The IUPAC name of Acrylic acid is Prop-2-enoic acid. It has the CAS register number of 79-10-7 and EINECS register number 201-177-9. Acrylic acid is an organic compound with the formula CH2=CHCO2H. It is miscible with water, alcohols, ethers, and chloroform, however, incompatible with strong oxidizing agents, strong bases, amines. It contacts with oxidizers may cause fire. Acrylic acid is a colorless liquid with a distinctive acrid odor. What's more, this chemical is unstable - may contain p-methoxyphenol as an inhibitor.
Physical properties about Acrylic acid are:
(1)ACD/LogP: 0.149; (2)ACD/LogD (pH 5.5): -1.12; (3)ACD/LogD (pH 7.4): -2.90; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.53; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.422; (12)Molar Refractivity: 17.237 cm3; (13)Molar Volume: 67.775 cm3; (14)Polarizability: 6.833 10-24cm3; (15)Surface Tension: 32.8899993896484 dyne/cm; (16)Density: 1.063 g/cm3; (17)Flash Point: 61.568 °C ; (18)Enthalpy of Vaporization: 41.721 kJ/mol; (19)Boiling Point: 140.999 °C at 760 mmHg; (20)Vapour Pressure: 3.42300009727478 mmHg at 25°C
Preparation of Acrylic acid:
Acrylic acid and acrylates were once prepared by reaction of acetylene and carbon monoxide with water or an alcohol, with nickel carbonyl as catalyst.
HC≡CH + CO + H2O → CH2=CHCO2H
In the presence of such catalysts as a solution of cuprous and ammo-nium chlorides, hydrogen cyanide adds to acetylene to give acrylonitrile (CH2=CHCN). However, this process has been replaced by processes involving ammoxidation of propylene. Similarly, the process for the manufacture of Acrylic acid has been superseded by processes involving oxidation of propylene although, for some countries, acetylene may still be used in acrylate manufacture. Thus, Acrylic acid is made by the oxidation of propylene to acrolein and further oxidation to acrylic acid.
2 CH2=CHCH3 + O2 → 2 CH2=CHCH=O
2 CH2=CHCHO + O2 → 2 CH2=CHCOOH
Another method for production of Acrylic acid is by the hydrolysis of acrylonitrile:
CH2=CH-CN + 2 H2O+H+ → CH2=CH-COOH + NH4+
Moreover, acrylonitrile hydrolyzes using sulfuric acid as the reagent to give sulfates of Acrylamide, and then the second hydrolysis to produce Acrylic acid, with byproduct ammonium bisulfate:
CH2=CHCN + H2O + H2SO4 → CH2=CHCONH2·H2SO4
CH2=CHCONH2·H2SO4 + H2O → CH2=CHCOOH + NH4HSO4
Uses of Acrylic acid:
Acrylic acid and its esters readily combine with themselves (to form polyacrylic acid) or other monomers 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. Acrylic acid can be used as tackiness agent, water thickener, coating agent of coated paper and also used in manufacture of polyacrylic acid salts. In addition, the substance is the important raw material in organic synthetic and preparation of resin monomer which is the vinyl monomers, the rate of polymerization is very fast.
Safety information of Acrylic acid:
When you are using Acrylic acid, you should be very cautious about it. The substance is corrosive, flammable and dangerous for the environment. In addition, Acrylic acid is harmful by inhalation, in contact with skin and if swallowed. It can cause severe burns. This chemical is very toxic to aquatic organisms. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact and use it, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Moreover, you must avoid release to the environment. When using it, you can refer to special instructions/safety data sheet.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C=CC(=O)O
(2)InChI: InChI=1S/C3H4O2/c1-2-3(4)5/h2H,1H2,(H,4,5)
(3)InChIKey: NIXOWILDQLNWCW-UHFFFAOYSA-N
Toxicity of Acrylic acid are as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
monkey | LC | inhalation | > 75ppm/6H (75ppm) | SENSE ORGANS AND SPECIAL SENSES: DEVIATED NASAL SEPTUM: OLFACTION SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION | Toxicologist. Vol. 36(1, Pg. pt2), 113. |
mouse | LC50 | inhalation | 5300mg/m3/2H (5300mg/m3) | | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 16, 1982. |
mouse | LD50 | intraperitoneal | 144mg/kg (144mg/kg) | | Yakugaku Zasshi. Journal of Pharmacy. Vol. 104, Pg. 793, 1984. |
mouse | LD50 | oral | 2400mg/kg (2400mg/kg) | | Biochemical Journal. Vol. 34, Pg. 1196, 1940. |
mouse | LD50 | subcutaneous | 1590mg/kg (1590mg/kg) | | Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969. |
mouse | LD50 | unreported | 830mg/kg (830mg/kg) | | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(10), Pg. 64, 1984. |
rabbit | LD50 | skin | 280uL/kg (0.28mL/kg) | | Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974. |
rabbit | LD50 | unreported | 250mg/kg (250mg/kg) | | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(10), Pg. 64, 1984. |
rat | LCLo | inhalation | 4000ppm/4H (4000ppm) | | Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974. |
rat | LD50 | intraperitoneal | 22mg/kg (22mg/kg) | | Journal of Dental Research. Vol. 51, Pg. 1632, 1972. |
rat | LD50 | oral | 33500ug/kg (33.5mg/kg) | | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 16, 1982. |
rat | LD50 | unreported | 1250mg/kg (1250mg/kg) | | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(10), Pg. 64, 1984. |