n-Butyl acrylate

Butyl acrylate, also known as 2-Propenoic acid, butyl ester, clear colorless, flammable liquid with a sharp characteristic odor. It is soluble in alcohol, ether, acetone and other organic solvents, but almost insoluble in water. What's more, n-butyl acrylate is incompatible with strong oxidizing agents, strong acids, strong bases. It can be polymerized into polymer and copolymer used in industry. 

Butyl acrylate reacts exothermically with acids to liberate heat along with alcohols and acids. Reacts with strong oxidizing agents, perhaps sufficiently exothermically to ignite the reaction products. Mixing with basic solutions generates heat. Generates flammable hydrogen with alkali metals and hydrides. Attacks many plastics [Handling Chemicals Safely 1980. p. 233]. Polymerizes readily, generating much heat in a reaction that is favored by heat and light [Handling Chemicals Safely 1980. p. 235].

Other properties of Butyl acrylate are: (1)ACD/LogP: 2.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.39; (4)ACD/LogD (pH 7.4): 2.39; (5)ACD/BCF (pH 5.5): 38.41; (6)ACD/BCF (pH 7.4): 38.41; (7)ACD/KOC (pH 5.5): 473.96; (8)ACD/KOC (pH 7.4): 473.96; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 26.3 Å²; (13)Index of Refraction: 1.418; (14)Molar Refractivity: 35.97 cm³; (15)Molar Volume: 142.6 cm³; (16)Polarizability: 14.26×10^-24 cm³; (17)Surface Tension: 26.7 dyne/cm; (18)Density: 0.898 g/cm³; (19)Flash Point: 39.4 °C; (20)Enthalpy of Vaporization: 38.29 kJ/mol; (21)Boiling Point: 145.9 °C at 760 mmHg; (22)Vapour Pressure: 4.75 mmHg at 25°C.

Preparation of Butyl acrylate: The production methods of acrylate are from acrylonitrile hydrolysis, β-propiolactone, Reppe method and improved Reppe method, cyanoethanol and the direct oxidation of propylene.
1. From cyanoethanol: The reaction of chloroethanol and sodium cyanide generates cyanoethanol which can hydrolyze to produce acrylic in the presence of sulfuric acid.
2. From acrylonitrile hydrolysis: As a rich source of acrylonitrile, this method to produce acrylate has been developed. Now, the industrialized methods contains Societe Ugine and Standard Oil Co (O-hio). Heat acrylonitrile and sulfuric acid to 90 °C to make acrylonitrile be hydrolyzed into acrylamide sulfate. The further esterification of this sulfate produces acrylate. Recently, it has been reported that when use acrylonitrile as raw material from one-step production, the yield of ether is 95%.
3. From β-propiolactone: Use acetic acid or acetone as raw materials, phosphate ester as catalyst to generate ethenone by pyrolysis at 625-730 °C. And then react with anhydrous methyl ester in the presence of AICI₃ or BF₃ catalyst to produce β-propiolactone by gas reaction at 25 °C. If the end product is acrylic, the propiolactone contacts with hot 100% phosphoric acid to obtain acrylic. If the end product is acrylate, the crude propiolactone may not go through purification, but directly reacts with the corresponding alcohol and sulfuric acid.

Uses of Butyl acrylate: Acrylic acid and its esters are widely used in industry. In use, it tends to aggregate acrylate into polymers or copolymers. Butyl acrylate (as well as methyl esterl, ethyl ester, 2-ethylhexoate) belongs to the soft monomer, which can copolymerize, crosslink and stem graft with a variety of hard monomers such as methyl methacrylate, styrene, acrylonitrile, vinyl acetate, and functional monomers such as HEMA, HpAA, glycidyl ester to produce a variety of 200-700 acrylic resin products. These products are widely used as coatings, adhesives, modified acrylic fibers, plastics modification, fiber and fabric processing, paper processing agents, leather processing, acrylic rubber, etc.

Safty of Butyl acrylate: Butyl acrylate is harmful by inhalation, in contact with skin and if swallowed. It is also irritating to eyes, respiratory system and skin. If you want to contact this product, you must wear suitable gloves and avoid contact with eyes. Moreover, it is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. You should avoid release to the environment. Refer to special instructions / safety data sheets.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(OCCCC)\C=C;
(2)Std. InChI:InChI=1S/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H,2-3,5-6H2,1H3;
(3)Std. InChIKey:CQEYYJKEWSMYFG-UHFFFAOYSA-N;

The toxicity data of Butyl acrylate as follows: