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avtr01
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[*] posted on 10-4-2004 at 02:29
artificial flavorings/esters


Hi,
Does anyone know how to make any of the artificial flavor esters that are used to make soda/juices/ice creams/ etc...
I know that amyl acetate is banana
methyl salycilate is oil of wintergreen
but strawberry, lemon, pineapple, who comes up with all of these chemicals?
thanks
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ech310n
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[*] posted on 10-4-2004 at 03:31


I remember that Allyl Caproate (2-Propenyl hexanoate) has a pineapple odour and is used for artificial pineapple flavours.

[Edited on 10-4-2004 by ech310n]
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[*] posted on 10-4-2004 at 16:16


these are scents- I'm not sure they would have the same flavor though.
apple- methyl butanoate
apricot-pentyl butanoate
banana-3-methylbutyl ethanoate
cherry-ethyl benzoate
orange-octyl ethanoate
pineapple-ethyl butanoate
red grape-ethyl heptanoate
rum- ethyl methanoate- have made it
wintergreen-methyl salicylate-have made it
kinda minty - ethyl salicylate- have made it

avtr01; Are you wanting the procedures for these too?
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[*] posted on 10-4-2004 at 16:36


That's very interesting Rogue.
Never realised how simple those flavourings are.
Are those the official flavourings admitted for foods??
Forgive me a dumb question - but in the case of the salicylates, are those the esters or ethers? I guess the former :)
What are the procedures for those? How do you avoid ethers from forming, which are presumably not the intended products?




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The_Davster
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[*] posted on 10-4-2004 at 18:24


Well here is the semi-microscale procedure from my textbook. It has the stoich done for ethyl ethanoate and methyl salicylate. Any other ester just go with the condensation reaction
R-OH + R-COOH-->H2O + R-O-CO-R and do the stoich and use the same method. No info listed on percent yield though. -I have done the 2 reactions bellow
Chemoleo-yup they are esters, but I'm not sure if they can be eaten/used in food, not sure what stops ether from forming-mabey the temp is to low?
Procedure
1. Add 5mL ethanol and 6 mL ethanoic acid to a 25X250mm testtube
2. Add 8-10 drops of concentrated sulfuric acid as the catalyst
3. set up a hot water bath in a 250mL beaker-temp should not exceed 70*C
4. clamp the testube inside the beaker so the level of reactants inside the tube is about 1cm below the water in the bath
5. Plug testube with 1-hole rubber stopper of the correct size and insert about 50cm of glass tubing into the hole-acts like a reflux collumn
6. heat at 60-70*C for about 10min
7. dump reaction mix into 30mL of cold water
8. the ethyl ethanoate will float in a thin layer on top of the water
9. repeat for 3.0g salicylic acid 10mL methanol and 20 drops sulfuric
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avtr01
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[*] posted on 11-4-2004 at 02:17


yeah, i was hoping for some of the more unique chemicals mentioned. I have been able to find procedures on how to make oil of wintergreen (methyl salycilate) and amyl acetate but the others, like apple, cherry, etc... seem harder. I also read somewhere that artificial vanilla is extracted from sawdust! ??
Thanks for the help
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[*] posted on 11-4-2004 at 05:03


Ethers are formed at temperatures of approx. 140 deg celcius. At a temp of 70 deg no, or very small quantities of ether would form.

To scale up the procedure reflux is required. I used an oil-bath at a temp of around 100 deg celcius. After running for about 45 mins the mixture was let to cool. The resulting mixture was then mixed with a saturated brine solution. The ester floats above in a seperate layer.




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avtr01
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[*] posted on 11-4-2004 at 12:19


I'm sorry but I am sort of new to the diy chemistry community. When you talk of reflux, do you mean a reflux column made out of glass? If so, can you make your own?
Thanks
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[*] posted on 11-4-2004 at 13:00


For this experiment a simple piece of glass tubing acts as the reflux collumn. However it you were to scale it up you would probally want a proper reflux collumn. A reflux collumn is like a condenser for distilling but instead of dripping the condensed vapors into a seperate vessel they are dropped back into the reaction vessel.
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[*] posted on 11-4-2004 at 14:06


Just for anyone interested, I found this link with more about the procedure(s)

http://www.ucdsb.on.ca/tiss/stretton/chem2/orglab2.htm
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[*] posted on 11-4-2004 at 14:29


A DIY reflux column is not that difficult to make. I made one myself using a 50cm long glass tube obtained from one who makes neon lights. A 40cm PVC pipe with a diameter of approx 1 inch was drilled, one hole at the bottom and another at the top - for water inlet. Two rubber bungs were bought to fit the PVC tube, which were later bored. The glass tubing was passed through the PVC tube and stoppers. This is actually a condensor, which if placed upright acts as a reflux condensor. avtr01, if you require any help just U2U me.



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[*] posted on 11-4-2004 at 20:05
vanillin


avtr01 mentioned that artificial vanilla could be made from sawdust. I believe this is essentially correct. During the digestion of wood at a pulp mill vanillin, which is the essence of vanilla, is a byproduct. My understanding is that at one time Crown-Zellerback was recovering vanillin at one of their pulp mills. The amount recovered was enough to supply the total US demand for vanilla flavoring.
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[*] posted on 11-4-2004 at 23:58


That really is amazing, from the pulp mills to our mouths. Chemistry is such a "cool" subject :cool:
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[*] posted on 12-4-2004 at 14:21


Personally, I think it's gross, but it's not as bad as one of the sources of vitamin b12.
Anyway, just a thought, not all the flavours are esters. Orange flavours usually contain acetaldehyde (as well as an ester, ethyl butanoate IIRC). Cinnamon, vanilla, aniseed and butter are not esters either.
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[*] posted on 12-4-2004 at 14:51


What is the source for b-12? A bacteria?
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[*] posted on 12-4-2004 at 16:05


Vanillin is produced from lignin; in fact, I think it is the only current pure chemical from this source. At any rate, concentrated sulfite liqour (the waste from sulfite pulping) contains p-OH, m-MeOH "alkyl"benzenes, sulphonated at the benzylic position. I put "alkyl" in quotes, since I'm not sure exactly what form this chain is allowed to take; the picture I found showed a monomeric fragment, but it is conceivable that polymeric fragments would work too. Anyhoo, the sulphonate is hydrolized with base, and the result is oxidized to give the benzaldehyde, vanillin. Yields are low, and, I believe, most vanillin is made by petrochemical processes, formylating the appropriate catechol ether.
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[*] posted on 12-4-2004 at 18:21
vanillin is vanillin


In an ideal world all vanilla would come from beans, supporting a cottage industry in some bucolic village. And all drinking water would come from mountain brooks or artesian springs. But unfortunately this is not where we have taken ourselves. And it is going to get worse unless we get our excessive procreation under control. But I agree with avtr01 that that is the beauty of chemistry - vanillin is vanillin and H2O is H2O no matter what processes they have been subjected to, or their source. I understand that now several metropolises including Los Angeles process sewer water directly to drinking water. Now that one does make me stop and wonder!
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[*] posted on 12-4-2004 at 19:52
pulp mill byproducts


OT but I just had to say that when I worked at a mill (Kraft and sulfite) tall oil and turpentine were byproducts, although as Geo says they are not pure compounds.

The turpentine recovery unit really fascinated me as it took the liquid stream of condensed digester blowdown gas containing water and tupentine. This liquid went to a decanter that automatically, with no moving parts, drew off the tupentine from the water based on immisicibility and differences in density.
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[*] posted on 12-4-2004 at 23:40


its unfathomable to me, at least how those industrial processes work. Think about it, even ammonia, by the baush process has a yield of about 13%, but so many products (N2 and H2) are being reacted that the ammonia plants still produce millions of tons of the stuff per year. Think about how hard it is to make it homemade!!
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[*] posted on 13-4-2004 at 02:19


I know we don't live in an ideal world. I used to live in London, where the joke was that the water was the best in the world; it had been filtered by 6 sets of human kidneys before it got to us.
Vanillin is vanillin, no matter if it is from oil or the orchid. On the other hand, the flavour from real vanilla is different because there are other products present. Artificial vanilla is a whole lot cheaper than the real thing but, in my opinion, it simply doesn't taste as good.
I also have the vague feeling that keeping the vanilla growers in a job is better than not doing (hey, call me a communist).
Anyway, with my analytical chemist's hat on I could easilly check whther a vanillin sample was agricultural or petrochemical in origin.
BTW, one of the sources previously exploited for vitamin b12 was sewerage sludge.
a 13% yeild isn't great, but it doesn't matter. They recycle the other 87% and react it again.
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[*] posted on 13-4-2004 at 02:59


EWWwwwww... Sewage sludge for Vit B12?! Dont tell me it has something to do with the crap (literally)..... :o



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[*] posted on 13-4-2004 at 15:25
Crazy Ester Idea?


I was thinking of trying to make an ester like methyl salicylate, but instead of using methanol in the reaction I would use picric acid so I would get the ester picryl salicylate. I have found no info on this ester so I have a few questions before trying this:
1. Will the nitro groups on the picric acid molecule act as an inhibitor so the esterification/condensation reaction would not occur?
2. Is this a sane idea or would the product be incredibly unstable, explosive, or excedingly toxic?
3. What solvent should I use, I was thinking water but the low solubilitues of salicylic and picric seem to make it look like a bad idea because I would need a lot of water and even more sulfuric acid catalyst to absorb all the water molecules, plus the ones that form? ....hmm..... mabey just sulfuric acid for the solvent?
4. Is the procedure that I posted earlier aplicable for this synthesis, or would some part of it need to be modified for this particular reaction.
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[*] posted on 15-4-2004 at 13:53


I think that picric acid would form a charge transfer complex with salicylic acid. Given time, and a strong acid catalyst, you might get an ester. You certainly don't want to use water as the solvent, alcohols or esters won't do either. Acetone would probably degrade and/ or react with the salicylic acid. I think you are left with hydrocarbons, halocarbons or ether as the solvent. (and even ether might be pushing it.)


EWWwwwww... Sewage sludge for Vit B12?! Dont tell me it has something to do with the crap (literally).....

OK, I won't tell you, if you happen to find out, don't blame me.;)
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[*] posted on 15-4-2004 at 14:10


Well I think I will try with chloroform as the solvent, unless anyone can see a problem with it?-damn I'm gonna have to do this outside then, I hate working outside, I am in clear viewing range of the neighbors:mad:, guess I'll have to do this when they arent around, don't know when that might be. Will post results when I get this reaction done.

Never eating vitamin supplements again:P. kidding But really, B12 is B12 no matter where it comes from, as long as it is purified well I could not care less.

[Edited on 15-4-2004 by rogue chemist]
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[*] posted on 16-4-2004 at 02:44


So it is from crap?? Do expand on that :D



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