Copyright © Philip M. Parker, INSEAD. Terms of Use.
Definition: Formic Acid |
Formic AcidNoun1. A colorless; pungent fuming vesicatory liquid acid HCOOH found in ants and many plants; used in finishing textiles. Source: WordNet 1.7.1 Copyright © 2001 by Princeton University. All rights reserved. |
| Domain | Definitions |
Food & Agriculture | A volatile fatty acid occurring in traces in wines. Source: European Union. (references) |
Source: compiled by the editor from various references; see credits. | |
(From Wikipedia, the free Encyclopedia)
General
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| Name | Formic acid | |
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| Chemical formula | CH2O2 | |
| Formula weight | 46.03 amu | |
| Synonyms | methanoic acid, aminic acid, hydrogencarboxylic acid | |
| CAS number | 64-18-6 | |
Phase behavior
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| Melting point | 281.5 K (8.4 °C) | |
| Boiling point | 373.9 K (100.8°C) | |
| Triple point | 281.4 K (8.3°C) 0.0236 bar |
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| Liquid density | 1.22 ×103 kg/m3 | |
Acid-base properties
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| pKa | 3.75 | |
Liquid thermochemistry
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| ΔfH0liquid | -425.1 kJ/mol | |
| S0liquid | 131.8 J/mol·K | |
| ΔfusH | 12.7 kJ/mol | |
| ΔfusS | 45.1 J/mol·K | |
| Cp | 99.0 J/mol·K | |
Gas thermochemistry
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| ΔfH0gas | -378.6 kJ/mol | |
| S0gas | 248.7 J/mol·K | |
| ΔvapH | 22.7 kJ/mol | |
| Cp | 45.7 J/mol·K | |
Safety
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| Acute effects | Corrosive. Contact with concentrated vapors or solution can cause severe chemical burns. | |
| Chronic effecs | Repeated exposure can result in an allergic reaction. Suspected mutagen, may cause long-term liver and kidney damage. | |
| Flash point | 69°C | |
| Autoignition temperature | 601°C | |
| Explosive limits | 18-57% | |
More info
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| Properties | NIST WebBook | |
| MSDS | Hazardous Chemical Database | |
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SI units were used where possible. Unless otherwise stated, standard conditions were used.
Disclaimer and references | ||
Formic acid (systematically called methanoic acid) is the simplest carboxylic acid. Its formula is CH2O2 or HCOOH. Its structure is shown at right.
In nature, it is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. It is also the principal irritant in the leaves of the stinging nettle. Its name come from the Latin word for ant, formica, referring to its early isolation by the distillation of ant bodies.
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. With its growing use as a preservative and antibacterial in livestock feed, it is now produced for its own sake.
Formic acid shares most of the chemical properties of other carboxylic acids, although it will not form either an acyl chloride or an acid anhydride. Attempts to form either of these derivatives result in carbon monoxide instead. Heat can also cause formic acid to decompose to carbon monoxide. Formic acid shares some of the reducing properties of aldehydes.
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.
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
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 dead ants) was the English naturalist John Ray, in 1671. It 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.Properties
Formic acid is miscible with water and most polar organic solvents, and somewhat soluble in hydrocarbons. In hydrocarbons and in the vapor phase, is 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 infinite network of hydrogen bonded formic acid molecules.Production
A significant amount of formic acid is produced as a byproduct in the manufacture of other chemicals, especially acetic acid. However, this production in insufficient to meet the present demand for formic acid, and some formic acid must be produced for its own sake.
Industrially, 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:
However, direct hydrolysis of methanol requires a large excess of water to proceed efficiently, and so some producers perform it by an indirect route, first reacting the methyl formate with ammonia to produce formamide, and then hydrolyzing the formamide with sulfuric acid to produce formic acid:
This technique has problems of its own, particularly disposing of the ammonium sulfate byproduct, and so recently, some manufacturers have developed energy-efficient means of separating formic acid from the large excess of using direct hydrolysis. In one of these processes, used by BASF, the formic acid is removed from the water by liquid extraction with an organic base.
Source: adapted by the editor from Wikipedia, the free encyclopedia under a copyleft GNU Free Documentation License (GFDL) from the article "Formic acid."
Crosswords: Formic Acid |
| English words defined with "formic acid": Carbamic acid ♦ Fatty acid, Formate, formic, Formyl ♦ Lignoceric ♦ Oxalic acid. (references) |
| Specialty definitions using "formic acid": COLORER, HIDES AND SKINS, colorer, machine ♦ dye mixer, dye weigher, dyer and washer ♦ leather colorer. (references) |
| Domain | Title |
References | |
Books | |
Source: compiled by the editor from various references; see credits. | |
Expression using "formic acid": amido formic acid. Additional references. | |
| Source: compiled by the editor from various references; see credits. |
| The following statistics estimate the number of searches per day across the major English-language search engines as identified by various trade publications. Hyperlinks lead to commercial use of the expression at Amazon.com. |
| Expression | Frequency per Day |
formic acid | 56 |
| Source: compiled by the editor from various references; see credits. | |
| Language | Translations for "formic acid"; alternative meanings/domain in parentheses. | ||||||||||||||||||||||||||||||||||
Albanian | acid thnegëlor. (various references) | ||||||||||||||||||||||||||||||||||
Danish | myresyre (formylic acid, methanoic acid), E236 (formylic acid, methanoic acid). (various references) | ||||||||||||||||||||||||||||||||||
Dutch | methaanzuur (formylic acid, methanoic acid), E 236 (formylic acid, methanoic acid). (various references) | ||||||||||||||||||||||||||||||||||
Finnish | muurahaishappo (E236, formylic acid, methanoic acid). (various references) | ||||||||||||||||||||||||||||||||||
French | acide formique (formylic acid). (various references) | ||||||||||||||||||||||||||||||||||
German | Ameisensäure (E236, formylic acid, methanoic acid). (various references) | ||||||||||||||||||||||||||||||||||
Greek | μυρμηκικό οξύ (E236, formylic acid, methanoic acid). (various references) | ||||||||||||||||||||||||||||||||||
Hungarian | hangyasav. (various references) | ||||||||||||||||||||||||||||||||||
Italian | E236 (E236, formylic acid, methanoic acid), acido formico (E236, formylic acid, methanoic acid). (various references) | ||||||||||||||||||||||||||||||||||
Japanese Kanji | 蟻酸 . (various references) | ||||||||||||||||||||||||||||||||||
Japanese Katakana | ぎさ". (various references) | ||||||||||||||||||||||||||||||||||
Pig Latin | ormicfay aciday E236 (E236, formylic acid, methanoic acid), acido metanoico (E236, formylic acid, methanoic acid), acido formico (E236, formylic acid, methanoic acid). (various references) муравьиная кислота. (various references) ácido fórmico (E236, formylic acid, methanoic acid). (various references) myrsyra (E236, formylic acid, methanoic acid), metansyra (E236, formylic acid, methanoic acid). (various references) formik asit, karınca asidi (formalin). (various references) | ||||||||||||||||||||||||||||||||||
| Language | Period | Translations |
| Latin | 500 BCE-Modern | formica. (various references) |
| Source: compiled by the editor from various references. | ||
Scrabble® Enable2K-Verified Anagrams | |
| Words within the letters "a-c-c-d-f-i-i-m-o-r" | |
-2 letters: dioramic. | |
-3 letters: aciform, cricoid. | |
-4 letters: accord, acidic, amidic, cadmic, daimio, formic, midair, modica, moirai. | |
-5 letters: acmic, acrid, amici, amido, aroid, caird, carom, circa, comic, coria, croci, daric, domic, farci, fiord, foram, idiom, imido, iodic, macro, mafic, micra, micro, moira, oidia, radii, radio. | |
| Words containing the letters "a-c-c-d-f-i-i-m-o-r" | |
+5 letters: diffractometric. | |
| Source: compiled by the editor from various references; see credits. SCRABBLE® is a registered trademark. All intellectual property rights in and to the game are owned in the U.S.A and Canada by Hasbro Inc., and throughout the rest of the world by J.W. Spear & Sons Limited of Maidenhead, Berkshire, England, a subsidiary of Mattel Inc. Mattel and Spear are not affiliated with Hasbro. | |
Hexadecimal (or equivalents, 770AD-1900s) (references)46 6F 72 6D 69 63 41 63 69 64 |
| Leonardo da Vinci (1452-1519; backwards) (references)
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Binary Code (1918-1938, probably earlier) (references)01000110 01101111 01110010 01101101 01101001 01100011 00100000 01000001 01100011 01101001 01100100 |
HTML Code (1990) (references)F o r m i c   A c i d |
ISO 10646 (1991-1993) (references)0046 006F 0072 006D 0069 0063 0041 0063 0069 0064 |
Encryption (beginner's substitution cypher): (references)408184797569235697570 |
| 1. Definition 2. Crosswords 3. Usage: Commercial 4. Expressions | 5. Expressions: Internet 6. Translations: Modern 7. Translations: Ancient 8. Anagrams | 9. Orthography 10. Bibliography |
Copyright © Philip M. Parker, INSEAD. Terms of Use.
| Note to the press & webmasters - this dictionary can be linked, indexed, or referred to using the following non-English expressions: woordeboek, fjalor, معجم, قاموس, diccionariu, речник, diccionari, diksyonario, diksinario, 字典, gérlyver, slovník, ordbog, woordenboek, shimiyuc p'anca, orðabók, orðbók, dictionnaire, wurdboek, wörterbuch, λεξικό, אוצר מילים, szótár, uqausiit tukingit, dizionario, 字引 , じい, じびき, じて", ディクショナリー , じり", じしょ, '"かい, ディクショナリ , 사 , dizionari, recnik, fockleyr, dikshonario, słownik, dicionário, dicţionar, dicziunari, словарь, lolomi fefiloi, foclair, abardair, faclair, briathrachan, pukuntau, leksikon, rečnik, vocabbulariu, diccionario, sí-chazamagâma, ordbok, lexikon, พจนานุกรม, sözlük, ansiklopedik sözlük, словник, довідник, có tính chất sách vở, geirlyfr, geiriadur, for dictionary; definisie, qartësi, përcaktim, saktësi, الوضوحية في الشيء, حد, تحديد, تعريف, التحديد, الإيضاحية, яснота, сила, очертания, дефиниция, 定義 , 定义, definice, deskriptordefinition, definitie, määritelmä, définition, ορισμός, "'"ר", "'בל", meghatározás, definíció, definizione, 確定 , ディーゼル電気車 , デ'ドロ酢酸 , デフィニション , ディフィニション , ていぎ, かくてい, 의, geyrid, meenaghey, keeayllaght, baght, definishon, definição, definiţie, determinare, definire, определение, definicija, definición, definition, açıklama, belirleme, belirtme, kesinleştirme, tanım, tarif, seçiklik, tanımlama, чіткість, тлумачення, виразність, визначення, дефініція, ясність, чітка чутність, sự định rõ, sự định nghĩa, lời định nghĩa sự định, diffiniad, darnodiad, for definition; vertaling, transferim, transmetim, ترجمة من لغة أجنبية للغة الأم, ترجمة, إفتتان, транслация, огъване, превод, предаване, поддаване, тълкуване, превеждане, 翻译, překlad, oversættelse, translatie, taajuusmuutos, translaatio, traduction, oersetting, Übersetzung, μετάφραση, תור'מ ות, תר'ום, "עתק", "עתק, fordítás, traduzione, 翻訳 , へい"ういどう, やくしょ, やくしゅつ, "うどく, ほ"やく, トランスレーション , やくじゅつ, ほ"やくしょ, 번역, tradukshon, tradução, translaţie, tãlmãcire, traducere, сдвиг, трансляция, перемещение, перевод, tumačenje, traducción, översättning, tercüme, процес перекладу, переклад, пояснення, переміщення, sự dịch, sự biến th nh sự giải thích, trosiad, for translation; Albaans, Albanies, Albaniese taal, shqip, الألبانية, الألباني, албанец, албански език, албански, Albanyano, 阿"巴尼亚语, 阿爾巴尼亞人 , albánský, Albanees, albanskt, albanialainen, Albanais, Albaneesk, albaner, αλβανικόσ, Αλβανός, αλβανόσ, arbnisht, arbërisht, albán, albanskur, albanska, AlbÚinis, albanese, 알"니아, Albaneagh, albanês, arnãut, albanez, arnãuţesc, албанский, Alapania, albanski, albanac, albanés, alban, Arnavut, албанський, албанка, албанець, for Albanian; Deens, danisht, danishte, لغة الدانمركية, نوع كعك, دانماركي, датски език, датски, Daniko, 丹麦语, dánský, dánština, danskur, danskt, tanskalainen, danois, Deensk, dänisch, δανικόσ, δανόσ, עו'ת שמרים, " י, dán, danska, Danmhairgis, danese, 덴마크, Danvargish, Danvargagh, danes, dinamarquês, danez, датский, danski, danski jezik, danés, dansk, danimarkalı, danimarka dili, датський, датська мова, tiếng Đan-mạch, for Danish; Nederlands, Hollands, holandez, هولندي, اللغة الهولندية, холандски, немски език, холандски език, холандците, немски, Olandes, 菏蘭語 , 荷兰语, holandský, nizozemský, hollandsk, hollendskt, hollantilainen, néerlandais, Nederlânsk, holländisch, ολλανδικόσ, ολλανδόσ, holandisht, "ול "י, holland, hollenskur, Ollainnis, olandese, 네덜란", Belanda, Ollanish, Germaanish, Tatimana, nederlandsk, ulandes, hulandes, holandês, neerlandés, olandez, nemţesc, limba olandezã, german, голландский, holanđanin, u škripcu, holandski, holandés, bakratongo, holländsk, ชาวเนเธอร์แลน"์, เกี่ยวกับเนเธอร์แลน"์, รรยา, alman, eş, flemenkçe, holandaca, hollanda, karı, hollandalı, hollandalılara özgü olan, Hollandali, hollanda'ya ait, голландська мова, голландський, ngôn ngữ khó hiểu, "b xã", for Dutch; Fins, finlandez, finlandishte, finlandisht, اللغة الفنلندية, فنلندية, فنلندي, фински език, фински, Pinlandino, 芬蘭語 , 芬兰语, finský, finskt, suomi, suomalainen, finnois, Finlandaise, finlandais, finnisch, φινλανδικόσ, פי י, finn, finnskur, finnska, finlandese, 핀란", Fynlannish, Fynlannagh, finlandês, finês, finlandezã, финский, Finisi, finski jezik, finski, finlandés, finés, finsk, fince, finlandiya'ya özgü, фінська мова, фінський, tiếng Phần-lan, for Finnish; Franse taal, Frans, franceze, francez, frëngjisht, frëng, frëngjishte, فرنسي, اللغة الفرنسية, الشعب الفرنسي, gall, френски език, френски, Pranses, 法國 , 法文 , 法語 , 法语, francouzština, francouzský, franskur, franskt, ranskalainen, français, Frânsk, französisch, γάλλοσ, γαλλικόσ, γαλλική γλώσσα, γαλλίδα, צרפתי, צרפתית, francia, Fraincis, francese, フレコン化 , フランス" , 仏文 , 仏 , ふつぶ", フレンチ , フランセ , ふつ, "랑스, Perancis, Ny Frangee, Mooinjey ny Frank, frances, franses, francês, francezii, francezã, franţuzesc, franţuzeşte, французский, Falani, francuski jezik, francuski, francuzi, francés, sí-Fulentji, fransk, franska, fransızca, Fransiz, fransızca ile ilgili, fransız, fransa ile ilgili, французька мова, французький, Ffrengig, isiFulentshi, for French; Duits, Duitser, Duitse taal, Germaan, gjerman, ضرب من الرقص, جرماني, المانية, الماني, اللغة الألمانية, роден, германски, немски език, немски, немец, готически, германец, 德語 , 德语, 德文 , 德國 , nìmecký, nìmec, tysker, Duitse, týskur, týskt, týskari, saksalainen, Allemand, Dútsk, Deutsche, Deutsch, "ερμανός, gjermanisht, 'רמ י, 'רמ ית, német, þjóðverji, þýskur, GearmÚnach, GearmÚinis, tedesco, ジプシー音楽 , ジャーマン , 독일, todesch, Germaanagh, Garmane, Germaanish, Carmane, aleman, Niemiec, niemiecki, alemão, alemand, neamţ, немецкий, Siamani, germanski, alemán, Tudesku, Doysri, mjeremani, mdachi, sí-Jalimáne, tysk, เยอรมัน, าษาเยอรมัน, Alman, німкеня, німецький, німець, $sisters german$ chị em ruột, $cousin german$ anh chị em con chú bác ruột, sister, Almaenwr, isiJalimane, iliJalimane, iJalimane, for German; Grieks, Griek, الإغريقي, يوناني, اللغة اليونانية, Griegu, гръцки език, гръцки, грък, Griyego, 希臘語 , 希腊语, řecký, řeètina, řek, græker, grikst, kreikkalainen, grec, Gryk, Gryksk, Gryks, grieche, ελληνικόσ, 'Ελληνας, יו ית, יו י, görög, Grikki, greco, ギリシア語 , ギリシア", 그리스, Greagish, Greagagh, grego, grèc, greacã, греческий, Eleni, grk, grčki jezik, grčki, griego, grek, Yunanli, yunanlı, yunanca, yunan, Rumca, yunanistan'a ait, rum, грек, гречанка, грецька мова, грецький, kẻ cắp b gi gặp nhau, quân bạc bịp tôi không thể hiểu được điều đó thật l kỳ phùng địch thủ, người Hy-lạp tiếng Hy-lạp kẻ bịp bợm, kẻ lừa đảo, Groegwr, for Greek; Hongaars, Hongaar, hungarez, الهنغاري, مجري, هنغاري, المجري, اللغة الهنغارية, Húngaru, унгарски език, унгарски, унгарец, Hungaryan, 匈牙利語 , 匈牙利语, maïarský, maïar, maïarština, ungarer, Hongaarse, ungarskt, unkarilainen, hongrois, Hongaarsk, ungar, Ούγγρος, "ו 'רי, magyar, ungherese, 헝가리, Ungaarish, Ungaaragh, Węgier, ongrés, ungureşte, ungur, limba maghiarã, unguresc, maghiar, limba ungarã, венгр, венгерский, mađarski, mađar, mađarski jezik, húngaro, ungrare, ชาวฮังการี, macarca, macar, угорська мова, угорка, угорський, угорець, người Hung-ga-ri tiếng Hung-ga-ri, for Hungarian; Italianer, Italiaans, Italiaan, شخص إيطالي, اللغة الإيطالية, الإيطالي, إيطالي, Italianu, италиански език, италиански, италианец, Italyano, 意大利 , 意大利語 , 意大利语, italština, italský, ital, italiener, italienskt, italialainen, Italien, Italjaansk, italienisch, Ιταλός, italisht, איטלקי, איטלקית, olasz, Ítali, IodÚilis, italiano, 이탈리아, Iddaalish, Włoch, italianã, italienesc, italieneşte, italian, итальянский язык, итальянский, итальянец, Italia, italijanski, italijanski jezik, italijan, sí-Taliyáne, italienare, italiensk, italienska, เกี่ยวกับอิตาลี, ชาวอิตาลี, าษาอิตาลี, italyanca, italyan, італі"ць, італійська мова, італійський, італійка, for Italian; Portugees, portugez, portugalisht, اللغة البرتغالية, البرتغالية, البرتغالي, португалски език, португалски, португалец, Potuges, 葡萄牙语, 葡萄牙人 , 葡萄牙語 , portugalský, portugiser, portugisiskt, portugalilainen, portugais, Portugeesk, portugiesisch, πορτογάλοσ, ορτογάλος, portugál, Portaingéilis, portoghese, ポルトガル語 , ポルトガル", 포르투갈, Portiugish, Portiugagh, portugues, Portugalczyk, português, portughez, португальский, portugalski jezik, portugalski, portugalac, portugués, Mreno, si-Putúkezi, portugis, portekiz, Portekízlí, portekizli, portekizce, португальська мова, португальський, португалець, người B"-đ o-nha tiếng B"-đ o-nha, for Portuguese; Russies, Rus, الروسية, روسي, اللغة الروسية, Rusu, руски, руски език, руснак, Rusyan, 俄語 , 俄语, 俄文 , ruština, ruský, russer, russur, russiskt, venäläinen, Russysk, Russe, russisch, Ρώσος, רוסי, orosz, rússneskur, Rússi, Rúisis, russo, ロシア語 , ロシア", 러시아, Rooshish, Rooshagh, russisk, Rosjanin, русский, Lusia, ruski jezik, ruski, ruso, sí-Rashîya, ryss, ชาวรัสเซีย, rusça, росіянка, росіянин, російська мова, російський, người Nga tiếng Nga, for Russian; Spaans, Spaanse taal, spanjoll, اللغة الأسبانية, الأسبانية, أسباني, испански език, испански, espanyoles, Espanyol, 西班牙语, 西班牙文 , 西班牙語 , španìlský, španìlština, spanskt, espanjalainen, espagnol, Spaansk, spanisch, ισπανικά, ισπανικόσ, ισπανοί, karaiñe'êmegua, ספר"ית, ספר"י, spanyol, SpÚinnis, spagnolo, スペイン語 , スパイ罪 , スペイン", スパニッシュ , 스페인, Spaainagh, Spaainish, spañó, espanhol, espanhòl, spaniolesc, spanioleşte, spaniol, испанский, Sipaniolo, španski jezik, španski, español, spanska språk, spansk, ispanyollar, ispanyolca, ispanyol, іспанська мова, іспанський, for Spanish; Sweeds, suedez, اللغة السويدية, Suecu, шведски език, шведски, швед, Swedis, 瑞典語 , 瑞典语, švédský, švédština, Zweeds, svenskt, ruotsalainen, suédois, Sweedsk, schwedisch, σουηδικόσ, σουηδικά, svéd, sænskur, Sualainnis, svedese, スウェーデン語 , スウェーデン", 스웨덴, Soolynish, Soolynagh, suèc, шведский, švedski jezik, švedski, sueco, svensk, เกี่ยวกับคน าษาและวั'นธรรมของประเทศสวีเ"น, isveççe, isveç dili, isveç, Ísveçlí, шведська мова, шведський, người Thuỵ điển tiếng Thuỵ điển, for Swedish; Turks, turk, تركي أحد أبناء تركيا, اللغة التركية, Turcu, турски, турски език, Turko, 土耳其, 土耳其語 , tureètina, turecký, turkist, turkkilainen, turque, turc, Turksk, türkisch, τούρκικοσ, טורקי, török, Yn Turkish, Turkagh, turcesc, турецкий, turski jezik, turski, turco, turkisk, türk, türkçe, турецька мова, турецький, tiếng Thổ nhĩ kỳ, for Turkish; |
