Hubbry Logo
Methacrylic acidMethacrylic acidMain
Open search
Methacrylic acid
Community hub
Methacrylic acid
logo
8 pages, 0 posts
0 subscribers
Be the first to start a discussion here.
Be the first to start a discussion here.
Methacrylic acid
Methacrylic acid
Methacrylic acid
View on Wikipedia
from Wikipedia
Methacrylic acid
Structural formula of methacrylic acid
Ball-and-stick model of the methacrylic acid molecule
Names
IUPAC name
Methacrylic acid[1]
Preferred IUPAC name
2-Methylprop-2-enoic acid
Other names
Methacrylic acid
2-Methyl-2-propenoic acid
α-Methacrylic acid
2-Methylacrylic acid
2-Methylpropenoic acid
Identifiers
3D model (JSmol)
Abbreviations MAA
ChEBI
ChemSpider
ECHA InfoCard 100.001.096 Edit this at Wikidata
EC Number
  • 201-204-4
MeSH C008384
UNII
  • InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
    Key: CERQOIWHTDAKMF-UHFFFAOYSA-N
  • CC(C(O)=O)=C
Properties
C4H6O2
Molar mass 86.09 g/mol
Appearance Colorless liquid
Odor Acrid, repulsive[2]
Density 1.015 g/cm3
Melting point 14 to 15 °C (57 to 59 °F; 287 to 288 K)
Boiling point 161 °C (322 °F; 434 K)
9% (25 °C)[2]
Vapor pressure 0.7 mmHg (20 °C)[2]
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H312, H314
P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
3
2
2
Flash point 77.2 °C (171.0 °F; 350.3 K)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 20 ppm (70 mg/m3) [skin][2]
IDLH (Immediate danger)
 N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Methacrylic acid, abbreviated MAA, is an organic compound with the formula CH2=C(CH3)CO2H. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA).

Production

[edit]

In the most common route, methacrylic acid is prepared from acetone cyanohydrin, which is converted to methacrylamide sulfate using sulfuric acid. This derivative in turn is hydrolyzed to methacrylic acid, or esterified to methyl methacrylate in one step. Another route to methacrylic acid starts with isobutylene, which obtainable by dehydration of tert-butanol. Isobutylene is oxidized sequentially to methacrolein and then methacrylic acid. Methacrolein for this purpose can also be obtained from formaldehyde and ethylene. Yet a third route involves the dehydrogenation of Isobutyric acid.[3]

Various green routes have been explored but they have not been commercialized. Specifically, the decarboxylation of itaconic acid, citraconic acid, and mesaconic acids affords methacrylic acid.[4] Salts of methacrylic acid have been obtained by boiling citra- or meso-brompyrotartaric acids with alkalis.[citation needed]

Pyrolysis of ethyl methacrylate efficiently gives methacrylic acid.[5]

Uses and occurrence

[edit]

The main use of methacrylic acid is its polymerization to poly(methyl methacrylate).[6]

It is used in some nail primers to help acrylic nails adhere to the nail plate.[7]

Copolymers consisting partially of methacrylic acid are used in certain types of tablet coatings in order to slow the tablet's dissolution in the digestive tract, and thus extend or delay the release of the active ingredient.[8]

Monocarboxylic unsaturated acids such as methacrylic acid and acrylic acid are used in the production of vinyl ester resins.[9]

MAA esters occur naturally in the oil of Roman chamomile.[10]

Typical vinyl ester resin derived from bisphenol A diglycidyl ether and methacrylic acid.[11]

Reactions

[edit]

For commercial applications, MAA is polymerized using azobisisobutyronitrile as a thermally activated free-radical catalyst. Otherwise, MAA is relatively slow to polymerize thermally or photochemically.[6]

Methacrylic acid undergoes several reactions characteristic of α,β-unsaturated acids (see acrylic acid). These reactions include the Diels–Alder reaction and Michael additions. Esterifications are brought about by acid-catalyzed condensations with alcohols, alkylations with certain alkenes, and transesterifications. Epoxide ring-opening gives hydroxyalkyl esters.[3] Sodium amalgam reduces it to isobutyric acid. A polymeric form of methacrylic acid was described in 1880.[12]

See also

[edit]

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Methacrylic acid

View on Grokipedia
from Grokipedia
Methacrylic acid, with the C₄H₆O₂ and IUPAC name 2-methylprop-2-enoic acid, is an α,β-unsaturated monocarboxylic acid that serves as a fundamental building block in . This colorless, viscous liquid exhibits a pungent, acrid and is moderately soluble in water (approximately 89 g/L at 20°C) while being miscible with most organic solvents such as and . Its physical properties include a of 16°C, a of 163°C, and a of 77°C, rendering it combustible and prone to under certain conditions. Industrially, methacrylic acid is primarily produced via the acetone cyanohydrin (ACH) process, involving the reaction of acetone and hydrogen cyanide to form acetone cyanohydrin, which is then converted to methacrylamide sulfate and hydrolyzed to methacrylic acid. An important alternative is the two-step vapor-phase catalytic oxidation process starting from isobutene (isobutylene): the first step converts isobutene to methacrolein using molybdenum-based catalysts, followed by further oxidation to methacrylic acid with heteropolyacid catalysts. Other routes include the hydrolysis of methacrylamide sulfate or emerging biotechnological methods from renewable feedstocks like sugars, though these are not yet dominant commercially. As a versatile , methacrylic acid is widely used in the manufacture of esters like , which polymerizes into poly(methyl methacrylate) (PMMA), a transparent known as acrylic glass and applied in , , and devices. It also features in adhesives, coatings, textiles, and as a cross-linking co-monomer in resins, with global production around 450,000 tonnes annually as of 2023. Safety concerns are significant due to its corrosiveness; it irritates and damages , eyes, and respiratory tissues upon contact or , with an acute LC₅₀ of 1980 ppm (4 hours) in rats and recommended exposure limits such as AEGL-1 at 6.7 ppm. Proper stabilization with inhibitors like is essential to prevent explosive , and it is handled in industrial settings with stringent ventilation and protective measures.

Properties

Physical properties

Methacrylic acid has the molecular formula C₄H₆O₂ and the CH₂=C(CH₃)CO₂H. It is classified as an α,β-unsaturated , characterized by a carbon-carbon conjugated with the carboxyl group and a methyl at the alpha position. Methacrylic acid appears as a clear, colorless or a low-melting solid, exhibiting an acrid, pungent . Key physical properties of methacrylic acid are summarized in the following table:
PropertyValueConditions
Density1.015 g/cm³20°C
Melting point14–16°C-
Boiling point163°C760 mmHg
Flash point77°CClosed cup
Vapor pressure0.65 mmHg20°C
Refractive index1.43120°C (n_D)
These values reflect the compound's behavior as a moderately volatile with low thermal stability at elevated temperatures. Methacrylic acid exhibits limited in , approximately 9 g/100 mL at 25°C, but is miscible with most organic solvents, including and . Under normal storage conditions, methacrylic acid remains stable when inhibited with agents such as or MEHQ to prevent exothermic triggered by light, heat, oxygen, or contaminants.

Chemical properties

Methacrylic acid has the empirical and molecular formula C₄H₆O₂ and a of 86.09 g/mol. As an α,β-unsaturated monocarboxylic acid, it features a conjugated with the carboxyl group, which enhances electron delocalization and increases reactivity toward and Michael-type reactions compared to saturated carboxylic acids. Methacrylic acid behaves as a weak with a pKₐ of 4.66 at 25 °C, corresponding to a Kₐ of approximately 2.19 × 10⁻⁵. This pKₐ value is higher than that of (pKₐ 4.25), rendering methacrylic acid a slightly weaker due to the electron-donating effect of the α-methyl , which stabilizes the neutral form relative to the conjugate base. Spectroscopic characterization confirms its structural features. In infrared (IR) spectroscopy, characteristic absorptions include the C=O stretch of the carboxyl group at 1710 cm⁻¹ and the C=C stretch of the at 1630 cm⁻¹. (¹H NMR) in CDCl₃ shows the carboxylic proton at 12.2 ppm, vinyl protons at 6.26 and 5.69 ppm (each 1H, dd), and the vinylic methyl at 1.95 ppm (3H, s). The conjugation between the vinyl and carboxyl groups leads to (UV) absorption with a maximum around 207 nm (ε ≈ 10,000 M⁻¹ cm⁻¹ in water), reflecting π-π* transitions. Due to the activated , methacrylic acid exhibits a strong tendency for free-radical self-, particularly at elevated temperatures above 50 °C or under exposure to light and , which can lead to exothermic runaway reactions. Commercial samples are stabilized against premature polymerization by adding inhibitors such as monomethyl ether (MEHQ) at 250 ppm or , which scavenge radicals to prevent .

Production

Industrial synthesis

The primary industrial synthesis of methacrylic acid involves a two-step catalytic oxidation process starting from isobutylene or isobutane, using air or oxygen as the oxidant. In the first step, isobutylene is selectively oxidized to methacrolein over molybdenum-based catalysts, such as Mo-Bi-Fe-Co oxides, at temperatures of 300–400°C and atmospheric pressure. The second step oxidizes methacrolein to methacrylic acid using similar heteropolyacid catalysts, like P-Mo-V-Cs salts, under comparable conditions, achieving overall yields of approximately 70–80% based on isobutylene conversion. An alternative route, known as the acetone cyanohydrin (ACH) process, was historically dominant from the 1930s until the 1960s and remains in use today. This method begins with the reaction of and to form , which is then hydrolyzed in to produce methacrylamide sulfate, followed by to methacrylic acid. The process generates significant containing as a byproduct, requiring treatment, and consumes large quantities of . Global production capacity for methacrylic acid is estimated at around 550,000 metric tons per year as of 2024, with projections for modest growth to approximately 570,000 tons in 2025, driven by demand in polymer sectors. Major producers include Mitsubishi Gas Chemical, , , and Dow Chemical, with a shift toward oxidation routes in recent decades for improved efficiency and reduced reliance on hazardous feedstocks. In oxidation processes, catalysts require periodic regeneration through to maintain activity, while the ACH route's environmental challenges have prompted investments in waste minimization technologies.

Laboratory methods

Methacrylic acid can be prepared in the laboratory through the of methacrylamide or using acid or base catalysts. For base-catalyzed of , the ester is treated with dilute alcoholic solution, followed by acidification to yield the acid, which is then purified by . A more efficient gas-phase method involves passing vapor over Y catalyst at 160–300 °C, achieving up to 80% yield of methacrylic acid due to the rapid reaction rate enabled by the catalyst's acidic sites; the product is collected and isolated via condensation and under reduced pressure. of methacrylamide typically employs or water under heating, producing methacrylic acid and , with purification by extraction into an organic solvent and subsequent of the upper layer to obtain pure acid. A bio-based laboratory route involves the of using solid transition-metal catalysts such as Pd, Pt, or Ru supported on carbon or carriers. The reaction is conducted in at 200–250 °C without external pressure, offering milder conditions than traditional thermal and aligning with principles by utilizing renewable feedstocks; selectivities up to 84% are reported, with the methacrylic acid isolated in 50% yield after of the catalyst and extraction or . Pyrolysis of provides another straightforward laboratory method, analogous to the preparation of from its . The (200 g) is pyrolyzed in a vertical tube packed with glass beads, heated to 590 °C in an electric furnace, with the liquid fed at 90 drops per minute over 2 hours; the effluent is collected in an ice-cooled receiver with a condenser and traps, yielding 70% methacrylic acid after at reduced pressure (69–71 °C/50 mm Hg) and stabilization with . The apparatus requires careful to minimize side products, and the product is stored refrigerated to prevent . Small-scale oxidation of methacrolein to methacrylic acid can be achieved using silica-supported heteropolyacid catalysts, such as CsH₃PMo₁₁VO₄₀ on SBA-15. The catalyst is prepared by impregnating the support with the acid and cesium salt solutions, followed by drying and at 360 °C; the reaction occurs in a fixed-bed reactor at 310 °C and with a feed of 4.4 vol% methacrolein, 11.1 vol% O₂, 17.8 vol% H₂O, and N₂ balance at ~2 s contact time, yielding up to 44% selectivity to methacrylic acid analyzed by . Safety precautions include handling corrosive and toxic compounds in a with protective equipment, as the reaction involves flammable gases and potential over-oxidation to CO₂.

Uses

Polymer applications

Methacrylic acid undergoes free to form poly(methacrylic acid) (PMAA), typically initiated by azo compounds such as (AIBN) or peroxides like (APS) in aqueous or organic media. This process yields polymers with groups that confer pH-responsive properties, enabling applications in specialized materials. PMAA is employed in ion-exchange resins for and heavy metal removal due to its ability to bind cations effectively. Methyl methacrylate, derived from esterification of methacrylic acid, undergoes polymerization to produce poly(methyl methacrylate) (PMMA), known commercially as Plexiglas, which exhibits high transparency (over 92% light transmission), a glass transition temperature of approximately 105°C, and superior weather resistance, making it ideal for optical lenses, signage, and protective glazing. Copolymers of methacrylic acid with methyl methacrylate provide enhanced properties for specific applications. In medical devices, PMMA is used for intraocular lenses, bone cements, and dental prosthetics owing to its biocompatibility and durability. PMAA-based hydrogels, leveraging their swelling in response to pH changes, are utilized in controlled drug delivery systems, such as oral formulations that release therapeutics in the intestinal environment. These materials also find use in dental applications, including bioactive composites for fillings and scaffolds. Copolymers incorporating methacrylic acid segments improve adhesion and flexibility in acrylic paints, sealants, and corrosion-resistant coatings for metals and .

Other industrial uses

Methacrylic acid undergoes esterification to produce various methacrylic esters, such as , which serve as key intermediates in the of coatings, adhesives, and lubricants. These esters enhance , , and resistance to environmental factors in protective coatings for industrial surfaces and , while in adhesives, they provide strong for structural applications in automotive and sectors. In lubricants, longer-chain esters like lauryl methacrylate act as viscosity modifiers and anti-wear additives, improving performance in high-temperature oils. In the production of vinyl ester resins, methacrylic acid reacts with epoxy resins to form thermosetting polymers valued for their superior resistance and mechanical strength. These resins are widely employed in for fabricating chemical-resistant , tanks, and structural composites that withstand harsh industrial environments. In marine applications, they are used to manufacture hulls, decks, and underwater components, providing effective barriers against and osmotic damage. As a , methacrylic acid is incorporated into specialty chemicals for , where it contributes to the synthesis of polymers that act as scale inhibitors and dispersants in cooling systems and processes. In finishes, it improves fabric durability and water repellency through formulations applied during and coating. For processing, methacrylic acid-based emulsions enhance flexibility, smoothness, and resistance to cracking in finished products like and . Direct applications of methacrylic acid include its use in nail primers, where concentrations of 50-88% promote adhesion of acrylic enhancements to the natural nail plate, though it requires careful handling due to its corrosive nature. In pharmaceuticals, methacrylic acid copolymers form enteric coatings for tablets, enabling controlled release in the by dissolving only at higher levels, thus protecting acid-sensitive drugs. Additionally, it serves as a component in ionomers, such as poly(ethylene-co-methacrylic acid) variants, which are utilized in protective coatings and blends for enhanced toughness and self-healing properties in packaging and industrial films. The adhesives and coatings segment alone accounts for about 45% of methacrylate-related demand as of 2024. The market for bio-based methacrylic acid derivatives is experiencing significant growth, projected at a (CAGR) of 17.2% from 2025 to 2033, driven by demands in coatings and applications.

Natural occurrence

Methacrylic acid occurs naturally in trace amounts in the derived from the flowers of Roman chamomile (Anthemis nobilis). This compound contributes to the oil's complex chemical profile, which includes various and terpenoids. Its presence in natural samples, including chamomile , has been analytically confirmed using gas chromatography-mass spectrometry (GC-MS), where fragmentation patterns reveal the methacrylic acid moiety in ester components. Such detection methods highlight its minor role in the volatile fraction of plant-derived oils. While not a major natural product and predominantly obtained through industrial synthesis, methacrylic acid's occurrence in plants has spurred research into green extraction techniques to harness these trace sources sustainably. Recent 2020s studies have also investigated its potential as a microbial metabolite, including biosynthetic pathways in fungi like Aspergillus terreus, which naturally produces the precursor itaconic acid convertible to methacrylic acid. These efforts underscore opportunities for bio-based production from fungal metabolites, though natural yields remain low compared to synthetic routes.

Reactions

Polymerization

Methacrylic acid undergoes free radical chain-growth polymerization primarily through its α,β-unsaturated vinyl group, a process first described in its polymeric form in 1880 by Engelhorn and Fittig. The mechanism consists of three main stages: initiation, propagation, and termination. In the initiation step, an initiator such as 2,2'-azobisisobutyronitrile (AIBN) or benzoyl peroxide decomposes thermally to generate primary radicals, which then add to the double bond of the methacrylic acid monomer to form a propagating radical. Propagation involves the successive addition of monomer units to the growing radical chain, with each step characterized by the propagation rate coefficient kpk_p. Termination occurs via combination or disproportionation of two propagating radicals, with rate coefficients ktck_{tc} and ktdk_{td}, respectively. The homopolymerization of methacrylic acid can be represented by the following equation: n\ceCH2=C(CH3)CO2H→\ce[−CH2−CH(CH3)CO2H−]nn \ce{CH2=C(CH3)CO2H} \rightarrow \ce{[-CH2-CH(CH3)CO2H-]_n} This reaction proceeds under various conditions, including bulk polymerization for high-molecular-weight products, solution polymerization in organic solvents like dimethylformamide to control viscosity, or emulsion polymerization in aqueous media for latex production. Common initiators include peroxides like benzoyl peroxide for thermal initiation and azo compounds like AIBN for precise control at moderate temperatures around 60–80°C. To prevent unwanted premature polymerization during storage or transport, inhibitors such as hydroquinone or monomethyl ether hydroquinone (MEHQ) are added at low concentrations (typically 100–250 ppm), scavenging radicals to stabilize the monomer. In copolymerization, methacrylic acid exhibits specific reactivity ratios that influence the sequence distribution in the . For instance, with styrene in at 65°C, the reactivity ratios are r\ceMAA=0.37r_{\ce{MAA}} = 0.37 and r\cestyrene=0.15r_{\ce{styrene}} = 0.15, indicating a tendency toward alternating copolymers due to the lower reactivity of the methacrylic acid radical toward itself. Similarly, copolymerization with acrylates like yields r\ceMAA≈2.36r_{\ce{MAA}} \approx 2.36 and r\ceEA≈0.41r_{\ce{EA}} \approx 0.41, favoring incorporation of methacrylic acid units early in the . The of the resulting —whether isotactic, syndiotactic, or atactic—significantly impacts properties; isotactic forms exhibit lower in unless the carboxylic groups are ionized (>20% ionization required), leading to ordered structures like worm-like aggregates in films, whereas atactic polymers are readily soluble and form unstructured layers. The kinetics of methacrylic acid follow the classical free radical mechanism, with the overall rate given by Rp=kp(fkd/kt)1/2[\ceI]1/2[\ceM]R_p = k_p (f k_d / k_t)^{1/2} [\ce{I}]^{1/2} [\ce{M}], where ff is the initiator efficiency, kdk_d the decomposition rate coefficient, ktk_t the termination rate coefficient, [\ceI][\ce{I}] the initiator concentration, and [\ceM][\ce{M}] the concentration. , particularly to or added agents like , controls molecular weight by limiting chain length, with the chain transfer constant CS=ktr/kpC_S = k_{tr}/k_p quantifying the efficiency; for in , CSC_S values enable precise tuning of .

Other reactions

Methacrylic acid undergoes esterification with alcohols in the presence of strong acid catalysts, such as or , to yield the corresponding methacrylic esters. A representative example is the reaction with to produce (MMA), a key industrial : \ceCH2=C(CH3)CO2H+CH3OH⇌CH2=C(CH3)CO2CH3+H2O\ce{CH2=C(CH3)CO2H + CH3OH ⇌ CH2=C(CH3)CO2CH3 + H2O} This equilibrium-limited process is typically driven forward by continuous removal of water, often via a Dean-Stark apparatus with using an entrainer like . As an α,β-unsaturated , methacrylic acid participates in Michael addition reactions, where nucleophiles add to the β-carbon position, yielding β-substituted propanoic acid derivatives. Amines, for instance, undergo aza-Michael addition to form β-amino acids, with the electron-withdrawing carboxyl group activating the . Methacrylic acid also functions as an electron-deficient dienophile in Diels-Alder cycloadditions with dienes such as , producing bicyclic adducts like the endo- and exo-isomers of 3-methylbicyclo[2.2.1]hept-5-ene-2-. The reaction proceeds under thermal conditions, with the carboxyl group enhancing reactivity. Selective reduction of the C=C converts methacrylic acid to , typically via catalytic using Pd/C or Pt catalysts under mild pressure and temperature, avoiding reduction of the carboxylic group. The reaction is exothermic, with a reported heat of of approximately -28.5 kcal/mol. LiAlH4 reduces the carboxylic group to the corresponding allylic alcohol, 2-methylprop-2-en-1-ol, leaving the double bond intact. occurs via across the double bond, forming vicinal dihalo acids. addition, for example, yields 2,3-dibromo-2-methylpropanoic acid in a Markovnikov fashion, with the reaction proceeding in inert solvents like . behaves analogously, producing the dichloro derivative.

Safety and environmental aspects

Health and handling hazards

Methacrylic acid is a corrosive substance that can cause severe burns and irritation upon contact with , eyes, and the . It acts as a strong irritant and potential skin sensitizer, leading to redness, , and possible allergic reactions with repeated exposure. Acute oral toxicity in rats shows an LD50 value of approximately 1.2 g/kg, indicating moderate if ingested. Occupational exposure limits are established to minimize health risks. The National Institute for Occupational Safety and Health (NIOSH) recommends a (REL) of 20 ppm (70 mg/m³) as a time-weighted average () for up to 10 hours, with a notation due to potential dermal absorption. The American Conference of Governmental Industrial Hygienists (ACGIH) sets a (TLV) of 20 ppm , also noting absorption concerns. The (OSHA) does not have a specific (PEL) for methacrylic acid but defers to general industry standards for similar irritants. Safe handling requires strict adherence to (PPE) protocols, including chemical-resistant gloves, safety goggles, and protective clothing to prevent skin and eye contact. Storage should occur in cool, well-ventilated areas below 15°C (59°F), with the material stabilized by inhibitors to prevent unintended , which poses an risk during handling. For spills, use inert absorbents such as sand or to contain and neutralize the acid before disposal, avoiding water-reactive responses. Chronic exposure may lead to persistent irritation of the and sensitization. Regarding , studies in rats and mice indicate no significant developmental or reproductive effects at exposure levels up to 300 ppm via . In case of exposure, immediate is critical: flush eyes or with large amounts of for at least 15-30 minutes, remove contaminated clothing, and seek medical attention; for , move to and provide respiratory support if needed; if ingested, do not induce vomiting and rinse the mouth with .

Environmental impact

Methacrylic acid exhibits moderate biodegradability under aerobic conditions, achieving approximately 86% degradation within 28 days according to 301 tests, such as the closed bottle method ( 301D), indicating it is readily biodegradable in standard screening assays. However, its persistence in aquatic environments can vary, with potential for incomplete breakdown in low-oxygen or anaerobic waters, contributing to temporary accumulation if released untreated. Ecotoxicological data reveal moderate toxicity to aquatic organisms, with a 96-hour LC50 of 85 mg/L for rainbow trout (Oncorhynchus mykiss) in flow-through tests under OECD 203 guidelines, classifying it as harmful to aquatic life. Bioaccumulation potential is low, supported by an octanol-water partition coefficient (log Kow) of 0.93 and a bioconcentration factor (BCF) of 2.27, indicating minimal uptake and retention in organisms. Under REACH regulations, methacrylic acid is classified as Aquatic Acute 3 (H402: harmful to aquatic life) and is subject to registration requirements for environmental risk assessment, with restrictions on releases during manufacturing and use. In the , it is listed on the TSCA inventory, and wastewater discharges are regulated under the Clean Water Act's effluent limitations for organic chemicals. Production via conventional oxidation of isobutylene or acetone-cyanohydrin processes generates emissions including volatile organic compounds (VOCs) such as unreacted hydrocarbons and nitrogen oxides (NOx) from catalytic steps, contributing to air pollution and photochemical smog formation. Recent developments as of 2025, including bio-based routes using renewable feedstocks like sugars or plant oils, aim to reduce the carbon footprint by up to 40% compared to fossil-based methods, driven by sustainability initiatives from producers like Arkema. Remediation of methacrylic acid in primarily relies on biological treatment through processes, which achieve 82-97% removal efficiency by leveraging its biodegradability in aerobic systems. For recalcitrant residues, (AOPs) such as UV/H2O2 or enhance degradation by generating hydroxyl radicals, effectively mineralizing the compound to CO2 and in stages.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/Methacrylic-Acid
  2. https://www.marketreportsworld.com/market-reports/methacrylic-acid-market-14715895
  3. https://www.sciencedirect.com/topics/chemistry/methacrylic-acid
  4. https://pmc.ncbi.nlm.nih.gov/articles/PMC7100375/
  5. https://www.chemanalyst.com/industry-report/meth-acrylic-acid-market-1839
  6. https://www.epa.gov/sites/default/files/2014-08/documents/methacrylic_acid_interim_de_oct_2008_c.pdf
  7. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9240023.htm
  8. https://www.fda.gov/media/159893/download
  9. https://www.chemicalbook.com/SpectrumEN_79-41-4_IR1.htm
  10. https://www.chemicalbook.com/SpectrumEN_79-41-4_1HNMR.htm
  11. https://webbook.nist.gov/cgi/cbook.cgi?ID=C79414&Mask=400
  12. https://www.petrochemistry.eu/wp-content/uploads/2018/01/Safe_Handling_Manual.pdf
  13. https://www.sigmaaldrich.com/US/en/product/aldrich/155721
  14. https://www.procurementresource.com/production-cost-report-store/methacrylic-acid
  15. https://pubs.rsc.org/en/content/articlelanding/2018/cs/c8cs00117k
  16. https://link.springer.com/article/10.1134/S2070050421020057
  17. https://www.sumitomo-chem.co.jp/english/rd/report/files/docs/01_2004-2e.pdf
  18. https://prismaneconsulting.com/report-details/methacrylic-acid-maa-market
  19. https://www.databridgemarketresearch.com/reports/global-methacrylic-acid-market
  20. https://www.sciengine.com/doi/pdf/dc543247e96642edb6cebee3fa941a11
  21. https://onlinelibrary.wiley.com/doi/abs/10.1002/14356007.a16_441.pub2
  22. https://www.researchgate.net/publication/263859074_Synthesis_of_Bio-Based_Methacrylic_Acid_by_Decarboxylation_of_Itaconic_Acid_and_Citric_Acid_Catalyzed_by_Solid_Transition-Metal_Catalysts
  23. http://www.orgsyn.org/demo.aspx?prep=CV3P0030
  24. https://www.longdom.org/open-access-pdfs/silica-supported-heteropoly-catalysts-for-oxidation-of-methacrolein-tomethacrylic-acid-2157-7544-1000176.pdf
  25. https://www.mdpi.com/2227-9717/5/2/23
  26. https://www.sciencedirect.com/science/article/abs/pii/S0969806X99003321
  27. https://qatransport.com/en/knowledge/chemical-maa/
  28. https://www.ansys.com/blog/what-is-pmma-how-it-is-used-healthcare
  29. https://firstmold.com/guides/pmma-plastic/
  30. https://pom-material.com/blog/the-complete-guide-to-pmma-understanding-polymethyl-methacrylate-and-its-applications/
  31. https://pmc.ncbi.nlm.nih.gov/articles/PMC7599472/
  32. https://pmc.ncbi.nlm.nih.gov/articles/PMC12027187/
  33. https://www.intechopen.com/chapters/51535
  34. https://www.researchgate.net/publication/357354757_Hydrogels_based_on_polymethacrylic_acid_and_nanocellulose_with_potential_application_in_dental_treatments
  35. https://www.gantrade.com/faq/methacrylic-acid-maa
  36. https://pubs.acs.org/doi/10.1021/acsomega.0c05593
  37. https://www.m-chemical.co.jp/en/products/departments/mcc/mma_pmma/product/1201255_9386.html
  38. https://hansonchemicals.com/products/methacrylic-acid-maa/
  39. https://www.compositesone.com/product/polyester-vinyl-ester-resins/vinyl-ester/
  40. https://incomepultrusion.com/vinyl-ester-structure-properties-and-applications/
  41. https://teckrez.com/maa-79414/
  42. https://www.shokubai.co.jp/en/products/detail/methacrylate/
  43. https://shanghaichemex.com/product/methacrylic-acid/
  44. https://journals.sagepub.com/doi/10.1080/10915810500434191
  45. https://www.yogicoat.com/methacrylic-acid-copolymer-type-a/
  46. https://pharma.basf.com/chemistry/coating-polymers
  47. https://pmc.ncbi.nlm.nih.gov/articles/PMC11955852/
  48. https://www.futuremarketreport.com/industry-report/methacrylic-acid-mma-market
  49. https://growthmarketreports.com/report/bio-based-methacrylic-acid-market
  50. https://www.cosmeticsinfo.org/ingredient/methacrylic-acid/
  51. https://img.perfumerflavorist.com/files/base/allured/all/document/2016/04/pf.8453.pdf
  52. https://www.researchgate.net/publication/233139204_Study_on_Roman_Chamomile_Chamaemelum_nobile_L_All_Oil
  53. https://pubs.acs.org/doi/10.1021/acsengineeringau.1c00021
  54. https://doi.org/10.3389/fbioe.2020.00207
  55. https://doi.org/10.1021/ma0717744
  56. https://doi.org/10.1016/0014-3057(69)90098-6
  57. https://doi.org/10.1002/macp.202200428
  58. https://doi.org/10.1021/ma00120a035
  59. https://www.sciencedirect.com/science/article/abs/pii/S1004954122004268
  60. https://patents.google.com/patent/US6838515B2/en
  61. https://www.sciencedirect.com/science/article/abs/pii/S0079670006000335
  62. https://pubs.acs.org/doi/10.1021/ja00214a007
  63. https://pubs.acs.org/doi/10.1021/ja01571a076
  64. https://patents.google.com/patent/CN101560147A/en
  65. https://www.cdc.gov/niosh/npg/npgd0386.html
  66. https://hpvchemicals.oecd.org/UI/handler.axd?id=1dc3142c-8eba-47de-a1ed-35de65e652f2
  67. https://www.osha.gov/chemicaldata/694
  68. https://static1.squarespace.com/static/671c07889427681d9355cc40/t/678fbf225ce5e22c113224ec/1737473826494/MAA%2BSafe%2BHandling%2BManual%2B-%2BFINAL%2Bfor%2Bpublishing.pdf
  69. https://www.fishersci.com/store/msds?partNumber=AA15546&productDescription=keyword&vendorId=VN00024248&countryCode=US&language=en
  70. https://pubmed.ncbi.nlm.nih.gov/16596768/
  71. https://www.nj.gov/health/eoh/rtkweb/documents/fs/1199.pdf
  72. https://www.unigel.com.br/wp-content/uploads/2021/10/SDS_INHIBITED-GLACIAL-METHACRYLIC-ACID-GMAA_VER06.pdf
  73. https://www.ecetoc.org/wp-content/uploads/2014/08/JACC-035.pdf
  74. https://echa.europa.eu/substance-information/-/substanceinfo/100.001.096
  75. https://www.epa.gov/sites/default/files/2020-04/documents/section_5_test_information_received_under_tsca.pdf
  76. https://www.sepa.org.uk/media/61118/ippc-s401-large-volume-organic-chemicals-sector.pdf
  77. https://www.arkema.com/global/en/media/newslist/news/global/products/coatingresins/2025/20250122-bio-based-acrylic-binders/
  78. https://www.fda.gov/media/138078/download
  79. https://www.sciencedirect.com/science/article/abs/pii/S0920586113004033
Add your contribution
Related Hubs
User Avatar
No comments yet.