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Cheap Oud Replacement?

Discussion in 'General' started by Yahya Schiltz-Rouse, Oct 14, 2020.

  1. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    I am interested in hearing about the outcome of a bacterial distillation. I think you can remove a lot of the lactic acid by adding solid magnesium hydroxide to the oil. Maybe re-distilling it as well. Acids are soluble in water not oil. Then using molecular sieves or anhydrous calcium sulfate to get rid of excess water.
     
    Last edited: Oct 23, 2020
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  2. Abu Amir

    Abu Amir True Ouddict

    Yes me to lets see if some one have done it or know some one, magnisum sulfate will be stucked to the water and sink to bottom but i dont think there are problem to destill with lactic acid, becuse as u said its water soluble and will not blend with oil the problem are if there have been anlther unwated bacterial growth that generate compunds that are oil soluble the smell will be in the oil, we hear this alot people say barnyard smell and so on :)
     
  3. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    I have a GC-MS report from a very barnyard smelling agarwood oil from eden botanicals and it has butyric acid in it. Oud distillers should add magnesium or calcium hydroxide to barn oils to react with the butyric acid in the aqueous layer.
     
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  4. Abu Amir

    Abu Amir True Ouddict

    Oh finaly now we know what is this batnyard are it is butric acid. Yes they can netrulised it easy with magnisum hydroxide as base, now when u said it is this whish case barnyard smell
     
  5. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    I have attached the report below.
     

    Attached Files:

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  6. Abu Amir

    Abu Amir True Ouddict

    I cant open it do i need computer? I try with phone
     
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  7. Abu Amir

    Abu Amir True Ouddict

    Now i can open
     
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  8. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

  9. Abu Amir

    Abu Amir True Ouddict

    0,02% not alot but this acid stinkkkks its vomit smell i think smell are in ppm range so 0,02% is enough to smell shitty
     
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  10. Abu Amir

    Abu Amir True Ouddict

    Do u work as chemist? Or u send sampel to company?
    I really like your way brother. First time i know barnyard smell are bytric acid, it is not easy to know without exam report as u have unfortnally many dont do GCMS to devolop becuse its expensive but for those who want to devolop they must exam what they do why and how and so on.
     
  11. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    I just asked eden botanicals to send me a report. They did it for free.
     
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  12. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    Apparently some of the compounds in oud are sensitive to pH and can undergo retro-aldol reactions catalyzed by surfactants.
     
    Last edited: Nov 6, 2020
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  13. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    So I bought a bunch of chemicals to attempt making dihydrokaranone (a chemical in Oud) from 2-hydroxy eremophilone. Basically buddha wood oil has 3 significant constituents eremophilone, 2 hydroxy eremophilone, and hydroxy dihydroeremophilone so I used this as a precursor.

    I found a scientific paper the describes how ketones (-one group) can be reduced using a combination of zinc metal, ammonium chloride, and tetrahydrofuran. When I added buddha wood to this mixture not all of the zinc reacted as I had expected and due to the possibility of side products I consider this a failure.

    After this reduction, I sought to isomerize the resulting allylic alcohol into a ketone using ruthenium nanoparticles I created in situ from ruthenium acetate. Adding molecular sieves (4A) to this mixture seemed to accelerate some kind of reaction as the oil became darker, though that may have been some sort of polymerization.

    After this step I was going to repeat the ketone reduction using zinc, however, ruthenium can transfer hydrogenate ketones using isopropyl alcohol so I skipped this step and went straight to the dehydration of the alcohol using acid.

    I quickly found that the oil polymerizes in contact with concentrated phosphoric acid so the critical dehydration step could not be completed on acid. Now I feel as though I have wasted a ton of money. The oil was in general extremely difficult to recover from water washing so I ended up wasting a lot of my buddha wood oil, which comes from the once plentiful forests of Australia.

    The only other alternative I see is to reduce the ketones using MPV reduction (isopropyl alcohol + molecular sieves) followed by the isomerization (ruthenium NP) followed by dehydration on molecular sieves with heat (no acid).

    In my last attempt I added ruthenium acetate (in ethanol) + molecular sieves + (91%) isopropyl alcohol simultaneously and let the reaction proceed. It became darker and began to smell like caramel and something chemical/awful and when I tried to wash the oil using liquid deodorized coconut oil and water to remove the ruthenium nanoparticles I ended up losing a lot of product. Then I attempted dehydration (removal of OH group and creation of a double bond) of the oil I could collected using distillation. At first I noticed the caramel/chemical smell I previously mentioned, however a pleasant dry pink wood aroma developed. This was not the "greatest aroma" I was expecting after reading a paper on dihydrokaranone, however, it is exotic and interesting and maybe it even is dihydrokaranone. I kinda doubt it though.

    Another experiment I have tried was to chemically reduce (adding hydrogen atoms) vetiver oil using baker's yeast. I added a lot of vetiver oil (with a little buddha wood) to a sugar + vegemite+yeast extract solution with two emulsifiers (tween 20 and TUDCA), however, the combination proved too damaging to the yeast and only after a 2 days in the warm sun did I see any gas generation (a sign of living yeast). The product did have a much smoother aroma that either vetiver or buddha wood giving me hope that this could be used to improve oils. I tried to remove the oil by washing the mixture with bestine (paint thinner), however, the solution did not separate well and all of the product became garbage. I attempted this reduction again without emulsifiers and the vetiver smelled worse (smokey).
     
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  14. DubOudh

    DubOudh Aster Oudh

    So....hard to reproduce?
     
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  15. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    For sure. Buddha wood seems like it has a tendency to polymerize on its own making chemical reactions difficult. I had to make the ruthenium acetate from ruthenium tetroxide by mixing ruthenium metal + bleach + HCl + NaCl and then I added dehydrated sodium acetate and heated it in ethanol. When I mixed the buddha wood oil + ruthenium acetate solution + isopropanol + molecular sieves it created a caramel smell. Further heating produced an exotic incense aroma I would not associate with the ouds I have smelled. The smell did kinda numb my brain though like oud.
     
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  16. Abu Amir

    Abu Amir True Ouddict

    It will be hard to make any conclutions with so many stuff in the oils. I think isolating the eremophilione first and after try the reactions. Very good work that you try. And please if u have reaction sheme put it
     
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  17. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    Screen Shot 2020-11-25 at 8.14.40 PM.png

    1: Reduction of Dione to alpha-hydroxy ketone

    Attempt 1: Reduction with THF+Zn+NH4Cl (Failed)
    Attempt 2: Transfer hydrogenation with Isopropyl alcohol (IPA) on Ru nanoparticles + molecular sieves
    Attempt 3: Reduction using baker's yeast* (Product was found to smell like smokey caramel)

    2: Isomerization of allylic alcohol

    Attempt 1,2: Ruthenium acetate + reflux

    3: Reduction of Dione

    Attempt 1,2: Transfer hydrogenation with Isopropyl alcohol (IPA) on Ru nanoparticles + molecular sieves

    4: Dehydration of alcohol

    Attempt 1: Dehydration of alcohol to alkene using Phosphoric acid +Molecular Sieves (Failed; polymerized)
    Attempt 2: Dehydration on molecular sieves (Smokey caramel smell formed)
    Attempt 3: Heating product in liquid coconut oil with molecular sieves (Smokey caramel smell formed)

    Note: Only the last two steps matter since the primary precursor in Buddha wood is the dione starting at step 3. Since the reduction of the dione is redundant you can think of step 1 and 3 as the same step.
     
    Last edited: Nov 26, 2020 at 2:14 AM
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  18. Abu Amir

    Abu Amir True Ouddict

    There must be stereochemistry and sterics are involved. Futher conversations a developing a clear idea of Riley reaction(2), tautomerization(3), selective reduction of saturated ketone(4), elimination or dehydration(5).
    Maybe starting with this molecule are harder than another
    I also cheek with som other people to see what they say 9E57B976-78E4-4F8B-A97D-CAEAAF5971CC.jpeg
     
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  19. Yahya Schiltz-Rouse

    Yahya Schiltz-Rouse Whats this Oud About?

    Reaction #2 is not a riley reaction (riley oxidation?) but is an allylic alcohol isomerization. Many noble metal complexes can rearrange allylic alcohols, which is why I used ruthenium acetate. The added bonus of this is that this forms ruthenium nanoparticles, which can reduce the dione via transfer hydrogenation. This step is tricky because there is nothing stopping it from reducing the compound all the way to a diol or reducing the wrong keto group. If the wrong keto group is reduced the ruthenium can isomerize this new allylic alcohol reducing the double bond of the isopropene group on the bottom right. Heat can isomerize the alpha hydroxy ketone and because the more stable configuration is the one shown, I hypothesize that it is more likely to form. Unfortunately Buddha wood is very pH and oxygen sensitive and very rapidly polymerizes into a hard amber resin. The cap on the bottle has become hard and crusty from oxidation over a matter of weeks. To make matters even more difficult the whole reaction requires the absence of acids or base because dihydrokaranone like pulegone can potentially undergo retro-aldol reactions in steam.
    11775-19-27IP1.png
     
    Last edited: Nov 29, 2020 at 9:27 PM
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  20. Abu Amir

    Abu Amir True Ouddict

    Yes this will be intresting. Do u have acesse to other reducing againts? Like LiAlH4 and NaBH4 ? Hard to handel LiAlH4 but never know what will be :)
     

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