Oxalic acid

Oxalic acid is an organic compound with the formula C2H2O4. Some call it “crab acid” due to its appearance. It is a white crystalline solid that forms a colorless solution in water. Its condensed formula is HOOCCOOH, reflecting its classification as the simplest dicarboxylic acid.

Oxalic acid
Skeletal formula of oxalic acid
Space-filling model of oxalic acid
Names
Preferred IUPAC name
Oxalic acid[1]
Systematic IUPAC name
Ethanedioic acid[1]
Other names
Wood bleach, Crab Acid
Identifiers
3D model (JSmol)
3DMet
385686
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.123
EC Number
  • 205-634-3
2208
KEGG
MeSH Oxalic+acid
RTECS number
  • RO2450000
UNII
UN number 3261
Properties
C2H2O4
Molar mass 90.034 g·mol−1
(anhydrous)
126.065 g·mol−1 (dihydrate)
Appearance White crystals
Odor odorless
Density 1.90 g·cm−3 (anhydrous, at 17 °C)[2]
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
90-100 g/L (20 °C)[2]
Solubility 237 g/L (15 °C) in ethanol
14 g/L (15 °C) in diethyl ether [3]
Vapor pressure <0.001 mmHg (20 °C)[4]
Acidity (pKa) 1.25, 4.14[5]
Conjugate base Hydrogenoxalate
-60.05·10−6 cm3/mol
Pharmacology
QP53AG03 (WHO)
Hazards
Main hazards corrosive
Safety data sheet External MSDS
NFPA 704 (fire diamond)
Flash point 166 °C (331 °F; 439 K)
Lethal dose or concentration (LD, LC):
1000 mg/kg (dog, oral)
1400 mg/kg (rat)
7500 mg/kg (rat, oral)[6]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 mg/m3[4]
REL (Recommended)
 TWA 1 mg/m3 ST 2 mg/m3[4]
IDLH (Immediate danger)
 500 mg/m3[4]
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).
N verify (what is YN ?)
Infobox references

Its acid strength is much greater than that of acetic acid. Oxalic acid is a reducing agent[7] 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.

It occurs naturally in many foods, but excessive ingestion of oxalic acid or prolonged skin contact can be dangerous.

Its name comes from the fact that early investigators isolated oxalic acid from flowering plants of the genus Oxalis, commonly known as wood-sorrels.

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.[8] By 1773, François Pierre Savary of Fribourg, Switzerland had isolated oxalic acid from its salt in sorrel.[9]

In 1776, Swedish chemists Carl Wilhelm Scheele and Torbern Olof Bergman[10] 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.[11]

In 1824, the German chemist Friedrich Wöhler obtained oxalic acid by reacting cyanogen with ammonia in aqueous solution.[12] This experiment may represent the first synthesis of a natural product.[13]

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.[14] 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.[13]

Historically oxalic acid was obtained exclusively by using caustics, such as sodium or potassium hydroxide, on sawdust.[15] Pyrolysis of sodium formate (ultimately prepared from carbon monoxide), leads to the formation of sodium oxalate, easily converted to oxalic acid.

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.[16]

The hydrated solid can be dehydrated with heat or by azeotropic distillation.[17]

Developed in the Netherlands, an electrocatalysis by a copper complex helps reduce carbon dioxide to oxalic acid;[18] 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.[19] 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+          pKa = 1.27
C2O4H− ⇌ C
2O2−
4 + H+		          pKa = 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)).[20] 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.[21]

Oxalic acid's pKa values vary in the literature from 1.25-1.46 and 3.81-4.40.[22][23][24] The 100th ed of the CRC, released in 2019 has values of 1.25 and 3.81.[25]

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:[26]

[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.[27] 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 oxalate crystals in the sap, in the form of raphides. Bacteria produce oxalates from oxidation of carbohydrates.[13]

Plants of the genus Fenestraria produce optical fibers made from crystalline oxalic acid to transmit light to subterranean photosynthetic sites.[28]

Carambola, also known as starfruit, also contains oxalic acid along with caramboxin. Citrus juice contains small amounts of oxalic acid. Citrus fruits produced in organic agriculture contain less oxalic acid than those produced in conventional agriculture[29].

The formation of naturally occurring calcium oxalate patinas on certain limestone and marble statues and monuments has been proposed to be caused by the chemical reaction of the carbonate stone with oxalic acid secreted by lichen or other microorganisms.[30][31]

Production by fungi

Many soil fungus species secrete oxalic acid, resulting in greater solubility of metal cations, increased availability of certain soil nutrients, and can lead to the formation of calcium oxalate crystals.[32][33]

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.[34]

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.[35] 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,[36] thus is an interesting potential course of cancer treatment.

Applications

About 25% of produced oxalic acid will be used as a mordant in dyeing processes. It is used in bleaches, especially for pulpwood. It is also used in baking powder[13] 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). 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 oxalate crystals

Oxalic acid is used by some beekeepers as a miticide against the parasitic varroa mite.[37]

Oxalic acid is used to clean minerals.[38][39]

Oxalic acid is sometimes used in the aluminum anodizing process, with or without sulfuric acid. Compared to sulfuric acid anodizing, the coatings obtained are thinner and exhibit lower surface roughness.

Oxalic acid is an ingredient in some tooth whitening products.

Content in food items

[40]

VegetableOxalic acid
(g/100 g)a
Amaranth 1.09
Asparagus 0.13
Beans, snap 0.36
Beet leaves 0.61
Beetroot 0.06[41]
Broccoli 0.19
Brussels sprouts 0.02[41]
Cabbage 0.10
Carrot 0.50
Cassava 1.26
Cauliflower 0.15
Celery 0.19
Chicory 0.2
Chives 1.48
Collards 0.45
Coriander 0.01
Corn, sweet 0.01
Cucumber 0.02
Eggplant 0.19
Endive 0.11
Garlic 0.05
Kale 0.02
Lettuce 0.33
Okra 0.05
Onion 0.05
Parsley 0.04
Parsnip 0.04
Pea 0.05
Bell pepper 0.04
Potato 0.05
Purslane 1.31
Radish 0.48
Rhubarb leaves 0.52[42]
Rutabaga 0.03
Spinach 0.97 (ranges from .65 to 1.3 grams per 100 grams on fresh weight basis)[43]
Squash 0.02
Sweet potato 0.24
Swiss Chard, green 0.96 [41]
Tomato 0.05
Turnip 0.21
Turnip greens 0.05
Watercress 0.31

Toxicity

Oxalic acid in concentrated form can have harmful effects through contact and if ingested. It is not identified as mutagenic or carcinogenic, although there is a study suggesting it might cause breast cancer;[44] 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.[45]

In humans, ingested oxalic acid has an oral LDLo (lowest published lethal dose) of 600 mg/kg.[46] It has been reported that the lethal oral dose is 15 to 30 grams.[47]

Oxalate may enter cells where it is known to cause mitochondrial dysfunction.[48]

The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate,[49] the main component of calcium kidney stones. Oxalic acid can also cause joint pain by 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.

Notes

^a Unless otherwise cited, all measurements are based on raw vegetable weights with original moisture content.

gollark: > I appreciate all of you reporting this and leaving it so long without exploiting it (as far as I can tell). You have my gratitude!
gollark: Ah, apparently it was fixed 18 days ago?
gollark: https://github.com/pronouns/main/issues/29
gollark: But I don't think lyric had a PoC of the issue.
gollark: LyricLy actually did try and report it on the github.

References
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  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
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  4. NIOSH Pocket Guide to Chemical Hazards. "#0474". National Institute for Occupational Safety and Health (NIOSH).
  5. Bjerrum, J., et al. (1958) Stability Constants, Chemical Society, London.
  6. "Oxalic acid". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. Ullmann's Encyclopedia of Industrial Chemistry. Wiley. 2005. pp. 17624/28029. doi:10.1002/14356007. ISBN 9783527306732.
  8. 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".
  9. 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.
  10. 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.
  11. 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].)
  12. 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.
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  16. Practical Organic Chemistry by Julius B. Cohen, 1930 ed. preparation #42
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  27. Rombauer, Rombauer Becker, and Becker (1931/1997). Joy of Cooking, p.415. ISBN 0-684-81870-1.
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  32. Dutton, Martin V.; Evans, Christine S. (1 September 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.
  33. Gadd, Geoffrey M. (1 January 1999). "Fungal Production of Citric and Oxalic Acid: Importance in Metal Speciation, Physiology and Biogeochemical Processes". Advances in Microbial Physiology. Academic Press. 41: 47–92. doi:10.1016/S0065-2911(08)60165-4. ISBN 9780120277414. PMID 10500844.
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  41. Chai, Weiwen; Liebman, Michael (2005). "Effect of Different Cooking Methods on Vegetable Oxalate Content". Journal of Agricultural and Food Chemistry. 53 (8): 3027–30. doi:10.1021/jf048128d. PMID 15826055.
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  43. Durham, Sharon. "Making Spinach with Low Oxalate Levels". AgResearch Magazine (January 2017). United States Department of Agriculture. Retrieved 26 June 2017. The scientists analyzed oxalate concentrations in 310 spinach varieties—300 USDA germplasm accessions and 10 commercial cultivars. “These spinach varieties and cultivars displayed oxalate concentrations from 647.2 to 1286.9 mg/100 g on a fresh weight basis,” says Mou.
  44. Castellaro, Andrés M.; Tonda, Alfredo; Cejas, Hugo H.; Ferreyra, Héctor; Caputto, Beatriz L.; Pucci, Oscar A.; Gil, German A. (2015-10-22). "Oxalate induces breast cancer". BMC Cancer. 15: 761. doi:10.1186/s12885-015-1747-2. ISSN 1471-2407. PMC 4618885. PMID 26493452.
  45. Oxalic acid dihydrate. MSDS. sigmaaldrich.com
  46. "Oxalic Acid Material Safety Data Sheet" (PDF). Radiant Indus Chem. Archived from the original (PDF) on 2014-05-20. Retrieved 2014-05-20.
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  48. Patel, Mikita; Yarlagadda, Vidhush; Adedoyin, Oreoluwa; Saini, Vikram; Assimos, Dean G.; Holmes, Ross P.; Mitchell, Tanecia (May 2018). "Oxalate induces mitochondrial dysfunction and disrupts redox homeostasis in a human monocyte derived cell line". Redox Biology. 15: 207–215. doi:10.1016/j.redox.2017.12.003. PMC 5975227. PMID 29272854.
  49. EMEA Committee for veterinary medicinal products, oxalic acid summary report, December 2003
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