Experimentations in Cheap Oud

[roflwaffle]

I blended some quite aromatic/loud oud in with some (cheap) CK oud, mostly just to see what would happen. At first, it seemed very promising, big bold opening that was slightly softened by the honey camphor of the CK CO2, exactly as hoped. However, after given time to meld, the CK has dampened it... quite a bit. Too much. Instead of the oud raising up the CK, the CK beat it down to it's level of faint skin scent.

I am curious if the chromones or waxes are acting as a heavy fixative of sorts (with CO2 oils, as I understand it being lousy with them). So instead of writing off a failed cheap experiment, my mind went to work on how I'd prove that out. Fixatives are great, in known quantities, of the right types, but I don't know that these are really doing this oud any good, so... let's remove them!

Briefly, I think I can target mostly the chromones and the waxes by diluting them in ethanol, and freezing them. Winterization. Cold temps will crash out a portion of the waxes, chromones, and likely some collateral damage, and then cold filter them out quickly with a Buchner funnel, and I should be left with a less viscous, higher proportion of sesquiterpenes, stronger, less fixative base after evaping off the alcohol. I hope?

I'm wondering if anyone sees any glaring issues here, apart from wasting my time on silliness. Other option that seemed potentially viable would be to just run the CO2 in water through distillation, which should leave the heavy molecules behind, but, even with a small, not locked in wood matrix solution, I imagine will still take... a long run.

@Mr.P - have you ever tried to run a followup distillation on your CK resin extracts for luls? I imagine you've at least considered it. The remaining ethanol would come out as a foreshot, clean, or rotovap out the alcohol, then distill out the lighter compounds via conventional hydro distillation. Would it be oud oil? of course not. But potentilaly an interesting subset of compounds. Really only makes financial sense for CK as it's essentially free. (for commodity grade, not all chinese a. sinensis, obviously).

I suppose I'll know in a day or so. I've diluted 10ml of CK, and I can see a healthy crashed out portion after being in the chest freezer for 24h. I'll give it another day or so to ensure it has the time needed, and then see if i can filter as fast as possible (got the Buchner in the freezer too). Will be interesting to see if the crashed out part has a scent of is own or what the division ends up being. Keeps me off the streets I suppose 😀.

Any feedback on incorrect assumptions on my part would be appreciated! I'm certainly no expert here.

 

[roflwaffle]

Another interesting thing. So, since I had the dry ice, I ran some other chip in ethanol bottles i had as well.

The one interesting one I want to explore more is that in one of the samples, after evaporation, the oil separated into a black layer and a yellow layer. Now, this set of chips was from a sandal/oud codistilation once processed, so this amount of oil looking substance, and the separation itself is... surprising. I think i'll try to put it in a separating column and see if I can figure out what separated. It was only a small amount of chips in ethanol to aid in evaluation, but we'll see what i can ascertain.

 

[MaxFromHolland]

Well, the update we've all been waiting for. So I gave the oil a few days to settle

I lost about half a gram, but likely due to it stuck in the filter, left in the bottle (have to move fast), and other general losses. Not a big deal as this stuff is cheap as chips.

The viscosity is lighter. Now, this could be due to residual ethanol left in the solution (which would mean my losses were higher still), or it could be that more excess waxes/chromones were removed.

For the smell. Mixed results. I have applied one to each hand. The original one, I can tell that I have inadvertantly burnt off some of the initial top notes. Not extreme, but its there (not unsurprising as this was noted in the recent fermented cheese viet thread as a way to intentionally burn off top notes).

I do have a bit of congestion today, so scent notes will be a bit muted, but hopefully enough to still do a longevity and mid/base note side by side. In the mids, the filtered one appears to now be showing a bit stronger, but nothing that's blowing my mind.

So far, results fairly unimpressive. It could change with longer time to re-settle, or when my congestion clears, or be seen in blends to halt the dampening affect. Could also be that I didn't successfully get the solids out in filtering and all i have is a top notes burnt off version of the original, with a little residual alcohol to improve viscosity.

Good to have tried though. But probably you want to let it settle a few days and give it another sniff.
Otherwise maybe a simple re-distilling isn't such a bad option after all. Seems the whole dry ice route is quite time consuming too.

 

[roflwaffle]

Good to have tried though. But probably you want to let it settle a few days and give it another sniff.
Otherwise maybe a simple re-distilling isn't such a bad option after all. Seems the whole dry ice route is quite time consuming too.

Yes, redistillation is another option I considered, and one that's far less fiddily and time sensitive than dry ice, and we know that chromones generally wont come over in distillation, and waxes only if pushed hard into boya territory, as near as i understand it.

The winterization seemed like the easier path up front, but in practice at least at these temps, not the case. Also fairly expensive with ethanol and dry ice costs added, whereas distillation will be almost free, just time consuming, even if losses expected to be higher.

And agreed, a few more days/weeks may surprise me, but I figured no harm in an early assay. I did rinse the filter and collect what fell out after returning to room temp, and what was evap'd from that is quite a bit thicker than even the original oil, but not cloudy, so it seems at least something was filtered.

 

[Mr.P]

Yes, redistillation is another option I considered, and one that's far less fiddily and time sensitive than dry ice, and we know that chromones generally wont come over in distillation, and waxes only if pushed hard into boya territory, as near as i understand it.

The winterization seemed like the easier path up front, but in practice at least at these temps, not the case. Also fairly expensive with ethanol and dry ice costs added, whereas distillation will be almost free, just time consuming, even if losses expected to be higher.

And agreed, a few more days/weeks may surprise me, but I figured no harm in an early assay.

chromones do not come over in distillation? I thought they were part of the characteristic agarwood oil aroma! I haven't applied myself to really understanding the chemistry of the different species and extract types...

 

[MaxFromHolland]

chromones do not come over in distillation? I thought they were part of the characteristic agarwood oil aroma! I haven't applied myself to really understanding the chemistry of the different species and extract types...

Highly polar, do not let go of their surroundings easily + very low vapor pressure at 100°, means it takes a lot of steam to carry them over. So you get the top70% of the co2 long before any significant amount of the waxes and chromones.

 

[roflwaffle]

Highly polar, do not let go of their surroundings easily + very low vapor pressure at 100°, means it takes a lot of steam to carry them over. So you get the top70% of the co2 long before any significant amount of the waxes and chromones.

Yes, that was my understanding as well. I think i said above they 'dont come over' but they prob do at some point into the boya/late fractions along with the waxes. I just had internalized that they were not very present in oil GCMS. Thanks for the more complete answer. (I hand wave at times)

 

[Mr.P]

Yes, that was my understanding as well. I think i said above they 'dont come over' but they prob do at some point into the boya/late fractions along with the waxes. I just had internalized that they were not very present in oil GCMS. Thanks for the more complete answer. (I hand wave at times)

OK I just did a little reading and now I get it, the chromones are part of the combusted wood profile but are only semi volatile so they are not a significant part of the essential oil… and it's mainly when they pyrolize that they produce a characteristic aroma.

 

[roflwaffle]

Ok, I'm picking this back up after a bit of a detour. I think my next steps are distillation. I have 2 separate things here to run through a microscale.

1) bog standard CK CO2, plenty enough to run.
2) eth extraction of CK, evaped to thick goo, prob 30ml or so

Not been able to find much prior art here, but would be curious any tips.

Planning on a bain marie in, I dunno, mineral oil, since I don't have a mantle heater, and I'd like generally even heating. Prob less risk of scorching, shorter run.

I don't have a hydrosol return path setup on this little guy, so this will be a manual drain and stall and resume. Cooling will be as minimal as I can do, small pump of room temp water through condenser at a low rate, thinking is minimizing how much is lost via condenser path, but open to suggestions

Since both co2 and eth gunk will float, prob some considerations there. No magnetic plate, so boiling stones or potentially pour gunk over wood chips to break up surface tension, not sure if required, bit out of my norm, so maybe overthinking it.

No clue what expected yields would be, prob batch dependent, and waxes/chromones mostly left in the pot (collected at the end for no specific use or thoughts yet, but maybe just for augmenting incense use or something)

At the end, sep funnel and let settle. Possibly heat lamp or dried bath says to remove residual water, not sure how much will be required, but not looking forward to transfer/filter losses.

Depending on still load, collect as fractions, but not sure I really have enough to warrant other than collecting during hydrosol flushes. Really hoping for the prior mentioned like 8 hour or so run vs multi day, but I'll def push the tails anyway just to learn

Anything I'm not considering or missing out on?

 

[MaxFromHolland]

Ok, I'm picking this back up after a bit of a detour. I think my next steps are distillation. I have 2 separate things here to run through a microscale.

1) bog standard CK CO2, plenty enough to run.
2) eth extraction of CK, evaped to thick goo, prob 30ml or so

Not been able to find much prior art here, but would be curious any tips.

Planning on a bain marie in, I dunno, mineral oil, since I don't have a mantle heater, and I'd like generally even heating. Prob less risk of scorching, shorter run.

I don't have a hydrosol return path setup on this little guy, so this will be a manual drain and stall and resume. Cooling will be as minimal as I can do, small pump of room temp water through condenser at a low rate, thinking is minimizing how much is lost via condenser path, but open to suggestions

Since both co2 and eth gunk will float, prob some considerations there. No magnetic plate, so boiling stones or potentially pour gunk over wood chips to break up surface tension, not sure if required, bit out of my norm, so maybe overthinking it.

No clue what expected yields would be, prob batch dependent, and waxes/chromones mostly left in the pot (collected at the end for no specific use or thoughts yet, but maybe just for augmenting incense use or something)

At the end, sep funnel and let settle. Possibly heat lamp or dried bath says to remove residual water, not sure how much will be required, but not looking forward to transfer/filter losses.

Depending on still load, collect as fractions, but not sure I really have enough to warrant other than collecting during hydrosol flushes. Really hoping for the prior mentioned like 8 hour or so run vs multi day, but I'll def push the tails anyway just to learn

Anything I'm not considering or missing out on?

Cant quite see why you would need something to break surface tension, water will do so while bubbling?

Not sure how the 'eth gunk' will behavee, never tried that.

That chromones leftover fraction, i saw mentioned as specialty ingredient somewhere, so i would put it in expensive looking bottle 🙂

Looking forward to read how things fared 🤓

 

[roflwaffle]

Cant quite see why you would need something to break surface tension, water will do so while bubbling?

I Could def be overthinking it. Never distilled a thick oil floating on water before.

And haha, yes I suppose waxy chromones might have a use, I'm curious if the remainder will cool into a boya like consistency