate
|
|
Well i have looked up some information in one of my old organic chemistry books, so it might not be fully up-to-date.
And sure isn't an easy process especially the presence of ethylene oxide.
Does anyone know of any other method ?
Sorry for the raw picture, i should get a scanner.
[Edited on 14-3-2009 by User]
|
|
|
BromicAcid
International Hazard
Posts: 3228
Registered: 13-7-2003
Location: Wisconsin
Member Is Offline
Mood: Rock n' Roll
|
|
Although I hardly ever agree with Sauron that it doesn't pay to make a chemical on your own, diethylene glycol can be a pain in the butt to make at
home. Please check the household products database:
http://hpd.nlm.nih.gov/index.htm
Search for products containing diethylene glycol, there are a few with >10% diethyene glycol that could potentially be fractioned to get your
desired product. Some time back I was looking for triethylene glycol and happened across a >95% source OTC. It is a useful database.
|
|
|
User
Hazard to Others
Posts: 339
Registered: 7-11-2008
Location: Earth
Member Is Offline
Mood: Passionate
|
|
Thats a very usefull link.
Thank you.
|
|
|
BromicAcid
International Hazard
Posts: 3228
Registered: 13-7-2003
Location: Wisconsin
Member Is Offline
Mood: Rock n' Roll
|
|
If you really wanted to give it a shot I was bumbling around with the idea of making 1,4-dioxane from ethylene glycol (Frogfort has a good procedure
for this) then ring opening that product using HBr or potentially HCl, relying on a small amount of ring straing to open the ring preferably rather
than cleaving the given bromohydroxy ether, and finally reacting that product with aqueous base to hydrolyze the bromo or other halo group to the
hydroxyl giving your desired product. A little bit of a round-about way of getting to this but it was something that I was pondering.
|
|
|
Paddywhacker
Hazard to Others
Posts: 478
Registered: 28-2-2009
Member Is Offline
Mood: No Mood
|
|
More kudos would be given if you asked about making crown ethers from ethylene glycol.
|
|
|
Sauron
International Hazard
Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline
Mood: metastable
|
|
BromicAcid, do you really want this clueless fellow to play with p-dioxane? For starters it is nasty shit and for the finishing touch it is a LOT more
expensive that DEG itself so making DEG out of it is very uneconomically sensible.
The health and safety risks should rule. I really doubt User has a hood.
When User sees the price of 1,4-dioxane, he'll be back here asking how to make THAT. At least there's a good prep from EG in J Ed Chem that has been
posted before I believe.
Of course he should cut out the middleman and just make the DEG - it's a lot less hazardous than dioxane unless he tries to do a chlorination in it.
Sic gorgeamus a los subjectatus nunc.
|
|
|
Paddywhacker
Hazard to Others
Posts: 478
Registered: 28-2-2009
Member Is Offline
Mood: No Mood
|
|
What is the problem with 1,4-dioxane, Sauron? I always fancied getting some as a potential higher boiling substitute to Et2O for making Grignards.
|
|
|
Sauron
International Hazard
Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline
Mood: metastable
|
|
It's a serious suspected carcinogen and also a much worse peroxide former than Et2O,
Have a look in Sax, etc.
Also
http://www.epa.gov/ttn/uatw/hlthef/dioxane.html
[Edited on 15-3-2009 by Sauron]
Sic gorgeamus a los subjectatus nunc.
|
|
|
Ebao-lu
Unregistered
Posts: N/A
Registered: N/A
Member Is Offline
|
|
and do the oligoethyleneglycols form peroxides?
|
|
|
Sauron
International Hazard
Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline
Mood: metastable
|
|
I do not know. Not that I am aware, at least not readily. But dioxane has that rep, almost as bad as di-isopropyl ether.
Sic gorgeamus a los subjectatus nunc.
|
|
|
JohnWW
International Hazard
Posts: 2849
Registered: 27-7-2004
Location: New Zealand
Member Is Offline
Mood: No Mood
|
|
1,4-dioxane? When I was in an organic chemistry laboratory class about 40 years ago, I used to sniff the stuff! It is used in organic chemistry, and
also biochemistry, because it dissolves a large range of substances, and is miscible in all proportions with water and ethanol and diethyl ether.
|
|
|
Sauron
International Hazard
Posts: 5351
Registered: 22-12-2006
Location: Barad-Dur, Mordor
Member Is Offline
Mood: metastable
|
|
Did I say it wasn't useful?
I said, if you read the reference, that is causes tumors in orally exposed test animals, so it is a proven animal carcinogen, and a strongly suspected
human carcinogen and classified as such ab the US EPA and probably OSHA.
On that basis, I would caution anyone contemplating its use to use a good fume hood and wear appropriate protective garments and equipment just as you
would with benzene and other materials in the same category.
And since the fellow asking about DEG prep sounds clueless I advised BromicAcid that perhaps p-dioxane was not a suitable reagent for someone that wet
behind the ears.
And I would advise against sniffing it any more.
Sic gorgeamus a los subjectatus nunc.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
