Difference between revisions of "Formic acid"

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[[File:Formic acid.svg.png|thumb|100x100px]]
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{{Chembox
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| Name = Formic acid
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| Reference =
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| IUPACName = Methanoic acid
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| PIN = Methanoic acid
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| SystematicName = Methanoic acid
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| OtherNames = Aminic acid<br>Bilorin<br>Carbonous acid<br>Formylic acid<br>Hydrogen carboxylic acid<br>Hydroxy(oxo)methane<br>Metacarbonoic acid<br>Oxocarbinic acid<br>Oxomethanol
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| ImageFile1 = Formic acid bottle and sample.jpg
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| ImageSize1 = 300
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| ImageAlt1 =
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| ImageName1 =
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| ImageCaption1 = Formic acid sample and original bottle
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| ImageFile2 = Formic acid.svg.png
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| ImageSize2 = 250
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| ImageAlt2 =
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| ImageName2 =
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| ImageCaption2 = Structure of formic acid
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES =
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  }}
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless liquid
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| BoilingPt =
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| BoilingPtC = 100.8
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 1.220 g/cm<sup>3</sup> (20 °C)
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| Formula = CH<sub>2</sub>O<sub>2</sub><br>HCOOH
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| HenryConstant =
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| LogP = −0.54
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| MolarMass = 46.03 g/mol
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| MeltingPt =
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| MeltingPtC = 8.4
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| MeltingPt_ref =
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| MeltingPt_notes =
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| Odor = Pungent, ants-like
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| pKa = 3.77
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| pKb =
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| Solubility = Miscible
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| SolubleOther = Reacts with amines, bases<br>Miscible with [[acetone]], [[diethyl ether]], [[ethanol]], [[ethyl acetate]], [[glycerol]], [[methanol]]<br>Partially soluble in [[benzene]], [[toluene]], [[xylene]]
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| Solvent =
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| VaporPressure = 35 mmHg (20 °C)
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  }}
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| Section3 = {{Chembox Structure
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| Coordination =
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| CrystalStruct =
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| MolShape = Planar
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| Section4 = {{Chembox Thermochemistry
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| DeltaGf =
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| DeltaHc = −254.6 kJ/mol
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| DeltaHf = −425.0 kJ/mol
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| Entropy = 131.8 J·mol<sup>-1</sup>·K<sup>-1</sup>
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| HeatCapacity =
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  }}
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| Section5 = {{Chembox Explosive
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| ShockSens =
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| FrictionSens =
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| DetonationV =
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| REFactor =
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 601 °C (1,114 °F; 874 K)
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| ExploLimits = 14–34%<br>18%–57% (90% solution)
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| ExternalMSDS = [https://www.docdroid.net/PzeRYhw/formic-acid-85-sa.pdf.html Sigma-Aldrich] (85% solution)
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| FlashPt = 69 °C (156 °F; 342 K)
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| LD50 = 700 mg/kg (mouse, oral)<br>1,100 mg/kg (rat, oral)<br>4,000 mg/kg (dog, oral)
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| LC50 = 7,853 ppm (rat, 15 min)<br>3,246 ppm (mouse, 15 min)
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| MainHazards = Corrosive<br>Toxic
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| NFPA-F =
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| NFPA-H =
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| NFPA-R =
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| NFPA-S =
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| Section7 = {{Chembox Related
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| OtherAnions =
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| OtherCations =
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| OtherFunction =
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| OtherFunction_label =
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| OtherCompounds = [[Acetic acid]]<br>[[Oxalic acid]]
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  }}
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}}
 
'''Formic acid''' or '''methanoic acid''' is an organic compound with chemical formula '''HCOOH''' and the simplest carboxylic acid.
 
'''Formic acid''' or '''methanoic acid''' is an organic compound with chemical formula '''HCOOH''' and the simplest carboxylic acid.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
Formic acid is readily dehydrated by concentrated sulfuric acid to [[carbon monoxide]], and is often used in the lab as a convenient and store-able source of the gas. As with other carboxylic acids, formic acid is easily [[esterification|esterified]] with primary alcohols, often forming pleasant-smelling compounds such as [[methyl formate]].
+
Formic acid is readily dehydrated by concentrated [[sulfuric acid]] to [[carbon monoxide]], and is often used in the lab as a convenient and store-able source of the gas.
−
In organic chemistry, formic acid is used to introduce a [[formyl]] group.
+
 
 +
: HCOOH + H<sub>2</sub>SO<sub>4</sub>  → CO + H<sub>2</sub>O + H<sub>2</sub>SO<sub>4</sub>
 +
 
 +
As with other carboxylic acids, formic acid is easily [[esterification|esterified]] with primary alcohols, often forming pleasant-smelling compounds such as [[methyl formate]]. Being a strong acid, esterifications with formic acid generally don't require an acid catalyst.
 +
 
 +
In organic chemistry, formic acid is used to introduce a formyl group.
  
 
===Physical===
 
===Physical===
 
Formic acid is a clear liquid with a highly irritating pungent odor, and is responsible for the painful sensation of many ant stings. Its boiling point is nearly the same as water (100.8 ˚C), though it forms an azeotrope of 22.4% formic acid with water that boils instead at 107.3 ˚C.
 
Formic acid is a clear liquid with a highly irritating pungent odor, and is responsible for the painful sensation of many ant stings. Its boiling point is nearly the same as water (100.8 ˚C), though it forms an azeotrope of 22.4% formic acid with water that boils instead at 107.3 ˚C.
 +
 +
Since formic acid slowly decomposes when boiled, distillation must be done at low temperature and in near vacuum (25 °C at 40 mm Hg).<ref>Purification of Laboratory Chemicals (Fifth Edition), Wilfred L.F. Armarego and Christina Li Lin Chai, 2003</ref>
  
 
==Availability==
 
==Availability==
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==Preparation==
 
==Preparation==
−
Aqueous formic acid can be distilled from a mixture of anhydrous [[glycerol]] and [[oxalic acid]], producing carbon dioxide as a byproduct. It can also be obtained by acidifying [[sodium formate]] with '''dilute''' [[sulfuric acid]], producing formic acid in solution that can then be distilled over. Using concentrated sulfuric acid or heating too much will produce [[carbon monoxide]] and potentially create a very dangerous situation.
+
Aqueous formic acid can be distilled from a mixture of anhydrous [[glycerol]] and [[oxalic acid]], producing carbon dioxide as a byproduct.<ref>NurdRage, ''Make Formic Acid'', [https://www.youtube.com/watch?v=ceL-I0azPH8 https://www.youtube.com/watch?v=ceL-I0azPH8]</ref> It can also be obtained by acidifying [[sodium formate]] with '''dilute''' [[sulfuric acid]] or [[phosphoric acid]], producing formic acid in solution that can then be distilled over. Using concentrated sulfuric acid or heating too much will produce [[carbon monoxide]] and potentially create a very dangerous situation.
  
 
==Projects==
 
==Projects==
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==Handling==
 
==Handling==
 
===Safety===
 
===Safety===
−
Concentrated solutions of formic acid are corrosive to human skin, and also slowly decompose to form water and carbon monoxide, which can cause an explosion from pressure buildup in a sealed container. Adding a dehydrating agent will also generate large amounts of carbon monoxide, a deadly gas that is impossible to detect with human senses. Formic acid is not inherently very toxic if ingested, though long exposure to it by any means can cause chronic bodily effects. It is especially important that formic acid is kept away from the eyes, as it readily damages the optic nerve and can cause permanent blindness.
+
Concentrated solutions of formic acid are corrosive to human skin, as well as nose, mouth and eyes and also slowly decompose to form water and carbon monoxide, which can cause an explosion from pressure buildup in a sealed container. Adding a dehydrating agent will also generate large amounts of carbon monoxide, a deadly gas that is impossible to detect with human senses. Formic acid is not inherently very toxic if ingested, though long exposure to it by any means can cause chronic bodily effects. It is especially important that formic acid is kept away from the eyes, as it readily damages the optic nerve and can cause permanent blindness.
  
 
===Storage===
 
===Storage===
−
Formic acid should be stored in closed bottles, away from any heat source.
+
Formic acid should be stored in closed bottles, away from any heat source. Keep it away from dwelling areas, as it slowly gives off carbon monoxide over time.
  
 
===Disposal===
 
===Disposal===
−
Formic acid should be neutralized before disposal.
+
Formic acid should be neutralized before disposal. This can be done by diluting the acid, then slowly adding it in an aqueous solution of a base. like [[sodium carbonate]] or [[sodium bicarbonate]].
  
 
==References==
 
==References==
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===Relevant Sciencemadness threads===
 
===Relevant Sciencemadness threads===
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=21186 Make Formic Acid]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=21186 Make Formic Acid]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=19129 Formic Acid]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=35568 Handling Formic Acid? Strength compared to other acids?]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=1782 Formic acid, manufacture/procurement]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=63113 Formic acid]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=20266 Formic acid descaler available.]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=65024 Formic Acid Fuel Cell]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=24542 Formic Acid from Esy Off Bam]
 +
*[http://www.sciencemadness.org/talk/viewthread.php?tid=72461 Drying formic acid with molecular sieves - CO risk?]
  
 
[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Organic compounds]]
 
[[Category:Acids]]
 
[[Category:Acids]]
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[[Category:Mid-strength acids]]
 
[[Category:Carboxylic acids]]
 
[[Category:Carboxylic acids]]
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[[Category:Solvents]]
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[[Category:Polar solvents]]
 +
[[Category:Protic solvents]]
 
[[Category:Volatile chemicals]]
 
[[Category:Volatile chemicals]]
 
[[Category:Corrosive chemicals]]
 
[[Category:Corrosive chemicals]]
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[[Category:Vesicants]]
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[[Category:Neurotoxins]]
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[[Category:Liquids]]
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[[Category:DEA SS List]]
 +
[[Category:Irritants]]
 +
[[Category:Reducing agents]]
 +
[[Category:Essential reagents]]

Latest revision as of 15:05, 18 November 2023

Formic acid
Formic acid bottle and sample.jpg
Formic acid sample and original bottle
Formic acid.svg.png
Structure of formic acid
Names
IUPAC name
Methanoic acid
Preferred IUPAC name
Methanoic acid
Systematic IUPAC name
Methanoic acid
Other names
Aminic acid
Bilorin
Carbonous acid
Formylic acid
Hydrogen carboxylic acid
Hydroxy(oxo)methane
Metacarbonoic acid
Oxocarbinic acid
Oxomethanol
Properties
CH2O2
HCOOH
Molar mass 46.03 g/mol
Appearance Colorless liquid
Odor Pungent, ants-like
Density 1.220 g/cm3 (20 °C)
Melting point 8.4 °C (47.1 °F; 281.5 K)
Boiling point 100.8 °C (213.4 °F; 373.9 K)
Miscible
Solubility Reacts with amines, bases
Miscible with acetone, diethyl ether, ethanol, ethyl acetate, glycerol, methanol
Partially soluble in benzene, toluene, xylene
Vapor pressure 35 mmHg (20 °C)
Acidity (pKa) 3.77
Thermochemistry
131.8 J·mol-1·K-1
−425.0 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich (85% solution)
Flash point 69 °C (156 °F; 342 K)
Lethal dose or concentration (LD, LC):
700 mg/kg (mouse, oral)
1,100 mg/kg (rat, oral)
4,000 mg/kg (dog, oral)
7,853 ppm (rat, 15 min)
3,246 ppm (mouse, 15 min)
Related compounds
Related compounds
 Acetic acid
Oxalic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Formic acid or methanoic acid is an organic compound with chemical formula HCOOH and the simplest carboxylic acid.

Properties

Chemical

Formic acid is readily dehydrated by concentrated sulfuric acid to carbon monoxide, and is often used in the lab as a convenient and store-able source of the gas.

HCOOH + H2SO4 → CO + H2O + H2SO4

As with other carboxylic acids, formic acid is easily esterified with primary alcohols, often forming pleasant-smelling compounds such as methyl formate. Being a strong acid, esterifications with formic acid generally don't require an acid catalyst.

In organic chemistry, formic acid is used to introduce a formyl group.

Physical

Formic acid is a clear liquid with a highly irritating pungent odor, and is responsible for the painful sensation of many ant stings. Its boiling point is nearly the same as water (100.8 ˚C), though it forms an azeotrope of 22.4% formic acid with water that boils instead at 107.3 ˚C.

Since formic acid slowly decomposes when boiled, distillation must be done at low temperature and in near vacuum (25 °C at 40 mm Hg).[1]

Availability

While not typically found as a consumer product, formic acid can be bought online for relatively low prices, typically mixed with about 5-10% water. A good supplier is Duda Diesel.

Formic acid can also be purchased at beekeeping stores, as 60-85% concentration. It is used for the treatment of Varroasis.

Preparation

Aqueous formic acid can be distilled from a mixture of anhydrous glycerol and oxalic acid, producing carbon dioxide as a byproduct.[2] It can also be obtained by acidifying sodium formate with dilute sulfuric acid or phosphoric acid, producing formic acid in solution that can then be distilled over. Using concentrated sulfuric acid or heating too much will produce carbon monoxide and potentially create a very dangerous situation.

Projects

Handling

Safety

Concentrated solutions of formic acid are corrosive to human skin, as well as nose, mouth and eyes and also slowly decompose to form water and carbon monoxide, which can cause an explosion from pressure buildup in a sealed container. Adding a dehydrating agent will also generate large amounts of carbon monoxide, a deadly gas that is impossible to detect with human senses. Formic acid is not inherently very toxic if ingested, though long exposure to it by any means can cause chronic bodily effects. It is especially important that formic acid is kept away from the eyes, as it readily damages the optic nerve and can cause permanent blindness.

Storage

Formic acid should be stored in closed bottles, away from any heat source. Keep it away from dwelling areas, as it slowly gives off carbon monoxide over time.

Disposal

Formic acid should be neutralized before disposal. This can be done by diluting the acid, then slowly adding it in an aqueous solution of a base. like sodium carbonate or sodium bicarbonate.

References

  1. ↑ Purification of Laboratory Chemicals (Fifth Edition), Wilfred L.F. Armarego and Christina Li Lin Chai, 2003
  2. ↑ NurdRage, Make Formic Acid, https://www.youtube.com/watch?v=ceL-I0azPH8

Relevant Sciencemadness threads

Retrieved from "https://www.sciencemadness.org/smwiki/index.php?title=Formic_acid&oldid=15426"