What is the systematic IUPAC name for formic acid, and what is its chemical formula?

The systematic IUPAC name for formic acid is methanoic acid. Its chemical formula is HCOOH, representing a molecule with one hydrogen atom, one carbon atom, two oxygen atoms, and one hydrogen atom bonded to the oxygen.

What is formic acid's significance in chemical synthesis and its natural occurrence?

Formic acid serves as an important intermediate in chemical synthesis. It also occurs naturally, most notably being found in certain species of ants.

What are formates, and how are they related to formic acid?

Formates are the esters, salts, and the anion derived from formic acid. They share the basic structure related to formic acid.

How is formic acid primarily produced industrially?

Industrially, formic acid is produced from methanol. This process involves converting methanol into methyl formate, which is then hydrolyzed.

Where can formic acid be found naturally in the environment?

Formic acid is found naturally in various sources, including insects (like ants), weeds, fruits, vegetables, and as a component in atmospheric emissions from forests.

Which specific insects are known to contain or secrete formic acid?

Formic acid is notably present in ants, which use it for attack and defense. It is also found in stingless bees of the genus Oxytrigona, and wood ants of the genus Formica spray it for defense or predation.

Beyond insects, what other natural sources contain formic acid?

Formic acid is present in the trichomes of stinging nettles (Urtica dioica). It is also found in fruits like pineapple, apples, and kiwis, and in vegetables such as onions, eggplants, and cucumbers, albeit in varying concentrations.

What historical observations were made regarding formic acid's presence?

As early as the 15th century, alchemists and naturalists observed that ant hills emitted an acidic vapor. The English naturalist John Ray first described the isolation of this substance in 1671 by distilling large numbers of ants.

Who were the key chemists involved in the early synthesis of formic acid?

Joseph Gay-Lussac, a French chemist, first synthesized formic acid from hydrocyanic acid. Later, in 1855, Marcellin Berthelot, also a French chemist, developed a synthesis method from carbon monoxide, which is similar to modern industrial processes.

How did the industrial importance of formic acid change over time?

Formic acid was initially considered a chemical of minor industrial interest. However, in the late 1960s, its availability increased significantly as a byproduct of acetic acid production, leading to its growing use, particularly as a preservative and antibacterial agent in livestock feed.

Describe the physical properties of formic acid at room temperature.

At room temperature, formic acid is a colorless liquid with a pungent, penetrating odor, similar to acetic acid.

How does the acidity of formic acid compare to acetic acid?

Formic acid is significantly stronger than acetic acid. Its pKa value is 3.745, whereas acetic acid's pKa is 4.756, indicating formic acid dissociates more readily in water.

What are the solubility characteristics of formic acid?

Formic acid is miscible with water and most polar organic solvents. It also shows some solubility in hydrocarbons.

How does formic acid exist in the vapor phase and in solid form?

In the vapor phase and in nonpolar solvents like hydrocarbons, formic acid molecules tend to form hydrogen-bonded dimers. In its solid state, formic acid exists as an extensive network of hydrogen-bonded molecules, forming two different crystalline structures called polymorphs.

Does gaseous formic acid obey the ideal gas law, and why?

Gaseous formic acid does not strictly obey the ideal gas law because its molecules readily form hydrogen bonds, influencing their behavior compared to ideal gas particles.

What is an azeotrope, and what azeotrope does formic acid form?

An azeotrope is a mixture of two or more liquids whose proportions cannot be altered by simple distillation. Formic acid forms a high-boiling azeotrope with water, containing 77.5% formic acid and boiling at 107.3 °C.

What happens when formic acid is heated with concentrated sulfuric acid?

When formic acid is heated with concentrated sulfuric acid, it readily decomposes through dehydration to form carbon monoxide and water. This reaction is a common laboratory method for producing carbon monoxide.

What are the products when formic acid decomposes in the presence of platinum?

In the presence of platinum, formic acid decomposes to produce hydrogen gas and carbon dioxide.

How does formic acid behave in Fischer esterification reactions?

In Fischer esterifications, formic acid acts as both a reactant and a catalyst due to its acidity. It can self-catalyze the reaction with alcohols to form esters, meaning no additional acid catalyst is typically required.

How is formic acid used as a source of a formyl group in organic synthesis?

Formic acid can serve as a source for a formyl group, for instance, in the formylation of N-methylaniline to produce N-methylformanilide, typically carried out in a solvent like toluene.

In what way is formic acid utilized in transfer hydrogenation reactions?

In synthetic organic chemistry, formic acid is used as a source of hydride ions. It is employed in reactions like the Eschweiler-Clarke reaction for methylation and in the Leuckart reaction to synthesize amines. It can also be used for the hydrogenation of ketones.

What unique addition reaction can formic acid undergo with alkenes?

Formic acid is unique among carboxylic acids in its ability to add to alkenes. While it typically forms formate esters, under acidic conditions (like with sulfuric or hydrofluoric acid), it can undergo a variant of the Koch reaction to produce larger carboxylic acids.

What is formic acid anhydride, and how is it synthesized?

Formic acid anhydride, with the structure H(C=O)-O-(C=O)H, is an unstable compound. It can be synthesized by dehydrating formic acid using N,N'-dicyclohexylcarbodiimide in ether at low temperatures.

What was the global production capacity for formic acid in 2009, and where was it concentrated?

In 2009, the worldwide capacity for formic acid production was approximately 720,000 tonnes per year. This production was roughly equally divided between Europe (mainly Germany) and Asia (mainly China).

Which companies were the largest producers of formic acid in 2009?

The largest producers of formic acid in 2009 included BASF, Eastman Chemical Company, LC Industrial, and Feicheng Acid Chemicals.

What are the typical concentrations of commercially available formic acid solutions?

Formic acid is commercially available in solutions with concentrations ranging from 85% to 99% by weight.

How is formic acid produced from methanol and carbon monoxide?

Methanol and carbon monoxide react in the presence of a strong base, such as sodium methoxide, to form methyl formate. This methyl formate is then hydrolyzed with water to yield formic acid and regenerate methanol.

What is an alternative route to formic acid production involving formamide?

An indirect route involves reacting methyl formate with ammonia to produce formamide. Subsequently, formamide is hydrolyzed with sulfuric acid to yield formic acid and ammonium sulfate as a byproduct.

What is a disadvantage of the formamide route for formic acid production?

A disadvantage of the formamide route is the generation of ammonium sulfate as a byproduct, which requires disposal. Manufacturers have developed methods like liquid-liquid extraction to separate formic acid from water more efficiently.

How was acetic acid production historically linked to formic acid production?

Historically, acetic acid was produced on a large scale by oxidizing alkanes, a process that also generated significant amounts of formic acid as a co-product. However, this method has become less important compared to dedicated formic acid production routes.

What is the OxFA process, and how does it relate to formic acid production?

The OxFA process involves the aqueous catalytic partial oxidation of wet biomass. It uses a Keggin-type polyoxometalate catalyst to convert materials like sugars and wood into formic acid and carbon dioxide, achieving yields up to 53% formic acid.

Describe a laboratory method for preparing formic acid using oxalic acid.

In the laboratory, formic acid can be prepared by heating oxalic acid in glycerol, followed by steam distillation. Glycerol acts as a catalyst in this process, which proceeds via a glyceryl oxalate intermediate.

What is the electrochemical method for producing formate?

Formate can be produced electrochemically through the reduction of carbon dioxide (in the form of bicarbonate) at a lead cathode in an aqueous solution at pH 8.6. The overall reaction involves CO2, water, and electrons yielding formate and hydroxide ions.

How is formic acid synthesized biologically?

Formic acid is biosynthesized in organisms like ants from the amino acid serine. This process involves a 5,10-methenyltetrahydrofolate intermediate.

What is a major agricultural use of formic acid?

A significant use of formic acid in agriculture is as a preservative and antibacterial agent in livestock feed. It helps maintain the feed's nutritional value for longer periods by arresting decay processes.

How is formic acid used in silage production?

In silage production, formic acid is added to fresh hay and other forage to promote the fermentation of lactic acid while suppressing the formation of butyric acid. This allows for quicker fermentation at lower temperatures, reducing nutritional loss.

What role does formic acid play in beekeeping?

Beekeepers utilize formic acid as a miticide to control parasitic mites, specifically the tracheal mite (Acarapis woodi) and the Varroa destructor and Varroa jacobsoni mites, which can infest bee colonies.

How can formic acid be used in energy applications?

Formic acid can be used directly in formic acid fuel cells or indirectly in hydrogen fuel cells. It is also considered as a medium for hydrogen storage due to its liquid state and high hydrogen content per volume.

What are the advantages of using formic acid for hydrogen storage?

Formic acid offers advantages for hydrogen storage because it is a liquid at room temperature and atmospheric pressure, making it easier to handle than compressed hydrogen gas. It contains a higher density of hydrogen (53 g/L) compared to compressed hydrogen gas at 350 bar (14.7 g/L), and it has a relatively high flash point (69 °C), enhancing safety.

What is the potential application of formic acid in soldering?

Formic acid has potential applications in soldering due to its ability to reduce oxide layers on metal surfaces. When used as a gas, it can increase the wettability of solder on these oxidized surfaces.

How is formic acid utilized in chromatography?

Formic acid is used as a volatile pH modifier in techniques like High-Performance Liquid Chromatography (HPLC) and capillary electrophoresis. It is often included in the mobile phase for reversed-phase HPLC, particularly for separating hydrophobic macromolecules like proteins, and offers advantages over phosphoric acid when coupled with mass spectrometry.

What are some other industrial uses of formic acid?

Formic acid is used in the leather industry for tanning, and in the textile industry for dyeing and finishing processes due to its acidic properties. It also acts as a coagulant in rubber production and is found in various cleaning products, such as limescale removers.

What is the general toxicity profile of formic acid?

Formic acid has relatively low toxicity, evidenced by its use as a food additive and an oral LD50 of 1.8 g/kg in mice. However, concentrated formic acid is corrosive to the skin and eyes.

How does formic acid contribute to methanol poisoning?

When methanol is ingested, it is metabolized in the body to formaldehyde and then to formic acid. The accumulation of formic acid is primarily responsible for the optic nerve damage that can lead to blindness in cases of methanol poisoning.

What are the potential chronic health effects of exposure to formic acid?

Chronic exposure to formic acid may lead to kidney damage. Additionally, some studies suggest it can act as a mutagen in bacterial species, and repeated exposure in humans can potentially cause a skin allergy.

Why is 98% formic acid shipped in bottles with self-venting caps?

Concentrated formic acid (around 98%) can slowly decompose over time, producing carbon monoxide and water. This decomposition can lead to a pressure buildup within the container, necessitating the use of self-venting caps for safety.

How do the hazards of formic acid solutions vary with concentration according to GHS labeling?

According to GHS labeling, formic acid solutions between 2-10% concentration are classified as skin irritants (H315). Solutions between 10-90% are considered harmful in contact with skin (H313), while concentrations above 90% are classified as causing severe skin burns and eye damage (H314).

What is the OSHA Permissible Exposure Limit (PEL) for formic acid vapor?

The Occupational Safety and Health Administration (OSHA) has set the Permissible Exposure Limit (PEL) for formic acid vapor in the workplace at 5 parts per million (ppm) of air, measured as a time-weighted average (TWA).

What is the chemical structure of formic acid, and what does the image of the cyclic dimer illustrate?

Formic acid has the chemical formula HCOOH and a planar molecular shape. The provided image illustrates the cyclic dimer of formic acid, where two molecules are linked by hydrogen bonds, represented by dashed green lines.

What is the pKa of formic acid, and how does it compare to acetic acid?

The pKa of formic acid is 3.745, indicating it is a stronger acid than acetic acid, which has a pKa of 4.756. This means formic acid dissociates more readily in aqueous solutions.

Formic Acid Wiki: The Essence of Formic Acid: Properties, Production, and Applications

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What is Formic Acid?

The Simplest Acid

Formic acid, systematically named methanoic acid, is the simplest member of the carboxylic acid family. Its chemical formula is HCOOH, and its structure is represented as H−C(=O)−O−H. It is a crucial intermediate in various chemical synthesis pathways and occurs naturally, notably within ants, from which it derives its name (Latin: formica meaning 'ant').

Industrial Significance

While historically considered a minor industrial chemical, formic acid has gained significant importance. It is produced industrially primarily from methanol. Its applications span agriculture, energy, and various manufacturing processes, making it a versatile compound in modern chemistry.

Sensory Properties

In its pure form at room temperature, formic acid is a colorless liquid characterized by a pungent, penetrating odor. This distinct smell is noticeable even at low concentrations and is comparable to that of acetic acid, though formic acid is a significantly stronger acid.

Natural Occurrence

Found in Nature

Formic acid is prevalent in the natural world. It is notably found in the venom and secretions of many insects, including ants (genus Formica) and stingless bees (genus Oxytrigona), where it serves purposes of attack and defense. It is also present in the stinging trichomes of nettles (Urtica dioica).

In Foods and Atmosphere

Beyond insects, formic acid is a naturally occurring component in various fruits and vegetables, such as pineapples, apples, kiwis, onions, and eggplants, albeit typically in low concentrations. It is also identified as a component in the Earth's atmosphere, primarily originating from forest emissions.

Historical Context

Early Isolation and Synthesis

The acidic nature of ant secretions was noted by naturalists as early as the 15th century. The English naturalist John Ray first documented the isolation of formic acid in 1671 through the distillation of ants. Later, chemists like Joseph Gay-Lussac and Marcellin Berthelot developed early synthesis methods, with Berthelot establishing a route from carbon monoxide in 1855.

Rise in Industrial Use

Formic acid's industrial relevance grew significantly in the late 1960s when it became more readily available as a byproduct of acetic acid production. Its utility as a preservative and antibacterial agent, particularly in livestock feed, spurred increased demand and dedicated production methods.

Chemical and Physical Properties

Solubility and Structure

Formic acid is miscible with water and most polar organic solvents due to its ability to form hydrogen bonds. In the vapor phase and nonpolar solvents, it exists as hydrogen-bonded dimers. Solid formic acid exhibits polymorphism, forming extensive hydrogen-bonded networks. It forms a high-boiling azeotrope with water (77.5% formic acid).

Acidity and Strength

With a pK_a of 3.745, formic acid is considerably stronger than acetic acid (pK_a 4.756). This acidity influences its reactivity and applications, particularly in catalysis and as a pH modifier.

Physical Characteristics

Key physical properties include:

Appearance: Colorless, fuming liquid
Odor: Pungent, penetrating
Density: 1.220 g/mL
Melting Point: 8.4 °C
Boiling Point: 100.8 °C
Vapor Pressure: 35 mmHg at 20 °C

Additional properties include:

Flash Point: 69 °C
Autoignition Temperature: 601 °C
Explosive Limits: 14–34%
log P: -0.54
Refractive Index (n_D): 1.3714 at 20 °C
Magnetic Susceptibility: -19.90×10⁻⁶ cm³/mol

Chemical Reactivity

Decomposition Pathways

Formic acid readily decomposes under specific conditions. In the presence of concentrated sulfuric acid, it dehydrates to form carbon monoxide and water. Catalytic decomposition, particularly with platinum or ruthenium, yields hydrogen and carbon dioxide, offering a potential route for hydrogen storage and generation.

Reducing Agent and Formyl Source

Unique among carboxylic acids, formic acid exhibits reducing properties similar to aldehydes. It can reduce metal oxides and acts as a source for the formyl group in organic synthesis, such as in the formylation of anilines. It also serves as a hydride source in reactions like the Eschweiler–Clarke reaction.

Key reactions include:

Decomposition: HCOOH → H₂O + CO (with H₂SO₄) or HCOOH → H₂ + CO₂ (catalytic)
Esterification: Spontaneous reaction with alcohols, often self-catalyzed.
Addition to Alkenes: Can form formate esters or larger carboxylic acids under acidic conditions (Koch reaction variant).
Transfer Hydrogenation: Used as a hydrogen source in reactions like the Leuckart reaction for amine synthesis.

Industrial Production

Primary Synthesis Route

The dominant industrial method involves the reaction of methanol (CH₃OH) with carbon monoxide (CO) under pressure, typically using a strong base like sodium methoxide as a catalyst, to produce methyl formate (HCOOCH₃). This ester is subsequently hydrolyzed with water to yield formic acid and regenerate methanol.

CH₃OH + CO → HCOOCH₃

HCOOCH₃ + H₂O → HCOOH + CH₃OH

Alternative and Emerging Methods

Alternative routes include the hydrolysis of formamide (derived from methyl formate and ammonia), though this generates ammonium sulfate byproduct. Research is ongoing into efficient methods for CO₂ electrolysis and the catalytic oxidation of biomass (e.g., using Keggin-type catalysts) to produce formic acid, aligning with sustainable chemistry principles.

Global Production Landscape

Major producers include BASF and Eastman Chemical Company. Global production capacity is substantial, with significant manufacturing concentrated in Europe and Asia. Prices vary by region, reflecting production costs and market demand.

Diverse Applications

Agriculture and Animal Feed

A primary use is as a preservative and antibacterial agent in livestock feed, including silage and hay. It inhibits spoilage, preserves nutritional value, and helps control bacteria like E. coli in poultry feed. This application accounted for approximately 30% of global consumption in 2009.

Beekeeping and Pest Control

Beekeepers utilize formic acid solutions as a miticide to control parasitic mites, such as Varroa destructor and Acarapis woodi, which infest honeybee colonies. Its effectiveness makes it a valuable tool for maintaining apiary health.

Energy and Chemical Storage

Formic acid serves as a medium for hydrogen storage and is used directly in formic acid fuel cells. Its high hydrogen density and relatively safe handling characteristics make it an attractive alternative to compressed hydrogen gas for energy applications.

Industrial Processes

Significant volumes are used in the leather tanning industry and in textile dyeing and finishing due to its acidic properties. It also finds application as a coagulant in rubber production and as a component in various cleaning products, including limescale removers.

Analytical Chemistry

In analytical techniques like HPLC and capillary electrophoresis, formic acid is employed as a volatile pH modifier. Its compatibility with mass spectrometry makes it particularly useful for separating and analyzing complex hydrophobic molecules like peptides and proteins.

Safety and Handling

Toxicity and Corrosivity

Formic acid has relatively low systemic toxicity (LD50 in mice is 1.8 g/kg), and it is metabolized and eliminated by the body. However, concentrated solutions are corrosive to skin and eyes. The primary hazards stem from direct contact with the liquid or vapors.

Health Effects

Chronic exposure can potentially lead to kidney damage or skin sensitization (allergy). Importantly, formic acid and formaldehyde, its metabolite, are implicated in the optic nerve damage observed in methanol poisoning. Occupational exposure limits (e.g., OSHA PEL) are set to minimize risks in the workplace.

Hazard Classification

Concentrated formic acid (above 10%) is classified as corrosive (H314), causing severe skin burns and eye damage. Lower concentrations (2-10%) are irritants (H315). It is also flammable, with a flash point of 69 °C. Proper handling procedures and personal protective equipment are essential.

GHS Hazard Summary:

Pictograms: Flame (Flammable), Corrosive
Signal Word: Danger
Hazard Statements: H314 (Causes severe skin burns and eye damage)
Precautionary Statements: P260, P264, P280, P301+P330+P331, P303+P361+P353, P305+P351+P338, P310, P363, P405, P501

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References

Organic Acids and Food Preservation, Maria M. Theron, J. F. Rykers Lues

A full list of references for this article are available at the Formic acid Wikipedia page

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This page was generated by an Artificial Intelligence and is intended for informational and educational purposes only. The content is based on a snapshot of publicly available data from Wikipedia and may not be entirely accurate, complete, or up-to-date.

This is not chemical or safety advice. The information provided on this website is not a substitute for professional chemical consultation, safety assessment, or handling procedures. Always refer to official Safety Data Sheets (SDS) and consult with qualified professionals for specific applications and safety protocols related to formic acid.

The creators of this page are not responsible for any errors or omissions, or for any actions taken based on the information provided herein.

The Essence of Formic Acid

💡 Dive in with Flashcard Learning! 💡

What is Formic Acid? ℹ️

🧪 The Simplest Acid

🏭 Industrial Significance

👃 Sensory Properties

Natural Occurrence 🌿

🐜 Found in Nature

🍎 In Foods and Atmosphere

Historical Context 📜

⚗️ Early Isolation and Synthesis

📈 Rise in Industrial Use

Chemical and Physical Properties 📊

💧 Solubility and Structure

⚖️ Acidity and Strength

🌡️ Physical Characteristics

Chemical Reactivity 🔄

💥 Decomposition Pathways

⚡ Reducing Agent and Formyl Source

Industrial Production 🏭

⚗️ Primary Synthesis Route

💡 Alternative and Emerging Methods

🌍 Global Production Landscape

Diverse Applications 🎯

🐄 Agriculture and Animal Feed

🐝 Beekeeping and Pest Control

⚡ Energy and Chemical Storage

🧵 Industrial Processes

🔬 Analytical Chemistry

Safety and Handling ⚠️

🩹 Toxicity and Corrosivity

🩺 Health Effects

🔥 Hazard Classification

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📜 Important Notice

Dive in with Flashcard Learning!

What is Formic Acid?

The Simplest Acid

Industrial Significance

Sensory Properties

Natural Occurrence

Found in Nature

In Foods and Atmosphere

Historical Context

Early Isolation and Synthesis

Rise in Industrial Use

Chemical and Physical Properties

Solubility and Structure

Acidity and Strength

Physical Characteristics

Chemical Reactivity

Decomposition Pathways

Reducing Agent and Formyl Source

Industrial Production

Primary Synthesis Route

Alternative and Emerging Methods

Global Production Landscape

Diverse Applications

Agriculture and Animal Feed

Beekeeping and Pest Control

Energy and Chemical Storage

Industrial Processes

Analytical Chemistry

Safety and Handling

Toxicity and Corrosivity

Health Effects

Hazard Classification

Teacher's Corner

True or False?

Test Your Knowledge!

Gamer's Corner

Discover other topics to study!

References

Feedback & Support

Disclaimer

Important Notice