Sciencemadness Discussion Board

how to syntetize chloroacetone?

its me! - 23-8-2019 at 01:45

My qestion is, how to syntetize chloroacetone? i have been trying to make it but due to lack of informations about its syntesis i wasnt able to make anythink near pure chloroacetone.... and i think someone there may help.

how to syntetize chloroacetone?

its me! - 23-8-2019 at 01:45

My qestion is, how to syntetize chloroacetone? i have been trying to make it but due to lack of informations about its syntesis i wasnt able to make anythink near pure chloroacetone.... and i think someone there may help.

j_sum1 - 23-8-2019 at 02:05

I believe chemplayer has made it. Search his bitchute channel.

Or you could begin your research with this:
http://www.prepchem.com/synthesis-of-chloroacetone/

Disclaimer. I have not done this but it does not appear to b^ too difficult.

[Edited on 23-8-2019 by j_sum1]

wg48temp9 - 23-8-2019 at 02:41

If I remember correctly there is synthesis for chloroacetone in the first book on the "Laboratory Manual of Organic Chemistry" in the library.


[Edited on 8/23/2019 by wg48temp9]

TheMrbunGee - 23-8-2019 at 04:13

Few years ago I dissolved some copper bromide in acetone, it become clear and lachrymatory, I think bromoacetone formed, maybe this can be done with copper chloride?

Edit: There is a reaction between acetone and copper chloride hydrate.


[Edited on 23-8-2019 by TheMrbunGee]

Tsjerk - 23-8-2019 at 05:09

Quote: Originally posted by TheMrbunGee  
Few years ago I dissolved some copper bromide in acetone, it become clear and lachrymatory, I think bromoacetone formed, maybe this can be done with copper chloride?
[Edited on 23-8-2019 by TheMrbunGee]


This works! It does need a little bit of water to start though.

[Edited on 23-8-2019 by Tsjerk]

its me! - 23-8-2019 at 07:26

Quote: Originally posted by Tsjerk  
Quote: Originally posted by TheMrbunGee  
Few years ago I dissolved some copper bromide in acetone, it become clear and lachrymatory, I think bromoacetone formed, maybe this can be done with copper chloride?
[Edited on 23-8-2019 by TheMrbunGee]


This works! It does need a little bit of water to start though.

[Edited on 23-8-2019 by Tsjerk]


Thanks! That sound much easier than the chlorine method.

CuReUS - 23-8-2019 at 08:52

just electrolyse a mixture of salt water and acetone :)

fusso - 23-8-2019 at 08:52

Quote: Originally posted by Tsjerk  
Quote: Originally posted by TheMrbunGee  
Few years ago I dissolved some copper bromide in acetone, it become clear and lachrymatory, I think bromoacetone formed, maybe this can be done with copper chloride?
[Edited on 23-8-2019 by TheMrbunGee]


This works! It does need a little bit of water to start though.

[Edited on 23-8-2019 by Tsjerk]
What's the mechanism? Is there a name (like grignard rxn) for the rxn?

karlos³ - 23-8-2019 at 09:02

Quote: Originally posted by fusso  
Quote: Originally posted by Tsjerk  
Quote: Originally posted by TheMrbunGee  
Few years ago I dissolved some copper bromide in acetone, it become clear and lachrymatory, I think bromoacetone formed, maybe this can be done with copper chloride?
[Edited on 23-8-2019 by TheMrbunGee]


This works! It does need a little bit of water to start though.

[Edited on 23-8-2019 by Tsjerk]
What's the mechanism? Is there a name (like grignard rxn) for the rxn?

It's a simple alpha-halogenation of ketones.

Best would be to use a solvent system of 1:1 ethyl acetate and chloroform for the CuCl2.

[Edited on 23-8-2019 by karlos³]

Metacelsus - 23-8-2019 at 14:33

Ethyl acetate may also be chlorinated under those conditions, so I wouldn't use it.

TheMrbunGee - 23-8-2019 at 17:36




I am actually exited for these reactions, can other substances be halogenated by this process? This could be more useful than you can imagine.

[Edited on 24-8-2019 by TheMrbunGee]

AvBaeyer - 23-8-2019 at 19:36

CuCl2 does chlorinate acetone quite slowly. It works best with a LiCl catalyst which works through the Li2CuCl4 complex. Jay Kochi published initial studies on this reaction in JACS in the 1950's or 60's. There were a number of follow on papers by Kochi and others. A Google scholar search will lead you to the references. [Just saw that Tsjerk posted a link to the initial paper above.]

CuBr2 is a much more reactive halogenation reagent for ketones though its expense is a drawback except in special cases. I used it quite a bit in years past. Ethyl acetate is a useful solvent and suffers no detectable halogenation. CCl4 was a preferred solvent for the reaction. If you search cupric bromide ketone halogenations on Google you should find several pertinent references.

Perhaps the best halogenation (bromination) process for ketones in the home lab is 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in CH2Cl2 using a trace of acid catalysis. I have run many of these reactions and they work well. N-Bromosuccinimide will also work. TCCA reportedly works for chloroketones though I have not had great success. Again, several useful references can be found with a Google search.

AvB

Simoski - 23-8-2019 at 22:20

At the simplest level, bubble elemental chlorine gas through acetone until it will accept no more.

It can be used as an area denial weapon, stinks like hell and hangs around for days.

To neuteralise / capture strategic facilities. Not sure the exact death rate but the guy who told me about it said very low, like almost zero fatalities but all civilians would exit the area from the terrible choking fumes. More like teargas on steroids than a banned chemical weapon.





[Edited on 24-8-2019 by Simoski]

Metacelsus - 24-8-2019 at 04:52

Quote: Originally posted by Simoski  
At the simplest level, bubble elemental chlorine gas through acetone until it will accept no more.


If you do that, the reaction won't stop at monochloroacetone.

its me! - 24-8-2019 at 08:50

Quote: Originally posted by Metacelsus  
Quote: Originally posted by Simoski  
At the simplest level, bubble elemental chlorine gas through acetone until it will accept no more.


If you do that, the reaction won't stop at monochloroacetone.


How do i know when to stop then?

S.C. Wack - 24-8-2019 at 10:10

Reading through 3 existing chloroacetone threads was a sad nostalgic parade of people who are gone.
Quote: Originally posted by its me!  
How do i know when to stop then?


When the correct amount of CaCl2 has formed.
Quote: Originally posted by wg48temp9  
If I remember correctly there is synthesis for chloroacetone in the first book on the "Laboratory Manual of Organic Chemistry" in the library.


I've been waiting for a reason to bring up this unique little book (An Advanced Laboratory Manual of Organic Chemistry, 1923) for some time:

https://books.google.com/books?id=zB5IAAAAIAAJ&pg=PA19

karlos³ - 24-8-2019 at 11:25

I can vouch for the use of NBS for the bromination of ketones, it is a very simple, well to handle, and is quick and thorough, quantitative yields can even be had when p-toluenesulfonic acid is used as catalyst(10% as molar equivalent to NBS), either in acetonitrile as solvent or without(but then sudden exothermia can occur, so cooling is advised at the start).
I have brominated many ketones with this method, always in high to quantitative yields.
The use of other acid catalysts will result in lower yields(also experienced that, using methanesulfonic acid).