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  1. #1

    Default Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    This is particularly vexing, I have had it diluted in Alcohol, at a higher percentage. Now I have lowered it down to 15% in alcohol, and a bit of DPG. I warmed it and FINALLY got it all dissolved. When cooled, it formed beautiful LONG crystals in the bottle. I just can't seem to get it to stay in solution...

    Any thoughts except even MORE dilution?


    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

  2. #2

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Just that the goodscents page lists it as soluble in water and alcohol, not DPG. You probably do know this already.

  3. #3

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Yes, TGSC lists alcohol, but it's just NOT going into that well...
    Another site lists DEP and DPG too.

    But Chris has mentioned Benzyl Benzoate.

    Mike Storer today when I talked to him on the phone suggested Benzyl Salicylate and Hedione.
    I am reticent to use BB, because that isn't going in the direction of my scent needs for this project, but Benz Sal and Hedione are.

    So I think I'll try that way tomorrow...

    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

  4. #4

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Sounds reasonable. Good luck.

  5. #5

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    This is one of the new materials we’ve just made available at Hermitage, so I had to deal with this recently.

    The stuff itself is much harder and drier than the TGSC entry would suggest - ours is manufactured by Synarome - not sure whether that's relevant or whether it's just down to lower UK temperatures (we are not having a hot summer so far . . .) Anyway it's like more like a lot of dusty rocks than anything remotely paste-like, with the lumps averaging 2-3” across.

    I really love the airy-orange blossom smell even as a solid though.

    I had no luck going direct to ethanol or with IPM, both of which work with heat but produced lovely crystal patterns on cooling.

    I actually have a 10% ethanol solution I've been trying to make cold that has been on the stirrer for over a week now & still has undissolved lumps in it: I’m fairly convinced the solution has saturated around the 7% mark.

    I used Benzyl benzoate for three reasons:
    *first the polarity is a reasonably good match (LogP values 3.9 vs 5.2-ish)
    *second the odour of benzyl benzoate is very low (and I was making for general sale rather than a particular fragrance)
    *third this base is itself chemically a benzoate.

    I considered Hedione but eliminated it because it isn't polar enough - LogP only 2.6 - I didn't try it to test though so it may well work. I didn't try the salicylate either because its odour is stronger, but as that has a higher LogP it's more likely to work.

    Having said which, IPM has a LogP value of above 7 and that was a failure so that clearly isn’t the only factor.

    I'll be very interested to know if you find something that works better than BB or BB and ethanol (for Hermitage I used 5% ethanol, 30% base and 65% benzyl benzoate in the end, although at cool UK temperatures that still goes solid, it's easy to melt and has a low enough flash-point for posting, which was also an important consideration for me that you may not need to worry about).
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  6. #6

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    So, I was completely stunned when the whole Kilo came yesterday from Vigon, and it sloshed around inside, and I looked inside and it was a yellow clear liquid.

    I assumed that the warm UPS truck helped it liquefy, but it had all night to cool on my desk inside the house, and it's still a liquid, and I can't see any crystals growing this AM.

    Smells great too!

    Hopefully this will be the end of the saga... but time will tell..

    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

  7. #7

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    PK, be careful using this oil as though it will now dissolve.

    Crystallisation of the oil you recieved will occur over time and it will even be faster when you are trying to dissolve it above the solubility level. Quite often larger batches are during the production process dissolved in a "strong" solvent unsuitable for perfumery, like dichloromethane or something. When this solvent is completely removed, it is quite common to end up with a metastable oil, as we call it. The oil state can last quite long, depending on the trace amount of residual solvent, the presence of minor impurities, and the viscosity of the oil.

    Add one pure crystal of the shiff base to the oil you recieved and the whole thing should start to solidify slowly (nucleation), unless there is some of the strong solvent left,or if there are too many impurities. This would be a sign of poor product quality...

  8. #8
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    After moving, getting settled and partially setting up my lab again I was finally able to dilute my home-made Helional/MA Schiffs Base sample today. I'm having solubility issues too but not quite as bad as what you guys are dealing with. Perhaps I didn't make mine properly, I don't know... The base was a semi-crystaline paste in the bottom of the bottle, I added 40% DPG and 60% Ethyl alcohol in a 10% mixture. Hours later it appears as though half of the base has dissolved but the other half swims around in solution as transparent yellow globules and strands like a lava lamp. If I shake the mixture vigorously the globules break into tiny bubbles that eventually glom together at the bottom of the bottle. I'll give it a few days to see if it goes anywhere and report back.

    I had major solubility issues with a couple of the other base experiments (C-11 and Cinnamic Aldehyde) but I chalked it up to them having been cooked too long because they ended up being really dark, thick and phenolic smelling. I assumed they were bad because their odor profile had been altered to the point of having less longevity and lower strength than their original counterparts, not to mention being insoluble in alcohol.
    Justin E. Beasley

  9. #9

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    How did you make this home-made Schiff base? How did you purify it?

    If you dont mind me asking, what is your chemical education? Im happy to help but you shouldnt mess with these things unless you know what you are doing...

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  10. #10
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    Smile Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Quote Originally Posted by thomash View Post
    How did you make this home-made Schiff base? How did you purify it?

    If you dont mind me asking, what is your chemical education? Im happy to help but you shouldnt mess with these things unless you know what you are doing...

    Verstuurd van mijn GT-S5830i met Tapatalk
    I ALWAYS mess with things when I don't know what I'm doing, that's how I learn. I don't have any chemical education whatsoever, thanks for the offer nonetheless. Purify? I didn't know I had to "purify" it. What sorts of impurities are present? Do you mean remove the water from them? Dehydrate? Desiccate? I do have and have used desiccants and molecular sieves. I'm working at micro scale, most of the water just evaporates from my bottles. I just put two aroma chemicals together according to their molecular weights and cooked them at 150-170 deg C until water stopped condensing. I swabbed the remaining water out of my bottles and there they are.
    Last edited by JEBeasley; 11th July 2014 at 05:18 PM.
    Justin E. Beasley

  11. #11

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    OK, this sounds a bit more rude than it was intended, but here it goes:

    When you heat something to 170 deg C, you will ALWAYS have some form op product degradation going on. I'm assuming you aren't using an inert atmosphere to do this, so oxidation is the first thing that comes to mind. MA will form small amounts of nitro, and nitrosocompounds. these are most likely toxic, especially the nitroso compounds. The aldehydes you are using are even more so oxidation sensitive and will be forming carboxylic acids. Some of them harmless, some of them irritating. Have you checked the boiling/sublimation points of the materials? You're probably boiling off the aldehyde instead of water. Have you checked the flash point of the aldehyde? You are probably risking a serious fire if you have some perfumers alcohol near this setup..

    The need for dehydrating agents depends on the aldehyde you're using, so I can't really answer that without having the details.

    This is why I say you shouldn't mess with it. You have no chemical background and have no clue what could go wrong. You're using some random procedure which is clearly not ideal. It's not because google tells you to do something that you should listen. Putting this stuff on your skin (or that of others god forbid) is playing with your/their health.

    There is not a single aromachemical on the market which was not purified by its manufacturer. They wouldn't risk it. In your case, simple recrystallisation may do if you adjust your procedure to use more mild conditions.

    I'm sorry if I sound a bit harsh, but it takes years of education to be able to succesfully synthesize one aromachemical from another. (OK, for a Schiff base maybe just months, but still...)

  12. #12
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Sorry, I was going from memory of what I did several months ago. I misspoke with regard to the temps I actually heated them 50-70C not 150-170... I don't have alcohol anywhere near my setup, I'm not THAT incompetent, I do have some experience with solvents and volatiles from having been a cabinet finisher. I did not check the boiling points, next time I will do that. I did have adequate ventilation, did I mention I used to use toxic chemicals as a cabinet finisher... (three part epoxy polyesters, catalyzed urethanes, lacquers, etc) I don't do anything because google tells me to. Harsh? I don't care about harsh or have time to be bothered by it, keep on harshing brother. Thanks for the info, I'll take it into consideration next time.

    This was the original thread where I began my experiments. I had a long and labor intensive move to another city in addition to a few other hurdles but I'm getting set up and ready to start work again.

    http://www.basenotes.net/threads/374683-Schiff-s-bases

    So are you saying that all of the aldehyde schiffs bases must be purified of "poisons" prior to use?
    Last edited by JEBeasley; 11th July 2014 at 09:12 PM.
    Justin E. Beasley

  13. #13

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Oh, Now I feel rather foolish...

    I've been asking about the MA/Helional Base, and Ordered it and it came, and I said it was a liquid. Well, *IT* was a liquid, but it wasn't MA/Helional. It *IS* MA/Triplal

    I'm sorry for causing confusion to others that was my fault.

    PSH will have a large chunk of it for sale soon.

    So Sorry for adding unnecessary confusion...

    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

  14. #14
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Pretty funny, I still have little globules in my helional base... they are possibly water or perhaps some of the "impurities" thomash spoke of, I might try a dessicant and see if it gets pulled out. I didn't have any solubility issues with triplal, it went right into solution and mine was liquid too, lol.
    Justin E. Beasley

  15. #15

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    I've got the same issue with the MA/Helional. I just checked and the MA/Triplal is still in solution. The helional has me irritated at the moment. I visited a friends lab today and he offered me a stirring unit that has heat. Im stoked about that.

  16. #16
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Quote Originally Posted by jmcdowell View Post
    I've got the same issue with the MA/Helional. I just checked and the MA/Triplal is still in solution. The helional has me irritated at the moment. I visited a friends lab today and he offered me a stirring unit that has heat. Im stoked about that.
    I have a heated stirring plate but my sample is at micro scale so I can't really stir it anyway. jmcdowel, is yours crystalized like Pauls or do you have the same swirling liquid strands and globules that I have?
    Justin E. Beasley

  17. #17

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    20140712_083933.jpg


    Hard to describe, sort of fluffy crystals. I tried to post a photo. Hopefully you can see it.

    Edited to say: This is at 10% btw.

  18. #18
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Interesting... My sample must be dead wrong then. Perhaps I didn't heat it long enough because mine didn't crystalize to that extent and when diluted seemed to mostly dissolve into solution. What methods did you use to create yours? I combined Helional and MA in equal amounts according to their molecular weights and heated this combination @ 60C for 30 min or so... Next time I'll take into consideration their boiling points as thomash suggested.
    Justin E. Beasley

  19. #19

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Quote Originally Posted by JEBeasley View Post
    Interesting... My sample must be dead wrong then. Perhaps I didn't heat it long enough because mine didn't crystalize to that extent and when diluted seemed to mostly dissolve into solution. What methods did you use to create yours? I combined Helional and MA in equal amounts according to their molecular weights and heated this combination @ 60C for 30 min or so... Next time I'll take into consideration their boiling points as thomash suggested.
    It's because you know damn all about Organic Chemistry, and ignore the advice given to you by those who do know.

  20. #20

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    I didn't make it myself. I would end up with purple hair or blowing a hole in my building or something like that.

    I dont have any experience with other solvents but I suppose I better start practicing.
    Does anyone have a suggestion for this particular beauty?

  21. #21
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    David, you are right that I know damn all about chemistry but I don't understand you saying that I have ignored anything... I've never intentionally passed myself off as a chemist or one who is knowledgeable in the science of chemistry. Actually, I have ignored nothing and take all advice given to me very well. I actually feel a bit hurt by that comment sir. If you can point out an example where I have ignored you or any of the knowledgable members of basenotes I would appreciate knowing it because right now I'm not recalling a moment.
    Last edited by JEBeasley; 12th July 2014 at 11:45 PM.
    Justin E. Beasley

  22. #22

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    I seem to recall that in the previous thread about Schiff's bases when ever I made a comment I was ignored. If this is not true, I apologise.

  23. #23
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Quote Originally Posted by David Ruskin View Post
    I seem to recall that in the previous thread about Schiff's bases when ever I made a comment I was ignored. If this is not true, I apologise.
    You were not ignored by me David, I have only ever held your knowledge in high esteem when it comes to perfumery. I seem to remember you having words with another person in the thread but it wasn't me. I took whatever small nuggets of info I was given, by whomever was willing to give them and ran with it as hard, fast and long as I could until I had to stop in order to pack up my lab and move to another city. While I can be abrasive, cavalier and reckless I am never intentionally disrespectful or dismissive to someone who extends their time and effort to share their knowledge, insight and experience.


    Anyway, if the helional schiffs base can't be diluted in a conventional or simple way then I'll happily do without, I have plenty of other materials to work with.
    Justin E. Beasley

  24. #24

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    This is a good example of the kind of thing that makes perfuming difficult. You can't just get ingredients and mix them. You have to struggle with solubility problems, and with things not being as they are supposed to be.

    To me, If I can get something to where 10-15 seconds in the microwave will liquify it for a while, I feel I'm not doing too badly.

    I wish you could just put everything in DPG at 10% and not worry about it, or that it came already dissolved in a liquid form. If it's ambegris, you have a solid year of work ahead of you before you can even use it. You might have 100 ingredients in your perfume, and therefore 100 sets of problems to solve.

    This is why I admire anyone who can make perfume. There are countless issues other than the creative part.

  25. #25

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    OK, to make a Schiff base:

    1. start with an aromatic aldehyde (aromatic in the chemical sense, not the olfactory sense) e.g. benzaldehyde, salicaldehyde etc but not C8, C9, etc.
    2. add to it an equal (molar) amount of aromatic amine (again in the chemical sense of the word, an aniline such as mehtylanthranilate)
    3. within the next minute, add a very small amount of the highest grade alcohol you can get (95+%). How much dépends on the scale. For a gram of each starting material, about 20 drops should do.
    4. mix well
    5. wait for the mixture to solidify, don't heat it. This could take between a few minutes and a few hours, hard to predict.
    6. the solid needs to be filtered (this can be hard if you dont have a pump, as the liquid is stuck between the solids, dabbing it with absorbant paper may work as well.)
    7. recrystallise the solid. This involves heating it with approximately equal amounts of ethanol untill all of it dissolves. If the ethanol boils and not all of the solid is dissolved you need to add more ethanol. Once everything is dissolved, let it cool slowly. The Schiff base will come out of solution again, in pure form.
    8. filter
    9. let it dry
    10. finished

    DO NOT USE OPEN FLAMES DURING THIS PROCEDURE

    Note that this will not work for aliphatic amines or aldehydes.

  26. #26
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Thank you Thomash
    Justin E. Beasley

  27. #27

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    No prob. Let me know how it works out for you.

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  28. #28
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    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    Quote Originally Posted by thomash View Post
    No prob. Let me know how it works out for you.

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    I will. I probably won't get around to it for a while though as I have to purchase a pump and funnel for filtering but I will report back once I have had a chance to mess around with it.
    Justin E. Beasley

  29. #29

    Default Re: Need Help with Solubility for Helional/Methyl Anthranilate Schiff Base

    So, I *finally* got the Kilo in today, Of the *RIGHT* MA/ Helional base, instead of what I THOUGHT was this base...

    UGH! Stupid Paul...

    And it is a yellow dry playdoh type of consistency. Fortunately in a plastic bottle, with a wider mouth than an aluminum Kilo Can.

    So if I get into trouble getting it OUT of the bottle, I can cut it open and retrieve the contents...

    Now I have to figure out to make it liquid and stay there... for some applications. For others, I can simply blend it in as a solid and wait for it to dissolve in the other materials.

    PK
    Paul Kiler
    PK Perfumes
    http://www.PKPERFUMES.com
    Gold Medal for "Best Aroma"; Los Angeles Artisan Fragrance Salon

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