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Ammonium oxalate

Ammonium oxalate is an inorganic compound consisting of ammonium cations and oxalate anions in a 2:1 ratio, with the chemical formula (NH₄)₂C₂O₄.^[1] It typically occurs as a colorless or white, odorless crystalline solid, often in the monohydrate form ((NH₄)₂C₂O₄·H₂O), and is highly soluble in water at approximately 4.5 g/100 mL at 20°C.^[2] The compound has a molecular weight of 124.1 g/mol for the anhydrous form and 142.11 g/mol for the monohydrate, a density of 1.5 g/cm³, and decomposes upon heating at around 70°C without a distinct melting point.^[2]^[3] As a reducing agent and analytical reagent, ammonium oxalate is widely used in laboratory settings to precipitate calcium ions as insoluble calcium oxalate for quantitative analysis of calcium in samples.^[4] In soil science, it serves to extract iron and aluminum from poorly crystalline minerals, aiding in geochemical assessments.^[5] Industrially, it finds applications in textile and leather processing, metal polishing and rust removal, electrolytic detinning of iron, and the manufacture of safety explosives and other oxalates.^[1] Ammonium oxalate is considered hazardous, being harmful if swallowed due to its potential to disrupt calcium balance and affect the kidneys, and it acts as an irritant to the skin, eyes, and respiratory tract.^[2] It reacts with strong oxidants and may form combustible dust in air, necessitating careful handling with protective equipment and storage away from incompatible materials.^[2] Despite its toxicity, its role in precise analytical and industrial processes underscores its importance in chemistry and materials science.^[5]

Physical and chemical properties

Physical characteristics

Ammonium oxalate typically exists as a monohydrate, (NH₄)₂C₂O₄·H₂O, appearing as a colorless or white, odorless crystalline powder or solid.^[6]^[7]^[2] The monohydrate form has a molar mass of 142.11 g/mol and a density of 1.50 g/cm³.^[7]^[8] It does not melt upon heating but undergoes initial incomplete decomposition in the range of 105–130 °C, with rapid decomposition initiating around 215 °C and completing by 265 °C, releasing gases such as ammonia, carbon monoxide, carbon dioxide, and water vapor.^[8]^[7]^[9]^[10] Ammonium oxalate monohydrate exhibits high solubility in water, approximately 4.5 g per 100 mL at 20 °C, while it is only slightly soluble in ethanol and insoluble in diethyl ether.^[6]^[8]^[11] The crystal structure of the monohydrate is orthorhombic, belonging to the space group P2₁2₁2₁, characterized by hydrogen-bonded networks involving ammonium ions, oxalate ions, and water molecules.^[12]^[13] Thermodynamically, the standard enthalpy of formation (ΔH_f°) for ammonium oxalate monohydrate is -1425.5 kJ/mol.^[14]

Chemical reactivity

Ammonium oxalate is stable under normal storage and handling conditions, remaining unchanged at room temperature in dry environments.^[15] However, it decomposes in the presence of strong acids or bases; in strong acidic media, the oxalate component can protonate and release carbon dioxide, while in strong basic conditions, hydrolysis occurs gradually, leading to the formation of ammonia and oxalate species.^[7] Upon heating, ammonium oxalate undergoes thermal decomposition, releasing ammonia gas (NH₃), carbon monoxide (CO), carbon dioxide (CO₂), and water vapor (H₂O). The overall reaction for the monohydrate can be represented as:

\ce{(NH4)2C2O4 \cdot H2O -> 2NH3 + CO + CO2 + 2H2O}

This process typically initiates around 215°C and completes by 265°C, with the gaseous products confirming the breakdown of both the ammonium and oxalate moieties.^[8]^[7]^[10] In aqueous solutions, ammonium oxalate undergoes complete dissociation into ammonium cations (NH₄⁺) and oxalate anions (C₂O₄²⁻), as expected for an ionic salt of a weak acid and weak base. Subsequent partial hydrolysis occurs, where the oxalate ion acts as a weak base (derived from oxalic acid with pKₐ values of 1.25 and 4.14) and the ammonium ion as a weak acid (pKₐ = 9.25), resulting in a near-neutral pH solution around 6.5–7.0.^[16]^[1] The compound exhibits reducing properties primarily due to the oxalate ion, which can donate electrons in redox reactions, often generating carbon dioxide as a byproduct; for instance, it reacts rapidly with oxidizing agents like sodium hypochlorite.^[1] Ammonium oxalate participates in precipitation reactions with various metal ions to form insoluble oxalates, such as calcium oxalate (CaC₂O₄) upon addition to solutions containing Ca²⁺, a key step in qualitative inorganic analysis for identifying calcium.^[1]

Synthesis and production

Laboratory synthesis

Ammonium oxalate is commonly synthesized in the laboratory through the neutralization of oxalic acid with an ammonia solution, typically ammonium hydroxide. The reaction proceeds as follows:

\mathrm{H_2C_2O_4 + 2NH_3 \rightarrow (NH_4)_2C_2O_4}

To perform this synthesis, approximately 0.5 g of oxalic acid is weighed and dissolved in water, then gently heated to around 50°C. Concentrated ammonia solution is added dropwise with stirring, using an indicator such as phenolphthalein to monitor the endpoint until the solution turns pink, indicating neutralization. The mixture is then filtered to remove any undissolved impurities.^[17]^[18] An alternative laboratory method involves reacting oxalic acid with ammonium carbonate. The balanced equation for this process is:

\mathrm{(NH_4)_2CO_3 + H_2C_2O_4 \rightarrow (NH_4)_2C_2O_4 + H_2O + CO_2}

In practice, 100 g of oxalic acid is dissolved in 800 mL of water and gently warmed, followed by the addition of about 83 g of ammonium carbonate until neutralization is achieved, often monitored by pH adjustment to approximately 7 using a pH meter or suitable indicator. Carbon dioxide gas evolves during the reaction, which is vented safely. The solution is filtered, and the filtrate is concentrated by evaporation to promote crystallization.^[11]^[18] Following synthesis by either method, the crude ammonium oxalate is purified by recrystallization from hot water to isolate the monohydrate form, (NH₄)₂C₂O₄·H₂O, as colorless crystals. The solid is dissolved in the minimum volume of boiling water, filtered while hot to remove insoluble impurities, and then slowly cooled to room temperature or below to allow crystal formation. The crystals are collected by filtration, washed with cold water or ethanol, and dried. This step enhances purity by exploiting the compound's solubility, which is higher in hot water than in cold (about 4.3 g/100 mL at 20°C).^[19]^[17] These procedures are typically conducted at room temperature after initial warming, with pH controlled to neutrality (around 7) to ensure complete reaction and avoid excess acidity or basicity. Yields are generally high, ranging from 80-90%, depending on the precision of neutralization and purification steps.^[17]^[11]

Commercial production

Ammonium oxalate is commercially produced on an industrial scale primarily through the neutralization of oxalic acid with ammonia gas or ammonium hydroxide solution in large-scale reactors, following the reaction \mathrm{H_2C_2O_4 + 2NH_3 \rightarrow (NH_4)_2C_2O_4}, with the monohydrate (NH₄)₂C₂O₄ · H₂O formed upon subsequent crystallization, filtration, drying, and optional recrystallization for purification.^[20]^[21] Oxalic acid, the key precursor, is mainly manufactured via microbial fermentation using the fungus Aspergillus niger on carbohydrate substrates such as glucose or sucrose, yielding up to several grams per liter under optimized conditions, though chemical oxidation methods like nitric acid treatment of sodium formate are also employed in some facilities.^[22]^[23] This process is scaled up from laboratory methods but emphasizes continuous reactors and automation for efficiency, often integrated into oxalic acid production plants rather than as a direct byproduct of unrelated ammonia-based processes. Although ammonium oxalate occurs naturally in plants such as rhubarb, sorrel, and spinach, where it forms as a metabolic product, commercial extraction from these sources is limited and not economically viable due to low yields and complex purification requirements.^[1] Historically, processing of guano deposits—rich in nitrogen compounds including ammonium oxalate as the mineral oxammite—provided a source of such salts for fertilizer and chemical applications in the 19th century, but this has been superseded by synthetic methods.^[24] Global production is handled by specialized chemical manufacturers, primarily in regions like India and China, with major suppliers including companies that distribute to industrial and laboratory markets. Commercial ammonium oxalate is available in several purity grades tailored to end-use requirements: technical grade at approximately 98-99% purity for general industrial applications, analytical reagent (AR) grade at ≥99.5% for precise chemical analyses, and trace-metal-free variants at ≥99.99% purity to minimize contamination in sensitive processes.^[1]^[8]^[20] The monohydrate form, (NH₄)₂C₂O₄ · H₂O, predominates in commercial products due to its stability and ease of handling.

Uses

Analytical applications

Ammonium oxalate plays a key role in gravimetric analysis, particularly for the quantitative determination of calcium in various samples. The procedure involves adding a solution of ammonium oxalate to a neutral or slightly acidic sample containing calcium ions, which precipitates as calcium oxalate monohydrate (CaC₂O₄·H₂O), an insoluble compound with low solubility that ensures complete recovery. The white precipitate is then filtered, washed to remove impurities, dried at 100–110°C, and weighed; the mass is used to calculate calcium content based on the stoichiometric ratio. This method achieves high accuracy, with typical recoveries exceeding 99% when performed under controlled conditions to avoid co-precipitation of other ions.^[25]^[26]^[19] Ammonium oxalate is used as an anticoagulant in blood sample collection and preservation, where it binds calcium ions to inhibit the clotting cascade, allowing for analysis of blood components without coagulation.^[27] In qualitative analysis, ammonium oxalate serves as a reagent for detecting specific metals through precipitation reactions. For calcium, it produces a white, crystalline precipitate of calcium oxalate that is insoluble in acetic acid, distinguishing it from other alkaline earth metals like magnesium. Similarly, lead forms a white precipitate of lead(II) oxalate, useful in identifying lead in complex mixtures after separation from interfering ions. For rare earth elements, ammonium oxalate precipitates them as insoluble oxalates, enabling their isolation and subsequent quantification in mineral samples. These tests leverage the selective insolubility of metal oxalates, often performed in ammoniacal solutions to control pH and enhance specificity.^[19]^[28] Ammonium oxalate is also employed in soil science for extracting amorphous and poorly crystalline forms of iron and aluminum oxides, which are critical for understanding soil fertility and mineralogy. The method, known as Tamm's acid ammonium oxalate extraction, uses a buffered solution of 0.2 M ammonium oxalate and 0.2 M oxalic acid adjusted to pH 3.0–3.3, which selectively dissolves these non-crystalline phases without significantly affecting crystalline minerals like goethite or hematite. The extract is analyzed by atomic absorption spectroscopy or inductively coupled plasma to quantify Fe and Al contents, providing insights into pedogenic processes; for example, high oxalate-extractable Fe indicates active weathering in podzolic soils. This technique minimizes interference from organic matter when performed in the dark to prevent photochemical reduction.^[29]^[30] The analytical applications of ammonium oxalate originated in the 19th century, coinciding with the development of systematic gravimetric and qualitative methods in mineral analysis by chemists such as Jöns Jacob Berzelius, who refined precipitation techniques for accurate elemental quantification. By the mid-1800s, oxalate precipitation had become a standard for calcium in geological and biological samples, evolving into modern protocols like Tamm's method in the early 20th century for soil studies.^[31]^[32]^[33]

Industrial applications

Ammonium oxalate serves as a versatile compound in various industrial processes, particularly where its chelating and reducing properties facilitate material treatment and synthesis. In the textile industry, it functions as a mordant to enhance dye fixation on fabrics, improving colorfastness and binding strength during dyeing operations.^[34]^[35] This application leverages its ability to form stable complexes with metal ions, aiding in the even distribution and permanence of dyes on fibers.^[36] In metalworking, ammonium oxalate is incorporated into polishing formulations to remove rust, scale, and oxidation from surfaces, restoring metallic luster through its rust-complexing action.^[37]^[38] It is particularly effective in electrolytic detinning processes for iron and in general metal surface treatments, where it dissolves iron oxides without excessive abrasion.^[39] The compound plays a role in explosives manufacturing as an ingredient in the production of safety explosives and as a burn rate moderator in ammonium-based propellants and detonators.^[27]^[39] Its reducing properties contribute to controlled combustion rates in solid rocket formulations.^[40] Additionally, ammonium oxalate finds application in leather processing as an agent in tanning and treatment stages, helping to stabilize hides and improve finish quality.^[36]^[41] Its chelating effects assist in removing impurities and enhancing the penetration of tanning agents into leather matrices.^[42]

Biological and geological occurrence

Biological role

Soluble oxalates, such as sodium and potassium oxalates, occur naturally in plants, synthesized from oxalic acid. These accumulate particularly in vegetables like spinach (Spinacia oleracea), rhubarb (Rheum rhabarbarum), and sorrel (Rumex acetosa), where they contribute to a defense mechanism against herbivory by deterring feeding through toxicity and crystal formation. In these plants, total oxalate concentrations can reach up to 1% of dry weight, with spinach exhibiting levels as high as 2350 mg per 100 g fresh weight, predominantly as insoluble calcium oxalate but including soluble variants that enhance overall antinutritional effects.^[43]^[44]^[45]^[46] In vertebrates, oxalate is produced endogenously through the metabolism of glyoxylate, a key intermediate derived from pathways such as hydroxyproline degradation or from the breakdown of ascorbic acid (vitamin C). Glyoxylate is primarily converted to oxalate by enzymes like lactate dehydrogenase in the liver and other tissues. This oxalate is not further metabolized but is primarily eliminated via the kidneys, often forming various salts, with normal urinary excretion levels of total oxalate ranging from 10 to 40 mg per day in humans, reflecting a balance between endogenous synthesis and dietary intake.^[47]^[48]^[49] Excess urinary oxalate contributes to the formation of calcium oxalate crystals, a primary component of kidney stones in vertebrates, particularly when excretion exceeds solubility limits influenced by factors like urinary pH and calcium concentration. Ammonium oxalate is not a primary metabolic intermediate in mammals, which detoxify ammonia via the urea cycle. High concentrations of ammonium oxalate are also prominent in guano, the accumulated excrement of birds and bats, arising from their uric acid-based nitrogen metabolism where oxalate combines with ammonium during waste processing. In seabird guano deposits, such as those from Peru, ammonium oxalate comprises up to 17.7% of the composition, while bat guano similarly features elevated levels reaching several percent, supporting nutrient-rich ecological roles in soil formation and fertilization.^[50]^[51]

Mineral forms

Oxammite, with the chemical formula (NH₄)₂C₂O₄·H₂O, is the primary natural mineral form of ammonium oxalate, recognized as an organic mineral derived from guano deposits.^[52] It was first described in 1870 from bird guano in the Virú Province, La Libertad Region, Peru, marking its initial identification in subfossil bird eggs and on subfossil birds.^[53] This rare mineral typically forms through precipitation in ammonia-rich environments created by the decomposition of bat or bird guano under arid conditions, often in caves or dry deposits where organic matter accumulates without significant alteration.^[53] It is commonly associated with other ammonium-bearing minerals such as mascagnite ((NH₄)₂SO₄), reflecting shared origins in guano-derived geochemical systems.^[53] Physically, oxammite occurs as colorless to pale yellow crystals, transparent in transmitted light, with a white streak.^[52] It exhibits distinct cleavage on {001}, belongs to the orthorhombic crystal system, and has a Mohs hardness of 2.5, making it relatively soft.^[54] The specific gravity is measured at 1.5, consistent with its hydrated, low-density structure.^[54] Occurrences of oxammite are exceedingly rare and limited to specific guano-rich sites in arid or cave settings. The type locality remains the Guañape Islands off Peru, with additional verified finds in bat guano at the Murra Mine, Coquimbo Region, Chile, and Cueva de Los Verdes, Lanzarote, Canary Islands, Spain.^[53] It has also been reported from the Mer de Glace cave near Chamonix, France.^[53] As a pre-1959 description, oxammite holds grandfathered status under International Mineralogical Association (IMA) guidelines, without a formal approval process post-1959.^[52] Its biological origin traces to the uric acid breakdown in guano, leading to oxalate formation in hyperarid conditions.^[53]

Health and safety

Toxicity profile

Ammonium oxalate exhibits moderate acute toxicity upon ingestion, with an oral LD50 value of 375 mg/kg in female rats, determined by analogy to similar oxalate compounds.^[55] Exposure can cause gastrointestinal distress, including nausea, vomiting, and abdominal pain, as well as systemic effects such as hypocalcemia leading to muscle cramps and tetany.^[56] In severe cases, it may result in convulsions, coma, or death due to renal impairment from calcium oxalate crystal formation in the kidneys.^[57] Dermal and inhalation routes also pose risks, with potential for irritation and absorption contributing to overall toxicity, though dermal LD50 exceeds 2,000 mg/kg in rats; no specific LD50 is available for inhalation.^[55] Chronic exposure to ammonium oxalate primarily manifests as nephrotoxicity, potentially progressing to renal failure through repeated deposition of calcium oxalate crystals in the renal tubules. It acts as an irritant to the skin, causing redness and dermatitis upon prolonged contact; to the eyes, leading to corneal damage and severe irritation; and to the respiratory tract, where inhalation of dust may induce coughing, shortness of breath, and pulmonary edema in high concentrations.^[56] Long-term effects may also include disruptions in calcium metabolism, exacerbating cardiovascular and neurological issues.^[58] The primary mechanism of toxicity involves oxalate ions chelating calcium to form insoluble calcium oxalate crystals, which precipitate in the kidneys and impair filtration, leading to acute and chronic renal damage.^[57] The ammonium component contributes additional irritation to mucous membranes and respiratory tissues, potentially releasing ammonia upon decomposition and enhancing local corrosive effects.^[55] Solubility in aqueous media facilitates gastrointestinal absorption, influencing the rate of systemic exposure.^[2] Under the Globally Harmonized System (GHS), ammonium oxalate is classified as harmful if swallowed (Acute Toxicity, Oral, Category 4; H302).^[59] No specific OSHA Permissible Exposure Limit (PEL) exists for ammonium oxalate; the general PEL for nuisance dust is 5 mg/m³ (respirable fraction) as an 8-hour time-weighted average.^[56]^[60]

Handling and environmental considerations

Ammonium oxalate should be stored in tightly closed containers in a cool, dry, and well-ventilated area to prevent moisture absorption and potential decomposition, which could release ammonia gas; it must be kept away from incompatible materials such as strong oxidizers, acids, and metals like iron or lead to avoid violent reactions or corrosion.^[61]^[56] Safe handling requires the use of personal protective equipment, including nitrile rubber gloves, safety goggles, and protective clothing to prevent skin and eye contact; respiratory protection with a P2 filter is recommended when dust is generated to avoid inhalation, and work should be conducted under a fume hood. In case of exposure, first aid measures include immediately flushing affected eyes or skin with plenty of water for at least 15 minutes and removing contaminated clothing, while ingestion necessitates rinsing the mouth, drinking water if conscious, and seeking immediate medical attention.^[61]^[56] For spills, the area should be evacuated, ventilated, and the material collected using non-sparking tools into sealed containers for disposal, followed by washing the site with water; disposal must follow local, state, and federal regulations, treating it as hazardous waste due to its toxicity, potentially under the Resource Conservation and Recovery Act (RCRA) if it exhibits characteristic hazards, without allowing entry into sewers or waterways.^[56]^[62] Environmentally, ammonium oxalate has low persistence in soil due to rapid microbial biodegradation, with up to 89% degradation observed within 20 days, primarily through oxalotrophic bacteria and fungi that mineralize oxalate to carbon dioxide; however, its high solubility allows leaching of oxalate ions into groundwater and surface waters, where it may affect aquatic organisms by chelating metals and altering bioavailability, though acute toxicity is relatively low (EC50 >33 mg/L for Daphnia magna).^[61]

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[51]
(PDF) Guano: The White Gold of the Seabirds - ResearchGate
The term "Guano" applies to natural mineral deposits consisting of excrements, eggshells and carcasses of dead seabirds found in almost rainless, hot-dry ...
[52]
Phoxite, (NH 4 ) 2 Mg 2 (C 2 O 4 )(PO 3 OH) 2 (H 2 O) 4 , the first ...
Jul 1, 2019 · Bat guano is generally rich in ammonium oxalate (and urate) and phosphates, as well as cations such as K, Na, Ca, Mg, and Fe. Clearly, the new ...
[53]
Oxammite: Mineral information, data and localities.
Sep 20, 2025 · An organic mineral derived from guano; in sub-fossil bird eggs and on sub-fossil birds.Missing: formation | Show results with:formation
[54]
[PDF] Oxammite (NH4)2C2O4 • H2O - Handbook of Mineralogy
Occurrence: Derived from bird or bat guano; in subfossil bird eggs and on subfossil birds. Association: Mascagnite (Gua˜nape Islands, Peru). Distribution ...
[55]
https://www.sigmaaldrich.com/IN/en/sds/aldrich/379743
[56]
https://www.nj.gov/health/eoh/rtkweb/documents/fs/0108.pdf
[57]
[PDF] 0108 - Hazardous Substance Fact Sheet
headache, dizziness, nausea and vomiting, convulsions, coma and even death. ▻ Ammonium Oxalate may affect the kidneys. Workplace Exposure Limits. No ...
[58]
https://employees.delta.edu/facilities/_safety-data-sheets/ammonium-oxalate-j-t-baker.pdf
[59]
[PDF] ammonium-oxalate-j-t-baker.pdf
Although not a listed RCRA hazardous waste, this material may exhibit one or more characteristics of a hazardous waste and require appropriate analysis to ...
[60]
Substance Information - ECHA
### Toxicity Information for Ammonium Oxalate Monohydrate
[61]
None
### Summary of Ammonium Oxalate (Aldrich - 379743) Safety Data Sheet
[62]
40 CFR § 302.4 - Hazardous substances and reportable quantities.
Ammonium oxalate, 6009-70-7 5972-73-6 14258-49-2, 1, 5000 (2270). Ammonium ... waste classified as hazardous under subpart D of 40 CFR part 261. (Leachate ...