|
|
| Author |
Message |
thenewrunne
Chemically Balanced
|
| Joined: 26 Mar 2005 |
| Posts: 45 |
|
914.96 Points
|
|
|
n-butylamine, specific name? is it watched?
Fri Apr 08, 2005 4:42 am |
 |
|
For synthesis which specify "n-butylamine" is that a special chemical, or can it be used interchangibly with "di-n-butylamine" or "tri-n-butylamine" etc.
Is it a watched chemical or suspicious in any way? |
|
| Back to top |
|
 |
ApprenticeCook
DILLIGAF
|
| Joined: 12 Feb 2005 |
| Posts: 162 |
| Location: Australia |
8486.38 Points
|
|
|
Fri Apr 08, 2005 5:48 am |
|
|
as a reagent? no...
If it requires n-butylamine that is mono... ie BuNH2
di and tri have more amino groups attached...
What synthesis are you attempting? let us know the details and we may be able to help....
To my knowledge butylamine isnt listed.
-AC |
|
| Back to top |
|
|
thenewrunne
Chemically Balanced
|
| Joined: 26 Mar 2005 |
| Posts: 45 |
|
914.96 Points
|
|
|
Fri Apr 08, 2005 7:13 am |
|
|
SWIM will be attempting the phenyl-2-nitropropene synth as above. He was thinking of just substituting ammonium acetate for the n-butylamine? are they basically interchangeable in this reaction? Are there any other ammonium's that can be used? Such as ammonium carbonate? Any quick way to switch ammonium carbonate to acetate? (SWIM has GAA)
| Quote: |
Phenyl-2-nitropropene (J. Org. Chem. 1950, Vol 15, p. 
One mole of benzaldehyde, one mole of nitroethane, 5 mL of n-butylamine and 100 mL of absolute ethanol (no water!) were refluxed for 8 hours in a 1000 mL round bottom flask. When the contents were cooled and stirred a heavy, yellow, crystalline mass formed immediately. After recrystallization from absolute ethanol, the 1-phenyl-2-nitropropene weighed 105 g. Yield: 64 %. M.P.: 65 °C
or
Procedure (By Dreamer)
To 55 g (0.5mol) Benzaldehyde in a 500ml Flask were added 40 g (0.5mol) Nitroethane and 10ml Cyclohexylamine. All was refluxed for 6h on a water bath. The result were 2 layers. One orange layer at the bottom with phenyl-2-nitropropene and a clear layer at the top with cyclohexylamine and maybe a little bit (~1ml) of H20. 50ml of H2O were added and then sucked off with a pipette until the phenyl-2-nitro-propene crystallized (it crystallized when it came in touch with air in presence of 15ml H2O). I added 200ml 95% denaturated ethanol to the orange crystals. The color of the now needle-like crystals changed from orange to white-yellow. The crystals were filtered. Yield 65 g, 78% of theory.
or
Phenyl-2-nitropropene (J. Chin. Chem. Soc. 2002, 49, 505-508)
A solution of benzaldehyde (6.4 g) and ammonium acetate (1.0 g) in nitroethane (20 mL) was heated to reflux for 5 h. On cooling, after removal of the solvent, the residue was purified by column chromatography on silica gel 60 N (neutral; hexane-chloroform, 2:1, v/v), then recrystallized from hexane and gave 1-phenyl-2-nitropropene as a light yellow crystals weighing 6.2g (63%), mp 71-73°C.
|
They all look pretty much the same.. SWIM will just be careful of mol weight adjustments of course.
Taking the product and then reducing it via the Ushibara nickle/aluminum catalyst. |
|
| Back to top |
|
|
brain
Linguist Extraordinaire
|
| Joined: 08 Mar 2005 |
| Posts: 143 |
|
2405.16 Points
|
|
|
Fri Apr 08, 2005 4:47 pm |
|
|
n-dutylamine, di-n-butylamine can be used, dont know if tri- will work
 |
|
| Back to top |
|
|
ApprenticeCook
DILLIGAF
|
| Joined: 12 Feb 2005 |
| Posts: 162 |
| Location: Australia |
8486.38 Points
|
|
|
Sat Apr 09, 2005 7:31 am |
|
|
What have i heard about dreamers synthesis reports..... hmm there were words about this over at WD i think.
-AC |
|
| Back to top |
|
|
Star-light
Blacklight bulb
|
| Joined: 26 Mar 2005 |
| Posts: 77 |
|
2681.50 Points
|
|
|
Sun Apr 10, 2005 4:40 pm |
|
|
| thenewrunne wrote: |
|
ammonium acetate for the n-butylamine? are they basically interchangeable in this reaction? Are there any other ammonium's that can be used?
|
Ammonium acetate can be used in this reaction instead of n-butylamine. Ammonium acetate tends to give a rather dirty product which can be difficult to crystallize without a seed crystal. Methylamine acetate performs better (you can make it from methylamine.HCL in methanol and KOH in methanol, followed by filtration and addition of CH3COOH OR methylamine.HCL in methanol and Potassium Acetate in methanol followed by filtration).
You would probably have to make you Methylamine.HCL yourself as it is a watched chemical. |
|
| Back to top |
|
|
IndoleAmine
Dreamreader Deluxe
|
| Joined: 09 Feb 2005 |
| Posts: 681 |
| Location: Bahamas |
18717.10 Points
|
|
|
: n-butylamine, specific name? is it watched?
Thu May 26, 2005 7:42 am |
|
|
1,2-ethylenediamine (2HN-CH=CH-NH2) is excellent in this case, provided it is used with excess GAA which also acts as a solvent or, even better, if you prepare it beforehand, and isolate it as pure crystalline salt which can be dried in a dessicator and weighed out to the exact needed amount, so desired....
It is further unwatched (used by the gallon in electrolytic nickel plating or something like that), not really expensive and gives the best results (besides MeAm) for this specific substrate IMO, and for sure the cleanest I've ever seen (and believe me SWIA has tried many of them knoevenagel catalysts there are)
Hope this is comprehensive enough to match your high standards you apply to a MODERATOR post, start-light? 
indole_amine |
|
| Back to top |
|
|
joe_aldehyde
huxleys associate
|
| Joined: 06 Apr 2005 |
| Posts: 310 |
|
5653.90 Points
|
|
|
Mon May 30, 2005 6:45 pm |
|
|
hum, seriously i_a, one time you claim that BuNH2 is the best knoevenagel catalyst, next post you say it's MeNH2...
since you also claim to have tried so many of them, why not give us a short list with subjectively measured yields? i'm especially interested in ethanolamine, triethanolamine. |
|
| Back to top |
|
|
Senfgas
|
| Joined: 26 May 2005 |
| Posts: 10 |
|
267.70 Points
|
|
|
Mon May 30, 2005 7:53 pm |
|
|
In my experiense, each catalyst is the best for a specific substrate.
Hydroxamines are good catalyst for making nitroalcohols, not nitrostyrenes. |
|
| Back to top |
|
|
joe_aldehyde
huxleys associate
|
| Joined: 06 Apr 2005 |
| Posts: 310 |
|
5653.90 Points
|
|
|
Mon May 30, 2005 7:56 pm |
|
|
but nitroalcohols are also nice to have  PPA -> 4-MAR for example. shake n bake! |
|
| Back to top |
|
|
Senfgas
|
| Joined: 26 May 2005 |
| Posts: 10 |
|
267.70 Points
|
|
|
Mon May 30, 2005 8:01 pm |
|
|
| thenewrunne want to make p2np from benzaldehyd not nitroalcohol, I thought. |
|
| Back to top |
|
|
|
|
|
Forums
Rhodium
The Hive
Shop
Profile
Log in
Register
Log in to check your private messages
2975