1-Phenyl-2-nitropropene (P2NP) Video Synthesis From Benzaldehyde and Nitroethane. Henry Reaction.

[wael gano]

I tried the synthesis and I ended up with this solution. What is wrong with this? What do I do?
7.5 ml of benzaldehyde
6 ml of nitro ethane
3 ml of glacial acetic acid
1.8ml cyclohexylamine
Heating for 3,5 hours
What is wrong with the product of the reaction, something like the unreacted amine?

 

[UWe9o12jkied91d]

I tried the synthesis and I ended up with this solution. What is wrong with this? What do I do?
7.5 ml of benzaldehyde
6 ml of nitro ethane
3 ml of glacial acetic acid
1.8ml cyclohexylamine
Heating for 3,5 hours
What is wrong with the product of the reaction, something like the unreacted amine? View attachment 20179

wael ganooof, now I read carefully...you should use equal volumes of nitro benzo, that in your picture is unreacted benzaldehyde ofcourse

 

[777m]

possibly too long reaction time and amine degraded, plus it's about 3x the amine needed for that scale

UWe9o12jkied91dSo what do you think the real rates should be?

 

[UWe9o12jkied91d]

So what do you think the real rates should be?

777mproportions? equal volumes aldehyde alkene

 

[777m]

When I do it, an orange color comes out and the crystals do not form at all. And I definitely think it's because of the nitroethane purity she synthesized from sodium ethyl sulfate.

 

[JoshL1221]

someone know about try catalyst with ammonium carbonate? in presence of acetic acid, how much acetic acid is used if the book say "an excess", thanks

 

[flyhigh2]

Need help!!!!
I tried the synthesis and I ended up with this solution. What is wrong with this? What do I do?
50 ml of benzaldehyde
50 ml of nitro ethane
10 ml of glacial acetic acid
12.5 ml n-butly-amine
75ml ipa
and Heating for 6 hours at 50C i ended up with reddish orange liquid, i froze it for 12hrs but crystal didn't form

flyhigh21) use open glass which has access to air
2) rub the walls of glass by a stick to initiate crystallization
3) Add some crystalls of P2NP if you have it

 

[GhostChemist]

Need help!!!!
I tried the synthesis and I ended up with this solution. What is wrong with this? What do I do?
50 ml of benzaldehyde
50 ml of nitro ethane
10 ml of glacial acetic acid
12.5 ml n-butly-amine
75ml ipa
and Heating for 6 hours at 50C i ended up with reddish orange liquid, i froze it for 12hrs but crystal didn't form

flyhigh21) use open glass which has access to air
2) rub the walls of glass by a stick to initiate crystallization
3) Add some crystalls of P2NP if you have it

 

[MisterAnonymous]

I bought 50L of Nitroethane I'll have it in 2 weeks i will add it to the Reagents section so everyone can buy it for the people who want

 

[Manisj@1290]

I Successfully synthesized nitroethane but not pure can I make p2np with impure nitroethane.

 

[HIGGS BOSSON]

I Successfully synthesized nitroethane but not pure can I make p2np with impure nitroethane.

Manisj@1290Depends on how dirty your nitroethane is. Try putting a few grams in the microwave as an experiment.

 

[Manisj@1290]

Depends on how dirty your nitroethane is. Try putting a few grams in the microwave as an experiment.

HIGGS BOSSONAfter diatalltion I neither wash it with water nor dry it, because I have not a fractional condenser. That's why I feel that my distal relation is not pure.

Can I make p2np with nitroethane

 

[Manisj@1290]

After diatalltion I neither wash it with water nor dry it, because I have not a fractional condenser. That's why I feel that my distal relation is not pure.

Can I make p2np with nitroethane

Manisj@1290My nitroethane is like this can I make p2np with us

 

[wael gano]

My nitroethane is like this can I make p2np with us

Manisj@1290The picture shows nitroethane suspended in the middle
Nitroethane is heavier than water and is supposed to sink to the bottom. This indicates that there is alcohol dissolved in the water. Did you use non-dry sodium ethyl sulfate crystals moistened with some alcohol?
How much did you get?

 

[Manisj@1290]

The picture shows nitroethane suspended in the middle
Nitroethane is heavier than water and is supposed to sink to the bottom. This indicates that there is alcohol dissolved in the water. Did you use non-dry sodium ethyl sulfate crystals moistened with some alcohol?
How much did you get?

wael ganoI was used ethanol for purify my sodium ethyl Sulfate.

If the bottom part is ethanol, will there be any problem with P2np synthesis ?

 

[wael gano]

I was used ethanol for purify my sodium ethyl Sulfate.

If the bottom part is ethanol, will there be any problem with P2np synthesis ?

Manisj@1290In theory there is no problem with ethanol with P2NP
But here you find the problem: ethanol and impure nitroethane cause a problem when distilling the nitroethane after separating it from water. The second distillation, in which you find a colorless, transparent liquid.
But in the presence of ethanol, you will not be able to purify nitroethane because the dirt remains after the second distillation
Note: In the presence of ethanol, you will not be able to determine the amount of nitroethane in the reaction of p2np with benzaldehyde

 

[wael gano]

I was used ethanol for purify my sodium ethyl Sulfate.

If the bottom part is ethanol, will there be any problem with P2np synthesis ?

Manisj@1290This was not the case in your work
You use a lot of solvents and they are expensive
Why do you clean sodium ethyl sulfate? Did you use sodium carbonate for neutralization? Is it sodium sulfate impurities? It does not matter in cleaning. Just keep it with sodium ethyl sulfate and calculate the double quantity. Get rid of the ethanol before distilling the nitroethane. Put the sodium chloride salt in the water. Separate the nitroethane and dry it with silica gel or any. Dryer and re-distillation will come to 116 degrees
You can extract the water phase as diethyl ether
By doing this you will save more solvent

 

[Manisj@1290]

This was not the case in your work
You use a lot of solvents and they are expensive
Why do you clean sodium ethyl sulfate? Did you use sodium carbonate for neutralization? Is it sodium sulfate impurities? It does not matter in cleaning. Just keep it with sodium ethyl sulfate and calculate the double quantity. Get rid of the ethanol before distilling the nitroethane. Put the sodium chloride salt in the water. Separate the nitroethane and dry it with silica gel or any. Dryer and re-distillation will come to 116 degrees
You can extract the water phase as diethyl ether
By doing this you will save more solvent

wael ganoI will try to separate

 

[Manisj@1290]

This was not the case in your work
You use a lot of solvents and they are expensive
Why do you clean sodium ethyl sulfate? Did you use sodium carbonate for neutralization? Is it sodium sulfate impurities? It does not matter in cleaning. Just keep it with sodium ethyl sulfate and calculate the double quantity. Get rid of the ethanol before distilling the nitroethane. Put the sodium chloride salt in the water. Separate the nitroethane and dry it with silica gel or any. Dryer and re-distillation will come to 116 degrees
You can extract the water phase as diethyl ether
By doing this you will save more solvent

wael ganoThanks for guidance

 

[wael gano]

This was not the case in your work
You use a lot of solvents and they are expensive
Why do you clean sodium ethyl sulfate? Did you use sodium carbonate for neutralization? Is it sodium sulfate impurities? It does not matter in cleaning. Just keep it with sodium ethyl sulfate and calculate the double quantity. Get rid of the ethanol before distilling the nitroethane. Put the sodium chloride salt in the water. Separate the nitroethane and dry it with silica gel or any. Dryer and re-distillation will come to 116 degrees
You can extract the water phase as diethyl ether
By doing this you will save more solvent

wael ganoThis is necessary to get rid of the ethanol, use a drying agent to get rid of the water droplets, and re-distill the nitroethane. A transparent, colorless liquid with an evaporation point of 116 will emerge.

 

[wael gano]

I used this method for making sodium ethyl Sulfate.
But after purify by ethanol my yield is very low quantity like 60g approx lots of sodium ethyl Sulfate not dissolved in ethanol. So I have throw undissolved Sodium ethyl Sulfate. I am very dispute how can I get maximum quantity of Sodium ethyl Sulfate??

140g Ethanol (Anhydrous)
300g Sulfuric Acid (98%)
2000ml Distilled water
"≈" 260g Calcium Carbonate
"≈" 350g concentrated Sodium Carbonate solution (40g/100ml)
410ml Ethanol (Anhydrous) for purification



Part 1: Ethyl Hydrogen Sulfate
CH3CH2OH + H2SO4 = C2H5OSO3 + H20

Ethanol and sulfuric acid is put in freezer to cool down to 0 °C. water is put in fridge.
Ice water bath is prepared then Ethanol was added to a round bottom flask with a pressure equalizing drip funnel.
The Sulfuric acid is added SLOWLY drop by drop with strong stirring in the ice bath. The addition should take minimum 35 minutes from first to last drop.
After the addition is completed the reaction temperature should not be higher then 20 °C.
Let the solution stir vigorously in the ice bath for 60 minutes.
After 60 minutes the solution has turned yellow, the ice bath is removed and the reaction mixture is
Placed in a two necked flask and put in a heating bath that is heated to 50°C.
Heat reaction mixture to 50°C and keep it in water bath for 60 minutes then cool off to room temperature.
Put 2000ml cold water to 5L beaker then slowly add the cooled reaction mixture.


Part 2: Ethyl Hydrogen Sulfate into - Calcium Ethyl Hydrogen Sulfate
2C2H5OSO3H+CACO3 = (C2H50S03)2CA + H2O + CO2

Add calcium carbonate (≈260g) slowly with strong stirring to PH 7
The beaker is then heated to 60 °C in a water bath, also heat some rinse water 200ml.
Filter off the precipitate (Calcium sulfate) and rinse beaker and wash with the heated water.
Keep the filtered mixture.

Part 3: Calcium Ethyl Sulfate into - Sodium Ethyl Hydrogen Sulfate
(C2H50S03)2CA + NA2CO3 = 2C2H5OSO3NA + CaCO3

To filtered mixture add concentrated sodium carbonate solution (≈350g)
Calcium Carbonate will precipitate out of solution
Keep adding Sodium carbonate to it turns alkaline (PH 12-14)
Vacuum filter out the Calcium carbonate. Wash filtrate well with a little cold water
Boil solution until it becomes cloudy then filter (Precipitate this is Calcium Carbonate)
Continue to evaporate the filtrate till dry.
To dry mixture add 400ml Anhydrous ethanol and warm on water bath to most of the solids dissolves
Filter through a heated vacuum funnel, rinse Beaker with 10 ml Anhydrous ethanol.
When filtrate comes down to room temperature filter out the crystals,
Return filtrate to freezer to form second batch of crystals- then filter. Add crystals from batch one.

Manisj@1290This is an effort and a small amount of experience. You can modify some things

 

[wael gano]

I used this method for making sodium ethyl Sulfate.
But after purify by ethanol my yield is very low quantity like 60g approx lots of sodium ethyl Sulfate not dissolved in ethanol. So I have throw undissolved Sodium ethyl Sulfate. I am very dispute how can I get maximum quantity of Sodium ethyl Sulfate??

140g Ethanol (Anhydrous)
300g Sulfuric Acid (98%)
2000ml Distilled water
"≈" 260g Calcium Carbonate
"≈" 350g concentrated Sodium Carbonate solution (40g/100ml)
410ml Ethanol (Anhydrous) for purification



Part 1: Ethyl Hydrogen Sulfate
CH3CH2OH + H2SO4 = C2H5OSO3 + H20

Ethanol and sulfuric acid is put in freezer to cool down to 0 °C. water is put in fridge.
Ice water bath is prepared then Ethanol was added to a round bottom flask with a pressure equalizing drip funnel.
The Sulfuric acid is added SLOWLY drop by drop with strong stirring in the ice bath. The addition should take minimum 35 minutes from first to last drop.
After the addition is completed the reaction temperature should not be higher then 20 °C.
Let the solution stir vigorously in the ice bath for 60 minutes.
After 60 minutes the solution has turned yellow, the ice bath is removed and the reaction mixture is
Placed in a two necked flask and put in a heating bath that is heated to 50°C.
Heat reaction mixture to 50°C and keep it in water bath for 60 minutes then cool off to room temperature.
Put 2000ml cold water to 5L beaker then slowly add the cooled reaction mixture.


Part 2: Ethyl Hydrogen Sulfate into - Calcium Ethyl Hydrogen Sulfate
2C2H5OSO3H+CACO3 = (C2H50S03)2CA + H2O + CO2

Add calcium carbonate (≈260g) slowly with strong stirring to PH 7
The beaker is then heated to 60 °C in a water bath, also heat some rinse water 200ml.
Filter off the precipitate (Calcium sulfate) and rinse beaker and wash with the heated water.
Keep the filtered mixture.

Part 3: Calcium Ethyl Sulfate into - Sodium Ethyl Hydrogen Sulfate
(C2H50S03)2CA + NA2CO3 = 2C2H5OSO3NA + CaCO3

To filtered mixture add concentrated sodium carbonate solution (≈350g)
Calcium Carbonate will precipitate out of solution
Keep adding Sodium carbonate to it turns alkaline (PH 12-14)
Vacuum filter out the Calcium carbonate. Wash filtrate well with a little cold water
Boil solution until it becomes cloudy then filter (Precipitate this is Calcium Carbonate)
Continue to evaporate the filtrate till dry.
To dry mixture add 400ml Anhydrous ethanol and warm on water bath to most of the solids dissolves
Filter through a heated vacuum funnel, rinse Beaker with 10 ml Anhydrous ethanol.
When filtrate comes down to room temperature filter out the crystals,
Return filtrate to freezer to form second batch of crystals- then filter. Add crystals from batch one.

Manisj@1290Add 215ml absolute ethanol
Add 108 ml (2 moles) of sulfuric acid slowly after the addition is complete. Heat to 80 degrees for 2.5 hours.
Turn off the heat and cool the mixture
Place it in a plate, then take 200 grams of sodium carbonate and add it until it equals the pH 8
After that, wait hours for the sodium carbonate to react well. Without adding water, there is a little ethanol. Allow it to evaporate into the air
The yield is 290 grams
Mixed moles of sodium ethyl sulfate
Mole of sodium sulfate
I used 2 moles of sulfuric acid, producing one mole of ethyl sulfate
One mole of sulfuric acid remains unreacted
Sodium sulfate, it doesn't matter, don't separate anything. Put everything and add 1 mole of sodium nitrite 103 grams with 50 ml of water and start distillation.

 

[wael gano]

I Successfully synthesized nitroethane but not pure can I make p2np with impure nitroethane.

Manisj@1290Yes, you can, but you will get a very dirty p2np. The reaction becomes black and the crystals are dirty. They need to be washed with isopropyl alcohol. It is better to clean the nitroethane before working.

 

[Manisj@1290]

Yes, you can, but you will get a very dirty p2np. The reaction becomes black and the crystals are dirty. They need to be washed with isopropyl alcohol. It is better to clean the nitroethane before working.

wael ganoI try to separate pure Nitroethane.
First I put diethy ether in nitroethane and saw 2 layer in my separating funnel upper layer put in flask and dry with calcium chloride after that I distilled 45 c when bubble stop than change the receiving flask and set the temperature 116 c but all liquid distilled at 70-75c .

 

[wael gano]

I try to separate pure Nitroethane.
First I put diethy ether in nitroethane and saw 2 layer in my separating funnel upper layer put in flask and dry with calcium chloride after that I distilled 45 c when bubble stop than change the receiving flask and set the temperature 116 c but all liquid distilled at 70-75c .

Manisj@1290Hold the temperature for a while at 50/60 degrees to get rid of any impurities or solvent