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Oxalic acid dihydrate

HCID 61373
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Basic information

CAS
6153-56-6
Standard SMILES
O.O.O=C(O)C(=O)O
InChIKey
GEVPUGOOGXGPIO-UHFFFAOYSA-N
Molecular formula
C2H2O4.2H2O
Average molar mass
126.07 g/mol
Monoisotopic mass
126.01643791

Overview

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.

Names & identifiers

Preferred name
Oxalic acid dihydrate
IUPAC
oxalic acid;dihydrate
English name
Oxalic acid dihydrate
Molecular formula
C2H6O6
Molecular weight
126.07

Names & synonyms

Oxalic acid dihydrate6153-56-6Ethanedioic acid, dihydrateETHANEDIOIC ACID DIHYDRATE0K2L2IJ59OOXALICUM ACIDUMDTXSID2075003VARROMED COMPONENT OXALIC ACID DIHYDRATERefChem:1093935DTXCID8043070612-167-2Oxalic acid, dihydrate
Show more names
ETHANEDIOIC ACIDOxalate AcidOXALIC ACID 2H2OOXALIC ACID 2HYD XTLKH2PO56Has two acidOxalicAcidGrOXALIC ACID PUREACS, 99.5-102.5%
MFCD00149102OXALIC ACID (1,2-13C2)UNII-0K2L2IJ59OOxalicaciddihydrateoxalicacid dihydratedihydrate oxalic acidoxalic acid di-hydrateOXALIC ACID, ACS

Database identifiers

CAS
6153-56-6
PubChem CID
61373
DTXSID
DTXSID2075003
ChEMBL
CHEMBL5315063
UNII
0K2L2IJ59O
EC Number
612-167-2

Properties

Computed structural properties

Topological polar surface area
76.6 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
8
Formal charge
0
Complexity
71.5

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids
FragrancesFragrance Ingredient (Oxalic acid dihydrate) -> IFRA transparency List
LogP-0.81
Density · 2 items

1.65 g/cm³

1.653 @25 °C

SolubilitySolubility in water, g/100ml at 20 °C: 13-14
Animal Drugs · 2 items

EMA approved medicines: Veterinary medicine

EMA approved medicines: Veterinary medicine

Melting Point · 2 items

101-102 °C

189.5 °C

Vapor Pressure0.54 [mm Hg] @105 °C
Physical Description · 3 items

Large Crystals; Dry Powder; Other Solid; Liquid; Liquid; Other Solid

Colorless solid; [ICSC] Colorless hygroscopic crystals; [Sigma-Aldrich MSDS]

COLOURLESS CRYSTALS.

Physicochemical properties

Melting point
104 · 104-106 °C(lit.)
Boiling point
108 · 108-109°C
bulk density
813 kg/m3 · 813kg/m3
Density
1 · 1,65 g/cm3
vapor density
4.4 · 4.4 (vs air)
vapor pressure
0.01 mm · <0.01 mm Hg ( 20 °C)
Flash point
157 °C · 157°C
storage temp.
5 °C · Store at +5°C to +30°C.
solubility
2 O: · H2O: soluble1M at 20°C, clear, colorless
form
Powder/Solid
Specific Gravity
1.65 · 1.65
color
Yellow to yellow-green
PH
1 · ~1.0 (25℃, 1M in H2O)
PH Range
6 · 6 - 8 at 25 °C
Water Solubility
138 g/L · 138 g/L (20 ºC)
Sublimation
157 · 157 ºC
Merck
14 · 14,6911
BRN
3679436 · 3679436
Exposure limits
1 mg/m3;TLV-STEL:2 · ACGIH TLV-TWA:1 mg/m3;TLV-STEL:2 mg/m3OSHA PEL-TWA:for anhydrous acid 1 mg/m3
Stability
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 DataBase Reference
6153 · 6153-56-6(CAS DataBase Reference)
FDA UNII
0 K2L2IJ59O · 0K2L2IJ59O
NIST Chemistry Reference
Oxalic acid dihydrate(6153-56-6)
EPA Substance Registry System
Oxalic acid dihydrate (6153-56-6)
Absorption
303 nm · cut-off at 303nm in H2O at 1M
UNSPSC Code
41116107 · 41116107
NACRES
25 · NA.25
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302+H312-H318
Precautionary statements
264 · P264-P270-P280-P301+P312-P302+P352+P312-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,C
Risk Statements
21 · 21/22-41
Safety Statements
24 · 24/25-39-37-36-26
RIDADR
3261 · UN 3261 8/PG 3
WGK Germany
1 · 1
RTECS
2450000 · RO2450000
TSCA
Yes
HazardClass
8 · 8
PackingGroup
III
HS Code
29171100 · 29171100
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1
Toxicity
50 orally · LD50 orally in Rabbit: 375 mg/kg

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 3 items

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

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Hazards Summary · 1 item

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.

EC ClassificationSymbol: Xn; R: 21/22; S: (2)-24/25
UN ClassificationUN Hazard Class: 8; UN Pack Group: III
Chemical Dangers · 1 item

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.

Packaging and LabellingDo not transport with food and feedstuffs.
Hazard Classes and Categories · 2 items

Acute Tox. 4 (98.8%)

Acute toxicity - category 4

Safety & protection

Fire FightingUse water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 items

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.

Safe StorageSeparated from strong oxidants and food and feedstuffs.
Spillage Disposal · 1 item

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.

Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
Skin PreventionProtective gloves. Protective clothing.
Exposure PreventionPREVENT DISPERSION OF DUST!
Ingestion PreventionDo not eat, drink, or smoke during work. Wash hands before eating.
Inhalation PreventionUse ventilation (not if powder), local exhaust or breathing protection.
Threshold Limit Values (TLV) · 3 items

1.0 [mg/m3]

2.0 [mg/m3]

1 mg/m

Toxicology

Treatment · 1 item

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 · 1 item

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.

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion. Serious local effects by all routes of exposure.
Toxicity Summary · 1 item

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 · 5 items

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.

Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
1
tsca
Yes
rtecs
RO2450000
ridadr
UN 3261 8/PG 3
hs_code
29171100
Toxicity
LD50 orally in Rabbit: 375 mg/kg
risk_code
21/22-41
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
Xn,C
safety_code
24/25-39-37-36-26
hazard_class
8
Storage Class
11 - Combustible Solids
packing_group
III
Hazard statements
H302+H312-H318
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1
Precautionary statements
P264-P270-P280-P301+P312-P302+P352+P312-P305+P351+P338

Chemistry & industry

Pharmacology

Metabolism/MetabolitesOxalic acid is not metabolized but excreted in the urine.

Uses & manufacturing

Uses · 3 items

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)

U.S. Production2023: 2,500,000 - <4,000,000 lb
Consumer UsesBleaching agent
Industry UsesPlating agent
Household ProductsInformation on 42 consumer products that contain Oxalic acid dihydrate in the following categories is provided:
Use ClassificationFragrance Ingredients
General Manufacturing InformationNot Known or Reasonably Ascertainable
Applications · 4 items

UsesA diprotic reducing agent used as a buffer.

UsesOxalic acid occurs in the cell sap of Oxalisand Rumex species of plants as the potassium and calcium salt. It is the metabolicproduct of many molds (Merck 1989). Thereare a large number of applications of thiscompound, including indigo dyeing; calicoprinting; removal of paint, rust, and inkstains; metal polishing; bleaching leather; inpesticide compositions and manufacture ofoxalates. It is also used as an analyticalreagent and as a reducing agent in organicsynthesis.Addition of oxalic acid to chromic acid forthe anodizing of Al alloy has been reported tomodify the morphology and improve the corrosion performance of anodic films (Moutarlier et al. 2004). Also, it is a very effectiveadditive for the ozone treatment of cellulose.It prevents the degradation of cellulose fromozone bleaching.

UsesOxalic 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.

General DescriptionOxalic acid dihydrate (OAD) crystals are reported to be monoclinic with P21/n space group. The electron density of OAD has been obtained using X-ray diffraction studies under high resolution.

Upstream & downstream products

Upstream raw materials

Nitric oxideEthylene glycolSodium oxalate

Downstream products

Oxalic acidVanadyl acetylacetonateN,N,N',N'-Tetramethylethylenediamine1-Isopropyl-5-hydroxypyrazolNICKEL OXALATE DIHYDRATE2,3-Dihydroxyquinoxaline-6-carboxylic acid
Additional notes · 1 item

DefinitionOxalic acid dihydrate (OAD) which has very high initial phase transition enthalpy is a promising phase change material (PCM). This compound is low manufacturing cost and wide usage. In OAD, alternating acid and water molecules that act both as hydrogen-bond donors and acceptors. OAD needs a lot of energy to break the hydrogen-bond in the melting process. Therefore, OAD has a very high heat of fusion of 370 J·g-1,which is a very promising PCM in TES for applications such as industrial waste heat recovery or solar energy storage systems[1].

Related reactions

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HRID 787As reactantuspto-grants-1998_03
HRID 35000 reaction equation
HRID 35000As reactantuspto-grants-1988_08
HRID 35008 reaction equation
HRID 35008As reactantuspto-grants-1988_08
HRID 35010 reaction equation
HRID 35010As reactantuspto-grants-1988_08
HRID 36918 reaction equation
HRID 36918As reactantuspto-grants-1995_05
HRID 37032 reaction equation
HRID 37032As reactantuspto-grants-1995_05
HRID 37033 reaction equation
HRID 37033As reactantuspto-grants-1995_05
HRID 53358 reaction equation
HRID 53358As reactantuspto-grants-1997_04
Page 1 of 43

Compound notes

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