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Revision as of 07:00, 9 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit		Latest revision as of 17:07, 1 November 2024 edit undo130.113.109.180 (talk) citation addedTag: Visual edit
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			{{Redirects|Ant acid|substances that neutralize stomach acidity|antacid}}
	{{chembox
			{{short description|Simplest carboxylic acid (HCOOH)}}
			{{Use dmy dates|date=January 2022}}
			{{Chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 409743469		| verifiedrevid = 443825627
	| Name = Formic acid		| Name = Formic acid
	| ImageFile2 = formic acid 85 percent.jpg		| ImageFile2 = formic acid 85 percent.jpg
	| ImageSize2 = 120px		| ImageSize2 = 120px
	| ImageFileL1 = Ameisensäure Keilstrich.svg		| ImageFileL1 = Formic_acid.svg
			| ImageNameL1 = Skeletal structure of formic acid
	| ImageSizeL1 = 120px
			| ImageFileR1 = Formic-acid-CRC-MW-3D-balls.png
	| ImageNameL1 = Skeletal structure of formic acid
			| ImageNameR1 = 3D model of formic acid
	| ImageFileR1 = Formic-acid-CRC-MW-3D-balls.png
			| PIN = Formic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 745 | doi = 10.1039/9781849733069 | isbn = 978-0-85404-182-4| last1 = Favre | first1 = Henri A. | last2 = Powell | first2 = Warren H. }}</ref>
	| ImageSizeR1 = 120px
			| SystematicName = Methanoic acid<ref name=iupac2013 />
	| ImageNameR1 = 3D model of formic acid
			| OtherNames = {{Unbulleted list|Formylic acid|Methylic acid|Hydrogencarboxylic acid|Hydroxy(oxo)methane|Metacarbonoic acid|Oxocarbinic acid|Oxomethanol|Hydroxymethylene oxide}}
	| IUPACName = Formic acid
			|Section1={{Chembox Identifiers
	| SystematicName = Methanoic acid
			| CASNo = 64-18-6
	| OtherNames = Aminic acid<br />
			| CASNo_Ref = {{cascite|correct|CAS}}
	Formylic acid<br />
			| Beilstein = 1209246
	Hydrogen carboxylic acid<br />
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	Hydroxymethanone<br />
			| ChEBI = 30751
	Hydroxy(oxo)methane<br />
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	Metacarbonoic acid<br />
			| ChEMBL = 116736
	Oxocarbinic acid<br />
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	Oxomethanol
			| ChemSpiderID = 278
	| Section1 = {{Chembox Identifiers
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB01942
	| SMILES = C(=O)O		| DrugBank = DB01942
			| EINECS = 200-579-1
	| UNII_Ref = {{fdacite|correct|FDA}}
			| Gmelin = 1008
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 0YIW783RG1		| UNII = 0YIW783RG1
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C00058		| KEGG = C00058
			| PubChem = 284
	| InChI = 1/CH2O2/c2-1-3/h1H,(H,2,3)
			| RTECS = LQ4900000
			| SMILES = O=CO
			| InChI = 1/HCOOH/c2-1-3/h1H,(H,2,3)
	| InChIKey = BDAGIHXWWSANSR-UHFFFAOYAT		| InChIKey = BDAGIHXWWSANSR-UHFFFAOYAT
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 1S/HCOOH/c2-1-3/h1H,(H,2,3)
	| ChEMBL = 116736
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/CH2O2/c2-1-3/h1H,(H,2,3)
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = BDAGIHXWWSANSR-UHFFFAOYSA-N		| StdInChIKey = BDAGIHXWWSANSR-UHFFFAOYSA-N
			}}
	| CASNo = 64-18-6
			|Section2={{Chembox Properties
	| CASNo_Ref = {{cascite|correct|CAS}}
			| C=1 | H=2 | O=2
	| ChEBI_Ref = {{ebicite|correct|EBI}}
			| Appearance = Colorless fuming liquid
	| ChEBI = 30751
			| Odor = Pungent, penetrating
	| PubChem = 284
			| Density = 1.220{{nbsp}}g/mL
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| Solubility = Miscible
	| ChemSpiderID = 278
			| SolubleOther = Miscible with ], ], ], ], ], ] <br /> Partially soluble in ], ], ]s
	| RTECS = LQ4900000
	| ATCvet = yes		| MeltingPtC = 8.4
			| BoilingPtC = 100.8
	| ATCCode_prefix = P53
			| pKa = 3.745<ref>{{cite book |last1=Smith |first1=Robert M. |last2=Martell |first2=Arthur E. |title=Critical Stability Constants Volume 6: Second Supplement |date=1989 |publisher=Plenum Press |location=New York |isbn=0-306-43104-1 |page=299}}</ref>
	| ATCCode_suffix = AG01
			| ConjugateBase = ]
	}}
			| Viscosity = 1.57{{nbsp}}c] at 268&nbsp;°C
	| Section2 = {{Chembox Properties
			| LogP = −0.54
	| C = 1 | H = 2 | O =2
			| RefractIndex = 1.3714 (20&nbsp;°C)
	| Appearance = Colorless liquid
			| MagSus = {{val|-19.90|e=-6|u=cm3/mol}}
	| Density = 1.22 g/mL, liquid
			| VaporPressure = 35{{nbsp}}mmHg (20&nbsp;°C)<ref name=PGCH/>
	| Solubility = Miscible
			}}
	| MeltingPtC = 8.4
			|Section3={{Chembox Structure
	| BoilingPtC = 100.8
			| MolShape = ]
	| pKa = 3.77 <ref>Brown, H. C. et al., in Braude, E. A. and Nachod, F. C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref>
	| Viscosity = 1.57 c] at 26 °C		| Dipole = 1.41{{nbsp}}] (gas)}}
			|Section5={{Chembox Thermochemistry
	}}
			| DeltaHf = −425.0{{nbsp}}kJ/mol
	| Section3 = {{Chembox Structure
			| DeltaHc = −254.6{{nbsp}}kJ/mol
	| MolShape = ]
			| Entropy = 131.8{{nbsp}}J/mol&nbsp;K
	| Dipole = 1.41 ](gas)
	}}		}}
	| Section7 = {{Chembox Hazards		|Section6={{Chembox Pharmacology
			| ATCvet = yes
	| ExternalMSDS =
			| ATCCode_prefix = P53
	| MainHazards = Corrosive; irritant;<br />sensitizer.
	| NFPA-H = 3		| ATCCode_suffix = AG01
			}}
	| NFPA-F = 2
			|Section7={{Chembox Hazards
	| NFPA-R = 1
			| ExternalSDS =
	| FlashPt = 69 °C (156 °F)
			| MainHazards = Corrosive; irritant;<br />sensitizer
	| RPhrases = {{R10}} {{R35}}
			| NFPA-H = 3
	| SPhrases = {{S1/2}} {{S23}} {{S26}} {{S45}}
			| NFPA-F = 2
	}}
			| NFPA-R = 0
	| Section8 = {{Chembox Related
			| FlashPtC = 69
	| Function = ]s
			| AutoignitionPtC = 601
	| OtherFunctn = ]<br/>]
			| ExploLimits = 14{{ndash}}34%{{citation needed|date=March 2015}}<br /> 18{{ndash}}57% (90% solution)<ref name=PGCH/>
	| OtherCpds = ]<br/>]}}
			| GHSPictograms = {{GHS02}} {{GHS05}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|314}}
			| PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}}
			| LD50 = 700{{nbsp}}mg/kg (mouse, oral), 1100{{nbsp}}mg/kg (rat, oral), 4000{{nbsp}}mg/kg (dog, oral)<ref name=IDLH>{{cite web |url = https://www.cdc.gov/niosh/idlh/64186.html |title = Formic acid |work = Immediately Dangerous to Life or Health Concentrations (IDLH) |publisher = National Institute for Occupational Safety and Health |date = 4 December 2014 |access-date = 26 March 2015}}</ref>
			| PEL = TWA 5{{nbsp}}ppm (9{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0296}}</ref>
			| IDLH = 30{{nbsp}}ppm<ref name=PGCH/>
			| REL = TWA 5{{nbsp}}ppm (9{{nbsp}}mg/m<sup>3</sup>)<ref name=PGCH/>
			| LC50 = 7853{{nbsp}}ppm (rat, 15{{nbsp}}min)<br />3246{{nbsp}}ppm (mouse, 15{{nbsp}}min)<ref name=IDLH/>
			}}
			|Section8={{Chembox Related
			| OtherFunction_label = ]s
			| OtherFunction = ]<br />]
			| OtherCompounds = ]<br />]}}
	}}		}}
	'''Formic acid''' (also called '''methanoic acid''') is the simplest ]. Its ] is ]]]OH or HCO<sub>2</sub>H. It is an important intermediate in ] and occurs naturally, most notably in the ] of ] and ]. In fact, its name comes from the ] word for ant, '']'', referring to its early isolation by the ] of ant bodies. ]s, salts, and the anion derived from formic acid are referred to as ]s.		'''Formic acid''' ({{ety|la|formica|]}}), ] '''methanoic acid''', is the simplest ], and has the ] HCOOH and structure {{chem2|H\sC(\dO)\sO\sH}}. It is an important intermediate in ] and occurs naturally, most notably in some ants. ]s, ] and the ] derived from formic acid are called ]s. Industrially, formic acid is produced from ].<ref>{{Cite web |title=Formic acid |url=https://www.acs.org/molecule-of-the-week/archive/f/formic-acid.html |access-date=2023-11-21 |website=American Chemical Society |language=en}}</ref>
			==Natural occurrence==
			{{See also|Insect defenses}}
			Formic acid is found naturally in insects, weeds, fruits and vegetables, and forest emissions. It appears in most ] and in ]s of the genus '']''.<ref>{{cite journal |doi=10.1097/ACI.0b013e328339f325 |pmid=20445444 |title=Ant venoms |journal=Current Opinion in Allergy and Clinical Immunology |volume=10 |issue=4 |pages=342–6 |year=2010 |last1=Hoffman |first1=Donald R |s2cid=4999650 }}</ref><ref>{{cite journal| pmid=24302133 | doi=10.1007/BF01020539 | volume=13 | issue=5 | title=Formic acid in caustic cephalic secretions of stingless bee,Oxytrigona (Hymenoptera: Apidae) | year=1987 | journal=J Chem Ecol | pages=1079–86 | last1 = Roubik | first1 = DW | last2 = Smith | first2 = BH | last3 = Carlson | first3 = RG| s2cid=30511107 }}</ref> ] from the genus '']'' can spray formic acid on their prey or to defend the nest. The ] (''Cerura vinula'') will spray it as well when threatened by predators. It is also found in the ]s of ] (''Urtica dioica''). Apart from that, this acid is incorporated in many fruits such as pineapple (0.21 mg per 100 g), apple (2 mg per 100 g) and kiwi (1 mg per 100 g), as well as in many vegetables, namely onion (45 mg per 100 g), eggplant (1.34 mg per 100 g) and, in extremely low concentrations, cucumber (0.11 mg per 100 g).<ref>{{cite journal| pmc=3349212 | pmid=22593694 | doi=10.1100/2012/564367 | volume=2012 | title=Phenolic compounds analysis of root, stalk, and leaves of nettle | year=2012 | journal=ScientificWorldJournal | page=564367 | last1 = Otles | first1 = S | last2 = Yalcin | first2 = B | doi-access=free }}</ref> Formic acid is a naturally occurring component of the ] primarily due to forest emissions.<ref>{{cite journal |doi=10.1029/91GL01565 |title=Emission of formic and acetic acids from tropical Savanna soils |journal=Geophysical Research Letters |volume=18 |issue=9 |pages=1707–10 |year=1991 |last1=Sanhueza |first1=Eugenio |last2=Andreae |first2=Meinrat O |bibcode=1991GeoRL..18.1707S }}</ref>
			==History==
			As early as the 15th century, some ] and ] were aware that ant hills give 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 ], in 1671.<ref>{{cite journal |doi=10.1098/rstl.1670.0052 |title=Extract of a Letter, Written by Mr John Wray to the Publisher January 13. 1670. Concerning Some Un-Common Observations and Experiments Made with an Acid Juyce to be Found in Ants |journal=Philosophical Transactions of the Royal Society of London |volume=5 |issue=57–68 |pages=2063–2066 |year=1670 |last1=Wray |first1=J |bibcode=1670RSPT....5.2063W |doi-access=free }}</ref><ref>{{cite book | url = https://books.google.com/books?id=i1eS9LAe3PsC&pg=PA51 | title = History of the process and present state of animal chemistry | last1 = Johnson | first1 = W. B. | year = 1803}}</ref> Ants secrete the formic acid for attack and defense purposes. Formic acid was first synthesized from ] by the French chemist ]. In 1855, another French chemist, ], developed a synthesis from ] similar to the process used today.{{cn|date=June 2024}}
			Formic acid was long considered a ] of only minor interest in the chemical industry. In the late 1960s, significant quantities became available as a byproduct of ] production. It now finds increasing use as a preservative and antibacterial in ] feed.{{cn|date=June 2024}}
	==Properties==		==Properties==
			]
	Formic acid is a colorless liquid having a highly pungent, penetrating odor<ref>.</ref> at room temperature. It is ] with ] and most polar ] ]s, and is somewhat soluble in ]s. In hydrocarbons and in the vapor phase, it consists of ]ed dimers rather than individual molecules.<ref name=Ullmann_2009>Werner Reutemann and Heinz Kieczka “Formic Acid” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a12_013}}</ref><ref name=Balabin_2009>{{cite journal |journal=] |volume = 113 |issue = 17 |page = 4910 |doi=10.1021/jp9002643 |title=Polar (Acyclic) Isomer of Formic Acid Dimer: Gas-Phase Raman Spectroscopy Study and Thermodynamic Parameters |year=2009 |author=Roman M. Balabin |pmid=19344174}}</ref> Owing to its tendency to hydrogen-bond, gaseous formic acid does not obey the ].<ref name=Balabin_2009/> Solid formic acid (two ]) consists of an effectively endless network of hydrogen-bonded formic acid molecules. This relatively complicated compound also forms a low-boiling ] with water (22.4%) and liquid formic acid also tends to supercool.
			Formic acid is a colorless liquid having a pungent, penetrating odor<ref>{{cite web|url=https://www.osha.gov/chemicaldata/chemResult.html?recNo=468|title=OSHA Occupational Chemical Database – Occupational Safety and Health Administration|website=osha.gov|access-date=17 April 2015|archive-date=29 April 2021|archive-url=https://web.archive.org/web/20210429045534/https://www.osha.gov/chemicaldata/chemResult.html?recNo=468|url-status=dead}}</ref> at room temperature, comparable to the related ]. Formic acid is about ten times stronger than ].{{cn|date=June 2024}}
			It is ] with water and most polar ] ]s, and is somewhat soluble in ]s. In hydrocarbons and in the vapor phase, it consists of ]ed ] rather than individual molecules.<ref name=Ullmann_2009>{{cite book |doi=10.1002/14356007.a12_013 |chapter=Formic Acid |title=Ullmann's Encyclopedia of Industrial Chemistry |year=2000 |last1=Reutemann |first1=Werner |last2=Kieczka |first2=Heinz |isbn=978-3-527-30673-2 }}</ref><ref name=Balabin_2009>{{cite journal |doi=10.1021/jp9002643 |pmid=19344174 |title=Polar (Acyclic) Isomer of Formic Acid Dimer: Gas-Phase Raman Spectroscopy Study and Thermodynamic Parameters |journal=The Journal of Physical Chemistry A |volume=113 |issue=17 |pages=4910–8 |year=2009 |author= Roman M. Balabin |bibcode=2009JPCA..113.4910B }}</ref> Owing to its tendency to hydrogen-bond, gaseous formic acid does not obey the ].<ref name=Balabin_2009/> Solid formic acid, which can exist in either of two ], consists of an effectively endless network of hydrogen-bonded formic acid molecules. Formic acid forms a high-boiling ] with water (107.3&nbsp;°C; 77.5% formic acid). Liquid formic acid tends to ].
	==Natural occurrence==
			<!--Please leave the clear left template in, as the image file for this section forces the next section's title to improperly format-->{{clear|left}}
	:''See also ]''
			==Chemical reactions==
	In nature, it is found in the ] and ] of many ] of the order ], mainly ants. Because of its abundance in their diet, ]s (unlike most mammals) do not produce ] for their ].<ref> at the Natural History Collection of the ]</ref>
			===Decomposition===
			Formic acid readily decomposes by dehydration in the presence of concentrated ] to form ] and water:
			:HCO<sub>2</sub>H → H<sub>2</sub>O + CO
			Treatment of formic acid with sulfuric acid is a convenient laboratory source of CO.<ref name="koch">{{cite journal |doi=10.15227/orgsyn.044.0001 |title=1-Adamantanecarboxylic Acid |journal=Organic Syntheses |date=1964 |volume=44 |page=1|first1=H.|last1=Koch|first2=W.|last2=Haaf }}</ref> <ref name="coleman">{{OrgSynth|title=''p''-Tolualdehyde|author=Coleman, G. H.|author2=Craig, David|volume=12|pages=80|year=1932|doi=10.15227/orgsyn.012.0080}}</ref>
			In the presence of ], it decomposes with a release of ] and ].
			:HCO<sub>2</sub>H → H<sub>2</sub> + CO<sub>2</sub>
			Soluble ] catalysts are also effective for producing carbon monoxide-free hydrogen.<ref name="Fellay2008">{{cite journal |doi=10.1002/anie.200800320 |pmid=18393267 |title=A Viable Hydrogen-Storage System Based on Selective Formic Acid Decomposition with a Ruthenium Catalyst |journal=Angewandte Chemie International Edition |volume=47 |issue=21 |year=2008 |last1=Fellay |first1=Céline |last2=Dyson |first2=Paul J. |last3=Laurenczy |first3=Gábor |pages=3966–8}}</ref>
			===Reactant===
			Formic acid shares most of the chemical properties of other ]s. Because of its high acidity, solutions in alcohols form esters spontaneously; in ]s of formic acid, it self-catalyzes the reaction and no additional acid catalyst is needed.<ref>{{cite book |last1=Furniss |first1=Brian S. |last2=Hannaford |first2=Antony, J. |last3=Smith |first3=Peter W. G. |last4=Tatchell |first4=Austin S. |edition=5th |year=1989 |title=Vogel's Textbook of Practical Organic Chemistry |publisher=Longman Scientific & Technical |page=696, 701 |isbn=978-0582462366}}</ref> Formic acid shares some of the ] properties of ]s, reducing solutions of metal oxides to their respective metal.<ref>{{Cite book|last1=Ozawa|first1=Naoto|last2=Okubo|first2=Tatsuo|last3=Matsuda|first3=Jun|last4=Sakai|first4=Tatsuo|title=2016 11th International Microsystems, Packaging, Assembly and Circuits Technology Conference (IMPACT) |chapter=Observation and analysis of metal oxide reduction by formic acid for soldering |date=October 2016|chapter-url=https://ieeexplore.ieee.org/document/7799990|pages=148–151|doi=10.1109/IMPACT.2016.7799990|isbn=978-1-5090-4769-7|s2cid=32545113}}</ref>
			Formic acid is a source for a ] group for example in the ] of ] to ''N''-methylformanilide in ].<ref>{{OrgSynth | title = ''N''-Methylformanilide | collvol = 3 | collvolpages = 590 | year = 1955 | prep = cv3p0590 | authorlink=Louis Fieser |author=L. F. Fieser |author2=J. E. Jones}}</ref>
			In ], formic acid is often used as a source of ] ion, as in the ]:
			]
			It is used as a source of hydrogen in ], as in the ] to make ]s, and (in aqueous solution or in its ] with ]) for hydrogenation of ]s.<ref name="Zhou2012">{{cite journal | last=Zhou | first=Xiaowei | display-authors=etal | title=Varying the ratio of formic acid to triethylamine impacts on asymmetric transfer hydrogenation of ketones | journal=Journal of Molecular Catalysis A: Chemical | volume=357 | year=2012 | issn=1381-1169 | doi=10.1016/j.molcata.2012.02.002 | pages=133–140}}</ref>
			===Addition to alkenes===
			Formic acid is unique among the carboxylic acids in its ability to participate in addition reactions with ]s. Formic acids and alkenes readily react to form formate ]s. In the presence of certain acids, including ] and ]s, however, a variant of the ] occurs instead, and formic acid adds to the alkene to produce a larger carboxylic acid.<ref>{{cite journal |doi=10.1002/cber.19660990410 |title=Die Synthese sekundärer Carbonsäuren nach der Ameisensäure-Methode |journal=Chemische Berichte |volume=99 |issue=4 |pages=1149–52 |year=1966 |last1=Haaf |first1=Wolfgang }}</ref>
			===Formic acid anhydride===
			An unstable ], H(C=O)−O−(C=O)H, can be obtained by dehydration of formic acid with ] in ether at low temperature.<ref name=gwu>{{cite journal |doi=10.1021/j100021a022 |title=Formic Anhydride in the Gas Phase, Studied by Electron Diffraction and Microwave and Infrared Spectroscopy, Supplemented with Ab-Initio Calculations of Geometries and Force Fields |journal=The Journal of Physical Chemistry |volume=99 |issue=21 |pages=8589–98 |year=1995 |last1=Wu |first1=G |last2=Shlykov |first2=S |last3=Van Alseny |first3=F. S |last4=Geise |first4=H. J |last5=Sluyts |first5=E |last6=Van Der Veken |first6=B. J }}</ref>
	==Production==		==Production==
	In 2009, the worldwide capacity for producing this compound was 720,000 tonnes/annum, with production capacity roughly equally divided between Europe (350,000, mainly in Germany) and Asia (370,000, mainly in China), while production was below 1000 tonnes/annum in all other continents.<ref name=CEH>{{cite web|url=http://www.sriconsulting.com/CEH/Public/Reports/659.2000/|title=CEH Marketing Research Report: FORMIC ACID|author=S.N. Bizzari and M. Blagoev|work|date=june 2010|work=Chemical Economics Handbook|publisher=SRI consulting|accessdate=July 2011}}</ref> It is commercially available in solutions of various concentrations between 85 and 99 w/w %.<ref name = Ullmann_2009/> As of 2009, the largest producers are ], ] and ], with the largest production facilities in ] (200,000 tonnes/annum, BASF, Germany), ] (105,000, Kemira, Finland) and ] (100,000, Feicheng, China). 2010 Prices ranged from circa € 650/tonne in Western Europe and $ 1250/tonne in the United States.<ref name=CEH/>		In 2009, the worldwide capacity for producing formic acid was {{convert|720|e3t|e9lb|abbr=off}} per year, roughly equally divided between Europe ({{convert|350|e3t|e6lb|abbr=off|disp=or}}, mainly in Germany) and Asia ({{convert|370|e3t|e6lb|abbr=off|disp=or}}, mainly in China) while production was below {{convert|1|e3t|e6lb|abbr=off|disp=or}} per year in all other continents.<ref name=CEH>{{cite web|url=http://www.sriconsulting.com/CEH/Public/Reports/659.2000/|title=CEH Marketing Research Report: FORMIC ACID|author1=S. N. Bizzari |author2=M. Blagoev |date=June 2010|work=Chemical Economics Handbook|publisher=SRI consulting |archive-url=https://web.archive.org/web/20110914202313/http://www.sriconsulting.com/CEH/Public/Reports/659.2000/ |archive-date=14 September 2011}}</ref> It is commercially available in solutions of various concentrations between 85 and 99 w/w %.<ref name = Ullmann_2009/> {{As of|2009}}, the largest producers are ], ], ], and ], with the largest production facilities in ] ({{convert|200|e3t|e6lb|abbr=off|disp=or}} per year, BASF, Germany), ] ({{convert|105|e3t|e6lb|abbr=off|disp=or}}, Eastman, Finland), ] (n/a, LC Industrial), and ] ({{convert|100|e3t|e6lb|abbr=off|disp=or}}, Feicheng, China). 2010 prices ranged from around €650/tonne (equivalent to around $800/tonne) in Western Europe to $1250/tonne in the United States.<ref name=CEH/>
	===From methyl formate and formamide===		===From methyl formate and formamide===
	When ] and ] are combined in the presence of a strong ], the formic acid derivative ] results, according to the ]:<ref name=Ullmann_2009/>		When ] and ] are combined in the presence of a strong ], the result is ], according to the ]:<ref name=Ullmann_2009/>
	:CH<sub>3</sub>OH + CO → HCO<sub>2</sub>CH<sub>3</sub>		:CH<sub>3</sub>OH + CO → HCO<sub>2</sub>CH<sub>3</sub>
	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 ]. ] of the methyl formate produces formic acid:		In industry, this reaction is performed in the liquid phase at elevated pressure. Typical reaction conditions are 80&nbsp;°C and 40 atm. The most widely used base is ]. ] of the methyl formate produces formic acid:
	:HCO<sub>2</sub>CH<sub>3</sub> + H<sub>2</sub>O → HCO<sub>2</sub>H + CH<sub>3</sub>OH		:HCO<sub>2</sub>CH<sub>3</sub> + H<sub>2</sub>O → HCOOH + CH<sub>3</sub>OH
	Efficient hydrolysis of methyl formate requires a large excess of water. Some routes proceed indirectly by first treating the methyl formate with ] to give ], which is then hydrolyzed with ]:		Efficient hydrolysis of methyl formate requires a large excess of water. Some routes proceed indirectly by first treating the methyl formate with ] to give ], which is then hydrolyzed with ]:
	:HCO<sub>2</sub>CH<sub>3</sub> + NH<sub>3</sub> → HC(O)NH<sub>2</sub> + CH<sub>3</sub>OH		:HCO<sub>2</sub>CH<sub>3</sub> + NH<sub>3</sub> → HC(O)NH<sub>2</sub> + CH<sub>3</sub>OH
	:2 HC(O)NH<sub>2</sub> + 2 H<sub>2</sub>O + H<sub>2</sub>SO<sub>4</sub> → 2HCO<sub>2</sub>H + (NH<sub>4</sub>)<sub>2</sub>SO<sub>4</sub>		:2 HC(O)NH<sub>2</sub> + 2H<sub>2</sub>O + H<sub>2</sub>SO<sub>4</sub> → 2HCO<sub>2</sub>H + (NH<sub>4</sub>)<sub>2</sub>SO<sub>4</sub>
	This approach suffers from the need to dispose of the ] byproduct. This problem has led some manufacturers to develop energy efficient means for separating formic acid from the large excess amount of water used in direct hydrolysis. In one of these processes (used by ]) the formic acid is removed from the water via ] with an organic base.		A disadvantage of this approach is the need to dispose of the ] byproduct. This problem has led some manufacturers to develop energy-efficient methods of separating formic acid from the excess water used in direct hydrolysis. In one of these processes, used by ], the formic acid is removed from the water by ] with an organic base.{{citation needed|date=November 2017}}
	===By-product of acetic acid production===		===Niche and obsolete chemical routes===
			====By-product of acetic acid production====
	A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals. At one time, ] was produced on a large scale by oxidation of alkanes, via a process that cogenerates significant formic acid. This oxidative route to acetic acid is declining in importance, so that the aforementioned dedicated routes to formic acid have become more important.
			A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals. At one time, ] was produced on a large scale by oxidation of ]s, by a process that cogenerates significant formic acid.<ref name=Ullmann_2009/> This oxidative route to acetic acid has declined in importance so that the aforementioned dedicated routes to formic acid have become more important.{{cn|date=June 2024}}
	===Hydrogenation of carbon dioxide===		====Hydrogenation of carbon dioxide====
	The catalytic hydrogenation of CO<sub>2</sub> has long been studied. This reaction can be conducted homogeneously.<ref>P. G. Jessop, in ''Handbook of Homogeneous Hydrogenation'' (Eds.: J. G. de Vries, C. J. Elsevier), Wiley-VCH, Weinheim, Germany, '''2007''', pp. 489–511.</ref><ref>{{cite journal | author = P. G. Jessop, F. Joó, C.-C. Tai | title = Recent advances in the homogeneous hydrogenation of carbon dioxide | journal = ] | volume = 248 | page = 2425 | year = 2004 | doi = 10.1016/j.ccr.2004.05.019}}</ref>		The catalytic ] of ] to formic acid has long been studied. This reaction can be conducted homogeneously.<ref>{{Cite book | author = P. G. Jessop | title = Handbook of Homogeneous Hydrogenation | editor = J. G. de Vries, C. J. Elsevier | publisher = Wiley-VCH | location = Weinheim, Germany | date = 2007 | pages = 489–511}}</ref><ref>{{cite journal |doi=10.1016/j.ccr.2004.05.019 |title=Recent advances in the homogeneous hydrogenation of carbon dioxide |journal=Coordination Chemistry Reviews |volume=248 |issue=21–24 |pages=2425 |year=2004 |last1=Jessop |first1=Philip G |last2=Joó |first2=Ferenc |last3=Tai |first3=Chih-Cheng }}</ref><ref>{{Cite web |last=Sampson |first=Joanna |date=2 August 2020 |title=Wireless device makes clean fuel from sunlight, CO2 and water |url=https://www.gasworld.com/wireless-device-makes-clean-fuel-from-sunlight-co2-and-water-/2019694.article |access-date=2020-08-26 |website=Gasworld |language=en}}</ref>
	===Laboratory methods===
	In the laboratory, formic acid can be obtained by heating ] in anhydrous ] and extraction by steam distillation. Another preparation (which must be performed under a fume hood) is the acid ] of ethyl isonitrile (C<sub>2</sub>H<sub>5</sub>NC) using ] solution.<ref name="cohen">Cohen, Julius B.: ''Practical Organic Chemistry'' MacMillan 1930</ref>
	:C<sub>2</sub>H<sub>5</sub>NC + 2 H<sub>2</sub>O → C<sub>2</sub>H<sub>5</sub>NH<sub>2</sub> + HCO<sub>2</sub>H
	The isonitrile can be obtained by reacting ] with ] (note that the fume hood is required because of the overpoweringly objectionable odor of the ]).
			====Oxidation of biomass====
	==Uses==
			Formic acid can also be obtained by aqueous catalytic partial oxidation of wet biomass by the ].<ref>{{cite journal |doi=10.1039/C1GC15434F |title=Selective catalytic conversion of biobased carbohydrates to formic acid using molecular oxygen |journal=Green Chemistry |volume=13 |issue=10 |pages=2759 |year=2011 |last1=Wölfel |first1=Rene |last2=Taccardi |first2=Nicola |last3=Bösmann |first3=Andreas |last4=Wasserscheid |first4=Peter |s2cid=97572039 }}</ref><ref>{{cite journal |doi=10.1039/C2EE21428H |title=Selective oxidation of complex, water-insoluble biomass to formic acid using additives as reaction accelerators |journal=Energy & Environmental Science |volume=5 |issue=7 |pages=7956 |year=2012 |last1=Albert |first1=Jakob |last2=Wölfel |first2=Rene |last3=Bösmann |first3=Andreas |last4=Wasserscheid |first4=Peter |s2cid=93224286 }}</ref> A ] polyoxometalate (H<sub>5</sub>PV<sub>2</sub>Mo<sub>10</sub>O<sub>40</sub>) is used as the homogeneous catalyst to convert sugars, wood, waste paper, or cyanobacteria to formic acid and CO<sub>2</sub> as the sole byproduct. Yields of up to 53% formic acid can be achieved.{{Citation needed|date=November 2018}}
	A major use of formic acid is as a ] and ] agent in livestock feed. In Europe, silage is applied on ] (including freh hay) to promote the fermentation of ] and to suppress the formation of ]; it also allows fermentation to occur quickly, and at a lower temperature, reducing the loss of nutritional value.<ref name = Ullmann_2009/> Formic acid 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 ].{{Citation needed|date=November 2010}} In the ] industry, it is sometimes added to feed to kill '']'' bacteria.<ref>{{cite journal | author = Griggs, J. P. | author2 = J | title = Alternatives to Antibiotics for Organic Poultry Production | url = http://japr.fass.org/cgi/content/abstract/14/4/750 | journal = The Journal of Applied Poultry Research | volume = 14 | issue = 4 | page = 750 | year = 2005}}</ref><ref>{{cite journal | doi = 10.3382/japr.2006-00116 | last1 = Garcia | first1 = V. | last2 = Catala-Gregori | first2 = P. | last3 = Hernandez | first3 = F. | last4 = Megias | first4 = M. D. | last5 = Madrid | first5 = J. | title = Effect of Formic Acid and Plant Extracts on Growth, Nutrient Digestibility, Intestine Mucosa Morphology, and Meat Yield of Broilers | url = http://japr.fass.org/cgi/content/full/16/4/555 | journal = The Journal of Applied Poultry Research | volume = 16 | page = 555 | year = 2007 | issue=4}}</ref> Use as preservative for silage and (other) animal feed constituted 30% of the global consumption in 2009.<ref name=CEH/>
			====Laboratory methods====
	Formic acid is also significantly used in the production of leather -incl. ]- (23% of the global consumption in 2009<ref name=CEH/>) and in dying and finishing of textile (9% of the global consumption in 2009<ref name=CEH/>) because of its acidic nature. Use as a coagulant in the ]<ref name = Ullmann_2009/> constituted in 2009 6% of the global consumption.<ref name=CEH/>
			In the laboratory, formic acid can be obtained by heating ] in ] followed by steam distillation.<ref name="chattaway">{{cite journal |doi=10.1039/CT9140500151 |title=XX.—Interaction of glycerol and oxalic acid |journal=] |volume=105 |pages=151–6 |year=1914 |last1=Chattaway |first1=Frederick Daniel |hdl=2027/mdp.39015067135775 |url=https://zenodo.org/record/2046509 }}</ref> Glycerol acts as a catalyst, as the reaction proceeds through a glyceryl oxalate intermediate. If the reaction mixture is heated to higher temperatures, ] results. The net reaction is thus:
			:C<sub>2</sub>O<sub>4</sub>H<sub>2</sub> → HCO<sub>2</sub>H + CO<sub>2</sub><!--esoteric and not useful to anyone: Another preparation is the acid ] of ethyl isonitrile (C<sub>2</sub>H<sub>5</sub>NC) using ] solution.<ref name="cohen">{{Cite book | author = Cohen, Julius B. | title = Practical Organic Chemistry | publisher = MacMillan | date = 1930}}</ref>
			:C<sub>2</sub>H<sub>5</sub>NC + 2 H<sub>2</sub>O → C<sub>2</sub>H<sub>5</sub>NH<sub>2</sub> + HCO<sub>2</sub>H
			The isonitrile can be obtained by reacting ] with ] (note that the fume hood is required because of the overpoweringly objectionable odor of the ]).-->
			Another illustrative method involves the reaction between ] and ], driven by the formation of ].<ref>{{Cite book | author = Arthur Sutcliffe | date = 1930 | title = Practical Chemistry for Advanced Students | edition = 1949 | publisher = John Murray | location = London}}</ref>
			:Pb(HCOO)<sub>2</sub> + H<sub>2</sub>S → 2HCOOH + PbS
			====Electrochemical production====
	Formic acid is also used in place of mineral acids for various cleaning products,<ref name =Ullmann_2009/> such as ] remover and ]. Some formate ] are artificial flavorings or perfumes. ]s use formic acid as a ] against the tracheal mite ('']'') and the ].<ref>http://www.biobees.com/library/pesticides_GM_threats/miticides_varroa_acarapis.pdf</ref> The use of ] is also under investigation.{{Citation needed|date=July 2011}}
			Formate is formed by the ] of CO<sub>2</sub> (in the form of ]) at a ] ] at pH 8.6:<ref>{{cite journal |display-authors=etal|last1=B. Innocent |title=Electro-reduction of carbon dioxide to formate on lead electrode in aqueous medium |journal=Journal of Applied Electrochemistry |date=Feb 2009 |doi=10.1007/s10800-008-9658-4 |volume=39 |issue=2 |pages=227–232|s2cid=98437382 }}</ref>
			:{{chem|HCO|3|-}} + {{chem|H|2|O}} + 2e<sup>−</sup> → {{chem|HCO|2|-}} + 2{{Chem|OH|-}}
			or
			:{{chem|CO|2}} + {{chem|H|2|O}} + 2e<sup>−</sup> → {{chem|HCO|2|-}} + {{Chem|OH|-}}
			If the feed is {{chem|CO|2}} and oxygen is evolved at the anode, the total reaction is:
			:{{CO2}} + {{chem|OH|-}} → {{chem|HCO|2|-}} + 1/2 {{O2}}
	===Laboratory use===		===Biosynthesis===
			Formic acid is named after ants which have high concentrations of the compound in their venom, derived from ] through a ] intermediate.<ref>{{cite journal|last1=Hefetz|first1=Abraham|last2=Blum|first2=Murray|title=Biosynthesis of formic acid by the poison glands of formicine ants|journal=Biochimica et Biophysica Acta (BBA) - General Subjects|date=1 November 1978|volume=543|issue=4|pages=484–496|doi=10.1016/0304-4165(78)90303-3|pmid=718985}}</ref> The conjugate base of formic acid, formate, also occurs widely in nature. An ] for formic acid in body fluids, designed for determination of formate after methanol poisoning, is based on the reaction of formate with bacterial ].<ref>{{cite journal |doi=10.1016/0006-2944(75)90147-7 |pmid=1 |title=Formate assay in body fluids: Application in methanol poisoning |journal=Biochemical Medicine |volume=13 |issue=2 |pages=117–26 |year=1975 |last1=Makar |first1=A.B |last2=McMartin |first2=K.E |last3=Palese |first3=M |last4=Tephly |first4=T.R }}</ref>
	Formic acid is a source for a ] group for example in the ] of methylaniline to N-methylformanilide in ].<ref>{{OrgSynth | title = ''N''-Methylformanilide | collvol = 3 | collvolpages = 590 | year = 1955 | prep = cv3p0590 | author = ] and J. E. Jones }}</ref> In ], formic acid is often used as a source of ] ion. The ] and the ] are examples of this application. It, or more commonly its azeotrope with ], is also used as a source of hydrogen in ].
			== Uses ==
	Like ] and ], formic acid is commonly used as a volatile pH modifier in ] and ].
			===Agriculture===
			A major use of formic acid is as a ] and ] agent in livestock feed. It arrests certain decay processes and causes the feed to retain its nutritive value longer,
			In Europe, it is applied on ], including fresh hay, to promote the fermentation of ] and to suppress the formation of ]; it also allows fermentation to occur quickly, and at a lower temperature, reducing the loss of nutritional value.<ref name = Ullmann_2009/> It is widely used to preserve winter feed for ],<ref>, Maria M. Theron, J. F. Rykers Lues</ref> and is sometimes added to ] feed to kill '']'' bacteria.<ref>{{cite journal |doi=10.1093/japr/14.4.750 |title=Alternatives to Antibiotics for Organic Poultry Production |journal=The Journal of Applied Poultry Research |volume=14 |issue=4 |pages=750 |year=2005 |last1=Griggs |first1=J. P |last2=Jacob |first2=J. P |doi-access=free }}</ref><ref>{{cite journal |doi=10.3382/japr.2006-00116 |title=Effect of Formic Acid and Plant Extracts on Growth, Nutrient Digestibility, Intestine Mucosa Morphology, and Meat Yield of Broilers |journal=The Journal of Applied Poultry Research |volume=16 |issue=4 |pages=555 |year=2007 |last1=Garcia |first1=V |last2=Catala-Gregori |first2=P |last3=Hernandez |first3=F |last4=Megias |first4=M. D |last5=Madrid |first5=J |doi-access=free }}</ref> Use as a preservative for silage and other animal feed constituted 30% of the global consumption in 2009.<ref name=CEH/>
	As mentioned ], formic acid may serve as a convenient source of carbon monoxide by being readily decomposed by sulfuric acid.
			]s use formic acid as a ] against the tracheal mite ('']'') and the ] and ].<ref>{{cite journal |author= Hoppe, H. |author2=Ritter, W. |author3=Stephen, E. W. C.|year= 1989 |title= The control of parasitic bee mites: Varroa jacobsoni, Acarapis woodi and Tropilaelaps clareae with formic acid |journal= American Bee Journal}}</ref>
	==Reactions==
	Formic acid shares most of the chemical properties of other ]s. Reflecting its high acidity, its solutions in alcohols form esters spontaneously. Formic acid shares some of the ] properties of ]s, reducing solutions of gold, silver, and platinum to the metals.
	===Decomposition===		===Energy===
			Formic acid can be used directly in ]s or indirectly in hydrogen ]s.<ref>{{cite journal |doi=10.1016/j.jpowsour.2004.12.031 |title=Performance characterization of Pd/C nanocatalyst for direct formic acid fuel cells |journal=Journal of Power Sources |volume=144 |issue=1 |pages=28–34 |year=2005 |last1=Ha |first1=S |last2=Larsen |first2=R |last3=Masel |first3=R.I |bibcode=2005JPS...144...28H }}</ref><ref>{{cite news |title=Ant power: Take a ride on a bus that runs on formic acid |author=Jorn Madslien |url=https://www.bbc.com/news/business-40403351 |publisher=] |date=27 June 2017 |access-date=11 July 2017}}</ref>
	Heat and especially acids cause formic acid to decompose to ] (CO) and water (dehydration). Treatment of formic acid with ] is a convenient laboratory source of CO.<ref>{{OrgSynth|author=Koch, H.; Haaf, W.|title=1-Adamantanecarboxylic Acid|year=1973|collvol=5|collvolpages=20|prep=cv5p0020}}</ref><ref>{{OrgSynth|title=''p''-Tolualdehyde|author=G. H. Coleman, David Craig|collvol=2|collvolpages=583|year=1943|prep=cv2p0583}}</ref>
			Electrolytic conversion of electrical energy to chemical fuel has been proposed as a large-scale source of formate by various groups.<ref>{{Cite journal|last1=Yishai|first1=Oren|last2=Lindner|first2=Steffen N|last3=Gonzalez de la Cruz|first3=Jorge|last4=Tenenboim|first4=Hezi|last5=Bar-Even|first5=Arren|date=December 2016|title=The formate bio-economy|journal=Current Opinion in Chemical Biology|language=en|volume=35|pages=1–9|doi=10.1016/j.cbpa.2016.07.005|pmid=27459678}}</ref> The formate could be used as feed to modified '']'' bacteria for producing ].<ref>{{cite journal |display-authors=etal|last1=Shmuel Gleizer |title=Conversion of ''Escherichia coli'' to Generate All Biomass Carbon from CO<sub>2</sub> |journal=Cell |date=Nov 2019 |doi=10.1016/j.cell.2019.11.009 |volume=179 |issue=6 |pages=1255–1263.e12|pmid=31778652 |doi-access=free |pmc=6904909 }}</ref><ref>{{Cite journal|last1=Kim|first1=Seohyoung|last2=Lindner|first2=Steffen N.|last3=Aslan|first3=Selçuk|last4=Yishai|first4=Oren|last5=Wenk|first5=Sebastian|last6=Schann|first6=Karin|last7=Bar-Even|first7=Arren|date=2020-02-10|title=Growth of E. coli on formate and methanol via the reductive glycine pathway|url=https://www.nature.com/articles/s41589-020-0473-5|journal=Nature Chemical Biology|language=en|pages=538–545|doi=10.1038/s41589-020-0473-5|issn=1552-4469|volume=16|issue=5|pmid=32042198|s2cid=211074951}}</ref> Natural ] microbes can feed on formic acid or formate.
	In the presence of platinum, it decomposes with a release of ] and ]. Soluble ruthenium catalysts are also effective.<ref>{{cite journal | doi = 10.1002/anie.200800320 | author = C. Fellay, P. J. Dyson, G. Laurenczy | title = A Viable Hydrogen-Storage System Based On Selective Formic Acid Decomposition with a Ruthenium Catalyst | journal = ] | year = 2008 | volume = 47 | pages = 3966–3970 | pmid=18393267}}</ref><ref>G. Laurenczy, C. Fellay, P. J. Dyson, Hydrogen production from formic acid. ''PCT Int. Appl.'' (2008), 36pp. CODEN: PIXXD2 WO 2008047312 A1 20080424 AN 2008:502691</ref> Carbon monoxide free hydrogen has been generated in a very wide pressure range (1-600 bar).{{Citation needed|date=July 2010|reason=and clarify by what mechanism, otherwise this appears disjoint}} Formic acid has even been considered as a material for hydrogen storage.<ref>{{cite journal | last1 = Joó | first1 = Ferenc | title = Breakthroughs in Hydrogen Storage-Formic Acid as a Sustainable Storage Material for Hydrogen | journal = ChemSusChem | volume = 1 | issue = 10 | page = 805 | year = 2008 | pmid = 18781551 | doi = 10.1002/cssc.200800133}}</ref> The co-product of this decomposition, carbon dioxide, can be rehydrogenated back to formic acid in a second step. Formic acid contains 53 g L<sup>−1</sup> hydrogen at room temperature and atmospheric pressure, which is twice as much as compressed hydrogen gas can attain at 350 bar pressure. Pure formic acid is a liquid with a flash point - ignition temperature of + 69 °C, much higher than that of gasoline (– 40 °C) or ethanol (+ 13 °C).
			Formic acid has been considered as a means of ].<ref>{{cite journal |doi=10.1002/cssc.200800133 |pmid=18781551 |title=Breakthroughs in Hydrogen Storage-Formic Acid as a Sustainable Storage Material for Hydrogen |journal=ChemSusChem |volume=1 |issue=10 |pages=805–8 |year=2008 |last1=Joó |first1=Ferenc }}</ref> The co-product of this decomposition, carbon dioxide, can be rehydrogenated back to formic acid in a second step. Formic acid contains 53 g/L hydrogen at room temperature and atmospheric pressure, which is three and a half times as much as compressed hydrogen gas can attain at 350 bar pressure (14.7 g/L). Pure formic acid is a liquid with a ] of 69&nbsp;°C, much higher than that of gasoline (−40&nbsp;°C) or ethanol (13&nbsp;°C).{{citation needed|date=November 2017}}
	===Addition to alkenes===
	Formic acid is unique among the carboxylic acids in its ability to participate in addition reactions with ]s. Formic acids and alkenes readily react to form formate ]s. In the presence of certain acids, including ] and ]s, however, a variant of the ] occurs instead, and formic acid adds to the alkene to produce a larger carboxylic acid.
			It is possible to use formic acid as an intermediary to produce ] from {{CO2}} using microbes.<ref>{{Cite web|url=https://newenergyandfuel.com/http:/newenergyandfuel/com/2012/03/30/ucla-researchers-use-electricity-and-co2-to-make-butanol/|title=UCLA Researchers Use Electricity and CO2 to Make Butanol|date=30 March 2012 }}</ref><ref>{{Cite journal|title=Integrated Electromicrobial Conversion of CO2 to Higher Alcohols|first1=James C.|last1=Liao|first2=Kwang Myung|last2=Cho|first3=Yi-Xin|last3=Huo|first4=Peter|last4=Malati|first5=Wendy|last5=Higashide|first6=Tung-Yun|last6=Wu|first7=Steve|last7=Rogers|first8=David G.|last8=Wernick|first9=Paul H.|last9=Opgenorth|first10=Han|last10=Li|date=30 March 2012|journal=Science|volume=335|issue=6076|pages=1596|doi=10.1126/science.1217643|pmid=22461604|bibcode=2012Sci...335.1596L|s2cid=24328552}}</ref>
	===Formic acid anhydride===
	An unstable ], H(C=O)-O-(C=O)H, can be obtained by dehydration of formic acid with ] in ether at low temperature.<ref name=gwu>G. Wu, S. Shlykov, F. S. Van Alseny, H. J. Geise, E. Sluyts, B. J. Van der Veken (1995), ''Formic Anhydride in the Gas Phase, Studied by Electron Diffraction and Microwave and Infrared Spectroscopy, Supplemented with Ab-Initio Calculations of Geometries and Force Fields''. J. Phys. Chem., volume 99, issue 21, pages 8589–8598 {{doi|10.1021/j100021a022}}</ref>
	==History==		===Soldering===
			Formic acid has a potential application in ]. Due to its capacity to reduce oxide layers, formic acid gas can be blasted at an oxide surface to increase solder ].{{cn|date=June 2024}}
	Some ] and ] were aware that ant hills give off an acidic vapor as early as the 15th century. The first person to describe the isolation of this substance (by the distillation of large numbers of ants) was the ] naturalist ], in 1671. Ants secrete the formic acid for attack and defense purposes. Formic acid was first synthesized from ] by the ] chemist ]. In 1855, another French chemist, ], developed a synthesis from ] that is similar to that used today.
			===Chromatography===
			Formic acid is used as a volatile pH modifier in ] and ]. Formic acid is often used as a component of mobile phase in ] ] (RP-HPLC) analysis and separation techniques for the separation of hydrophobic macromolecules, such as peptides, proteins and more complex structures including intact viruses. Especially when paired with ] detection, formic acid offers several advantages over the more traditionally used ].<ref>{{Cite web |url=https://www.novapublishers.com/catalog/product_info.php?products_id=48192 |title=Archived copy |access-date=7 November 2017 |archive-date=7 November 2017 |archive-url=https://web.archive.org/web/20171107112257/https://www.novapublishers.com/catalog/product_info.php?products_id=48192 |url-status=dead }}{{full citation needed|date=November 2017}}</ref><ref>{{cite journal |doi=10.1016/S0021-9673(01)88415-6 |pmid=6304128 |title=Reversed-phase high-performance liquid chromatography of virus proteins and other large hydrophobic proteins in formic acid containing solvents |journal=Journal of Chromatography A |volume=252 |pages=241–54 |year=1982 |last1=Heukeshoven |first1=Jochen |last2=Dernick |first2=Rudolf }}</ref>
			===Other uses===
			Formic acid is also significantly used in the production of leather, including ] (23% of the global consumption in 2009<ref name=CEH/>), and in dyeing and finishing textiles (9% of the global consumption in 2009<ref name=CEH/>) because of its acidic nature. Use as a coagulant in the ]<ref name = Ullmann_2009/> consumed 6% of the global production in 2009.<ref name=CEH/>
			Formic acid is also used in place of mineral acids for various cleaning products,<ref name =Ullmann_2009/> such as ] remover and ]. Some formate ] are artificial flavorings and perfumes.
			Formic acid application has been reported to be an effective treatment for ]s.<ref name="pmid11589750">{{cite journal |doi=10.1046/j.1365-4362.2001.01242.x |pmid=11589750 |title=Topical formic acid puncture technique for the treatment of common warts |journal=International Journal of Dermatology |volume=40 |issue=6 |pages=415–9 |year=2001 |last1=Bhat |first1=Ramesh M |last2=Vidya |first2=Krishna |last3=Kamath |first3=Ganesh |s2cid=42351889 }}</ref>
	Formic acid was long considered a ] of only minor industrial interest in the chemical industry. In the late 1960s, however, significant quantities of it became available as a byproduct of ] production. It now finds increasing use as a preservative and antibacterial in ] feed.
	==Safety==		==Safety==
			Formic acid has low toxicity (hence its use as a food additive), with an {{LD50}} of 1.8{{nbsp}}g/kg (tested orally on mice). The concentrated acid is corrosive to the skin.<ref name=Ullmann_2009/>
	Formic acid in 85% concentration is not flammable, and diluted formic acid is on the US Food and Drug Administration list of food additives.<ref>US Code of Federal Regulations: 21 CFR 186.1316, 21 CFR 172.515</ref> The principal danger from formic acid is from skin or eye contact with the concentrated liquid or vapors. The US ] Permissible Exposure Level (]) of formic acid vapor in the work environment is 5 parts per million parts of air (]).
	Formic acid is readily metabolized and eliminated by the body. Nonetheless, it has specific ] effects; the formic acid and ] produced as metabolites of ] are responsible for the ] damage, causing blindness seen in methanol poisoning.<ref>{{cite web|url=http://www.newton.dep.anl.gov/askasci/chem03/chem03561.htm|title=Methanol and Blindness|publisher=Ask A Scientist, Chemistry Archive|accessdate=22 May 2007}}</ref> Some chronic effects of formic acid exposure have been documented. Some experiments on bacterial species have demonstrated it to be a ]<ref>{{cite web|url=http://www.osha.gov/SLTC/healthguidelines/formicacid/recognition.html|title=Occupational Safety and Health Guideline for Formic Acidpublisher=OSHA|accessdate=28 May 2011}}</ref>. Chronic exposure to humans may cause kidney damage. <ref>{{cite web|url=http://www.osha.gov/SLTC/healthguidelines/formicacid/recognition.html|title=Occupational Safety and Health Guideline for Formic Acidpublisher=OSHA|accessdate=28 May 2011}}</ref> Another effect of chronic exposure is development of a skin ] that manifests upon re-exposure to the chemical.		Formic acid is readily metabolized and eliminated by the body. Nonetheless, it has specific ] effects; the formic acid and ] produced as metabolites of ] are responsible for the ] damage, causing blindness, seen in ].<ref>{{cite journal |doi=10.1136/jnnp.72.4.423 |pmid=11909893 |pmc=1737836 |year=2002 |last1=Sadun |first1=A. A |title=Mitochondrial optic neuropathies |journal=Journal of Neurology, Neurosurgery, and Psychiatry |volume=72 |issue=4 |pages=423–5 }}</ref> Some chronic effects of formic acid exposure have been documented. Some experiments on bacterial species have demonstrated it to be a ].<ref name="osha.gov">{{cite web|url=http://www.osha.gov/SLTC/healthguidelines/formicacid/recognition.html|title=Occupational Safety and Health Guideline for Formic Acid|publisher=OSHA|access-date=28 May 2011|archive-date=20 September 2011|archive-url=https://web.archive.org/web/20110920200807/http://www.osha.gov/SLTC/healthguidelines/formicacid/recognition.html|url-status=dead}}</ref> Chronic exposure in humans may cause kidney damage.<ref name="osha.gov"/> Another possible effect of chronic exposure is development of a skin ] that manifests upon re-exposure to the chemical.
	Concentrated formic acid slowly decomposes to carbon monoxide and water, leading to pressure buildup in the container it is kept in. For this reason, 98% formic acid is shipped in plastic bottles with self-venting caps.		Concentrated formic acid slowly decomposes to carbon monoxide and water, leading to pressure buildup in the containing vessel. For this reason, 98% formic acid is shipped in plastic bottles with self-venting caps.{{cn|date=June 2024}}
	The hazards of solutions of formic acid depend on the concentration. The following table lists the ] of formic acid solutions:		The hazards of solutions of formic acid depend on the concentration. The following table lists the ] for formic acid solutions:{{citation needed|date=October 2021}}
	{| class = "wikitable"		{| class = "wikitable"
	|-		|-
	! ] (])		! ] (])
			! Pictogram
	! Classification
	! ]		! ]
	|-		|-
	| 2%&ndash;10%		| 2–10%
			| {{GHS07}}
	| Irritant ('''Xi''')
	| {{R36/38}}		| {{H-phrases|315}}
	|-		|-
			| 10–90%
	| 10%&ndash;90%
			| {{GHS05}}
	| Corrosive ('''C''')
	| {{R34}}		| {{H-phrases|313}}
	|-		|-
	| >90%		| >90%
			| {{GHS05}}
	| Corrosive ('''C''')
	| {{R35}}		| {{H-phrases|314}}
	|}		|}
			Formic acid in 85% concentration is flammable, and diluted formic acid is on the U.S. Food and Drug Administration list of food additives.<ref>{{CodeFedReg|21|186|1316}}, {{CodeFedReg|21|172|515}}</ref> The principal danger from formic acid is from skin or eye contact with the concentrated liquid or vapors. The U.S. ] Permissible Exposure Level (]) of formic acid vapor in the work environment is 5 ] (ppm) of air.<ref>{{Cite web |title=CDC - NIOSH Pocket Guide to Chemical Hazards - Formic acid |url=https://www.cdc.gov/niosh/npg/npgd0296.html |access-date=2024-11-01 |website=www.cdc.gov}}</ref>
	An ] for formic acid in body fluids, designed for determination of formate after methanol poisoning, is based on the reaction of formate with bacterial formate dehydrogenase.<ref>{{cite journal |journal= Biochem Med |year=1975 |volume=13 |issue=2 |pages=117–26 |title= Formate assay in body fluids: application in methanol poisoning |author= Makar AB, McMartin KE, Palese M, Tephly TR |doi=10.1016/0006-2944(75)90147-7 |pmid=1}}</ref>
	==See also==		==See also==
	* ]		* ]
			* ]
	==References==		==References==
	{{Reflist|2}}		{{Reflist}}
	==External links==		==External links==
			{{Commons}}
	{{commons|Formic acid|Formic acid}}
			{{EB1911 poster|Formic Acid}}
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			{{Molecules detected in outer space}}
	{{Use dmy dates|date=November 2010}}
			{{Authority control}}
	{{DEFAULTSORT:Formic Acid}}		{{DEFAULTSORT:Formic Acid}}
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