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All 9 posts Subject: Mace oil - high bp fraction Please login to post Down

pyroflatus
(Stranger)
10-28-04 08:16
No 538286
      Mace oil - high bp fraction

Over the last three days 500g of mace oil was fractionally distilled at 1.05mmHg through a 300mm column stuffed with stainless steel wool.

The last fraction is a tad over 90mL, and was collected from 99-110 degrees. The temp rose slowly from 99 to 110 over about 3 hours.

A BP test showed the oil boiling at 246 C.
A few drops shaken with KMnO4 solution turned the solution brown, and the smell changed from a gentle but pungent odour to the smell of preserved orange peel.

I am expecting this fraction to contain eugenol and myristicin, but the boiling point confuses me.

Given the ~20 degree temperature separation of eugenol and myristicin at 760mmHg, is it likely that fractionating at standard pressure will allow separation of these two compounds?

Also, has anyone successfully distilled myristicin at standard pressure?

hypo
(Balanced Ego)
10-30-04 14:07
No 538735
      eugenol vs. myristicin

eugenol is a phenol, so why not try extracting it with 5% NaOH?

> A few drops shaken with KMnO4 solution turned the solution brown, and the smell
> changed from a gentle but pungent odour to the smell of preserved orange peel.

what is that supposed to prove? transformation into the benzaldehyde?
but yeah, the smell of myristicin is very gentle. i wouldn't call it pungent, but
this is highly subjective.

> Given the ~20 degree temperature separation of eugenol and myristicin at 760mmHg

afaik myristicin boils at 277°C whereas eugenol boils at 360°C. that's more like 100°C!

HÎ¨=EÎ¨

indole_amine
(Hive Bee)
10-30-04 15:37
No 538742
User Picture       qualitative analysis

Precipitation of MnO2 is a detection method for the presence of carbon-carbon double bonds, nothing else. Every propenylbenzene or allylbenzene gives this color with KMnO4.

_{indole_amine}

hypo
(Balanced Ego)
11-01-04 14:11
No 539076
      oh...

could it be that the original poster is talking about elemicin and mysristicin?
i think so...

in which case it is probably adviceable to fractionate it at least twice or
thrice at medium vacuum (say 20mmHg).

HÎ¨=EÎ¨

pyroflatus
(Stranger)
11-02-04 00:05
No 539133
      >what is that supposed to prove?

>what is that supposed to prove? transformation into the benzaldehyde?

It's supposed to prove there are oxidisable double bonds, nothing more. There happened to be some permanganate solution prepared and handy, is all.

>afaik myristicin boils at 277°C whereas eugenol boils at 360°C. that's more like 100°C!

I have a number of references that say eugenol boils at 253-257°C, including this msds (http://www.pulpdent.com/perio/eugmsds.html) and this (http://physchem.ox.ac.uk/MSDS/EU/eugenol.html) and so on.

hypo
(Balanced Ego)
11-02-04 08:34
No 539191
      bold conclusion

> It's supposed to prove there are oxidisable double bonds, nothing more.

that's a bold conclusion.

> I have a number of references that say eugenol boils at 253-257°C

great, then it's even more than 100°C difference!

HÎ¨=EÎ¨

pyroflatus
(Newbee)
11-02-04 12:48
No 539210
      pardon?

> I have a number of references that say eugenol boils at 253-257°C

great, then it's even more than 100°C difference!

Sorry, what? If myristicin's BP is 275° and eugenol's is 253° how does that equate to over 100°C difference, except in binary? {please don't say 'trinary'}

hypo
(Balanced Ego)
11-02-04 13:06
No 539212
      heh...

sorry... i thought you gave the bp of myristicin... crazy

that's weird, my merck index definitely says 360°... i will check what beilstein says...
anyway, you should be able to extract it with 5%NaOH.
i would be more afraid of the elemicin.

HÎ¨=EÎ¨

hypo
(Balanced Ego)
11-02-04 14:27
No 539215
      you're right of course...

beilstein has values from 247 to 259° and even the merck index says 255° -
i was looking under the benzoyl derivate... tongue

HÎ¨=EÎ¨

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	All 9 posts		Subject: Mace oil - high bp fraction		Please login to post		Down


		pyroflatus (Stranger) 10-28-04 08:16 No 538286				Mace oil - high bp fraction
						Over the last three days 500g of mace oil was fractionally distilled at 1.05mmHg through a 300mm column stuffed with stainless steel wool. The last fraction is a tad over 90mL, and was collected from 99-110 degrees. The temp rose slowly from 99 to 110 over about 3 hours. A BP test showed the oil boiling at 246 C. A few drops shaken with KMnO4 solution turned the solution brown, and the smell changed from a gentle but pungent odour to the smell of preserved orange peel. I am expecting this fraction to contain eugenol and myristicin, but the boiling point confuses me. Given the ~20 degree temperature separation of eugenol and myristicin at 760mmHg, is it likely that fractionating at standard pressure will allow separation of these two compounds? Also, has anyone successfully distilled myristicin at standard pressure?



		hypo (Balanced Ego) 10-30-04 14:07 No 538735				eugenol vs. myristicin
						eugenol is a phenol, so why not try extracting it with 5% NaOH? > A few drops shaken with KMnO4 solution turned the solution brown, and the smell > changed from a gentle but pungent odour to the smell of preserved orange peel. what is that supposed to prove? transformation into the benzaldehyde? but yeah, the smell of myristicin is very gentle. i wouldn't call it pungent, but this is highly subjective. > Given the ~20 degree temperature separation of eugenol and myristicin at 760mmHg afaik myristicin boils at 277°C whereas eugenol boils at 360°C. that's more like 100°C! HÎ¨=EÎ¨



		indole_amine (Hive Bee) 10-30-04 15:37 No 538742				qualitative analysis
						Precipitation of MnO2 is a detection method for the presence of carbon-carbon double bonds, nothing else. Every propenylbenzene or allylbenzene gives this color with KMnO4. _{indole_amine}



		hypo (Balanced Ego) 11-01-04 14:11 No 539076				oh...
						could it be that the original poster is talking about elemicin and mysristicin? i think so... in which case it is probably adviceable to fractionate it at least twice or thrice at medium vacuum (say 20mmHg). HÎ¨=EÎ¨



		pyroflatus (Stranger) 11-02-04 00:05 No 539133				>what is that supposed to prove?
						>what is that supposed to prove? transformation into the benzaldehyde? It's supposed to prove there are oxidisable double bonds, nothing more. There happened to be some permanganate solution prepared and handy, is all. >afaik myristicin boils at 277°C whereas eugenol boils at 360°C. that's more like 100°C! I have a number of references that say eugenol boils at 253-257°C, including this msds (http://www.pulpdent.com/perio/eugmsds.html) and this (http://physchem.ox.ac.uk/MSDS/EU/eugenol.html) and so on.



		hypo (Balanced Ego) 11-02-04 08:34 No 539191				bold conclusion
						> It's supposed to prove there are oxidisable double bonds, nothing more. that's a bold conclusion. > I have a number of references that say eugenol boils at 253-257°C great, then it's even more than 100°C difference! HÎ¨=EÎ¨



		pyroflatus (Newbee) 11-02-04 12:48 No 539210				pardon?
						> I have a number of references that say eugenol boils at 253-257°C great, then it's even more than 100°C difference! Sorry, what? If myristicin's BP is 275° and eugenol's is 253° how does that equate to over 100°C difference, except in binary? {please don't say 'trinary'}



		hypo (Balanced Ego) 11-02-04 13:06 No 539212				heh...
						sorry... i thought you gave the bp of myristicin... that's weird, my merck index definitely says 360°... i will check what beilstein says... anyway, you should be able to extract it with 5%NaOH. i would be more afraid of the elemicin. HÎ¨=EÎ¨



		hypo (Balanced Ego) 11-02-04 14:27 No 539215				you're right of course...
						beilstein has values from 247 to 259° and even the merck index says 255° - i was looking under the benzoyl derivate... HÎ¨=EÎ¨

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