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Author: Subject: Peroxy Aldehydes ?
franklyn
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[*] posted on 30-7-2006 at 01:02
Peroxy Aldehydes ?




The Ketone, Acetone CH3COCH3 forms into this cyclic ring peroxide compound

shown above. It does not however polymerize with it's carbonyl alone to form

into such a ring arrangement. It seems that the methyl groups present to much

bulk for this form to occur without the added length of the peroxide bonding.


The Aldehyde, Acetaldehyde CH3CHO with one less methyl group does polymerize

to form the cyclic ring Paraldehyde shown above. Acetaldehyde will spontaneously

form peroxides on it's own when exposed to air and the ultraviolet light present

in sunlight.


The base form Aldehyde, Formaldehyde CH2O readily polymerizes wether you like it

or not and it is a challenge to prevent this from happening. This forms into chain

Paraformaldehyde but also into the cyclic form Trioxane shown above.


Peroxy compounds of these latter precursors acetaldehyde and formaldehyde should

form as easily if not more so than the more familiar " Mother of Satan " TATP.

TATP evolves 6 moles of gas ( ? ) however the peroxy analog of Paraldehyde could

evolve 12 moles though with a better oxygen balance. ( CH3CHOO )3 -> 6CO + 6H2 ,

A peroxy trioxane would again only be 6 moles with the best oxygen balance.


Related links

http://www.itt.uni-stuttgart.de/pdfs/2004_gruetzner_jced.pdf

Quote:
Originally posted by madscientist posted on 21-5-2002 at 02:34 PM

I am thinking that it would be possible to form aceteldehyde peroxide and / or formaldehyde peroxide

http://www.sciencemadness.org/talk/viewthread.php?tid=24#pid...

http://www.sciencemadness.org/talk/viewthread.php?tid=33#pid...
http://www.sciencemadness.org/library/methyl_ethyl_ketone_pe...
http://www.sciencemadness.org/talk/viewthread.php?tid=4719#p...

.

[Edited on 4-10-2007 by franklyn]
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The_Davster
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[*] posted on 30-7-2006 at 07:12


The last person to attempt 'formaldehyde peroxide', Dimethylol peroxide was Axt. It blew a hole in his table..
https://sciencemadness.org/talk/viewthread.php?tid=2574




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Nerro
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[*] posted on 30-7-2006 at 07:48


TATP evolves 4 molecules of gas because it forms three acetone molecules and one molecule of ozone. That, at least is what the only study I ever read on this topic said. The energy of the blast is caused by the sudden increase in entropy apparently.

My point is you cant jsut bluntly assume that CO2 and H2O will be the only products of detonation. It is actually quite likely that that isn't what is formed at all.




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franklyn
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[*] posted on 30-7-2006 at 10:32


Quote:
Originally posted by rogue chemist
'formaldehyde peroxide', blew a hole in his table..
https://sciencemadness.org/talk/viewthread.php?tid=2574

The road to wisdom is perilous, all the more reason

to climb a mountain to speak to a pundit.


Quote:
Originally posted by Nerro
TATP evolves 4 molecules of gas

Yes I read that in wiki , however I didn't understand

it as it does not specify products.
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franklyn
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[*] posted on 6-8-2006 at 03:36


I'm thinking that given that Acetic acid readily forms Peracetic acid,
the ester of Acetic acid and Methanol, Methylacetate,
may form a peroxy trimer as well:
C9H18O9. TrimethylacetateTriperoxide.
Better oxygen balance should promote complete
disarrangement yielding 18 moles of gas , 9CO + 9H2




[Edited on 6-8-2006 by franklyn]
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franklyn
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[*] posted on 11-8-2006 at 08:39


Update
Does anyone know if C2H4O Ethylene oxide , or even C2H2O Acetylene oxide
are candidates for Peroxidation ? It seems that these being gases , reaction
could take place on the liquid surface of the peroxide acid reagents to form
dimers or trimers.

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12AX7
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[*] posted on 11-8-2006 at 13:23


Three oxygens on a carbon? I'd like to see that!

Carbonate ion has a resonance structure, and organic carbonate has one double-bonded. AFAIK, three single-bonded oxygens can't happen. At least I've never seen it.

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not_important
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[*] posted on 11-8-2006 at 13:26


Look up "ortho esters", such as HC(OMe)3 - three single bonds to oxygens on one carbon.
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Chris The Great
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[*] posted on 11-8-2006 at 17:49


Ozonides do form the 3-oxygen ring but are extremely unstable. Ozonides are formed by the low temperature reaction between a double carbon-carbon bond and ozone.

Quite simple except that the end products are extremely sensitive, some to mere touch, and yet have more explosive power than nitroglycerin in some cases.
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JohnWW
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[*] posted on 13-8-2006 at 01:25


I heard that acetone peroxide was what those Muslim suicide bombers recently arrested in England were going to use to bring down 9 or 10 trans-Atlantic planes. Apparently they were going to go onto each plane in trios, one carrying acetone in a drinks bottle, another carrying concentrated hydrogen peroxide similarly disguised, and the third carrying a radio or something similar containing a 9-volt battery, with wires, with which to generate sparks to ignite the acetone peroxide solution in acetone. The mixing of the acetone and hydrogen peroxide was to be done in-flight, just before they were to blow the planes up.
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franklyn
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[*] posted on 13-8-2006 at 17:02


Stories put out by media talking heads , lead on by cagey official spokesmen are
just that , stories. That a binary liquid explosive was to be used is not in doubt.
Perhaps acetone and HI TEST Hydrogen Peroxide mixed. With the two combined,
the only detonator you would need is to drop it on the floor. Compounding, to
produce TATP , I am sure those here with personal know how will concur , cannot
be acheived as described in the circumstances and time available. The phone setup
was so that all the aircraft could be simulataneously fulminated on a given signal,
thus precluding air crews and sky marshals from intervening when alerted by ground
control to take precautions.

[Edited on 14-8-2006 by franklyn]
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not_important
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[*] posted on 13-8-2006 at 20:05


Some reports have been stating it was to be HMTD, I assume with the HMTA in water or as a mush that could pass as a gel. Still has a problem with the time needed.

On the other hand, I doubt the airport sensors would pick up on the organic peroxides. Might be possible to mix it up before the flight, long enough to let product form, keep it cool, colour it with a bit of dye, and would look like sports drinks. Couldn't taste worse than some sports drinks, so it could even be sipped to show it was safe.

There may be reasons that wouldn't work, I'm sure there are folks here that could provide corrections a needed.
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Axt
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[*] posted on 22-8-2006 at 03:33


Aldehydes tend to stop at the soluble hydroperoxides when formed in aqueous solution, dehydration is needed to form cyclic or polymeric peroxides.

Attached is an article on some peroxidic derivatives of acetaldehyde, I dont know what it says 'cause 'tis in german and havn't tried to read it.

Attachment: Peroxide derivatives of Acetaldehyde - AngChem,66,633-635 (1954).pdf (599kB)
This file has been downloaded 716 times

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franklyn
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[*] posted on 28-8-2006 at 19:36


Quote:
Originally posted by not_important

I doubt the airport sensors would pick up on the organic peroxides.
http://www.exchangemonitor.com/news_flash.htm
Quote:
Originally posted by Axt

Aldehydes tend to stop at the soluble hydroperoxides when formed in aqueous solution,
dehydration is needed to form cyclic or polymeric peroxides.
That explains why these compounds are not seen. Its not worth the trouble.

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not_important
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[*] posted on 28-8-2006 at 21:33


Quote:
“If they were using nitroglycerin, liquid nitroglycerin, probably could have been detected. If they were trying for some of the less powerful explosives that you can get from mixing household chemicals, then we probably wouldn’t have detected it.” James Lewis, director and senior fellow of the Technology and Public Policy Program at the Center for Strategic and International Studies, told HD&S Monitor.


Later on there's some TSA snerd going on about nitroglycerin and how "all these explosives are alike at the microscopic level"; somehow peroxides and nitrate esters seem somewhat different to me. I suspect smoke blowing from some hack trying to look effective.

Of course, once there are next gen explosives detectors in place, Osama's merry lads will take to making low grade nitrate esters and aromatic nitrates, putting a bit into gelatin capsules or diluted into perfume spritz bottles, and going to airports where they drop the capsules onto walkways and spritz people and luggage headed for checkin. Each time someone sets off a sensor, the airport shuts down, and the bad guy is not even near.
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Axt
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[*] posted on 1-9-2006 at 08:10


Quote:
Originally posted by franklyn
Its not worth the trouble.


Not of much use to a kewl/terrorist, but for example the dimeric peroxide of acetaldehyde, its properties exceed acetone peroxide by a substantial amount.

<center><table border=1 bordercolor="777zzz" cellspacing=5 cellpadding=0 style=border-collapse:collapse;border:none' style="font-size:13px"><tr><td></td><td>Pb Block</td><td>Density</td><td>VOD</td><td>%OB</td></tr><tr><td>Acetaldehyde Peroxide</td><td>330</td><td>1.451</td><td>?</td><td>-106.56</td></tr><tr><td> Acetone Peroxide</td><td>250</td><td>1.2</td><td>5300 @ 1.18</td><td>-151.17</td></tr></table></center>

The dehydration product of dimethylol peroxide would also be nice, O=(CH2-O-O-CH2)2=O (imagine structure of HMTD with N's replaced with O's).

I'll attach another, on formaldehyde/acetaldehyde peroxides, again in german. Think I got it from Annalen der Chemie.

[Edited on 1-9-2006 by Axt]

Attachment: aldehyde peroxides.pdf (2.5MB)
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franklyn
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[*] posted on 1-9-2006 at 16:45


It is only of interest to those who care about the technical preparation and synthesis
of high explosive compounds. I had surmised that re-dox combustion would
improve the properties beyond that of entropic disassociation alone.

" The dehydration product of dimethylol peroxide would also be nice "
Now I know where you're going with this. Lets hope it doesn't get mad and
perforate your table top again.

.
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franklyn
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[*] posted on 18-4-2007 at 05:22


No , not exactly a ketone , but any ideas if this might be peroxide crosslinked ?





http://en.wikipedia.org/wiki/TAED

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[*] posted on 14-7-2013 at 21:37


Mixtures of hydrogen peroxide with aldehydes are much less chemically stable than with ketones:

Quote: Originally posted by KABOOOM(pyrojustforfun)  
HCHO + H<SUB>2</SUB>O &nbsp;&nbsp;&nbsp;qe&nbsp;&nbsp;&nbsp;H<SUB>2</SUB>C(OH)<SUB>2</SUB>
Formaldehyde peroxidation
H<SUB>2</SUB>O<SUB>2</SUB> + H<SUB>2</SUB>C(OH)<SUB>2</SUB>&nbsp;&nbsp;&nbsp;qe&nbsp;&nbsp;&nbsp;HOCH<SUB>2</SUB>OOH + H<SUB>2</SUB>O
HOCH<SUB>2</SUB>OOH + H<SUB>2</SUB>C(OH)<SUB>2</SUB>&nbsp;&nbsp;&nbsp;qe&nbsp;&nbsp;&nbsp;HOCH<SUB>2</SUB>OOCH&l t;SUB>2</SUB>OH + H<SUB>2</SUB>O

One approach was to use another difunctional peroxide that those already in use (hydrogen and adipoyl peroxides were already patented). I looked at some texts and noted one could make an aldol peroxide from formaldehyde and hydrogen peroxide. I put together some concentration variations of butadiene, isopropanol, formaldehyde, and hydrogen peroxide, to make the initiator in- situ. We set them up in the standard sealed polymerization bottles at 75 degrees Centigrade. Nothing happened for about two hours, and I looked in one them hourly. Just after the 2nd hour inspection, I went back to my desk for coffee, and one of the technicians raced up saying "Did you hear the explosion?". I hadn't, but went with him to the polymerization lab external door just in time to hear another one "cook off".
The lab was cleared of all personnel already, and one just barely missed being inundated by the 75 degree water as the first explosion went off. I put on face mask and rubber apron and crawled into the lab to turn off the steam and fill the bath with cold water. The lab floor was littered with sand sized glass particles, and one of the polymerization bottle guards was about 15 feet from the polymerization bath. After about a half hour of cooling, I donned apron, long gloves and face mask, and took out all the remaining bottles, and emptied those that still were intact- not many. The force of the explosion ripped the stainless caps off some of the bottle shields, and one of those shields remains on my desk to remind me I'm fallible.
This was the last day before my vacation was to start, so when I left after cleaning up, I was gone for at least a week. When I got back, I found that there had been an inquiry. Gerd Lenke had been assigned top look into the matter, and he found an ancient Gmelian book set which showed details of the formaldehyde/hydrogen peroxide products. The one I wanted (and probably got) was dimethylol peroxide, which melts about 60 degrees C, and is a "brisant" explosive at 72 degrees. It would not have detonated at 70 degrees, but I was five degrees higher. I still think it would be a good di-functional initiator, BUT...Handle With Care!


Essentially the reaction between H2O2 and CH2O apparently can potentially be dangerous.

For further discussion on the potential reaction between hydrogen peroxide and formaldehyde, see:
http://www.sciencemadness.org/talk/viewthread.php?tid=18169#...


Quote: Originally posted by madscientist  
I am thinking that it would be possible to form aceteldehyde peroxide and / or formaldehyde peroxide

It may be possible. The peroxide of acetaldehyde certainly exists, though I am not sure if it can be made from acetaldehyde and H2O2. They may be very unstable though.

[Edited on 15-7-2013 by AndersHoveland]
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