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

Printable Version  
Author: Subject: Ethyl Isopropyl Ether
TheChemiKid
National Hazard
****




Posts: 493
Registered: 5-8-2013
Location: ̿̿ ̿̿ ̿'̿'̵͇̿̿з=༼ ▀̿̿Ĺ̯̿̿▀̿ ̿ ༽
Member Is Offline

Mood: No Mood

[*] posted on 31-12-2013 at 05:35
Ethyl Isopropyl Ether


I was looking to make the lesser known ether Ethyl Isopropyl Ether. I am looking for this because it has a higher boiling point than Diethyl Ether.

I was hoping to make it with the Williamson ether synthesis if this is possible.
This may not work, but if it does, I think the reaction would go like this: C2H5Br + C3H8OH =NaOH=> C3H8OC2H5 + H2O + NaBr

I have a question about this.
Does Ethyl Isopropyl Ether form peroxides? If so, do I try to prevent this by the same methods as I would with Diethyl Ether?




When the police come


\( * O * )/ ̿̿ ̿̿ ̿'̿'̵͇̿̿з=༼ ▀̿̿Ĺ̯̿̿▀̿ ̿ ༽
View user's profile View All Posts By User
macckone
International Hazard
*****




Posts: 2134
Registered: 1-3-2013
Location: Over a mile high
Member Is Offline

Mood: Electrical

[*] posted on 31-12-2013 at 07:42


Yes, it forms peroxides.
More so than ethyl ether but not as bad as isopropyl ether.
Keep in mind you may get some degree of disproportionation
so the BP might not be as stable as ethyl ether or isopropyl ether.
View user's profile View All Posts By User
12thealchemist
Hazard to Others
***




Posts: 181
Registered: 1-1-2014
Location: The Isle of Albion
Member Is Offline

Mood: Rare and Earthy

[*] posted on 1-1-2014 at 02:49


Are you sure that you've got the Williamson synthesis right? I thought it was an alkoxide + halogenoalkane -> ether + salt. Correct me if am wrong, but the NaOH could hydrolyse the ethyl bromide, as a side reaction. However, it would be good if your method did work. It would make ether synthesis much easier, since alkoxides require elemental alkali metals, which are expensive and hard to get hold of.
Also, how about this?: http://www.scienceforums.net/topic/31282-can-someone-critiqu...
View user's profile Visit user's homepage View All Posts By User
Nicodem
Super Moderator
Thread Moved
1-1-2014 at 10:56
Aconite
Harmless
*




Posts: 11
Registered: 23-12-2013
Member Is Offline

Mood: No Mood

[*] posted on 3-1-2014 at 20:53


- This is unlikely to work without very high temperatures (too high for ethyl bromide to remain as a liquid unless under pressure)... and even then, doubtful. The equilibrium lies almost completely towards the alcohol and hydroxide. Typically alkoxides are prepared as salts by dissolving a reactive metal (sodium, potassium, lithium) into the anhydrous alcohol.
- The ether would form peroxides on standing in air.
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 3-1-2014 at 23:46


Could aluminum or magnesium alkoxide be used?
View user's profile View All Posts By User
Organikum
resurrected
*****




Posts: 2267
Registered: 12-10-2002
Location: Europe
Member Is Offline

Mood: lonely

[*] posted on 4-1-2014 at 10:26


http://books.google.de/books?id=FETzRWMGt3YC&pg=PA354&am...



Irgendwas is ja immer
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 4-1-2014 at 15:21


Quote: Originally posted by Organikum  
http://books.google.de/books?id=FETzRWMGt3YC&pg=PA354&am...


Page is unavailable to me.
View user's profile View All Posts By User
bfesser
Resident Wikipedian
*****




Posts: 2114
Registered: 29-1-2008
Member Is Offline

Mood: No Mood

[*] posted on 4-1-2014 at 15:38


Try <a href="http://books.google.com/books?id=FETzRWMGt3YC&pg=PA354&lpg=PA354&dq=Ethyl+Isopropyl+Ether" target="_blank">this</a> <img src="../scipics/_ext.png" />.



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 4-1-2014 at 16:22


Quote: Originally posted by bfesser  
Try <a href="http://books.google.com/books?id=FETzRWMGt3YC&pg=PA354&lpg=PA354&dq=Ethyl+Isopropyl+Ether" target="_blank">this</a> <img src="../scipics/_ext.png" />.


Thanks, it works now. So is aluminum alkoxide a strong enough base? Alkali metal alkoxides are probably much stronger and maybe it's meant for them. Aluminum alkoxides are much cheaper fir a home chemist.
View user's profile View All Posts By User
DraconicAcid
International Hazard
*****




Posts: 3952
Registered: 1-2-2013
Location: The tiniest college campus ever....
Member Is Online

Mood: Semi-victorious.

[*] posted on 4-1-2014 at 16:36


You don't want your alkoxide to act as a base; you want it to act as a nucleophile. I would hazard a guess that the aluminum alkoxide would be a poorer nucleophile than the the potassium or sodium alkoxide, since there'd be more covalent character to the metal-oxygen bond. I don't know if this would stop your reaction from happening.



Please remember: "Filtrate" is not a verb.
Write up your lab reports the way your instructor wants them, not the way your ex-instructor wants them.
View user's profile View All Posts By User
UnintentionalChaos
International Hazard
*****




Posts: 1454
Registered: 9-12-2006
Location: Mars
Member Is Offline

Mood: Nucleophilic

[*] posted on 4-1-2014 at 16:43


Aluminum is an inappropriate metal choice here. It's oxide is amphoteric and it's halides are powerfully lewis acidic. Aluminum halides will react with alkali alkoxides to form aluminum alkoxides, which is the opposite of what you want happening. Magnesium might work but probably not as well as an alkali alkoxide.



Department of Redundancy Department - Now with paperwork!

'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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 4-1-2014 at 17:13


Yeah, so magnesium is my best bet then. I might try it once I find a way to make alkyl chlorides with easily obtained stuff.
View user's profile View All Posts By User

  Go To Top