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garage chemist
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Glowing tomato
http://www.metacafe.com/watch/757249/make_a_glowing_tomato/
How the hell does that work? That seems like a really weird concontion of chemicals: matchheads, bleach and hydrogen peroxide.
I first thought "singlet oxygen", but the glow is way too strong and too long for that. Also, no oxygen seems to be evolved.
The UV detection of "high-phosphorus matchsticks" is also bullshit, as phosphorus does not fluorescence under UV light- white phos glows in the dark,
but by itself and is consumed in the process.
Also, which of the two layers are they withdrawing with the syringe?
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Eclectic
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The matches may be irrelevant, unless chlorates or chlorites help the reaction along:
http://blog.modernmechanix.com/2006/12/09/firefly-chemistry/
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Ozone
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Quite cool, if it works. IIRC strike anywhere matches contain antimony (III) sulfide, RP, K chlorate and powdered glass. Of interest is the luminous
nature of the intermediate "oxidized" match compound (and the two layers, of which it looks like the clear top that they are using). This evokes a
very small amount of white P (does look like WP glow), but evolution of white P from red is a physical (phase transition) rather than a chemical
process. Is the bleach treatment exothermic?
Hmm. The thing does not appear to smoke or steam when cut and exposed to air whilst aglow. IT also appears cool enough to handle comfortably. Hmm. Sb
oxychloride?, KClO3 should remain as is (maybe some NaClO3 is formed, definitely if there is any bleach left in the mix and H2O2 is added---NaOCl will
oxidize H2O2 to yield O2 (likely some 1Dg singlet O2) NaCl and traces of NaClO3, but this rxn is frisky and no evidence of gas evolution was seen).
POCl3? Complex phosphorus-peroxide species? wierd.
I'll have to try it out (I'll have to buy these matches first. Maybe making match compound would be easier and work a bit better).
Definitely on my to-do list,
O3
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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BromicAcid
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When they start putting the H<sub>2</sub>O<sub>2</sub> in it looks like there is a very fast gas evolution, all around the
syringe it looks like bubbles are coming out of different parts of the tomato (might just be an effect of having a bunch of liquid forced into a
tomato though). My first guess would be the hypochlorite reacting with the peroxide (They didn't say the concentration as far as I noticed), that
emits a red light that would compliment the tomato and something in there might be acting as a sensitizer thereby allowing for a good light emission.
When I was researching compositions of match heads I couldn't find any modern manufacturers using red phosphorus in the heads themselves. Most seemed
to use phosphorous sesquisulfide or just some mixture of phosphorus sulfides. If the NaOCl isn't the main culprit here I would place some of the
activity on that but there is also the chlorate in the mix there. Before they added the peroxide I thought maybe the hypochlorite/chlorate mixture
being acidified slowly by the natural juices of the tomato might facilitate a nice chemiluminescent reaction with the phosphorus sulfides. But then
again there are a lot of factors that could come into play here. Although this would seem to be an easy experiment to test out in a lab in that there
are only a few key 'ingredients' that I can pin point in the reaction.
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guy
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Singlet oxygen rapidly oxidizing white phosphorous.
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Ozone
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Forgot about the sesquisulfide in modern compositions. I do know that we will get some singlet O2 when NaOCl oxidizes H2O2. At first I thought this
rxn would be too fast for a persistent chemiluminescence. However, now that I think a bit more about it, the tomato flesh is likely limiting mass
transfer to diffusion (hence gradual emission) AND the stability of the H2O2 will be affected by the lower pH creating hydroperoxide intermediates
(peracids, etc.) which will have much longer lifetimes at the relatively low temperatures employed (rt).
So, perhaps we get some singlet O2 with time release, in the presence of an activator some decent fluorophore and away we go.
I do think that the pH and rate of reaction allowed by mechanical stricture are main factors which make the NaOCl/H2O2 system slow enough to perhaps
work.
Unexplained, however, is the phosphorescence (triplet) of the intermediate NaOCl product. Could the sulfides be oxidized from the P to yield maybe,
HSO3, chlorosulfonic acid (and who knows what all else) and P (maybe white)? Hmm. Let me look around and see If I have any matches. First I'll try
bleach and H2O2 (at 2.5 and 3%, respectively, in the dark).
Cheers,
O3
[Edited on 9-8-2007 by Ozone]
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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Ozone
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NaOCl and H2O2, do not provide any visible light (just effervescence and heat). Likewise with the same test with a small amount of added luminous
paint. [edit] this was to test if UV was emitted; it would have glowed much more brightly--it's luminosity remained unchanged in the presence of
reacting NaOCl and H2O2.
I though I might bave tomato juice, but I found only fruit flavored V8 .
For tomorrow, i wouild like to get some benzophenone, Na fluorescein, matches, RP (maybe), stronger peroxide...and...a tomato. Maybe we can
test-tube-it-out.
[edit] I do have lycopene and folic acid, for the hell of it.
Cheers,
O3
[Edited on 10-8-2007 by Ozone]
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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DerAlte
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Lycopene in the tomato? Think of all those conjugated double bonds gradually going pop, pop, pop!
Regards,
Der Alte
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jimmyboy
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The glowing tomato is hogwash -- matches have Red P not White -- which doesn't glow unless its converted with a good amount of heat -- neither
peroxide or a bleach solution will do this - hypochlorite and peroxide does glow faintly but not like that... the tomato was glowing like a light
bulb -- what it really looked like is he either used phosphorescent dye and a blacklight or a tiny LED to do this trick... its entertaining to be
fooled i guess.. maybe he will make another 100 bucks on metacafe..
[Edited on 10-8-2007 by jimmyboy]
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Eclectic
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Hey! Did ANYONE read the link I posted?
Again:
http://blog.modernmechanix.com/2006/12/09/firefly-chemistry/
[Edited on 8-9-2007 by Eclectic]
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YT2095
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I have and am wondering if things like Rhodamine B or 6G would work instead of some of the other items like Chili powder and the likes.
I also have something called Optical Brightener, it looks like 3in1 oil, but in water it glows blue under UV but doesn`t have a color itself.
Nice link Eclectic, Thanks 
\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
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Xenoid
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| Quote: | Originally posted by Eclectic
Hey! Did ANYONE read the link I posted?
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Yeah! Great site! There is some fantastic "stuff" there!
I wonder how an article titled " Fun with explosive gases for the home chemist " would fare in these times of paranoia.
Xenoid
[Edited on 10-8-2007 by Xenoid]
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Eclectic
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It's just that the 1930's article on chemiluminescence may explain what's going on with the bleach, peroxide, and tomato...
Do the chemicals in the matches actually make any difference?
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chemkid
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I happen to have a long wave UV light and i checked the different boxes of safety matches only one of which luminesced, but it was bright orange. I am
yet to try strike anywhere matches.
Chemkid
[Edited on 10-8-2007 by chemkid]
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Xenoid
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| Quote: | Originally posted by Eclectic
Do the chemicals in the matches actually make any difference? |
I don't think so!
Eclectic, you are spot on with your link!
It's the colouring agent that is being extracted, in the upper layer and that is what is glowing when the matches are illuminated with UV. The
references to phosphorus are bullshit! The video maker is confused! The pinkish dye is probably a rhodamine type dye.
Xenoid
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YT2095
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probably B then, as 6G is a little less vivid and more Red than the In-You-Face acid Pink of B.
nope, I just tried it, Rhodamine B and NaOCl (12%) and then 9% H2O2. no lights!
I think I`ll try the one Eclectic mentioned in the article with the Alcohol etc...
it won`t be today though.
[Edited on 10-8-2007 by YT2095]
\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
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Eclectic
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I think you may need an organic substrate for the whole mess to react with. Try injecting it into various fruits and vegetables.
[Edited on 8-10-2007 by Eclectic]
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Per
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Maybe first trying to get the slight glow precursor in the syringe might be more succesfull, until having this reagence attemptions with fruits which
are more strenuouse may doesn´t make sense.
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ssdd
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I tried this last night with no result, I think I may have added too much bleach to the match heads....
I am gona try this again later today and see what happens.
Interesting experiment I must say.
-ssdd
All that glitters may not be gold, but at least it contains free electrons.
-- John Desmond Baernal
http://deepnorth.info/ |
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YT2095
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good point about the bleach, I used my 12%, the sort that hisses when you open the lid and knocks you on your ass with Cl2 gas if you`re not careful.
the Rhodamine B didn`t even dissolve in it until I added the 9% H2O2.
\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
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ssdd
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I tried this once again using less bleach and newer matches... once again a complete failure. What on earth could be going wrong here. (The main
difference I see is that I dont get the red liquid when they layer out, I get a whitish clear liquid and a white residue on the bottom.)
anything?
-ssdd
All that glitters may not be gold, but at least it contains free electrons.
-- John Desmond Baernal
http://deepnorth.info/ |
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guy
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| Quote: | Originally posted by ssdd
I tried this once again using less bleach and newer matches... once again a complete failure. What on earth could be going wrong here. (The main
difference I see is that I dont get the red liquid when they layer out, I get a whitish clear liquid and a white residue on the bottom.)
anything?
-ssdd |
Are you using non-safety matches with white phosphorous? Safety matches use red phosphorous which is not good,
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garage chemist
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There are no matches with white phosphorus. Those have been outlawed LONG ago.
Also, white phos doesnt glow in solution! Get that thought out of your head that white phos might play any role here!
White phos is also insoluble in water, and is oxidised by bleach to phosphoric acid WITHOUT appearance of any glow- I tried that out myself!
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guy
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| Quote: | Originally posted by garage chemist
There are no matches with white phosphorus. Those have been outlawed LONG ago.
Also, white phos doesnt glow in solution! Get that thought out of your head that white phos might play any role here!
White phos is also insoluble in water, and is oxidised by bleach to phosphoric acid WITHOUT appearance of any glow- I tried that out myself!
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Ok haha. Then what are non safety matches made out of nowadays? That video confused me.
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Xenoid
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| Quote: | Originally posted by guy
Ok haha. Then what are non safety matches made out of nowadays? That video confused me. |
As pointed out earlier in the thread by Bromic Acid, strike anywhere matches (if you can find them) contain a phosphorus sulphide (P4S3) together with
potassium chlorate and/or manganese dioxide, glue, powdered glass and colouring agent.
From what I can gather the important material here is the "colouring agent".
The references to "high in phosphorus" in the video are incorrect, what he means is "highly phosphorescent", (in UV light). But even this is wrong, he
should really say "highly fluorescent, in UV light". The red matches (safety) that I buy don't glow particularly well in UV, but when the head is
scraped off, the stained wood underneath glows very brightly, just like pink "day-glow" plastic. This possibly suggests it is a rhodamine type dye! I
extracted the dye from some pink "day-glow" plastic, using acetone, it looks just like the extract in the video, but I can't get that intermediate
glow (with bleach). I don't have any H2O2 at the moment, so I can't do any further tests!
Xenoid
[Edited on 11-8-2007 by Xenoid]
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