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  1. #31
    Super Member Finelikeanoyster's Avatar
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    Default Re: Making Schiff Bases

    Arctander (at PellWall descriptions) say MA also can reaction with acetophenone, musk ketone, ionones etc, not only aldehydes... Someone know what results from them ? (scent ?)
    If smell good I'm into this --certainly
    Currently wearing: Tai Winds by Avon

  2. #32

    Default Re: Making Schiff Bases

    Quote Originally Posted by Finelikeanoyster View Post
    Arctander (at PellWall descriptions) say MA also can reaction with acetophenone, musk ketone, ionones etc, not only aldehydes... Someone know what results from them ? (scent ?)
    You are right, theoretically you can make a Schiff base with any aldehyde or ketone, and many of the compunds are ketones.

    I had tried some of those you mentioned. With ketones (contrary to aldehydes) the reaction equilibrium is usually not on the Schiff base side, so you have to get rid of the water formed in the reaction. That's all doable, but when you make perfumes with a standard grade Ethanol, like 96%, that's probably where most of the 4% water will go and split the Schiff base back to it's starting materials. They reatain the smelling principle of Schiff bases, i.e. very close to a mix of the starting materials.

  3. #33
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    Default Re: Making Schiff Bases

    Thais very interesting to hear that a schiff base will attract the 4% water. what if one is using 100% pure ethanol? as far as i understood, 100% will stay 100% only with special storage, and will turn into 96% under 'normal' conditions. is that true? not a chemist here...

  4. #34

    Default Re: Making Schiff Bases

    Quote Originally Posted by pavomi View Post
    This very interesting to hear that a schiff base will attract the 4% water. what if one is using 100% pure ethanol? as far as i understood, 100% will stay 100% only with special storage, and will turn into 96% under 'normal' conditions. is that true? not a chemist here...
    Chemist here ...

    It's not that the water is "attracted", but it is just the least energy place for it to be. It get's there by chance, and stays there. Of course with the lack of water in 100% Ethanol (if there is no water from any other ingredient), the Schiff-base will not be able to decay.

    Oh well, if you leave 100% Ethanol open for a while, the humiditiy in the air will be absorbed to make it slowly 96%, that's correct (along with the Ethanol evaporating). But otherwise than air thight, no special storage is needed. The other problem is where to get 100% Ethanol from, and the third, how to make sure a confectioned perfume is not exposed to humid air. ... you can include a silica gel pack in every perfume, worth a try.

    Then again, there might be keto-Schiff-bases that are as stable as the aldo-Schiff-bases. Would be an interesting little project for a UV-VIS photospectrometer. ... or pkiler might have more extensive Keto-Schiff-base experience to share.

  5. #35
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    Default Re: Making Schiff Bases

    thanks for explaining! very much appreciated


    isnt there something like a 200 proof perfumers alcohol available? i remember reading that somewhere, but i might be wrong...

  6. #36
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    Default Re: Making Schiff Bases

    I've not really had good success with Ketone Schiff bases.
    I've failed with Musk Ketone, and I'm not really sure if my Acetophenone worked right either.
    I may have tried another too. And I have not tried to work with any ionones yet.
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  7. #37
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    Default Re: Making Schiff Bases

    Quote Originally Posted by Finelikeanoyster View Post
    How this smell PK ? beautiful crystals.
    All I had to use was a 50/50 Acetaldehyde alcoholic dilution, I drained the alcohol and water yesterday, as it was left after the reaction.
    I am letting these crystals dry out today, before evaluating, but I think I did get a whiff of orange blossom type of odor... Which wouldn't surprise me, as most MA Schiff bases go in that direction.
    Paul Kiler
    PK Perfumes
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    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  8. #38

    Default Re: Making Schiff Bases

    Wow! Almost mouth watering

  9. #39
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    Default Re: Making Schiff Bases

    Yes, Smells a lot like several other orangeblossom schiff base type materials.
    But given it's molecular size, it is likely still a middle, to upper base note.
    It also didn't like dissolving into alcohol.
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  10. #40

    Default Re: Making Schiff Bases

    Hi parfumistas, this thread inspired me so much, the patience and care Schiffs need is quite amazing. Thanks all!

    I just want to share that I did my first trial, MA+Lyral in a mini 5ml bottle, based on 1:1 - molecular mass of each. Then heated in moderate microwave setting (180w) for 30-40 seconds and got Aurantiol/Auralva like color and viscosity. The smell is indeed reminiscent of orange blossoms, but only just. It doesn't smell natural yet but the tone is there. But I'm wondering:

    - do I need keep heated (like on a radiator or under the sun) more to trigger reaction further ? if so what would be the suggested time for that process ?
    - i don't see any water forming, is that because of the little amount ?

    sorry if my questions do not make sense, as I said, my first go on Schiffs ever.

    Stay safe, stay cool.

  11. #41
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    Default Re: Making Schiff Bases

    Quote Originally Posted by emrego View Post
    Hi parfumistas, this thread inspired me so much, the patience and care Schiffs need is quite amazing. Thanks all!

    I just want to share that I did my first trial, MA+Lyral in a mini 5ml bottle, based on 1:1 - molecular mass of each. Then heated in moderate microwave setting (180w) for 30-40 seconds and got Aurantiol/Auralva like color and viscosity. The smell is indeed reminiscent of orange blossoms, but only just. It doesn't smell natural yet but the tone is there. But I'm wondering:

    - do I need keep heated (like on a radiator or under the sun) more to trigger reaction further ? if so what would be the suggested time for that process ?
    - i don't see any water forming, is that because of the little amount ?

    sorry if my questions do not make sense, as I said, my first go on Schiffs ever.

    Stay safe, stay cool.
    Emrego, I am sorry that I missed your question.
    Have you had any water come out of it by now?
    Often, I will keep a schiff base in a bottle about half filled, the bottle has a shoulder to the bottle's construction shape. I keep them outside in the sun for some time to let the water come off of it, and then daub out the water with a crooked tool wrapped in a paper napkin to absorb the water output... I just let the sun warm the capped bottle for several days until water stopped condensing on the bottle interior shoulder, then I know it is done, when there's no more water.
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  12. #42
    Super Member Ivor Joedy's Avatar
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    Default Re: Making Schiff Bases

    Quote Originally Posted by filousoph View Post
    ... The other problem is where to get 100% Ethanol from, and ...
    You can get 99.8% pure ethanol f.e. here (Art.-Nr.: 510)

    https://www.alkoholvertrieb-sued.de/produkte/

  13. #43
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    Default Re: Making Schiff Bases

    Ethanol will catch water from air quickly so such a high grade makes only sense if used immediately after opening.

    As for Schiff's bases, Dean-Stark trap setup and a suitable solvent should work very well. Cyclohexane and ethyl acetate seem to be fit for the task. In both cases keeping the reaction mixture at roughy 70oC should remove all the water nicely.

  14. #44

    Default Re: Making Schiff Bases

    Do you have any experience with Cinnamic aldehyde/MA Schiff base PKiler? I’m in the process of making one but I have never had such a dramatic color change before. It’s essentially black right now but is an iron red if enough light can pass through a small enough layer of it. It’s smells incredibly nice but just unsure with the color change if this is normal.

  15. #45
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    Default Re: Making Schiff Bases

    Quote Originally Posted by Levanthenon View Post
    Do you have any experience with Cinnamic aldehyde/MA Schiff base PKiler? I’m in the process of making one but I have never had such a dramatic color change before. It’s essentially black right now but is an iron red if enough light can pass through a small enough layer of it. It’s smells incredibly nice but just unsure with the color change if this is normal.
    Cinnamic aldehyde / MA schiff base is one of many that turn nearly black. :-)
    Some turn into white crystals. Many turn into strongly colored yellow and yellow thick molecules.
    Lots of chemical/molecular changes take place when a Schiff base is completed.
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  16. #46

    Default Re: Making Schiff Bases

    Quote Originally Posted by pkiler View Post
    Cinnamic aldehyde / MA schiff base is one of many that turn nearly black. :-)
    Some turn into white crystals. Many turn into strongly colored yellow and yellow thick molecules.
    Lots of chemical/molecular changes take place when a Schiff base is completed.
    If only they all made white crystals. Would be easy to handle and would also push the reaction forward to completion much faster!

    I appreciate your response and am relieved that this isn’t anything abnormal. Will be interesting to use and see how the color of the end product will be. This stuff is like black tar!

  17. #47
    Super Member Bkkorn's Avatar
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    Default Re: Making Schiff Bases

    Please excuse me of such a Noob question...

    But what is the goal to making a Schiffs Base? Like, is there a reason and need to make one and what is its purpose?

    I keep seeing in this thread all the neat colors and solids you all are making, but it makes me keep questioning.....

    why.jpg
    ...bathing in perfumes...

  18. #48

    Default Re: Making Schiff Bases

    Quote Originally Posted by Bkkorn View Post
    But what is the goal to making a Schiffs Base? Like, is there a reason and need to make one and what is its purpose?
    No doubt others here may have different perspectives.

    The schiff bases as used in perfumery are quite high molecular weight compounds, often thick pastes or very viscous liquids which are not particularly volatile. Using one as such can therefore lend longevity to certain notes of a fragrance (if this is what is desired). Also, though the presence of water will tend to favor the reverse reaction, using a schiffs base could potentially ensure more deposition of certain materials with low logP onto skin or fabric, especially in freshly manufactured consumer products such as shower gel or laundry detergent.

    Synthetically manufactured schiff bases have been mostly abandoned in commercial perfumery, but are still used in specific instances -- such as I mention above, or when discoloration is an issue, for example. Preparing them before hand, and adding them as is to the fragrance concentrate ensures no clouding will occur (because of water as a byproduct), and ensures the fragrance once diluted will not darken over time, which is a common problem with fragrances which are dyed (just visit sephora and look at old versus fresh bottles of commercial perfumes!).

  19. #49
    Super Member Bkkorn's Avatar
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    Default Re: Making Schiff Bases

    Quote Originally Posted by fragrantregard View Post
    No doubt others here may have different perspectives.

    The schiff bases as used in perfumery are quite high molecular weight compounds, often thick pastes or very viscous liquids which are not particularly volatile. Using one as such can therefore lend longevity to certain notes of a fragrance (if this is what is desired). Also, though the presence of water will tend to favor the reverse reaction, using a schiffs base could potentially ensure more deposition of certain materials with low logP onto skin or fabric, especially in freshly manufactured consumer products such as shower gel or laundry detergent.

    Synthetically manufactured schiff bases have been mostly abandoned in commercial perfumery, but are still used in specific instances -- such as I mention above, or when discoloration is an issue, for example. Preparing them before hand, and adding them as is to the fragrance concentrate ensures no clouding will occur (because of water as a byproduct), and ensures the fragrance once diluted will not darken over time, which is a common problem with fragrances which are dyed (just visit sephora and look at old versus fresh bottles of commercial perfumes!).
    thank you for that explanation, makes total sense now!
    ...bathing in perfumes...

  20. #50
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    Default Re: Making Schiff Bases

    Schiff bases accomplish a goal or need that no other molecule can.
    BKKORN, did you read my Perfumer & Flavorist interview yet? I answer your question also there...
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  21. #51
    Super Member Bkkorn's Avatar
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    Default Re: Making Schiff Bases

    Read it once, ...and about to read it again!

    https://www.perfumerflavorist.com/fr...568283141.html

    Side note, ...is the Schiffs Base concept how you came about with your 'Long Lasting Lemon" base at PSH?
    ...bathing in perfumes...

  22. #52
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    Default Re: Making Schiff Bases

    Quote Originally Posted by Bkkorn View Post
    Read it once, ...and about to read it again!

    https://www.perfumerflavorist.com/fr...568283141.html

    Side note, ...is the Schiffs Base concept how you came about with your 'Long Lasting Lemon" base at PSH?
    Yes, Schiff bases play the long hand in Long Lasting Lemon.
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  23. #53

    Default Re: Making Schiff Bases

    Quote Originally Posted by pkiler View Post
    Yes, Schiff bases play the long hand in Long Lasting Lemon.
    i'm guessing its possibly the product of a lemony aldehyde like citral reacted with a large anthranilate molecule like linalyl anthranilate to produce a molecule with weight over 400......just a guess

  24. #54
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    Default Re: Making Schiff Bases

    Long Lasting Lemon includes three schiff bases, including a schiff base made with an essential oil.
    Also includes another three more naturals, plus 15 other single molecules.
    The largest molecule used/made is more than 430 mw.
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    In addition to Our own PK line, we make Custom Bespoke Perfumes, perfumes for Entrepreneurs needing scents for perfumes or products, Custom Wedding Perfumes, and even Special Event Perfumes.

  25. #55

    Default Re: Making Schiff Bases

    This is how my Cinnamic Aldehyde/MA Schiff base turned out. It’s at less than 50% dilution, that’s a clear glass vial and it’s half full, I just shook it a bit. BDF93D69-A60D-416D-99E1-E78A21B47EC2.jpeg16FD6609-D785-48C8-8D6E-9C1CBECD0E69.jpeg

    I think this could pass as a new black pigment!

  26. #56
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    Default Re: Making Schiff Bases

    Quote Originally Posted by Levanthenon View Post
    This is how my Cinnamic Aldehyde/MA Schiff base turned out. It’s at less than 50% dilution, that’s a clear glass vial and it’s half full, I just shook it a bit.

    I think this could pass as a new black pigment!
    You could market your own scented pens with that... I'm sure you could write with it!
    Such as these...




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