Making Formic Acid

00:03:35
https://www.youtube.com/watch?v=eEY3PUWMSl4

Summary

TLDRThis video outlines the synthesis of formic acid through the decomposition of oxalic acid. It details the initial setup with oxalic acid dihydrate and glycerin, followed by distillation at controlled temperatures to prevent toxic byproducts. The reaction proceeds with additional oxalic acid and water to maximize formic acid production. After distillation, fractional distillation is employed to purify formic acid from impurities. The video concludes with a note about the quantity obtained and mentions the creator's intent to prioritize the synthesis process in their content.

Takeaways

  • 🔬 The synthesis focuses on formic acid production from oxalic acid.
  • 🧪 Glycerin acts as a catalyst during the distillation process.
  • 🌡️ Monitoring temperature is crucial to avoid toxic byproducts.
  • 💧 Additional oxalic acid dihydrate is added to sustain the reaction.
  • 🌡️ Fractional distillation separates formic acid from impurities.
  • 📊 The final yield of formic acid was over 125 milliliters.
  • 🛑 The creator emphasizes process over product purity in their videos.
  • 🔄 The reaction can be repeated for higher yields of formic acid.
  • 🔍 Viewers may find a purification tutorial upon request.

Timeline

  • 00:00:00 - 00:03:35

    The video demonstrates the synthesis of formic acid from oxalic acid by a decarboxylation reaction. The process begins with the addition of 100 grams of oxalic acid dihydrate and 100 milliliters of glycerin to a boiling flask, which acts as a catalyst. It emphasizes the importance of monitoring the temperature of the reaction mixture, particularly keeping it around 110 degrees Celsius to avoid toxic byproducts. Further oxalic acid dihydrate is added to maintain the reaction, allowing continuous generation of formic acid. After heating and collecting distillates, the mixture of formic acid, water, and toxic byproducts undergoes fractional distillation to separate pure formic acid from contaminants, ultimately yielding over 125 milliliters of formic acid. The narrator acknowledges the practicality of purification but opts to keep the videos concise, inviting viewers to express interest in further purification content.

Mind Map

Video Q&A

  • What acid is synthesized in this process?

    Formic acid is synthesized from the decomposition of oxalic acid.

  • What role does glycerin play in the synthesis?

    Glycerin acts as a catalyst to help drive the reaction forward.

  • At what temperature should the reaction mixture be monitored during the distillation?

    The reaction mixture should be monitored at around 110 degrees Celsius.

  • What happens if the temperature exceeds 110 degrees Celsius?

    Exceeding this temperature can produce toxic byproducts such as acrylonitrile or allyl alcohol.

  • How is the reaction continued after initial distillation?

    By adding more oxalic acid dihydrate to provide additional water and oxalic acid.

  • What technique is used to purify the formic acid at the end?

    Fractional distillation is used to separate formic acid from toxic byproducts.

  • What was the final yield of formic acid?

    The final yield was a little over 125 milliliters.

  • Why doesn't the creator demonstrate product purification?

    The creator prefers to keep the videos short and focused on the synthesis process.

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  • 00:00:00
    today I'm going to synthesize bormic
  • 00:00:02
    acid by the decomposition of oxalic acid
  • 00:00:04
    and I begin by adding 100 grams of
  • 00:00:06
    oxalic acid dihydrate to a three neck
  • 00:00:09
    boiling flask oxalic acid is the
  • 00:00:11
    simplest dicarboxylic acid and when it's
  • 00:00:14
    decarboxylated it forms formic acid
  • 00:00:16
    which is the simplest carboxylic acid
  • 00:00:18
    simply heating oxalic acid though will
  • 00:00:21
    decompose the majority of it so 100
  • 00:00:23
    milliliters of Glycerin or glycerol is
  • 00:00:26
    added to act as a catalyst
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    this is set up for a simple distillation
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    and heated to 125 degrees Celsius
  • 00:00:34
    I want to use a thermometer here but I
  • 00:00:36
    want to place the thermometer in the
  • 00:00:37
    reaction mixture or as close to it as
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    possible as it's more important to
  • 00:00:41
    monitor the temperature of the reaction
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    mixture rather than the vapor phase in
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    this situation
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    this is done because the target reaction
  • 00:00:50
    takes place at 110 degrees Celsius and
  • 00:00:53
    temperatures too far above this will
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    produce toxic byproducts such as acrylon
  • 00:00:58
    or alyl alcohol which you really don't
  • 00:01:00
    want
  • 00:01:01
    I've included the reaction mechanism
  • 00:01:02
    here and you can pause it if you're
  • 00:01:04
    interested and I also want to note that
  • 00:01:06
    formic acid shares its name with a type
  • 00:01:08
    of wood ant that sprays formic acid as a
  • 00:01:11
    means of self-defense which is pretty
  • 00:01:13
    interesting
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    in any case eventually you get some
  • 00:01:16
    distillate coming over but there's not a
  • 00:01:18
    lot of formic acid here and this is
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    because this reaction relies on an
  • 00:01:22
    excess of water present in order to
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    drive it forward
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    to remedy this I add 110 grams more
  • 00:01:28
    oxalic acid dihydrate to provide more
  • 00:01:31
    water and more oxalic acid to keep the
  • 00:01:34
    reaction going forward
  • 00:01:35
    this step can be repeated as many times
  • 00:01:37
    as you want to continue generating more
  • 00:01:39
    formic acid because the glycerol acts as
  • 00:01:42
    a catalyst and is regenerated at the end
  • 00:01:44
    of the reaction and never actually used
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    up
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    to that end I keep collecting distillate
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    until the bubbling stops again before
  • 00:01:51
    adding 50 milliliters of distilled water
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    this is going to help the reaction go to
  • 00:01:55
    completion and at this point I collect
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    everything that distills over up to 120
  • 00:02:00
    degrees Celsius before cutting the Heat
  • 00:02:02
    and allowing it to cool
  • 00:02:04
    at this point I'm left with a really
  • 00:02:05
    crude mixture of formic acid water and
  • 00:02:09
    the toxic byproducts and for the Final
  • 00:02:11
    Phase of this reaction I'm going to
  • 00:02:13
    separate those using fractional
  • 00:02:14
    distillation the fractional distillation
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    is pretty standard and I begin by adding
  • 00:02:19
    my crude formic acid to another boiling
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    flask and setting up my praxental
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    distillation as shown
  • 00:02:24
    the toxic acrylene and allyl alcohol
  • 00:02:27
    impurities have very low boiling points
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    and will boil away long before any
  • 00:02:31
    formic acid or water does water will
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    begin to distill away at around 100
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    degrees Celsius and a 77.5 percent
  • 00:02:39
    asiotrope of formic acid and water will
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    distill over at around 105 degrees
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    Celsius
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    that said I want to collect everything
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    that distills up to 104 degrees Celsius
  • 00:02:49
    and discard it as waste
  • 00:02:51
    at that point I'll switch out my
  • 00:02:53
    collection flask and begin collecting
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    pure 77.5 azeotropic formic acid
  • 00:02:59
    in the end I got a little over 125
  • 00:03:01
    milliliters of formic acid and I didn't
  • 00:03:04
    titrate it for Purity but I can if you
  • 00:03:06
    guys are interested
  • 00:03:08
    on the topic of Purity I get comments
  • 00:03:10
    from time to time about how my product
  • 00:03:11
    is not entirely pure and I am aware of
  • 00:03:14
    that
  • 00:03:15
    dehydration and purification of products
  • 00:03:18
    is an incredibly easy process that I'm
  • 00:03:20
    more than capable of doing the main
  • 00:03:22
    reason I don't is that I really want my
  • 00:03:24
    videos to stay short and emphasize the
  • 00:03:26
    process rather than be a boring size
  • 00:03:28
    tutorial if you'd like to see some
  • 00:03:30
    purification videos consider giving me a
  • 00:03:33
    follow and let me know
Tags
  • formic acid
  • oxalic acid
  • synthesis
  • catalyst
  • distillation
  • fractional distillation
  • chemical reaction
  • toxic byproducts
  • purity
  • glycerin