Sciencemadness Discussion Board

Products of dry distillation of sucrose

Random - 11-4-2013 at 06:38

I have been experimenting with this like 2 years ago in a small distillation vessel made from aluminium foil directed into a cooled test tube. It was a bad yield due to a bad apparatus, but I still remember the results.

I produced a yellow liquid and a small brown droplet of oily liquid floating on it. It smelled strongly of caramel. It smelled so much that just like a mL of this in the test tube could be smelled around the room where I left it. I guess the majority of this (yellow liquid) wasn't water since I covered the entire test tube in aluminium foil and it all evaporated the next 2 days, unlike water which stays there for a long time, especially if I cover it with Al foil.



So I thought to myself, what are the products? I tried to research the subject here:

http://sciencegeist.net/the-chemistry-of-caramel/
Quote:

But, when fructose and glucose start to break down into smaller, more volatile compounds, your brain can very easily detect that there are new molecules present. Some important molecules that are produced during caramelization are the furans (have a nutty aroma), diacetyl (smells like butter), maltol (toasty), and ethyl acetate (fruity).



But this is just one piece of what I found. But I do think there was at least a big part of only few compounds in my distillate.


What was it, maltol? Furans? Diacetyl? How would the product look like if we dry distilled about a kilogram of sucrose? To investigate the products, we would need a lot of this distillate.


It seems like an interesting field to research, because the chemistry of caramel is not yet fully understood.

Since I don't have any way to distill a large amount of sucrose, would anyone be up for this experiment? Maybe we could get some very useful precursors to other compounds this way. I see people dry distilling like 500g of corn for 10g of furan? Maybe this would give a better yield for example.

simba - 11-4-2013 at 09:40

How much sugar did you dry distill and how much distillate did you get? Even if this produces any useful amounts of chemicals, it would still be a pain to purify them, doesn't sound much attractive to me.

Random - 11-4-2013 at 11:18

Quote: Originally posted by simba  
How much sugar did you dry distill and how much distillate did you get? Even if this produces any useful amounts of chemicals, it would still be a pain to purify them, doesn't sound much attractive to me.


About a tablespoon of sugar for 1-2mL of distillate. Keep in mind a lot was lost because apparatus wasn't very convinient.

Aldehydes can be separated by bisulfite adducts, water soluble and insoluble stuff etc.. it is doable.

I guess it would be about 80-160mL of distillate per kilo of sugar by rough estaminate..not bad considering how cheap it is.

[Edited on 11-4-2013 by Random]

[Edited on 11-4-2013 by Random]

zed - 1-5-2013 at 13:15

Is Levulinic Acid present?

Also of note: Levulinic Acid has been hyped as being fairly non-toxic. Possibly by folks who would like to promote the use of its esters as alternative fuels for internal combustion engines.

As I recall, Levulinic Acid, used to scare the piss out of me. The bottle bore the inscription "Danger! Levulinic Acid in eye, will cause loss of the eye."

[Edited on 1-5-2013 by zed]

Random - 1-5-2013 at 13:27

Quote: Originally posted by zed  
Is Levulinic Acid present?


Possibly

More efficient way to levulinic acid is on versuchschemie.org, using HCl as catalyst on glucose

Random - 1-5-2013 at 13:29

Quote: Originally posted by zed  

As I recall, Levulinic Acid, used to scare the piss out of me. The bottle bore the inscription "Danger! Levulinic Acid in eye, will cause loss of the eye."

[Edited on 1-5-2013 by zed]


Yes, I recall it has been posted here that it's fairly dangerous, but I am sure dry distillation doesn't produce much of it alone if acid catalyst is not used in H2O. Just because we all eat caramel and I think nobody died from eating burnt sugar etc..

zed - 1-5-2013 at 13:40

Perhaps someone should attempt to update Wiki.

When I first discovered that folk were trying to market "production facilities" to produce Levulinic acid esters as "Green" fuel....I was amazed. Fuel it may be. Safety of such fuel is questionable.

http://en.wikipedia.org/wiki/Levulinic_acid

[Edited on 1-5-2013 by zed]

AndersHoveland - 1-5-2013 at 22:18

As far as I know, the pyrolysis of carbohydrates produces mainly H2O, CO2, and ethanol.

As for that caramel smell, you might read about sugar browning reactions:
http://www.sciencemadness.org/talk/viewthread.php?tid=16766

[Edited on 2-5-2013 by AndersHoveland]

Paddywhacker - 2-5-2013 at 02:34

Quote: Originally posted by zed  
Perhaps someone should attempt to update Wiki.

When I first discovered that folk were trying to market "production facilities" to produce Levulinic acid esters as "Green" fuel....I was amazed. Fuel it may be. Safety of such fuel is questionable.

http://en.wikipedia.org/wiki/Levulinic_acid

[Edited on 1-5-2013 by zed]


Yes, you wouldn't want to get it in your eye, but you wouldn't want formic, acetic, propionic or butyric acid in your eye either. Levuinic acid is not especially bad.

Paddywhacker - 17-5-2013 at 04:20

Chemicals from pyrolysis of sucrose. It seems to be a bit of a mess, from this paper, and not very high yield.

Attachment: Johnson et al., 1969, Sucrose Pyrolysis Products.pdf (310kB)
This file has been downloaded 505 times

brew - 29-5-2013 at 22:43

This may be off topic, but there is that sugar substitute called splenda, that in short, its a disacharide, with 3 or so OH groups transformed into Cl atoms attached,so in short doesnt get metabolized and simply tastes sweet but passes through the gut etc. Well it may have some merit as a chlorinating agent. If an oxygen atom from a molecule acetate anion eg, acts as a nucleophile and attacks a carbon that a Cl has been attached, then the Cl- is a good leaving group, and the disaccaride an even better one, due to its size. ITs just a thought. *Its called splenda. Worth a look, but im a newbie, and it is of topic, but what the hell.

http://en.wikipedia.org/wiki/Sucralose


[Edited on 30-5-2013 by brew]

aliced25 - 30-5-2013 at 05:24

N-Halosaccharin is a known halogenating agent.

brew - 30-5-2013 at 17:54

Thankyou aliced25. Soz about going of topic, but I gave the N-Halosaccharin a look, and found a - it dont get much easier that this type situation.


SYNTHETIC COMMUNICATIONS
Vol. 33, No. 6, pp. 935–939, 2003

Typical procedure for the preparation of N-halosaccharin: To a well stirred solut
ion of sodium saccharin (10.25 g, 50 mmol), Na2CO3 (2.65 g,
25 mmol) andKC l or KBr (3.78 g or 6.00 g, respectively—50 mmol) in
water (250mL), a solution of oxone (30.75 g, 50 mmol) in water (30 mL)
was added slowly at 0C. After stirring for 24 h at room temperature, the
solidwas filtered off, washed with cold water and dried to give the pure
N-halosaccharin.

Thankyou.


[Edited on 31-5-2013 by brew]

[Edited on 31-5-2013 by brew]