Fact-checked by Grok 2 weeks ago

Sodium methoxide

Sodium methoxide, also known as sodium methylate, is an inorganic compound with the chemical formula CH₃ONa and a molecular weight of 54.02 g/mol.^[1] It exists as a white, amorphous, hygroscopic powder that decomposes at 127 °C and is highly reactive, igniting spontaneously in moist air and reacting violently with water to form sodium hydroxide and methanol.^[1] As a strong base, it serves as a versatile reagent and catalyst in various chemical processes.^[1] In organic synthesis, sodium methoxide is commonly employed for deprotection reactions, such as de-O-acetylation of carbohydrates, and for promoting transesterification of esters, including the preparation of fatty acid methyl esters for chromatographic analysis.^[2] Industrially, it acts as a key catalyst in biodiesel production through the methanolysis of vegetable oils and animal fats, enabling the conversion of triglycerides into fatty acid methyl esters and glycerol.^[3]^[4] Additionally, it finds applications in the processing of edible fats and oils, as well as in the manufacture of pharmaceuticals and other fine chemicals.^[5]^[6] Due to its corrosive nature, sodium methoxide causes severe skin burns, eye damage, and respiratory irritation upon contact or inhalation, and it is highly flammable, necessitating careful handling under inert atmospheres or in alcoholic solutions to mitigate risks.^[1]^[7] It is typically prepared by reacting sodium metal with methanol and is commercially available as a solid or in methanolic solutions for practical use.^[1]

Chemical identity and properties

Nomenclature and formula

Sodium methoxide, with the systematic IUPAC name sodium methanolate, is a chemical compound belonging to the class of metal alkoxides.^[1] The name "methoxide" derives from the methoxide anion (CH₃O⁻), which is the deprotonated form of methanol, combined with the sodium cation, following the general nomenclature for alkoxides as metal derivatives of alcohols where the alkyl group is attached to oxygen.^[8] Its molecular formula is CH₃ONa or equivalently NaOCH₃.^[1] Common synonyms include sodium methoxide, sodium methylate, and methoxysodium.^[1] The compound has a molar mass of 54.02 g/mol and is identified by the CAS number 124-41-4.^[1] It serves as the sodium salt of methanol.^[1]

Physical properties

Sodium methoxide appears as a white to off-white hygroscopic powder or crystalline solid, often described as amorphous or tetragonal in form.^[1] It has a melting point of approximately 127 °C, at which it decomposes without fully melting, and has no boiling point as the solid decomposes upon heating.^[1] The density of the solid varies depending on measurement conditions and form, typically ranging from 1.0 to 1.3 g/cm³, with apparent or packing densities as low as 0.45–0.60 g/mL.^[1]^[9] Sodium methoxide exhibits high solubility in polar solvents such as methanol and ethanol, with solubility exceeding 100 g/100 mL in methanol at 20 °C; it is insoluble in nonpolar hydrocarbons like hexane and reacts violently with water.^[1] Its vapor pressure is negligible at room temperature due to its solid state and low volatility.^[9] The heat capacity of the solid is approximately 65 J/mol·K at 298 K.^[10] Common commercial solutions, such as 25–30 wt% in methanol, have a density of about 0.94–0.97 g/mL at 25 °C and a flash point of 11–16 °C.

Structural features

Sodium methoxide is an ionic compound composed of sodium cations (Na⁺) and methoxide anions (CH₃O⁻). The methoxide anion (CH₃O⁻) exhibits a C–O bond length of approximately 1.42 Å, with the carbon atom displaying tetrahedral geometry due to its sp³ hybridization.^[12] In the solid state, sodium methoxide adopts a polymeric structure with a tetragonal unit cell (a = 4.34 Å, c = 7.43 Å), forming sheet-like layers where sodium atoms lie in planes and are coordinated to four oxygen atoms from methoxide groups above and below, resulting in a distorted tetrahedral coordination geometry around each Na⁺ (Na–O distances ~2.3–2.4 Å).^[13]^[14] In solution, sodium methoxide exists primarily as solvated ions, appearing monomeric in polar protic solvents like methanol, while it may form dimeric or higher oligomeric species in less coordinating solvents.^[15] Spectroscopic techniques confirm these structural features: infrared spectroscopy shows characteristic C–O stretching bands at approximately 1070–1088 cm⁻¹, while ¹H NMR in deuterated methanol displays the methyl protons at ~3.3 ppm and ¹³C NMR the carbon at ~50 ppm.^[16]^[17] Compared to other sodium alkoxides, such as sodium ethoxide, sodium methoxide shares a similar polymeric solid-state arrangement with tetrahedral Na⁺ coordination but features shorter alkyl chains on the anion, which influence its higher solubility in polar solvents.^[14]

Preparation

Laboratory synthesis

Sodium methoxide is commonly prepared in the laboratory by reacting sodium metal with anhydrous methanol under an inert atmosphere to prevent side reactions with moisture or oxygen.^[16] The balanced chemical equation for this reaction is:

$2 \mathrm{Na} + 2 \mathrm{CH_3OH} \rightarrow 2 \mathrm{CH_3ONa} + \mathrm{H_2}

This process is highly exothermic and must be conducted with careful temperature control to avoid ignition.^[18] In a typical procedure, small pieces of freshly cut sodium metal are added slowly to excess anhydrous methanol cooled in an ice bath, under a nitrogen or argon atmosphere. The addition generates hydrogen gas, which is vented safely, and the mixture is then refluxed gently to ensure complete reaction. Once the sodium has fully dissolved, the solution can be used directly or the excess methanol evaporated under reduced pressure to isolate the white solid product, followed by filtration if necessary.^[19] An alternative laboratory route involves treating sodium hydride with anhydrous methanol:

\mathrm{NaH} + \mathrm{CH_3OH} \rightarrow \mathrm{CH_3ONa} + \mathrm{H_2}

This method also evolves hydrogen gas and proceeds under inert conditions but is less frequently employed due to the higher cost and availability of sodium hydride compared to sodium metal.^[20] Laboratory syntheses of this type typically afford yields of 90–95%, with the product purified by recrystallization from hot methanol to remove impurities and obtain high-purity crystals.^[21] These methods were refined in the early 20th century to support precise applications in organic synthesis, as documented in contemporary procedures.^[22]

Commercial production

The primary industrial production of sodium methoxide involves the anhydrous reaction of sodium metal with methanol in large-scale stirred reactors under inert atmospheres to prevent oxidation.^[23] The highly exothermic reaction generates hydrogen gas as a byproduct and sodium methoxide dissolved in excess methanol, which is subsequently purified by distillation to remove unreacted methanol while venting or capturing the hydrogen.^[24] This method dominates due to its efficiency and scalability, with the reaction conducted in stainless steel or specialized alloy reactors equipped for heat management and gas handling.^[25] Global production volume for sodium methoxide was approximately 1,467,000 tons in 2024, driven largely by demand in biodiesel and chemical synthesis sectors.^[26] Major producers are concentrated in China, which accounts for a significant share due to its expansive chemical manufacturing base, and the United States, where companies like American Elements operate facilities.^[27] Other key players include Evonik Industries and BASF, with capacity expansions in 2024 such as Evonik's increase to 90,000 tons annually in Argentina and BASF's to 90,000 tons in Brazil.^[28]^[29] The exothermic nature of the sodium-methanol reaction minimizes external energy inputs, enhancing cost-effectiveness, while the hydrogen byproduct is often captured and utilized as a fuel source to improve overall process efficiency.^[30] Alternative production routes include the reaction of sodium hydroxide with methanol under dehydrating conditions, such as using molecular sieves or azeotropic distillation to shift the equilibrium toward sodium methoxide formation, though this method requires additional energy for water removal.^[31] Less common due to the toxicity of dimethyl sulfate is its use in methylating sodium hydroxide to form sodium methyl sulfate intermediates, which are then processed to sodium methoxide, but environmental concerns limit adoption.^[32] Electrochemical methods, such as electrodialysis of sodium chloride in methanolic solutions or ceramic ion-conducting membranes, offer potential greener alternatives by avoiding sodium metal, though they remain niche due to higher capital costs.^[33]^[34] For commercial handling and transport, sodium methoxide is typically produced and supplied as 25–30% solutions in methanol, which reduces flammability risks compared to pure forms and facilitates safer logistics via tankers or drums.^[35] In the 2020s, industry trends have shifted toward more sustainable processes, including those utilizing sodium hydroxide from chloralkali byproducts to minimize reliance on energy-intensive sodium metal production.^[23]

Chemical reactivity

Basicity and nucleophilicity

Sodium methoxide functions primarily as a source of the methoxide anion (CH₃O⁻), which is a strong base due to the relatively high pKa of its conjugate acid, methanol. In aqueous media, the pKa of methanol is approximately 15.5, indicating that methoxide is a moderately strong base comparable to hydroxide (pKa of water ≈15.7). However, in non-aqueous solvents like dimethyl sulfoxide (DMSO), the pKa shifts to about 29, reflecting significantly greater basic strength because aprotic solvents poorly solvate the anion through hydrogen bonding, thereby enhancing its availability for proton abstraction. This solvent-dependent basicity makes sodium methoxide particularly useful in organic reactions requiring strong, unsolvated bases.^[36]^[37] In protic solvents such as methanol, sodium methoxide undergoes complete dissociation according to the equilibrium CH₃ONa ⇌ Na⁺ + CH₃O⁻, owing to the ionic nature of the compound and the solvating properties of the medium, which fully ionizes the salt without significant ion pairing. Compared to sodium hydroxide, methoxide exhibits superior basicity in non-aqueous environments; for instance, in DMSO, the pKa of water rises to 32, rendering hydroxide a weaker base than methoxide by approximately 3 pKa units (a factor of about 1000 in basic strength). Additionally, methoxide is slightly stronger than alkoxides derived from longer-chain alcohols, such as ethoxide (pKa of ethanol ≈15.9 in water), with a pKa difference of roughly 0.4 units that favors methoxide's proton-accepting ability.^[37]^[38] Beyond basicity, the methoxide anion demonstrates notable nucleophilicity, particularly in bimolecular nucleophilic substitution (SN2) reactions, where its compact size confers high charge density on the oxygen atom, facilitating efficient attack on electrophilic centers. The polarizability of oxygen further aids in stabilizing the transition state during bond formation. In aprotic solvents like DMSO, this nucleophilicity is amplified due to minimal anion solvation, potentially increasing reactivity by orders of magnitude—up to 10⁴ times compared to protic media—by preventing the anion from being "caged" by solvent molecules. This combination of basic and nucleophilic properties underpins sodium methoxide's role as a versatile reagent in synthetic chemistry.^[39]

Reactions with common substances

Sodium methoxide undergoes hydrolysis when exposed to water, reacting according to the equation:

\ce{CH3ONa + H2O -> CH3OH + NaOH}

This reaction is violent and highly exothermic, generating significant heat that can ignite nearby combustibles if moisture is limited; the rate increases with higher water content, making it a key concern for handling in humid environments.^[40] Exposure to carbon dioxide leads to carbonation, where sodium methoxide reacts as follows:

\ce{CH3ONa + CO2 -> CH3OCO2Na}

This produces sodium methyl carbonate, which can further decompose to sodium carbonate and methanol. Atmospheric CO₂ exposure can thus degrade the compound over time, particularly in non-inert conditions.^[41] With acids, sodium methoxide undergoes rapid neutralization, exemplified by its reaction with hydrochloric acid:

\ce{CH3ONa + HCl -> CH3OH + NaCl}

This protonation is quantitative and vigorous, releasing methanol and posing an ignition risk due to the exothermic nature and flammable products.^[42]^[7] As a nucleophile, sodium methoxide reacts with alkyl halides in the Williamson ether synthesis, such as:

\ce{CH3ONa + R-X -> R-OCH3 + NaX}

where R is typically a primary or methyl group and X is a halide; this SN2 pathway efficiently forms methyl ethers, favored for unhindered substrates to minimize elimination side products. Sodium methoxide also reacts with oxygen in air, particularly in the presence of CO₂, leading to decomposition into sodium formate and sodium carbonate.^[43] Sodium methoxide exhibits mild reducing behavior, serving as a hydride source in certain catalytic reductions like alkyne to alkene conversions, but must be handled under inert atmospheres to prevent reaction with air.^[44]

Applications

In organic synthesis

Sodium methoxide serves as a strong base in organic synthesis for deprotonating esters with α-hydrogens, facilitating enolate formation in Claisen condensations to produce β-keto esters.^[45] In a representative example, treatment of diethyl oxalate with acetone using sodium methoxide in methanol yields ethyl acetopyruvate in high yields through this condensation mechanism.^[46] This reaction is particularly useful for constructing carbon-carbon bonds in the synthesis of complex carbonyl compounds. The compound also promotes E2 elimination reactions, acting as a base to abstract β-hydrogens from alkyl halides, leading to alkene formation via dehydrohalogenation.^[47] For instance, 2-bromobutane reacts with sodium methoxide in methanol to afford but-2-ene as the major product, following Zaitsev's rule under these conditions.^[48] This method is commonly employed in laboratory settings to prepare alkenes from secondary or primary alkyl halides. As a nucleophile, sodium methoxide participates in SN2 displacements with primary alkyl halides or tosylates, enabling the synthesis of methyl ethers in the Williamson ether synthesis.^[49] A typical reaction involves the treatment of ethyl bromide with sodium methoxide to produce ethyl methyl ether in good yield.^[50] In small-scale transesterifications, sodium methoxide catalyzes the exchange of alkoxy groups between esters and alcohols, allowing for the preparation of modified esters under mild conditions.^[51] This is valuable for adjusting ester solubility or functionality in synthetic routes. Sodium methoxide is also utilized in the Favorskii rearrangement of α-halo ketones, where it induces ring contraction or rearrangement to carboxylic acid derivatives via semibenzilic intermediates.^[52] For example, 6-tosyloxyisophorone undergoes rearrangement with sodium methoxide in methanol to form a delocalized intermediate leading to rearranged products.^[52] Recent applications (2020–2025) highlight sodium methoxide in green, one-pot syntheses for pharmaceutical intermediates, such as the cyanoamidine cyclization of formamide derivatives to access the nucleobase of Remdesivir, an antiviral drug, using methanolic sodium methoxide at ambient temperature.^[53] Additional examples include its use in the total synthesis of carbazomycins E and F (2024), where sodium methoxide facilitates deprotection in methanol at elevated temperatures, and in enhanced biodiesel catalysis studies (2025) combining sodium methoxide with acetates for improved reaction rates in soybean oil methanolysis.^[54]^[55] This approach minimizes solvent use and steps, aligning with sustainable synthesis principles for analgesics and other therapeutics.^[56]

In industrial processes

Sodium methoxide serves as a key homogeneous catalyst in the industrial production of biodiesel through the transesterification of vegetable oils or animal fats with methanol. The reaction involves triglycerides reacting with methanol to form fatty acid methyl esters (biodiesel) and glycerol as a byproduct, represented by the equation:

\text{Triglyceride} + 3 \text{CH}_3\text{OH} \xrightarrow{\text{NaOMe}} 3 \text{Methyl esters} + \text{Glycerol}

Typically, 0.5–1% sodium methoxide by weight of the oil is used, enabling high yields (often >95%) under mild conditions of 50–65°C and atmospheric pressure.^[57] This process dominates global FAME biodiesel output, which neared 50 billion liters (approximately 44.7 million metric tons) in 2023 and is projected to near 50 million metric tons annually for FAME by 2025, driven by mandates in regions like the EU and Indonesia.^[58]^[59] In polymer manufacturing, sodium methoxide acts as an initiator for the anionic ring-opening polymerization of alkylene oxides, such as ethylene oxide and propylene oxide, to produce polyethers including polypropylene glycol. The mechanism involves nucleophilic attack by the methoxide ion on the epoxide ring, propagating chain growth under controlled conditions to yield polymers with molecular weights up to 50,000 g/mol for polyethylene glycol segments, often in copolymer formulations for enhanced properties. This application supports the production of polyurethane precursors and surfactants on a large scale.^[60] Sodium methoxide is employed in the industrial synthesis of pharmaceutical intermediates, particularly vitamins and antibiotics. In vitamin B1 (thiamine) production, it facilitates condensation steps, such as the reaction of acetamidine with intermediates in continuous-flow processes, enabling efficient scaling for global supply. For antibiotics like sulfadiazine, it serves as a condensing agent in the formation of sulfonamide structures from key precursors.^[61]^[62] Beyond these, sodium methoxide catalyzes the synthesis of biolubricants and greases from vegetable oil-derived biodiesel. It promotes the transesterification of fatty acid methyl esters with polyhydric alcohols like trimethylolpropane at 120–130°C, yielding esters with high viscosity indices (e.g., 140) suitable for ISO VG46 standards and used in eco-friendly formulations. In agrochemicals, it aids post-2020 expansions in herbicide production by acting as a base catalyst in synthesizing active ingredients for crop protection, aligning with rising agricultural demands.^[63]^[64] Market trends indicate steady demand growth for sodium methoxide, with a projected CAGR of 4–6% through 2030, largely fueled by the biodiesel sector's expansion amid renewable fuel policies and sustainability goals. This growth supports a market value of approximately USD 2 billion as of 2024.^[65]^[26]

Stability and storage

Chemical stability

Sodium methoxide exhibits limited thermal stability, beginning to decompose in air above its melting point of 127 °C, with more pronounced thermal decomposition occurring at temperatures exceeding 350 °C. At these higher temperatures, it breaks down into sodium carbonate, sodium hydroxide, amorphous carbon, and a mixture of saturated and unsaturated hydrocarbons as gaseous products.^[1]^[66] This process is influenced by the presence of oxygen or other atmospheric components, potentially leading to the formation of sodium oxides and carbon oxides under combustion conditions.^[9] The compound is highly sensitive to moisture, undergoing gradual hydrolysis in humid air to form sodium hydroxide and methanol over periods of days to weeks, depending on humidity levels. This reaction proceeds slowly compared to direct contact with liquid water, which causes rapid and violent decomposition, but prolonged exposure still compromises the reagent's integrity. Additionally, sodium methoxide reacts with atmospheric carbon dioxide, forming sodium methyl carbonate and eventually sodium carbonate and sodium formate, which can occur over weeks in open air and reduce its catalytic activity significantly, for example in cross-coupling applications.^[67] Commercially, the pure solid form of sodium methoxide has a shelf life of up to 60 months when stored properly under inert conditions. Methanolic solutions remain stable for extended periods if kept sealed and protected from atmospheric ingress. Key factors affecting long-term stability include low impurity levels, particularly water content below 0.1–0.25%, which is essential for ensuring reproducible reaction outcomes; higher moisture leads to premature hydrolysis and variable basicity. In methanolic solutions, the pH remains highly alkaline at approximately 13–14, but this stability diminishes over time as decomposition products accumulate.^[68]^[69]^[70]

Recommended storage conditions

Sodium methoxide requires storage in airtight, dry containers made of inert materials such as glass or high-density polyethylene (HDPE), ideally under a nitrogen blanket to exclude air and moisture.^[9] No metal containers should be used, as they can react with the compound; suitable alternatives include mild steel drums with corrosion-resistant linings.^[9] For solutions, compatible materials like stainless steel or low-density polyethylene (LDPE) are also acceptable, provided they maintain a tight seal.^[71] The compound should be kept at cool temperatures below 25 °C, away from heat sources, direct sunlight, and humidity to preserve stability.^[9] Solutions should be stored above 7 °C to prevent crystallization, and refrigeration is advisable for long-term storage if it does not promote phase separation.^[71] Due to its sensitivity to air and moisture, which can lead to decomposition, storage areas must be well-ventilated to disperse any potential hydrogen gas evolved from minor reactions.^[5] Storage must segregate sodium methoxide from incompatible substances, including acids, water, carbon dioxide sources, oxidizing agents, and metals like aluminum or zinc that could generate hydrogen gas.^[9] Containers should be kept locked and in well-ventilated, dry locations, with desiccants employed in storage environments to absorb residual moisture and extend shelf life.^[72] For transportation, sodium methoxide is classified as a hazardous material; the solid form carries UN number 1431 (Class 4.2, spontaneous combustion, with subsidiary risk 8 for corrosivity), while solutions bear UN number 1289 (Class 3 flammable liquid, with subsidiary risk 8).^[9]^[71] Shipments must comply with DOT regulations for flammables and corrosives, including proper labeling, packaging in approved containers, and segregation from incompatibles during transit.^[71]

Safety and hazards

Health and toxicity

Sodium methoxide is highly corrosive to skin and eyes upon contact, causing severe burns, redness, pain, and potential permanent damage including blindness.^[1] Inhalation of its dust or vapors irritates the respiratory tract, leading to coughing, wheezing, and in severe cases, pulmonary edema with delayed effects.^[5] The LC50 for inhalation in rats exceeds 1.7 mg/L (approximately 1700 mg/m³) over 4 hours, indicating moderate acute toxicity via this route.^[73] Ingestion of sodium methoxide results in severe gastrointestinal damage due to its hydrolysis into sodium hydroxide and methanol, accompanied by symptoms of methanol poisoning such as nausea, vomiting, abdominal pain, and metabolic acidosis.^[1] The oral LD50 in rats is approximately 2.0 g/kg, classifying it as harmful if swallowed.^[74] Chronic exposure to sodium methoxide may lead to liver and kidney damage, as well as optic nerve effects from repeated methanol absorption, with metabolites like formic acid contributing to acidosis and potential vision impairment.^[5] Occupational exposure limits are primarily based on the methanol component, with OSHA setting a PEL of 200 ppm (8-hour TWA) and 250 ppm (STEL), while ACGIH recommends a TLV of 200 ppm (8-hour TWA) and 250 ppm (STEL).^[75] First aid measures include immediate flushing of affected skin or eyes with copious water for at least 15 minutes, removal to fresh air for inhalation exposure, and seeking prompt medical attention; there is no specific antidote, so treatment is symptomatic and supportive.^[76]

Fire and explosion risks

Sodium methoxide in its solid form is not inherently flammable but poses significant fire risks due to its reactivity with moisture and certain substances. The anhydrous powder can self-ignite in the presence of moist air at temperatures above approximately 50 °C, leading to spontaneous combustion. Solutions of sodium methoxide in methanol, commonly used at concentrations around 30 wt%, are highly flammable liquids with a flash point of 16–17 °C, making them susceptible to ignition from sparks, open flames, or hot surfaces.^[77] The autoignition temperature for the material is approximately 240 °C, above which decomposition and ignition can occur rapidly.^[78] Reactivity hazards further exacerbate fire and explosion risks. Sodium methoxide reacts vigorously with water or acids, generating flammable hydrogen gas (H₂) and heat through an exothermic reaction, which can lead to ignition or explosion if confined.^[6] In powder or granular form, it can form explosive dust clouds when dispersed in air, particularly in industrial settings where fine particles are generated during handling or processing.^[7] According to the NFPA 704 hazard rating system, sodium methoxide solutions are rated as Health: 3 (serious hazard), Flammability: 3 (serious fire hazard), and Reactivity: 2 (moderate reactivity), with a special notation for water reactivity due to the potential for violent gas evolution. For firefighting, dry chemical powders or carbon dioxide (CO₂) are recommended extinguishing agents, as they suppress flames without introducing water. Water must be avoided, as it intensifies the reaction, producing additional flammable gases and heat.^[79] Historical incidents include laboratory explosions from accidental addition of solid sodium methoxide to water, resulting in rapid hydrogen release and ignition.^[78] In industrial contexts, such as biodiesel production plants, fires have occurred due to moisture exposure or improper handling, prompting updated safety guidelines in the 2020s emphasizing inert atmospheres and dust control measures.^[80]

Environmental considerations

Sodium methoxide exhibits moderate acute toxicity to aquatic organisms, primarily due to its hydrolysis products rather than direct effects of the compound itself. Short-term toxicity tests indicate LC50 values for fish species such as the bluegill sunfish (Lepomis macrochirus) exceeding 15,000 mg/L over 96 hours, while EC50 values for invertebrates like Daphnia magna range from 10,000 to 22,400 mg/L over 48 hours.^[73]^[81] Algal growth inhibition (EC50 for Selenastrum capricornutum) is reported above 10,000 mg/L over 72 hours. However, upon contact with water, sodium methoxide hydrolyzes to sodium hydroxide and methanol, leading to significant pH elevation in aquatic environments, which can disrupt ecosystems by causing stress to sensitive species such as fish and algae even at lower concentrations.^[82] The biodegradability of sodium methoxide is favorable, with the methoxide ion undergoing rapid aerobic degradation in activated sludge, achieving over 70% removal within 28 days according to OECD 301 guidelines.^[83]^[82] In contrast, the sodium hydroxide byproduct persists indefinitely in the environment as an inorganic salt, potentially contributing to long-term alkalinity changes in soil and water bodies. The compound itself shows low environmental persistence due to its reactivity with moisture, hydrolyzing quickly in soil or water, though the methanol released as a byproduct has low bioaccumulation potential (log Kow = -0.77) and is readily biodegraded by microorganisms.^[84] Under EU REACH regulations, sodium methanolate (CAS 124-41-4) is classified as harmful to aquatic life with long-lasting effects (Aquatic Chronic 3, H412), requiring risk management measures for releases during manufacturing or use. In the United States, the EPA does not specify direct effluent limits for sodium methoxide in wastewater, but discharges are regulated indirectly through pH controls (typically 6-9) under the Clean Water Act and methanol limits (e.g., 5 mg/L in some industrial categories) to prevent environmental harm. The global expansion of biodiesel production, where sodium methoxide serves as a key catalyst, has increased potential releases, though overall environmental exposure remains low due to its contained industrial applications and hydrolysis reactivity.^[85] To mitigate environmental risks, neutralization of effluents with acids such as sulfuric or hydrochloric acid is recommended prior to discharge, reducing pH impacts and facilitating safe disposal. In biodiesel processes, recycling of excess methanol and catalyst recovery techniques, advanced since 2020 through green chemistry initiatives, minimize waste generation and reduce aquatic releases by up to 90% in optimized systems.^[86]^[87] These practices align with sustainability goals, ensuring that the ecological footprint of sodium methoxide use remains manageable despite its role in expanding renewable fuel sectors.

References

[1]
Sodium Methoxide | CH3ONa | CID 10942334 - PubChem
Sodium methylate is a white amorphous powder. It reacts with water to form sodium hydroxide, a corrosive material, and methyl alcohol, a flammable liquid.
[2]
De-O-acetylation using sodium methoxide - NCBI - NIH
Oct 6, 2021 · Instruments · 1. Flask, magnetic stirrer, and stir bar (for reaction) · 2. Rotary evaporator · 3. Ice bath or cooling bath (for synthesis) · 4.Missing: applications | Show results with:applications
[3]
Biodiesel Production Techniques | Oklahoma State University
Sodium hydroxide (NaOH), potassium hydroxide (KOH) and sodium methoxide (CH3ONa) are the most common catalysts for transesterification. Sodium methylate (sodium ...
[4]
Optimization of Sunflower Oil Transesterification Process Using ...
In this study, the methanolysis process of sunflower oil was investigated to get high methyl esters (biodiesel) content using sodium methoxide.<|separator|>
[5]
[PDF] Common Name: SODIUM METHYLATE HAZARD SUMMARY ...
It is used as a catalyst for the treatment of edible fats and oils, and in the production of pharmaceuticals and other chemicals. REASON FOR CITATION. * Sodium ...
[6]
SODIUM METHYLATE - CAMEO Chemicals - NOAA
It is used to process edible fats and oils, and to make other chemicals. Hazards. What is this information?
[7]
ICSC 0771 - SODIUM METHYLATE - Inchem.org
Highly flammable. Many reactions may cause fire or explosion. Risk of fire and explosion on contact with water, moist air or metals. ; NO open flames, NO sparks ...
[8]
alkoxides (A00225) - IUPAC
alkoxides ; ROM , derivatives of alcohols, ; ROH , in which ; R · is saturated at the site of its attachment to oxygen and ; M · is a metal or other cationic species.
[9]
None
### Physical and Chemical Properties of Sodium Methoxide Powder (Sigma-Aldrich 164992)
[10]
Heat capacity measurements on sodium alkoxides - ScienceDirect
The Cp,m 298 of sodium methoxide, sodium ethoxide, sodium n-propoxide and sodium iso-propoxide were measured and found to be 65.05, 90.87, 113.52 and 121.20 J K ...
[11]
Sodium methoxide 25wt. methanol 124-41-4
### Summary of Physical Properties of Sodium Methoxide Solution (25 wt.% in Methanol)
[12]
List of experimental bond lengths for bond type rCO - CCCBDB
Experimental rCO bond lengths include 1.115 Å for CO+ (carbon monoxide cation), 1.128 Å for CO (carbon monoxide), and 1.135 Å for Borane carbonyl.
[13]
Die Kristallstruktur des Natriummethylats - Weiss - 1964
Die Kristallstruktur von NaOCH3 wurde aus Pulverdiagrammen ermittelt. NaOCH3 ist isostrukturell mit LiOCH3 (tetragonale Zelle mit a = 4,34; c = 7,43 Å).
[14]
https://journals.iucr.org/b/issues/2021/01/00/ne5003/
[15]
Crystal structure of [Na(CH 3 OH) 5 ] 2 [Mo 6 (μ 3 -Br) 8 (OCH 3 ) 6 ]
Jun 15, 2003 · The structure is built of two [Na(CH3OH)5]+ cations and the [Mo6(μ3-Br)8(OCH3)6]2− anion. All six-oxygen atoms from coordinated methoxo groups ...
[16]
[PDF] Synthesis and characterization of sodium alkoxides
Analysis of sodium methoxide using X-ray powder diffraction method revealed tetragonal crystal structure and the measured lattice parameters matched very ...
[17]
Sodium methoxide - Optional[1H NMR] - Chemical Shifts
1H Nuclear Magnetic Resonance (NMR) Chemical Shifts. View the Full Spectrum for FREE! The full spectrum can only be viewed using a FREE account.
[18]
USH1697H - Continuous process for sodium methylate
The process involves charging a reaction vessel with a solution of sodium methylate in methanol at a temperature of from about 80° to 86° C.; providing an ...
[19]
Preparation and Standardization of 0.1 M Sodium Methoxide
Sep 25, 2010 · Preparation and standardisation of 0.1 M Sodium Methoxide solution using Benzoic acid and Thymolphthalein solution as indicator that is used for pharmaceutical ...
[20]
NaH + CH3OH = CH3ONa + H2 - Chemical Equation Balancer
Word Equation. Sodium Hydride + Methanol = Sodium Methoxide + Dihydrogen. NaH + CH3OH = CH3ONa + H2 is a Double Displacement (Metathesis) reaction where one ...
[21]
Sodium methoxide - Sciencemadness Wiki
Oct 10, 2019 · Sodium methoxide can be prepared by slowly and carefully adding metallic sodium to an excess of anhydrous methanol. The resulting sodium ...Properties · Preparation · Handling
[22]
Organic Syntheses Procedure
Thermos flask. After the reaction mixture has cooled to about 2°, a solution of 24.3 g. (0.45 mole) of sodium methoxide ...
[23]
Process Simulation and Techno-Economic Analysis of the ...
Dec 9, 2015 · This work evaluates different methods for the manufacture of sodium methoxide, diluted in methanol. Alternative process designs are reviewed.
[24]
US2877274A - Production of sodium methoxide - Google Patents
Sodium methoxide in methanolis drawn off from the bottom of the column and passed through a water-cooled product cooler and collected in a hold tank. This ...
[25]
Process Simulation and Techno-Economic Analysis of the ...
Aug 5, 2025 · This work evaluates different methods for the manufacture of sodium methoxide, diluted in methanol. Alternative process designs are reviewed.
[26]
Sodium Methoxide Market to Reflect Impressive Growth Rate
Volume sales of the global sodium methoxide market were pegged at 497,542.5 tons in 2017, according to a new Fact.MR research analysis. Significant growth of ...
[27]
36 Sodium Methylate Manufacturers in 2025 - Metoree
American Elements was founded in 1997 in California and currently has research and production facilities in Utah, Mexico, China, and the United Kingdom. AE ...
[28]
Sodium Methoxide Market Growth Drivers & Analysis - ReAnIn
Sodium Methoxide Market was valued at USD 1957.55 million in the year 2024. The size of this market is expected to increase to USD 3398.63 million by the ...
[29]
Incorporation of hydrogen by-product from NaOCH 3 production for ...
Mar 1, 2019 · We evaluate the potentiality of incorporating the hydrogen by-product from the NaOCH 3 production for the synthesis of methanol via hydrogenation of CO 2.
[30]
[PDF] Comparison of Different Synthesis Schemes for Production of ...
Nov 30, 2020 · This research investigates the process simulation of sodium methoxide (NaOCH3) synthesis from methanol (CH3OH) and sodium hydroxide (NaOH) under ...
[31]
Dimethyl Sulfate as Methylation Agent and Solvent in Highly ...
Mar 29, 2025 · DMS was used as the esterification reagent (electrophilic reagent) or methylation agent, as well as the aprotic solvent for the reaction. Pure ...
[32]
Electrodialysis in a non-aqueous medium: production of sodium ...
The principle involves the double decomposition of a salt and an alcohol. In effect, an alcohol is split into protons and alkoxide ions, the latter forming the ...
[33]
Electrolytic method to make alkali alcoholates using ceramic ion ...
The first is a sodium-based process in which sodium metal is reacted with methanol to produce sodium methylate. This method uses sodium metal as a raw material, ...
[34]
Sodium Methylate Solution, 25% - Evonik
A solution of sodium methylate (25% in methanol), a strong base commonly used in organic synthesis and as a catalyst in transesterification reactions.
[35]
Bordwell pKa Table
- **pKa of Methanol (CH3OH):**
[36]
pKa Tables | Green Chemistry: Principles and Case Studies - Books
Dec 3, 2019 · Substrate . pKa . H2O . (DMSO) . Inorganic acids. H2O, 15.7, (32). H3O+, −1.7. H2S, 7.00. HBr, −9.00, (0.9). HCl, −8.0, (1.8).<|control11|><|separator|>
[37]
[PDF] pka bases.cdx
pKa values for bases refer to the pKa of their conjugate acids. For example, hydroxide (HO-) has a pKa of 15.7, which is the pKa of H2O.
[38]
What Makes A Good Nucleophile? - Master Organic Chemistry
Jun 18, 2012 · According to the reactivity scale of Ernst Mayr, methoxide is approximately 1000 times more nucleophilic than hydroxide ion, although it does ...
[39]
https://www.masterorganicchemistry.com/2012/06/18/what-makes-a-good-nucleophile/
[40]
[PDF] The Reaction of Alkoxide Ions with Carbon Dioxide
The recovery of barium carbonate precipitated from aqueous methanol by known amounts of sodium carbonate was found to be 99.5%. No alkyl- carbonate was ...
[41]
https://ojs.library.okstate.edu/osu/index.php/OAS/article/view/5958/5580
[42]
Methoxide - an overview | ScienceDirect Topics
Sodium methoxide being a strong base ionizes all hydroxyl groups on the flavonoid nucleus. However on the UV spectra of flavones and flavonols, it is used for ...
[43]
The Use of Sodium Methoxide in the Claisen Reaction
The Journal of Organic Chemistry, The Journal of Physical Chemistry, The ... The Use of Sodium Methoxide in the Claisen Reaction. Click to copy article ...Missing: condensation | Show results with:condensation
[44]
ethyl acetopyruvate - Organic Syntheses Procedure
It is reported that the condensation of ethyl oxalate and acetone by means of sodium methoxide furnishes methyl acetopyruvate in excellent yields and that the ...
[45]
Bulky Bases in Elimination Reactions - Master Organic Chemistry
Oct 24, 2012 · “Bulky Bases” Tend To Give A Higher Proportion Of “Non-Zaitsev” Products. For instance, instead of using sodium methoxide, (NaOCH3) if you use ...Missing: dehydrohalogenation | Show results with:dehydrohalogenation
[46]
Elimination by the E2 mechanism - Chemistry LibreTexts
Jan 22, 2023 · In the methanol solvent used here, methanethiolate has greater nucleophilicity than methoxide by a factor of 100. Methoxide, on the other hand ...Missing: dehydrohalogenation | Show results with:dehydrohalogenation
[47]
18.2: Preparing Ethers - Chemistry LibreTexts
Sep 30, 2024 · Styrene reacts with mercuric trifluoroacetate and methanol, then sodium borohydride forming 1-methoxy-. The mechanism of the alkoxymercuration ...
[48]
The Williamson Ether Synthesis - Master Organic Chemistry
Oct 24, 2014 · Primary and Methyl Alkyl Halides Work Best. The Williamson works best for primary and methyl alkyl halides. ... ethanol when using sodium ethoxide ...
[49]
Transesterification - Master Organic Chemistry
Nov 10, 2022 · Transesterification under basic conditions can be achieved through adding an alkoxide to an ester. In this example, adding sodium ethoxide (NaOCH 2 CH 3 ) to ...
[50]
Evidence for a Delocalized Intermediate in the Favorskii ...
Evidence for a Delocalized Intermediate in the Favorskii Rearrangement. The Reaction of 6-Tosyloxyisophorone with Sodium Methoxide in Methanol.
[51]
Cyanoamidine Cyclization Approach to Remdesivir's Nucleobase
Conditions: formamide 12 (1.0 equiv), cyanamide (1.0–2.0 equiv), sodium methoxide (0.5–1.0 equiv), and methanol (0.5 M) stirred at 23 °C for 1 h in a sealed ...
[52]
Dihydronaphthofurans: synthetic strategies and applications
Feb 5, 2020 · Sodium methoxide and potassium iodide promoted condensation of 2 ... A simple and highly efficient one-pot protocol for the synthesis ...
[53]
Transesterification and esterification for biodiesel production
Sodium-based catalysts, including sodium ethoxide (C2H5ONa) and sodium methoxide (CH3ONa), offer higher catalytic efficiency, with 100% conversion reported for ...
[54]
None
### Summary of Global FAME Biodiesel Production (2023 and Projections for 2025)
[55]
BSFL biodiesel production and cost reduction: A review
Jun 15, 2025 · Global biodiesel consumption in 2021 is about 41.27 million tons, and consumption is expected to grow to 56.19 million tons in 2027, with a ...Bsfl Biodiesel Production... · 1. Introduction · 4. Industry<|separator|>
[56]
Polymerization of Ethylene Oxide, Propylene Oxide, and Other ...
Dec 29, 2015 · The review summarizes current trends and developments in the polymerization of alkylene oxides in the last two decades since 1995.
[57]
[PDF] An Eight-Step Continuous-Flow Total Synthesis of Vitamin B1
prepared from acetamidine hydrochloride and sodium methoxide were streamed to the flow reactor at 75 °C with a residence time of 5–7 min (Table 2, entries 1 ...
[58]
Sodium Methoxide_Tiande Chemical
It is used as basic condensing agent and catalyst in organic synthesis, as raw material of vitamin B1, a and sulfadiazine.
[59]
Manufacturing of environment friendly biolubricants from vegetable ...
The second stage is the reaction of biodiesel with trimethylolpropane using sodium methoxide as catalyst to yield palm or Jatropha oil base trimethylolpropane ...
[60]
Sodium Methoxide Market Analysis, By Demand, By Region, By ...
Apr 19, 2024 · In 2023, the Sodium Methoxide market value was around USD 207.47 million. By 2032, it's projected to reach around USD 325.88 million, ...
[61]
Sodium Methoxide Market | Global Market Analysis Report - 2035
Sodium Methoxide Market was worth USD 560.0 million in 2025, and is predicted to grow to USD 830.0 million by 2035, with a CAGR of 4.0%.
[62]
http://www.tdchem.com/en/index.php?m=home&c=View&a=index&aid=484
[63]
Kinetics of thermal decomposition of sodium methoxide and ethoxide
Nov 30, 2006 · The reaction of sodium metal with alcohol to yield respective sodium alkoxide was performed under argon atmosphere. Results and discussion.Missing: inert | Show results with:inert
[64]
[PDF] aks760 - sodium methoxide, 95% - Gelest, Inc.
Jun 2, 2015 · Stable under nitrogen or argon in sealed containers. Material decomposes slowly in contact with moist air and rapidly in contact with water. ...
[65]
Sodium Methoxide Powder pure, 98% - Krins Life Sciences
In stockStorage · Room Temperature ; Shelf Life · 60 Months ; Appearance (Colour), White ; Appearance (Form), Crystalline powder ; Solubility (Turbidity) 10% aq. solution ...
[66]
[PDF] SODIUM METHOXIDE POWDER
SODIUM METHOXIDE POWDER. 06/25/2023. PRODUCT SPECIFICATION. Page 1 | 1. Data ... Moisture Content (by KF). 0.25 %w/w. Purity. 99.5% - 99%. Free Alkalinity as ...Missing: reproducibility | Show results with:reproducibility
[67]
124-41-4 CAS | SODIUM METHOXIDE | Laboratory Chemicals
Physical Properties ; pH value, 13 ; Flash point [°C], 33 °C ; Vapour density, 1.87 ; Solubility in water [% weight], Decomposed by water ; Explosion limits -lower ...
[68]
[PDF] Safety Data Sheet - BASF
Oct 28, 2025 · Information on: Sodium Hydroxide. Symptoms: Overexposure may cause:, vomiting, circulatory collapse, death, stenosis, dyspnea, salivation, ...<|control11|><|separator|>
[69]
[PDF] SAFETY DATA SHEET - Fisher Scientific
Jun 25, 2009 · Use only under a chemical fume hood. Do not breathe mist/vapors/spray. Do not ingest. If swallowed then seek immediate medical assistance. Do ...
[70]
[PDF] Sodium Methoxide - Safety Data Sheet - ChemicalBook
Sep 27, 2025 · H303 May be harmfulif swallowed. H311 Toxic in contact with skin. H314 Causes severe skin burns and eye damage. H315 Causes skin irritation.
[71]
SAFETY DATA SHEET - TCI Chemicals
Mar 28, 2025 · Sodium Methoxide: Acute oral toxicity. : LD50 (Rat): 2,037 mg/kg. Assessment: The component/mixture is minimally toxic after single.
[72]
[PDF] SAFETY DATA SHEET - Fisher Scientific
May 29, 2013 · Precautionary Statements. Prevention. Wash face, hands and any exposed skin thoroughly after handling. Do not eat, drink or smoke when using ...
[73]
https://www.chemicalbook.com/msds/sodium-methoxide.pdf
[74]
Sodium methoxide, ca 30% w/w in methanol 500 mL - Fisher Scientific
In stock $79 deliverySodium methoxide, ca 30% w/w in methanol. Catalog No. AAB21872AP. 500 mL. SDS ... Flash Point, 16°C (61°F). Odor, Alcohol-like. Linear Formula, NaOCH3. Quantity ...
[75]
Sodium Methoxide | CH3ONa | CID 10942334 - PubChem
7 Autoignition Temperature. 240 °C. European Chemicals Bureau; IUCLID Dataset, Sodium methanolate (124-41-4) (2000 CD-ROM edition). Available from, as of ...
[76]
[PDF] Sodium Methoxide Powder MSDS - Green Catalysts
Sodium methoxide is toxic, highly flammable, reacts violently with water, and is toxic by inhalation, skin contact, and if swallowed. It causes burns.
[77]
Fire and explosion hazards related to the industrial use of potassium ...
The commercial importance of sodium methoxide (CH3ONa) and potassium methoxide (CH3OK) has increased with the booming development of biodiesel production [1].
[78]
https://pubchem.ncbi.nlm.nih.gov/compound/10942334
[79]
https://greencatalysts.com/wp-content/uploads/2020/11/SOMETH-msds.pdf
[80]
[PDF] Safety Data Sheet - BASF
Jan 7, 2025 · Thermal decomposition: > 280 °C (DTA). Thermal decomposition above the indicated temperature is possible. The indicated value is for inert gas ...
[81]
[PDF] Sodium methoxide solution - Santa Cruz Biotechnology
Reacts with water or moist air to produce methanol. 67-56-1 sodium hydroxide ... reaction in air is estimated to be 17 days, calculated from its rate ...
[82]
Improving biodiesel yields from waste cooking oil by using sodium ...
▻ Sodium methoxide would be used as catalysts to increases reaction rate of biodiesel. Introduction. The development of biodiesel is being driven by the ...
[83]
Methoxide Catalysts in Biodiesel Production - Farm Energy
Apr 12, 2019 · Commercial producers prefer to get their methoxide from solutions of sodium (or potassium) methoxide already dissolved in methanol. Sodium ...
[84]
Sodium Methoxide/Zeolite-Supported Catalyst for Transesterification ...
Apr 12, 2023 · FT–IR analysis conducted on NaOMe revealed the presence of asymmetric and symmetric C-H stretching vibrations at 2832 cm−1 and 2773 cm−1, ...