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Maja
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Eugenol
Maybe someone knows some cheap source for Clove oil or Eugenol ? I have found a source for cheap, pure eugenol, but shipping costs a lot. 1l of pure
Eugenol costs 50$ and shipping - 40$. This is to europe. That's too much. Some people from europe willing to share a source or trade ? ;] Thanks.
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Sauron
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I used to buy eugenol at the corner pharmacy, it is a toothache remedy.
Is it no longer sold that way in EU?
You can of course obtain is from cloves.
Or you can synthesize it.
If you check around you will find there are companies in Europe that sell bulk herbs abd also essential oils.
Acros Organics (chemicals not herbs) sells eugenol for $25/100 g or $98/500 g and they are in Belgium.
I'm quite sure that Panreac (Spain), Merck (Germany), Fluka (Switzerland) and Carlo Erba (Italy) also sell eugenol.
[Edited on 15-10-2008 by Sauron]
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chemrox
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Pure Eugenol is packed under N2. I have some that's still in a bottle in an envelope. I'm guessing that there's a problem with oxidation? Maybe
someone here knows for sure. I would take a look at OTC Eugenol on the IR and see what else might be there. As an aside, a DEA guy told me you have
to have an importer's license to but reagents from off shore. I'm still struggling with this one and have my Sen.'s staff looking for clarification.
The DEA license has a high tag, $1100!
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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Sauron
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What I purchased at a US pharmacy was labeled Eugenol. Perhaps USP. I do not recall. But it was not oil of cloves which is surely a mixture. Merck
cites a reference from Annalen for isolation of eugenol from oil of cloves.
I used to use oil of cloves for cleaning and preserving antique Japanese swords, a traditional application for many centuries in Japan. A very
pleasant fragrance.
I don't know what your DEA contact is talking about, chemrox. I am pretty sure that a DEA import license is not required for ALL reagent imports, most
likely he is talking about scheduled controlled substances and perhaps the very limited number of substances on the List One and List Two mandating
record keeping. Is eugenol on any of those? Anyway the thread author is talking about importing into Europe not into USA if I read him correctly.
Given that it's a 3,4-catechol (4-allylguiacol) and is not exactly unknown as a starting point for various naughtier things described in PIHKAL, I
would not be amazed if eugenol is a DEA chemical of interest. But I have not taken the effort to find out because frankly I do not care.
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jarynth
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Check out this eBay seller of essential oils:
wf-medical
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Sauron
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I repeat, eugenol is not same as oil of cloves. You can if competent isolate eugenol from oil of cloves. Citation for details on how to do are to be
found in Merck Index. The paper cited in in German and available via References.
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Nicodem
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Oil of clove practically always contains more than 80% eugenol. Actually, it is quite common for it to contain up to 95% eugenol while the rest being
a couple of % of O-methyleugenol and O-acetyleugenol. I think for the average amateur this is not such a bad purity and can be considered technical
quality eugenol.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Sauron
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100 g for $25 for pure eugenol, who needs technical?
$5.59/oz. for the essential oil. I'd hold out for the pure.
[Edited on 15-10-2008 by Sauron]
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Maja
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http://cgi.ebay.com/ws/eBayISAPI.dll?ViewItem&item=17023... Pretty reasonable price ! But shipping ... Thank you jarynth for that link ! Very
helpful.
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Ephoton
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that's a ripoff I pay around $60 us for a liter of oil.
fractionation is far from requiring competence just the right equipment and patience.
e3500 console login: root
bash-2.05#
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jarynth
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The offer Maja posted is comparable to yours. And $60/L IS not a ripoff. Shipping will probably double the cost, but it'll still be very affordable
compared to European prices.
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Sauron
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I'm more than a little disappointed and chagrined that on a forum of sois-dissant chemists, no one, not one, has had anything to say about the
synthesis of eugenol.
Why is that?
Where are all the guys who always insist on making their own reagents, for the love of chemistry, even when the stuff is readily obtainable?
It is not a very complex compound. It is true that the prep does not exactly leap from the pages of the chemical literature. Org.Syn. has only
o-Eugenol which is useless. Merck only cites the isolation from clove oil. The ACS search engine is also unhelpful. Still, I haven't despaired. I
can think of several entry points, such as allylbenzene, or guiacol, or catechol.
For me it's just a five finger exercise. I have no use for eugenol.
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bfesser
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Not sure how much you need, or the purity, but I'd recommend isolation from whole cloves. The following is summarized from notes in an old lab
notebook of mine:
Crush whole cloves in mortar/pestle and steam distill until the distillate comes over clear. Extract with t-butyl methyl ether. Extract the ether
phase with 10% NaOH(aq.). Acidify the aqueous phase with dil. HCl to pH 1, then extract again with t-butyl methyl ether. To ensure good separation
and to aid in drying, shake the ether phase with saturated aqueous NaCl before drying over anhydrous CaCl<sub>2</sub>
(MgSO<sub>4</sub> is also suitable). Filter out the desiccant and evaporate the ether solvent.
20.1% yield based on an expected 15% by mass 'essential oils' content of the cloves, but the distillation was cut short due to time constraints. The
<sup>1</sup>H NMR of the eugenol was very clean--I would estimate at least 99% purity.
[Edited on 10/15/08 by bfesser]
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Sauron
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I suppose the whole matter of eugenol synthesis has been done to death by the usual suspects on Rhodium/Hive. Org.Syn. has got catechol prep from
salicaldehyde, that suggests the aspirin squeezers are on right track.
Rhodium has got propenylbenzenes from propiophenones via Friedel-Crafts acylation with propionyl chloride.
So it seems there are no new worlds to conquer at least in this neighborhood. I should have known.
Case closed.
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kalacrow
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I suppose the whole "eugenol synthesis" thing has no interest because it is not only easily obtainable and cheap, but as a starting material it isn't
particularly amazing, since the side chain is subject to polymerization if you breathe on it too hard. The routes to get TO eugenol, as well, involve
things which are more interesting THAN eugenol, generally speaking.
One thing I intend on playing with, though, is using the old method to oxidize eugenol to vanillin. Kind of a neat synth, even though it is ancient.
Are there any public refs for it? I have spent a little time looking, but so far no procedural details.. only oblique references.
This is interesting as I am guessing the reagents are cheap, and the end product I can use to make cookies  Not only that, but vanillin in pure form is (NOT extract), for some odd reason, expensive retail. A lot more than
clove oil.
FYI essentialoil.com has clove bud oil for $232US/10lbs (4.535 Liters.. 153 oz) for those folks in the US. That works out to $51/liter sans shipping.
I wonder how much it would cost to get enough clovebuds in bulk to extract that much?
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Sauron
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If I recall that old vanillin prep is from isoeugenol, and that not being a terminal alkene, is not so much of a polymerization hassle. While you can
make isoeugenol via isomerization of eugenol, it is not necessary, as it is available in essential oils in high concentrations as well.
The Flavors & Fragrances section of Ullmans, particularly the subsection on Phenolics, has a good overview on the whole family of these compounds.
[Edited on 16-10-2008 by Sauron]
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zed
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Permit to import Eugenol? It isn't listed!
It is common for government agents to lie when making oral statements.
Few, are willing to put those lies down on paper.
A probing registered letter, demanding a quote of current import regulations will put this question to rest.
I read the regulations recently, and I found no prohibition that requires a permit to import unlisted chemicals.
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Sauron
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My o my, you are a paranoiac. You think search ing Aldrich online "creates a record" and you think all federal agents are liars. More likely the guy
was simply mistaken, or that chemrox misquotes or misunderstood him.
As to Aldrich, well, what a burdensome and useless data mine that would be if you were correct. How incriminating. "So and so looked at a page in a
publicly available catalog on a website." Bring out the leg irons. Give the rack a turn. Fetch the comfy chair. No one expects the Spanish
Inquisition!
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zed
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Sauron,
So, a lot of law enforcement guys are liars, as are government officials in general. You should know that.
In the jurisdiction where I reside, there are many officers that are permanently restricted to desk duty. They are not permitted to make arrests,
because they cannot testify in court. The local judges will not permit them to testify, because it has been proven that they are not credible
witnesses.
You should also know from reading the regulations, that acquiring an importers permit
isn't the end of the story. In obtaining one, you may give up some of your civil rights. Especially so, if you import any listed chemical. You
become subject to "inspections". These may be unannounced inspections. They could be walk throughs, paperwork inspections, or full blown searches.
Nagging phonecalls are also commonplace. Better off not to get the permit, and not just because it costs $1100.00! Truth is, they make you suffer.
I once worked at a small college where they drove us positively berzerk with such shit.
An ATF agent came regularly, to measure the useage of our one gallon of tax-free 100% grain alcohol. We had 300-600 students, but we actually used
very little ethanol. None-the- less his verdict was always the same.....He was suspicious, "AND WE WERE USING TOO MUCH ALCOHOL".
We finally gave up using this product all together. We were willing to pay the tax, so we wouldn't be screwed with, but our suppliers were not
willing to collect it. That meant we had to use heavily denatured ethyl-alcohol instead.
Our chromatography experiments no longer worked properly. Change the polarity of your solvent mix, and your rates of elution are altered.
Diversion control agents, or chemical company employees working at their behest, made our school's purchasing agent cry. They made groundless
accusation, after groundless accusation. It was one thing after another. Everything was suspect.
We couldn't replenish needed lab supplies, and our students suffered.
Our instructors were harassed and fearful of arrest or termination. They were stressed out of their minds.
Yet remarkably, we hadn't done a single thing improperly...we were completely legit.
So yes, Sauron....Perhaps I am a little paranoiac. I don't like to be messed with.
Do you blame me?
As for data mining. Yes, federal agents are very through. For those that must be concerned about such things, that attention to detail is a concern.
They have a lot of information they never act on, and rightly so. Conversely, when they do decide to act, they usually have mountains of
information, that collectively can look pretty damning, even if you really haven't done much.
Some of the guys see a drop of pine sap on the pavement, and they are pretty sure that it is evidence, that a gang of black islamo-terrorists has just
gang raped a baby Christian girl at the site.
The paranoia of law enforcement personnel is what fuels my paranoia. Here in the U.S., it's a good idea to do yourself a favor, and make yourself a
small target.
PS. This is really kind of fun. Just a few hours ago somebody U2Ued me, and accused me of being a cop. Not so! I'm a bored, over-weight,
middle-aged, ex-housewife. Are you Married?
[Edited on 17-10-2008 by zed]
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Sauron
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Yes. And divorced, and remarried for twenty years.
Since an importer's license is not required for anything but listed or scheduled stuff, which eugenol is not, it's irrelevant and off topic, isn't it?
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zed
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It came up in the thread. A poster complained. Said an agent had informed him he needed an importer's license to import. No qualifiers. Eugenol,
and every other chemical, would be effected, if true.
I've heard such reports elsewhere. Not a problem, for those of you outside the U.S..
But, possibly a problem for those of us here that have a hobby, or envision starting a fledgling business.
The agent may be over-reaching. The regs don't read that way. If you study them.....They actually seem pretty reasonable.
But, are the regs still the same? The problem is that the rules may be changed at anytime with very little public notice. And, that the DEA may read
the regs differently than we do. You really don't want to spend the next few years of your life either battling in court, or rotting in prison.
Chemrox seems to be saying, that the true situation is so murky, that he has asked for help from his Senator to obtain clarification.
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Sauron
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Read the forum. Lots of US members import chemicals, China is a popular source. Not one of those members has ever posted anything about Customs
demanding a DEA (or DHS) import permit/license/clearance.
Now if they had been importing red P and I2 that might be different.
Anyway this IS OT and so please do not seek to perpetuate the tangent or you are likely to hear from the Mod Squad.
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chemrox
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@Sauron- I think the DEA guy is full of shit too. I'm trying to resolve the question though since I was told directly. Only seems prudent and I
passed on the information in case the caution is apt. Eugenol is not on any list I know of ... yet. Maybe all the essential alcohols and aldehydes
will be in the future. Anyway, I probably shouldn't have rocked that boat.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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Sauron
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I think vanilline and safrole are the only ones that are listed, IIRC, but I haven't really made a close study, as I don't live there and don't really
give a damn. Vanillin is off the shelf here, though I have never even priced it. It's simply on the list of what the local suppliers keep ex stock.
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kalacrow
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Vanillin isnt listed.
http://www.deadiversion.usdoj.gov/21cfr/cfr/1310/1310_02.htm...
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