[billnotgatez]

 
   H H           H H      
   | |           | |      
 H-C-C-0-H  +  H-C-C-0-H  
   | |           | |      
   H H           H H      
                          
   catalysts              
  ------------------->    
  standard room temp      
                          
   H H H H                
   | | | |                
 H-C-C-C-C-0-H  +  H-0-H  
   | | | |                
   H H H H                
 

This is just a general thought question.
This is not for any course but for curiosity only.
The questions are --
What catalyst would you use?
Would this process continue to lengthen the chain?
Regards,
Bill

[hmx9123]

Wouldn't you much more easily form diethyl ether?

[billnotgatez]

That is the problem
I rather create longer chain alcohols
Regards,
Bill

[GCT]

Go to the nobel prize memorial site and find Olah's nobel lecture in pdf.  Towards the end of the paper (from what I remember) it should give you some hints on the catalyst to utilize.  This is actually a bad method to synthesize long change alcohols, there are much better ways.  However, Olah's method using superacids, strong electrophile and organometallic reagents to obtain a nonclassical carbocation might work.  In the meanwhile...

You can work with an epoxide to continue lengthing the change with a terminal hydroxyl group.

Hope this helps.

[billnotgatez]

This does not sound like occurring at room temperature
Therefore it is implied that it can not be done at room temperature.
Correct???
If so what reactions can occur at room temperature that would eventually lead to a longer chain compound with only carbon plus hydrogen and / or oxygen. And, what would be the catalyst.

[billnotgatez]

As mentioned above this would be a favored reaction. What would be the catalyst used at room temperature? This is not the result I am interested, but I am curious.

 
   H H             H H    
   | |             | |    
 H-C-C-0-H  +  H-0-C-C-H  
   | |             | |    
   H H             H H    
                          
   catalysts              
  ------------------->    
  standard room temp      
                          
   H H   H H              
   | |   | |              
 H-C-C-0-C-C-H  +  H-0-H  
   | |   | |              
   H H   H H              
 

[AWK]

Let's go one step back. Some bacteria during fermentation of glucose produces butanol (and acetone) instead of ethanol.

[billnotgatez]

http://www.imba.missouri.edu/funded/2002_7.htm

Has a discussion on fermentation to butanol

Can anyone answer either of the catalyst questions?
Keeping in mind room temperature environment

[billnotgatez]

I would consider it a great kindness for someone to post the catalyst in the second equation I posted. Maybe several different ones would be nice --
Remember the room temperature constraint

Regards,
Bill

[AWK]

I doubt if such catalyst exists. You need to break very strong bonds C-H and C-OH.
The weakest bond in ethanol is C-C bond.

[billnotgatez]

Sorry, I was requesting the catalyst in reply #5 not the catalyst in original post of this thread. Reply #1 said that reply #5 was the preferred reaction. Unless the formula in reply #5 is not diethyl ether. In any case let me restate my last request. What catalyst is needed to convert ethanol into diethyl ether at room temperature? If I got the wrong formula in reply #5 please correct me.

[Donaldson Tan]

I dont know any high tech chemistry..

just thinking along this line

ethanol -> ethyl cyanide -> propanoic acid -> propanol -> propyl cyanide -> butanoic acid -> butanol

least this' my 2cents worth
 

[billnotgatez]

Thanks for responding -
Would that mean that we put a minute amount of cyanide in a bottle of ethanol we would eventually get longer chain alcohol. I am still also wondering how we get ether from alcohol.

[GCT]

To get an ether simply perform the williamson ether sythesis.  Add a suitable base, which deprotonates the alcohol and this nucleophile attacks another alcohol to become a base.

2ROH + base equivalence ---> ROR

An alcohol and cyanide?  I'm not sure this will work since it may be the case that cyanide simply removes the alcohol hydrogen to become HCN...very dangerous.

[Donaldson Tan]

Thanks for responding -
Would that mean that we put a minute amount of cyanide in a bottle of ethanol we would eventually get longer chain alcohol. I am still also wondering how we get ether from alcohol.

You would need Lithium Aluminium Hydride to reduce the carboxylic acid to its alcohol.