Quick Search
Vinylformic acid is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus, with the formula CH₂=CHCOOH.
Vinylformic acid is a clear, colorless liquid with a pungent acrid odor, miscible with water, alcohols, ethers, and chloroform, and valued for its ability to undergo both addition reactions and polymerization.
Produced in millions of tons annually, Vinylformic acid serves as a key monomer in the manufacture of acrylates, resins, coatings, adhesives, superabsorbent polymers, and a wide range of consumer and industrial products.
CAS Number: 35141-30-1
EC Number: 252-390-9
Molecular Formula: C10H27N3O3Si
Molecular Weight: 265.43
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
Vinylformic acid is a simple unsaturated carboxylic acid with the molecular formula C₃H₄O₂.
Vinylformic acid is characterized by the presence of both a carboxyl group (–COOH) and a carbon–carbon double bond (–CH=CH₂), making it a highly reactive compound.
Vinylformic acid typically appears as a clear, colorless liquid with a pungent, acrid odor, and is miscible with water, alcohols, and ethers.
Owing to its unsaturated structure, Vinylformic acid readily undergoes addition reactions and polymerization, which underlies its extensive industrial use.
Vinylformic acid serves as a key monomer in the production of acrylate esters, resins, adhesives, coatings, superabsorbent polymers, and paints.
However, due to its strong corrosive nature and irritant properties, Vinylformic acid requires careful handling, storage in cool and well-ventilated areas, and protection from heat and light to prevent unwanted polymerization and hazardous exposure.
Vinylformic acid is an organic compound with the formula CH2=CHCOOH.
Vinylformic acid is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus.
Vinylformic acid has a characteristic acrid or tart smell.
Vinylformic 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.
Vinylformic 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 Vinylformic acid include ethenone and ethylene cyanohydrin.
Vinylformic acid under supercritical carbon dioxide is thermodynamically possible, but efficient catalysts have not been developed.
Vinylformic acid, an acrylic-acid precursor by dehydration, can be produced from sugars, but the process is not competitive.
Vinylformic acid undergoes the typical reactions of a carboxylic acid.
When reacted with an alcohol, Vinylformic acid forms the corresponding ester.
The esters and salts of Vinylformic acid are collectively known as acrylates (or propenoates).
The most common alkyl esters of Vinylformic acid are methyl, butyl, ethyl, and 2-ethylhexyl acrylate.
Vinylformic 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.
Vinylformic acid is used in many industries, including the diaper industry, the water treatment industry, and the textile industry.
The annual worldwide consumption of Vinylformic acid is projected to reach more than an estimated 8,000 kilotons by 2020.
This increase is expected due to Vinylformic acid's use in new applications, including personal care products, detergents, and products for adult incontinence.
Vinylformic 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.
Vinylformic 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, Vinylformic 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 Vinylformic 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.
Vinylformic 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.
Vinylformic 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.
Vinylformic acid's 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.
Vinylformic acid is classified as corrosive and acutely toxic in its concentrated liquid form.
Exposure to Vinylformic acid's 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, Vinylformic acid is essential to use personal protective equipment (PPE) such as gloves, goggles, and appropriate ventilation or respirators.
Furthermore, due to its volatility and flammability, Vinylformic acid 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.
Vinylformic acid is an organic compound with the formula CH2=CHCOOH.
Vinylformic 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.
Vinylformic acid is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.
Vinylformic 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.
Vinylformic 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.
Vinylformic acid 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 Vinylformic 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 Vinylformic 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, Vinylformic 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 Vinylformic acid as part of a copolymer mix to optimize properties such as tackiness, drying speed, elasticity, or resistance to UV or weathering.
Vinylformic 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.
Vinylformic 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, Vinylformic acid 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, Vinylformic 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, Vinylformic 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 Vinylformic acid using fermentation of sugars or glycerol, as well as developing biodegradable copolymers that retain functional performance while being safer for the planet.
Vinylformic acid is a simple yet highly reactive unsaturated carboxylic acid with the molecular formula C₃H₄O₂.
Structurally, Vinylformic acid contains both a carboxyl group (–COOH) and a vinyl double bond (–CH=CH₂), which confer a dual reactivity: it behaves as an organic acid while also participating in addition and polymerization reactions characteristic of alkenes.
In its pure state, Vinylformic acid is a clear, colorless liquid with a sharp, acrid odor.
Vinylformic acid has a melting point of about 14 °C and a boiling point near 141 °C.
Vinylformic acid is fully miscible with water and also dissolves readily in alcohols, ethers, and many organic solvents.
Because of the double bond, Vinylformic acid is highly prone to spontaneous polymerization when exposed to heat, light, or oxygen; therefore, commercial preparations are often stabilized with inhibitors such as hydroquinone or its derivatives to prevent hazardous runaway reactions during storage and transport.
From an industrial perspective, Vinylformic acid is one of the most important building blocks in modern polymer chemistry.
Vinylformic acid is used to manufacture acrylate esters, which are subsequently polymerized into materials for paints, adhesives, coatings, textiles, emulsions, plastics, and sealants.
One of Vinylformic acid's most critical applications is in the production of superabsorbent polymers (SAPs), which have exceptional water-retention capacity and are widely used in personal hygiene products (such as diapers and sanitary items) as well as in agriculture for soil conditioning.
Chemically, Vinylformic acid demonstrates high versatility.
The carboxyl group allows Vinylformic acid to undergo esterification and amidation reactions, while the double bond undergoes polymerization, copolymerization, and addition reactions, enabling the synthesis of a broad array of functional derivatives.
This duality explains Vinylformic acid's widespread role in both bulk and specialty chemicals.
Vinylformic acid can cause severe irritation and burns upon contact with skin or eyes, and inhalation of its vapors can damage the respiratory tract.
Prolonged or repeated exposure may lead to more serious systemic effects.
For this reason, handling requires strict safety measures, including the use of protective clothing, gloves, goggles, and fume extraction systems.
Safe storage conditions involve cool, well-ventilated environments, away from heat sources, oxidizing agents, and direct sunlight.
Overall, Vinylformic acid is both a valuable industrial raw material and a hazardous chemical, whose unique combination of acid and alkene functionalities makes it indispensable in polymer and materials science while simultaneously demanding careful management to ensure worker safety and process stability.
Market Overview of Vinylformic Acid:
Vinylformic acid, represents a cornerstone of the global chemical and polymer industries.
Vinylformic acid's market importance stems from its role as a primary monomer for the production of acrylate esters, resins, and superabsorbent polymers, which are vital in sectors ranging from construction and automotive to personal care and agriculture.
The global Vinylformic acid market is projected to remain strong due to rising demand for water-based adhesives, paints, and coatings, which are increasingly preferred over solvent-based alternatives for environmental reasons.
A particularly fast-growing segment is superabsorbent polymers (SAPs), driven by expanding populations, urbanization, and heightened hygiene awareness, fueling consumption in products such as diapers, sanitary napkins, and adult incontinence items.
Regionally, Asia-Pacific dominates production and consumption, led by China, South Korea, and Japan, owing to large chemical manufacturing bases and strong end-user industries.
North America and Europe remain significant markets, particularly in specialty coatings, adhesives, and construction materials, though their growth rates are comparatively stable.
Emerging economies in Latin America, the Middle East, and Africa are showing increased consumption due to infrastructure development and expanding consumer product industries.
Market dynamics are influenced by feedstock availability (propylene), raw material price fluctuations, and regulatory pressures aimed at improving sustainability and reducing volatile organic compound (VOC) emissions.
In response, producers are investing in bio-based Vinylformic acid derived from renewable feedstocks (such as glycerol), which is gaining attention as a more sustainable alternative.
Overall, the Vinylformic acid market is characterized by steady growth, high demand diversification, and strong ties to consumer and industrial product sectors, making it one of the most strategically important chemicals in the global value chain.
Uses of Vinylformic Acid:
Vinylformic acid, has a wide range of industrial uses due to its ability to undergo both acid-based and vinyl-type reactions.
Vinylformic acid's most significant application is in the production of acrylate esters, which are polymerized or copolymerized to create coatings, adhesives, sealants, plastics, and textiles with high durability and flexibility.
Another major use is in the manufacture of superabsorbent polymers (SAPs), particularly polyacrylic acid salts such as sodium polyacrylate, which are capable of absorbing and retaining large amounts of water and are therefore essential in hygiene products like diapers, sanitary napkins, and adult incontinence items, as well as in agriculture for soil moisture control.
Vinylformic acid derivatives are also critical in water-based coatings and pressure-sensitive adhesives, providing weather resistance and strong bonding properties for applications in construction, automotive, and packaging industries.
In addition, polyacrylic acid compounds serve as dispersants, scale inhibitors, and processing aids in detergents, water treatment systems, and oil recovery operations.
Beyond these bulk applications, Vinylformic acid finds roles in the textile and leather industries for finishing treatments that improve elasticity, strength, and waterproofing, and in medical materials such as hydrogels, wound dressings, and controlled drug delivery systems, where its absorbent and biocompatible properties are highly valued.
Vinylformic acid is a multifunctional organosilane commonly used as a coupling agent, adhesion promoter, and surface modifier in various industrial applications.
Vinylformic acid can be used as a grafting agent to incorporate amine functional group onto the surface of various ordered mesoporous silica.
Vinylformic acid can be also used in CO2 capture applications.
Vinylformic 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 Vinylformic acid's 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 Vinylformic acid's role in superabsorbents, Vinylformic 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, Vinylformic 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, Vinylformic 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, Vinylformic acid-based polymers improve paper strength, gloss, and printability, enabling the production of high-quality paper products for printing and packaging.
Furthermore, Vinylformic 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, Vinylformic acid is instrumental in the development of water treatment chemicals and detergents, where polymers based on Vinylformic 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 Vinylformic 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, Vinylformic 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, Vinylformic 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, Vinylformic 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, Vinylformic 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 Vinylformic acid-based materials, particularly in developing hydrogels and drug delivery systems.
Polymers synthesized from Vinylformic 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.
Vinylformic 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.
Vinylformic acid is an indispensable industrial chemical due to its dual reactivity as both a carboxylic acid and an unsaturated alkene.
Vinylformic acid's versatility allows it to serve as a precursor to a wide range of polymers and specialty chemicals.
The main areas of use include:
Acrylate Esters:
Vinylformic acid is esterified with alcohols (e.g., butanol, ethanol, 2-ethylhexanol) to produce acrylate esters.
These esters are widely polymerized or copolymerized to make paints, varnishes, adhesives, coatings, plastics, and textiles.
Superabsorbent Polymers (SAPs):
One of the largest applications involves converting Vinylformic acid into polyacrylic acid and its salts (e.g., sodium polyacrylate).
These superabsorbent polymers can retain hundreds of times their weight in water and are used in diapers, sanitary napkins, adult incontinence products, and agricultural water-retention aids.
Coatings and Adhesives:
Vinylformic acid derivatives form the backbone of pressure-sensitive adhesives, water-based coatings, sealants, and emulsion polymers, offering durability, flexibility, and weather resistance.
Vinylformic acid is used in construction materials (paints, plasters, sealants) and automotive coatings.
Textiles and Leather Treatments:
Vinylformic acid provides finishing agents that improve softness, elasticity, and resistance to wear.
Vinylformic acid is used in leather coatings to enhance waterproofing and surface strength.
Detergents and Water Treatment:
Polyacrylic acid derivatives act as dispersants and scale inhibitors in detergents, industrial water treatment, and cooling towers.
Medical and Hygiene Products:
Utilized in drug delivery systems, hydrogels, wound dressings, and dental materials, where Vinylformic acid's high absorbency and biocompatibility are valuable.
Other Specialized Uses:
Functions as a raw material in the synthesis of flocculants, thickeners, lubricants, and oil recovery chemicals.
Applied in the manufacture of polymers for packaging and protective coatings.
Benefits of Vinylformic Acid:
The benefits of Vinylformic acid, arise from its unique chemical structure, which combines a reactive vinyl double bond with a carboxyl functional group, making it an exceptionally versatile building block for industrial chemistry.
This dual reactivity allows Vinylformic acid to undergo polymerization, esterification, and copolymerization reactions, enabling the synthesis of a vast array of polymers, coatings, adhesives, and specialty materials.
One of Vinylformic acid's greatest advantages is its role in producing superabsorbent polymers, which provide life-enhancing benefits in hygiene products such as diapers and sanitary napkins by offering superior fluid absorption and retention.
Vinylformic acid's derivatives also enhance the durability, weather resistance, and flexibility of coatings, sealants, and adhesives, extending the lifespan of construction and automotive materials while reducing maintenance costs.
From an environmental perspective, Vinylformic acid-based waterborne coatings and adhesives contribute to lowering volatile organic compound (VOC) emissions compared to solvent-based systems, supporting cleaner and safer manufacturing practices.
In textiles and leather finishing, Vinylformic acid's polymers improve comfort, elasticity, and water resistance, while in water treatment and detergent applications, polyacrylic acid derivatives act as effective dispersants and scale inhibitors, ensuring cleaner operations and better equipment efficiency.
Furthermore, ongoing research into bio-based Vinylformic acid offers the potential benefit of reducing reliance on fossil resources, improving sustainability, and creating eco-friendly alternatives without sacrificing performance.
Overall, Vinylformic acid delivers benefits that span performance, functionality, and sustainability, securing its position as an essential raw material for both consumer products and advanced industrial applications.
Production of Vinylformic Acid:
The production of Vinylformic acid is primarily based on the oxidation of propylene, a major petrochemical feedstock derived from crude oil refining and steam cracking processes.
The dominant industrial route is a two-step catalytic oxidation process, where propylene is first oxidized to acrolein using bismuth molybdate or iron molybdate catalysts, and then further oxidized to Vinylformic acid with vanadium–molybdenum oxide catalysts under controlled temperatures.
This method provides high yields and remains the backbone of global Vinylformic acid manufacturing.
Alternative production routes include the direct oxidation of acrolein to Vinylformic acid and the hydrolysis of acrylonitrile, though these methods are less common today.
In recent years, significant research has been devoted to the development of bio-based Vinylformic acid, produced from renewable feedstocks such as glycerol (a byproduct of biodiesel production), lactic acid, or 3-hydroxypropionic acid, aiming to reduce dependence on fossil resources and lower environmental impact.
The shift toward sustainable production technologies is being accelerated by market demand for greener chemicals and by regulatory pressures to minimize carbon footprints.
Globally, production is concentrated in Asia-Pacific regions, particularly China, which dominates capacity and supply, followed by North America and Europe, where facilities are increasingly incorporating energy-efficient processes and safety systems to manage Vinylformic acid’s high reactivity and polymerization tendency.
The industry also integrates stabilizers such as hydroquinone into production and storage processes to prevent unwanted polymerization during handling.
Overall, the production of Vinylformic acid combines well-established petrochemical methods with emerging bio-based innovations, ensuring a balance between high-volume industrial demand and the growing push for sustainable chemistry.
History of Vinylformic Acid:
The history of Vinylformic acid, dates back to the mid-19th century, when it was first synthesized in 1843 by the French chemist Frédéric Berthelot through the oxidation of acrolein.
Initially, Vinylformic acid's applications were limited to laboratory research, as industrial-scale production was not yet feasible.
With the advancement of organic chemistry and the rise of the petrochemical industry in the early 20th century, Vinylformic acid began to attract attention as a valuable monomer for synthetic materials.
By the 1930s, German chemical companies pioneered Vinylformic acid's commercial production and use, particularly in coatings and plastics, recognizing its potential to form durable and versatile polymers.
After World War II, demand for Vinylformic acid grew rapidly as industries required new materials for construction, automotive manufacturing, textiles, and adhesives, driving large-scale production plants in Europe, the United States, and later in Asia.
The invention of superabsorbent polymers in the 1960s and 1970s, derived largely from Vinylformic acid, marked a turning point, as these materials revolutionized hygiene products like diapers and sanitary napkins, establishing Vinylformic acid as an essential global commodity.
In recent decades, production methods have shifted from small-batch laboratory synthesis to highly optimized, large-scale catalytic oxidation of propylene, ensuring efficiency and scalability.
Today, the history of Vinylformic acid continues to evolve with the development of bio-based production technologies, reflecting a broader movement toward sustainability in the chemical industry.
From its humble origins in 19th-century research to its present role as a cornerstone of modern polymer chemistry, Vinylformic acid has consistently shaped—and been shaped by—the industrial and consumer needs of each era.
Handling and Storage of Vinylformic Acid:
Handling:
Avoid inhalation of vapors and prevent contact with skin, eyes, and clothing.
Use only in well-ventilated areas or under fume hoods.
Do not eat, drink, or smoke while handling.
Wash hands and face thoroughly after use.
Use explosion-proof equipment where vapors may accumulate.
Storage Conditions:
Store in a cool, dry, well-ventilated place away from heat, sparks, open flame, and direct sunlight.
Keep container tightly closed.
Always store with polymerization inhibitors (e.g., hydroquinone) to prevent spontaneous polymerization.
Incompatibilities:
Avoid contact with strong oxidizing agents, strong bases, amines, and reducing agents.
Do not store near peroxides or other radical initiators.
Stability and Reactivity of Vinylformic Acid:
Stability:
Unstable if not properly inhibited; may polymerize violently when exposed to heat, light, or oxygen.
Stable under recommended storage conditions with inhibitors.
Reactivity:
Readily undergoes addition and polymerization reactions; can react exothermically with alkalis and oxidizing agents.
Hazardous Decomposition Products:
Burning or thermal decomposition may release carbon monoxide, carbon dioxide, and irritating acrid fumes.
Conditions to Avoid:
Elevated temperatures, direct sunlight, contamination with incompatible materials, and loss of polymerization inhibitor.
First Aid Measures of Vinylformic Acid:
Inhalation:
Remove victim to fresh air immediately.
If breathing is difficult, provide oxygen.
Seek medical attention if symptoms persist.
Skin Contact:
Wash affected area with plenty of soap and water for at least 15 minutes.
Remove contaminated clothing and shoes.
Seek medical advice if irritation or burns occur.
Eye Contact:
Rinse cautiously with water for several minutes while holding eyelids open.
Remove contact lenses if easy to do.
Obtain immediate medical attention.
Ingestion:
Rinse mouth with water.
Do not induce vomiting.
Give water to drink if conscious.
Seek immediate medical attention.
Firefighting Measures of Vinylformic Acid:
Suitable Extinguishing Media:
Water spray, foam, dry chemical powder, or carbon dioxide (CO₂).
Unsuitable Media:
High-pressure water jets, as they may spread the material.
Special Hazards:
Vapors may form explosive mixtures with air.
Burning releases toxic and irritating fumes such as CO and CO₂.
Risk of violent polymerization in fire conditions.
Protective Equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear.
Cool closed containers with water spray to prevent rupture.
Accidental Release Measures of Vinylformic Acid:
Personal Precautions:
Evacuate unnecessary personnel.
Wear appropriate PPE (gloves, goggles, respirator).
Avoid inhalation of vapors and skin/eye contact.
Ensure adequate ventilation.
Remove ignition sources.
Environmental Precautions:
Prevent spillage from entering drains, surface waters, or soil.
Vinylformic acid is harmful to aquatic organisms.
Containment & Cleanup:
Contain the spill with inert absorbent (sand, vermiculite).
Collect in sealed, labeled containers for disposal.
Neutralize small spills with dilute alkali under controlled conditions.
Wash spill area with plenty of water.
Exposure Controls / Personal Protective Equipment of Vinylformic Acid:
Engineering Controls:
Use local exhaust ventilation or fume hoods to keep airborne concentrations below exposure limits.
Explosion-proof ventilation may be required in high-vapor environments.
Respiratory Protection:
If vapor levels exceed exposure limits, use a NIOSH-approved organic vapor respirator or self-contained breathing apparatus.
Eye Protection:
Wear safety goggles or chemical splash-resistant face shields.
Skin Protection:
Use protective gloves (nitrile, neoprene, or butyl rubber), chemical-resistant clothing, and protective footwear.
Hygiene Measures:
Do not eat, drink, or smoke while handling.
Wash hands, face, and exposed skin thoroughly after handling.
Remove contaminated clothing and wash before reuse.
Identifiers of Vinylformic Acid:
CAS Number: 79-10-7
EC Number (EINECS): 201-177-9
RTECS Number: AS4375000
UN Number (Transport): 2218 (Acrylic acid, stabilized)
Molecular Formula: C₃H₄O₂
Molar Mass: 72.06 g/mol
Structural Formula: CH₂=CH–COOH
InChI: InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
InChI Key: QJGQUHMNIGDVPM-UHFFFAOYSA-N
SMILES: C=CC(=O)O
HS Code: 29161100 (Carboxylic acids with unsaturated monocarboxylic function)
IUPAC Name: Vinylformic acid
Common Name: Acrylic acid
UNS No. 2218 (Acrylic acid, stabilized)
CAS Registry Number: 79-10-7
EC Number (EINECS): 201-177-9
RTECS Number: AS4375000
UN Number (Transport): 2218 (for stabilized acrylic acid)
HS Code (Customs): 29161100 – Carboxylic acids with unsaturated monocarboxylic function
Molecular Formula: C₃H₄O₂
Molecular Weight: 72.06 g/mol
Structural Formula: CH₂=CH–COOH
InChI: InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
InChI Key: QJGQUHMNIGDVPM-UHFFFAOYSA-N
SMILES: C=CC(=O)O
REACH Registration No.: 01-2119459307-35-XXXX
EPA TSCA Inventory: Listed
DSL/NDSL (Canada): Listed
KEGG Compound ID: C01057
Properties of Vinylformic Acid:
Chemical Formula: C₃H₄O₂
Molecular Weight: 72.06 g/mol
Appearance: Clear, colorless liquid with a pungent, acrid odor
Odor Threshold: ~1 ppm (strong, irritating)
Density: 1.051 g/cm³ at 20 °C
Melting Point: 12–14 °C
Boiling Point: 141 °C at 101.3 kPa
Flash Point: 50–54 °C (closed cup)
Autoignition Temperature: ~395 °C
Explosive Limits (Vapor in air): Lower: 2.5 vol%; Upper: 8.0 vol%
Vapor Pressure: 3.7 kPa at 20 °C (≈28 mmHg)
Vapor Density (air = 1): 2.5
Refractive Index: nᴅ²⁰ = 1.422–1.425
pKa (acid dissociation constant): 4.25 at 25 °C
Viscosity: 1.3 mPa·s at 25 °C
Surface Tension: 27.8 mN/m at 20 °C
Solubility in Water: Miscible in all proportions
Solubility in Organic Solvents: Soluble in ethanol, diethyl ether, acetone, benzene
Partition Coefficient (log Kow): 0.46 (low bioaccumulation potential)
Stability: Polymerizes easily without inhibitor; requires stabilizers like hydroquinone
Odor Character: Sharp, vinegar-like, irritating
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
Formula: C₃H₄O₂
Molecular Weight: 72.06 g/mol
Structural Formula: CH₂=CH–COOH
Physical State: Clear, colorless liquid
Odor: Sharp, acrid, vinegar-like
Taste: Pungent, sour (not safe for ingestion)
Hygroscopic: Slightly hygroscopic, absorbs moisture
Melting Point / Freezing Point: 12–14 °C
Boiling Point: 141–142 °C at 101.3 kPa
Flash Point: 50–54 °C (closed cup)
Autoignition Temperature: ~395 °C
Heat of Vaporization: ~34 kJ/mol at 25 °C
Heat of Combustion: –1,358 kJ/mol
Flammability: Flammable liquid (GHS Category 3)
Explosive Limits in Air: Lower 2.5 vol%; Upper 8.0 vol%
Vapor Pressure: 3.7 kPa at 20 °C
Vapor Density (air = 1): 2.5
pKa: 4.25 at 25 °C (weak acid, comparable to acetic acid)
Log Kow: 0.46 (low lipophilicity, low bioaccumulation potential)
Henry’s Law Constant: 6.8 × 10⁻⁷ atm·m³/mol (low volatility from water)
Refractive Index: 1.422–1.425 at 20 °C
Surface Tension: 27.8 mN/m at 20 °C
Viscosity: 1.3 mPa·s at 25 °C
Solubility Profile:
Water: Fully miscible in all proportions
Organic Solvents: Miscible with ethanol, acetone, ether, chloroform, benzene
Partition Behavior: Hydrophilic, remains mostly in aqueous phase in environmental systems
