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Author: Subject: iodoacetone
neptunium
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iodoacetone

just made some iodoacetone today... lots of close call on that topics without ever been spot on.....i think

i distilled 0.3 g of iodine with 80 ml of acetone and a drop of HCl....
the first pic is before
and the resulting tear gas...
yes it is a tear gas
iodine coms add itself on the end of the propanone molecule to make just like chlorine and bromine a tear gas .
this one doesnt smell like anything but trust me when i tell you ..IT HURTS!
lots of threat on the subject i know but some how never quite spot on .
everybody has cleaned iodine stain with acetone .
it works great yes ...BUT whoever has done so knows the painful feeling of this smelless compound.
ive done this sinthesis many years ago and the distillate was clear, so..

i probably should distil it one more time when i am all alone in the house so i can evacuate if anything goes wrong...

Bot0nist
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Mood: Streching my cotyledons.

Looks good. Like the pictures. Let us know how the re-distillation goes. Whats the BP?

Do you have any plans in the works for the iodoacetone, other than tear-gassing yourself

Thanks for sharing.
Good luck and be safe.

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AndersHoveland
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Has any member on this forum ever prepared nitroacetone from iodoacetone? (reaction with NaNO2 in DMSO)

[Edited on 17-1-2012 by AndersHoveland]
neptunium
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i dont have any sodium nitrite but....send me 100 bucks and i can fix that!!!!

i am doing the last distillation right now...
get ready for 1 more picture of the painful stuff.....
neptunium
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works every time ! got this yellowish liquid with a bp of about 52C...very painful to even look at !!!

neptunium
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oops ! here it is...sorry fellas..
AirCowPeaCock
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Heat potassium nitrate stump remover! I think it needs 700 some degrees C, its easy.

# BOLD

neptunium
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iodo picrine as far as i know (not much..) hasnt been studied much ...could be interesting...
i have some NaNO3 but i keep it for nitric acid production ...the stump remover is no longer potassium nitrate in my area (US great lakes)

[Edited on 18-1-2012 by neptunium]
Sedit
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That would be excellent for Nitroethane production if mono Nitroacetone was formed with ease.

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neptunium
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i also should point out that instead of HCl i was going to use CuO ... i red somewhere that it was a better yield and accelerate the reaction ..

[Edited on 19-1-2012 by neptunium]

Bot0nist
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Mood: Streching my cotyledons.

 Quote: Originally posted by AirCowPeaCock Heat potassium nitrate stump remover! I think it needs 700 some degrees C, its easy.

That is a proposed (and patented, IIRC) method to nitrite. There is a great thread on the subject titled "<a href="http://www.sciencemadness.org/talk/viewthread.php?tid=52#pid59263">Preparation of ionic nitrites</a> ." The method of reduction with lead, and reduction with carbon both gave me limited success, with low yields. Probably operator error I'm sure.

[Edited on 20-1-2012 by Bot0nist]

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Sedit
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Lead works OK for Sodium Nitrate but I found it to be rather annoying for KNO3 due to a difference in melting point. Separation of KNO2 from KNO3 is easier but the synthesis is harder then with Sodium Nitrate.

Carbon was just to uncontrollable.

Knowledge is useless to useless people...

"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story before."~Maynard James Keenan
Hawkguy
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Does the Iodine/ Acetone mix need to be distilled for the formation of Iodoacetone? I've had some Iodine crystals in Acetone for about a day, and so far, none of the fumes are anything tear - gas like. I tried lowering the pH by adding 2 drops of Sulphuric Acid, to the 50 ml Acetone and 1/3 g Iodine....
quantumcorespacealchemyst
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what are the best ways to get iodoacetone, without acetone exess (azeotrope?) and without getting diiodoacetone (is this pH dependant?, how can the two be made quantitatively without contamination from the other or acetone?)?

 Quote: Originally posted by neptunium i also should point out that instead of HCl i was going to use CuO ... i red somewhere that it was a better yield and accelerate the reaction .. [Edited on 19-1-2012 by neptunium]

what are the effects of these on the halogenation of acetone with regards to pH?

Zn (low acidity)
ZnS
CuS (to make a comparison to CuO)
Pt
Ni (low acidity)
Pd
V2O5
CuI

i am wondering about electrochemistry too; however, the questions i asked are what i am mainly stumped on for now, as i am hoping to learn, goal wise, halogenation/haloformations of ketones.

i am hoping to form a pure halogenated ketone, mainly iodoacetone;
and then after seperation/purification, halogenate it;
with NaOCl and NaOH, to maybe get iododichloromethane / dichloroiodomethane / CHICl2

;and then also try it with diiodoacetone to get diiodochloromethane / chlorodiiodomethane CHCl2I

i also want to get a decent idea of catalytic behaviour from different compounds dependant on pH, i feel confident that would give me things to muse over.

interesting, maybe, is that i tried some halogenation experiments and one of them was with iodine in acetone and UV, i don't remember if i put copper or CuO (edit: CuI, and tryed UV on iodine with copper in acetone, i think) in it. i would have to go back and retroubleshoot it, which is part of my reason for questioning now. one reaction i got was odd as it didn't tear, but smelt real wierd. i only noticed tearing with some combination of aluminum foil in basic acetone with iodine.

with hypochlorite/hydroxide and touching aluminum, it seemed phosgene was formed, not chloroacetone.

edit: i also guess that stoichiometric amounts of iodine and acetone could be mixed with hydroxide solution and then bleach added to haloform to completion. i want to get an understanding from the acidic side of it though, with the pH and catalyst (metal/metal calcogenide) effects.

also, i didn't want to start a new thread of an identical topic unless it was necessary to split the topic.

[Edited on 5-3-2016 by quantumcorespacealchemyst]

[Edited on 5-3-2016 by quantumcorespacealchemyst]

[Edited on 5-3-2016 by quantumcorespacealchemyst]

 Sciencemadness Discussion Board » Fundamentals » Beginnings » iodoacetone Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Responsible Practices   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication Non-chemistry   » Forum Matters   » Legal and Societal Issues