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Author: Subject: Diphoronepentaperoxide (DPPP)
ordenblitz
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[*] posted on 7-10-2005 at 19:38


I have begun the process of trying to solve some mysteries in this long and contentious saga.

The plan is:
1) Make the acetone + HCl precursor, divide the result in two parts.
2) Half will be fractionally distilled and the fractions tested in the FTIR as they come off. 3) The remainder will be used in the synthesis of the DPPP for further testing both against my current libraries and also compared to a sample of trimeric acetone peroxide that will be prepared for same.
4) Both the suspected DPPP and AP will be recrystalized in toluene and compared again.

My intentions were to do most of the work then post the results, however I have found some interesting things so far and decided to post them now.

I mixed the acetone and HCl according to the proportions suggested by Roscoe. I intended to get at the distillation the next day but was distracted by some pesky work so I had to let it sit for 2 more days. Due to the age, I decided to discard this batch and begin again. Upon opening the closed bottle the contents consisted of a viscous goo on the top and a slightly thinner fluid below. I separated the two portions and let the upper residue dry out to a thin plastic looking film in a few hours. This film was run on the FTIR using the MIR accessory and compared to the library.

It came up as an excellent match.....poly epichlorohydrin!
Ok this is interesting. I can see the first two steps of the possible reaction mechanism below, being very probable but the last seems to require a base to complete.

acetone + Cl ---> dichloroacetone
dichloroacetone + H2 ---> dichloropropanol
dichloropropanol + xOH ---> epichlorohydrin + xCl + H2O

Regardless, it was a very good IR spectra and I agree with Nicolet's conclusions.

This leads me to believe that dichloroacetone and not phorone is being produced in the initial reaction. I will continue further testing and post the results as they come in.

For those who were sick of this thread, I apologize for re-awaking the sleeping giant.
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[*] posted on 8-10-2005 at 08:05
Excellent!


This is great! Reliable analytical data is what we need.

So, please continue, because these are some unsuspected, yet interesting results.




One shouldn't accept or resort to the mutilation of science to appease the mentally impaired.
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[*] posted on 8-10-2005 at 18:24


Quote:
Originally posted by ordenblitz
This film was run on the FTIR using the MIR accessory and compared to the library.

Pardon me, but could you explain FTIR and MIR for those of us not in the know?


BTW, vulture, you used the wrong conjunction there. The results are interesting because they are unexpected, not despite that; thus, you need an 'and' rather than a 'yet'.

Just because English may not be one's first language, it's no excuse to molest its structure like that. You know, I go downtown Vancouver, and all these asians, half of them barely know a word of English; it's sickening. Immigration is run terribly wrong: they shouldn't let anyone in that doesn't know English. Rather than assimilating immigrants, Canada has a nation-destroying policy of supporting the creation of growing pieces of foreign nations on Canadian soil. Chinatown here really is a part of China. I've heard the Canadian government actually advertises in asian countries that Canada is one of the only Western nations that one can come to without having to learn English! As an immigrant myself, who has become a proud Canadian and loves the good language, I feel very justified in commenting on this.

[Edited on 9-10-2005 by Quince]




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ordenblitz
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[*] posted on 8-10-2005 at 19:19


Acetone + HCl precursor tests.

I prepared the precursor once again according to the method used by Roscoe using known good chemicals.
http://img217.imageshack.us/img217/2672/chems0rj.jpg

You can see that it had the required color. For some reason I expected it to be more viscous, but it met the general descriptions that were given.
http://img217.imageshack.us/img217/6569/redstuff3pq.jpg

Distillation was accomplished using the pictured set up. I opted for a jacketed, packed column to afford the best separation. I should have used a 2 neck flask and put a thermometer in the other neck but alas I didn't think of it in time.
http://img217.imageshack.us/img217/4633/distsetup10pl.jpg
http://img217.imageshack.us/img217/3958/distsetup28ui.jpg

As the fractions came off I collected a small portion in some sample tubes and marked them with the temperature. I should have measured the volume of the total distillate, but I was too busy running back and forth to the FTIR to be bothered.
http://img217.imageshack.us/img217/8158/ftir7fu.jpg

The first drops came over at 51º…. and you guessed it…
http://img361.imageshack.us/img361/8774/spec1556dp.jpg

The temperature held fairly constant at the head for quite some time as the acetone came over. I took many samples but the FTIR kept showing the same result.

The temperature rose to about 62º and held there while white fumes smelling of HCl began to come off. Not much distillate was collected. The temperature rose again to 80º and a small amount of yellow colored liquid collected.
http://img361.imageshack.us/img361/2057/spec2802rb.jpg

I would disregard this last spectra as it wasn't a good match and I'm sure the distillate was quite the mix of things, which tends to confuse the spectrometer.

The temperature rose again to 103º where upon the water began to come over in quantity along with trace amounts of a thin oil. I was unable to collect enough of it to test unfortunately. After the water substantially stopped coming the temperature rose to 108º and I turned off the heat. This is what was left.
http://img217.imageshack.us/img217/6222/remainder6aj.jpg

I tested the reddish remainder and what I got was interesting.
http://img217.imageshack.us/img217/7947/spec3rem1gg.jpg

It also said that it could possibly be this as well. We all know that isn't possible but you will notice that the spectra is very similar, enough to confuse the software.
http://img217.imageshack.us/img217/8306/spec4rem6wk.jpg

Sorry folks… no sign of any phorone. I will continue tomorrow using the precursor to form the peroxide and run those samples.
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ordenblitz
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[*] posted on 8-10-2005 at 19:39


Quince said:
------------------------------------------------------------
Pardon me, but could you explain FTIR and
MIR for those of us not in the know?
------------------------------------------------------------

MIR stands for multiple internal reflectance attenuated total reflectance accessory. Also known as MIRacle ATR.
http://www.kromatek.co.uk/Attenuated_Total_Reflectance_77.as...
It is an accessory attached to my FTIR. It allows for fast sample setup and testing in powders, liquids and films. It's not so good for hard crystalline material though for that a KBr tablet is best.

I could go on for pages explaining how all this works, so instead I got this from a site that explains the basic theory of FTIR.


Fourier Transform Infra-Red Spectroscopy, FTIR

Theory of Operation
The component atoms of polyatomic molecular groups are in constant dynamic state of motion with respect to each other. They are changing between the molecular ground state and quantum mechanically allowed excited states due to thermal excitation. This movement allows the spectroscopist to observe the twisting, bending, rotating and stretching motions of the atoms within a molecule occur at frequencies that are in the infra-red (IR) portion of the electromagnetic spectrum (0.7500 um). When infra-red light of energy coincident with the difference between the ground state and excited state of a particular molecular vibration is radiated onto a sample, the vibrations are stimulated (it jumps from the ground state to an excited state), and the light of that particular wavelength is absorbed by the molecule (IR absorbance). By monitoring the absorbance of the a range of wavelengths or frequencies of an infra-red light as it is transmitted through or reflected from (IR reflectance) a sample, a characteristic infra-red spectrum can be obtained. In Fourier transform infra-red spectroscopy, the source is modulated with a Michelson interferometer. This results in a signal at the detector which has a distribution of frequencies determined by the speed of the moving mirror of the interferometer. The resulting interferogram in the amplitude time domain is then transformed via the Fourier algorithm into the appropriate amplitude-wavelength domain, resulting in a characteristic infra-red spectrum for a particular compound.

Typical Applications

-Identification of extractable organic components from a device or wafer surface or PWB

-Identification of contamination (oils, polymers, solvents, fluxes, greases, etc.)

-Identification of unknown solid organic compounds (powders or residues and solvent or liquid organic)

FTIR is the leading analytical instrumentation for identification of organic substances
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[*] posted on 8-10-2005 at 20:35


Hmmmm .... that is interesting how
the FTIR is reading an indeterminate
compound it suspects is dimethylamine iodate , especially given the impossibility
that either iodine or nitrogen are present
in the sample :D

Whoever paid good money for that POS equipment got robbed :o :D ;)

Or maybe it's the software ? If Microsoft is involved somehow , maybe that explains things :D

[Edited on 9-10-2005 by Rosco Bodine]
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[*] posted on 8-10-2005 at 20:45


That was simply a case of a very similar spectrum. If you look at the two that came up on the search they are pretty close. That however does not mean that the chemistry is similar. You have to know what to believe and what to ignore.

These machines do not like soups of many things mixed together. But they are dead nuts right on if you do a good job with the glassware first.

Roscoe,

Where did you get dimethylamine iodate?
The search turned up two possibilities.. hydriodic acid or dimethylamine.

[Edited on 9-10-2005 by ordenblitz]
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[*] posted on 8-10-2005 at 21:01


peaks for dimethylamine and hydroiodic acid would be dimethylamine iodate .....

right ?
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[*] posted on 8-10-2005 at 21:09


No.
Individual peaks are not representative of compounds or elements.
They can however help to identify groups and bonds, etc. It's very different than GC or GCMS etc.
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[*] posted on 8-10-2005 at 21:18


Got it , FTIR sees a color signature in infra red , not a map of spectral peaks , but more like a tint value ....a mixed spectrum value .

So FTIR doesn't recognize the acetone polymer . It is probably the epichlorohydrin polymer at a lower level of polymerization , and even in the visible spectrum it does have something of an iodine color , especially for thin films of the solidified higher polymer which looks like spar varnish and is about as tough as polyurethane , sticks to glass tenaciously like an adhesive .
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ordenblitz
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[*] posted on 8-10-2005 at 21:29


It has nothing to do with colors or tints etc. It has to do with frequencies that are absorbed and those that are reflected.

If you go back a few posts you will see I posted a theory of FTIR.

It took me a long time to get it straight in my head. If your interested, there are a number of online resources that can explain it better than I.
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[*] posted on 8-10-2005 at 21:41


When you illuminate a sample with an emission source in visible spectrum , and detect what wavelengths are reflected and absorbed , " color " is exactly what you are detecting , along with albedo , reflectivity ..it is the same in astronomy and instruments used on telescopes for spectral analysis of objects to guess at their composition . The same thing can be done in the UV and X-Ray spectrum .
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[*] posted on 11-10-2005 at 18:54
Comon - he's doing great work!


First, to clarify: If a compound has a blue colour, it actually means it absorbs at lower wavelengths, like red, yellow and green. Thus blue light is left, which is what we perceive.
So the light you monitor is not the light you absorb of course.
Conversely, a compound may absorb infrared at a specific frequency, corresponding to the various bonds stimulated. This excitation of course is lost in due course in several ways, possibly even by resonant energy transfer.

Regardless, the method is very good in detecting the different rotational/translational/vibrational levels of each bonds, forming a compound spectrum that of course depends on other bonds in the molecule.


Anyway, I think, Ordenblitz, you are doing fantastic work.
The fact that a reference spectrum cannot be matched (or only to some obscure chemicals such as iodic acid) doesn't mean anything here, as it clearly cannot be iodic acid.
Neither does it invalidate FTIR as a technique. It is only to be expected that some molecules are similar but not identical the spectrum ordenblitz observed here, but it doesnt mean the method is invalid. You cannot expect every molecule in the universe to have a clearly distinct spectrum, particularly when there is always some error associated with acquiring each spectrum. In other words, Ordenblitz simply lacks the reference spectrum to compare the compound against. To my knowledge, this is how the company makes money in the first place, with accurate and enormous reference libraries.

Anyway, Ordenblitz, what I meant to say is that the fact that the spectrum of the distilled substance is very broad, with no baseline, means that you indeed are likely to have various products, with various overlapping energy states, all absorbing similarly (see the last pic http://img217.imageshack.us/img217/7947/spec3rem1gg.jpg ), possibly suggesting a polymer or a large array of very similar compounds.
Getting reliable reference libraries for various polymers (i.e. more than one product) is difficult, to say the least.

Furthermore, and more importantly -

The key experiment of course is to DIRECTLY compare the acetone peroxide to the putative DPPP product. If spectra differ, then we KNOW that the compounds are different. This is not necessarily proof for the identity of DPPP, but it is a PROOF for a different peroxide. And that is a big conclusion on its own.

More in detail, I'd possibly consider pooling the fractions minus those consisting of acetone (to remove any potential AP 'impurities';), and preparing the peroxide thereof. Then, to make normal trimeric AP.

Recrystallise both from toluene/chloroform/whatever, and compare with FTIR.

I'm looking forward to see the results!!!

Damn I wish someone had NMR, that'd sort it!

Oh, if you find the time, Ordenblitz, could you also please post the respective methods (very briefly) you used for making the respective peroxides, for future reference (in case someone else has analytical ambitions) Sort of to set a comparative standard.



PS Oh, and Quince, did I hear that right? It's an international forum you know? The core issue is that people are understood. To be honest I can't always say that in your case.
If you have an issue with Vulture's or someone else's English (I am sure there's a decent number of native English-speakers you might have an issue with), please, you are welcome to correct it via U2U, be our language ambassador, the conjunction-mod; rather than cluttering the thread with ramblings that are quite inappropriate, particularly in this case. Please just tell me you had a bad day.


[Edited on 12-10-2005 by chemoleo]




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ordenblitz
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[*] posted on 12-10-2005 at 19:10


I have finally had time to run the samples of TCAP and the suspected
DPPP on the FTIR. Hopefully this will solve the question once and for all.

I have described my method of production of the suspected DPPP
precursor and tests of same in a previous post. I used the method generally described by Roscoe, gleaned from his many posts.
The precursor was chilled and the H2O2 was added small portions, while
maintaining the temperature.
http://img441.imageshack.us/img441/578/synthdppp16xq.jpg
After all the peroxide was added, stirring was continued for a further 10 minutes.
http://img441.imageshack.us/img441/8994/synthdppp21mr.jpg
The material was filtered and washed with successive portions of
DI-H2O.
http://img441.imageshack.us/img441/1960/synthdppp32bf.jpg
The result was pretty much as described by most who have made it and is
evident in the pictures.
http://img441.imageshack.us/img441/5840/wetdppp4vy.jpg


The TCAP was made using Mega's method, with high quality precursors
from Fisher and Anachemia.
I was careful to keep the temperature at ~5º while the H2SO4 was added
dropwise.
http://img441.imageshack.us/img441/1434/synthtcap5yw.jpg
After the additions were complete I continued the stir for 1 hour then
placed the beaker in the freezer for 8 hours. It was then removed and
brought to room temp where it sat for another 2 hours before
filtration.
http://img441.imageshack.us/img441/5937/synthtcap23tb.jpg
The wet crystals were allowed to dry for 6 hours in a dessicator then
were dissolved in acetone, filtered then crashed out with de-ionized water.
http://img441.imageshack.us/img441/3567/wettcap1ce.jpg


Samples of the two materials were prepared for the FTIR using the KBr
pellet method because I was none to keen on pressure clamping samples of
primary explosives to my $1000 germanium MIR-ATR crystal.
http://img441.imageshack.us/img441/7148/kbrpowder9uf.jpg
The KBr method uses powdered potassium bromide mixed with a small
amount of the sample to be tested and compressing it under high pressure to a clear or almost clear "window" which the IR beam passes on it's way to the detector.
KBr is used because it is essentially clear to IR radiation, thus
providing
a substrate that holds the sample in the beam path.
I chose to use NAB dies to compress the sample.
http://img441.imageshack.us/img441/3319/nabdie2np.jpg
These are a simple stainless steel nut and polished bolts that are
tightened to compress the sample. The bolts are then removed and the nut placed in the sample compartment of the FTIR, in the beam path.
http://img441.imageshack.us/img441/4097/samplecomp6wr.jpg
The I did sweat a bit while tightening the KBr samples in the die, but
I don't think it's too dangerous seeing as how the samples are fairly
dilute in the KBr ~5%

And here it is…
The spectra in green is the TCAP. The one in the red is the DPPP.
I made it big so as not to lose any detail in the peaks.
I won't even bother to give my opinions as the spectra speak for
themselves!
Read em and weep boys and girls!
http://img406.imageshack.us/img406/3198/comparescan24el.gif
(It looks best if you the save the gif and open it with paint)

Lastly, I post the individual spectra of the two materials for those
who want the clean individual spectra.
TCAP
http://img442.imageshack.us/img442/3200/tcapscan503ul.gif
Suspect DPPP
http://img442.imageshack.us/img442/2968/sdpppscan508gw.gif


Whew… that was a lot of work!

Regards,
Ordenblitz

[Edited on 13-10-2005 by ordenblitz]
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[*] posted on 12-10-2005 at 19:22


Great work! Finally, this thread can be closed.



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[*] posted on 12-10-2005 at 23:01


Very nice work!
Why couldn't you have been here three years ago! :P

No need to close the thread, we don't yet know how 'strange goo' turns back into AP.

Also, the predicted IR spectrum of AP and DPPP are very similar, with the exception of the C=O peak... but those results are pretty much identical, way to similar for me to doubt.

So it's been AP all along :P Well I can't say I'm not dissapointed, but it's nice to have closure on what it is. Now lets get to work and figure out how the hell we got there from polymeric goo!
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[*] posted on 13-10-2005 at 04:34


What I have guessed occurs is a reaction which is analogous to the formation of hexamine from ammonia and formaldehyde in the sense that the reaction proceeds whether the formaldehyde is the monomer formalin or the polymer paraformaldehyde , by the reaction conducted in an aqueous condition . The end product is the same
whether the precursor formaldehyde is polymerized or not . The same or a very similar thing is being observed in the case of acetone where its polymerization products and or reaction products with HCl mixture , is functionally the same in its subsequent reaction with hydrogen peroxide to produce the same end product , irregardless of the order of addition . The principal end product is trimeric acetone peroxide by whatever different reaction paths may lead there .
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[*] posted on 13-10-2005 at 08:33


I have some of the material that was re-crystallized from toluene that I was going to run, but after seeing the spectra from the raw material I didn’t think it was worth the time.

If anyone would like to see the spectra from the re-crystallized material, speak up.
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[*] posted on 13-10-2005 at 18:57


Very nice explanation Roscoe, that does make a great deal of sense.

If it is at all possible, I would be interested in seeing the spectrum of mesityl oxide peroxide, formed by simply reacting mesityl oxide and hydrogen peroxide for a few days. Thats about all the information I have on it, but I would be interested to see how it's spectrum compared to that of AP. If you don't have mesityl oxide then don't bother.
I'm just curious to see how different peroxides compare to each other spectrum-wise, and also because mesityl oxide peroxide should be a contaiminant in the DPPP synthesis, since mesityl oxide is easily formed by dehydrating acetone which we have done.
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chemoleo
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[*] posted on 13-10-2005 at 20:35


Yes, that was in part the reasoning behind suggesting to make the peroxide of the red distilled oil (aka acetone-free); in order to see whether it would produce a different spectrum upon peroxide formation. Alternatively, compare TCAP to dimeric :o or tetrametric AP.

The point you made (Ctg) is a very valid one indeed.

I am not quite so sure as to the mechanism however. An analogy doesn't mean it holds, other than looking similar. Anyway. It's probably not so important (before we get into a pretty useless debate).

[Edited on 14-10-2005 by chemoleo]




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[*] posted on 14-10-2005 at 21:51


I'm curious what the very large peaks around 1200 represent?

I notice they are the only part that is signifigantly different...
I think it might be worthwhile to get a sample from the recrystalized DPPP to see if that difference is just from an impurity or something (probable in my opinion).
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shocked.gif posted on 21-10-2005 at 22:30
DPPP+UN Mix


Hey there fellow hobby chemists and
of course the higher educated of you...
I dont know if my information have any relevance of this matter, but i do think so.
I noticed, upon mixing DPPP and ureanitrate, there were a sudden change in temperature.. the temperature dropped. the "DPPP" was only about 90% dry, and so was the UN.
The mix was 50/50. i got a complete detonation of 8g mix with 0.8g "DPPP".. it was nothing like the AP/UN mix´ i´ve used
were 20 grams of ap/un didnt detonate properly, that was with a 10g detonating charge of ap. but my question is... Wats with the sudden temperature drop?? by the way, this is my first reply. happy to finally break into the discussion. it was a hard read to end(exept this last page), buuut interesting... hoping to get an answer...:)
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[*] posted on 21-10-2005 at 22:37


Welcome back, Hideki!

Wait, what am I saying... you're not welcome at all.

Hey fucktard, didn't you read the last several posts, which demonstrate beyond any doubt whatsoever that there is no DPPP and it's just some form of AP?

[Edited on 22-10-2005 by Quince]




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[*] posted on 22-10-2005 at 02:42


No need to resort to vulgarities or verbal abuse to make your point, Quince. There may in fact be DPPP, it is just not formed by acting HCl on Acetone and peroxidizing. The structure for DPPP which is given in the patent and by CAS certainly seems like it is a possible one to me.

But anyways, PyRoE_Inc, may I ask how you are determining the temperatures of the "reaction"?



[Edited on 23-10-2005 by Joeychemist]
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[*] posted on 22-10-2005 at 03:45


OK, but why'd you delete the picture post?

[Edited on 23-10-2005 by Quince]




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