Acrylic acid

Base Information

• Chemical Name: Acrylic acid
• CAS No.: 79-10-7
• Deprecated CAS: 55927-87-2,1265528-53-7,1453489-99-0,1644624-02-1,166941-59-9,1703019-10-6,1873349-31-5,2015239-27-5,211862-52-1,2133361-51-8,1265528-53-7,1453489-99-0,1644624-02-1,166941-59-9,1703019-10-6,1873349-31-5,2015239-27-5,211862-52-1
• Molecular Formula: C3H4O2
• Molecular Weight: 72.0636
• Hs Code.: 2916110000
• European Community (EC) Number: 201-177-9,616-286-0
• ICSC Number: 0688
• NSC Number: 165257,114472,112123,112122,106037,106036,106035,106034,226569,4765
• UN Number: 2218
• UNII: J94PBK7X8S
• DSSTox Substance ID: DTXSID0039229
• Nikkaji Number: J1.493A
• Wikipedia: Acrylic_acid
• Wikidata: Q324628
• RXCUI: 1368626
• Metabolomics Workbench ID: 615
• ChEMBL ID: CHEMBL1213529
• Mol file: 79-10-7.mol

Synonyms:2-propenoic acid;acrylate;acrylic acid;acrylic acid, aluminum salt;acrylic acid, ammonium salt;acrylic acid, Ca (2:1) salt;acrylic acid, Ca (2:1) salt, dihydrate;acrylic acid, cobalt (2+) salt;acrylic acid, Fe (3+) salt;acrylic acid, magnesium salt;acrylic acid, potassium salt;acrylic acid, silver salt;acrylic acid, sodium salt;acrylic acid, zinc salt;Hystoacril;magnesium acrylate;vinylformic acid

Chemical Property of Acrylic acid

Chemical Property:

• Appearance/Colour: clear, colorless liquid
• Melting Point: 14 °C, 287 K, 57 °F
• Refractive Index: 1.4192-1.4212
• Boiling Point: 141 °C, 414 K, 286 °F
• PKA: 4.25±0.10(Predicted)
• Flash Point: 68 °C (154 °F)
• PSA: 37.30000
• Density: 1.051 g/cm³
• LogP: 0.25700
• Water Solubility.: MISCIBLE
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 72.021129366
• Heavy Atom Count: 5
• Complexity: 55.9

Purity/Quality:

99.5% , ^*data from raw suppliers

Safty Information:

• Pictogram(s): C, N
• Hazard Codes: C:Corrosive;;
• Statements: R10:; R20/21/22:; R35:; R50:
• Safety Statements: S26:; S36/37/39:; S45:; S61:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C=CC(=O)O
• Recent EU Clinical Trials: A randomized, double-blind, monocentric phase IV clinical study on the ocular tolerability of a topical ophthalmic product containing Retinolpalmitat 1000 I.U. in comparison to a reference product containing Carbomer 0.2 % with repeated ocular applications over 12 months in 120 patients with keratoconjunctivitis sicca
• Inhalation Risk: A harmful contamination of the air can be reached rather quickly on evaporation of this substance at 20 °C , on spraying or dispersing much faster.
• Effects of Short Term Exposure: The substance is corrosive to the eyes and skin. Corrosive on ingestion. The vapour is severely irritating to the eyes and respiratory tract.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the upper respiratory tract and lungs. This may result in reduced lung function and hyperreactivity of the airways.
• Chemical Composition and Structure: Acrylic acid, also known as propenoic acid, has the chemical formula CH2=CHCOOH. It contains a vinyl group (-CH=CH2) and a carboxylic acid group (-COOH) in its structure.
• Uses: Polymerization:; Acrylic acid is a key monomer used in the production of various polymers and copolymers, including poly(acrylic acid) and its salts, which are employed in superabsorbent materials, detergents, water treatment, and dispersants.; Chemical Reactions:; Acrylic acid's active chemical properties make it versatile for various chemical reactions. It can polymerize readily in air and undergo reactions such as hydrogenation to propionic acid and addition with hydrogen chloride to form 2-chloropropionic acid, used in acrylic resin production.; Industrial Applications:; Acrylic acid and its esters find applications in emulsion and solution polymers for coatings, adhesives, textiles, and other industrial products due to their resistance to chemical and environmental degradation and attractive strength properties.
• Mechanism of Action: In polymerization reactions, it readily undergoes free-radical polymerization to form polymers with desirable properties. In chemical reactions, it can act as both an electrophilic and nucleophilic agent, participating in addition and substitution reactions.
• Production Methods: Acrylic acid is primarily produced by catalytic oxidation of propylene, although alternative methods such as acetylene carbonylation and hydrolysis of cyanoethanol have been developed. The propylene oxidation method has become the main industrial method due to improvements in catalysts and processes.
• History and Development: Acrylic acid was first discovered in 1843 through the oxidation of acrolein. Industrial production methods were developed in the early 20th century, with significant advancements such as the acetylene carbonylation method by W.J. Reppe in 1939 and the propylene oxidation method in 1969. Acrylic acid is listed as a Category 3 carcinogen by the World Health Organization's International Agency for Research on Cancer (IARC).
• Market Data: The price of acrylic acid ranges from US$600 to US$1,200 per ton.

Technology Process of Acrylic acid

There total 550 articles about Acrylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 31.0%

ethene (74-85-1) + Cinnamic acid (621-82-9) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + stilbene (588-59-0) + acrylic acid (79-10-7)

Guidance literature:

Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 40 ℃; for 24h; under 562.556 Torr; Product distribution / selectivity; Inert atmosphere;

Reference yield: 13.0%

1-butylene (106-98-9,9003-28-5) + Cinnamic acid (621-82-9) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + acrylic acid (79-10-7)

Guidance literature:

Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 40 ℃; for 24h; under 750.075 Torr; Inert atmosphere;

Reference yield:

p-nitrophenyl acrylate (2123-85-5) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + acrylic acid (79-10-7)

Guidance literature:

With water; at 24 ℃; Kinetics; different pH;

upstream raw materials:

oxirane

hydrogen cyanide

maleic anhydride

3-Bromopropionic acid

Downstream raw materials:

2-hydroxyethyl acrylate

3-[(2-nitrophenyl)thio]propanoic acid

2-carboxyethyl acrylate

4-Nitro-3,5-dimethyl-1-(2-carboxyethyl)-pyrazol

Refernces

• 1、 Cui, Long,Yang, Xiangui,Zeng, Yi,Chen, Yuntang,Wang, Gongying. "A unique nickel-base nitrogen-oxygen bidentate ligand catalyst for carbonylation of acetylene to acrylic acid". . p. 57 - 61. Retrieved 2019.
• 2、 Jones, Christopher W.,Lopez-Castillo, Alejandro,Martins, Leandro,Vieira, Luiz H.. "Exploring the multifunctionality and accessibility of vanadosilicates to produce acrylic acid in one-pot glycerol oxydehydration". . . Retrieved 2020.
• 3、 Deng, Luyao,Fan, Yaoxin,Li, Shuangming,Liu, Yongwei,Lu, Zixuan,Yan, Yunong,Yu, Sansan,Zhang, Zhe. "Facile sub-/supercritical water synthesis of nanoflake MoVTeNbO:X-mixed metal oxides without post-heat treatment and their catalytic performance". . p. 39922 - 39930. Retrieved 2020.
• 4、 Frederick, Clay B.,Udinsky, John R.,Finch, Lavorgie. "The regional hydrolysis of ethyl acrylate to acrylic acid in the rat nasal cavity". . p. 49 - 56. Retrieved 1994.
• 5、 Desai,Halligudi,Nandibewoor. "Kinetics of osmium(VIII) catalyzed oxidation of allyl alcohol by potassium bromate in aqueous acidic medium-autocatalysis in catalysis". . p. 583 - 589. Retrieved 1999.
• 6、 Rasteiro, Letícia F.,Vieira, Luiz H.,Santilli, Celso V.,Martins, Leandro. "Surfactant-assisted synthesis of Mo-V mixed oxide catalysts for upgraded one-step conversion of glycerol to acrylic acid". . p. 11975 - 11982. Retrieved 2018.
• 7、 Sharma, Sangita,Ramani, Jayesh,Bhalodia, Jasmin,Vyas, Bijal. "Kinetic study of specific base catalyzed hydrolysis of ethyl acrylate in water-ethanol binary system". . p. 730 - 736. Retrieved 2013.
• 8、 Wang, Jibo,Ji, Baofeng,Chu, Wenling,Zhan, Shijing,Lin, Liwu,Yang, Weishen. "Bi4Cu0.2V1.8O11-δ based electrolyte membrane reactor for selective oxidation of propane to acrylic acid". . p. 157 - 162. Retrieved 2010.
• 9、 Possato, Luiz G.,Chaves, Thiago F.,Cassinelli, Wellington H.,Pulcinelli, Sandra H.,Santilli, Celso V.,Martins, Leandro. "The multiple benefits of glycerol conversion to acrolein and acrylic acid catalyzed by vanadium oxides supported on micro-mesoporous MFI zeolites". . p. 20 - 28. Retrieved 2017.
• 10、 Nagengast, Jens,Hahn, Simon,Taccardi, Nicola,Kehrer, Matthias,Kadar, Julian,Collias, Dimitris,Dziezok, Peter,Wasserscheid, Peter,Albert, Jakob. "Highly Selective Synthesis of Acrylic Acid from Lactide in the Liquid Phase". . p. 2936 - 2943. Retrieved 2018.