knowledge Hungry
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nitrobenzoyl peroxide
As I was looking through the Organic synthesis databaseorganic synthesis database I came across this compound, C14H8N2O8. It is prepared by several
different methods.
quote:
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A 600-ml. beaker containing 100 ml. of water and equipped with an efficient stirrer, a thermometer, and a 200-ml. separatory funnel is immersed in an
ice-water bath. When the temperature of the water has fallen to 0–5°, 10 g. (0.13 mole) of sodium peroxide (Note 1) is added. Then, with vigorous
stirring, a solution of 37 g. (0.2 mole) of p-nitrobenzoyl chloride in 100 ml. of dry toluene is added dropwise over a period of about 30 minutes.
After the mixture has been stirred for an additional 1.5 hours, the precipitate is filtered and washed with 200 ml. of cold water (Note 2). The yield
of p-nitrobenzoyl peroxide is 28.5–29 g. (86–88%). It melts at 155–156°with vigorous decomposition .
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That was one method but there was another mentioned in very little detail about nitrating benzoyl peroxide(the acne medicine) with the standard mixed
acids. I was wondering if anyone had any ideas about the explosive power(if any at all) of this compound, it would appear to have a very low oxygen
balance, C14H8N2O8--> N2+4H2O+4CO+10C, however it might be mixed with AN. Any thoughts are appreciated.
Here is the website for the reaction http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0649
And here is a picture of the molecule http://www.orgsyn.org/orgsyn/chemname.asp?nameID=53523
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knowledge Hungry
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Does no one care about this? I thought some of you might be interested in a new potentially explosive compound, if you think that this compound is
worthless please let me know.
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Blind Angel
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Monograph number: 1149.
Title: Benzoyl Peroxide .
CAS Registry number: [94-36-0]
CAS name(s): Dibenzoyl peroxide ;
Additional name(s): benzoyl superoxide;
Molecular formula: C<sub>14</sub>H<sub>10</sub>O<sub>4</sub> ;
Molecular weight: 242.23.
Percent Composition: C 69.42%, H 4.16%, O 26.42%.
Line Formula: (C<sub>6</sub>H<sub>5</sub>CO)<sub>2</sub>O<sub>2</sub> .
Literature references: Prepd by inter action of benzoyl chloride and a cooled soln of sodium peroxide. Laboratory procedure: A. I. Vogel, Practical
Organic Chemistry (Longmans, London, 3rd ed., 1954) p 807; Gattermann-Wieland, Praxis des organischen Chemi kers (de Gruyter, Berlin, 40th ed., 1961)
p 115. Comparative clinical study with clindamycin, q.v., in acne vulgaris: L. J. Swinyer et al., Br. J. Dermatol. 119, 615 (1988). Review of carcino
genic and allergenic potential: D. J. Hogan, Int. J. Derma tol. 30, 467-470 (1991).
Properties: Crystals. mp 103-106degrees . May explode when heated. Spar ingly sol in water or alcohol; sol in benzene, chloroform, ether. One gram
dissolves in 40 ml carbon disulfide, in about 50 ml olive oil.
Melting Point: 103-106degree
Note: Caution: Potential symptoms of overexposure are irritation of skin, eyes and mucous membranes; sensitization d er matitis. See NIOSH Pocket
Guide to Chemical Hazards (DHHS/NIOSH 90-117, 1990) p 44.
USE: Source of free radicals for industrial processes. Oxidizing agent in bleaching oils, flour, etc.; catalyst in the plastics industry; initiator in
polymerization.
THERAP CAT: Keratolytic.
THERAP CAT (VET): Keratolytic.
(Merck Index)
This is for Benzoyl Peroxide, not the nitro one, but may help. I already though about aromatic peroxide but didn't how and also this may help
another discussion about Nitrating organic peroxide.
P.S.: the reagent seem a bit uncommon 
P.P.S.: Do you have a way to extract Benzoyl Peroxide from acne medicine?
[Edited on 25-4-2003 by Blind Angel]
[Edited on 25-4-2003 by Blind Angel]
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knowledge Hungry
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I am going to go the nitration of benzoyl peroxide route as NaO2 will be exceedingly difficult to obtain. Benzoyl peroxide can be bought as a reagent
and it is sold in 20-30% concentrations as the catalyst for fiberglass(the type used in cars). The acne medicine will take to much time to extract the
benzoyl peroxide from i think.
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madscientist
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Nitrobenzoyl peroxide will probably be extremely sensitive! The nitro groups on the aromatic rings will withdraw electrons, causing the oxygen-oxygen
peroxide bond to weaken considerably - thus increasing the sensitivity of the compound! And, of course, the improved oxygen balance will alone make
the compound much more sensitive.
I weep at the sight of flaming acetic anhydride.
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knowledge Hungry
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Are you saying that i should give up on it or that i should be careful?
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madscientist
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Don't nitrate benzoyl peroxide. Nitrate toluene, oxidize to the nitrobenzoic acid, then prepare the nitrobenzoyl peroxide from that (I know
it's more difficult that way, but it's also much less hazardous). I would say that it shouldn't be particularily dangerous if
you work with very small amounts (no more than 1g of final product accumulated in one place at any given time).
I weep at the sight of flaming acetic anhydride.
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Blind Angel
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It's the synth in the first post 
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PHILOU Zrealone
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Ar-CO-O-O-CO-Ar
OB: -181,7%
melting and deflagration point: 107°C
Impact sensitivity: 5 Nm
Friction sensitivity: 120 N
Critical diameter of steel sleve test (confinement test): 10 mm
Sand test: 10,8% of TNT
Despite its low oxygen contain it is an explosive.
Explosion strenght is low but sensitivity is relatively high.
You may expect from the introduction of a nitro in para position:
*to get a little better stability (the O-O link will be a little stronger)... but stil peroxydes are by nature a hell and I wouldn't dance on it.
*to get a higher density.
*to have a better OB and thus a better energy output --> increased explosive strenght and brisance!
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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PHILOU Zrealone
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Of course better properties for C6H(NO2)3(CO)2(O-O)2(CO)2C6H(NO2)3
(NO2)4C6(CO-O)2 and (NO2)4C6(CO-O)2 and (NO2)4C6(CO-O-O-CO)2C6(NO2)4 and lower NO2 containing molecules.
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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KABOOOM(pyrojustforfun)
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PH Z! sounds your molecules have some geometrical problems. I
may be wrong that is if the -CO-O-O-CO- groups are not in ortho
position even o-position may not work. do u know samples of
such tricyclic peroxides? but still very interesting. the fact
these fuckers(polynitro ones) can be powerful explosives is
exciting enough for me to do experiment on them no matter how
unstable/useless they are.
another idea is oxidize TNT to TNbenzoic acid, react with SOCl2
to get 2,4,6-TNbenzoyl chloride, dissolve in a suitable soln
add Na2O2 to get 2,2',4,4',6,6'-HexaNitrobenzoyl peroxide. If I
decide to experiment with them I'll transfer the required lab
equipments to a wasteland !
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