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Acrylic acid is an organic compound with the formula CH2=CHCOOH.
Acrylic acid is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus.
CAS Number: 79-10-7
EC Number: 201-177-9
IUPAC Name: Prop-2-enoic acid
Chemical formula: C3H4O2
Other names: ACRYLIC ACID, 2-Propenoic acid, 79-10-7, prop-2-enoic acid, Propenoic acid, Vinylformic acid, Acroleic acid, Ethylenecarboxylic acid, Propene acid, ACRYLATE, Propenoate, 9003-01-4, Glacial acrylic acid, Kyselina akrylova, Acrylic acid, glacial, RCRA waste number U008, Acide acrylique, Acido acrilio, Caswell No. 009A, Carbopol 934p, Viscalex HV 30, NSC 4765, CCRIS 737, Acrylic resin, HSDB 1421, UNII-J94PBK7X8S, EINECS 201-177-9, J94PBK7X8S, Carbopol 940, BRN 0635743, ACRLYLIC ACID, DTXSID0039229, CHEBI:18308, AI3-15717, NSC-4765, DTXCID8028, Aron, Antiprex A, Versicol E9, NSC4765, EC 201-177-9, Acrylic acid resin, Acrysol ase-75, C3:1n-1, Versicol E 7, Versicol E15, 4-02-00-01455 (Beilstein Handbook Reference), Acrysol A 1, Acrysol A 3, Acrysol A 5, Acrysol A-1, Acrysol AC 5, 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, Good-rite WS 801, NCGC00166246-01, Synthemul 90-588, Aron A 10H, Carboset Resin No. 515, ACRYLIC ACID (IARC), ACRYLIC ACID [IARC], 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, allenediol, Acrysol lmw-20X, XPA, Aqueous acrylic acid, 25987-55-7, Dow Latex 354, Ethene carboxylic acid, Acrylic acid, inhibited, CH2=CHCOOH, (stabilized with MEHQ), Carbomer 934 (NF), Carbomer 940 (NF), Carbomer 941 (NF), Carbopol 910 (TN), Carbopol 934 (TN), Carbopol 940 (TN), Carbopol 941 (TN), Carbomer 934P (NF), Carbopol 934P (TN), Carbomer 910 (USAN), ACRYLIC ACID [MI], Carbomer 1342 (NF), Carbopol 1342 (TN), ACRYLIC ACID [HSDB], WLN: QV1U1, average Mv ~450,000, UN 2218 (Salt/Mix), Acrylic acid, p.a., 99%, CHEMBL1213529, STR00040, Tox21_112372, LMFA01030193, MFCD00004367, NSC106034, NSC106035, NSC106036, NSC106037, NSC112122, NSC112123, NSC114472, NSC165257, NSC226569, STL281870, AKOS000118799, DB02579, 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, 1ST001124, 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, 1204391-75-2, 55927-87-2, 9063-87-0
This colorless liquid has a characteristic acrid or tart smell.
Acrylic acid is miscible with water, alcohols, ethers, and chloroform.
More than a million tons are produced annually
Because acrylic acid and its esters have long been valued commercially, many other methods have been developed.
Most have been abandoned for economic or environmental reasons.
An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):
This method requires nickel carbonyl, high pressures of carbon monoxide, and acetylene, which is relatively expensive compared to propylene.
Acrylic 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.
Acrylic acid is an organic molecule and the simplest of the unsaturated acids.
At room temperature, acrylic acid is a liquid and has a characteristic acid and tart aroma.
Acrylic acid is corrosive in liquid and vapor forms. Acrylic acid is used mainly in the formation of polymers.
Acrylic acids uses include plastics, coatings, adhesives, elastomers, paints, and polishes.
Additionally, acrylic acid is used in the production of hygienic medical products, detergents, and wastewater treatment chemicals.
The low toxicity of acrylic acid is due to its corrosive nature.
Studies have suggested that acrylic acid poses some reproductive hazards; however, conflicting data exist regarding the genotoxicity of acrylic acid.
Acrylic acid's production and use in the manufacture of plastics, paint formulations, leather finishings, paper coatings, and in medicine and dentistry for dental plates, artificial teeth, and orthopedic cement may result in its release to the environment through various waste streams.
Acrylic acid has also been identified in nine species of chlorophyceae algae, 10 species of rhodophyceae algae, and in the rumen fluid of sheep.
If released to air, a vapor pressure of 3.97 mmHg at 25 °C indicates acrylic acid will exist solely as a vapor in the ambient atmosphere.
Vapor-phase acrylic acid will be degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2 days.
If released to soil, acrylic acid is expected to have very high mobility.
Volatilization from moist soil surfaces is expected to be slow.
Acrylic acid may potentially volatilize from dry soil surfaces based upon its vapor pressure.
If released into water, acrylic acid is not expected to adsorb to suspended solids and sediment in the water column.
Biodegradation under both aerobic and anaerobic conditions is expected to occur.
Acrylic acid is an important polymer as raw material for many industrial and consumer products.
Acrylic acid can numerous to apply for surface coatings, textiles, adhesives, paper treatment, baby diapers, feminine hygiene products detergents and super absorbent polymers as known .
Currently, most acrylic acid is obtained from the catalytic partial oxidation of propene which is a by-product of ethylene and gasoline production.
In this two-step oxidation reaction via acrolein is usually preferred, achieving about 90 % overall yield.
However, this conventional process affects global CO2 emissions: 175 kg/ton of CO2 has been released in converting propene to acrylic acid (Segawa, 2014) and petrochemical carbons sources are limited and not renewable.
The global acrylic acid market sizes is growing. Because acrylic acid demands for super absorbent polymers is expected the growth.
This process feedstock, propene, is related to volatile crude oil prices.
Therefore, alternative methods have been studied such as biomass resources.
Acrylic acid is encouraging to find renewable alternatives to produce acrylic acid in more environmentally friendly and economical way.
Most of the feedstock for producing the acrylic acid, the quantitative conversion to lactic acid would open a new market for renewable resources.
There are recent advances in the research and development of acrylic acid via the fermentation of renewable sources using microorganisms that ferment the 3-hydroxyproponic acid that is then dehydrated to from acrylic acid.
In this paper, we focus on the process after the dehydration of 3-hydroxypropionic acid to produce acrylic acid.
We conducted simulations and designed proposed model using commercial simulators that referred as the patent product components.
This process introduced a quencher using solvent to cool the main stream in order to separate water in extractor unit and to avoid acrylic acid polymerization.
Acrylic acid remove water from fermentation reaction of biomass and catalytic dehydration reaction of 3-HP.
By first removing water from the quencher through solvent, the initial investment cost and the operating cost of the separation process can be reduced.
Appearance: Clear, colorless liquid
Odor: Acrid
Density: 1.051 g/mL
Melting point: 14 °C
Boiling point: 141 °C
Solubility in water: Miscible
log P: 0.28
Vapor pressure: 3 mmHg
Acidity (pKa): 4.25 (H2O)
Molecular Weight: 72.06 g/mol
XLogP3: 0.3
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 1
Exact Mass: 72.021129366 g/mol
Monoisotopic Mass: 72.021129366 g/mol
Topological Polar Surface Area: 37.3Ų
Heavy Atom Count: 5
Complexity: 55.9
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Acrylic acid is used in the manufacture of plastics, paint formulations, and other products. Exposure occurs primarily in the workplace.
Acrylic acid is a strong irritant to the skin, eyes, and mucous membranes in humans.
No information is available on the reproductive, developmental, or carcinogenic effects of acrylic acid in humans. Animal cancer studies have reported both positive and negative results.
EPA has not classified acrylic acid for carcinogenicity.
Acrylic acid is used in the manufacture of plastics, paint formulations, and other products.
Exposure occurs primarily in the workplace.
Acrylic acid is a strong irritant to the skin, eyes, and mucous membranes in humans.
No information is available on the reproductive, developmental, or carcinogenic effects of acrylic acid in humans.
Animal cancer studies have reported both positive and negative results.
EPA has not classified acrylic acid for carcinogenicity.
Copolymer hydrogels of acrylic acid (AA) with N,N-dimethylacrylamide (NNDMAAm) were synthesized by solution free radical polymerization at different feed mol monomer ratios.
The monomer reactivity ratios were determined by Kelen-Tüdös method.
According to that, the monomer reactivity ratios for poly(AA-co-NNDMAAm) were r1 = 0.650 (M1=AA) and r2= 1.160 (M2=NNDMAAm), (r1 x r2= 0.753).
The effect of reaction parameters including:
the concentration of cross-linking reagent, monomer concentration, pH, temperature, salt solutions, and solvent polarity on the water absorption have been studied.
The hydrogels achieved water-absorption values of 544 g water/ g xerogel for the copolymer poly(AA-co-NNDMAAm) 3:1 atpH 5.
Low critieal solution temperature (LCST) values of hydrogels, showed an increase whenthe hydrophilic Acrylic acid moiety eontent increased in the copolymers.
In recent years, considerable research attention has been focused on intelligent polymer materials, especially hydrogels that contain functional groups and are able to alter their volume or other properties in response to environmental stimuli, such as pH, temperature and electric field, among others.
Acrylic acid is cross-linked three-dimensional hydrophilic polymer networks that swell but do not dissolve when brought into contact with water.
Acrylic acid are a class of polymeric materials with the ability to hold a substantial amount of water, presenting a soft, rubbery-like consisteney, and low interfacial tensión parameters.
Acrylic acid properties mainly depend on the degree of cross-linking, the chemical composition of the polymeric chains, and the interaction between the network and surrounding liquids..
Hydrophilicity or high water retention in hydrogels is attributed to the presence of hydrophilic groups, such as carboxylic acids, amides, and alcohols.
The structural features of these materials domínate its surface properties, permeselectivity and permeability, giving hydrogels their unique, interesting properties, and the similarity of their physical properties to those present in livingtissues.
The important swelling of hydrogels based on acrylic acid is facilitated by the presence of carboxylic acid groups in the polymer chain, which are strongly associated with water molecules.
These groups are readily ionisable and sensitive to the effeets of pH and ionic strength.
Thus, the equilibrium swelling of Acrylic acid copolymers are affected by the solution's pH and ionic strength in which they are swelled.
Polymer gels play an important role in many emerging technological areas such as drug delivery, sensors, and superabsorbent materials.
Copolymerization reaction of two monomers is an effective method to modify the physical properties of polymer gels
Several authors have studied the Low Critieal Solution Temperature (LCST) in poly(isopropyl acrylamide) hydrogels (PNIPAAm) and reported that incorporation of an hydrophilic comonomer leads to a higher values of LCST, while incorporation of a hydrophobic monomer decreases the Low Critieal Solution Temperature.
A good balance between hydrophilic and hydrophobic interactions in the polymer, explains this sharp phase transition.
The transition temperature ofthe cross-liked gels changed according to the feed monomer ratio used in the copolymerization reaction.
The pH value ofthe solution strongly affected the swelling ratio.
Several methods to detect LCST have been reported, including light scattering to detect the coil-to-globule transition , turbidimetric measurements to achieve phase transition or differential scanning calorimetry (DSC) to measure the transition heat.
Acrylic acid are also used in pharmacological applications, in controlled release, water purification, drug reléase system, and others.
We have previously published the synthesis and swelling properties of hydrogels from functional vinyl monomers.
These systems showed that the copolymers containing acrylic acid and acrylamide derivative moieties are very sensitive to stimuli as pH, temperature, ionic strength, and copolymer composition.
Thus, the influence of water absorption at room temperature was strong at pH 5 and pH 7, with maximums between 1200 and 1600 %, when the poly(2-hydroxyethylmethacrylate-co-maleoylglycine) P(HEMA-co-MG) was richest in HEMA monomer unit.
The aim of this paper is to synthesize by solution, free radical polymerization copolymers of acrylic acid (AA) with N,N¢-dimethylacrylamide (NNDMAAm), at different feed monomer ratios and degrees of cross-linking, and to study the swelling properties of these hydrogel systems in distilled water and ethanol at different pH, temperature, time, and salt concentration.
The thermal properties of the copolymers, specially the glass transition temperatures (Tg), and the thermal decomposition will also be determined.
Acrylic acid esters in water-based coating, in particular butyl acrylates, are replacing more an more solvent borne paints.
Typical commodity esters of acrylic acid are methyl-, ethyl-, n-butyl- and 2-ethylhexyl (2EHA)- esters.
The strongest growth rates are expected with 2EHA, followed by butyl acrylate, methyl acrylate and ethyl acrylate.
Esters from alcohols like polyols, isobutanol, hexanol and iso-octanol are of less importance in the polymer industry.
Acrylic polymers are considered as non toxic and are gaining more and more importance.
Typically these esters are catalysed at a temperature range between 70°C (160°F) and 130°C (265°F) to avoid the formation of the ethers from the alcohols.
Acrylic acid is an unsaturated carboxylic acid.
Acrylic acid reacts as a vinyl compound and as a carboxylic acid.
Acrylic acid readily undergoes polymerization and addition reactions.
Acrylic acid can be used as a carboxylic acid to produce acrylic esters, acrylamide, N-substituted acrylamides and acrylyl chloride by common methods.
Copolymers can be produced with acrylic and methacrylic esters, acrylonitrile, maleic acid esters, vinyl acetate, vinyl chloride, vinylidene chloride, styrene, butadiene and ethylene.
Homopolymers of acrylic acid and copolymers which contain a preponderance of acrylic acid have a glassy consistency and are frequently soluble in water.
They can be used in the form of their free acids and ammonium and alkali salts in many different applications, such as thickeners, dispersing agents, flocculants, protective colloids for stabilizing emulsions and polymer dispersions, wetting agents, coatings and textile finishes.
Acrylic acid readily undergoes addition reactions with a wide variety of organic and inorganic compounds.
This makes it a very useful feed-stock for the production of many low molecular compounds.
For instance, acrylic acid can be used to produce derivatives of propionic acid with water, alcohols, amines, halogens and chlorinated hydrocar-bons.
Acrylic acid can also be used with other substances to produce unsaturated fatty acids, heterocyclic compounds and Diels-Alder addition products.
Acrylic acid and esters are versatile monomers used as building blocks for thousands of polymer formulations.
They are flammable, reactive, volatile liquids based on an alpha-, beta-unsaturated carboxyl structure.
Incorporation of varying percentages of acrylate monomers permits the production of many formulations for latex and solution copolymers, copolymer plastics and cross-linkable polymer systems.
Their performance characteristics—which impart varying degrees of tackiness, durability, hardness, and glass transition temperatures—promote consumption in many end-use applications.
Major markets for the esters include surface coatings, textiles, adhesives, and plastics.
Polyacrylic acid or copolymers find applications in superabsorbents, detergents, dispersants, flocculants, and thickeners.
Superabsorbent polymers (SAPs) are used primarily in disposable diapers.
Crude acrylic acid (CAA) is made by the oxidation of propylene.
About half of the CAA is converted to acrylate esters, and the remaining half is purified to 98–99.5% purity to glacial acrylic acid (GAA).
In turn, GAA is converted into polyacrylic acid, which can be further modified to produce superabsorbent polymers (SAPs) and other polyacrylic acid copolymers used as dispersants/antiscalants, anionic polyelectrolytes for water treatment, and rheology modifiers.
Growth in GAA consumption is forecast at about 3.5% per year during 2020–25.
More information on the superabsorbent polymers market can be found in the CEH Superabsorbent Polymers report.
Acrylate esters impart many desirable qualities to polymeric materials, such as color stability and clarity, heat and aging resistance, good weatherability, and low-temperature flexibility.
One of the important properties of acrylate esters is their glass transition temperature (Tg), which influences the characteristic temperature at which the resultant polymer undergoes a change from a brittle system to a softer, more flexible one.
The Tg has a major influence on the minimum film formation temperature of the coating or adhesive.
(The minimum film formation temperature is also influenced by the levels and types of cosolvents and coalescing agents, plasticizers, and other additives added to the polymer or to the coating formulation.)
The shorter-chain monomers (e.g., methyl acrylate) produce harder, more brittle polymers, while the longer-chain monomers (e.g., 2-ethylhexyl acrylate) impart softness and flexibility.
Growth in demand for crude acrylic acid is forecast at 3.5–4% per year during 2020–25, driven by growth in superabsorbent polymers and acrylate esters.
SAP growth will be strongest in mainland China and other parts of Asia, but will be much more moderate in the mature regions of North America, Western Europe, and Japan.
SAP is being used in greater quantities as the population in developing nations continues to increase its use of disposable diapers and incontinence products.
Acrylic esters are used principally in coatings and adhesives, which are also areas of growth in developing countries.
Clear, colorless liquid with a characteristic acrid odor. It is miscible with water, alcohols and ethers.
Acrylic acid will undergo the typical reactions of a carboxylic acid, as well as reactions of the double bond similar to those of the acrylate esters.
Acrylic acid lends itself to polymer preparation as well as use as a chemical intermediate.
Acrylate esters, both mono- and multifunctional, are generally prepared from acrylic acid
Paints and Coatings
Adhesives
Detergents
Diapers
Floor Polish
Variety of Medical Applications
Impact strength, flexibility, durability, toughness
Weather resistance, moisture resistance
Crosslinking sites, acid group reacts readily with alcohols, acrylates and styrenics
Hardness, wet and dry adhesion and abrasion resistance are also properties of GAA copolymers
Acrylic, any of a broad array of synthetic resins and fibres that are based on derivatives of acrylic and methacrylic acid.
Both acrylic acid (CH2=CHCO2H) and methacrylic acid (CH2=C[CH3]CO2H) have been synthesized since the mid-19th century, but the practical potential of materials related to these compounds became apparent only about 1901, when German chemist Otto Röhm published doctoral research on polymers of acrylic esters.
Beginning on a commercial basis in the 1930s, esters of acrylic acid were polymerized to form the polyacrylate resins, which are now important constituents of acrylic paints, and methacrylic acid esters were polymerized to polymethyl methacrylate, a clear plastic sold under trademarks such as Plexiglas and Perspex.
In 1950 Orlon, the first commercially successful acrylic fibre, was introduced by E.I. du Pont de Nemours & Company (now DuPont Company). Acrylic and modacrylic fibres are based on polyacrylonitrile.
Other acrylics include cyanoacrylate resins, made into fast-acting adhesives; poly-2-hydroxyethyl methacrylate, abbreviated polyHEMA, made into soft contact lenses; polyacrylamide resins, used as flocculents in water clarification; and rubber products made of polyacrylate elastomer.
Acrylic acids are colorless and pungent-smelling acids that exist as liquids at room temperature and pressure.
There are 2 commercial grades, which are used for esterification (94%) and used to make water-soluble resins (98%-99.5%). It polymerizes easily when exposed to light, heat or metal.
An x indicator must always be present for polymerization.
Acrylic Acid belongs to the class of organic compounds, it is also specified as 2-Propenoic Acid or Acrylate.
Acrylic Acid exists as a water-soluble liquid and a weakly acidic chemical compound.
Acrylic Acid is also known as the simplest chemical compound of p-Unsaturated carboxylic acid.
When its structure is examined, Acrylic Acid is seen that a vinyl group is attached to a carbonyl group and that these compounds of this acid go through processes similar to the reactions of carboxylic acids.
A double bond and a functional carboxylic acid group in its structure play an important role in giving characteristic reactions similar to the properties of the carboxylic acid.
Acrylic Acid is an organic acid with the formula CH2 = CH-COOH, also called propenoic acid.
In industry, the reaction of acetylene and carbon monoxide with nickel catalyst in the presence of water is obtained by hydrolysis of the more common acrylonitrile compounds.
Acrylic Acid is the starting material for the production of polymers.
Acrylic compounds are the raw material of various compounds such as molded building materials, optical instruments, woven fiber, jewellery, adhesives, coating materials.
For example, orlon and acrylan are the trade names of tab acrylic materials for plexiglass glass and acrylic yarns.
The sprayed members of the group of polymers known as polyacrylic are acrylic and methacrylic acids.
Methyl esters of acids easily polymerize in the presence of peroxide catalysts.
Acrylic acids are colorless and pungent-smelling acids that exist as liquids at microcosm temperature and pressure.
There are two commercially available grades of mating, the hard-to-use (94%) and the water-soluble resin (98% - 99.5%).
Acrylic Acid polymerizes easily when exposed to light, heat or metal.
Acrylic acid (IUPAC: prop-2-enoic acid) is an organic compound with the formula CH2 = CHCO2H.
Acrylic Acid is the simplest unsaturated carboxylic acid containing the vinyl group directly attached to the carboxylic acid terminus.
This colorless liquid has a characteristic acrid and sour odour.
Miscible with alcohols, ethers, water and chloroform.
More than one billion kilograms are produced annually.
Propene is obtained from acrylic acid, a by-product of gasoline and ethylene production.
Acrylic Acid Reactions and Uses:
When acrylic acid is reacted with alcohol; The carboxylic acid is subjected to typical reactions to form the ester.
Acrylic acid esters and salts are also known collectively as acrylates or propenoates.
Acrylic acid is the most common alkyl esters, methyl, butyl, ethyl and ethylhexyl acrylates.
Acrylic acid and its esters are used in various productions to form homopolymers or copolymers, by reacting them in double bonds to form polyacrylic acid or other monomers such as acrylamide, vinyl,
Acrylic Acid is combined with styrene and butadiene to produce plastics, adhesives, coatings, elastomers, as well as paints and floor varnishes.
Acrylic Acid Substituents:
The substituent acrylic acid may be present as a carboxyalkyl group as a continuation of the removal of an acyl group or molecular group.
Acrylic Acid Safety:
Acrylic acid is a very serious irritant to the skin and respiratory tract.
Eye contact is extremely inconvenient and can cause irreversible damage.
Acrylic acid (propenoic acid) ; Acrylic acid is an organic and strong acid.
They are colorless and sharp-smelling liquid acids at room conditions.
Usage areas
Acrylic acid is the starting material in the production of polymers.
They are used in the production of many materials such as plastics, coatings, adhesives, paint and varnish.
Acrylic acid is the raw material of weaving fiber.
Acrylic acid is used in the paper industry.
Optical instruments are used as the main raw material in jewelery making.
In industry, Acrylic acid is obtained by the reaction of acetylene and carbon monoxide with water in the presence of a nickel catalyst or by the hydrolysis of acrylonitrile compounds.
Acrylic acid is the starting material in the production of polymers.
Acrylic compounds Acrylic compounds are the raw material of various compounds such as molded building materials, optical instruments, jewellery, adhesives, coating materials and textile fibers.
For example, orlon and acrylan are the trade names of acrylic yarns, and plexiglass is the trade name of glass-like acrylic materials.
The main members of the family of polymers known as polyacrylic are acrylic and methacrylic acids.
The methyl esters of these acids easily polymerize in the presence of peroxide catalysts.
Acrylic acids are colorless and pungent-smelling acids that exist as liquids at room temperature and pressure.
There are 2 commercial grades, which are used for esterification (94%) and used to make water-soluble resins (98%-99.5%).
Acrylic acid polymerizes easily when exposed to light, heat or metal. Bi x indicator should always be present for polymerization.
Paint color appears in every aspect of our lives.
Today, its usage areas are expanding and its consumption is gradually increasing.
Acrylic acid is a chemical coating material that provides protection against external factors by forming a thin film layer on the surface on which the paint is applied, as well as giving the surface a decorative feature.
A paint formulation consists of a mixture of several materials.
Basically, there are four main elements in the structure of the paint.
These; binders, pigments, additives and solvents.
The usage rates of these materials vary for different types of paints.
Pigments are organic and inorganic substances that provide color, covering and protection to the paint.
Pigments are substances that are insoluble in any solution.
Those used to give color are called color pigments, those used for filling power and cost reduction are called fillers.
Fillers can make up 20-50% of paints.
These substances are used in paint formulations to control rheological properties, reduce gloss, increase mechanical properties, or improve the barrier properties of the paint film.
Titanium dioxide, iron oxide, zinc oxide, zinc phosphate are examples of commonly used pigments.
Titanium dioxide is the most common pigment used in paint.
Calcium and barium compounds, calcite, dolomite, gypsum, talc and limestone are examples of fillers.
Calcite is the most common filler used in paint.
Turkey's paint industry is Europe's 6th largest paint producer based on total production.
While the rate of imported raw materials is approximately 65%, Turkey's paint industry is dependent on foreign sources.
Considering the increase in production, foreign dependency in raw materials is increasing day by day.
The most common type of dispersion additive used for inorganic pigments in water-based paints is polyelectrolytes.
They are divided into inorganic and organic polyelectrolytes.
Examples of organic polyelectrolytes are polyacrylic acids (PAA) and acrylic-maleic anhydride P(AA-MA) copolymers.
Polyacrylic acids and their derivatives are used as thickening, dispersing, suspending and emulsifying agents in disposable diapers, ion exchange resins, coatings; It is used in the pharmaceutical, cosmetic and paint industries.
Acrylic acid and P(AA-MA) derivatives with molecular weights between 1,000 and 20,000 g/mol are the most commonly used dispersants in the paint industry.
These substances are neutralized with ammonium, sodium or potassium hydroxide to ensure their solubility in water.
The sodium salt of polyacrylic acid (NaPAA) is the most widely used dispersant agent in water-based paint formulations.
Acrylic acid is generally produced by free radical polymerization method.
Polymers with molecular weights from a few thousand to several hundred thousand can be obtained.
The molecular weights of PAAs, which are used as the most common dispersants in the paint industry, are between 1,000 and 20,000 g/mol.
The molecular weight can be controlled by adjusting the amount of initiator and chain transfer agent.
controlled radical polymerization; There are three different types: nitroxide-mediated polymerization (NMP), atom transfer radical polymerization (ATRP), and reversible addition-fragmentation chain transfer (RAFT).
In the production of acrylic acid by NMP polymerization, there is a problem of degradation of nitroxide in an acidic medium.
In the atom transfer radical polymerization of acrylic acid, metal attachment to the polymer cannot be controlled.
Therefore, the most suitable method to produce polyacrylic acid with low molecular weight and low PDI value is the reversible addition-fragmentation chain transfer (RAFT) method.
In this study, the stabilization of water-based paint formulations using NaPAA and acrylic-maleic anhydride copolymer sodium salt (NaP(AA-MA)) as dispersant was studied.
Acrylic acid was synthesized from the controlled radical polymerization of acrylic acid with the "Reversible addition-fragmentation chain transfer" method and from the controlled radical copolymerization of P(AA-MA), acrylic and maleic anhydride with the same method.
NaPAA and NaP(AA-MA) were obtained from neutralization of PAA and P(AA-MA) with sodium hydroxide (32% by weight).
NaPAA, to determine the most suitable polymerization parameters; It was synthesized in four different ways by varying the amount of chain transfer agent, changing the ratio of initiator and monomer, changing the feed time of monomer and initiator, and changing the amount of solvent.
In addition, AA/MA: 1:1 and AA/MA: 1:0.5 ratios were synthesized to determine the desired acrylic acid-maleic anhydride monomer ratio.
In addition, AA/MA: 0.5:1 ratio was tried to be synthesized, but the product crystallized due to the tendency of high amount of maleic anhydride to crystallize at room temperature.
The synthesized samples were structurally determined by FTIR.
The FTIR spectrum gave the expected peaks due to the chemical structure of PAA, NaPAA, P(AA-MA) and Na(AA-MA).
The solid contents of the synthesized polymers were determined with a rapid solids meter.
The Brookfield viscosities of the polymers were measured at 6 rpm at 20°C.
Molecular weight and molecular weight distributions were determined by 4-way RALS and GPC with LALS, RI, UV and viscometer detectors.
The amount of unpolymerized acrylic acid monomer in the synthesized PAAs was determined by HPLC.
The percent conversion of acrylic acid was calculated using the amount of unpolymerized acrylic acid monomer.
According to the percentage conversions of the calculated acrylic acid; As the amount of NaHyp used as the chain regulating agent and the solution used increase, the conversion increases.
When the APS/AA ratio is 5, 6 and 7.5%, over 94% monomer conversion can be obtained.
When the initiator feed time was increased from 4.5 hours to 5.5 hours, the monomer conversion remained almost the same, and the highest monomer conversion was achieved with 98.72% when the initiator feed time was 6.5 hours.
1H-NMR analyzes were performed to determine the acrylic acid and maleic anhydride monomer ratios of the synthesized NaP(AA-MA) copolymers.
Copolymer samples dried in microwave oven were dissolved in deutero water and given to NMR device.
Although the theoretical maleic anhydride monomer ratio of C1_Na copolymer is 33%, according to the 1H-NMR analysis results obtained; In the C1_Na copolymer with an AA/MA monomer ratio of 1:0.5, the ratio of maleic anhydride monomer is 23% and the acrylic acid monomer ratio is 77%.
In addition, although the theoretical maleic anhydride monomer ratio of the C2_Na copolymer, which is another synthesized copolymer, is 50%, according to the 1H-NMR analysis results; The ratio of maleic anhydride monomer is 38% and acrylic acid monomer ratio is 62% in the C2_Na copolymer with an AA/MA monomer ratio of 1:1.
The reason for this difference between the theoretical and actual monomer ratios is steric hindrance.
Maleic anhydride exhibits little tendency to copolymerization in aqueous media.
In the propagation step of the copolymerization, the monomer molecule is sterically hindered by the propagating radical group.
Thus, the propagation step of the copolymerization takes place extremely slowly.
To determine the dispersion efficiency, an aqueous mixture containing 5 micron calcium carbonate with a solid content of 66% was prepared.
Then, the aqueous mixture and the synthesized NaPAA or NaP(AA-MA) dispersing agents were placed in a dispersion container and mixed with a mechanical mixer at 2000 rpm for 20 minutes until a homogeneous mixture was formed.
To determine the dispersion efficiency of NaPAA polymers and NaP(AA-MA) copolymers, the viscosities of calcite slurries were measured with a Brookfield DV-II model viscometer at 20°C at 60 rpm.
Viscosities were recorded to form the slope containing varying amounts of NaPAA and NaP(AA-MA) dispersing agent versus viscosities of calcite slurries.
To examine the stabilization of calcite slurries with varying amounts of NaPAA or NaP(AA-MA) added as a dispersing agent, the zeta potential of the slurry was measured with a zeta potential meter.
Then, to examine the performances of water-based paint formulations, a sample water-based plastic paint formulation with a PVC value of 74 and prepared with NaPAA polymers or NaP(AA-MA) copolymers as dispersing agent was selected.
Grindometer measurements of paint formulations were performed to confirm the fineness of the dispersion and to detect oversized particles in the paint dispersion.
Paint films were applied to the covering cards.
In the next step; In order to calculate the opacity of the prepared paints, the light reflection intensities of the black and white areas of the cards were measured with a spectrophotometer.
In order to determine the dispersion and stabilization activities of the synthesized NaPAA polymers and NaP(AA-MA) copolymers in the paint, the initial viscosities of the paint formulations were measured with a Brookfield DV-II model viscometer.
The changes in the rheological stability of the prepared paint formulations over time and under temperature were determined by storing them for one month at 52±1°C and measuring Brookfield viscosities at 20°C, one week apart.
Measurement of storage viscosities explains that paint formulations improve dispersion efficiency as the molecular weight and molecular distribution of the polymeric dispersing agent decrease.
Sodium hypophosphite can be used as a chain modifier in a mixture of isopropyl alcohol and water to easily obtain NaPAA, which has a low molecular weight and a narrow molecular weight distribution.
In addition, the feed time of the monomer and initiator affects the molecular weight and molecular weight distribution of NaPAA.
As the feeding time increased, the molecular weight decreased and the molecular weight distribution narrowed.
In addition, NaP(AA-MA) with 1:0.5 AA/MA monomer ratio offers better storage stability performance when used as a dispersing agent instead of NaPAA in water-based paint formulations
Acrylic acid undergoes undesirable reactions during its manufacture to form higher molecular weight compounds.
Uncontrolled, these reactions can cause sludge deposits and loss of recovery.
Current industry standard inhibitor treatments are only partially effective, causing a unit to combat contamination issues.
Nalco Water technology addresses the limitations of standard inhibitors and offers acrylic acid manufacturers a more effective solution and competitive advantage.
Acrylic acid is produced from ethylene and propylene, a byproduct of gasoline production:
CH2=CHCH3 + 3⁄2 O2 → CH2=CHCO2H + H2O
Since propane is a significantly cheaper raw material than propylene, significant research work is being done to develop a process based on the one-step selective oxidation of propane to acrylic acid.
Carboxylation of ethylene to acrylic acid under the supercritical condition of carbon dioxide is thermodynamically feasible once an efficient catalyst has been developed.
Since acrylic acid and its esters have long been commercially valuable, many other methods have been developed, but most have been abandoned for economic or environmental reasons.
An early method was the hydrocarboxylation of acetylene ("Reppe chemistry"):
HCCH + CO + H2O → CH2=CHCO2H
This method requires nickel carbonyl and high carbon monoxide pressures.
It was once produced by the hydrolysis of acrylonitrile derived from propene via ammoxidation, but has been abandoned because it constitutes a method of cogeneration of ammonium derivatives.
Other now-abandoned precursors for acrylic acid include etenone and ethylene cyanohydrin.
The Dow Chemical Company and its partner OPX Biotechnologies are investigating the use of fermented sugar to produce 3-hydroxypropionic acid (3HP), an acrylic acid precursor.
The aim is to reduce greenhouse gas emissions.
Reactions and uses
Acrylic acid undergoes typical reactions of a carboxylic acid. When it reacts with an alcohol, it forms the corresponding ester.
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.
Acrylic acid and its esters combine easily with themselves (to form polyacrylic acid) or with other monomers (for example, acrylamides, acrylonitrile, vinyl compounds, styrene and butadiene) by reacting at their double bonds to form homopolymers or copolymers used in manufacturing.
various plastics, coatings, adhesives, elastomers, as well as floor varnishes and paints.
Acrylic acid is a compound used in many industries, such as the diaper industry, the water treatment industry, or the textile industry.
Acrylic acid is estimated that the worldwide consumption of acrylic acid will exceed an estimated 8,000 kilotonnes by 2020.
This increase is expected to result from the use of this product in new applications, including personal care products, detergents and products.
Used for adult incontinence.
Substitutions Substitution
Exclusively, acrylic acid may exist as an acyl group or a carboxyalkyl group depending on the removal of the group from the molecule.
More specifically, these are:
Acryloyl group by removal of -OH from carbon-1.
The 2-carboxytenyl group with the removal of a −H from carbon-3. This substituent group is found in chlorophyll.
Acrylic acid acts as a precursor in the production of 3-hydroxypropionic acid.
Acrylic acid is used in the preparation of water-absorbing resins.
Acrylic acid reacts with alcohols to prepare the corresponding esters.
Acrylic acids esters are used as raw materials for synthetic resins, rubbers, coating adhesives, water-based paints, floor varnishes and adhesives.
Acrylic acid is also used to form homopolymers or copolymers by reacting with other monomers such as acrylamides, acrylonitrile, vinyl, styrene and butadiene.
Acrylic Acid (propene acid) is a clear, colorless, corrosive and flammable liquid, acrid/sharp small and miscible with water, alcohol, ether, benzene, chloroform and acetone.
Acrylic acid is a versatile and valuable industrial chemical as it is a chemical intermediate used in the manufacture of many industrial and consumer products.
Miscible with alcohol, ether and many other organic solvents
Highly refractive, flammable, colorless liquid
Clear and colorless liquid, which finds widespread use thanks to its chemical structure that allows easier combination with large chain or polymer-forming compounds.
miscible with water
Acrylic acids are colorless and pungent-smelling acids that exist as liquids at room temperature and pressure.
Acrylic acid has 2 commercial grades, one used for esterification and one used to make water-soluble resins.
Acrylic acid polymerizes easily when exposed to light, heat or metal.
