tahallium
Harmless
Posts: 41
Registered: 24-2-2020
Location: Tunisia
Member Is Offline
|
|
Ethanol to chloroform
So I did the haloform reaction to make chloroform before and it's really easy but the yield is TERRIBLE acetone is so expensive and using so much
bleach isn't a good idea cuz chloroform is quite soluble
Can I make chloroform using ethanol?? I have two ideas:
Bubbling chlorine into ethanol to make chloral and adding water+sodium hydroxide to make chloral hydrate it'll hydrolyze immediately to chloroform and
sodium chloride I think
Or use tcca, sodium dcca to make the haloform reaction using ETHANOL??
Please tell me if I'm wrong
|
|
|
Abromination
Hazard to Others
Posts: 432
Registered: 10-7-2018
Location: Alaska
Member Is Offline
Mood: 1,4 tar
|
|
As far as I am aware, most people stick with the haloform reaction for the production of ethanol. In most places, both sodium and calcium hypochlorite
as well as acetone are dead cheap. Chloroform doesn't find too many uses in labs today due to its toxicity and tendency to oxidize to phosgene under
UV light and air exposure, so make sure to stabilize your product with 2% ethanol and keep it in an amber bottle covered in aluminium foil. Given
this, it may be better to purchase an alternative solvent such as DCM for general use and prepare chloroform using the haloform reaction as needed.
Anyways, chloral hydrate does indeed react with a mole of sodium hydroxide to form chloroform as well as sodium formate and water (not NaCl). There is
an extensive thread on the synthesis of chloral hydrate, including both the chlorination of ethanol as well as a method using trichloroethylene. It is
worth a read, but shows how messy the chlorination is and how the trichloroethylene path is way more expensive than making chloroform out of a
hypochlorite and acetone.
https://www.sciencemadness.org/whisper/viewthread.php?tid=25...
I don't see how ethanol would react with TCCA to form chloroform, and the haloform requires a ketone to be halogenated. Ethanol is not a ketone.
Besides, the haloform takes place in basic medium, TCCA is an acid.
List of materials made by ScienceMadness.org users:
https://docs.google.com/spreadsheets/d/1nmJ8uq-h4IkXPxD5svnT...
--------------------------------
Elements Collected: H, Li, B, C, N, O, Mg, Al, Si, P, S, Fe, Ni, Cu, Zn, Ag, I, Au, Pb, Bi, Am
Last Acquired: B
Next: Na
-------------- |
|
|
Ubya
International Hazard
Posts: 1247
Registered: 23-11-2017
Location: Rome-Italy
Member Is Offline
Mood: I'm a maddo scientisto!!!
|
|
Quote: Originally posted by Abromination  | As far as I am aware, most people stick with the haloform reaction for the production of ethanol. In most places, both sodium and calcium hypochlorite
as well as acetone are dead cheap. Chloroform doesn't find too many uses in labs today due to its toxicity and tendency to oxidize to phosgene under
UV light and air exposure, so make sure to stabilize your product with 2% ethanol and keep it in an amber bottle covered in aluminium foil. Given
this, it may be better to purchase an alternative solvent such as DCM for general use and prepare chloroform using the haloform reaction as needed.
Anyways, chloral hydrate does indeed react with a mole of sodium hydroxide to form chloroform as well as sodium formate and water (not NaCl). There is
an extensive thread on the synthesis of chloral hydrate, including both the chlorination of ethanol as well as a method using trichloroethylene. It is
worth a read, but shows how messy the chlorination is and how the trichloroethylene path is way more expensive than making chloroform out of a
hypochlorite and acetone.
https://www.sciencemadness.org/whisper/viewthread.php?tid=25...
I don't see how ethanol would react with TCCA to form chloroform, and the haloform requires a ketone to be halogenated. Ethanol is not a ketone.
Besides, the haloform takes place in basic medium, TCCA is an acid. |
ethanol gets oxidized to acetaldehyde, and that reacts again to form chloroform.
so you'll need double the amount of bleach for the same amount of product.
what you could do is make calcium hypoclorite (if you can't buy any) by running chlorine gas on moist calcium hydroxide, you can then use it as a more
concentrated form of bleach
---------------------------------------------------------------------
feel free to correct my grammar, or any mistakes i make
---------------------------------------------------------------------
|
|
|
Abromination
Hazard to Others
Posts: 432
Registered: 10-7-2018
Location: Alaska
Member Is Offline
Mood: 1,4 tar
|
|
| Quote: Originally posted by Ubya | | Quote: Originally posted by Abromination | As far as I am aware, most people stick with the haloform reaction for the production of ethanol. In most places, both sodium and calcium hypochlorite
as well as acetone are dead cheap. Chloroform doesn't find too many uses in labs today due to its toxicity and tendency to oxidize to phosgene under
UV light and air exposure, so make sure to stabilize your product with 2% ethanol and keep it in an amber bottle covered in aluminium foil. Given
this, it may be better to purchase an alternative solvent such as DCM for general use and prepare chloroform using the haloform reaction as needed.
Anyways, chloral hydrate does indeed react with a mole of sodium hydroxide to form chloroform as well as sodium formate and water (not NaCl). There is
an extensive thread on the synthesis of chloral hydrate, including both the chlorination of ethanol as well as a method using trichloroethylene. It is
worth a read, but shows how messy the chlorination is and how the trichloroethylene path is way more expensive than making chloroform out of a
hypochlorite and acetone.
https://www.sciencemadness.org/whisper/viewthread.php?tid=25...
I don't see how ethanol would react with TCCA to form chloroform, and the haloform requires a ketone to be halogenated. Ethanol is not a ketone.
Besides, the haloform takes place in basic medium, TCCA is an acid. |
ethanol gets oxidized to acetaldehyde, and that reacts again to form chloroform.
so you'll need double the amount of bleach for the same amount of product.
what you could do is make calcium hypoclorite (if you can't buy any) by running chlorine gas on moist calcium hydroxide, you can then use it as a more
concentrated form of bleach |
That would work, I think Vogel has some notes on the procedure. Basic haloform is still probably cheaper.
List of materials made by ScienceMadness.org users:
https://docs.google.com/spreadsheets/d/1nmJ8uq-h4IkXPxD5svnT...
--------------------------------
Elements Collected: H, Li, B, C, N, O, Mg, Al, Si, P, S, Fe, Ni, Cu, Zn, Ag, I, Au, Pb, Bi, Am
Last Acquired: B
Next: Na
-------------- |
|
|
Ubya
International Hazard
Posts: 1247
Registered: 23-11-2017
Location: Rome-Italy
Member Is Offline
Mood: I'm a maddo scientisto!!!
|
|
i can buy 1L of acetone for 2 euros, and calcium hydroxide is impossible to find here, maybe for tahallium is still cheaper going a different route
even if for us would be more work and more expensive
---------------------------------------------------------------------
feel free to correct my grammar, or any mistakes i make
---------------------------------------------------------------------
|
|
|
MadHatter
International Hazard
Posts: 1346
Registered: 9-7-2004
Location: Maine
Member Is Offline
Mood: Enjoying retirement
|
|
Pool Schock
This could work for you as some pool shocks
are calcium hypochlorite. Usually found with
other pool chlorinators such as TCCA.
From opening of NCIS New Orleans - It goes a BOOM ! BOOM ! BOOM ! MUHAHAHAHAHAHAHA !
|
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
