Farnsworth
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A quick contribution: Diethylene Glycol
I've been pouring over stacks of MSDS sheets looking for a new sources for chemicals in my local area. I know there have been some threads in the
past on extracting pure DEG from antifreeze.
Coghlan's Camp Heat is a small portable chemical heating pot available at Dick's Sporting Goods stores, Sears, and some Wal Marts. MSDS pegs the
contents as 100% diethylene glycol. A 2 pack runs about seven bucks.
http://www.coghlans.com/files/0450-Camp-Heat.pdf
http://www.sears.com/shc/s/p_10153_12605_SPM2673766901P?sid=...
[fixed bad link]
[Edited on 19-5-2012 by Farnsworth]
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Magpie
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Thanks for posting this - it will likely come in handy at some point in time.
The single most important condition for a successful synthesis is good mixing - Nicodem
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Magpie
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For those anticipating a need for this compound it would be a good time to place your order for Coghlan's 0450 Camp Heat. According to Amazon it is
being discontinued by the manufacturer.
The single most important condition for a successful synthesis is good mixing - Nicodem
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UC235
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Coghlans is far from the only company selling this type of product, and you are vastly overpaying by buying from them.
It's sold at Sams Club (http://www.samsclub.com/sams/bakers-chefs-safe-heat-12-pk/17...), restaurant industry suppliers (such as http://www.webstaurantstore.com/2603/chafing-dish-fuel.html, any of the "wick" cans) and even on amazon (http://www.amazon.com/Bakers-Chefs-Safe-Heat-9-24/dp/B00255V...)
The 6hr case of 24 from Webstaurant provides 4.7L of DEG for $26.49 plus shipping. If you need a fuckton of 1,4-dioxane, you're in luck!
[Edited on 8-7-2015 by UC235]
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Magpie
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Thank you for this! I thought that chafing dish fuel was a Sterno type, ie, made from ethanol or methanol. I see now that it also can be made from
DEG.
It is also useful to know that dioxane can be made from DEG by dehydration. Have you done this?
The single most important condition for a successful synthesis is good mixing - Nicodem
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UC235
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Quote: Originally posted by Magpie  | Thank you for this! I thought that chafing dish fuel was a Sterno type, ie, made from ethanol or methanol. I see now that it also can be made from
DEG.
It is also useful to know that dioxane can be made from DEG by dehydration. Have you done this? |
Yes, dioxane from DEG is an extremely easy prep. Just mix a few ml of conc. H2SO4 into a few hundred ml and distill slowly. 1,4-dioxane boils at 101C,
and its azeotrope containing 18% water boils at 88C. DEG boils at 244C. You'll be left with some tarry black stuff that can probably be topped up with
more DEG for another run.
I've run a dioxane prep using the waste product from vacuum distilling ethylene glycol from super tech (cheap walmart brand) antifreeze concentrate.
It was a mix of EG, DEG, dye, and some assorted fatty acid salts. It proceeded smoothly as well.
The biggest problem I've had with 1,4-dioxane is drying it. Holy crap. Fractionating the azeotrope out is impossible given the 12C temp difference.
Melting sodium metal in it for hours until fizzing appeared to stop still yielded azeotrope on distillation. It also cannot be used for grignards as
far as I know, as the molecule chelates magnesium halides and precipitates them forming diorganomagnesium species in solution.
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Magpie
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Here's a video of a guy making dioxane from ethylene glycol anti-freeze. He's using NaOH for drying but does not quantify his purity.
I'm amazed that he was doing this with the garage door open for all to see. One comment addresses that.
https://www.youtube.com/watch?v=RfQGwleIA8E
At 2:53 he gives a quick shot of his large flasks sitting out on the driveway! 
[Edited on 9-7-2015 by Magpie]
The single most important condition for a successful synthesis is good mixing - Nicodem
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UC235
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| Quote: Originally posted by UC235 |
The biggest problem I've had with 1,4-dioxane is drying it. Holy crap. Fractionating the azeotrope out is impossible given the 12C temp difference.
Melting sodium metal in it for hours until fizzing appeared to stop still yielded azeotrope on distillation. It also cannot be used for grignards as
far as I know, as the molecule chelates magnesium halides and precipitates them forming diorganomagnesium species in solution. |
I would like to issue a correction to my above statement. The dioxane was most definitely dry when I distilled it. The contaminant was not water,
forming the azeotrope boiling at 87C as I thought, but a considerable amount of 2-methyl-1,3-dioxolane (acetaldehyde ethylene glycol acetal) that is
formed as a byproduct. This boils at 82-83C and I obtained a large mixed boiling fraction (in the upper 80s to 90s range) since I lack a fractionating
column with enough theoretical plates to cleanly separate 17C
I am currently working on a small prep of 1,4-dioxane. After the initial treatment with solid NaOH (which on long standing gives a precipitate of dark
tar and a clear yellowish supernatant), I added a portion of 50% aq. H2SO4 and allowed it to stand overnight. The liquid became a darker orange. On
addition of NaOH to neutralize the H2SO4, the liquid again became dark red/brown from aldol condensations of the freed acetaldehyde. Hopefully a
second drying with NaOH and distillation will yield a single fraction this time.
[Edited on 1-10-2015 by UC235]
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chemrox
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| Quote: Originally posted by Magpie |
I'm amazed that he was doing this with the garage door open for all to see. One comment addresses that.
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Why? Are you in England or something? A society under surveillance...
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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aga
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Bible: Mark 8:18
Those that have Eyes to See, let them Spy on their neighbours and make a fast $ on selling the Crazy Drug Lab Outbreak video to the media.
Mark 5:1
Jesus ! The madman just put the video on utoob for all the pigs to see for free !
(after which the posessed pigs ran into the sea, and drowned).
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