Formic acid
General
Systematic name	methanoic acid
Other names	formic acid hydrogen carboxylic acid aminic acid
Molecular formula	CH2O2 HCOOH
SMILES	O=CO
Molar mass	46.0254 g/mol
Appearance	colourless, fuming liquid
CAS number	[64-18-6]
Properties
Density and phase	1.22 g/cm³, liquid
Solubility in water	miscible
Melting point	8.4°C (281.5 K)
Boiling point	100.8°C (373.9 K)
Acidity (pKa)	3.75
Viscosity	1.57 cP at 26°C
Structure
Molecular shape	Planar
Dipole moment	1.41 D(gas)
Hazards
MSDS	External MSDS
Main hazards	Corrosive
NFPA 704	Structural diagraim of formic acid. ... Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is defined as mass m per unit volume V. Mathematically, it is expressed as where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is the volume of the substance... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydronium ions from an acid. ... The related Category:Units of viscosity has been nominated for deletion, merging, or renaming. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation or hybridization (see also spelling differences) is the concept of mixing atomic orbitals to form new hybrid orbitals suitable for the qualitative description of atomic bonding properties. ... Something is called planar if it is made up of flat planes, or pertaining to planes. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 2 2 1
Flash point	69°C
R-phrases	R10, R35
S-phrases	S1/2, S23, S26, S45
RTECS number	LQ4900000
Supplementary data page
Structure & properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related carboxylic acids	acetic acid propionic acid
Related compounds	formaldehyde methanol
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references

Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. Its formula is HCOOH or CH₂O₂. It is an important intermediate in chemical synthesis and occurs naturally, most famously in the venom of bee and ant stings. The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... ... ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... ... ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... Propionic acid (systematically named propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2COOH. In the pure state, it is a colorless, corrosive liquid with a pungent odor. ... The chemical compound formaldehyde (also known as methanal) is a gas with a pungent smell. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ...

In nature, it is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. It is also a significant combustion product resulting from alternative fueled vehicles burning methanol (and ethanol, if contaminated with water) when mixed with gasoline. Its name comes from the Latin word for ant, formica, referring to its early isolation by the distillation of ant bodies. A chemical compound such as a salt from the neutralization of formic acid with a base, or an ester derived from formic acid, is referred to as formate (or methanoate). The formate ion has the formula HCOO⁻. Suborders Apocrita Symphyta Many families, see article Hymenoptera is one of the larger orders of Insects, comprising the sawflies, wasps, bees, and ants. ... Families Andrenidae Apidae Colletidae Halictidae Megachilidae Melittidae Stenotritidae Bee collecting pollen Bees are flying insects, closely related to wasps and ants. ... Subfamilies Aenictogitoninae Agroecomyrmecinae Amblyoponinae (incl. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... Impact of a drop of water. ... Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ... Species very many, see text Formica is a genus of ants. ... Laboratory distillation set-up using, without a fractionating column 1: Heat source 2: Still pot 3: Still head 4: Thermometer/Boiling point temperature 5: Condenser 6: Cooling water in 7: Cooling water out 8: Distillate/receiving flask 9: Vacuum/gas inlet 10: Still receiver 11: Heat control 12: Stirrer speed... A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... A magnified crystal of a salt (halite/sodium chloride) Salt covering the floor of Bad Water in Death Valley, CA, the lowest point in the US. A salt, in chemistry, is any ionic compound composed of cations (positively charged ions) and anions (negative ions) so that the product is neutral... Neutralization is a chemical reaction, also called a water forming reaction, in which an acid and a base or alkali (soluble base) react and produce a salt and water. ... Acids and bases: Acid-base reaction theories pH Self-ionization of water Buffer solutions Systematic naming Electrochemistry Acid-base extraction Acids: Strong acids Weak acids Mineral acids Organic acids Bases: Strong bases Weak bases Organic bases edit In chemistry, a base is most commonly thought of as a substance that... General formula of a carboxylate ester. ... “Multivalent” redirects here. ...

Properties

Formic acid is miscible with water and most polar organic solvents, and somewhat soluble in hydrocarbons. In hydrocarbons and in the vapor phase, it actually consists of hydrogen-bonded dimers rather than individual molecules. In the gas phase, this hydrogen-bonding results in severe deviations from the ideal gas law. Liquid and solid formic acid consists of an effectively infinite network of hydrogen-bonded formic acid molecules. The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... This article describes water from a scientific and technical perspective. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... For other uses, see Solvent (disambiguation). ... Hydrocarbons are refined at oil refineries and processed at chemical plants A hydrocarbon is a chemical compound that consists only of the elements carbon (C) and hydrogen (H). ... Snapshot from a simulation of liquid water. ... Isotherms of an ideal gas The ideal gas law is the equation of state of a hypothetical ideal gas, first stated by Benoît Paul Émile Clapeyron in 1834. ...

Formic acid shares most of the chemical properties of other carboxylic acids, although under normal conditions it will not form either an acyl chloride or an acid anhydride. Until very recently, all attempts to form either of these derivatives have resulted in carbon monoxide instead. It has now been shown that the anhydride may be produced by reaction of formyl fluoride with sodium formate at −78°C, and the chloride by passing HCl into a solution of 1-formimidazole in monochloromethane at −60°C^[1]. Heat can also cause formic acid to decompose to carbon monoxide and water. Formic acid shares some of the reducing properties of aldehydes. Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted... General Chemical Structure of an Acyl Chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. ... Acid anhydrides are chemical compounds that look like, and sometimes are, the product resulting from dehydration of an acid. ... Illustration of a redox reaction Redox (shorthand for oxidation/reduction reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... An aldehyde. ...

Formic acid is unique among the carboxylic acids in its ability to participate in addition reactions with alkenes. Formic acids and alkenes readily react to form formate esters. In the presence of certain acids, including sulfuric and hydrofluoric acids, however, a variant of the Koch reaction takes place instead, and formic acid adds to the alkene to produce a larger carboxylic acid. The chemical structure of ethylene, the simplest alkene. ... General formula of a carboxylate ester. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... Hydrofluoric acid is a highly toxic and corrosive solution of hydrogen fluoride in water. ...

Most simple formate salts are water-soluble. It has been suggested that this article or section be merged with Solution. ...

History

As early as the 15th century, some alchemists and naturalists were aware that ant hills gave off an acidic vapor. The first person to describe the isolation of this substance (by the distillation of large numbers of ants) was the English naturalist John Ray, in 1671. Ants secrete the formic acid for attack and defense purposes. Formic acid was first synthesized from hydrocyanic acid by the French chemist Joseph Gay-Lussac. In 1855, another French chemist, Marcellin Berthelot, developed a synthesis from carbon monoxide that is similar to that used today. For other uses, see Alchemy (disambiguation). ... Table of natural history, 1728 Cyclopaedia Natural history is an umbrella term for what are now usually viewed as several distinct scientific disciplines. ... Motto: (French for God and my right) Anthem: God Save the King/Queen Capital London (de facto) Largest city London Official language(s) English (de facto) Unification    - by Athelstan AD 927  Area    - Total 130,395 km² (1st in UK)   50,346 sq mi  Population    - 2006 est. ... John Ray. ... Hydrogen cyanide is a chemical compound with chemical formula H-C≡N. A solution of hydrogen cyanide in water is called hydrocyanic acid or prussic acid. ... Joseph-Louis Gay-Lussac (December 6, 1778–May 10, 1850) was a French chemist and physicist. ... Marcellin Berthelot Marcellin (or Marcelin) Pierre Eugène Berthelot (October 25, 1827 - March 18, 1907) was a French chemist and politician. ... Carbon monoxide, with the chemical formula CO, is a colourless, odourless, and tasteless gas. ...

In the chemical industry, formic acid was long considered a chemical compound of only minor industrial interest. In the late-1960s, however, significant quantities of it became available as a byproduct of acetic acid production. It now finds increasing use as a preservative and antibacterial in livestock feed. A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a fixed ratio determining the composition. ... Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ... Sheep are commonly bred as livestock. ...

Production

A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals, especially acetic acid. This production is insufficient to meet the present demand for formic acid, and some formic acid must be produced for its own sake. Acetic acid, also known as ethanoic acid, is an organic chemical compound best recognized for giving vinegar its sour taste and pungent smell. ...

When methanol and carbon monoxide are combined in the presence of a strong base, the formic acid derivative methyl formate results, according to the chemical equation Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Carbon monoxide, with the chemical formula CO, is a colourless, odourless, and tasteless gas. ... Acids and bases: Acid-base reaction theories pH Self-ionization of water Buffer solutions Systematic naming Electrochemistry Acid-base extraction Acids: Strong acids Weak acids Mineral acids Organic acids Bases: Strong bases Weak bases Organic bases edit In chemistry, a base is most commonly thought of as a substance that... Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. ... A chemical equation is a symbolic representation of a chemical reaction where the reactant entities are given on the left hand side and the product entities on the right hand side. ...

CH₃OH + CO → HCOOCH₃

In industry, this reaction is performed in the liquid phase at elevated pressure. Typical reaction conditions are 80°C and 40 atm. The most widely-used base is sodium methoxide. Hydrolysis of the methyl formate produces formic acid: Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Carbon monoxide, with the chemical formula CO, is a colourless, odourless, and tasteless gas. ... Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. ... An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. ... Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ...

HCOOCH₃ + H₂O → HCOOH + CH₃OH

Direct hydrolysis of methanol requires a large excess of water to proceed efficiently, and some producers perform it by an indirect route by first reacting the methyl formate with ammonia to produce formamide, and then hydrolyzing the formamide with sulfuric acid to produce formic acid: Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. ... Impact of a drop of water. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Impact of a drop of water. ... Ammonia is a compound with the formula NH3. ... Formamide, also known as Methanamide (IUPAC) and Carbamaldehyde, formula HCONH2 is an amide derived from formic acid. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ...

HCOOCH₃ + NH₃ → HCONH₂ + CH₃OH

HCONH₂ + H₂O + ½H₂SO₄ → HCOOH + ½(NH₄)₂SO₄

This technique has problems of its own, particularly disposing of the ammonium sulfate byproduct, so some manufacturers have recently developed energy efficient means of separating formic acid from the large excess amount of water used in direct hydrolysis. In one of these processes (used by BASF) the formic acid is removed from the water via liquid extraction with an organic base. Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. ... Ammonia is a compound with the formula NH3. ... Formamide, also known as Methanamide (IUPAC) and Carbamaldehyde, formula HCONH2 is an amide derived from formic acid. ... Methanol, also known as methyl alcohol, carbinol, wood alcohol or wood spirits, is a chemical compound with chemical formula CH3OH. It is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol (ethyl alcohol). ... Formamide, also known as Methanamide (IUPAC) and Carbamaldehyde, formula HCONH2 is an amide derived from formic acid. ... Impact of a drop of water. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... Ammonium sulphate, [NH4]2[SO4] contains 21% nitrogen as ammonia and 24% sulfur as sulfate. ... Ammonium sulphate, [NH4]2[SO4] contains 21% nitrogen as ammonia and 24% sulfur as sulfate. ... BASF may also historically refer to EMTEC, which was known as BASF for a short time after its founding. ...

In the laboratory formic acid can be obtained by heating oxalic acid in anhydrous glycerol and extraction by steam distillation. Another preparation (which must be performed under a fume hood) is the acid hydrolysis of ethyl isonitrile using HCl solution.^[1] Oxalic acid (IUPAC name: ethanedioic acid, formula C2H2O4) is a dicarboxylic acid with structure (HOOC)-(COOH). ... Glycerol, also well known as glycerin and glycerine, and less commonly as propane-1,2,3-triol, 1,2,3-propanetriol, 1,2,3-trihydroxypropane, glyceritol, and glycyl alcohol is a colorless, odorless, hygroscopic, and sweet-tasting viscous liquid. ... Hydrolysis is a chemical reaction or process in which a molecule is split into two parts by reacting with a molecule of water, which has the chemical formula H2O. One of the parts gets an OH- from the water molecule and the other part gets an H+ from the water. ... The chemical compound hydrochloric acid is the aqueous (water-based) solution of hydrogen chloride gas (HCl). ...

C₂H₅NC + 2H₂O → C₂H₅NH₂ + HCOOH

The isonitrile being obtained by reacting ethyl amine with chloroform (note that the fume hood is required because of the overpoweringly objectionable odor of the isonitrile). Impact of a drop of water. ... Ethylamine is a chemical compound with the formula CH3CH2NH2. ... Ethylamine is a chemical compound with the formula CH3CH2NH2. ... For the song Chloroform by Spoon, see A Series of Sneaks Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with formula CHCl3. ...

Uses

The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer, and so it is widely used to preserve winter feed for cattle. In the poultry industry, it is sometimes added to feed to kill salmonella bacteria. Other uses: A preservative is a natural or synthetic chemical that is added to products such as foods, pharmaceuticals, paints, biological samples, etc. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... Stacked hay in Romania A bale of grass hay weighing approximately 70 pounds, able to be managed by one person without need for mechanized equipment Close view of grass hay. ... Silage (hay) somewhere in Allschwil or Schönenbuch, near Basel, Switzerland. ... Binomial name Bos taurus Linnaeus, 1758 Cattle (often called cows in vernacular and contemporary usage, or kye as the Scots plural of cou) are domesticated ungulates, a member of the subfamily Bovinae of the family Bovidae. ... This article or section does not adequately cite its references or sources. ... Species Salmonella bongori Salmonella enterica Salmonella arizonae Salmonella enteritidis Salmonella typhi Salmonella typhimurium Salmonella is a genus of rod-shaped Gram-negative enterobacteria that causes typhoid fever, paratyphoid fever and foodborne illness. ...

• It is used to process organic latex (sap) into raw rubber.
• Beekeepers use formic acid as a miticide against the Varroa mite.
• It is of minor importance in the textile industry and for the tanning of leather.
• Some formate esters are artificial flavorings or perfumes.
• It is the active ingredient in some brands of household limescale remover.

In synthetic organic chemistry, formic acid is often used as a source of hydride ion. The Eschweiler-Clarke reaction and the Leuckart-Wallach reaction are examples of this application. It is also used as a source of hydrogen in transfer hydrogenation. Latex being collected from a tapped rubber tree Rubber is an elastic hydrocarbon polymer which occurs as a milky colloidal suspension (known as latex) in the sap of several varieties of plants. ... Beekeeping (or apiculture) is the maintenance of one or more hives of honeybees. ... Miticides are pesticides that kill mites. ... Binomial name Varroa destructor Anderson & Trueman, 2000 Varroa destructor is an external parasitic mite that attacks honey bees Apis cerana and Apis mellifera, the bumblebee Bombus pennsylvanicus, the scarab beetle Palpada vinetorum and the flower-fly Phanaeus vindex. ... Sunday textile market on the sidewalks of Karachi, Pakistan. ... Tanning is the process of conversion of putrescible skin into non putrescible leather. ... Modern leather-working tools Leather is a material created through the tanning of hides and skins of animals, primarily cattlehide. ... For the Biblical Ester, see Esther. ... Organic synthesis is the construction of organic molecules via chemical processes. ... A hydride is a compound of hydrogen with more electropositive elements. ... The Eschweiler-Clarke reaction (also called the Eschweiler-Clarke methylation) is a chemical reaction whereby a primary (or secondary) amine is methylated using excess formic acid and formaldehyde. ... The Leuckart reaction is the chemical reaction of ammonium salts of formic acid with aldehydes (or ketones) to form amines by reductive amination. ... Transfer hydrogenation is the addition of hydrogen (H2; dihydrogen in inorganic and organometallic chemistry) to a molecule from a source other than gaseous H2. ...

In the laboratory formic acid is also used as source for carbon monoxide, which is set free by the addition of sulfuric acid. Formic acid is also a source for a formyl group for example in the formylation of metylaniline to N-methylformanilide in toluene.^[2] Carbon monoxide, with the chemical formula CO, is a colourless, odourless, and tasteless gas. ... Sulfuric acid (British English: sulphuric acid), H2SO4, is a strong mineral acid. ... In organic chemistry, formyl is the radical or functional group with the formula -COH and structure - C = O | H The formyl group is the acyl of formic acid and the chief functional group of aldehydes. ... Categories: | | ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ...

Fuel cells that use modified formic acid are promising. The Formic acid fuel cell is a type of fuel cell that uses formic acid as a fuel. ...

Safety

The principal danger from formic acid is from skin or eye contact with liquid formic acid or with the concentrated vapors. Any of these exposure routes can cause severe chemical burns, and eye exposure can result in permanent eye damage. Inhaled vapors may similarly cause irritation or burns in the respiratory tract. Since carbon monoxide may be also be present in formic acid vapors, care should be taken wherever large quantities of formic acid fumes are present. The US OSHA Permissible Exposure Level (PEL) of formic acid vapor in the work environment is 5 parts per million parts of air (ppm). Carbon monoxide, with the chemical formula CO, is a colourless, odourless, and tasteless gas. ... If you are searching for the organization, click OSHA. Osha (Ligusticum porteri) is a perennial herb used for its medicinal properties. ... PEL or pel may refer to: pel, an abbreviation for pixel Permissible Exposure Limit, a legal limit defined by the Occupational Safety and Health Administration in the United States PEL, an abbreviation for Peak of Eternal Light, a location within the Solar System that is almost constantly bathed in sunlight. ... Parts per million (ppm) is a measure of concentration that is used where low levels of concentration are significant. ...

Formic acid is readily metabolized and eliminated by the body. Nonetheless, some chronic effects have been documented. Some animal experiments have demonstrated it to be a mutagen, and chronic exposure may cause liver or kidney damage. Another possibility with chronic exposure is development of a skin allergy that manifests upon re-exposure to the chemical. In biology, a mutagen (Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ... This article deals specifically with IgE-mediated hypersensitivity. ...

The hazards of solutions of formic acid depend on the concentration. The following table lists the EU classification of formic acid solutions: Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ...

Safety symbol

Image File history File links Hazard_C.svg Summary Description: The hazard symbol for corrosive substances according to directive 67/548/EWG by the European Chemicals Bureau. ... Image File history File links Hazard_C.svg Summary Description: The hazard symbol for corrosive substances according to directive 67/548/EWG by the European Chemicals Bureau. ... In chemistry, concentration is the measure of how much of a given substance there is mixed with another substance. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ...

External links

• Carbon monoxide as reagent in the formylation of aromatic compounds.
• MSDS (Material Safety Data Sheet).
• European Chemicals Bureau.
• International Chemical Safety Card 0485.
• NIOSH Pocket Guide to Chemical Hazards.
• Computational Chemistry Wiki.
• External MSDS Data Sheet.
• Formic acid pH and titration - freeware for data analysis, simulation and distribution diagram generation

• Links to external chemical sources

References

1. ^ Cohen, Julius B.: Practical Organic Chemistry MacMillan 1930
2. ^ N-methylformanilide, Organic Syntheses, Coll. Vol. 3, p.590 (1955); Vol. 20, p.66 (1940). Article