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ssdd
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Esters and their Synth
I am trying to make up some Isoamyl Acetate (Banana Oil) along with some other esters. The issue for this synth is that I can seem to find Isoamyl
Alcohol anywhere for a decent price. I checked ebay and came up with nothing, and most suppliers have some crazy prices!
Here is the synth in the manner I would like to try it.
Add 15 ml of Isoamyl Alcohol to a 250ml flask. Then pour in 20 ml of Glacial Acetic acid. Add 4 ml of conc. Sulfuric Acid. Place several boiling chips
into this. Slowly biol this flask on a hot plate for about an hour. (A reflux condenser is recommended but I think it can be done without one, at
least I hope since I don't have one.) 
My question would be is there another way to make isoamyl acetate or where can I find Isoamyl Alcohol for cheap?
Thanks for any info...
**Changed name of topic to make it more general - ssdd
[Edited on 2-6-2007 by ssdd]
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bereal511
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You'd probably need to at least keep the alcohol from escaping the reaction, so just having a condenser attached to the flask would work.
As an adolescent I aspired to lasting fame, I craved factual certainty, and I thirsted for a meaningful vision of human life -- so I became a
scientist. This is like becoming an archbishop so you can meet girls.
-- Matt Cartmill
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leu
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Better directions can be found in the attached file, if this compound is prepared in a room with open windows or outdoors expect some interest from
the genus apis  Isoamyl alcohol is a major constituent of fusel and
potato-spirit oil, and can be made from butadiene as in US 3020314, and from methylbutenes in JACS 82 1505 (1960) The fractionation of fusel oil and other processes are discussed in pp 107-114
Industrial Chemicals 2d Ed (1957) 
[Edited on 30-5-2007 by leu]
Attachment: bananaoil.zip (40kB)
This file has been downloaded 883 times
Chemistry is our Covalent Bond
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ssdd
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Ahhh thank you this gives a better explanation than where I was looking.
Interesting file format by the way.
I was given a link to some isoamyl yesterday so once I have it I'll give this a run.
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Tsjerk
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molar sieves
I recently got some isoamyl alcohol, but I don't like wasting it because it's not one of the easiest chemicals to get as a amateur. I'm planning to
make some isoamyl acetate with it and I was thinking how to get the equilirium more towards the ester side.
Which way would give the highest yield? Using a large excess of acetic acid, or refluxing it over molar sieves and taking the water out?
I was planning to reflux it over a soxhlett-extractor, and placing the sieves in the soxhlett.
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ssdd
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So I went rummaging through my schools flammable cabinet and found a small jar of amyl alcohol, I'm not sure if this is just a isomer of isoamyl so I
gave it a try.
The result was amyl acetate with a distinct banana scent. I also made wintergreen oil (Ethyl salicylate) and Ethyl Butyrate (pineapple).
My question is is that amyl acetate the same as isoamyl acetate? They have the same smell and oily properties from what I could tell but if anyone has
any further info it would help.
Note: Don't inhale to much banana oil, it'll mess you up. 
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Pyridinium
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| Quote: | Originally posted by ssdd
My question is is that amyl acetate the same as isoamyl acetate? They have the same smell and oily properties from what I could tell but if anyone has
any further info it would help.
Note: Don't inhale to much banana oil, it'll mess you up.
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"amyl acetate" and "isoamyl acetate" are used interchangeably many times. However, the acetic ester of n-amyl alcohol is not the same molecule as the
acetic ester of iso-amyl alcohol.
You can get the data for n-amyl acetate at http://en.wikipedia.org/wiki/Amyl_acetate
You're right, too much banana oil will definitely mess you up.
In very high concentrations it is indeed toxic.
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ssdd
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Hmmm, yea there seems to be a difference. It seems that even the odors produced from the two seem to be mildly different from one another. Amyl
Acetate is just banana, where isoamyl is described as being "fruity" in its smell often being compared to banana. Now something that would be neat to
try is to see if amyl acetate still works as a bee pheromone or if this mild difference makes it ineffective.
--------------------
So I'm sitting here looking at this flask with the oil in it. The oil seems to be floating on the remnants of the alcohol and neutralizing solution. I
am wondering what the best method to extract this would be with the smallest amount of waste and contamination?
[Edited on 31-5-2007 by ssdd]
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Comedy
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| Quote: | Originally posted by Tsjerk
I recently got some isoamyl alcohol, but I don't like wasting it because it's not one of the easiest chemicals to get as a amateur. I'm planning to
make some isoamyl acetate with it and I was thinking how to get the equilirium more towards the ester side.
Which way would give the highest yield? Using a large excess of acetic acid, or refluxing it over molar sieves and taking the water out?
I was planning to reflux it over a soxhlett-extractor, and placing the sieves in the soxhlett. |
I think the second option would give the highest yield
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ssdd
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Any ideas anyone on how to remove the floating banana oil from the neutralizing solution?
There is about 20ml of the oil total on about 160mls of solution. Would a separatory funnel work for this? Or is there a better way with less waste?
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UnintentionalChaos
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I'd use a sep funnel to get the majority of it, then do a liquid-liquid extraction on what is left (assuming you have an appropriate solvent) to get
the maximum yield.
Department of Redundancy Department - Now with paperwork!
'In organic synthesis, we call decomposition products "crap", however this is not a IUPAC approved nomenclature.' -Nicodem
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Chemophiliac
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I am curently taking an instrumentation class at school that includes a bit of basic organic chemistry experiments and theory. We just synthesized
some flavors (I made Ethyl Butyrate- Pineapple) and did analysis on them to prove exactly what our product was. We performed GC (In Dichloromethane
solvent), FTIR, Regular IR, and UV-Vis Spec.
Anyway, the synthesis of ester flavors is simple.
Simply combine the reactants and add just a few drops (3 or 4) of concentrated sulfuric acid as a catalyst. Reflux the reaction in a steam bath, the
assembly is simple- just attatch a condenser on top of a reaction vessel, grease the joints and add some boiling chips to prevent bumping. Let the
reaction reflux for a day.
THEN, use a sep funnel to do a liquid-liquid extraction. Esters are soluable in Dichloromethane so dissolve them in this, which will separate to the
bottom. Add a saturated brine solution to help draw out some water from the organic laer. Separate the organic layer and the add some anhydrous sodium
sulfate, which will clump on the bottom. Continue adding the sodium sulfate until it stops clumping and is evenly distributed in the liquid when
swirled. Filter the solution through a plug of glass wool. hen, boil off the dichloromethane over a steam bath. add 2 or 3 boiling chips to the
product that was gathered.
you see, it's fairly simple, just reflux and separate. Now, here are the reactants for some interesting flavor esters including, but not restricted
to isoamyl acetate. All of these use the same procedure I outlined above
Banana (isoamyl acetate)- isoamyl alcohol and acetic acid
Apricot (isoamyl butyrate)- isoamyl alcohol and butyric acid
Apple (methyl butyrate)- methyl alcohol and butyric acid
Grape (methyl anthranilate)- methyl alcohol and 2-aminobenzoic acid (anthranilic acid)
Honey (ethyl phenylacetate)- ethyl alcohol and phenylacetic acid
'Juicy Fruit' (isopentyl acetate)- isopentyl alcohol and acetic acid
Orange (octyl acetate)- n-octyl alcohol and acetic acid
Peach (benzyl acetate)- benzyl alcohol and acetic acid
Pear (n-propyl acetate)- n-propyl alcohol and acetic acid
Pineapple (ethyl butyrate)- ethyl alcohol and butyric acid
Pineapple (isoamyl salicylate)- isoamyl alcohol and salicylic acid
Raspberry (isobutyl formate)- isobutyl alcohol and formic acid
Rum (isobutyl propionate)- isobutyl alcohol and propionic acid
Walnut (ethyl valerate)- ethyl alcohol and valeric acid
Wintergreen (methyl salicylate)- methyl alcohol and salicylic acid
Now, try them out!
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12AX7
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Is there one for raspberry or cherry?
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bereal511
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3-(4-hydroxyphenyl)-2-butanone appears to have the smell of raspberries based on this database: http://mc2.cchem.berkeley.edu/Smells/
Not sure about cherry, there's a lot of different cited compounds but I'm not definite on which one is "cherry" as in cherry coke or the lot per say.
It does list benzaldehyde as "cherry flavor".
[Edited on 1-6-2007 by bereal511]
As an adolescent I aspired to lasting fame, I craved factual certainty, and I thirsted for a meaningful vision of human life -- so I became a
scientist. This is like becoming an archbishop so you can meet girls.
-- Matt Cartmill
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ssdd
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The wikipedia page on esters has some interesting esters.
http://en.wikipedia.org/wiki/Esters
I ran two more of these yesterday with variable success. I made ethyl benzoate, which had a very pleasant odor to it. According to that link it is the
smell of the feijoa fruit.
I also made ethyl lactate. If any odors were produced by this I could not pick them up with my nose. It is supost to smell like butter or coconut. Is
it perhaps that the smell is to faint or that I didn't reflux it for long enough?
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Nicodem
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| Quote: | Originally posted by ssdd
Any ideas anyone on how to remove the floating banana oil from the neutralizing solution?
There is about 20ml of the oil total on about 160mls of solution. Would a separatory funnel work for this? Or is there a better way with less waste?
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For the workup check for similar esterifications in Vogel's or other books on practical chemistry (no need to reinvent the wheel…). Mind that you
will have to fractionate your product trough a distillation column to separate the ester from amyl alcohol (while acetic acid removes already with a
single NaHCO3 wash, the alcohol sticks to the organic extract).
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ssdd
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So I decided to give some of these oils a taste test today.
I'm not sure how good this is for my health but o well. I isolated the banana oil, wintergreen, pineapple, and ethyl benzoate. Now I tried these and
most had a fairly tart taste with really no flavor like what they smalled like. Are there any ideas as to why this came out this way?
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Eclectic
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Taste is only satly, sweet, bitter, sour, umami.
Taste
Everything else is smell.
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Fleaker
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If they were really sour, you didn't remove enough of the acid (the sulfuric used to keep it dry).
Neither flask nor beaker.
"Kid, you don't even know just what you don't know. "
--The Dark Lord Sauron
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ssdd
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Fleaker, I tried adding more Bicarb to it and it did not show any signs that it was still acidic. I'll give an update later after I test it with
litmus.
Upon tasting after it had the bicarb added it was still pretty sour and had a strong basic taste to it. Perhaps it is the area of my mouth that I am
touching the wood splint to?
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not_important
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better way to taste is to add a small drop to some water, close the container and let it sit for awhile, then taste a little of the water. Straight
ester may be overwhelming, enough should dissolve in the water to be released in the mouth to give the aroma - as already said, taste is limited to 5
or 6 basic tastes, not too related to aromas; there is interaction in that acidic and sweet tastes go with fruity aromas and may may the aroma "more
real".
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Eclectic
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You could make up some unflavored "Gatoraide" with sugar, citric acid, and a pinch of salt, and add a drop of the various esters to determine the
different taste/odor properties.
These products are essentially the same thing, although a bit heavier on the salts:
Calf Electrolyte Replenisher
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ssdd
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Now that is interesting... Is that really all there is to gatoraide?
If that is all it is they sure over price it.
ssdd
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tongqiancao
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Maybe a silly question
you really taste it ?Even books tell us some substances are just that we meet everyday,I don't dare to taste them in lab.
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ssdd
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| Quote: |
you really taste it ?Even books tell us some substances are just that we meet everyday,I don't dare to taste them in lab. |
I can see where your coming from on this, most of these substances have a fairly low toxicity on their own. (Except the amyl acetate which is fairly
toxic, but it's the gases that scare me more.) Also, they are being tested in very small quantities, for the original test I simply dipped the tip of
a tooth pick into them, and for some of the stuff just mentioned we are talking about a single drop. So as far as I can read this should be fairly
safe. (Someone PLEASE inform me if this is not so. )
Welcome to Science Madness by the way...
[Edited on 6-6-2007 by ssdd]
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