Uses
Vinyl laurate can be used to synthesize the following:
- sucrose laurate esters from sucrose in organic solvents
- poly(vinyl laurate) (PVL)latexes
- porous conducting ‘‘soft′′ polymer foams which can be used as gas sensors
Uses
Vinyl laurate was used in the synthesis of laurate and stearate esters of corn starch. It was used as the acyl donor during synthesis of sucrose laurate esters catalyzed by
Bacillus pseudofirmus AL-89 . Vinyl laurate was also used in the preparation of chirally deuterated benzyl chlorides.
Preparation
A method for the preparation of vinyl laurate: In a 500-ml round-bottomed three-necked flask fitted with a thermometer, a reflux condenser and a gas inlet tube through which a stream of nitrogen is passed, place 206 g (2.4 moles) of freshly distilled vinyl acetate and 80 g (0.4 moles) of lauric acid. The lauric acid is dissolved by heating, and 1.6 g of mercuric acetate is added. The mixture is shaken by hand for approximately 30 minutes, and 0.15 ml of 100% sulphuric acid is added dropwise. The solution is heated under reflux for 3 hours, then 0.83 g of sodium acetate trihydrate is added to neutralise the sulphuric acid. The excess vinyl acetate is recovered by distillation at atmospheric pressure (vapour temperature approximately 70–80°C) until the pot temperature reaches 125°C. The distillation is completed at a pressure of 10 mm Hg or lower; after collecting a small amount of low-boiling-point material, redistillation yields 48–53 g (53–59%) of pure vinyl laurate.
General Description
Vinyl laurate is a clear, colorless to light yellow colored liquid. The flash point is 125°C. It forms aqueous colloidal microgel by copolymerization with
N-isopropylacrylamide. The enzymatic acylation of Avicel cellulose with vinyl laurate, a solvent free reaction system, was studied.
Safety
VINYL LAURATE (VL) is used as a monomer in the production of polyvinyl acetate-vinyl laurate copolymer (PVAcVL). This substance is a component of chewing gum base. Animal toxicity studies have shown that VL exhibits no mutagenicity and no signs of systemic toxicity. No adverse effects on reproductive performance or foetal development were observed. The No Observed Adverse Effect Level (NOAEL) for VL was determined to be 1000 mg/kg body weight/day, which corresponds to the highest dose level tested. Crucially, VL exhibits a high margin of safety, as this dose is approximately 3000 times the maximum typical chewing gum intake.
[1-2].
Synthesis
Add vinyl acetate, lauric acid and glacial acetic acid to the reaction vessel, and the mass ratio of vinyl acetate, lauric acid and glacial acetic acid is 1: (0.3-0.4): 0.05, and add concentrated sulfuric acid with a mass fraction of 95-98% under the stirring effect of 160-220 rpm, and the added amount of concentrated sulfuric acid is 0.002-0.0025 times the mass of vinyl acetate, and mix uniformly, to obtain The mixture; the mixture is warmed to 75-80 C., and reacted at 75-80 C. for 1-2 hours; after the reaction is finished, sodium acetate trihydrate 0.005-0.006 times the weight of the vinyl acetate is added to the reaction solution, and stirred under stirring at 160-220 rpm for 30-40 minutes, and then distilled under reduced pressure, to obtain said vinyl laurate.
References
[1] Horst Messinger, Albert B. (2014). Subchronic toxicity, toxicity to reproduction and prenatal developmental toxicity of vinyl laurate. Regulatory Toxicology and Pharmacology, 70 1, Pages 80-86. https://doi.org/
10.1016/j.yrtph.2014.06.015[2] Ben A.R. Lina , Albert B., Horst Messinger. (2015). 13-week oral toxicity study of vinyl laurate in rats. Regulatory Toxicology and Pharmacology, 71 1, Pages 101-107. https://doi.org/
10.1016/j.yrtph.2014.10.015
