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Prop-2-enoic acid, more commonly known by its trivial name acrylic acid, is an unsaturated carboxylic acid with the molecular formula C₃H₄O₂, and it plays an essential role in both chemical manufacturing and polymer science.
Prop-2-enoic acid consists of a three-carbon chain that includes a carboxylic acid group (-COOH) at one end and a carbon-carbon double bond (C=C) between the second and third carbon atoms—hence the name “prop-2-enoic” (indicating a double bond starting at carbon 2 in a propyl chain).
Prop-2-enoic acid is highly reactive, particularly in addition reactions and polymerizations, making it a key monomer in the production of polyacrylic acid and various copolymers.
CAS Number: 35141-30-1
Molecular Formula: C10H27N3O3Si
Molecular Weight: 265.43
EINECS Number: 252-390-9
Synonyms: ACRYLIC ACID, prop-2-enoic acid, Vinylformic acid, Acroleic acid, Ethylenecarboxylic acid, Propene acid, Glacial acrylic acid, Kyselina akrylova, Acrylic acid, glacial, RCRA waste number U008, Acide acrylique, Acido acrilio, Caswell No. 009A, NSC 4765, CCRIS 737, HSDB 1421, UNII-J94PBK7X8S, EINECS 201-177-9, J94PBK7X8S, BRN 0635743, ACRLYLIC ACID, DTXSID0039229, CHEBI:18308, AI3-15717, NSC-4765, DTXCID8028, EC 201-177-9, 4-02-00-01455 (Beilstein Handbook Reference), ACRYLIC ACID (IARC), ACRYLIC ACID [IARC], Aqueous acrylic acid, Ethene carboxylic acid, 201-177-9, acrylic acid (acgih), 2-Propenoic acid, 79-10-7, Propenoic acid, ACRYLATE, Propenoate, Acrylic resin, Carbopol 934p, Viscalex HV 30, Carbomer 940, Carbopol 940, Aron, Antiprex A, Versicol E9, NSC4765, Acrylic acid resin, Acrysol ase-75, C3:1n-1, Versicol E 7, Versicol E15, Acrysol A 1, Acrysol A 3, Acrysol A 5, Acrysol A-1, Acrysol AC 5, Acrylic Acid-d3, Carbopol 960, Carboset 515, Primal Ase 60, Revacryl A191, Versicol K 11, Versicol S 25, Dispex C40, Acrysol WS-24, Cyguard 266, Joncryl 678, Jurimer AC 10H, Jurimer AC 10P, Nalfloc 636, Good-rite K 37, Revacryl A 191, Junlon 110, Viscon 103, Good-rite K 702, Good-rite K 732, Acrylic Acid-13C, Good-rite WS 801, NCGC00166246-01, Synthemul 90-588, Aron A 10H, Carboset Resin No. 515, OLD 01, PA 11M, PAA-25, Carbopol, P 11H, P-11H, WS 24, Acido acrilio [Spanish], Acide acrylique [French], WS 801, Kyselina akrylova [Czech], R968, UN2218, RCRA waste no. U008, Poly(acrylic acid) solution, allenediol, Acrysol lmw-20X, XPA, MFCD00004367, Dow Latex 354, Acrylic acid, inhibited, CH2=CHCOOH, Carbomer 934 (NF), Carbomer 940 (NF), Carbopol 910 (TN), Carbopol 934 (TN), Carbopol 940 (TN), Carbomer 934P (NF), Carbopol 934P (TN), Carbomer 910 (USAN), ACRYLIC ACID [MI], Carbomer 1342 (NF), Carbopol 1342 (TN), SCHEMBL4482, ACRYLIC ACID [HSDB], WLN: QV1U1, SCHEMBL24390, SCHEMBL26623, SCHEMBL93819, 9063-87-0, UN 2218 (Salt/Mix), Acrylic acid, p.a., 99%, SCHEMBL1020286, SCHEMBL6685040, SCHEMBL8669821, SCHEMBL9016194, SCHEMBL9925634, ACRYLIC ACID (13C3), CHEMBL1213529, SCHEMBL15348318, CIA32654, EIA25963, KLA13882, STR00040, VDA38798, Tox21_112372, Acrylic acid - stabilised with MEHQ, LMFA01030193, MSK001124, NSC106034, NSC106035, NSC106036, NSC106037, NSC112122, NSC112123, NSC114472, NSC165257, NSC226569, STL281870, AKOS000118799, DB02579, FA01586, FP34494, NSC-106034, NSC-106035, NSC-106036, NSC-106037, NSC-112122, NSC-112123, NSC-114472, NSC-165257, NSC-226569, CAS-79-10-7, Poly(acrylic acid), 25% soln in water, BP-30259, DB-220116, DB-251641, A0141, NS00001146, EN300-17959, C00511, C19501, D03392, D03393, D03394, D03395, D03396, D03397, Acrylic Acid contains 200ppm MEHQ as inhibitor, Acrylic acid, inhibited [UN2218] [Corrosive], A830860, Q324628, Z57127944, F0001-2070, InChI=1/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5, Acrylic acid, anhydrous, contains 200 ppm MEHQ as inhibitor, 99%, Acrylic acid, SAJ first grade, >=97.0%, contains 190-210 ppm MEHQ as stabilizer, 55927-87-2, (3-(TRIMETHOXYSILYL)PROPYL)DIETHYLENETRIAMINE, DIETHYLENETRIAMINO PROPYLTRIMETHOXYSILANE, TRIMETHOXYSILYLPROPYLDIETHYLENETRIAMINE, N-[3-(Trimethoxysilyl)propyl][2,2'-iminobis(ethanamine)], N-[3-(Trimethoxysilyl)propyl]-N'-(2-aminoethyl)ethylenediamine, Trimethoxy(9-amino-4,7-diazanonane-1-yl)silane, 3-[2-(2-Aminoethylamino)ethylamino]propyl-trimethoxysilane,95%, GE A-1130
Prop-2-enoic acid is an organic compound with the formula CH2=CHCOOH.
It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus.
This colorless liquid has a characteristic acrid or tart smell.
Prop-2-enoic acid is miscible with water, alcohols, ethers, and chloroform.
More than a million tons are produced annually.
These polymers are widely used in a range of industries, including the production of superabsorbent materials, adhesives, coatings, paints, textiles, and personal care products like gels or lotions.
This method requires nickel carbonyl, high pressures of carbon monoxide, and acetylene, which is relatively expensive compared to propylene.
Prop-2-enoic acid was once manufactured by the hydrolysis of acrylonitrile, a material derived from propene by ammoxidation, but this route was abandoned because it cogenerates ammonium side products, which must be disposed of.
Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.
Prop-2-enoic acid under supercritical carbon dioxide is thermodynamically possible, but efficient catalysts have not been developed.
Prop-2-enoic acid, an acrylic-acid precursor by dehydration, can be produced from sugars, but the process is not competitive.
Prop-2-enoic acid undergoes the typical reactions of a carboxylic acid.
When reacted with an alcohol, it forms the corresponding ester.
The esters and salts of acrylic acid are collectively known as acrylates (or propenoates).
The most common alkyl esters of acrylic acid are methyl, butyl, ethyl, and 2-ethylhexyl acrylate.
Prop-2-enoic acid and its esters readily combine with themselves (to form polyacrylic acid) or other monomers (e.g. acrylamides, acrylonitrile, vinyl compounds, styrene, and butadiene) by reacting at their double bond, forming homopolymers or copolymers, which are used in the manufacture of various plastics, coatings, adhesives, elastomers, as well as floor polishes and paints.
Prop-2-enoic acid is used in many industries, including the diaper industry, the water treatment industry, and the textile industry.
The annual worldwide consumption of acrylic acid is projected to reach more than an estimated 8,000 kilotons by 2020.
This increase is expected due to its use in new applications, including personal care products, detergents, and products for adult incontinence.
Prop-2-enoic acid is one of numerous organic compounds composing American Elements's comprehensive catalog of life science products.
American Elements supplies life science materials in most volumes including bulk quantities and also can produce materials to customer specifications.
Most materials can be produced in high and ultra high purity forms (99%, 99.9%, 99.99%, 99.999%, and higher) and to many standard grades when applicable including Mil Spec (military grade), ACS, Reagent and Technical Grades, Pharmaceutical Grades, Optical, Semiconductor, and Electronics Grades.
Prop-2-enoic acid is also valued for its ability to undergo both radical and ionic polymerization, allowing chemists to tailor the resulting polymers for specific mechanical, thermal, or chemical properties.
Despite its usefulness, prop-2-enoic acid is a corrosive and pungent liquid in its pure form, and it must be handled carefully due to its potential to cause severe skin burns, eye damage, and respiratory irritation if inhaled or exposed to the body in concentrated amounts.
The double bond in prop-2-enoic acid allows it to undergo addition reactions with a variety of radicals or electrophilic/nucleophilic species, enabling it to serve as a core monomer in the production of high-molecular-weight polymers.
Prop-2-enoic acid can be homopolymerized to form poly(acrylic acid), which is widely used for its thickening, dispersing, emulsifying, and binding properties, or it can be copolymerized with esters, acrylamides, styrene, or methacrylates to create specialty materials with enhanced mechanical strength, hydrophobicity, or elasticity.
Prop-2-enoic acid is a strategic industrial chemical, with millions of tons produced globally each year, primarily for use in adhesives, coatings, plastics, detergents, textiles, and superabsorbent polymers (SAPs) that are found in diapers, adult incontinence products, and feminine hygiene goods.
Its versatility comes from the fact that its polymers can either be soft and flexible, suitable for films and gels, or rigid and tough, useful in structural plastics, depending on the copolymer composition and process conditions.
Boiling point: 114-118 °C/2 mmHg (lit.)
Density: 1.03 g/mL at 25 °C (lit.)
Vapor pressure: 1 mm Hg (20 °C)
Refractive index: n20/D 1.459 (lit.)
Flash point: 257 °F
Form: Liquid
pKa: 10.17±0.19 (Predicted)
Specific Gravity: 1.03
Color: Clear yellow
Odor: Amine-like odor
Water Solubility: 1000 g/L at 20℃
Hydrolytic Sensitivity: 7: reacts slowly with moisture/water
BRN: 8421470
Prop-2-enoic acid is classified as corrosive and acutely toxic in its concentrated liquid form.
Exposure to its vapors can cause burning sensations in the nose and throat, coughing, and difficulty breathing, while direct skin contact may result in blistering, severe irritation, or chemical burns.
Therefore, when handled in industrial settings, it is essential to use personal protective equipment (PPE) such as gloves, goggles, and appropriate ventilation or respirators.
Furthermore, due to its volatility and flammability, it must be stored in cool, dry, and fire-resistant conditions, typically with inhibitors like MEHQ (monomethyl ether hydroquinone) added to prevent unintended polymerization during transport or storage.
Prop-2-enoic acid is an organic compound with the formula CH2=CHCOOH.
Prop-2-enoic acid is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus.
This colorless liquid has a characteristic acrid or tart smell.
Prop-2-enoic acid is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.
Prop-2-enoic acid is produced by oxidation of propylene, which is a byproduct of the production of ethylene and gasoline:
The word "acrylic" was coined in 1843, for a chemical derivative of acrolein, an acrid-smelling oil derived from glycerol.
Prop-2-enoic acid is a colorless to slightly yellow liquid with a strong, acrid, and irritating odor, and it is highly miscible with water, alcohol, and ether, which makes it relatively easy to incorporate into water-based or solvent-based formulations.
It has a boiling point of around 141°C, and because of the presence of the double bond adjacent to the carboxylic group, it is both acidic and highly reactive, particularly under free radical conditions, making it well-suited for polymerization and copolymerization with other vinyl monomers.
While Prop-2-enoic acid and its polymers are not inherently biodegradable in all forms, polyacrylic acid in water-soluble or lightly crosslinked forms can be broken down by UV light and microorganisms under certain conditions, and efforts are being made to develop bio-based acrylic acid from renewable feedstocks such as glycerol or lactic acid, which would reduce its dependence on petroleum-derived propylene.
This push aligns with global trends toward greener chemistry and sustainable polymer development.
In practice, Prop-2-enoic acid is available in various stabilized forms including glacial acrylic acid (a highly pure, anhydrous form), and it is often esterified or neutralized to form derivatives like methyl acrylate, ethyl acrylate, or acrylate salts, which are also widely used in adhesives, paints, pressure-sensitive labels, and sealants.
Many commercial formulations include acrylic acid as part of a copolymer mix to optimize properties such as tackiness, drying speed, elasticity, or resistance to UV or weathering.
Prop-2-enoic acid is composed of a vinyl group (–CH=CH₂) directly connected to a carboxylic acid group (–COOH), which results in a molecule that is both electron-rich and electrophilic, allowing it to participate in a wide array of organic transformations.
The conjugation between the carbon-carbon double bond and the carbonyl group in the carboxylic acid leads to increased reactivity in electrophilic addition reactions, and it also makes the molecule more prone to polymerization, especially under heat, UV radiation, or in the presence of peroxides or radical initiators.
Prop-2-enoic acid can be chemically transformed into many derivatives, such as acrylic esters (e.g., methyl acrylate, butyl acrylate), which are essential building blocks for coatings, elastomers, adhesives, and inks.
Through neutralization, it also forms acrylic salts, like sodium acrylate or ammonium acrylate, which are extensively used in superabsorbent polymers.
Additionally, the acid group allows for amidation, yielding compounds like acrylamide, and for crosslinking to produce hydrogels for medical and pharmaceutical applications.
The rich chemistry of the acrylic backbone allows researchers and manufacturers to fine-tune polymer properties for diverse applications, ranging from biodegradable plastics to responsive gels and smart coatings.
In modern manufacturing, Prop-2-enoic acid is used not only in bulk applications like paints and adhesives, but also in high-performance specialty materials such as ion-exchange resins, dental polymers, biomedical scaffolds, and controlled-release drug delivery systems.
The tunable nature of acrylic polymers allows them to respond to pH, temperature, or ionic strength, which is why they are used in contact lenses, wound dressings, and oral gels. In electronics and microfabrication, acrylic-based photoresists and dielectric coatings are vital to semiconductor processing and printed circuit boards.
From an environmental perspective, Prop-2-enoic acid in its free form is toxic to aquatic life at high concentrations, but it is also highly biodegradable under aerobic conditions when diluted and exposed to microbial action.
However, many acrylic polymers, especially those that are crosslinked or highly substituted, are persistent and resistant to breakdown, contributing to plastic pollution in some cases.
As a response, chemical engineers are now exploring bio-based routes to acrylic acid using fermentation of sugars or glycerol, as well as developing biodegradable copolymers that retain functional performance while being safer for the planet.
Uses:
Prop-2-enoic acid is a multifunctional organosilane commonly used as a coupling agent, adhesion promoter, and surface modifier in various industrial applications.
Prop-2-enoic acid can be used as a grafting agent to incorporate amine functional group onto the surface of various ordered mesoporous silica.
It can be also used in CO2 capture applications.
Prop-2-enoic acid is an extremely versatile chemical compound widely used across various industries due to its unique combination of chemical reactivity and polymer-forming ability.
One of its most significant uses is as a monomer in the production of polyacrylic acid and its copolymers, which serve as the basis for superabsorbent polymers (SAPs); these materials have the remarkable capacity to absorb and retain large volumes of water relative to their own weight, making them indispensable in products such as disposable diapers, adult incontinence pads, and feminine hygiene products, where moisture management and comfort are paramount.
In addition to its role in superabsorbents, Prop-2-enoic acid is utilized in the manufacture of adhesives and sealants, where polymers derived from it provide excellent bonding strength, flexibility, and resistance to environmental factors such as water, heat, and UV radiation.
These properties make acrylic-based adhesives essential in construction, automotive manufacturing, and packaging industries, where durable yet adaptable adhesive solutions are required.
Moreover, Prop-2-enoic acid and its derivatives are key ingredients in the formulation of paints, coatings, and varnishes, where they contribute to the creation of films that are tough, weather-resistant, and capable of protecting surfaces from corrosion and degradation.
These coatings are used extensively on everything from household walls and furniture to industrial machinery and vehicles, providing both aesthetic appeal and functional protection.
In the realm of textiles and fibers, Prop-2-enoic acid copolymers are used as thickeners, binders, and finishing agents, improving fabric durability, softness, and dye uptake, which ultimately enhances the quality and lifespan of clothing and upholstery.
Similarly, in the paper industry, acrylic acid-based polymers improve paper strength, gloss, and printability, enabling the production of high-quality paper products for printing and packaging.
Furthermore, Prop-2-enoic acid derivatives find important applications in the personal care and cosmetic industries, where they act as film formers, emulsifiers, and viscosity modifiers in products such as lotions, gels, hair sprays, and sunscreens, enhancing texture and stability while ensuring even application.
The biocompatibility of certain acrylic polymers has also allowed their use in medical applications, including hydrogels for wound dressings, drug delivery systems, and contact lenses, where their water-absorbing and flexible nature provide both comfort and functional benefits.
Lastly, acrylic acid is instrumental in the development of water treatment chemicals and detergents, where polymers based on acrylic acid help in dispersing solids, preventing scale formation, and improving cleaning efficiency in both industrial and household contexts.
The wide array of uses is a testament to acrylic acid’s importance as a foundational building block in modern chemical manufacturing, enabling the creation of products that significantly improve quality of life, industry productivity, and environmental management.
Beyond its fundamental role as a monomer in polymer production, Prop-2-enoic acid serves as a critical starting material for synthesizing a wide range of functional polymers and copolymers, which are engineered to meet specific performance requirements in highly specialized fields. For instance, in the automotive industry, acrylic acid-based polymers are employed in the manufacture of high-performance coatings that not only provide resistance to chemical corrosion and UV damage but also improve the aerodynamics and aesthetic finish of vehicles, thereby extending their operational lifespan and reducing maintenance costs.
In the electronics and electrical sectors, Prop-2-enoic acid derivatives are utilized to create insulating materials and protective coatings that safeguard delicate electronic components from moisture, dust, and mechanical wear. These polymers are essential in manufacturing circuit boards, display screens, and flexible electronics, where reliability and precision are critical.
Moreover, Prop-2-enoic acid plays an indispensable role in the agricultural industry, where water-absorbing acrylic polymers are incorporated into soil conditioners and controlled-release fertilizer formulations.
These polymers enhance the soil's water retention capacity, thereby reducing irrigation needs and improving nutrient delivery efficiency, which supports sustainable farming practices and optimizes crop yields, especially in arid or drought-prone regions.
The pharmaceutical and biomedical fields have also benefitted from Prop-2-enoic acid-based materials, particularly in developing hydrogels and drug delivery systems.
Polymers synthesized from acrylic acid can form biocompatible, water-swellable networks capable of encapsulating therapeutic agents, releasing them in a controlled manner over time, and providing scaffolds for tissue engineering and wound healing.
Such advanced applications demonstrate the compound’s versatility beyond traditional industrial uses.
Prop-2-enoic acid’s unique chemical structure allows it to be functionalized into responsive or “smart” materials, which change their properties in reaction to environmental stimuli such as pH, temperature, or ionic strength.
These materials have promising applications in fields such as environmental sensing, biotechnology, and advanced manufacturing, where materials that adapt dynamically can offer enhanced performance and new functionalities.
Safety Profile:
Prop-2-enoic acid is severely irritating and corrosive to the skin and the respiratory tract. Eye contact can result in severe and irreversible injury.
Low exposure will cause minimal or no health effects, while high exposure could result in pulmonary edema.
The LD50 is 340 mg/kg (rat, oral) with the lowest recorded LD50 being 293 mg/kg (oral, rat), comparable to ethylene glycol, which is indicative of being a potent poison.
Prop-2-enoic acid was once used as a synthetic food flavoring and was withdrawn by the FDA possibly due to cancerogenic effects observed in lab animals.
Animal studies showed that high doses of Prop-2-enoic acid decreased weight gain. Acrylic acid can be converted to non-toxic lactic acid.
Prop-2-enoic acid is a constituent of tobacco smoke.
Prop-2-enoic acid is classified as a corrosive and hazardous chemical, and exposure to its concentrated form can pose significant risks to human health and safety.
Due to its highly reactive nature and acidic properties, direct contact with acrylic acid can cause severe chemical burns to the skin and eyes, leading to pain, redness, blistering, and in extreme cases, permanent tissue damage or vision loss if not treated promptly.
Inhalation of Prop-2-enoic acid vapors or aerosols can result in irritation of the respiratory tract, causing symptoms such as coughing, shortness of breath, and inflammation of the mucous membranes, which may exacerbate pre-existing respiratory conditions like asthma.
Chronic or repeated exposure to Prop-2-enoic acid may lead to sensitization, whereby the immune system develops a heightened response, resulting in allergic dermatitis or respiratory sensitization upon subsequent exposures, even at lower concentrations.
Furthermore, Prop-2-enoic acid vapors are flammable and can form explosive mixtures with air, especially in confined or poorly ventilated areas, thereby necessitating strict controls on ignition sources and proper storage conditions to prevent fires or explosions.
From an environmental perspective, Prop-2-enoic acid is considered toxic to aquatic life, with the potential to cause long-lasting adverse effects in aquatic ecosystems if released in significant quantities.
This toxicity arises from its acidity and ability to interfere with the biological functions of aquatic organisms, which is why its disposal and accidental spills are regulated to minimize environmental contamination.
