WordNet

a salt or ester of oxalic acid
street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/03/07 18:23:41」(JST)

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Oxalic acid is an organic compound with the formula C₂H₂O₄. It is a colorless crystalline solid that forms a colorless solution in water. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid. Its acid strength is much greater than that of acetic acid. Oxalic acid is a reducing agent ^[6] and its conjugate base, known as oxalate (C
2O2−
4), is a chelating agent for metal cations. Typically, oxalic acid occurs as the dihydrate with the formula C₂H₂O₄·2H₂O. Excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.

1 History
2 Preparation
- 2.1 Laboratory methods
3 Structure
4 Reactions
5 Occurrence
- 5.1 Biosynthesis
- 5.2 Occurrence in foods and plants
- 5.3 Other
6 Biochemistry
7 Applications
- 7.1 Cleaning
- 7.2 Extractive metallurgy
- 7.3 Niche uses
8 Content in food items
9 Toxicity and safety
10 References
11 External links

History

The preparation of salts of oxalic acid from plants had been known, at the latest, since 1745, when the Dutch botanist and physician Herman Boerhaave isolated a salt from sorrel.^[7] By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.^[8]

In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman^[9] produced oxalic acid by reacting sugar with concentrated nitric acid; Scheele called the acid that resulted socker-syra or såcker-syra (sugar acid). By 1784, Scheele had shown that "sugar acid" and oxalic acid from natural sources were identical.^[10]

In 1824, the German chemist Friedrich Wöhler obtained oxalic acid by reacting cyanogen with ammonia in aqueous solution.^[11] This experiment may represent the first synthesis of a natural product.^[12]

Preparation

Oxalic acid is mainly manufactured by the oxidation of carbohydrates or glucose using nitric acid or air in the presence of vanadium pentoxide. A variety of precursors can be used including glycolic acid and ethylene glycol.^[13] A newer method entails oxidative carbonylation of alcohols to give the diesters of oxalic acid:

4 ROH + 4 CO + O₂ → 2 (CO₂R)₂ + 2 H₂O

These diesters are subsequently hydrolyzed to oxalic acid. Approximately 120,000 tonnes are produced annually.^[12]

Historically oxalic acid was obtained exclusively by using caustics, such as sodium or potassium hydroxide, on sawdust.^[14]

Laboratory methods

Although it can be readily purchased, oxalic acid can be prepared in the laboratory by oxidizing sucrose using nitric acid in the presence of a small amount of vanadium pentoxide as a catalyst.^[15]

The hydrated solid can be dehydrated with heat or by azeotropic distillation.^[16]

Developed in the Netherlands, an electrocatalysis by a copper complex helps reduce carbon dioxide to oxalic acid;^[17] this conversion uses carbon dioxide as a feedstock to generate oxalic acid.

Structure

Anhydrous oxalic acid exists as two polymorphs; in one the hydrogen-bonding results in a chain-like structure whereas the hydrogen bonding pattern in the other form defines a sheet-like structure.^[18] Because the anhydrous material is both acidic and hydrophilic (water seeking), it is used in esterifications.

Reactions

Oxalic acid is a relatively strong acid, despite being a carboxylic acid:

C₂O₄H₂ ⇌ C₂O₄H⁻ + H⁺ pK_a = 1.27

C₂O₄H⁻ ⇌ C
2O2−
4 + H⁺ pK_a = 4.27

Oxalic acid undergoes many of the reactions characteristic of other carboxylic acids. It forms esters such as dimethyl oxalate (m.p. 52.5 to 53.5 °C (126.5 to 128.3 °F)).^[19] It forms an acid chloride called oxalyl chloride.

Oxalate, the conjugate base of oxalic acid, is an excellent ligand for metal ions, e.g. the drug oxaliplatin.

Oxalic acid and oxalates can be oxidized by permanganate in an autocatalytic reaction.^[20]

Occurrence

Biosynthesis

At least two pathways exist for the enzyme-mediated formation of oxalate. In one pathway, oxaloacetate, a component of the Krebs citric acid cycle, is hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase:^[21]

[O₂CC(O)CH₂CO₂]²⁻ + H₂O → C
2O2−
4 + CH
3CO−
2 + H⁺

It also arises from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol.

Occurrence in foods and plants

Calcium oxalate is the most common component of kidney stones. Early investigators isolated oxalic acid from wood-sorrel (Oxalis). Members of the spinach family and the brassicas (cabbage, broccoli, brussels sprouts) are high in oxalates, as are sorrel and umbellifers like parsley.^[22] Rhubarb leaves contain about 0.5% oxalic acid and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. Similarly the Virginia creeper, a common decorative vine, produces oxalic acid in its berries as well as oxalite crystals in the sap (in the form of raphides). Bacteria produce oxalates from oxidation of carbohydrates.^[12]

Plants of the Fenestraria genus produce optical fibers made from crystalline oxalic acid to transmit light to subterranean photosynthetic sites.^[23]

Other

Oxidized bitumen or bitumen exposed to gamma rays also contains oxalic acid among its degradation products. Oxalic acid may increase the leaching of radionuclides conditioned in bitumen for radioactive waste disposal.^[24]

Biochemistry

The conjugate base of oxalic acid is the hydrogenoxalate anion, and its conjugate base (oxalate) is a competitive inhibitor of the lactate dehydrogenase (LDH) enzyme.^[25] LDH catalyses the conversion of pyruvate to lactic acid (end product of the fermentation (anaerobic) process) oxidising the coenzyme NADH to NAD⁺ and H⁺ concurrently. Restoring NAD⁺ levels is essential to the continuation of anaerobic energy metabolism through glycolysis. As cancer cells preferentially use anaerobic metabolism (see Warburg effect) inhibition of LDH has been shown to inhibit tumor formation and growth,^[26] thus is an interesting potential course of cancer treatment.

Applications

About 25% of produced oxalic acid is used as a mordant in dyeing processes. It is used in bleaches, especially for pulpwood. It is also used in baking powder^[12] and as a third reagent in silica analysis instruments.

Cleaning

Oxalic acid's main applications include cleaning or bleaching, especially for the removal of rust (iron complexing agent). Bar Keepers Friend is an example of a household cleaner containing oxalic acid. Its utility in rust removal agents is due to its forming a stable, water-soluble salt with ferric iron, ferrioxalate ion.

Extractive metallurgy

Oxalic acid is an important reagent in lanthanide chemistry. Hydrated lanthanide oxalates form readily in very strongly acidic solutions in a densely crystalline, easily filtered form, largely free of contamination by nonlanthanide elements. Thermal decomposition of these oxalate gives the oxides, which is the most commonly marketed form of these elements.

Niche uses

Honeybee coated with oxalic acid crystals

Vaporized oxalic acid, or a 3.2% solution of oxalic acid in sugar syrup, is used by some beekeepers as a miticide against the parasitic varroa mite.^[27]

Oxalic acid is rubbed onto completed marble sculptures to seal the surface and introduce a shine. Oxalic acid is also used to clean iron and manganese deposits from quartz crystals.^[28]^[29]

Oxalic acid is used as a bleach for wood, removing black stains caused by water penetration.

Content in food items

Vegetable	Oxalic acid (g/100 g)^[30]^{[clarification needed]}
Amaranth	7000109000000000000♠ 1.09
Asparagus	6999130000000000000♠ 0.13
Beans, snap	6999360000000000000♠ 0.36
Beet leaves	6999610000000000000♠ 0.61
Broccoli	6999190000000000000♠ 0.19
Brussels sprouts	6999360000000000000♠ 0.36
Cabbage	6999100000000000000♠ 0.10
Carrot	6999500000000000000♠ 0.50
Cassava	7000126000000000000♠ 1.26
Cauliflower	6999150000000000000♠ 0.15
Celery	6999190000000000000♠ 0.19
Chicory	6999210000000000000♠ 0.2
Chives	7000148000000000000♠ 1.48
Collards	6999450000000000000♠ 0.45
Coriander	6998100000000000000♠ 0.01
Corn, sweet	6998100000000000000♠ 0.01
Cucumber	6998200000000000000♠ 0.02
Eggplant	6999190000000000000♠ 0.19
Endive	6999110000000000000♠ 0.11
Garlic	6999360000000000000♠ 0.36
Kale	6998200000000000000♠ 0.02
Lettuce	6999330000000000000♠ 0.33
Okra	6998500000000000000♠ 0.05
Onion	6998500000000000000♠ 0.05
Parsley	7000170000000000000♠ 1.70
Parsnip	6998400000000000000♠ 0.04
Pea	6998500000000000000♠ 0.05
Bell pepper	6998400000000000000♠ 0.04
Potato	6998500000000000000♠ 0.05
Purslane	7000131000000000000♠ 1.31
Radish	6999480000000000000♠ 0.48
Rhubarb leaves	6999520000000000000♠ 0.52^[31]
Rutabaga	6998300000000000000♠ 0.03
Spinach	6999970000000000000♠ 0.97
Squash	6998200000000000000♠ 0.02
Sweet potato	6999240000000000000♠ 0.24
Tomato	6998500000000000000♠ 0.05
Turnip	6999210000000000000♠ 0.21
Turnip greens	6998500000000000000♠ 0.05
Watercress	6999310000000000000♠ 0.31

Toxicity and safety

Oxalic acid in concentrated form can have harmful effects through contact and if ingested; manufacturers provide details in Material Safety Data Sheets (MSDS). It is not identified as mutagenic or carcinogenic; there is a possible risk of congenital malformation in the fetus; may be harmful if inhaled, and is extremely destructive to tissue of mucous membranes and upper respiratory tract; harmful if swallowed; harmful to and destructive of tissue and causes burns if absorbed through the skin or is in contact with the eyes. Symptoms and effects include a burning sensation, cough, wheezing, laryngitis, shortness of breath, spasm, inflammation and edema of the larynx, inflammation and edema of the bronchi, pneumonitis, pulmonary edema.^[32]

In humans, ingested oxalic acid has an oral LD_Lo (lowest published lethal dose) of 600 mg/kg.^[33] It has been reported that the lethal oral dose is 15 to 30 grams.^[34]

The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate,^[35] the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints. Ingestion of ethylene glycol results in oxalic acid as a metabolite which can also cause acute kidney failure.

References

^ ^a ^b Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 415, 745. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Radiant Agro Chem. "Oxalic Acid MSDS".
^ ^a ^b ^c ^d "NIOSH Pocket Guide to Chemical Hazards #0474". National Institute for Occupational Safety and Health (NIOSH).
^ Bjerrum, J., et al. (1958) Stability Constants, Chemical Society, London.
^ "Oxalic acid". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
^ Ullmann's Encyclopedia of Industrial Chemistry. Wiley. 2005. pp. 17624/28029. ISBN 9783527306732.
^ See:
- Herman Boerhaave, Elementa Chemiae (Basil, Switzerland: Johann Rudolph Im-hoff, 1745), volume 2, pp. 35-38. (in Latin) From p. 35: "Processus VII. Sal nativum plantarum paratus de succo illarum recens presso. Hic Acetosae." (Procedure 7. A natural salt of plants prepared from their freshly pressed juice. This [salt obtained] from sorrel.)
- Henry Enfield Roscoe and Carl Schorlemmer, ed.s, A Treatise on Chemistry (New York, New York: D. Appleton and Co., 1890), volume 3, part 2, p. 105.
- See also Wikipedia's articles "Oxalis acetosella" and "Potassium hydrogen oxalate".
^ See:
- François Pierre Savary, Dissertatio Inauguralis De Sale Essentiali Acetosellæ [Inaugural dissertation on the essential salt of wood sorrel] (Jean François Le Roux, 1773). (in Latin) Savary noticed that when he distilled sorrel salt (potassium hydrogen oxalate), crystals would sublimate onto the receiver. From p. 17: "Unum adhuc circa liquorem acidum, quem sal acetosellae tam sincerissimum a nobis paratum quam venale destillatione fundit phoenomenon erit notandum, nimirum quod aliquid ejus sub forma sicca crystallina lateribus excipuli accrescat, … " (One more [thing] will be noted regarding the acid liquid, which furnished for us sorrel salt as pure as commercial distillations, [it] produces a phenomenon, that evidently something in dry, crystalline form grows on the sides of the receiver, … ) These were crystals of oxalic acid.
- Leopold Gmelin with Henry Watts, trans., Hand-book of Chemistry (London, England: Cavendish Society, 1855), volume 9, p. 111.
^ See:
- Torbern Bergman with Johan Afzelius (1776) Dissertatio chemica de acido sacchari [Chemical dissertation on sugar acid] (Uppsala, Sweden: Edman, 1776).
- Torbern Bergman, Opuscula Physica et Chemica, (Leipzig (Lipsia), (Germany): I.G. Müller, 1776), volume 1, "VIII. De acido Sacchari," pp. 238-263.
^ Carl Wilhelm Scheele (1784) "Om Rhabarber-jordens bestånds-delar, samt sått at tilreda Acetosell-syran" (On rhubarb-earth's constituents, as well as ways of preparing sorrel-acid), Kungliga Vetenskapsakademiens Nya Handlingar [New Proceedings of the Royal Academy of Science], 2nd series, 5 : 183-187. (in Swedish) From p. 187: "Således finnes just samma syra som vi genom konst af socker med tilhjelp af salpeter-syra tilreda, redan förut af naturen tilredd uti o̊rten Acetosella." (Thus it is concluded [that] the very same acid as we prepare artificially by means of sugar with the help of nitric acid, [was] previously prepared naturally in the herb acetosella [i.e., sorrel].)
^ See:
- F. Wöhler (1824) "Om några föreningar af Cyan" (On some compounds of cyanide), Kungliga Vetenskapsakademiens Handlingar [Proceedings of the Royal Academy of Science], pp. 328-333. (in Swedish)
- Reprinted in German as: F. Wöhler (1825) "Ueber Cyan-Verbindungen" (On cyanide compounds), Annalen der Physik und Chemie, 2nd series, 3 : 177-182.
^ ^a ^b ^c ^d Wilhelm Riemenschneider, Minoru Tanifuji "Oxalic acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a18_247.
^ Eiichi, Yonemitsu; Tomiya, Isshiki; Tsuyoshi, Suzuki and Yukio, Yashima "Process for the production of oxalic acid", U.S. Patent 3,678,107, priority date March 15, 1969
^ Von Wagner, Rudolf (1897). Manual of chemical technology. New York: D. Appleton & Co. p. 499.
^ Practical Organic Chemistry by Julius B. Cohen, 1930 ed. preparation #42
^ Clarke H. T.;. Davis, A. W. (1941). "Oxalic acid (anhydrous)". Org. Synth.: 421. ; Coll. Vol., 1
^ Bouwman, Elisabeth; Angamuthu, Raja; Byers, Philip; Lutz, Martin; Spek, Anthony L. (July 15, 2010). "Electrocatalytic CO₂ Conversion to Oxalate by a Copper Complex". Science. 327 (5393): 313–315. doi:10.1126/science.1177981. PMID 20075248.
^ Wells, A.F. (1984) Structural Inorganic Chemistry, Oxford: Clarendon Press. ISBN 0-19-855370-6.
^ Bowden, E. (1943). "Methyl oxalate". Org. Synth.: 414. ; Coll. Vol., 2
^ Kovacs K.A.; Grof P.; Burai L.; Riedel M. (2004). "Revising the mechanism of the permanganate/oxalate reaction". J. Phys. Chem. A. 108 (50): 11026–11031. doi:10.1021/jp047061u.
^ Dutton, M. V.; Evans, C. S. (1996). "Oxalate production by fungi: Its role in pathogenicity and ecology in the soil environment". Canadian Journal of Microbiology. 42 (9): 881–895. doi:10.1139/m96-114. .
^ Rombauer, Rombauer Becker, and Becker (1931/1997). Joy of Cooking, p.415. ISBN 0-684-81870-1.
^ Attenborough, David. "Surviving." The Private Life of Plants: A Natural History of Plant Behaviour. Princeton, NJ: Princeton UP, 1995. 265+. "OpenLibrary.org: The Private Life of Plants" Print.
^ EPJ Web of Conferences
^ Novoa, William; Alfred Winer; Andrew Glaid; George Schwert (1958). "Lactic Dehydrogenase V. inhibition by Oxamate and Oxalate". Journal of Biological Chemistry. 234 (5): 1143–8. PMID 13654335.
^ Le, Anne; Charles Cooper; Arvin Gouw; Ramani Dinavahi; Anirban Maitra; Lorraine Deck; Robert Royer; David Vander Jagt; Gregg Semenza; Chi Dang (14 December 2009). "Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression". Proceedings of the National Academy of Sciences. 107: 2037–2042. doi:10.1073/pnas.0914433107. PMC 2836706. PMID 20133848.
^ Exploring New Methods for Varroa Mite Control, Yu-Lun Lisa Fu
^ Jackson, Faith. "Quartz Crystal Cleaning". bluemooncrystals.com
^ "Rock Currier – Cleaning Quartz". mindat.org
^ All data not specifically annotated is from Agriculture Handbook No. 8-11, Vegetables and Vegetable Products, 1984. ("Nutrient Data : Oxalic Acid Content of Selected Vegetables". ars.usda.gov)
^ Pucher, GW; Wakeman, AJ; Vickery, HB (1938). "The organic acids of rhubarb (Rheum hybridium). III. The behavior of the organic acids during culture of excised leaves". Journal of Biological Chemistry. 126 (1): 43.
^ Oxalic acid dihydrate. MSDS. sigmaaldrich.com
^ "Oxalic Acid Material Safety Data Sheet" (PDF). Radiant Indus Chem. Retrieved 2014-05-20.
^ "CDC – Immediately Dangerous to Life or Health Concentrations (IDLH): Oxalic acid – NIOSH Publications and Products". cdc.gov
^ EMEA Committee for veterinary medicinal products, oxalic acid summary report, December 2003

External links

Oxalic acid MS Spectrum
International Chemical Safety Card 0529
NIOSH Guide to Chemical Hazards (CDC)
Table: Oxalic acid content of selected vegetables (USDA)
Alternative link: Table: Oxalic Acid Content of Selected Vegetables (USDA)
About rhubarb poisoning (The Rhubarb Compendium)
Oxalosis & Hyperoxaluria Foundation (OHF) The Oxalate Content of Food 2008 (PDF)
Oxalosis & Hyperoxaluria Foundation (OHF) Diet Information
Calculator: Water and solute activities in aqueous oxalic acid

UpToDate Contents

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1. 腎結石が確認された成人患者の評価および結石形成の有無が不明の患者の治療 evaluation of the adult patient with established nephrolithiasis and treatment if stone composition is unknown
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English Journal

Ultrasound assisted extraction and characterization of pectin from tomato waste.

Grassino AN1, Brnčić M2, Vikić-Topić D3, Roca S3, Dent M4, Brnčić SR5.
Food chemistry.Food Chem.2016 May 1;198:93-100. doi: 10.1016/j.foodchem.2015.11.095. Epub 2015 Nov 18.
Pectin was extracted from tomato waste using two different extraction methods to assess its potential utilization as an alternative source of commercial pectin production. Tomato waste was treated with ammonium oxalate/oxalic acid by conventional extraction (CE), under reflux and ultrasound assisted
PMID 26769509

Chrysotile asbestos detoxification with a combined treatment of oxalic acid and silicates producing amorphous silica and biomaterial.

Valouma A1, Verganelaki A2, Maravelaki-Kalaitzaki P3, Gidarakos E4.
Journal of hazardous materials.J Hazard Mater.2016 Mar 15;305:164-70. doi: 10.1016/j.jhazmat.2015.11.036. Epub 2015 Nov 23.
This study was primarily imposed by the ever increasing need for detoxification of asbestos and asbestos containing materials (ACM), with potential application onsite. The present work investigates potential detoxification of pure chrysotile (Chr) asbestos via a combined treatment of oxalic acid dih
PMID 26685063

Japanese Journal

Laboratory photochemical processing of aqueous aerosols : formation and degradation of dicarboxylic acids, oxocarboxylic acids and alpha-dicarbonyls

Pavuluri C. M.,Kawamura K.,Mihalopoulos N.,Swaminathan T.
Atmospheric chemistry and physics 15(14), 7999-8012, 2015-09-17
… The results show that photochemical degradation of oxalic (C-2), malonic (C-3) and other C-8-C-12 diacids overwhelmed their production in aqueous aerosols, whereas succinic acid (C-4) and C-5-C-7 diacids showed a significant increase (ca. … The photochemical formation of oxoacids and alpha-dicarbonyls overwhelmed their degradation during the early stages of experiment except for omega-oxooctanoic acid (omega C-8), which showed a similar pattern to that of C-4. …
NAID 120005651861

Analysis of Cr with Various Valence States in Industrial EAF Slag for Making Stainless Steel

Wang Hui,Yan Baijun,Li Fan
ISIJ International 55(7), 1425-1431, 2015
… oxalic acid was applied to leach the Cr(0) in alloy drops; …
NAID 130005089771

「シュウ酸」

Oxalic acid
Names
	Preferred IUPAC name Oxalic acid
	Systematic IUPAC name Ethanedioic acid
	Other names Wood bleach
Identifiers
CAS Number	144-62-7
3D model (Jmol)	Interactive image
3DMet	B00059
Beilstein Reference	385686
ChEBI	CHEBI:16995
ChEMBL	ChEMBL146755
ChemSpider	946
DrugBank	DB03902
ECHA InfoCard	100.005.123
EC Number	205-634-3
Gmelin Reference	2208
KEGG	C00209
MeSH	Oxalic+acid
PubChem	971
RTECS number	RO2450000
UNII	9E7R5L6H31
UN number	3261
	InChI InChI=1S/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6) Key: MUBZPKHOEPUJKR-UHFFFAOYSA-N ;
	SMILES C(=O)(C(=O)O)O ;
Properties
Chemical formula	C2H2O4
Molar mass	90.03 g·mol−1; (anhydrous); 126.065 g mol−1 (dihydrate)
Appearance	White crystals
Odor	odorless
Density	1.90 g cm−3 (anhydrous); 1.653 g cm−3 (dihydrate)
Melting point	189 to 191 °C (372 to 376 °F; 462 to 464 K); 101.5 °C (214.7 °F; 374.6 K) dihydrate
Solubility in water	143 g/L (25 °C)
Solubility	237 g/L (15 °C) in ethanol 14 g/L (15 °C) in diethyl ether
Vapor pressure	<0.001 mmHg (20 °C)
Acidity (pKa)	1.25, 4.14
Magnetic susceptibility (χ)	-60.05·10−6 cm3/mol
Pharmacology
ATCvet code	QP53AG03 (WHO)
Hazards
Main hazards	T
Safety data sheet	External MSDS
NFPA 704	1 3 0
Flash point	166 °C (331 °F; 439 K)
	Lethal dose or concentration (LD, LC):
LDLo (lowest published)	1000 mg/kg (dog, oral); 1400 mg/kg (rat); 7500 mg/kg (rat, oral)
	US health exposure limits (NIOSH):
PEL (Permissible)	TWA 1 mg/m3
REL (Recommended)	TWA 1 mg/m3 ST 2 mg/m3
IDLH (Immediate danger)	500 mg/m3
Related compounds
Related compounds	oxalyl chloride; disodium oxalate; calcium oxalate; phenyl oxalate ester
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: oxalic acid, oxalate
関: シュウ酸塩、シュウ酸エステル

HOOC-COOH

酸解離定数

pK1＝ 1.271
pK2＝ 4.266

wikipedia ja

H2C2O4 + H2O → H3O+ + HC2O4- pK1=1.27
HC2O4- + H2O → H3O+ + C2O42- pK2=4.27

「oxalate」

　　[★]

シュウ酸、(化合物)ュウ酸塩、シュウ酸エステル

関: oxalic acid

「glyoxalic acid」

　　[★]

グリオキサル酸

関: glyoxalate、glyoxylate、glyoxylic acid

「oxal」

　　[★]

comb form

シュウ酸の

HOOC-COOH

ex.

オキサロ酢酸 oxaloacetate

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 415, 745. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] Radiant Agro Chem. "Oxalic Acid MSDS".

[PGCH-3] "NIOSH Pocket Guide to Chemical Hazards #0474". National Institute for Occupational Safety and Health (NIOSH).

[4] Bjerrum, J., et al. (1958) Stability Constants, Chemical Society, London.

[5] "Oxalic acid". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).

[Oxalic_Acid:_Uses-6] Ullmann's Encyclopedia of Industrial Chemistry. Wiley. 2005. pp. 17624/28029. ISBN 9783527306732.

[7] See:

Herman Boerhaave, Elementa Chemiae (Basil, Switzerland: Johann Rudolph Im-hoff, 1745), volume 2, pp. 35-38. (in Latin) From p. 35: "Processus VII. Sal nativum plantarum paratus de succo illarum recens presso. Hic Acetosae." (Procedure 7. A natural salt of plants prepared from their freshly pressed juice. This [salt obtained] from sorrel.)

Henry Enfield Roscoe and Carl Schorlemmer, ed.s, A Treatise on Chemistry (New York, New York: D. Appleton and Co., 1890), volume 3, part 2, p. 105.

See also Wikipedia's articles "Oxalis acetosella" and "Potassium hydrogen oxalate".

[8] Herman Boerhaave, Elementa Chemiae (Basil, Switzerland: Johann Rudolph Im-hoff, 1745), volume 2, pp. 35-38. (in Latin) From p. 35: "Processus VII. Sal nativum plantarum paratus de succo illarum recens presso. Hic Acetosae." (Procedure 7. A natural salt of plants prepared from their freshly pressed juice. This [salt obtained] from sorrel.)

[9] Henry Enfield Roscoe and Carl Schorlemmer, ed.s, A Treatise on Chemistry (New York, New York: D. Appleton and Co., 1890), volume 3, part 2, p. 105.

[10] See also Wikipedia's articles "Oxalis acetosella" and "Potassium hydrogen oxalate".

[8] See:

François Pierre Savary, Dissertatio Inauguralis De Sale Essentiali Acetosellæ [Inaugural dissertation on the essential salt of wood sorrel] (Jean François Le Roux, 1773). (in Latin) Savary noticed that when he distilled sorrel salt (potassium hydrogen oxalate), crystals would sublimate onto the receiver. From p. 17: "Unum adhuc circa liquorem acidum, quem sal acetosellae tam sincerissimum a nobis paratum quam venale destillatione fundit phoenomenon erit notandum, nimirum quod aliquid ejus sub forma sicca crystallina lateribus excipuli accrescat, … " (One more [thing] will be noted regarding the acid liquid, which furnished for us sorrel salt as pure as commercial distillations, [it] produces a phenomenon, that evidently something in dry, crystalline form grows on the sides of the receiver, … ) These were crystals of oxalic acid.

Leopold Gmelin with Henry Watts, trans., Hand-book of Chemistry (London, England: Cavendish Society, 1855), volume 9, p. 111.

[12] François Pierre Savary, Dissertatio Inauguralis De Sale Essentiali Acetosellæ [Inaugural dissertation on the essential salt of wood sorrel] (Jean François Le Roux, 1773). (in Latin) Savary noticed that when he distilled sorrel salt (potassium hydrogen oxalate), crystals would sublimate onto the receiver. From p. 17: "Unum adhuc circa liquorem acidum, quem sal acetosellae tam sincerissimum a nobis paratum quam venale destillatione fundit phoenomenon erit notandum, nimirum quod aliquid ejus sub forma sicca crystallina lateribus excipuli accrescat, … " (One more [thing] will be noted regarding the acid liquid, which furnished for us sorrel salt as pure as commercial distillations, [it] produces a phenomenon, that evidently something in dry, crystalline form grows on the sides of the receiver, … ) These were crystals of oxalic acid.

[13] Leopold Gmelin with Henry Watts, trans., Hand-book of Chemistry (London, England: Cavendish Society, 1855), volume 9, p. 111.

[9] See:

Torbern Bergman with Johan Afzelius (1776) Dissertatio chemica de acido sacchari [Chemical dissertation on sugar acid] (Uppsala, Sweden: Edman, 1776).

Torbern Bergman, Opuscula Physica et Chemica, (Leipzig (Lipsia), (Germany): I.G. Müller, 1776), volume 1, "VIII. De acido Sacchari," pp. 238-263.

[15] Torbern Bergman with Johan Afzelius (1776) Dissertatio chemica de acido sacchari [Chemical dissertation on sugar acid] (Uppsala, Sweden: Edman, 1776).

[16] Torbern Bergman, Opuscula Physica et Chemica, (Leipzig (Lipsia), (Germany): I.G. Müller, 1776), volume 1, "VIII. De acido Sacchari," pp. 238-263.

[10] Carl Wilhelm Scheele (1784) "Om Rhabarber-jordens bestånds-delar, samt sått at tilreda Acetosell-syran" (On rhubarb-earth's constituents, as well as ways of preparing sorrel-acid), Kungliga Vetenskapsakademiens Nya Handlingar [New Proceedings of the Royal Academy of Science], 2nd series, 5 : 183-187. (in Swedish) From p. 187: "Således finnes just samma syra som vi genom konst af socker med tilhjelp af salpeter-syra tilreda, redan förut af naturen tilredd uti o̊rten Acetosella." (Thus it is concluded [that] the very same acid as we prepare artificially by means of sugar with the help of nitric acid, [was] previously prepared naturally in the herb acetosella [i.e., sorrel].)

[11] See:

F. Wöhler (1824) "Om några föreningar af Cyan" (On some compounds of cyanide), Kungliga Vetenskapsakademiens Handlingar [Proceedings of the Royal Academy of Science], pp. 328-333. (in Swedish)

Reprinted in German as: F. Wöhler (1825) "Ueber Cyan-Verbindungen" (On cyanide compounds), Annalen der Physik und Chemie, 2nd series, 3 : 177-182.

[19] F. Wöhler (1824) "Om några föreningar af Cyan" (On some compounds of cyanide), Kungliga Vetenskapsakademiens Handlingar [Proceedings of the Royal Academy of Science], pp. 328-333. (in Swedish)

[20] Reprinted in German as: F. Wöhler (1825) "Ueber Cyan-Verbindungen" (On cyanide compounds), Annalen der Physik und Chemie, 2nd series, 3 : 177-182.

[Ullmann-12] Wilhelm Riemenschneider, Minoru Tanifuji "Oxalic acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a18_247.

[13] Eiichi, Yonemitsu; Tomiya, Isshiki; Tsuyoshi, Suzuki and Yukio, Yashima "Process for the production of oxalic acid", U.S. Patent 3,678,107, priority date March 15, 1969

[14] Von Wagner, Rudolf (1897). Manual of chemical technology. New York: D. Appleton & Co. p. 499.

[cohen-15] Practical Organic Chemistry by Julius B. Cohen, 1930 ed. preparation #42

[16] Clarke H. T.;. Davis, A. W. (1941). "Oxalic acid (anhydrous)". Org. Synth.: 421. ; Coll. Vol., 1

[Bouwman-17] Bouwman, Elisabeth; Angamuthu, Raja; Byers, Philip; Lutz, Martin; Spek, Anthony L. (July 15, 2010). "Electrocatalytic CO₂ Conversion to Oxalate by a Copper Complex". Science. 327 (5393): 313–315. doi:10.1126/science.1177981. PMID 20075248.

[18] Wells, A.F. (1984) Structural Inorganic Chemistry, Oxford: Clarendon Press. ISBN 0-19-855370-6.

[19] Bowden, E. (1943). "Methyl oxalate". Org. Synth.: 414. ; Coll. Vol., 2

[20] Kovacs K.A.; Grof P.; Burai L.; Riedel M. (2004). "Revising the mechanism of the permanganate/oxalate reaction". J. Phys. Chem. A. 108 (50): 11026–11031. doi:10.1021/jp047061u.

[21] Dutton, M. V.; Evans, C. S. (1996). "Oxalate production by fungi: Its role in pathogenicity and ecology in the soil environment". Canadian Journal of Microbiology. 42 (9): 881–895. doi:10.1139/m96-114. .

[22] Rombauer, Rombauer Becker, and Becker (1931/1997). Joy of Cooking, p.415. ISBN 0-684-81870-1.

[23] Attenborough, David. "Surviving." The Private Life of Plants: A Natural History of Plant Behaviour. Princeton, NJ: Princeton UP, 1995. 265+. "OpenLibrary.org: The Private Life of Plants" Print.

[24] EPJ Web of Conferences

[25] Novoa, William; Alfred Winer; Andrew Glaid; George Schwert (1958). "Lactic Dehydrogenase V. inhibition by Oxamate and Oxalate". Journal of Biological Chemistry. 234 (5): 1143–8. PMID 13654335.

[26] Le, Anne; Charles Cooper; Arvin Gouw; Ramani Dinavahi; Anirban Maitra; Lorraine Deck; Robert Royer; David Vander Jagt; Gregg Semenza; Chi Dang (14 December 2009). "Inhibition of lactate dehydrogenase A induces oxidative stress and inhibits tumor progression". Proceedings of the National Academy of Sciences. 107: 2037–2042. doi:10.1073/pnas.0914433107. PMC 2836706. PMID 20133848.

[27] Exploring New Methods for Varroa Mite Control, Yu-Lun Lisa Fu

[28] Jackson, Faith. "Quartz Crystal Cleaning". bluemooncrystals.com

[29] "Rock Currier – Cleaning Quartz". mindat.org

[30] All data not specifically annotated is from Agriculture Handbook No. 8-11, Vegetables and Vegetable Products, 1984. ("Nutrient Data : Oxalic Acid Content of Selected Vegetables". ars.usda.gov)

[31] Pucher, GW; Wakeman, AJ; Vickery, HB (1938). "The organic acids of rhubarb (Rheum hybridium). III. The behavior of the organic acids during culture of excised leaves". Journal of Biological Chemistry. 126 (1): 43.

[32] Oxalic acid dihydrate. MSDS. sigmaaldrich.com

[33] "Oxalic Acid Material Safety Data Sheet" (PDF). Radiant Indus Chem. Retrieved 2014-05-20.

[34] "CDC – Immediately Dangerous to Life or Health Concentrations (IDLH): Oxalic acid – NIOSH Publications and Products". cdc.gov

[35] EMEA Committee for veterinary medicinal products, oxalic acid summary report, December 2003

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