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The_Davster
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I am unable to open the file...
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Rosco Bodine
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| Quote: | Originally posted by Pyroz
The lab sythesis has shown the validity of the german patent. |
Pyroz , see if you can get the yield figure expressed in grams , and the method of drying . My experience is that this material has a significant
residual moisture content .
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Pyroz
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:::
try this::: richtextfile
Attachment: chemlabsynth.rtf (20kB)
This file has been downloaded 1051 times
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Rosco Bodine
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Pyroz , Nice to see a detailed synthesis report , but I have to say it leaves many unanswered questions . In the start of the synthesis report it
says , | Quote: |
"The validity of the German patent DE951660 will be illustrated through a series of tests that will prove or disprove the existence of
C18H26O2(O2)5 or diphorone pentaperoxide. " |
I don't see enough data in the synthesis report to fulfill that "proof or disproof" for DPPP , but it does confirm and add to some of
what we already know .
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The_Davster
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Strange, I still cannot download it correctly. This is what I get when I click the attachment.
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Rosco Bodine
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rogue chemist :
I like my files like my women ,
acrobatic  Try this
Attachment: Synthesis produced by R.pdf (81kB)
This file has been downloaded 1659 times
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Mickhael
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Rogue I couldn't download it when I just clicked open, but I could when I hit save instead...maybe try that? otherwise i'm sure someone who
got it ok is willing to email it to you...myself included.
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The_Davster
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Thanks everyone, it just must be my computer acting up. I asked a friend of mine to try all of the attachments on his computer and they all worked
for him, wheras none of them are working for me. Oh well I have a copy of the lab results now so its all good .
Well, back on topic, I agree with Rosco here, this patent and now lab results do not prove the existance of "DPPP", only the production of
an explosive organic peroxide, with the exact formula still to be determined.
[Edited on 16-1-2005 by rogue chemist]
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Rosco Bodine
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rogue chemist :
You were asking me earlier about the sublimation test result on the reverse order of addition experiemnt where I got the best yields , and it looks
about halfway finished and has produced the good cubical clear crystals which I am pretty convinced are the DPPP sublimate . A sample from my last
batch of DPPP by the conventional peroxidation route has just been added to the sublimation test group . The yield was not good on my last DPPP
synthesis experiment , only about 47% of theory , but the product appears to be of high purity and it burns extremely fast compared with the other
samples . It may be that it is simply finer granulation and more completely dry , but it really burns very quickly in even a small amount actually
seeming more like fulminate than AP in the quantity where it gives that mild "pop" where you know doubling the quantity it would likely
detonate unconfined , and probably at less than the amount where AP would be demonstrating the same transition . I am simply speculating here based
on experience , and have not stepped up the charge weights incrementally to see where DDT actually occurs for unconfined amounts . The flash is
quicker for the DPPP ignited in small amounts .
Putty tests may also be revealing. Control samples related to AP , along with a variation upon the method for AP adapted to the peroxidation
conditions we are using for attempts to make DPPP are going to be part of my experiments , to provide data going to some of the doubts which Axt
related , and frankly I share the same reservations , absent some of the skepticism . I am going to do an experiment where I mix prechilled acetone
and prechilled HCl at a low enough temperature to hopefully inhibit any significant polymerization and then peroxidize at low temperature using the
same conditions ,
to see what form of regular AP crystals are produced , and if they form any different crystals upon sublimation from the sublimate obtained from AP
made in the usual way . This should address any question as to whether the sublimed crystals of regular AP may simply develop differently depending
upon the conditions under which the AP was made . Hey Axt , I saw that one coming
[Edited on 16-1-2005 by Rosco Bodine]
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Chris The Great
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Can those at the universities determine the IR spectrum and do other tests such as X-ray scattering (Not the correct term, but you know what I mean)
to try and determine the structure? That would definatly be some useful information we couldn't get through our home experimentation.
When I get some more H2O2 I'll try the synthesis as well as some other tests, as well as take some microscope pictures of the crystals, such as I
did with AP. That would definatly help with determining crystal structure.
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Matsumoto_Hideki
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More results coming soon
My test results from the University are still yet to be
recieved. Hopefully this week.?
As ar as the test footage, nothing yet as I was still unable to get to the range BTW.. it was totaled from the snow storm we had here. This is
something I seldom see here on the west coast. SNOW SUCKS
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Rosco Bodine
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possible variable about precursor identified
My last experiment with the conventional order of addition of the peroxide to the precursor seemed to produce the desired product in good purity ,
however the yield was low at 47% , and I have been thinking about this and trying to identify what variable is responsible for the lowered yield .
The precursor which I used had been freshly prepared a few hours earlier from 47ml HCl and 50 ml acetone in a sealed bottle heated for about 3 hours
at 65 C to the point of development of that deep ruby red color which has been tenatively identified as the probable endpoint for the reaction
producing the precursor . Now I question that assumption because of an unused sample of the precursor which was made the same way but has been
refrigerated for a week at about 4 C since it was made . The refrigerated sample has continued to deepen in color to a very dark burgundy or
"oxblood" color without
an precipitation of any oily upper layer , so it appears the formation of the soluble precursor continues significantly in the cold , without
producing an upper layer as would occcur if the reaction was being driven by heating to the same level of color darkening . The precursor which has
been refrigerated for a week is extremely dark in color , almost to a black
appearance , and yet it is actually still transparent to intense light and not yet cloudy or opaque as would indicate a precipitation or formation of
an emulsion with some suspended insoluble material .
It seems likely that to a point , initial warming of the acetone and HCl mixture increases the formation of the phorone dihydrochloride precursor ,
and then begins to also produce the xylitone or xylite oil upper layer precipitate if heating is continued , which represents a loss of precursor .
Further heating is counterproductive past that point , but if the reaction mixture is then cooled and kept cold for an extended time , it appears that
the reaction proceeds more slowly continuing to increase the concentration of the phorone dihydrochloride , but without producing the greater amounts
of xylitone which would be observed accumulating at higher temperatures . If this is indeed true , then patience will be a virtue in preparation of
the precursor for highest yield prior to the peroxidation . Because it appears that at low temperatures and slow reaction rate , the formation of the
phorone dihydrochloride in increasing concentration is preferential to the formation of the byproduct xylitone as occurs at higher temperatures . If
this is the case , then it may increase the DPPP yield by 50% to simply store the "ruby red" precursor cold for a week before it is used ,
as compared with using that precursor freshly prepared . Does this square with anyone elses observations or thoughts ?
A related idea which I have concerns the formation of triacetone dialcohol which is involved in the reaction , as well as it may also be involved in
the formation of ordinary trimeric acetone peroxide via the reaction in the cold where HCl is used only in catalytic amounts . It is known that under
alkaline conditions that very low temperatures triple the concentration of triacetone dialcohol ultimately reached at equilibrium for the reaction ,
as would occur at higher temperatures , and this could also be true for acid catalyzed polymerization , which may account for the formation of reguar
trimeric AP being favored by low temperatures , if the triacetone dialcohol were actually an intermediate in the reaction sequence which forms the
ordinary trimeric AP .
It seems possible that it may even serve to concentrate the yield of phorone dihydrochloride by a series of a few periods of mild warming for a short
period followed by longer periods of extreme cooling . This would be the case if the triacetone dialcohol formation is favored by low temperatures ,
while its condensation with HCl is favored by warmer temperatures . If there is a conflicting thermal parameter for the formation of each , where the
optimum condition for the one is opposite for the other , then cycling the reaction through a few cooling and mild warming cycles could drive the
reaction further towards completion . This could be as simple as removing the sealed bottle from the refrigerator each day and setting the bottle in
a pan of warm water for thirty minutes , and then returning it to the refrigerator . It is possible that some special manipulation of this sort may
be required to increase the end yield of DPPP . Whether this particular idea has any validity or not remains to be tested .
There are many variables to be examined about this reaction , thanks to the lack of description of details in the patent .
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Matsumoto_Hideki
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I just got off the phone with the chemistry student doing the DPPP research. He believes that the reaction has to continue until the colour reaches
its full dark stage. Triacetone dialcohol does form but it quickly changes into a nearly black Phorone-isomer hydrochloride when free HCl reacts with
it. This really seems to make sense to me. The Xylite oil forms as a skim on the surface indicating "Phoronisation" - if thats a word.  More information will be gathered this week.
I stand behind this claim to...it has been my experience as well.
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chemoleo
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Hmm, what's this suddenly about xylitone and triacetone alcohol?
From what I could find about xylitone on the internet, it is ' A yellow oil having a geraniumlike odor, produced as a side product in making
phorone'.
But thats ALL the info. No patents on it, nothing. What's the evidence that this is produced here?
Same goes for triacetone alcohol. From what I read it is formed under basic, that is, alkaline conditions. Numerous patents employ
various acetone condensations with Ba(OH)2, KOH, NaOH, whatever. Hardly the conditions we use here, with a large amount of HCl. I am getting confused
as to where all these theories come from, and what the evidence for allthose theories is.
Then all these precursors- dichloro/pentachloro phorone - we don't even know the identity of the final product. How can we even dare to speculate
on what product is formed at this point or that point during the reaction? Do we even KNOW, at this point, that some phorone derivative is reacting
with H2O2, and not something else? Think not.
I guess, before we discuss page upon page the potential reaction products- wouldn't it first make sense to confirm, beyond
doubt, that the putative DPPP produced this way, with different crystal structure and all that, is indeed more powerful? From what I have seen this
far, there is tentative confirmation, that was disputed lateron again. Including the putative DPPP smelling like AP, sublimating as fast as AP, and
with slightly different crystal structures? The fact that it sublimates is also in direct contradiction to what it says in the patent btw.
I don't quite understand what the use of this whole discussion is until we confirmed beyond a shred of doubt that the new substance is indeed a
new peroxide, which is NOT AP, and more powerful than AP?
Shouldn't we first properly characterise the end product before we discuss in many pages how it is made the most efficient way, and whatever side
products are produced?
Just trying to get this whole thing back onto track, before it turns into an 'acetone condensation' lecture! I realise testing of various
conditions is required. But theorising on the reaction itself while we don't even know the identity of the final product...hmmmmm!
[Edited on 16-1-2005 by chemoleo]
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Rosco Bodine
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| Quote: | Originally posted by chemoleo
Hmm, what's this suddenly about xylitone and triacetone alcohol?
From what I could find about xylitone on the internet, it is ' A yellow oil having a geraniumlike odor, produced as a side product in making
phorone'.
But thats ALL the info. No patents on it, nothing. What's the evidence that this is produced here? |
You
are right about the "xylitone" and I was using that term , thinking about the "lab report" which Pyroz posted having named this
material "xylitone" . I do not know for a fact what it is , and my first thinking is that it is predominately phorone , triacetone
dialcohol , and higher acetone polymers in mixture , which smell nothing like geraniums to me , but something closer to linseed oil or varnish . The smell is like the stinky odor of oil based paint , especially
an old can which has been opened after years of storage and the leftover paint has gelled into an unusable goo . | Quote: |
Same goes for triacetone alcohol. From what I read it is formed under basic, that is, alkaline conditions. Numerous patents employ
various acetone condensations with Ba(OH)2, KOH, NaOH, whatever. Hardly the conditions we use here, with a large amount of HCl. I am getting confused
as to where all these theories come from. |
Well it isn't a theory that acetone polymerization also
occurs under acidic conditions . The synthesis of mesitylene first involves the formation of acetone polymers at mild temperature under acidic
condition , and then those acetone polymers are "cracked" at higher temperature which results in ring closure to form mesitylene . The
Mackowiak patent also shows the triacetone dialcohol as the first polymerization product from acetone and HCl . | Quote: |
Then all these precursors- dichloro/pentachloro phorone - we don't even know the identity of the final product. How can we even dare to speculate
on what product is formed at this point or that point during the reaction? Do we even KNOW, at this point, that some phorone derivative is reacting?
Think not. |
No not for certain , but we are seeing that certain variables are affecting the yields of the
unknown product we are getting , and all the data contributes its small part to helping understand the reactions occurring . | Quote: |
I guess, before we discuss page upon page the potential reaction products- wouldn't it first make sense to confirm, beyond
doubt, that the putative DPPP produced this way, with different crystal structure and all that, is indeed more powerful? |
Chomping at the bit for blast data yeah that's where
the rubber meets the road , if the tests are done right without any bias towards seeing reasults as you would hope to find , but just being content
with the facts , whichever way that goes . | Quote: | | From what I have seen this far, there is tentative confirmation, that was disputed lateron again. |
Not
disputed , just not yet independently confirmed . | Quote: | | Including the putative DPPP smelling like AP, sublimating as fast as AP, and with slightly different crystal structures? |
Nope , all samples of "speculative" DPPP so far are only producing clear cubical crystals upon sublimation , with very
small amount of any other form crystals . | Quote: | | The fact that it sublimates is also in direct contradiction to what it says in the patent btw. |
Where
exactly does the patent say that the DPPP does not sublimate ? Looked carefully and I don't see that declared anywhere . | Quote: |
I don't quite understand what the use of this whole discussion is until we confirmed beyond a shred of doubt that the new substance is indeed a
new peroxide, which is NOT AP, and more powerful than AP? |
That finding could be the result of the
experiments being done . It is more than simply shooting in the dark hoping to hit something which I am doing anyway . | Quote: | | Shouldn't we first properly characterise the end product before we discuss in many pages how it is made the most efficient way, and whatever
side products are produced? |
Not when we are all comparing notes and thoughts on what we are seeing to
reenforce our identification of the product and its purity , color , smell ect . so that definitive tests for density , melting point will be believed
to be data for the pure substance we are calling DPPP , and not some mixture of compounds . It is standard practice to attempt different methods for
synthesis and compare different samples properties . | Quote: |
Just trying to get this whole thing back onto track, before it turns into an 'acetone condensation' lecture! I realise testing of various
conditions is required. But theorising on the reaction itself while we don't even know the identity of the final product...hmmmmm!
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Sheeesh , lighten up will you . It takes days for the sublimation tests to develop , and in the time of
waiting I am examining other unknowns to see what useful information may be found , testing what ideas I have as I go . Right now I have an experiment
underway where I mixed the acetone and HCl very cold and returned them to the freezer for keeping in the cold . Tomorrow when I gently warm that
mixture , if I get color development much sooner and more intensely than from the usual method , then I wil know my theory above about the cold
favoring the formation of triacetone dialcohol while warm temperature favors its conversion to phorone dihydrochloride is correct . All such
experiments are pertinent and germane to supporting what we are speculating are the reactions which lead to the DPPP . Don't worry , I will do
the detonation tests myself , including some putty tests comparisons with control samples of known AP , and compressed charge comparisons of DPPP
versus AP .
Maybe we should just all retire to the lab and range with our notebooks in hand and then come back when all the work is completed to report our
results , as opposed to real time reports of piecemeal
results and ideas . We can tie it all together to make sense later . That's okay by me . I know I had the impression not everybody could follow
where I was going with all of this from the beginning with my "sealed bottle experiment" which had its usefulness in my mind anyway .
Dittos for the sublimation and other experiments , all working parts of an analytical study of the "DPPP" which is sufficient to satisfy the
skeptics with definitive answers and data . I am sure as hell tired of this too , but the experiments are providing useful information and I'll
keep going till I have my own "finding" that will withstand scrutiny .
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Mickhael
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Right on Rosco...I for one will continue to look forward to your updates and suggestions on the synth...I have a meager amount of experience and
equipment so for the most part I just have to stand back and watch, and then try the occasional method thats brought to light. I think that constant
updates by everyone is the best way to keep everyones brains thinking on new possiblities and not drift into single minded opinions...I know my
thoughts on the substance have continually grown with the new information discovered by verious people on this thread...I have no doubt that within
the new few weeks almost everything we have been wondering about will be solved
That'll be a day to break out the good stuff and have a toast 
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Pyroz
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--we are all coming up with information that will help one another. I am sorry my eagerness is sounding like insanity. Its pretty clear to me that the
material created in this synthasis has a much higher VOD than standard TATP-triAcetonetriPeroxide, but like I say it never hurts to have others try it
out and see it for themselves.
I will only post lab info from now and keep technobabble to a minimum... sorry, rosco and others.
Guyz, we need more people doing VoD tests! Chemical synthasis information or not it all boils down to detonation tests--- "kaBOOM!" It will
become explictly clear once the tests are done.
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PainKilla
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Soon I will be trying this synth with another regeant... hopefully I can disprove the "DPPP" via phorone theory .
more details will follow soon.
How interesting.... H2SO4 and Acetone smell EXACTLY like AP. Perhaps DPPP is a mesitylene deritive. If anyone has a good distilliation setup, please
try distilling mesitylene and peroxidising it.
It is that sweet smell of AP, when equal portions of h2so4 and acetone are mixed. This produces mesitylene which I think is a direct precursor to the
formation of both these substances, perhaps one and the same. Maybe one is tertrameric and the other tri. I don't know, but soon I will make much
more exact results. Just something to think about.
[Edited on 16-1-2005 by PainKilla]
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PainKilla
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Mesitylene and Energetic Deratives
Mesitylene is 1,3,5-trimethyl benzene. It's the flammable deritive of H2SO4 and acetone, usually via distillation. It also has a ketone, methyl
isobutenyl ketone, which can form peroxides supposedly. I think it is important to research these compounds as they may be more important than the
phorone that everyone is so excited about. I know I am not the only one who holds doubts about DPPP.
When I mixed H2SO4 and acetone at room temperature, the temperature of the mixture shot up drastically. The mixture smelled very strongly of AP....
This is something I am quite curious about. DPPP seemingly no one agrees about. It does smell like AP, or it doesn't....
Also to be noted, is that mesitylene often looks JUST LIKE THE "PCP" mixture that everyone regards as a trademark charecteristic. I think we
should have some people more experianced add some input on this.
I think this should stay in the Energetic Materials, as we WILL have an energetic material within the week .
WHOA! I am not sure what this picture is, but if it is peroxides then I think we have DPPP....
http://maildbs.c.u-tokyo.ac.jp/~nisikori/mvct.htm
I don't think thats peroxides but still looks interesting as I know ether defiently makes one. I can't read boxes (what my browser shows) so
I cant tell what it is.
[Edited on 16-1-2005 by PainKilla]
[Edited on 16-1-2005 by PainKilla]
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Pyroz
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I'll see if Hideki wants to translate--- I too read japanese::: I'll do my best.
well, i can say without a doubt that the sulphur yellow colour I had when I made my 1st successful batch of "DPPP" was obviously there. i
didn't add enough hydrogen peroxide and I got a low yield. There was a lot of this yellow material. Very pungent odor! Still I continue to get
yellowish crystals and after purification they are almost pale mint green/yellow
PS. my first trip to the lab, I was told that Mestyl Oxide may have been produced --- there was some arguement that amongst some of the chem students
and a few people on this forum. ----Mesityl Oxide can form explosive peroxides, this much is known---
Here is a picture:
[Edited on 16-1-2005 by Pyroz]
[Edited on 16-1-2005 by Pyroz]
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Rosco Bodine
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Pyroz ,
That pale mint green - yellow , very nearly white is what I got from my last synthesis and the smell to me is like
pyrethrin based bug spray like you use on tents and sleeping bags . It is a very faint odor to me not as strong as regular AP . To me regular AP has
very clean light aromatic odor which reminds me of ether ,
but is a definite odor which doesn't require getting your nose down to a half inch away from it to smell it as does the DPPP , which has a barely
detectable odor . I have gotten a product having that faint insecticidal odor by either order of addition on the peroxidation , and the exact same
barely tinted color , which is sort of like the off white color that lime juice gives a frozen daiquiri . Does that square with your result ?
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PainKilla
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My AP doesn't always have an extremely detecatbale odor etoehr. In fact, most of the time I have to get really close to it... It has an EXTREMELY
addicitve smell i think. I can't get enough of it until I realize I'm sniffing a sensitive primary.
PS: Now I know it smells like mesitylene (see my above post)
[Edited on 16-1-2005 by PainKilla]
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Pyroz
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yes, rosco...I have been getting the same material as you have. It is pale green-- like lime juice :0
this is the material i have been getting from all reactions - the last photo which was of a botched batch
here is my yield from last week... its completely dry...here is a photo of it.
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chemoleo
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I doubt these pictures from the japanese link are peroxides, as pretty as it may look. The peroxide of diethylether isn't a nicely crystalline
solid, as far as I know. It looks a bit more like some crosslinking experiments, with a compound called MV2+, which is some ionised biphenyl
derivative.
As there is not much consensus at this point what products of the acetone/HCl reaction react further with H2O2, don't you think it's a
little early to create a thread on peroxides of mesityl oxide, or whatever?
Let's just see how this goes, maybe Rosco's experiments sort out which conditions predominantly produce the oily substance, and which
don't. From this I hope we can work out which preferentally produces the crystalline substance with H2O2, and from this in turn maybe someone can
do some more comparative power tests ... in a perfect world 
By the way, in Gattermann I read today that acetone reacts in the presence of HCl-gas to mesityl oxide and phoron.
This may be another thing to try, to bubble HCl gas into acetone!
According to Beyer&Walters Book on Organic chemistry, mesityl oxide is a clear liquid that smells slightly of peppermint (!!).
Phorone is, on the other hand, a yellow substance that has a melting point of 28 deg C !!! In this book it also says that it is obtained by reacitng
HCl gas with acetone, while mesityl oxide is a side product.
Could I just point out one thing re. phorone and mesityl oxide - the former is the condensation of three molecules of acetone, and mesityl oxide is
the condensation of two molecules. The methyls of the acetone react on either side with the carbonyls of two molecules of acetone to get phorone,
while mesityl oxide reacts only with one methyl group.
I.e.
Mesityl oxide
(H3C)2C=CH-CO-CH3
Phorone
(H3C)2C=CH-CO-CH=C(CH3)2
Not surprisingly, the mesityl oxide also forms putative peroxides. If the patent holds any truth, it wouldn't surprise me if the putative DPPP
was a mix between mesityl oxide peroxide and DPPP.
Regarding the smell- that's interesting. It looks like this is not a reliable indicator to identify these peroxides.
[Edited on 16-1-2005 by chemoleo]
Never Stop to Begin, and Never Begin to Stop...
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PainKilla
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I will be attempting the mesitylene peroxide later this week. I finally stopped being lazy and got acetone. I have like 20ml of H2SO4 though. Anyone
with better organic cehm knowdledge mind telling me thier ideas on the stabilty of this compound?
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