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Thread: Schiff's Base Q

  1. #1

    Default Schiff's Base Q

    So I am attempting making some Schiff's Bases, the only potential issue is that I am using 50% Methyl Anthranilate, I couldn't find 100%. Is there any issue this will cause other than potentially slowing the reaction down?

    How long does the average complete reaction take?

  2. #2
    Super Member benjwi02's Avatar
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    Default Re: Schiff's Base Q

    Quote Originally Posted by chyprefresh View Post
    So I am attempting making some Schiff's Bases, the only potential issue is that I am using 50% Methyl Anthranilate, I couldn't find 100%. Is there any issue this will cause other than potentially slowing the reaction down?

    How long does the average complete reaction take?
    It may have an impact. Schiffs base is a reversible reaction, so I believe that if ethanol is your dilutent, ethanol might back react with the product since water (a very close molecule structurally to ethanol) is produced as a product.

    I would say itís best to run schiffs base reactions with pure reactants. This is from some experience doing Schiff base research at university as well as when I was working with Paul.


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    Super Member benjwi02's Avatar
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    Default Re: Schiff's Base Q

    Quote Originally Posted by benjwi02 View Post
    It may have an impact. Schiffs base is a reversible reaction, so I believe that if ethanol is your dilutent, ethanol might back react with the product since water (a very close molecule structurally to ethanol) is produced as a product.

    I would say itís best to run schiffs base reactions with pure reactants. This is from some experience doing Schiff base research at university as well as when I was working with Paul.


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    I havenít confirmed if the back reacting occurs with the ethanol, so I donít know if it happens. With organic chemical syntheses, unless you know that there is no potential of an unwanted reaction, itís best to run them pure.


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  4. #4

    Default Re: Schiff's Base Q

    It's 50% in Benzyl Benzoate, I made the mixes anyways, we'll see what happens.

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    Default Re: Schiff's Base Q

    MA schiff base reactions can be relatively fast, in days, but the purification may take time. I must confess, I have never run schiff base construction with any diluted material. That just reduces all issues. I am sorry that MA is somewhat restricted for sale, unless prediluted. It's a bit painful for me see all of you that must buy diluted only....

    I can suggest though, to regularly agitate the solution to bring pertinent molecules together for reaction.
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  6. #6

    Default Re: Schiff's Base Q

    Okay well I did the 1:1 by mol weight, factoring in the 50% dilution. Then I put them in beakers for half an hour (a little below water's boiling temp), the Ald-C10 + MA was foggy yellow but under heat it became clear golden yellow, and back to foggy yellow once it cooled down. The Citral + MA base changed very little if at all under my observation staying a clear golden yellow, I'm sure some reactions occurred but am clueless how much more reactivity is required if at all or to just let it sit for days with occasional swirling. I am unsure how either are supposed to look upon completion.

    I am mostly interested in the Citral + MA base as I've heard it's the best Schiff's Base by a few people on here and being a huge citrus/neroli fan myself would love to have it in my toolkit.

    Note: The Citral I used during heating was the clear (natural) variety. There's another mixture I made with synthetic Citral which is a thick yellow, that Schiff's base is a light brick red/orange color and I never heated it. I wonder if only the synthetic Citral reacts properly with MA?

  7. #7
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    Default Re: Schiff's Base Q

    Citral in essential oils make a schiff base just fine.
    Completed undiluted synthetic Citral / MA schiff base looks like the photo below.
    Attached Images Attached Images
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  8. #8

    Default Re: Schiff's Base Q

    Quote Originally Posted by pkiler View Post
    Citral in essential oils make a schiff base just fine.
    Completed undiluted synthetic Citral / MA schiff base looks like the photo below.
    Thanks for the pic Paul, so there's a chance the natural Citral isn't reacting, I wonder why? Less color would be a bonus.

    You think I should heat the Synthetic Citral + MA even though I already see a reaction occurring?

    I'll do it anyways just to see if it changes.

  9. #9

    Default Re: Schiff's Base Q

    Does citral-MA schiff base smell strongly lemony?

  10. #10

    Default Re: Schiff's Base Q

    I think so, I believe it extends the Citral out into a base note, at least I think it does. Paul or someone else can enlighten us.

    Edit: Okay so I heated up synthetic Citral + MA thoroughly and after about 10 minutes in boiling water the color changed from orange/red to a darker brown/red, obviously not as opaque as Pauls due to the 50% MA but quite close. I reheated the other Natural Citral + MA mix again at even higher temps and there is still no change in color, it also smells somewhat more lemony than the synthetic Citral.
    Last edited by chyprefresh; 23rd June 2021 at 08:18 AM.

  11. #11
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    Default Re: Schiff's Base Q

    I’m just gonna throw this out there, there is a seller on ebay called “himedia” they have is undiluted, though I’ve never bought it so I have no idea the quality, but they are based out of the US (Well ships from, who knows if it’s made here)if that means anything.

  12. #12

    Default Re: Schiff's Base Q

    Quote Originally Posted by Casper_grassy View Post
    I’m just gonna throw this out there, there is a seller on ebay called “himedia” they have is undiluted, though I’ve never bought it so I have no idea the quality, but they are based out of the US (Well ships from, who knows if it’s made here)if that means anything.
    Thanks for the suggestion, for now I'm going to try and see if get 50% MA works so it's more convenient and so more people can do this, and so far I'm getting results. Perhaps heating the mixture and constantly moving it around while heating it makes needing 100% MA unnecessary. I left the lid off my shorter vial and it evaporated away the (water from the reaction I believe), it's no longer cloudy (c10+MA). The longer test tubes trap the evaporating water I think.

    I'm going to do the same for Triplal + MA tomorrow.

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    Default Re: Schiff's Base Q

    Quote Originally Posted by chyprefresh View Post
    Thanks for the suggestion, for now I'm going to try and see if get 50% MA works so it's more convenient and so more people can do this, and so far I'm getting results. Perhaps heating the mixture and constantly moving it around while heating it makes needing 100% MA unnecessary. I left the lid off my shorter vial and it evaporated away the (water from the reaction I believe), it's no longer cloudy (c10+MA). The longer test tubes trap the evaporating water I think.

    I'm going to do the same for Triplal + MA tomorrow.
    Oh not bad, try it out

    Your MA is in ethanol?

    Actually now that I think about it, I’m pretty sure reactions can occur in a whole formula so I doubt whatever it’s diluted in will cause major issues

  14. #14

    Default Re: Schiff's Base Q

    Quote Originally Posted by Casper_grassy View Post
    Oh not bad, try it out

    Your MA is in ethanol?

    Actually now that I think about it, I’m pretty sure reactions can occur in a whole formula so I doubt whatever it’s diluted in will cause major issues
    No it's in BB I'm not sure what's causing the cloudiness in the mixture but I think it might be water. Unfortunately the cloudiness returned somewhat but it's partially clear.

  15. #15

    Default Re: Schiff's Base Q

    Water and benzyl benzoate are immiscible, as are your reactants and water.

    Paul has some good posts related to this.

    The water will of course disappear on addition of ethanol later.

    Driving it off now would aid at least somewhat in completion of the reaction.

    The reason I say at least somewhat is that only the water actually in solution in the mixture is available for the reverse reaction. Water that exists in a separate phase, whether in bulk or tiny suspended droplets, is not available anyway,

    I don't recall the solubility of water in BB but it is low.

  16. #16

    Default Re: Schiff's Base Q

    I normally like to make these things myself but since small perfumers can’t buy MA at full strength, I just buy it premade from Creating Perfume.

  17. #17

    Default Re: Schiff's Base Q

    As you are talking about schiff's bases, anyone has Helianthral pur? also called ocean propanal, helional / methyl anthranilate schiff's base.
    I received it few days ago. It's hard as a rock. I have not tried to dissolve it yet, but I am afraid it will be difficult.
    Any suggestions?

  18. #18

    Default Re: Schiff's Base Q

    PCW sells MA with and without BHT. It does not seem to be prediluted.
    I didn't purchase that, so look yourself.

    Also De Hekserij , Holland, sells MA pure, undiluted. And it's very cheap.

  19. #19
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    Default Re: Schiff's Base Q

    I find this thread and subject absolutely fascinating. Please do post some pics of your progress on some of these shifts bases you are experimenting with, I love watching them change color in stages
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  20. #20

    Default Re: Schiff's Base Q

    may i ask whats the point about methyl Antranilate sold just in dilution? never heard about that before.
    here in Europe it is readily available pure.

  21. #21

    Default Re: Schiff's Base Q

    I will go check but I think it has to do with potential use as an illicit drug precursor -- as if these steps are accomplishing anything much it at all to reduce the problem.

    Yes, in the US anthranilic acid and its esters are List 1 substances, due apparently to being useful for making methaqualone (Quaalude.) Exactly what that results in I can't say but generally one has difficulty finding any of these items in pure form at retail.

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    Default Re: Schiff's Base Q

    Quote Originally Posted by mnitabach View Post
    Does citral-MA schiff base smell strongly lemony?
    Yes, Mike...
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    Default Re: Schiff's Base Q

    Regarding clouding at cool temperatures - This means that there is still water in the product, waiting to be removed (for a liquid end product). Schiff bases either clear up with water removal, or they become a solid, (if they do not clear, and the water is removed).
    They will almost always be clear with elevated temperature.
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    Default Re: Schiff's Base Q

    Quote Originally Posted by Sniffita View Post
    As you are talking about schiff's bases, anyone has Helianthral pur? also called ocean propanal, helional / methyl anthranilate schiff's base.
    I received it few days ago. It's hard as a rock. I have not tried to dissolve it yet, but I am afraid it will be difficult.
    Any suggestions?
    Yes, Helional / MA schiff is a solid.
    Will dissolve readily into alcohol, or you can pulverize it with a hammer for smaller chunks, too. Both are useful. The powdered/small chunks do also go into solution when added to 100% materials concentrate, too, may take just a bit of stirring, or an overnight session to dissolve by next day.
    MA -Helional Schiff base.jpg
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  25. #25

    Default Re: Schiff's Base Q

    [QUOTE=pkiler;5202993]Yes, Helional / MA schiff is a solid.
    Will dissolve readily into alcohol, or you can pulverize it with a hammer for smaller chunks, too. Both are useful. The powdered/small chunks do also go into solution when added to 100% materials concentrate, too, may take just a bit of stirring, or an overnight session to dissolve by next day.

    Thanks a lot. Very kind of you.
    Last edited by Sniffita; 24th June 2021 at 10:29 AM.

  26. #26

    Default Re: Schiff's Base Q

    Quote Originally Posted by chyprefresh View Post
    So I am attempting making some Schiff's Bases, the only potential issue is that I am using 50% Methyl Anthranilate, I couldn't find 100%. Is there any issue this will cause other than potentially slowing the reaction down?

    How long does the average complete reaction take?
    I really do not think it will be an issue. It might temporarily cause some side reaction, but eventually (after time) it will go in the direction you want it to go in.

    Alcohol is not an unusual solvent for preparing Schiff bases.

    Quote Originally Posted by chyprefresh View Post
    How long does the average complete reaction take?
    I really cannot give you an exact answer to that, but the majority of it (90%) should react in the desired way within a few minutes of vigorous stirring, if everything is dissolved.
    How long it will take for the entirety of it to react is a more difficult question. It could take 2 weeks. (very rough inexact answer)

    What might be helpful to understand is that nothing in this reaction is entirely 100% irreversible. It is just mostly irreversible, tending to go in one direction.

    When the alcohol mixes with the aldehyde, it transiently can form something known as a hemiacetal. This mostly just exists in the solution. It probably does contribute some unique smell of its own, but I would expect that smell would probably be far weaker than the desired Schiff base. The hemiacetal will pretty much behave chemically the same as aldehyde that happens to be dissolved in alcohol. That is, it can behave like a plain aldehyde.

    Why is this the case? Well that takes a little bit more of a complicated explanation. There will always be a small equilibrium, a very small fraction of the hemiacetal will always exist in the form of a free aldehyde at any given instant in time. As soon as this aldehyde reacts, more aldehyde will then become available.
    There also exists an equilibrium with the Schiff base but it is much smaller. (This is especially true since the total fragrance will likely contain so little water). The smell is essentially almost going to be entirely from the Schiff base, not the separate components of it by themselves.

  27. #27

    Default Re: Schiff's Base Q

    Okay guys, some changes have happened! The Triplal/MA base cloudiness is gone after heating it once again. The natural (clear Citral)/MA base has gone from the exact same (green yellow) color as MA to now a golden yellow, compared to the synthetic Citral/MA base which is a dark red/brown. Incredible how the same molecule can look so different in a Schiff's based on how it is derived.

    My next update will be on seeing if any further changes occur. And after that, which ones are performing like they should.

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    Default Re: Schiff's Base Q

    Good night.
    I would like to know how to make a schift base, which weight percentages of Methyl Anthranilate and Hydroxycitronellal and Methyl Anthranilate and Citral.
    Thank you very much
    Best regards

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    Default Re: Schiff's Base Q

    Quote Originally Posted by Saraiva View Post
    Good night.
    I would like to know how to make a schift base, which weight percentages of Methyl Anthranilate and Hydroxycitronellal and Methyl Anthranilate and Citral.
    Thank you very much
    Best regards

    How much to use is always based on the molecular weight of each material. Methyl Anthranilate is mw of 151, So I make with 1.51g pure MA, or, multiples, like 3.02g

    Find the mw of any other material that you want to work with, and do the same.
    Except for Indole and Skatole.

    In the case of Skatole and Indole, you need to add 2mw of these to 1mw of aldehyde or ketone.

    Here are two slides from my Schiff Bases Workshop deck. I'll be opening this class up as soon as COVID is gone... It's a perfect weekend workshop, in person.

    Schiff slide 1.jpg
    Last edited by pkiler; 26th June 2021 at 02:52 PM.
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  30. #30
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    Default Re: Schiff's Base Q

    Paul Kiler
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