6153-56-6

Basic information

• Product Name: Oxalic acid dihydrate
• Synonyms: Oxalsαure-dihydrat;ETHANEDIOIC ACID;ETHANEDIOIC ACID DIHYDRATE;ETHANEDIONIC ACID DIHYDRATE;Ethanedioic acid,Dicarboxylic acid ;OXALIC ACID DIHYDRATE ACS REAGENT;OXALIC ACID DIHYDRATE 99% A.C.S. REAG&;OXALIC ACID DIHYDRATE, 99%, A.C.S. REAGE NT
• CAS NO: 6153-56-6
• Molecular Formula: C₂H₂O₄*2H₂O
• Molecular Weight: 126.07
• EINECS: 205-634-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;C1 to C5;Essential Chemicals;Inorganic Salts;Lipid Library;Metabolic Pathways;Metabolites and Cofactors on the Metabolic Pathways Chart;Reagent Plus;Research Essentials;Solutions and Reagents;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Lipid;Metabolic Libraries;Metabolomics;Organic Building Blocks;ACS Grade;others
• Mol File: 6153-56-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 104-106 °C(lit.)
• Boiling Point: 108-109°C
• Flash Point: 157°C
• Appearance: Yellow to yellow-green/Powder/Solid
• Density: 1,65 g/cm3
• Vapor Density: 4.4 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Storage Temp.: Store at RT.
• Solubility: H2O: soluble1M at 20°C, clear, colorless
• Water Solubility: 138 g/L (20 ºC)
• Stability: Stable. Incompatible with bases, acid chlorides, steel, silver, silver compounds, moisture. Avoid contact with metals.
• Merck: 14,6911
• BRN: 3679436
• CAS DataBase Reference: Oxalic acid dihydrate(CAS DataBase Reference)
• NIST Chemistry Reference: Oxalic acid dihydrate(6153-56-6)
• EPA Substance Registry System: Oxalic acid dihydrate(6153-56-6)

Safety Data

• Hazard Codes: Xn,C
• Statements: 21/22-41
• Safety Statements: 24/25-39-37-36-26
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 1
• RTECS: RO2450000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6153-56-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystals

Uses

Different sources of media describe the Uses of 6153-56-6 differently. You can refer to the following data:
1. Oxalic 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.
2. A diprotic reducing agent used as a buffer.
3. Oxalic 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.

General Description

Oxalic 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.

Reactivity Profile

At high temperatures oxalic acid decomposes, producing toxic carbon monoxide, andformic acid. Mixing with warm sulfuric acidmay produce the same products: CO2, CO,and formic acid. It reacts with many silvercompounds, forming explosive silver oxalate(NFPA 1986). An explosion occurred whenwater was added to an oxalic acid/sodiumchlorite mixture in a stainless steel beaker.There was also evolution of highly toxicchlorine dioxide gas (MCA 1962). Oxalicacid reacts violently with strong oxidizingsubstances.

Health Hazard

Oxalic acid is a strong poison. The toxicsymptoms from ingestion include vomiting, diarrhea, and severe gastrointestinaldisorder, renal damage, shock, convulsions,and coma. Death may result from cardiovascular collapse. The toxicity arises asoxalic acid reacts with calcium in the tissuesto form calcium oxalate, thereby upsettingthe calcium/potassium ratio (ACGIH 1986).Deposition of oxalates in the kidney tubulesmay result in kidney damage (Hodgson et al.1988).Oxalic acid may be absorbed into the bodythrough skin contact. It is corrosive to theskin and eyes, producing burns. Dilute solutions of 10% strength may be a mild irritantto human skin. However, the inhalation toxicity is low because of its low vapor pressure.Airborne dusts can produce eyeburn and irritation of the respiratory tract.LD50 value, oral (rats): 375 mg/kg.

Purification Methods

Crystallise oxalic acid from distilled water. Dry it in a vacuum over H2SO4. The anhydrous acid can be obtained by drying at 100o overnight. [Beilstein 2 IV 1819.]

InChI:InChI=1/C2H2O4.2H2O/c3-1(4)2(5)6;;/h(H,3,4)(H,5,6);2*1H2

Synthetic route

sodium oxalate (62-76-0) → oxalic acid dihydrate (6153-56-6)

Conditions	Yield
With hydrogenchloride; water at 80℃; for 1h; Product distribution / selectivity;	56%

cis-{Pt(PMe3)2(OH)2}*nH2O (n=2-3) + oxalic acid dihydrate (6153-56-6) → {Pt(PMe3)2(ox)} (94929-01-8)

Conditions	Yield
In not given	100%

4,4'-bipyridine (553-26-4) + iron(II) bromide hexahydrate + oxalic acid dihydrate (6153-56-6) → (2).infin.[Fe(oxalate)(4,4'-bipyridine)] (226401-77-0)

Conditions	Yield
In water byproducts: HBr, H2O; molar ratio Fe:oxalate:bipy:H2O=1:1:1:444, digestion bomb, 170°C,7 d; washing (water, Me2CO), drying in air;	99%

4,4'-bipyridine (553-26-4) + cobalt(II) bromide hexahydrate + oxalic acid dihydrate (6153-56-6) → (2).infin.[Co(oxalate)(4,4'-bipyridine)] (226401-78-1)

Conditions	Yield
In water byproducts: HBr, H2O; molar ratio Co:oxalate:bipy:H2O=1:1:1:444, digestion bomb, 170°C,7 d;	99%

1,4-bis(3-aminopropyl)piperazine (7209-38-3) + iron(III) chloride hexahydrate + phosphoric acid (86119-84-8, 7664-38-2) + water (7732-18-5) + oxalic acid dihydrate (6153-56-6) → H3NC3H6NHC4H8NHC3H6NH3(4+)*3Fe(3+)*2C2O4(2-)*3HPO4(2-)*PO4(3-)*100H2O=C10H28N4[Fe3(C2O4)2(HPO4)3(PO4)(H2O)]*99H2O

Conditions	Yield
In water High Pressure; mixt. of FeCl3*6H2O, H2C2O4*2H2O, H3PO4, 1,4-bis(3-aminopropyl)piperazine, and water (pH 4.6) heated at 120°C for 3 d in Teflon-lined stainless-steel Parr acid digestion bomb, slow cooling at 5°C/h to room temp.;	99%

5-hydroxy-6-methyl-3,4-pyridinedimethanol (65-23-6) + boric acid (11113-50-1) + oxalic acid dihydrate (6153-56-6) → [B(oxalato)(pyridoxine(-H))]

Conditions	Yield
In toluene byproducts: H2O; boric acid, pyridoxine and oxalic acid*2H2O in 1:1:1 molar ratio refluxed in toluene during 6 h under continuous sepn. of react. water; filtered; dried at 120°C; elem. anal.;	99%

oxalic acid dihydrate (6153-56-6) + tetrabutyl ammonium methoxide (34851-41-7) → bis(tetrabutylammonium)oxalate (33081-83-3)

Conditions	Yield
In methanol for 4h;	98%

indium(III) oxide + phosphoric acid (86119-84-8, 7664-38-2) + oxalic acid dihydrate (6153-56-6) + 1,4-diaminobutane (110-60-1) → (1,4-diaminobutane(+2H))0.5*In(HPO4)(H2PO4)(oxalate)0.5

Conditions	Yield
In water at 150℃; for 168h; Autoclave;	95%

oxalic acid dihydrate (6153-56-6) + 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonylglycylglycylglycyl)-α-D-glucopyranose (75719-86-7) → 1-O-(glycylglycylglycyl)-α-D-glucopyranose mono-oxalate (75719-99-2)

Conditions	Yield
With hydrogen; palladium on activated charcoal In 2-methoxy-ethanol; acetic acid for 24h;	92%

oxalic acid dihydrate (6153-56-6) + 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-β-D-glucopyranose (75719-88-9) → 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate (75720-06-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In 2-methoxy-ethanol; acetic acid for 20h;	92%

N-phenylbenzohydroxamic acid (304-88-1) + boric acid (11113-50-1) + oxalic acid dihydrate (6153-56-6) → {C6H5CON(C6H5)O}{O(O)CC(O)O}B (87285-07-2)

Conditions	Yield
In benzene heating under reflux for 6 h; evapn. of solvent, crystd. with petroleum ether several times, elem. anal.;	92%

oxalic acid dihydrate (6153-56-6) + zinc(II) acetate dihydrate (5970-45-6) → zinc oxalate dihydrate

Conditions	Yield
In ethylene glycol byproducts: acetic acid, H2O; oxalic acid added slowly with stirring to soln. of zinc acetate at room temp. for 12 h; filetred, washed (acetone) several times, dried at 120°C; XRD;	92%
In methanol byproducts: acetic acid, H2O; oxalic acid added slowly with stirring to soln. of zinc acetate at room temp. for 12 h; filetred, washed (acetone) several times, dried at 120°C; XRD;	90%

uranyl nirate hexahydrate + ammonium hydroxide + oxalic acid dihydrate (6153-56-6) → ammonium dioxoperoxy(oxalato)uranate(VI) hydrate

Conditions	Yield
With water; dihydrogen peroxide In water to soln. of UO2(NO3)2*6H2O added soln. of NH4OH with stirring; filtered; to aq. suspn. added C2O4H2*2H2O and stirred for 5 min; excess of 30% H2O2 added and stirred for 15 min; soln. of NH4OH added (pH = 6); ethanol added; centrifuged; washed with ethanol; dried in vacuo; elem. anal.;	91%

Cu(acetylacetonate)(triphenylphosphine)2 + oxalic acid dihydrate (6153-56-6) → {Cu2(μ-C2O4)(PPh3)4}

Conditions	Yield
In methanol; dichloromethane byproducts: acetylacetone; react. mixt. (molar ratio Cu-complex:oxalic acid = 1:0.5) stirred for 24 h at room temp. in CH2Cl2/MeOH (10:1); filtration, evapn. to dryness; extn. of the residue with CH2Cl2; addn. of Et2O; elem. anal., mol. weight measurement;	90%

tetrakis(hydroxylamine)-platinum(II) hydroxide + oxalic acid dihydrate (6153-56-6) → trans-tetrahydroxylaminodioxalatoplatinum(IV)

Conditions	Yield
With dihydrogen peroxide In water addn. of 30% H2O2 to H2C2O4*2H2O in H2O; (Pt(NH2OH)4)(OH)2 was added in portions to the soln.; standing in the dark for 72 h; mechanism discussed;; filtration through a glass filter; the ppt. was washed with cold H2O, acetone, and ether, and dried in air; elem. anal.;;	90%

trimethyl phosphite (512-56-1) + potassium tetranitroplatinate(IV) + oxalic acid dihydrate (6153-56-6) → 4K(1+)*Pt4(6+)*4NO2(1-)*C2O4(2-)*4OH(1-)*2(CH3O)3PO=K4{Pt4(NO2)4(C2O4)(OH)4}*2(CH3O)3PO

Conditions	Yield
In further solvent(s) trimethylphosphate is added to Pt complex, mixt. is carefully heated at 180-200°C until sample dissolves, cooling to room temp., filtn., addn. of oxalic acid under stirring; ppt. is filtered, washed (CHCl3/EtOH), elem. anal.;	90%

potassium tetranitroplatinate(IV) + oxalic acid dihydrate (6153-56-6) → 2K(1+)*Pt(NO2)2(HC2O4)2(2-)=K2{Pt(NO2)2(HC2O4)2}

Conditions	Yield
With (CH3O)3PO In further solvent(s) trimethylphosphate is added to Pt complex, mixt. is carefully heated at 140-160°C until sample dissolves, cooling to room temp., filtn., addn. of oxalic acid under stirring, react. time 2-5 h; ppt. is filtered, washed (cold H2O/EtOH), elem. anal.;	90%

potassium tetranitroplatinate(IV) + oxalic acid dihydrate (6153-56-6) → 2K(1+)*Pt(NO2)3(HC2O4)(2-)=K2{Pt(NO2)3(HC2O4)}

Conditions	Yield
With (CH3O)3PO In further solvent(s) trimethylphosphate is added to Pt complex, mixt. is carefully heated at 100-120°C until sample dissolves, cooling to room temp., filtn., addn. of oxalic acid under stirring, react. time 2-5 h; ppt. is filtered, washed (H2O/EtOH), elem. anal.;	90%

oxalic acid dihydrate (6153-56-6) + dichlorodiethylstannane (866-55-7) → 2C2H5(1-)*Sn(4+)*(COO)2(2-)*H2O=(C2H5)2Sn(C2O4)*H2O

Conditions	Yield
In water slow pouring acid soln. to soln. of Sn-compd. (stirring); after 1 h ppt. filtration off; elem. anal.;	90%

water (7732-18-5) + vanadia + oxalic acid dihydrate (6153-56-6) → V2O2(4+)*2OH(1-)*C2O4(2-)*2H2O=V2O2(OH)2(C2O4)*2H2O

Conditions	Yield
With H3BO3 In water High Pressure; V2O5, H2C2O4*2H2O, H3BO3 and H2O mixed in a molar ratio 1:14:29:151, heated in an autoclave at 155°C for 20 d; cooled to room temp.(5°C/h), filtered, washed (H2O), dried at room temp., elem. anal.;	90%

4-amino-1,2,4-triazole (584-13-4) + ferrous(II) sulfate heptahydrate + oxalic acid dihydrate (6153-56-6) → [Fe(μ-ox)(4-amino-1,2,4-triazole)2]n

Conditions	Yield
In water soln. (10 ml) of H2C2O4*2H2O (0.2 mmol) added dropwise to soln. (25 ml) of (C2H2N3)NH2 (1.00 mmol) and FeSO4*7H2O (0.2 mmol); ppt. sepd.; washed with cold H2O and Et2O; dried in air; elem. anal.;	90%

4-amino-1,2,4-triazole (584-13-4) + oxalic acid dihydrate (6153-56-6) + zinc(II) chloride (7646-85-7) → [Zn(μ-ox)(4-amino-1,2,4-triazole)2]n

Conditions	Yield
In water soln. (10 ml) of H2C2O4*2H2O (0.2 mmol) added dropwise to soln. (25 ml) of (C2H2N3)NH2 (1.00 mmol) and ZnCl2 (0.40 mmol); ppt. sepd.; washed with cold H2O and Et2O; dried in air; elem. anal.;	90%

Upstream product

• 62-76-0 sodium oxalate 

Downstream Products

• 100516-90-3 5,8-dihydro-1H-pteridine-2,6,7-trione 
• 494-38-2 acridine orange 
• 82207-69-0 N,N'-bis-(3-dimethylamino-phenyl)-oxalamide 
• 90323-30-1 6-nitro-1-methyl-6-nitroquinoxaline-2,3(1H,4H)-dione 
• 97267-07-7 3-Ethoxy-3-[(2-ethoxyphenoxy)methyl]-1-phenylmethylpyrrolidine Oxalate 
• 16009-94-2 sodium hydrogen oxalate monohydrate 
• 144-62-7 oxalic acid 
• 10049-04-4 chlorine dioxide 
• 814-91-5 copper(II) oxalate 
• 13597-20-1 niobium(V) oxide chloride 
• 64-18-6 formic acid 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 
• 1333-74-0 hydrogen 

Relevant articles and documents

Manufacture of oxalic acid dihydrate

A process for the manufacture of oxalic acid dihydrate in which an aqueous solution of sodium oxalate is contacted with hydrochloric acid and the resulting mixture then cooled to precipitate oxalic acid, followed by optional recovery and recycling of the sodium oxalate and hydrochloric acid into the reaction chamber.

Process for the preparation of hydroxyamines

A process for the production of hydroxyamines of the formula I wherein R1 and R2 independently of one another are H or CH2 OH and R3 is H, C1 -C4 -alkyl or C1 -C4 -hydroxyalkyl comprising reacting an oxo compound with an amine and reducing the resultant ketimine with a reducing agent.