[11], In 2009, the worldwide capacity for producing formic acid was 720 thousand tonnes (1.6 billion pounds) per year, roughly equally divided between Europe (350 thousand tonnes or 770 million pounds, mainly in Germany) and Asia (370 thousand tonnes or 820 million pounds, mainly in China) while production was below 1 thousand tonnes or 2.2 million pounds per year in all other continents. 2010 prices ranged from around €650/tonne (equivalent to around $800/tonne) in Western Europe to $1250/tonne in the United States. In industry, this reaction is performed in the liquid phase at elevated pressure. [12], When methanol and carbon monoxide are combined in the presence of a strong base, the result is methyl formate, according to the chemical equation:[6]. In ants, formic acid is derived from serine through a 5,10-methenyltetrahydrofolate intermediate. As mentioned below, formic acid readily decomposes with concentrated sulfuric acid to form carbon monoxide. Concentrated formic acid slowly decomposes to carbon monoxide and water, leading to pressure buildup in the containing vessel. In the late 1960s, however, significant quantities became available as a byproduct of acetic acid production. Formic acid is a colorless liquid having a highly pungent, penetrating odor at room temperature.It is corrosive and flammable liquid. Nonetheless, it has specific toxic effects; the formic acid and formaldehyde produced as metabolites of methanol are responsible for the optic nerve damage, causing blindness, seen in methanol poisoning. I It is also one of the main odor-active compounds in acid-hydrolyzed soy sauce. [25], A major use of formic acid is as a preservative and antibacterial agent in livestock feed. This problem has led some manufacturers to develop energy-efficient methods of separating formic acid from the excess water used in direct hydrolysis. It is also found in the trichomes of stinging nettle (Urtica dioica). It is miscible with water and most polar organic solvents, and is somewhat soluble in hydrocarbons. Yields of up to 53% formic acid can be achieved. [citation needed]. Formic acid is named after ants which have high concentrations of the compound in their venom. The smell of formic acid, CH 2 O 2 needs to be predicted. The chemical composition is HCOOH. Some routes proceed indirectly by first treating the methyl formate with ammonia to give formamide, which is then hydrolyzed with sulfuric acid: A disadvantage of this approach is the need to dispose of the ammonium sulfate byproduct. [citation needed] This oxidative route to acetic acid is declining in importance, so that the aforementioned dedicated routes to formic acid have become more important. [41][42] Carbon monoxide free hydrogen has been generated in a very wide pressure range (1–600 bar). [29], Formic acid application has been reported to be an effective treatment for warts. [6] As of 2009[update], the largest producers are BASF, Eastman Chemical Company, LC Industrial, and Feicheng Acid Chemicals, with the largest production facilities in Ludwigshafen (200 thousand tonnes or 440 million pounds per year, BASF, Germany), Oulu (105 thousand tonnes or 230 million pounds, Eastman, Finland), Nakhon Pathom (n/a, LC Industrial), and Feicheng (100 thousand tonnes or 220 million pounds, Feicheng, China). [13][14], Formic acid can also be obtained by aqueous catalytic partial oxidation of wet biomass by the OxFA process. In hydrocarbons and in the vapor phase, it consists of hydrogen-bonded dimers rather than individual molecules. It is miscible with water and most polar organic solvents, and is somewhat soluble in hydrocarbons. [50] The principal danger from formic acid is from skin or eye contact with the concentrated liquid or vapors. In 1855, another French chemist, Marcellin Berthelot, developed a synthesis from carbon monoxide similar to the process used today. Treatment of formic acid with sulfuric acid is a convenient laboratory source of CO.[39][40]. Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH. Some formate esters are artificial flavorings and perfumes. Formic acid was first synthesized from hydrocyanic acid by the French chemist Joseph Gay-Lussac. Textbook solution for Living by Chemistry 2nd Edition Angelica M. Stacy Chapter U2 Problem 1STP. The hazards of solutions of formic acid depend on the concentration. [27][28] Use as preservative for silage and (other) animal feed constituted 30% of the global consumption in 2009. [44], An unstable formic anhydride, H(C=O)−O−(C=O)H, can be obtained by dehydration of formic acid with N,N′-dicyclohexylcarbodiimide in ether at low temperature.[45]. Formic acid has low toxicity (hence its use as a food additive), with an LD50 of 1.8 g/kg (tested orally on mice). It is soluble in most polar organic solvents. Some experiments on bacterial species have demonstrated it to be a mutagen. [8][9] The wood ants from the genus Formica can spray formic acid on their prey or to defend the nest. [18], It has been reported that formate can be formed by the electrochemical reduction of CO2 (in the form of bicarbonate) at a lead cathode at pH 8.6:[19]. Carbonous acid; Formylic acid; Hydrogen carboxylic acid; Hydroxy(oxo)methane; Metacarbonoic acid; Oxocarbinic acid; Oxomethanol, Except where otherwise noted, data are given for materials in their. [43] The co-product of this decomposition, carbon dioxide, can be rehydrogenated back to formic acid in a second step. The smell of formic acid, CH2O2 needs to be predicted. It produces burns and blisters on the skin and injures the eyes and the mucous membranes in the mouth, throat, and respiratory system. [48] Some chronic effects of formic acid exposure have been documented. Some species, including carpenter ants, spray formic acid, a caustic chemical that smells a lot like vinegar, when they feel threatened. Hydrolysis of the methyl formate produces formic acid: Efficient hydrolysis of methyl formate requires a large excess of water. Ask subject matter experts 30 homework questions each month. We know that olfactory memory is very keen. The word "formic" comes from the Latin word for ant, formica, referring to its early isolation by the distillation of ant bodies. At higher concentrations formic acid is corrosive, has a strong smell, and produces dangerous fumes. ", "UCLA Researchers Use Electricity and CO2 to Make Butanol", https://www.novapublishers.com/catalog/product_info.php?products_id=48192, "Extract of a Letter, Written by Mr. John Wray to the Publisher January 13. Not all ants sting, and not all ant stings have thesame venom, but one that is very common, and gives many ants their vinegary smell, is called formic acid. [23] The conjugate base of formic acid, formate, also occurs widely in nature. [26] In the poultry industry, it is sometimes added to feed to kill E. coli bacteria. [31][32], It is possible to use formic acid as an intermediary to produce isobutanol from CO2 using microbes[33][34][35], Formic acid is often used as a component of mobile phase in reversed-phase high-performance liquid chromatography (RP-HPLC) analysis and separation techniques for the separation of hydrophobic macromolecules, such as peptides, proteins and more complex structures including intact viruses. [20] The formate could be used as feed to modified E. coli bacteria for producing biomass. It is used as a volatile pH modifier in HPLC and capillary electrophoresis. (Some people think that the ability to smell formic acid is genetic, like asparagus, and that might be why some people are more sensitive to this particular ant smell than others.) The net reaction is thus: Another illustrative method involves the reaction between lead formate and hydrogen sulfide, driven by the formation of lead sulfide. In the presence of certain acids, including sulfuric and hydrofluoric acids, however, a variant of the Koch reaction occurs instead, and formic acid adds to the alkene to produce a larger carboxylic acid. In the presence of platinum, it decomposes with a release of hydrogen and carbon dioxide. Formic acid is readily metabolized and eliminated by the body. Formic acid was long considered a chemical compound of only minor interest in the chemical industry. [12], Formic acid is also significantly used in the production of leather, including tanning (23% of the global consumption in 2009[12]), and in dyeing and finishing textiles (9% of the global consumption in 2009[12]) because of its acidic nature. Subscribe to bartleby learn! Owing to its tendency to hydrogen-bond, gaseous formic acid does not obey the ideal gas law. In nature, formic acid is found in most ants and in stingless bees of the genus Oxytrigona.