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Thread: Schiff's bases

  1. #61
    Basenotes Junkie Nizan's Avatar
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    Default Re: Schiff's bases

    Paul - just for comparison, your benzaldehyde base smells of almonds throughout the drydown? The indole thing loses its almond smell quite quickly..

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    Default Re: Schiff's bases

    It is highly unlikely that you made a reaction product between Benzaldehyde and Indole Nizan, simply by mixing the two chemicals together and warming them. Indole is much less likely to react than Methyl Anthranilate. You probably have a mixture of Indole and Benzaldehyde which yo are smelling. Benzaldehyde is more volatile than Indole, and Indole is so much stronger (in my opinion), which is why the almond smell goes so quickly.

  3. #63
    Basenotes Junkie Nizan's Avatar
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    Default Re: Schiff's bases

    I figured :\
    The only mystery now is why it became thick and red.. Could be that some of the
    residual acid in the benzaldehyde reacted? Or that just a small portion reacted?
    What a bummer..

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    Default Re: Schiff's bases

    Are you sure you didn't just make a paste of the two chemicals? To make a Schiif's Base you need to mix Molar amounts of the two. So Indole has a molecular weight of 117.15 and Benzaldehyde has a weight of 106.12. So you are mixing 11.7 gms of Indole with 10.6 gms of Benzaldehyde; a lot of solid (Indole) to mix with the liquid (Benzaldehyde). Indole discolours very easily, and I'm not saying that you did not produce any Schiff''s Base, just that most of your two reagents remained unreacted.

  5. #65
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    Yeah, I mixed then at 10:9.. Too bad it's diluted now.. I could have kept warming it
    to see if something happens..

  6. #66
    Paul Kiler
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    Default Re: Schiff's bases

    Quote Originally Posted by julian35 View Post
    Paul, absolutely brilliant Schiff's Base Compendium. Thank you for putting such a great document together and for making it available.

    (p.s. - Also wanted to mention I recently purchased a fantastic pair of Koure frames, I know you are someone that would appreciate that from a post I read somewhere.
    Paul's Headshot.jpg Oh Yes, Love my Koure Frames, Here's my headshot on the Red Carpet for the Taste Awards...
    And you are very welcome for the Compendium, I could not find any other similar resource for my own education, so I had to make it myself....
    Paul Kiler
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    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

  7. #67
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    Default Re: Schiff's bases

    Went back to the drawing board today. I'm sure I got a lot wrong last time and made too many assumptions.

    I'm wanting to make sure I do everything right this time so I have a few questions:

    1. How does one know when the reaction is DEFINITELY complete?
    2. Are schiff bases definitely supposed to be cloudy after they cool or is cloudiness an indication that the process is complete when they are still hot?

    I have four small samples brewing and I'm sure one of them isn't reacting at all, which is ok, it was an experiment and no, it isn't on Paul's compendium (Hexyl Cinnamic Aldehyde). The other three are definitely reacting because they've changed color and they have gotten thicker but not that much more thick than they were prior to heating, I've had them on the hot plate at 70C for over an hour now.

    Anisic Aldehyde/Methyl Anthranilate: Got a little yellow but not a lot
    Cinnamic Aldehyde/Methyl Anthranilate: Dark brown, almost black, can not see light through it in the vial
    C-11/Methyl Anthranilate: Turned a rich transparent orange/brown
    Hexyl Cinnamic Aldehyde/Methyl Anthranilate: No apparent change/reaction

    None of them are "very thick", just a bit more thick than before heating and none of them are cloudy... These reactions seem counter to what has been described (thick and cloudy).
    Last edited by JEBeasley; 8th February 2014 at 01:38 AM.
    Justin E. Beasley

  8. #68

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    Went back to the drawing board today. I'm sure I got a lot wrong last time and made too many assumptions.

    I'm wanting to make sure I do everything right this time so I have a few questions:

    1. How does one know when the reaction is DEFINITELY complete?
    2. Are schiff bases definitely supposed to be cloudy after they cool or is cloudiness an indication that the process is complete when they are still hot?

    I have four small samples brewing and I'm sure one of them isn't reacting at all, which is ok, it was an experiment and no, it isn't on Paul's compendium (Hexyl Cinnamic Aldehyde). The other three are definitely reacting because they've changed color and they have gotten thicker but not that much more thick than they were prior to heating, I've had them on the hot plate at 70C for over an hour now.

    Anisic Aldehyde/Methyl Anthranilate: Got a little yellow but not a lot
    Cinnamic Aldehyde/Methyl Anthranilate: Dark brown, almost black, can not see light through it in the vial
    C-11/Methyl Anthranilate: Turned a rich transparent orange/brown
    Hexyl Cinnamic Aldehyde/Methyl Anthranilate: No apparent change/reaction

    None of them are "very thick", just a bit more thick than before heating and none of them are cloudy... These reactions seem counter to what has been described (thick and cloudy).

    good questions Justin,

    i guess one is suppose to just mix stuff and guess....
    As this is a DIY forum to discuss Perfumery, I do not think that you comparing the size of your retort stands with each other is of much use. This Forum is not about Organic Chemistry or Chemical Synthesis, it is about Perfumery.

  9. #69
    Basenotes Junkie Nizan's Avatar
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    Default Re: Schiff's bases

    How much are you making, Justin? Could it be that for small quantities and open vials, the water just evaporates in the process?

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    Default Re: Schiff's bases

    Quote Originally Posted by Nizan View Post
    How much are you making, Justin? Could it be that for small quantities and open vials, the water just evaporates in the process?
    They got thicker, the Cinnamic Aldehyde turned almost black and is thick as tar after it cooled. Everything else still flows albeit more like honey. I made three of them around 3.5g and one around .3g so they are small but only one I would consider truly micro. They never did get cloudy, it is possible that the water evaporated, there is a small amount of condensation around the upper 1/2 of the vials but it's a very fine mist. All said I had them on the hot plate for around two hours so I can't imagine the reaction never completed.

    I was curious if ketones would react so I made a micro sample of methyl cedryl ketone + methyl anthranilate too. Oddly it is quite a bit thicker, darker and smells less sweet and more pissy like cedar... I have no idea if this was a reaction or if it just condensed from the long cook time. The Hexyl Cinnamic Aldehyde got thicker and smells different too but once again I have no idea if it reacted. If the Hexyl Cinnamic Aldehyde actually did react then it was the slowest one to react with the least amount of visual change. This weekend I'm going to try a few others on Pauls compendium and not on his compendium (C12mna, C18, C14, Lyral, Helional). Ideally I'd like to have a small working sample of everything I can turn into a base, I figure "why not" more variety to work with and aldehydes are cheap and go bad quickly anyway.

    I've been analyzing Dzing! lately, it's one of my current favorites, it's such an even smelling perfume from start to finish that it got me thinking about how a perfume could be entirely comprised of dilute bases and more stable EOs. Even if it isn't made this way it seemed like an interesting concept to explore so I'm now hell bent on making as many bases as I can. Now if I just had a list of everything that can be made into a base, lol.
    Last edited by JEBeasley; 8th February 2014 at 07:05 AM.
    Justin E. Beasley

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    Quote Originally Posted by luigi_g View Post
    good questions Justin,

    i guess one is suppose to just mix stuff and guess....
    That's pretty much how I do most things, lol! Over all I'd say I'm pretty lucky to have all of my body parts and to be alive but I honestly don't know how to be any other way.
    Last edited by JEBeasley; 8th February 2014 at 07:18 AM.
    Justin E. Beasley

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    Default Re: Schiff's bases

    Quote Originally Posted by Nizan View Post
    Paul - just for comparison, your benzaldehyde base smells of almonds throughout the drydown? The indole thing loses its almond smell quite quickly..
    Nizan, I'm not quite sure to what you refer, but if you are asking about whetehr I made ther Schiff base with these items, then no is the answer. The Compendium is simply a repository of research infromation, not my personal experience.

    Mr. JEBeasley , I can tell you that M.A. / Helional Schiff base is very close to a soild when at rest and room temp. So it's entirely possible that others could be in a similar state when cooled. But that's the only one I can recall that gets that way. But I'll bet it liquifies when warmer.

    PK
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    Default Re: Schiff's bases

    If your "Schiff's Base" is cloudy when cool, there is water present and so the reaction is not complete. By removing the water you drive the retain to completeness. I was never able to get Amyl Cinnamic Aldehyde or Hexyl Cinnamic Aldehyde to react with Methyl Anthranilate, to form Schiff's Bases. Heating at 70 deg C for several hours is too hot (I think), you will not produce a good quality. I have found that to rest a Ketone, takes much longer, if at all without using a vacuum to remove water. Despite what others think, I don't think it possible to make a Schiff's Base using Aldehyde C14 C16 or C18, for reasons given above. Of course you should all experiment as that is how we learn.

    So Paul, the Compendium of Schiff's Bases you provided are simply a list you have; you have not made any yourself?

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    Default Re: Schiff's bases

    Nizan, I'm not quite sure to what you refer, but if you are asking about whetehr I made ther Schiff base with these items, then no is the answer. The Compendium is simply a repository of research infromation, not my personal experience.
    Ho, didn't realize that. I will report how the benzaldehyde went once I get my MA.

    By removing the water you drive the retain to completeness.
    David, do you mean that the presence of water somehow quenches the reaction?

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    Default Re: Schiff's bases

    When mixing the aldehyde with Merthyl Anthranilate, you get the Schiff's Base plus water. This continues until an equilibrium is reached. To encourage the reaction to proceed in the direction you want it is necessary to remove the water.

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    Default Re: Schiff's bases

    Quote Originally Posted by luigi_g View Post
    good questions Justin,

    i guess one is suppose to just mix stuff and guess....
    OOH, mee-ow!!

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    Quote Originally Posted by David Ruskin View Post
    If your "Schiff's Base" is cloudy when cool, there is water present and so the reaction is not complete. By removing the water you drive the retain to completeness. I was never able to get Amyl Cinnamic Aldehyde or Hexyl Cinnamic Aldehyde to react with Methyl Anthranilate, to form Schiff's Bases. Heating at 70 deg C for several hours is too hot (I think), you will not produce a good quality. I have found that to rest a Ketone, takes much longer, if at all without using a vacuum to remove water. Despite what others think, I don't think it possible to make a Schiff's Base using Aldehyde C14 C16 or C18, for reasons given above. Of course you should all experiment as that is how we learn.

    So Paul, the Compendium of Schiff's Bases you provided are simply a list you have; you have not made any yourself?
    If two hours @ 70C is too hot for too long then what are the correct times and temps or how can we find this out? When you say "not produce a good quality" does that mean it's oxidized by the heat or it's burnt or... What I made smells fine, the C11 base smells like an idealized **shudder** myrrh, without being sweet but it seems usable. I don't know though, I have yet to try to dilute them so maybe they are plasticized too much to be of use?
    Justin E. Beasley

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    I diluted my C11 schiff base sample today, I had to heat it with the solvent to get it all to dissolve. I only made a micro amount, enough to dilute and fill a 1 dram dropper bottle. The diluted sample is very cloudy like most of the absolutes I dilute. I probably won't filter this one because it's such a small amount that I would lose half of it but I will try to dilute and "dry" a couple others as soon as I can find my nitrile gloves. Since all of my absolutes are cloudy I might just wait and filter and dry the whole perfume, if it even get's to that stage.

    This C-11 is interesting, it's a musty, dry, grapey, powdery version of myrrh, I can see it being very useful in incense accords with frankincense. Even if it's over-cooked I still like it.
    Justin E. Beasley

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    Paul Kiler
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    Default Re: Schiff's bases

    Quote Originally Posted by David Ruskin View Post
    So Paul, the Compendium of Schiff's Bases you provided are simply a list you have; you have not made any yourself?
    For me the Compendium was about knowing more what something was supposed to smell like, as gathered from sources. There was/is hope to make some of them, but it was a place to put and cross reference the information, that I'd not seen before in one spot.. It is a comparative analysis paper. And now we all have a stepping stone to embark from, don't we...? It was also prompted by working with the Perfume Chemist friend I have who wanted to make some for me. So it was more about finding things that sounded interesting, and then to have others do the work for me to order so that I could get that material. Sort of delegating the tasks so I can use my skills elsewhere.

    This Perfume Chemist friend talked about making all kinds of cool things he knows about, cool aldehydes not currently Produced, Schiff Bases not currently produced, Rum Absolute... Etc...

    I'm sure he'll come into play when we get Perfumer Spupply House up and in swing, making things for us that no one else will be able to sell.

    I have made one schiff's base, Cuminaldehyde and MA, which didn't change much from Cuminaldehdye...

    So, That's where it all stands presently...

    PK
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    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    If two hours @ 70C is too hot for too long then what are the correct times and temps or how can we find this out? When you say "not produce a good quality" does that mean it's oxidized by the heat or it's burnt or... What I made smells fine, the C11 base smells like an idealized **shudder** myrrh, without being sweet but it seems usable. I don't know though, I have yet to try to dilute them so maybe they are plasticized too much to be of use?
    The one article I read describing the synthesis of a Schiff's Base using Methyl ANthranilate, said the temperature should be no higher than 50 deg C. If your sample, cooked at 70 deg smells fine, then it is OK, and I was wrong. I thought that at 70 deg there would be danger of burning. Justin, why do you think your Absolutes go cloudy when diluted? Are you diluting into alcohol that contains too much water? Anyway, I'm glad you like what you have done with Aldehyde C11. You should try making a Base with Aldehyde C12 MNA; one that I particularly like.

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    Default Re: Schiff's bases

    I don't know why my absolutes might be cloudy... Are they of poor quality? Perhaps I don't heat them enough so that they dissolve? I use 95%+ cane alcohol from Alchemical Solutions.
    http://organicalcohol.com/store/inde...cohol-1-gallon
    Is this a bad sign? If I make a blend from mostly EO's or all EO's it will be cloudy every single time, without exception. If I let the blend sit undisturbed for a couple of days it will clear up but as soon as I agitate it gets cloudy again. I assumed it was a small amount of naturally occurring water in the absolutes. Do resellers add water in order to add weight to absolutes? It could also be due to temps in my work room, I keep it pretty cold in there since I have no heater register in that back room.
    Last edited by JEBeasley; 9th February 2014 at 08:50 AM.
    Justin E. Beasley

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    Default Re: Schiff's bases

    Justin - this hasn't happened to me often. At what concentrations are you getting the cloudiness?

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    Default Re: Schiff's bases

    By the very definition of an Absolute I would have thought they would be soluble in Absolute Alcohol. That is the way an Absolute is prepared. Seems to me that there is something in your Absolutes or your alcohol that is not soluble. The common material here is the alcohol.

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    Quote Originally Posted by Nizan View Post
    Justin - this hasn't happened to me often. At what concentrations are you getting the cloudiness?
    I dilute all of my absolutes @ 10%. I just thought of something... the alcohol I have been using (cane) is NOT ideal because it has such a strong malty odor so I dilute everything with 40% DPG and 60% alcohol to keep the malt and alcohol to a minimum, sometimes it overpowers the smell of the material it is diluting. So, it's probably the DPG... Sorry, I forgot about that. I was concerned for a minute but I went in there and looked at them all and thought about my dilution process.

    Out of the 14 absolutes I currently have diluted six are very cloudy, with some larger sediment, so that I can not see the dropper inside and three are half cloudy, the rest are clear with sediment floating around on the bottom or a thin layer that doesn't stay diluted.
    Justin E. Beasley

  25. #85
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    Default Re: Schiff's bases

    Have you tried mixing your DPG with your alcohol, to see what happens? Also, have you tried diluting an Absolute with only your DPG, to see what happens? And finally, have you tried just using your alcohol with your absolutes? As far as I am aware DPG should cause no problems with most Absolutes (not all, but most).

    If your alcohol smells strongly, of anything, it is not suitable for Perfumery.

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    Quote Originally Posted by David Ruskin View Post
    Have you tried mixing your DPG with your alcohol, to see what happens? Also, have you tried diluting an Absolute with only your DPG, to see what happens? And finally, have you tried just using your alcohol with your absolutes? As far as I am aware DPG should cause no problems with most Absolutes (not all, but most).
    If your alcohol smells strongly, of anything, it is not suitable for Perfumery.
    I dilute all of my AC's with the same DPG + Alc mixture and ratio, I only get clouding with a couple AC's that probably aren't solvent in DPG (I'll have to look them up). The DPG + Alc combo does not cloud by itself, only when combined with other materials.

    When I purchased the Ethyl Alcohol I was not aware that the three different types available by that company would be so different, after all 95% alc is 95% alcohol and 5% water right? Well, as it turned out, I got the alc home and it smelled more malty than the perfumers alc I purchased from creating perfume. I made a couple dilutions @ 10% and realized that I couldn't smell the material over the alcohol because the alcohol smell and maltiness were too strong so I cut my dilutions with 40% DPG and THEN I was able to smell the material from the bottle...

    Since I've joined this board I have spoken with another member who had exactly the same issue with the same alcohol from the same place, this was in a thread before the board change. I planned on finishing off the gallon of cane alc I have and then go for denatured from Remet or something. After those initial dilutions, which smelled overly malty and alcoholic, I never diluted with plain alcohol again and didn't look back until now. It looks as though by trying to solve one problem I created another, bleh.

    I have not tried DPG only + absolutes
    I have not tried Alc only + absolutes

    I will experiment with my absolutes and DPG/Alc soon to see if I can isolate the problem. It will take a couple of days to get this hammered out as I have a lot on my plate right now but I'll report back when I do.

    In retrospect, it is also possible that the schiff base I made is not entirely soluble in DPG and thus is cloudy as a result of using 40% DPG in the dilution, I will only know by creating another sample and diluting it with alcohol only. Bottom line is I need new alcohol in order to help root out some of these issues. I'll look through the alcohol threads and see which one Paul buys from Remet, hopefully that will be suitable for absolute dilution - does anyone know? Should I be diluting all materials with pure grain alcohol and using the denatured blend for the final perfume dilution? Grape alcohol only or will grain alcohol do? Supposedly grape has the least smell but it's twice the cost.

    Thanks for your help.
    Last edited by JEBeasley; 9th February 2014 at 09:02 PM.
    Justin E. Beasley

  27. #87

    Default Re: Schiff's bases

    If the Absolue dont dissolve in Alcohol, reduce the concentration and or try warm up a bit (to max 40 celsius)
    Depending on your room temperature, this can work.

  28. #88

    Default Re: Schiff's bases

    I have question about producing Shiff bases. I made some MA / Citral yesterday after reading here,
    but it didnt come red color as usual. Ok i didnt heat that much al usual. It remain yellow. (60 degrees at 30 minutes).

    Im looking for solution to catalyse the process without heat them to much, because aldehydes are sensitive
    to temperature. Can vacuum do the job? I mean by reducing atomspheric pression, they sould react better in theory.

    What you think about?

    Another thing, some Shiff base dont change much color at heating process, but become darker next day after some hours at room temp.
    Last edited by bigbang; 10th February 2014 at 08:48 AM.

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    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    I dilute all of my AC's with the same DPG + Alc mixture and ratio, I only get clouding with a couple AC's that probably aren't solvent in DPG (I'll have to look them up). The DPG + Alc combo does not cloud by itself, only when combined with other materials.

    When I purchased the Ethyl Alcohol I was not aware that the three different types available by that company would be so different, after all 95% alc is 95% alcohol and 5% water right? Well, as it turned out, I got the alc home and it smelled more malty than the perfumers alc I purchased from creating perfume. I made a couple dilutions @ 10% and realized that I couldn't smell the material over the alcohol because the alcohol smell and maltiness were too strong so I cut my dilutions with 40% DPG and THEN I was able to smell the material from the bottle...

    Since I've joined this board I have spoken with another member who had exactly the same issue with the same alcohol from the same place, this was in a thread before the board change. I planned on finishing off the gallon of cane alc I have and then go for denatured from Remet or something. After those initial dilutions, which smelled overly malty and alcoholic, I never diluted with plain alcohol again and didn't look back until now. It looks as though by trying to solve one problem I created another, bleh.

    I have not tried DPG only + absolutes
    I have not tried Alc only + absolutes

    I will experiment with my absolutes and DPG/Alc soon to see if I can isolate the problem. It will take a couple of days to get this hammered out as I have a lot on my plate right now but I'll report back when I do.

    In retrospect, it is also possible that the schiff base I made is not entirely soluble in DPG and thus is cloudy as a result of using 40% DPG in the dilution, I will only know by creating another sample and diluting it with alcohol only. Bottom line is I need new alcohol in order to help root out some of these issues. I'll look through the alcohol threads and see which one Paul buys from Remet, hopefully that will be suitable for absolute dilution - does anyone know? Should I be diluting all materials with pure grain alcohol and using the denatured blend for the final perfume dilution? Grape alcohol only or will grain alcohol do? Supposedly grape has the least smell but it's twice the cost.

    Thanks for your help.
    When I was working, the only time we used alcohol was to dilute our finished fragrances. Alcohol was never used as a solvent to dilute individual ingredients. Other, more suitable solvents were always used. So if the end product was going to be water based (such as Shampoo, Shower Gel, Hard Surface Cleaner etc. ) or if it was a fine fragrance, the solvent we used was DPG. If the end product was oil based (such as massage oil, candle, body cream etc.) a more suitable solvent was used. From memory we never had very few Absolutes that did not dissolve in DPG, although for some we used either Benzyl Benzoate or Benzyl Alcohol.

    I still maintain that if your Schiff Base is cloudy, there is water present.

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    Default Re: Schiff's bases

    Quote Originally Posted by bigbang View Post
    I have question about producing Shiff bases. I made some MA / Citral yesterday after reading here,
    but it didnt come red color as usual. Ok i didnt heat that much al usual. It remain yellow. (60 degrees at 30 minutes).

    Im looking for solution to catalyse the process without heat them to much, because aldehydes are sensitive
    to temperature. Can vacuum do the job? I mean by reducing atomspheric pression, they sould react better in theory.

    What you think about?

    Another thing, some Shiff base dont change much color at heating process, but become darker next day after some hours at room temp.
    To encourage the reaction, it is a good idea to remove the water that is being formed. A vacuum should help to do this.

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    I was a base makin' fool today. I made a bunch of small batches of most of the aldehydes I have plus a few ketones. The only ones I have that I didn't try to make are C-16 and a remake of C-11. Most of them I heated @ 60C for about 30-60 min; the ketones, C14 & C18 went longer as explained below. All of these were made by combining Methyl Anthranilate. I took pictures of the bases with their mother AC behind each base so that you can see the color difference. The Methyl Anthranilate is the purplish hewed bottle on the far right. I made 17 in all but the C-11 isn't shown as I diluted it already. I'll probably remake the C-11 base anyway.

    So, interestingly, the Raspberry Ketone + Methyl anthranilate turned a nice shade of orange-brown. The ketones took longer and had to be heated at higher temps in order to get color change and condensation indicating water evaporation. I got water condensation in the vial and color change to yellow with C14 and C18 but I had to heat them quite a bit longer and at much higher temps (50C for 30min + 70C for 30 min + 80C for 30 min). David said he was never able to get them to react so it's possible I merely cooked them until they were off color with some water evaporation/condensation and they aren't actually bases... HOWEVER they DO smell quite a bit different from the original combined materials and are more interesting methinks - both the C14 and C18 smell sweeter and deeper. Some of the bases came out cloudy, some are thicker than others, the color varies from light yellow to orange to brown to black, etc. As you can see the cinnamic aldehyde turned almost black and thick as tar, it is still black @ 10% dilution with alc.

    Tomorrow I will dab the condensation out of the vials with paper towels or cotton swabs. I found that if I twist half of a paper towel, bend 1/4" of the tip and cram it into the vial opening, the end will unfold and I can wipe it around inside... I also have 6" long cotton swabs that will do the trick.

    I DO realize that they are not all schiff bases but I didn't know what else to call them so I labeled them all "schiff base" anyway.

    AllInARow20001.jpg

    AllInARow10001.jpg

    RaspK0001.jpg

    MthylCedrylK0001.jpg

    MiddleFew0001.jpg

    LastOnes0001.jpg

    FirstSix0001.jpg

    C14andC180001.jpg
    Last edited by JEBeasley; 11th February 2014 at 07:10 AM. Reason: Clarity, format, grammar, blablabla
    Justin E. Beasley

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    Sounds like an excellent experiment JEBeasley! Awating with bated breath for the results...
    Paul Kiler
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    Most likely I'll:
    - swab out the condensation
    - dilute with only 95% alcohol (no dpg)
    - drop each onto a strip and mark the time to test for volatility/evaporation rates

    So, in essence I'll show how cloudy and soluble they are @ 10% dilution with 95% alcohol and demonstrate how long they last on a smelling strip. If anyone can think of any other info they'd like to know or think is important then let me know and I'll see what I can do.
    Justin E. Beasley

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    I have Indole too but it's diluted @ 50%, I purchased it from Creatingperfume. Does anyone know if it's advisable to use this? Should I use 2x the amount of indole since it's @ 50% dilution? I'm thinking I might try a few indole bases too while I'm at it.
    Justin E. Beasley

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    The deal with a Schiff Base is using a mole of Aldehyde and a mole of your Anthranilate, Methyl or Ethyl. That's what you are matching... and then your reaction takes place properly. If you use half strength of one, only half of your anthranilate will react with it, because there is only half the comparative weight to react with.

    That's the reason that I placed the Molecular weights on my Compendium, so that you know how much of each to use to reach maximum efficiency and reaction.
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    Quote Originally Posted by pkiler View Post
    The deal with a Schiff Base is using a mole of Aldehyde and a mole of your Anthranilate, Methyl or Ethyl. That's what you are matching... and then your reaction takes place properly. If you use half strength of one, only half of your anthranilate will react with it, because there is only half the comparative weight to react with.

    That's the reason that I placed the Molecular weights on my Compendium, so that you know how much of each to use to reach maximum efficiency and reaction.
    I have been using the molecular weights to determine amounts of each AC (from your compendium and from TGSC), I wasn't sure if the solvent used to dilute the indole would somehow interfere. Ok, I'll try a few indole experiments too. Is there any way to know which aldehydes or ketones will react with indole? If I cook these combos long enough they change color and release water but I have no idea if they are all truly reacting in ways that we are hoping for in order to form a base... Things like C14, C16, C18 and those ketones I'm feeling skeptical about. I have strawberry aldehyde on the burner now @ 80C for 30 min and it's changing color...


    EDIT: I completed the C-16, it turned a pale yellow-orange and like the others has more depth, seems sweeter with almost none of the characteristic intense, soapy, aldehydic notes. I don't know if it just discolored from heat or if it actually reacted, have no idea, interesting nonetheless.

    I also remade my C-11 base in order to dilute with ethyl alcohol only and compare with previous sample which I diluted with 40% DPG + 60% Ethyl Alc. - the previous sample is cloudy and having dilution problems.
    Last edited by JEBeasley; 11th February 2014 at 08:50 PM.
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    Maybe you could do a control experiment with just the indole, to check if it changes color under those cooking conditions.. Anyhow, wouldn't it be safer to work at lower temperatures for longer time?

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    Quote Originally Posted by Nizan View Post
    Maybe you could do a control experiment with just the indole, to check if it changes color under those cooking conditions.. Anyhow, wouldn't it be safer to work at lower temperatures for longer time?
    Safer? Probably but it's also possible that a higher temperature is required in order to induce certain reactions between chemicals... I don't know. I tried the ketones, C14, C16 & C18 at lower temps originally but I got no change as David indicated through his experience. I turned up the heat to see if it would make a difference and it did but I don't know what kind of difference. All of the others reacted around 50C-60C, I didn't turn up the heat until I noticed no reaction after 30min for those few that remained and then I turned up the heat every 30 min thereafter until I noticed a change.

    For the indole experiment I can do one with Hydroxy Citronellal and compare the result with the Indolene 50 I purchased from PA. This would give me a baseline from which to work and then I can try a few more from there.
    Last edited by JEBeasley; 11th February 2014 at 07:35 PM.
    Justin E. Beasley

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    So far, 10 minutes, into my Indolene 50 experiment: Indole 50% X2 + Hydroxycitronellal 100% X1 = Deep purple... My indolene 50 from PA is not deep purple, it's orange-brown, thick like honey and transparent. I will keep watching to see what happens, lol, maybe it will change color once it cools.

    EDIT:
    30 min @ 50C: Still purple, smells like Indolene 50, albeit closer to straight Indole, no other change, increasing heat to see if color changes to brown.

    + 30 min @ 70C: Darker purple (almost black), gaining a red-ish hue vs the blue-purple hue it originally had. Consistency is thicker, smell seems to be mellowing out a little. I'm wondering if my Indole was actually 50% or maybe more like 60-70% as the indole aspect seems to be overpowering the hydroxy citronellal
    Last edited by JEBeasley; 11th February 2014 at 09:01 PM.
    Justin E. Beasley

  40. #100

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    So far, 10 minutes, into my Indolene 50 experiment: Indole 50% X2 + Hydroxycitronellal 100% X1 = Deep purple... My indolene 50 from PA is not deep purple, it's orange-brown. I will keep watching to see what happens, lol, maybe it will change color once it cools.

    EDIT:
    30 min @ 50C: Still purple, smells like Indolene 50, albeit closer to straight Indole, no other change, increasing heat to see if color changes to brown.
    justin,

    i think you should be using Indole 50% X4 + Hydroxycitronellal 100% X1
    without getting into a chemistry discussion, indole has the nitrogen in the ring, rather than a double bond.
    so you need two molecules of the indole to bond with one molecule of the aldehyde.

    the ketones will take much longer to react, again because of their structure, use the same heat or lower, but give the reaction
    double or triple the time.

    also you can run these reactions anhydrous, calculate the weight of the water product, and
    add enough magnesium sulfate so it will take of that weight of the water, then filter out the MgSO4

    .

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    Quote Originally Posted by luigi_g View Post
    justin,

    i think you should be using Indole 50% X4 + Hydroxycitronellal 100% X1
    without getting into a chemistry discussion, indole has the nitrogen in the ring, rather than a double bond.
    so you need two molecules of the indole to bond with one molecule of the aldehyde.

    the ketones will take much longer to react, again because of their structure, use the same heat or lower, but give the reaction
    double or triple the time.

    also you can run these reactions anhydrous, calculate the weight of the water product, and
    add enough magnesium sulfate so it will take of that weight of the water, then filter out the MgSO4

    .
    Ok, thank you.
    I'm using the ratio 172.26 : 117.15 of Indole to Hydroxycitrolellal per Pauls compendium but my Indole is diluted @ 50% from Creating Perfume, the info page doesn't list which solvent is used. I can't imagine using more indole, it's already quite a bit more indole smelling than the pre-made Indolene 50 I have from PA - So, with that new info should I still be using 4x Indole?
    Justin E. Beasley

  42. #102

    Default Re: Schiff's bases

    well, it should be 2 moles of pure indole to 1 mole of the pure aldehyde, i believe, so as you mentioned if the indole
    is only 50%, then you would need 4x, but you are also weighing the solvent, to be accurate you need to determine the solvent weight

  43. #103
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    Quote Originally Posted by luigi_g View Post
    well, it should be 2 moles of pure indole to 1 mole of the pure aldehyde, i believe, so as you mentioned if the indole
    is only 50%, then you would need 4x, but you are also weighing the solvent, to be accurate you need to determine the solvent weight
    Yes, unfortunately I have no guarantee that my Indole 50% is actually 50%, it could be higher or lower and CP doesn't list the solvent they use, bleh.

    Is there any reason you can think of why my Indolene 50 is purple vs PA's Indolene 50 which is transparent orange-brown? Also, my Indolene 50 smells more of Indole with a mothball note, PA's Indolene 50 smells more like Hydroxy Citronellol with a light indole back note.
    Last edited by JEBeasley; 11th February 2014 at 09:48 PM.
    Justin E. Beasley

  44. #104

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    Yes, unfortunately I have no guarantee that my Indole 50% is actually 50%, it could be higher or lower and CP doesn't list the solvent they use, bleh. Is there any reason you can think of why my Indolene 50 is purple vs PA's Indolene 50 which is transparent orange-brown?
    no idea, other than a guess, kind of impossible to pin that down.
    Indolene 50 is however is a compound, rather than a pure molecule / schiff base
    so perhaps with the high heat and your time you ran the reaction further along and now have more of the schiff base
    which might explain the darker color....or as you mentioned the indole is not 50%

    can you do an test at 1:1

  45. #105
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    Quote Originally Posted by luigi_g View Post
    no idea, other than a guess, kind of impossible to pin that down.
    Indolene 50 is however is a compound, rather than a pure molecule / schiff base
    so perhaps with the high heat and your time you ran the reaction further along and now have more of the schiff base
    which might explain the darker color....or as you mentioned the indole is not 50%
    can you do an test at 1:1
    I will if I can do a 1:1 test of 50% Indole : 100% Hydroxycitronellal... or do you mean 50% Indole : 50% Hydroxycitronellal? By standard weight or molecular weight? I don't have any straight 100% Indole unfortunately.

    EDIT: I'm still heating it to see if anything changes. The color is now dark purple red, kind of looks like blood in color and consistency.
    Last edited by JEBeasley; 11th February 2014 at 10:06 PM.
    Justin E. Beasley

  46. #106

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    I will if I can do a 1:1 test of 50% Indole : 100% Hydroxycitronellal... or do you mean 50% Indole : 50% Hydroxycitronellal? By standard weight or molecular weight? I don't have any straight 100% Indole unfortunately.
    what i though was;
    Indole 50% X1 + Hydroxycitronellal 100% X1

    looking at indolene 50, it is only 50% of a schiff base and 50% indole
    so you made almost all schiff base... guessing, as you used 1 mole to 1 mole, that is why it is so dark

    so if you react 1 mole of 50% indole with 1 mole of the pure aldehyde, you should make
    50% of the schiff base....

    assuming your after indolene 50, rather than all schiff base

  47. #107
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    Quote Originally Posted by luigi_g View Post
    what i though was;
    Indole 50% X1 + Hydroxycitronellal 100% X1

    looking at indolene 50, it is only 50% of a schiff base and 50% indole
    so you made almost all schiff base... guessing, as you used 1 mole to 1 mole, that is why it is so dark

    so if you react 1 mole of 50% indole with 1 mole of the pure aldehyde, you should make
    50% of the schiff base....

    assuming your after indolene 50, rather than all schiff base
    Thank you for your help,
    That makes sense and explains why PA's Indolene 50 smells more like Hydroxycitronellol than Indole. So, what I have made then is more of a pure schiff base... It doesn't smell a whole lot different from straight indole but it does smell a little different and a little tiny bit softer. I imagine the indole will always dominate, it's a pretty strong material. With the indole being so dominant I'm not sure I see the advantage of making a bunch of indole bases unless it's something more like indolene where the other material is dominant. By itself the indole just smells like moth balls and I don't use it much for that reason, the indolene 50 to me is more manageable. So, if I end up making more indole bases then I'll probably double up on the other material so that I have more variation.
    Justin E. Beasley

  48. #108

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    Thank you for your help,
    That makes sense and explains why PA's Indolene 50 smells more like Hydroxycitronellol than Indole. So, what I have made then is more of a pure schiff base... It doesn't smell a whole lot different from straight indole but it does smell a little different and a little tiny bit softer. I imagine the indole will always dominate, it's a pretty strong material. With the indole being so dominant I'm not sure I see the advantage of making a bunch of indole bases unless it's something more like indolene where the other material is dominant. By itself the indole just smells like moth balls and I don't use it much for that reason, the indolene 50 to me is more manageable. So, if I end up making more indole bases then I'll probably double up on the other material so that I have more variation.
    sure thing, let me know how the Indole 50% X1 + Hydroxycitronellal 100% X1 turns out, if you run that.

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    Quote Originally Posted by luigi_g View Post
    sure thing, let me know how the Indole 50% X1 + Hydroxycitronellal 100% X1 turns out, if you run that.
    I'm running that one right now, I'll let you know how it goes.
    Justin E. Beasley

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    Default Re: Schiff's bases

    I don't know...
    It's dark purple, thin in consistency and smells like a more concentrated version of PA's Indolene 50 x2...
    PA's Indolene 50 is softer, thick like honey, more floral than indole and half the strength of what I just made.

    The indole still stands out as more prominent but not much more than PA's and the purple thing...? Once again, my Indole 50% could actually be a higher percentage than advertised but I don't know. Strange days, I have no idea what to think about any of this test.
    Justin E. Beasley

  51. #111

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    I don't know...
    It's dark purple, thin in consistency and smells like a more concentrated version of PA's Indolene 50 x2...
    PA's Indolene 50 is softer, thick like honey, more floral than indole and half the strength of what I just made.

    The indole still stands out as more prominent but not much more than PA's and the purple thing...? Once again, my Indole 50% could actually be a higher percentage than advertised but I don't know. Strange days, I have no idea what to think about any of this test.
    thinking you need to find some pure indole

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    Default Re: Schiff's bases

    Quote Originally Posted by luigi_g View Post
    thinking you need to find some pure indole
    I'll add it to my next order along with some interesting aldehydes and ketones.
    Justin E. Beasley

  53. #113

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    I'll add it to my next order along with some interesting aldehydes and ketones.
    so was doing some more digging, this is really interesting;

    TGSC lisitng for indolene 50:
    http://www.thegoodscentscompany.com/data/rw1377241.html

    CAS Number : 68908-82-7
    Molecular Weight : 289.41859000
    Formula : C18 H27 N O2

    but now i found this for the schiff base;
    hydroxycitronellal / indole schiff's base
    http://www.thegoodscentscompany.com/data/rw1377291.html
    CAS Number : 68527-79-7
    Molecular Weight : 271.40345000
    Formula : C18 H25 N O

    these are not the same material.......totally different structures, weights etc....

    also Vigon's spec sheet shows indolene 50 is diluted 50% with castor oil ???
    can that be possible?
    http://www.vigon.com/docs/spec/I-001351%20SPEC.pdf
    Last edited by luigi_g; 12th February 2014 at 01:06 AM.

  54. #114
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    Quote Originally Posted by luigi_g View Post
    so was doing some more digging, this is really interesting;

    TGSC lisitng for indolene 50:
    http://www.thegoodscentscompany.com/data/rw1377241.html

    CAS Number : 68908-82-7
    Molecular Weight : 289.41859000
    Formula : C18 H27 N O2

    but now i found this for the schiff base;
    hydroxycitronellal / indole schiff's base
    http://www.thegoodscentscompany.com/data/rw1377291.html
    CAS Number : 68527-79-7
    Molecular Weight : 271.40345000
    Formula : C18 H25 N O

    these are not the same material.......totally different structures, weights etc....

    also Vigon's spec sheet shows indolene 50 is diluted 50% with castor oil ???
    can that be possible?
    http://www.vigon.com/docs/spec/I-001351%20SPEC.pdf
    How strange, I can't imagine how castor oil would work in an alcoholic perfume blend. The consistency of the Indolene 50 from PA is that of castor oil and it's less intense than what I created, perhaps it's the same material.
    Justin E. Beasley

  55. #115

    Default Re: Schiff's bases

    Quote Originally Posted by JEBeasley View Post
    How strange, I can't imagine how castor oil would work in an alcoholic perfume blend. The consistency of the Indolene 50 from PA is that of castor oil and it's less intense than what I created, perhaps it's the same material.
    well if you had some castor oil, that would be an easy test, just dilute your product 50%,
    but then what would explain the huge color difference?
    during the reaction, did you ever notice an orange color ?

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    Quote Originally Posted by luigi_g View Post
    well if you had some castor oil, that would be an easy test, just dilute your product 50%,
    but then what would explain the huge color difference?
    during the reaction, did you ever notice an orange color ?
    No orange color however it did start to turn maroon-purple after the first one had been on the hot plate for over an hour. Perhaps if it was on the heat for longer it would have continued to red, orange or brown. I think I have some castor oil in the fridge, I'll see what happens tomorrow. I'll heat my sample again for a while and see what happens with the color.
    Justin E. Beasley

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    Default Re: Schiff's bases

    Quote Originally Posted by luigi_g View Post
    justin,

    i think you should be using Indole 50% X4 + Hydroxycitronellal 100% X1
    without getting into a chemistry discussion, indole has the nitrogen in the ring, rather than a double bond.
    so you need two molecules of the indole to bond with one molecule of the aldehyde.

    the ketones will take much longer to react, again because of their structure, use the same heat or lower, but give the reaction
    double or triple the time.

    also you can run these reactions anhydrous, calculate the weight of the water product, and
    add enough magnesium sulfate so it will take of that weight of the water, then filter out the MgSO4

    .
    How do you filter out Magnesium Sulphate (anhydrous I assume) from a reacted Schiff's Base that is as thick as treacle?

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    Default Re: Schiff's bases

    Many years ago when I too was playing with making Schiff's bases I tried to make Indolene. I used Molar proportions of pure, crystalline Indole and Hydroxycitronellal. I remember the mixture turing all sorts of colours from green to purple, and finally becoming brown. My product, whatever it was, was never as thick as commercial Indolene nor did it smell the same. When I GC'd Indolene 50 I found out that it was diluted in Hexyl Cinnamic Aldehyde. I don't know if this is still the case. I have no idea how Indolene is made commercially but I have a feeling that for the amateur it will be another of those "not really possibles".

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    Default Re: Schiff's bases

    Quote Originally Posted by luigi_g View Post
    so was doing some more digging, this is really interesting;

    TGSC lisitng for indolene 50:
    http://www.thegoodscentscompany.com/data/rw1377241.html

    CAS Number : 68908-82-7
    Molecular Weight : 289.41859000
    Formula : C18 H27 N O2

    but now i found this for the schiff base;
    hydroxycitronellal / indole schiff's base
    http://www.thegoodscentscompany.com/data/rw1377291.html
    CAS Number : 68527-79-7
    Molecular Weight : 271.40345000
    Formula : C18 H25 N O

    these are not the same material.......totally different structures, weights etc....

    also Vigon's spec sheet shows indolene 50 is diluted 50% with castor oil ???
    can that be possible?
    http://www.vigon.com/docs/spec/I-001351%20SPEC.pdf
    CAS 68908-82-7
    is known as Indolal
    CAS 68527-79-7
    is Indolene

    Indolal is often used as a non-discolouring Indole/Indolene replacement, but smell not much like either.

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    Default Re: Schiff's bases

    Quote Originally Posted by David Ruskin View Post
    Many years ago when I too was playing with making Schiff's bases I tried to make Indolene. I used Molar proportions of pure, crystalline Indole and Hydroxycitronellal. I remember the mixture turing all sorts of colours from green to purple, and finally becoming brown. My product, whatever it was, was never as thick as commercial Indolene nor did it smell the same. When I GC'd Indolene 50 I found out that it was diluted in Hexyl Cinnamic Aldehyde. I don't know if this is still the case. I have no idea how Indolene is made commercially but I have a feeling that for the amateur it will be another of those "not really possibles".
    It's good to know I was on the right track at least, I don't really want to chase my tail on this. Ultimately I'm hoping to make only those bases that are not easily purchased or available to the small perfumer. The Indolene 50 experiment was meant to act as a litmus test for the process of using Indole in base reactions, because I can compare the one I made with the commercial product.

    David, do you have any suggestions for interesting Indole bases that are worth making? Are all of the Indole bases going to be as complicated as Indolene 50? The indole note is so strong that it pretty much overpowers everything I combine it with, so much so to the point that I don't know how worth while it is to make Indole bases unless they are going to stand out as being somehow unique and more than just Indole smelling. Does Indole need to be on the burner for hours before it softens and for the other note to stand out? Does it eventually change to brown if it's on the burner long enough?
    Justin E. Beasley

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    Replies: 8
    Last Post: 28th February 2013, 06:52 AM
  2. Powdery bases
    By Javiero in forum Fragrance DIY
    Replies: 19
    Last Post: 6th September 2012, 08:59 PM
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    By princeOK in forum Fragrance DIY
    Replies: 20
    Last Post: 20th April 2012, 01:54 AM
  4. Perfume Bases/Carriers
    By PattiMcW in forum Fragrance DIY
    Replies: 4
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  5. Ten to Cover All the Bases
    By trumpet_guy in forum Male Fragrance Discussion
    Replies: 2
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