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Re: Ethyl-Acetate (wrongly demonized ?)

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  • Mike Gasmier
    Here s a little experiment from my old high school chemistry textbook, Elements of Chemistry - Earth, Air, Fire and Water, Vol. 1. Experiment 1.14.10 In this
    Message 1 of 7 , Sep 30, 2002
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      Here's a little experiment from my old high school chemistry textbook, Elements of Chemistry - Earth, Air, Fire and Water, Vol. 1.

      Experiment 1.14.10
      In this experiment, you can make some esters with familiar odours.
      (a) ethyl acetate
      - Use a dropper pipette to put about 2mL of glacial acetic acid, CH3COOH, into a test tube.
      - Use a clean dropper pipette to add an equal volume of ethanol, C2H5OH.
      - Use another dropper pipette to CAREFULLY add about 1mL of concentrated sulfuric acid.
      - Stir the mixture slightly and then place the test tube in a boiling water bath on a hot plate.
      - After about five minutes, pour the contents of teh test tube into a beaker containing about 10mL of water. Unreacted acetic acid and alcohol dissolve in the water, leaving the insoluble ester produced floating on the surface.
      - Describe the odour of the ethyl acetate.

      Well, pure acetic acid is hard to find. Vinegar is only about 15%, but I wonder. Sulfuric acid can be obtained from a car battery. I already have some nice and strong alcohol. I'll just have to give this a go...

      Also taken from the same book:
      Ethyl Acetate is an ester. Esters are formed by reaction between an alcohol and a carboxylic acid in the presence of concentrated sulfuric acid. Many esters occur naturally. They have pleasing fragrances and are responsible for the flavours and fragrances of many fruits and flowers.

      Fats and oils are also esters. Esters are volatile liquids, not ionized, and are soluble in organic solvents but not in water.

      Acetone on the other hand is a Ketone, it's systematic name is actually propanone. Acetone is commonly used as a solvent for plastics, varnishes and greases. Having worked with acetone in many industrial situations, I can assure you that the acrid part of the nail-polish smell commonly described is that of acetone. The same smell can be smelt in many epoxy glues, slicone glues, and even in fibreglass resin.

      As for fingernail polish remover, I don't know. I'll get hold of some and see if it dissolves in water. If it does, then it is not mainly ethyl-acetate. I can't see that smearing an oil onto your fingers will dissolve anything though.

      Mike G


      > Date: Mon, 30 Sep 2002 10:58:29 +1200
      > From: "Mike Nixon" <mike@...>
      >Subject: Re: Ethyl-Acetate (wrongly demonized ?)
      >
      >homedistiller wrote:
      >Subject: [Distillers] Ethyl-Acetate (wrongly demonized ?)
      >
      >In most, if not all posts, ethyl-acetate is considered and described
      >as an evil contributor to the desired end-product. It is treated the
      >same way as acetone and methanol.
      >
      >But, some research on the internet brought up articles where ethyl-
      >acetate is described as "very aromatic" or having a nice "fruity"
      >perfumed fragrance.
      >
      >On top of this, I have a book with recipes for cognacs, arak, etc.
      >where ethyl-acetate is sometimes ADDED and this in not so small
      >quantities: between 1% and 5% volume of the pure ethanol content!
      >
      >It seems also to be an important component in many essences for
      >strong drinks!
      >
      >None of the recipes ask for acetone or methanol and I don't feel
      >sorry for those, but after this latest information, I start to
      >"sympathize" with the ethyl-acetate.
      >
      >Is it possible that it is wrongly accused of being an enemy, while it
      >might be a friend ?
      >
      >Sincerely,
      >Dirk
      >=======================================
      >It's just a question of how much salt do you want in your soup?
      >Ethyl acetate is a chemical found naturally in many fruits, and is indeed useful as a flavoring agent in many foodstuffs and drinks. Small amounts won't harm you. However, like many things, you can have too much of a good thing, and the amount produced during fermentation can be overwhelming. Ordinary distillation will never enable you to get rid of all of it, but you can reduce the amount to desirable levels by extracting it with the heads. If making vodka, then you will want as little as possible, but if the aim is a whiskey, brandy or rum, then a touch of ethyl acetate is one of the things you want, together all the other flavorsome goodies.
      >
      >Just a touch though. Concentrated ethyl acetate is used as fingernail polish remover (sometimes mixed with acetone), so you can imagine what too much will do to your flavor buds! To get some idea of how much you might want in your drinks, why not try a dilution taste test? Get some clean 40% spirit (buy some vodka if your own product is not clean enough) and add a drop of pure ethyl acetate to it. You should be able to get the pure stuff from almost any drug store/chemist shop. Sniff the mix and then taste it ... just a swish in the mouth is enough ... then add another drop of ethyl acetate and taste again. You'll quickly get an idea of how much you want to collect from your still, and with careful measurement you could even work out the percentage you like or can tolerate best.
      >
      >Happy tasting!
      >Mike Nixon
      >
      >


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    • Michael
      Further to this. A little internet research has shown that nail polish remover can be based on two seperate solvents. Acetone is the first solvent. Acetone
      Message 2 of 7 , Oct 1, 2002
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        Further to this. A little internet research has shown that nail
        polish remover can be based on two seperate solvents. Acetone is the
        first solvent. Acetone being a highly effective industrial solvent.
        Ethyl acetate or similar ester is the second solvent. Nail polish
        removers based around ethyl acetate are advertised as being "Acetone
        Free" or "Without Acetone Odor".

        The MSDS's for Acetone describe it's odor as "fragrant, sweet and
        minty". The MSDS's for Ethyl Acetate describe it's odor as
        "fragrant, sweet and fruity". In the end, I don't bloody know...
        Just going to have to make some. How do you concentrate acetic acid?



        --- In Distillers@y..., Mike Gasmier <god@p...> wrote:
        > Here's a little experiment from my old high school chemistry
        textbook, Elements of Chemistry - Earth, Air, Fire and Water, Vol. 1.
        >
        > Experiment 1.14.10
        > In this experiment, you can make some esters with familiar odours.
        > (a) ethyl acetate
        > - Use a dropper pipette to put about 2mL of glacial acetic acid,
        CH3COOH, into a test tube.
        > - Use a clean dropper pipette to add an equal volume of ethanol,
        C2H5OH.
        > - Use another dropper pipette to CAREFULLY add about 1mL of
        concentrated sulfuric acid.
        > - Stir the mixture slightly and then place the test tube in a
        boiling water bath on a hot plate.
        > - After about five minutes, pour the contents of teh test tube into
        a beaker containing about 10mL of water. Unreacted acetic acid and
        alcohol dissolve in the water, leaving the insoluble ester produced
        floating on the surface.
        > - Describe the odour of the ethyl acetate.
        >
        > Well, pure acetic acid is hard to find. Vinegar is only about 15%,
        but I wonder. Sulfuric acid can be obtained from a car battery. I
        already have some nice and strong alcohol. I'll just have to give
        this a go...
        >
        > Also taken from the same book:
        > Ethyl Acetate is an ester. Esters are formed by reaction between
        an alcohol and a carboxylic acid in the presence of concentrated
        sulfuric acid. Many esters occur naturally. They have pleasing
        fragrances and are responsible for the flavours and fragrances of
        many fruits and flowers.
        >
        > Fats and oils are also esters. Esters are volatile liquids, not
        ionized, and are soluble in organic solvents but not in water.
        >
        > Acetone on the other hand is a Ketone, it's systematic name is
        actually propanone. Acetone is commonly used as a solvent for
        plastics, varnishes and greases. Having worked with acetone in many
        industrial situations, I can assure you that the acrid part of the
        nail-polish smell commonly described is that of acetone. The same
        smell can be smelt in many epoxy glues, slicone glues, and even in
        fibreglass resin.
        >
        > As for fingernail polish remover, I don't know. I'll get hold of
        some and see if it dissolves in water. If it does, then it is not
        mainly ethyl-acetate. I can't see that smearing an oil onto your
        fingers will dissolve anything though.
        >
        > Mike G
        >
      • B Morey
        From: Michael [mailto:god@perthmail.com] ... I always keep a litre of acetone in the shed -- it s a tremendously useful cleaner and solvent around the
        Message 3 of 7 , Oct 1, 2002
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          From: Michael [mailto:god@...]

          > The MSDS's for Acetone describe it's odor as "fragrant, sweet and
          > minty". The MSDS's for Ethyl Acetate describe it's odor as
          > "fragrant, sweet and fruity". In the end, I don't bloody know...
          > Just going to have to make some. How do you concentrate acetic acid?

          I always keep a litre of acetone in the shed -- it's a tremendously
          useful cleaner and solvent around the workshop. However, it that's
          "fragrant, sweet and fruity" either my sense of smell is completely
          kyboshed, or the tester sniffed *something else* first.

          Bernard
        • homedistiller
          Well Mike, You are energetic in your research. Thanks already for all the interesting findings. I was mixed up by the use of solvent smell in some of the
          Message 4 of 7 , Oct 1, 2002
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            Well Mike,

            You are energetic in your research.
            Thanks already for all the interesting findings.

            I was mixed up by the use of "solvent smell" in some of the postings.
            "Solvent" really is a general term. There are many solvents and they
            all smell different.

            In the meantime, I see now that it is possible to have nice flavours,
            but in too high concentrations. Acetone and methanol are fully
            undesired, ethyl acetate seems to be a wanted flavour in many
            distillates.

            Then there is the point that certain chemicals can have a nice smell
            but at the same time taste quite differently.

            Taste and smell seem to be VERY complex mechanisms and I am happy
            with that.

            Sooner or later I'll do what Mike Nixon advised. I'll buy some ethyl
            acetate, I guess in a pharmacy, and add some drops to tasteless
            ethanol to evaluate the effect.

            Sincerely,
            Dirk
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