Grundinformationen
- Standard-SMILES
O.O.O=C(O)C(=O)O- InChIKey
GEVPUGOOGXGPIO-UHFFFAOYSA-N- Summenformel
- C2H2O4.2H2O
- Durchschnittliche Molmasse
- 126,07 g/mol
- Monoisotopische Masse
- 126,01643791
Überblick
Oxalic acid is a dicarboxylic acid. It is a colorless crystalline solid that dissolves in water to give colorless, acidic solutions. In terms of acid strength, it is much stronger than acetic acid. Oxalic acid, because of its di-acid structure can also act as a chelating agent for metal cations. About 25% of produced oxalic acid is used as a mordant in dyeing processes. It is also used in bleaches, especially for pulpwood. Oxalic acid's main applications include cleaning (it is also found in baking powder) or bleaching, especially for the removal of rust. Oxalic acid is found in a number of common foods with members of the spinach family being particularly high in oxalates. Beat leaves, parsley, chives and cassava are quite rich in oxalate. Rhubarb leaves contain about 0.5% oxalic acid and jack-in-the-pulpit (Arisaema triphyllum) contains calcium oxalate crystals. Bacteria naturally produce oxalates from the oxidation of carbohydrates. At least two pathways exist for the enzyme-mediated formation of oxalate in humans. In one pathway, oxaloacetate (part of the citric acid cycle) can be hydrolyzed to oxalate and acetic acid by the enzyme oxaloacetase. Oxalic acid can also be generated from the dehydrogenation of glycolic acid, which is produced by the metabolism of ethylene glycol. Oxalate is a competitive inhibitor of lactate dehydrogenase (LDH). LDH catalyses the conversion of pyruvate to lactic acid oxidizing the coenzyme NADH to NAD+ and H+ concurrently. As cancer cells preferentially use aerobic glycolysis, inhibition of LDH has been shown to inhibit tumor formation and growth. However, oxalic acid is not particularly safe and is considered a mild toxin. In particular, it is a well-known uremic toxin. In humans, ingested oxalic acid has an oral lowest-published-lethal-dose of 600 mg/kg. It has been reported that the lethal oral dose is 15 to 30 grams. The toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, the main component of kidney stones. Oxalic acid can also cause joint pain due to the formation of similar precipitates in the joints.
Namen und Bezeichner
- Bevorzugter Name
- Oxalic acid dihydrate
- IUPAC
- oxalic acid;dihydrate
- Englischer Name
- Oxalic acid dihydrate
- Summenformel
- C2H6O6
- Molmasse
- 126.07
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
6153-56-6- PubChem CID
- 61373
- DTXSID
DTXSID2075003- ChEMBL
CHEMBL5315063- UNII
- 0K2L2IJ59O
- EC Number
- 612-167-2
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 76,6 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 71,5
Experimentelle und physikochemische Eigenschaften
Density
1.65 g/cm³
1.653 @25 °C
Animal Drugs
EMA approved medicines: Veterinary medicine
EMA approved medicines: Veterinary medicine
Melting Point
101-102 °C
189.5 °C
Physical Description
Large Crystals; Dry Powder; Other Solid; Liquid; Liquid; Other Solid
Colorless solid; [ICSC] Colorless hygroscopic crystals; [Sigma-Aldrich MSDS]
COLOURLESS CRYSTALS.
Physikochemische Eigenschaften
- Schmelzpunkt
- 104 · 104-106 °C(lit.)
- Siedepunkt
- 108 · 108-109°C
- Dichte
- 1 · 1,65 g/cm3
- Dampfdichte
- 4.4 · 4.4 (vs air)
- Dampfdruck
- 0.01 mm · <0.01 mm Hg ( 20 °C)
- Flammpunkt
- 157 °C · 157°C
- storage temp.
- 5 °C · Store at +5°C to +30°C.
- Löslichkeit
- 2 O: · H2O: soluble1M at 20°C, clear, colorless
- Aggregatzustand
- Powder/Solid
- Wichte
- 1.65 · 1.65
- Farbe
- Yellow to yellow-green
- PH
- 1 · ~1.0 (25℃, 1M in H2O)
- Wasserlöslichkeit
- 138 g/L · 138 g/L (20 ºC)
- Merck
- 14 · 14,6911
- BRN
- 3679436 · 3679436
- Stabilität
- Stable. Incompatible with bases, acid chlorides, steel, silver, silver compounds, moisture. Avoid contact with metals.
- InChI
- 1S/C2H2O4.2H2O/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);2*1H2
- InChIKey
- GEVPUGOOGXGPIO-UHFFFAOYSA-N
- SMILES
- [H]O[H].[H]O[H].OC(=O)C(O)=O
- CAS Datenbank
- 6153 · 6153-56-6(CAS DataBase Reference)
- NIST chemische Informationen
- Oxalic acid dihydrate(6153-56-6)
- EPA chemische Informationen
- Oxalic acid dihydrate (6153-56-6)
- Absorption
- 303 nm · cut-off at 303nm in H2O at 1M
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 1.1% (6 of 561) of reports.
Danger
H302+H312 (12.7%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oral; acute toxicity, dermal]
P260, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 561 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Gefahrenhinweise
Regulatory Information
Chemical: Ethanedioic acid, dihydrate
Ethanedioic acid, dihydrate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanedioic acid, dihydrate are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Oxalic acid dihydrate: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes burns; Ingestion may have effects on calcium balance; Repeated or prolonged exposure may cause kidney stones; [ICSC] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion and skin absorption; May have teratogenic effects; Targets the kidney, nerves, blood, and eyes; [Sigma-Aldrich MSDS] See Oxalic acid.
Chemical Dangers
Decomposes on contact with hot surfaces or flames. This produces formic acid and carbon monoxide. The solution in water is a medium strong acid. Reacts violently with strong oxidants. This generates fire and explosion hazard. Reacts with some silver compounds. This produces explosive silver oxalate. Attacks some forms of plastic.
Hazard Classes and Categories
Acute Tox. 4 (98.8%)
Acute toxicity - category 4
Sicherheit und Schutzausrüstung
First Aid Measures
Fresh air, rest. Half-upright position. Refer immediately for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer for medical attention .
Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention.
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance, protective gloves and safety goggles. Sweep spilled substance into covered plastic containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.
Threshold Limit Values (TLV)
1.0 [mg/m3]
2.0 [mg/m3]
1 mg/m
Toxikologische Informationen
Treatment
Acute Exposure: If oxalic acid is swallowed, immediately give the person water or milk, unless instructed otherwise by a health care provider. DO NOT give water or milk if the person is having symptoms (such as vomiting, convulsions, or a decreased level of alertness) that make it hard to swallow. If acute exposure occurs to the eyes, irrigate opened eyes for several minutes under running water. Chronic exposure: in some patients with primary hyperoxaluria type 1, pyridoxine treatment (vitamin B6) may decrease oxalate excretion and prevent kidney stone formation.
Health Effects
Because it binds vital nutrients such as calcium, long-term consumption of foods high in oxalic acid can be problematic. Healthy individuals can safely consume such foods in moderation, but those with kidney disorders, gout, rheumatoid arthritis, or certain forms of chronic vulvar pain (vulvodynia) are typically advised to avoid foods high in oxalic acid or oxalates. The calcium oxalate precipitate (better known as kidney stones) obstruct the kidney tubules. Conversely, calcium supplements taken along with foods high in oxalic acid can cause calcium oxalate to precipitate out in the gut and drastically reduce the levels of oxalate absorbed by the body (by 97% in some cases.) Chronically high levels of oxalic acid are associated with at least 2 inborn errors of metabolism including: Type I primary hyperoxaluria and Primary hyperoxaluria. Oxalate stones in primary hyperoxaluria tend to be severe, resulting in relatively early kidney damage (before age 20), which impairs the excretion of oxalate leading to a further acceleration in accumulation of oxalate in the body. After the development of renal failure patients may develop oxalate deposits in the bones, joints and bone marrow. Severe cases may develop haematological problems such as anaemia and thrombocytopaenia. The deposition of oxalate in the body is sometimes called "oxalosis" to be distinguished from "oxaluria" which refers to oxalate in the urine.
Toxicity Summary
The affinity of divalent metal ions is sometimes reflected in their tendency to form insoluble precipitates. Thus in the body, oxalic acid also combines with metals ions such as Ca2+, Fe2+, and Mg2+ to deposit crystals of the corresponding oxalates, which irritate the gut and kidneys. (2) Therefore the toxicity of oxalic acid is due to kidney failure caused by precipitation of solid calcium oxalate, 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 that can also cause acute kidney failure.
Signs and Symptoms
Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing. Headache.
Redness. Pain. Skin burns.
Redness. Pain. Blurred vision. Burns.
Sore throat. Burning sensation. Abdominal pain. Laboured breathing. Convulsions. Paralysis. Cardiac dysrhythmia. Shock or collapse.
Oxalic acid poisoning symptoms include weakness, burning in the mouth, death from cardiovascular collapse, on the respiratory system, throat – burning in the throat, abdominal pain, nausea, vomiting, diarrhea, convulsions, and coma.
Sicherheitsdaten
- wgk
- 1
- tsca
- Yes
- ridadr
- UN 3261 8/PG 3
- hs_code
- 29171100
- RTECS-Nr.
- RO2450000
- risk_code
- 21/22-41
- Toxizität
- LD50 orally in Rabbit: 375 mg/kg
- hazard_code
- Xn,C
- safety_code
- 24/25-39-37-36-26
- hazard_class
- 8
- packing_group
- III
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
Uses
Used in calico printing and dyeing, bleaching straw hats and leather, cleaning wood and metals, purifying methanol, decolorizing crude glycerol, stabilizing hydrocyanic acid, removing paint, and removing stains; Also used in ceramics and pigments, in veterinary hemostatic solutions, in blood specimen anticoagulants, and in other industries (paper, photography, engraving, and rubber manufacturing); [Merck Index] Permitted for use as an inert ingredient in non-food pesticide products; [EPA]
Pulp and Paper Processing [Category: Industry]
Oxalic acid and oxalates are abundantly present in many plants, most notably fat hen (lamb's quarters), sorrel, and Oxalis species. The root and/or leaves of rhubarb and buckwheat are listed being high in oxalic acid.[8] Other edible plants that contain significant concentrations of oxalic acid include—in decreasing order—star fruit (carambola), black pepper, parsley, poppy seed, amaranth, spinach, chard, beets, cocoa, chocolate, most nuts, most berries, and beans. (L618)
Anwendungen
VerwendenOxalic acid dihydrate is a purifying agent in pharmaceutical industry, special in antibiotic medication, such as Oxytetracycline , Chloramphenicol , etc; * Precipitating agent in Rare-earth mineral processing; * Bleaching agent in the textile activities, wood pulp bleaching; * Rust-remover for Metal treatment; * Grinding agent, such as Marble polishing; * Waste water treatment, removing calcium from water.
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