September 27, 2024, 03:56:07 PM
Forum Rules: Read This Before Posting


Topic: Ethyne+NaOH+Acetone  (Read 3714 times)

0 Members and 1 Guest are viewing this topic.

Offline TyPie

  • Regular Member
  • ***
  • Posts: 25
  • Mole Snacks: +3/-2
Ethyne+NaOH+Acetone
« on: February 11, 2014, 04:46:49 PM »
Not really sure how to ask this, but I read that ethyne+acetone in the presence of NaOH would yield 3-butyn-2-ol.  When I think of organic chemistry, I usually think of wet chemistry, but ethyne is gas at atmospheric conditions, but exists as a solid commonly as calcium carbide.  Is it possible to react calcium carbide in acetone to get 3-butyn-2-ol?  I have a feeling that it would be a completely different mechanism, because of the 2nd group calcium. 

Offline Archy12345

  • Regular Member
  • ***
  • Posts: 49
  • Mole Snacks: +2/-0
  • Gender: Male
Re: Ethyne+NaOH+Acetone
« Reply #1 on: February 11, 2014, 06:46:43 PM »
This could potentially work only if there is water present in the system for the calcium carbide to react with to produce the ethyne. I'm assuming the sodium hydroxide is aqueous. Most likely it would not work, though. I don't imagine the Calcium ions would interfere but there are a few other complications.

Offline TyPie

  • Regular Member
  • ***
  • Posts: 25
  • Mole Snacks: +3/-2
Re: Ethyne+NaOH+Acetone
« Reply #2 on: February 11, 2014, 07:16:57 PM »
Thanks for the quick response Archy,

I was thinking about mixing with water too, but I have no clue how "bubble chemistry" works.  I say this, because I know calcium carbide alone becomes ethyne (g) when it reacts with water by itself.  I worry that the ethyne would leave before undergoing the complete reaction with the acetone if it is possible. 

Offline Archy12345

  • Regular Member
  • ***
  • Posts: 49
  • Mole Snacks: +2/-0
  • Gender: Male
Re: Ethyne+NaOH+Acetone
« Reply #3 on: February 11, 2014, 11:33:12 PM »
I'm unfamiliar with this reaction and how quickly it reacts, but I'm assuming it's a slow one.
If you have a pressure gauge then you could pressurize it and calculate how much ethyne is dissolved in the solution. But I can pretty much tell you that bubbling it through is not an efficient way to carry out the reaction.

Offline TyPie

  • Regular Member
  • ***
  • Posts: 25
  • Mole Snacks: +3/-2
Re: Ethyne+NaOH+Acetone
« Reply #4 on: February 12, 2014, 01:58:47 AM »
Thanks for your help :)

The reaction that I'm looking at is on page 236.  It's not exactly that one, but It's similar. http://journal.scconline.org/pdf/cc1974/cc025n04/p00203-p00231.pdf

From my knowledge, ethyne is stored in a gas tank, and people store it with acetone to keep it from combusting I think.  Are you supposed to be able to run the gas tank through a line into NaOH (s)?  This just doesn't sound like any reaction I've ever seen.  :\ 

Offline Enthalpy

  • Chemist
  • Sr. Member
  • *
  • Posts: 4036
  • Mole Snacks: +304/-59
Re: Ethyne+NaOH+Acetone
« Reply #5 on: February 13, 2014, 02:18:37 PM »
Acetylene is stored in acetone because it is not explosive in that form, as an exception.
You won't get it industrially in gas bottles.

Sponsored Links