Glycerol + NaHSO4 ? Products

[jacknife360]

What are the products when glycerol (propan-1,2,3-triol) CH2(OH)CH(OH)CH2(OH) and sodium bisulphate (hydrogensulphate) NaHSO4 are mixed and gently heated.

 

Ta for any help

[budullewraagh]

how hot does it get? depending on temp i would imagine you could get an esterfication

[jacknife360]

what would the products of it be, an ester? I thought a carbonyl or anhydride was needed?

[budullewraagh]

the bisulfate could, potentially, esterfy under the right conditions

[jgerlica]

I believe you may get a bit of acroleine

[budullewraagh]

you think the bisulfate will dehydrate it that much?

[Hexaditon]

Here is a good look at the mechanism of esterifications:

http://wyk.edu.hk/~paulsiu/Chemistry/ester.htm

 

No, esterifications will not happen. There's not inorganic acid in that mix that'll cause it.

 

The question on how hot it would get is very relevant. If it is hot enough to decompose the glycerin then this is a completely different game.

[budullewraagh]

sodium bisulfate, when aqueous, is to an extent acidic. yes, i understand the dissociation constant is quite high and the acidity is countered by the natrium cation

 

as well, the glycerin would oxidize before it were to decompose

[Hexaditon]

And once again I reiterate - there's not an inorganic acid in that mix that'll cause the esterification. The acidic conditions of a sodium bisulfate solution is not an inorganic acid with the abilities to cause esterification.

 

Firstly, how is the last statement relevant? It's only giving me another point to pick at.... The oxidization of the glycerin molecule IS the decomposition reaction.

 

It will not oxidize before it decomposes because it is decomposing by oxidation.

Anything else?

[budullewraagh]

"with the abilities"

actually, all you need is one hydronium cation and you have catalyzed esterfication. the bisulfate does dissociate to a degree, yielding hydronium cations

 

"The oxidization of the glycerin molecule IS the decomposition reaction."

it actually isn't buddy. oxidation is just that, oxidation. decomposition can be observed by the reaction of nitroglycerin to yield nitrogen, carbon dioxide, water and oxygen. it has one reactant and products consisting only of atoms formerly found in the reactant molecule.

[Hexaditon]

1) Umm how about you look at the mechanics of esterification again and stop trying to bs your way out of error. No that is not how esterification works it does not take ONE hydrogen ion to cause the reaction otherwise esterification would proceed without any acid. But you should know that H2O breaks down into H+ and OH- on it's own since you're going to harvard and all. I don't see how you could overlook that. Anyhow... no no no you don't know what esterification is so please no again.

 

2) the decomposition of NG is another example of an OXIDIZATION reaction. Oxidization of glycerin, nitroglycerin, ****ing paper is a decomposing reaction. Just like burning a piece a candle in the presence of oxygen is causing a decomposition reaction and it is that oxidization that produces heat - released energy.

[budullewraagh]

i understand fischer esterfication. reactions happen over time. if there is just one hydronium cation, esterfication will occur. this reaction is reversible and will be at equilibrium that strongly favors the reverse reaction. nonetheless, there will be a certain amount of ester present at all times.

 

"the decomposition of NG is another example of an OXIDIZATION reaction."

try again buddy

[math]4C_3H_5N_3O_9 --> 6N_2+12CO_2+10H_2O+O_2[/math]

[Hexaditon]

http://www.dictionary.com : deflagration

The detonation of NG is not an oxidation reaction you would be correct. The deflagration of such is an oxidization reaction. Which would be burning NG.

 

NG does not detonate upon burning. It's not a primary - does not go through DDT (deflagration to detonation transition) and it's decompisition by excessive heating is through oxidization. Just as glycerin itself... just as paper.... just as burning a log.

 

Sure it's science... but it's not that complicated.

[budullewraagh]

i can cite my source, which happens to be napoleon's buttons. you should read it. it happens to be quite an interesting book

[Hexaditon]

Sure cite it so I can break it down for you in explanation. I'm sure it's a fabulous book - it'll be more useful if you could comprehend it.

 

There is a clear difference between detonation and deflagration.

Did your book explain that to you?

 

The reaction you provided is a detonation reaction.

The burning of NG is a deflagration reaction with is a decomposition reaction/oxidizing reaction.

 

Talking about NG detonating is irrelevant to this topic about the oxidizing of glycerin

[budullewraagh]

"it'll be more useful if you could comprehend it."

this is coming from the pompous jackass who has yet to read it. i directly quoted the book.

 

i was merely explaining to you how glycerin oxidizes and does not decompose. apparently some are too stupid to learn. does the fact that admitting i am correct seem less appealing because it proves you are wrong? does it negate the validity of truth?

[Hexaditon]

You never quoted anything about 'glycerin oxidizes, but doesn't decompse'. If you ever found that in the book - I'd recommend burning the book. However, I really doubt that's the reality of the book, but rather your lack of interpretive abilities.

 

You quoted an equation of nitroglycerin detonating. Which is not deflagration. Which is not anything to do with temperature. Which is not anything to do with what we're talking about nor what you know.

 

Quote the book please, so I can put it in context for you.

[jacknife360]

acroleine -

as in 1-oxo prop-2-ene

[budullewraagh]

"Quote the book please, so I can put it in context for you."

i did

[Sayonara]

Don't make me come in here.