Code of Conduct
Results 1 to 17 of 17
  1. #1
    Basenotes Plus
    pkiler's Avatar
    Join Date
    Dec 2007
    Location
    Southern California
    Posts
    8,693

    Default Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    What makes Ammonia? I have an Ammonia note appearing in the bottle headspace when opened after sitting all night. I formulated this trial #5 last night, made sure it was mixed, dipped a strip, and smelled that, until now, when I cracked the bottle to sniff the topnotes, only to find a strong ammonia bit in the perfume headspace.

    I am tempted to blame the butyrics / isovaleraldehyde in my dark chocolate accord, since I don't think I've ever used them before in a blend.

    In my Dark Chocolate accord:
    Isobutyraldehyde 1% 0.84%
    Butyric Acid 10% DPG 0.35%
    Isovaleraldehyde 10% 0.83%

    But I'm really not sure about this...

    There isn't the other side of a schiff base, for that to form, at least as far as I can tell.
    So, I wonder if one of these is combining with something to make Ammonia...???

    On a different train of thought,
    I *THINK* that Ammonia needs nitrogen to form. many perfume materials don't have nitrogen.
    But I am using a very small amount of tincture of prehistoric vegetal material, which given it's age, likely has nitrogen compounds in it.
    It's in my peat smoke accord, and if so, I'll have to remove that from that accord and try again.
    I have four previous failed trials on this perfume, and can whiff the ammonia in all of them... (Now that it is stronger, and I am looking for it, I can notice the ammonia, in nearly all of them.) BUT, the Peat smoke, and the dark chocolate appear in larger values in my fifth trial version, and the other objectionable pieces from previous trials have all been eliminated, so, now to track down this ammonia issue...

    Any thoughts?

    PK
    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.

  2. #2

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    "*THINK* that Ammonia needs nitrogen to form"
    "tincture of prehistoric vegetal material"
    Maybe some kind of bacteria metabolites?

  3. #3

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Paul, you're certainly correct that nitrogen is needed.

    So the source cannot be any of the named molecules.

    Why vegetable material in this situation might release ammonia is a total mystery to me! And additionally, few vegetable materials have much nitrogen (going along with the fact that they are not rich protein sources.) But as for an alternate possible theory that it's something else that isn't ammonia but smells like it, that's pretty mysterious too. Ammonia is such a distinct odor!

    Or is it? I don't know.

    I'm somewhat undecided on the distinction between odors and fumes. Personally I believe ethanol odorless but with fume effect. Mentally I characterize ammonia as a fume rather than an odor, although I expect most would say it's an odor. My unbaked thought is that some things "shock" the membranes of the nose without interacting with olfactory receptors and that is fume effect, but to quote Dr Evil, "I can't back that up."

  4. #4

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Quote Originally Posted by pkiler View Post
    What makes Ammonia? I have an Ammonia note appearing in the bottle headspace when opened after sitting all night. I formulated this trial #5 last night, made sure it was mixed, dipped a strip, and smelled that, until now, when I cracked the bottle to sniff the topnotes, only to find a strong ammonia bit in the perfume headspace.

    I am tempted to blame the butyrics / isovaleraldehyde in my dark chocolate accord, since I don't think I've ever used them before in a blend.

    In my Dark Chocolate accord:
    Isobutyraldehyde 1% 0.84%
    Butyric Acid 10% DPG 0.35%
    Isovaleraldehyde 10% 0.83%

    But I'm really not sure about this...

    There isn't the other side of a schiff base, for that to form, at least as far as I can tell.
    So, I wonder if one of these is combining with something to make Ammonia...???

    On a different train of thought,
    I *THINK* that Ammonia needs nitrogen to form. many perfume materials don't have nitrogen.
    But I am using a very small amount of tincture of prehistoric vegetal material, which given it's age, likely has nitrogen compounds in it.
    It's in my peat smoke accord, and if so, I'll have to remove that from that accord and try again.
    I have four previous failed trials on this perfume, and can whiff the ammonia in all of them... (Now that it is stronger, and I am looking for it, I can notice the ammonia, in nearly all of them.) BUT, the Peat smoke, and the dark chocolate appear in larger values in my fifth trial version, and the other objectionable pieces from previous trials have all been eliminated, so, now to track down this ammonia issue...

    Any thoughts?

    PK
    What is the PH of the perfume? Ammonia has quite a high ph. To be honest I can't fathom that it would form during the process.

  5. #5
    Basenotes Plus
    pkiler's Avatar
    Join Date
    Dec 2007
    Location
    Southern California
    Posts
    8,693

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Quote Originally Posted by George Tedder View Post
    What is the PH of the perfume? Ammonia has quite a high ph. To be honest I can't fathom that it would form during the process.
    Hmm, don't have a way to test this.
    But after reading more about my prehistoric vegetal material, I see that it is treated / processed after being gathered, with NaOH, and with Nitrogen present.
    NaOH is half of a reaction for Ammonia, right there, with Nitrogen residue.

    OK, well, I'm gonna bet on that being the issue, and I will reformulate my peat accord, which this is really too bad, because the prehistoric vegetal tincture is really rich in Humic acid, bringing the humus note. But, it was also kind of weak too, and has trouble competing with the aromachems. But it would have been cool to mention that this perfume has prehistoric materials in the peat accord. (No, I didn't tincture actual peat, BTW... I thought this other would be stronger, anyway.)
    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.

  6. #6
    Basenotes Junkie Dmitriy's Avatar
    Join Date
    Dec 2014
    Location
    Moscow
    Posts
    696

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Paul, Iím pretty sure that you are right and this isovaleraldehyde gives this ammoniac tinge of smell, perhaps along with something else. He has just hellish power! When I received a package with ingredients(wrapped in 15 layers of tape) in which there was one small sampler of this chemical, I could not understand the whole way to the house from where it smells like dirty socks..))))))) Now this sampler (small closed test tube) is stored inside a well-closed, tight plastic jar and the smell penetrates right through the plastic.

  7. #7
    Basenotes Plus
    pkiler's Avatar
    Join Date
    Dec 2007
    Location
    Southern California
    Posts
    8,693

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Hi Dimitry, I just did a calculation of the % of Isovaleraldehyde in the concentrate of the perfume, and got this percentage: 0.000055693%

    I do wonder if that is truly it, though... :-/
    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.

  8. #8
    Basenotes Junkie Dmitriy's Avatar
    Join Date
    Dec 2014
    Location
    Moscow
    Posts
    696

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Quote Originally Posted by pkiler View Post
    Hi Dimitry, I just did a calculation of the % of Isovaleraldehyde in the concentrate of the perfume, and got this percentage: 0.000055693%

    I do wonder if that is truly it, though... :-/
    Yes, Paul, that's quite a bit .. There of course it is possible that this aldehyde manifests itself in combination with some of the other ingredients of the mixture. Something can still push it forward. But I feel the smell of this material from the closed cabinet in which the sampler is located in two (one in the other) well closed containers as soon as I enter the room. I think it is necessary to look at him properly )))

  9. #9

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    coffee /tobacco accords pyridine sometimes - ammonia smell
    just noticed that clicking on the molecular weights you posted
    but yesterday I was thinking about fertilizer contaminant - vegetal - does overfertil7zing (ammonium phosphate) get up in the plant ?

  10. #10
    Basenotes Plus
    pkiler's Avatar
    Join Date
    Dec 2007
    Location
    Southern California
    Posts
    8,693

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    I wanted to post a follow up to this whole discovery process. This has been a vexing problem.
    I now have three ways to fix it.

    The Best solution is what will be solution three, but modified by either or both of the first two solutions.

    The best solution, of course is to eliminate that which is causing at least part of the reaction.
    But I tried others first, since I could not seem to find what I sought.

    First, I got the idea of trying chemically neutralize the Ammonia, by adding an opposite acid, to the base that is ammonia.
    I read around, and found that a weak acid would neutralize the weak base of ammonia.I tried some acetic acid.
    I am very familiar with Acetic acid, from my Photo Darkroom days, and have it in the Lab for use is scents, but have only employed it for it's odor, not for it chemical reactivity.
    I added acetic acid neat @ 1.5% to my scent concentrate, (nearly all of my materials are used at 100%, for those who do not know.)
    This improved the ammonia odor quite meaningfully, but not completely. I was worried about adding even more Acetic Acid to complete the neutralization, as high levels of Acetic Acid could be problematic, and I know I was already likely placing in too much.

    So I wrote Philip Kraft at Givaudan a note and asked for advice.
    He of course had a hard time diagnosing from a distance, with no formula, and nothing to smell but gave solid tips.
    His first tip was to change to Lactic Acid, instead of Acetic Acid, as Lactic is more skin friendly. Plus Philip said that Acetic acid was more reactive, and so could cause other problems. I added another 1.5% of Lactic acid on top of the Acetic, and it nearly took care of the problem completely. I was just a little worried that some amount may form later, so more investigation seems appropriate.
    Philip Kraft also recommended avoiding the whole addition of acids, by using Amberlyst 15 Ion Exchange Resin, which are small beads, and you pour your concentrate over them, through like a filtering mechanism, and they will react with the ammonia, and any amines, and remove them permanently, without adding any fluid acid to the concentrate. This sounded nice indeed, but simply buying them was rather problematic. In the next week, while I was trying to find an Amberlyst 15 supplier at an affordable price, (one supplier said they would sell me 250g for $750. eeek.) Finally, I found a supplier that sold me 500g for about $100, delivered by FedEx. (This still has to arrive, presently), So I have not yet employed this solution.


    I also went to another fine Perfumer friend with a lot of Chemistry background, Mike Storer. we had a long phone call, and this last batch, I noticed that when I added more of my Dark Chocolate accord, the amount of Ammonia went up, even after I had already taken out many other things that were suspected as the cause.
    We looked around in that Accord, which fortunately, I wrote and made up, and we found a pyrazine, 2,3-dimethyl Pyrazine, that has a Nitrogen atom in it. AHA!!!
    I remade the whole perfume again, leaving out the Dark Chocolate accord, subbing in the Milk Chocolate accord from PSH, (for which I know the formula), and added in some Isovaleraldehyde, and Cocoa Hexanal, for a new Dark Chocolate accord, and VOILA! the whole ammonia schtick was nearly completely absent. I also added back in some of the other previously removed items that were suspected...

    So, in the end, I will use the same dark chocolate accord from the last version, and may tune it up a bit, will put back in some of the other items previously suspected and removed, may not even have to use the Ion exchange resin, after all, and will likely place maybe 1% lactic acid in the concentrate to take care of any post bottling issues that may occur.

    That's my Report... But so far, the issue has been approached and solved with many different methods, and the best solution may indeed be a combination of all three.

    :-)

    PK
    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.

  11. #11

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Thank you, Paul. Great to know, and for me, I think it very likely that ion resin information may really be important for me in future work in another field.

  12. #12

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Quote Originally Posted by pkiler View Post
    We looked around in that Accord, which fortunately, I wrote and made up, and we found a pyrazine, 2,3-dimethyl Pyrazine, that has a Nitrogen atom in it. AHA!!!
    I'm not the most up to date on my chemistry, but looking at the molecular structure, that substance looks like it could be able to break down and release traces of ammonia.

    (For anyone with more biochemistry expertise who was curious: The issue is those two methyl groups, they make that side of the ring act like a ketone rather than aldehyde, and ammonia condensates with ketones are much more loosely bound than those with aldehydes. While the aromaticity of the ring adds stability, it could still be able to hydrolyze, possible slowly, either base or acid catalyzed, and that would leave butane-2,3-dione and the ammonia condensate of 2-aminoacetaldehyde, which will release ammonia before it further condenses)

    I believe this may be a very unusual situation. Fragrance compounds with nitrogen atoms in their structures do not normally release ammonia.

  13. #13
    New Member Finelikeanoyster's Avatar
    Join Date
    Sep 2019
    Location
    In a idyllic place
    Posts
    18

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    i've read, lactic acid are used in soaps, body creams and other products to ''soft'' the skin
    (a non agressive exfoliant), in lasts years researchs are tried to use lactic acid to hair straightening.
    Probably a bit of this cannot be bad, but particularly, I would not add this into a fragrance
    (I think you serched very good about).
    You could have tested in pairs the components of your formula to verificates the reactions, true ammonia is much volatile.
    I think too perfumed materials don't produce lot of ammonia...
    Last edited by Finelikeanoyster; 4th November 2019 at 01:32 PM. Reason: coherence

  14. #14

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    A couple of thoughts, Paul:

    In solution, ammonia is going to smell as NH3, but is (at any given moment) non-volatile as NH4+. Presence of an acid of course is going to tend strongly to have nearly all ammonia present as the NH4+ ammonium ion.

    A question is, how much acid.

    I don't know values in ethanol, but for example in water at neutral pH (which would require equimolar amounts of acid and ammonia) somewhat over 99% of ammonia is going to be in the non-volatile ammonium form. At pH 6, somewhat over 99.9%. At pH 5, somewhat over 99.99%, etc.

    The flip side of driving pH lower is that the breakdown rate of your ammonia-producer likely increases. (Not necessarily with exactly neutral pH as being the slowest breakdown rate. It would be necessary to analyze the mechanism and perhaps perform experimentation to determine pH with slowest breakdown rate: it's possible it's off from neutral somewhat.)

    It seems to me that returns from increasing the ionization percentage really, really diminish once reaching quite modestly acidic pH and may not be worth increasing the breakdown rate.

    Neutral pH of ethanol is slightly different than that of water, something like 7.3, but that's not a great deal of difference to take account for.

    As the amounts of ammonia-producer you have are very low, the needed amount of acid is very low. Anything past this, thus driving your pH substantially acidic, is probably counterproductive.

    Second thought, what difference does it make which acid it is? (Provided it doesn't itself smell bad, or is an irritant, etc.)

    Probably no difference in solution. The anion from the acid and the cationic ammonium will be dissociated from each other anyway.

    There are even some acids that are of some interest as perfuming actives but not usually used.

    Still further: you could use a buffer system to hold pH at some moderately acidic point such as 6.0 or 5.5, whatever you guessed to be the best compromise. That way, pH would not drift up significantly as ammonia was released.

    Last thought, after the alcohol evaporates (once on the skin) it may make no difference as the pH of the skin is already acidic.

  15. #15
    Basenotes Plus
    pkiler's Avatar
    Join Date
    Dec 2007
    Location
    Southern California
    Posts
    8,693

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Amberlyst 15, Ion Exchange Resin beads, dry, finally got here:
    https://www.youtube.com/watch?v=XRoKRxCH-Oc
    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. #16

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Quote Originally Posted by Bill Roberts View Post
    In solution, ammonia is going to smell as NH3, but is (at any given moment) non-volatile as NH4+. Presence of an acid of course is going to tend strongly to have nearly all ammonia present as the NH4+ ammonium ion.
    I don't really know all that much here, but I suspect if you were going to want to make the ammonia odor go away you would need a strong acid, not a weak acid (like vinegar or lactic acid, or anything else that might typically found in a perfume), at least not in small amounts. In short, it may likely just be impractical to try making the ammonia smell go away through the use of acid in the fragrance. (And I do not advise anyone adding a strong acid to a perfume)
    Ammonium acetate in solution still has quite a strong ammonia smell.

    This is probably a dead end.

  17. #17
    Basenotes Plus
    pkiler's Avatar
    Join Date
    Dec 2007
    Location
    Southern California
    Posts
    8,693

    Default Re: Hmmm, What makes Ammonia? I have an Ammonia note appearing in the bottle headspace.

    Quote Originally Posted by parker25mv View Post
    .
    Since Philip Kraft disagrees with you about the acid type, I'm gonna have to go with one of the chief chemists at Givaudan, giving me his thoughts and tips.
    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.




Similar Threads

  1. Ammonia smell?
    By Prince Geo in forum Male Fragrance Discussion
    Replies: 7
    Last Post: 12th May 2017, 06:13 AM
  2. Timbuktu - lavender? ammonia?
    By cbstarker in forum Male Fragrance Discussion
    Replies: 10
    Last Post: 19th June 2016, 04:38 PM
  3. Beware of wearing smokey smells to all who sweat an ammonia-like smell...
    By PungentPuncher in forum Male Fragrance Discussion
    Replies: 3
    Last Post: 24th October 2014, 12:48 AM
  4. Ugh, ammonia!
    By Xplo in forum Male Fragrance Discussion
    Replies: 2
    Last Post: 24th March 2006, 04:04 AM

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •  



Loving perfume on the Internet since 2000