Sciencemadness Discussion Board
Not logged in [Login ]
Go To Bottom

Printable Version  
 Pages:  1  2
Author: Subject: Ethylchloride preparation
Per
Hazard to Others
***




Posts: 134
Registered: 26-1-2007
Location: Europe
Member Is Offline

Mood: No Mood

[*] posted on 31-1-2007 at 11:59


Ok.
View user's profile View All Posts By User This user has MSN Messenger
garage chemist
chemical wizard
*****




Posts: 1803
Registered: 16-8-2004
Location: Germany
Member Is Offline

Mood: No Mood

[*] posted on 2-2-2007 at 08:53


Ethyl chloride is apparently still available in pharmacies as a local anesthetic ("ice spray", though all of the metal icespray-cans contain something different today). You have to ask specifically for Chloräthyl.
Also enter Chloräthyl into google- you will find common prices for 100ml of it in pharmacies (around 5€).

This would also be a good idea for nitroethane preparation.
You just have to react it with silver nitrite.




www.versuchschemie.de
Das aktivste deutsche Chemieforum!
View user's profile View All Posts By User
Per
Hazard to Others
***




Posts: 134
Registered: 26-1-2007
Location: Europe
Member Is Offline

Mood: No Mood

[*] posted on 3-2-2007 at 05:45


Why doe´s the preparation of nitroethan work with silver nitrate and why doesn´t work it with sodium nitrate?
I can´t imagine that.

Looking for Chloräthyl seems to be a good idea, thank you.

last time I tried to prepare ethyl chloride by adding a 25%HCl solution to a mix of ethyl alcohol and konz. H2SO4.
I heated it a little bit and it envolved white gases, I tried to condense them but it does not work, not even with a ice-alcohol mix.
View user's profile View All Posts By User This user has MSN Messenger
Nicodem
Super Moderator
*******




Posts: 4230
Registered: 28-12-2004
Member Is Offline

Mood: No Mood

[*] posted on 3-2-2007 at 08:26


Quote:
Originally posted by Per
Why doe´s the preparation of nitroethan work with silver nitrate and why doesn´t work it with sodium nitrate?
I can´t imagine that.

I don't know where you heard that nitroethane can be made with silver nitrate, but you can be sure you got it wrong. Silver nitrate and ethyl chloride in DMF or other dipolar solvents would give you ethyl nitrate and not nitroethane. With sodium nitrate you would get no reasonable reaction due to the already mentioned too low difference in the chloride/nitrate nucleophilicity (this problem is overcome in the case of silver salts by the formation of the highly insoluble silver halides – this drives the reaction forward). As already mentioned by Garage chemist, for the preparation of nitroethane from ethyl chloride you would need silver nitrite (AgNO2, also know as silver nitrate(III) as opposed to the nitrates which are salts from the nitrate(V) ion that is NO3(-)).
Though the nitrite anion is way more nucleophilic than the nitrate anion it still requires better leaving groups like the bromide or iodide. Ethyl chloride might give a small yield of nitroethane even with NaNO2 if an optimal solvent is used, but it might also give a lot more of the side product, ethyl nitrite, which tends to condense with nitroethane thus destroying it. I would dare to say that the only reasonable way of preparing nitroethane from ethyl chloride is by using silver nitrite, but on the other side any reasonable person would rather use ethyl bromide or ethyl iodide anyway. Not only because they are several thousand times more reactive, but also because they are much more easy to prepare (or buy given that they are liquids).
Quote:
last time I tried to prepare ethyl chloride by adding a 25%HCl solution to a mix of ethyl alcohol and konz. H2SO4.
I heated it a little bit and it envolved white gases, I tried to condense them but it does not work, not even with a ice-alcohol mix.

The white fume was moist hydrogen chloride gas. Hydrogen chloride only condenses bellow -85°C at normal pressure.




…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)

Read the The ScienceMadness Guidelines!
View user's profile View All Posts By User
Per
Hazard to Others
***




Posts: 134
Registered: 26-1-2007
Location: Europe
Member Is Offline

Mood: No Mood

[*] posted on 3-2-2007 at 11:42


Quote:
Quote:
The white fume was moist hydrogen chloride gas. Hydrogen chloride only condenses bellow -85°C at normal pressure.

I feared that, so it is proved that the method with H2SO4 does not work at all.
View user's profile View All Posts By User This user has MSN Messenger
Random
International Hazard
*****




Posts: 1018
Registered: 7-5-2010
Location: In ur closet
Member Is Offline

Mood: Energetic

[*] posted on 15-2-2011 at 11:56


Is it possible to use 36% ethanol and zinc chloride solution in HCl(aq) to make ethyl chloride or I need to have anhydrous reagents?
View user's profile View All Posts By User
Per
Hazard to Others
***




Posts: 134
Registered: 26-1-2007
Location: Europe
Member Is Offline

Mood: No Mood

[*] posted on 15-2-2011 at 13:56


wouldn't give a reasonable result, but ethanol is OTC as spirit with 94% ethanol. also is't recommended to use anhydrous ZnCl2 and dry HCl.
View user's profile View All Posts By User This user has MSN Messenger
bbartlog
International Hazard
*****




Posts: 1139
Registered: 27-8-2009
Location: Unmoored in time
Member Is Offline

Mood: No Mood

[*] posted on 15-2-2011 at 16:27


I've only done this with IPA (to make 2-chloropropanol), but I think 36% alcohol plus aqueous HCl will give you way too much water for the reaction to proceed. Ideally (to maximize yield) you would want dry HCl gas bubbled into dry ethanol with anhydrous ZnCl2. But unlike some reactions (say, Grignard reagent preparation) you can have some water and still get results. Still at a minimum I would suggest 95% ethanol and anhydrous ZnCl2; you would then have a chance with aqueous HCl. Alternatively, 95% ethanol plus ZnCl2 hydrate plus HCl gas would probably also be dry enough
View user's profile View All Posts By User
~Anthrax~
Harmless
*




Posts: 2
Registered: 16-2-2011
Member Is Offline

Mood: No Mood

[*] posted on 16-2-2011 at 11:36


Unless I'm missing something obvious, surely ethylchloride (chloroethane) can be made from ethanol and phosphorus pentachloride?

CH3CH2OH + PCl5 -----> CH3CH2Cl + POCl3 +HCl

~Anthrax~
View user's profile View All Posts By User
Random
International Hazard
*****




Posts: 1018
Registered: 7-5-2010
Location: In ur closet
Member Is Offline

Mood: Energetic

[*] posted on 16-2-2011 at 14:40


Thanks for the responses, maybe I will try it on test tube scale with those reagents though to obtain even small yield, just to get some experience with that stuff. After that I will try anhydrous ZnCl2, 96% ethanol and 19% HCl(aq).

@Anthrax

http://www.ucc.ie/academic/chem/dolchem/html/comp/ethanol.ht...

Quote:
Halogenation or Substitution of Ethanol with PCl5
Ethanol reacts with phosphorus pentachloride at room temperature to form hydrogen chloride, ethyl chloride (i.e. chloroethane) and phosphoryl chloride.


C2H5OH + PCl5 ==> C2H5Cl + POCl3 + HCl
Ethanol Phosphorus Ethyl Phosphorus Hydrogen
Pentachloride Chloride Pentachloride Chloride


It should be possible.




[Edited on 16-2-2011 by Random]
View user's profile View All Posts By User
Sedit
International Hazard
*****




Posts: 1939
Registered: 23-11-2008
Member Is Offline

Mood: Manic Expressive

[*] posted on 16-2-2011 at 15:24


Random a test tube scale will more then likely provide little information and be dishearting. I tryed the same with EtBr and got nothing from a test tube scale while I got greater then 75% IIRC performing the synthesis at a one mol scale. I feel its a synthesis of inherited losses and a test tube does not produce enough to cover those losses.




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
View user's profile View All Posts By User
Random
International Hazard
*****




Posts: 1018
Registered: 7-5-2010
Location: In ur closet
Member Is Offline

Mood: Energetic

[*] posted on 17-2-2011 at 13:10


Thanks for that information, it would be actually dissapointing to see that test tube scale produces nothing and then loose will to try bigger scale :)
View user's profile View All Posts By User
Nitro-esteban
Harmless
*




Posts: 39
Registered: 10-4-2013
Location: Fifth dimension
Member Is Offline

Mood: inert

[*] posted on 8-6-2013 at 06:15


I mixed 12.5 grams of 80% ethanol with 27.3 grams of 29% HCl and then added a few ml of a concentrated ZnCl2 solution and nothing happened!
View user's profile Visit user's homepage View All Posts By User
Fantasma4500
International Hazard
*****




Posts: 1679
Registered: 12-12-2012
Location: Dysrope (aka europe)
Member Is Offline

Mood: dangerously practical

[*] posted on 26-8-2013 at 03:40


well ofcourse, nitro-esteban..
this reaction relies on anhydrous(-ness?)
so not having it all anhydrous does obviously not work

one approach by what i read here would be H2SO4 98% + NaCl > anh. HCl (g)

anh. HCl(g) + Zn (s) + EtOH (aq) > anh. ZnCl2 (which then reacts with the EtOH to form EtCl)
i dont see anything pointing away from also using Cl2 gas
in which i have discovered can be generated relatively slowly but in high concentration by Na2Cr2O7 + HCl (probably many other dichromates would work, this is because i store dichromate stored in liquid with HCl in a glass bottle)

i must say, tho 'Per' probably isnt around the forum anymore, zinc is very easy to get a hold of
its used for fishing weights, anti corrosion blocks for boats, gutters, car wheel balance pieces, heavy duty battery casings,




~25 drops = 1mL @dH2O viscocity - STP
Truth is ever growing - but without context theres barely any such.

https://en.wikipedia.org/wiki/Solubility_table
http://www.trimen.pl/witek/calculators/stezenia.html
View user's profile View All Posts By User
foxofax474
Harmless
*




Posts: 10
Registered: 17-4-2023
Location: USA
Member Is Offline

Mood: Still processing

[*] posted on 15-3-2024 at 08:41


Quote: Originally posted by Fantasma4500  

one approach by what i read here would be H2SO4 98% + NaCl > anh. HCl (g)

anh. HCl(g) + Zn (s) + EtOH (aq) > anh. ZnCl2 (which then reacts with the EtOH to form EtCl)


Does this method produce EtCl in dissolved in the EtOH or does it bubble out as a gas?




(∩^o^)⊃━☆ the proof is by magic


View user's profile Visit user's homepage View All Posts By User
clearly_not_atara
International Hazard
*****




Posts: 2720
Registered: 3-11-2013
Member Is Offline

Mood: Big

[*] posted on 15-3-2024 at 10:50


According to Raoult's law, the product is most likely a gas, since the rxn is sluggish at low temperatures.

My suggestion: don't make ethyl chloride. Alkylating agents are a very bad starting point for someone new to chemistry.




Quote: Originally posted by bnull  
you can always buy new equipment but can't buy new fingers.
View user's profile View All Posts By User
 Pages:  1  2

  Go To Top