| Identification | More | [Name]
VINYL LAURATE | [CAS]
2146-71-6 | [Synonyms]
LAURIC ACID VINYL ESTER
VINYL LAURATE
Dodecanoicacid,ethenylester
VINYL LAURATE, WACKER QUALITY
vl
Vinyl dodecanoate
Vinyl Laurate (stabilized with MEHQ)
Dodecanoic acid vinyl ester
Lauric acid vinyl | [EINECS(EC#)]
218-414-7 | [Molecular Formula]
C14H26O2 | [MDL Number]
MFCD00048421 | [Molecular Weight]
226.36 | [MOL File]
2146-71-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
7℃ | [Boiling point ]
254 °C/1013 hPa (lit.) | [density ]
0.871 g/mL at 20 °C(lit.)
| [vapor pressure ]
0.28Pa at 24.85℃ | [refractive index ]
n20/D 1.441
| [Fp ]
136 °C | [solubility ]
H2O: slightly soluble1g/L at 20°C | [form ]
clear liquid | [color ]
Colorless to Light yellow | [Water Solubility ]
H2O: slightly soluble 1g/L at20°C | [BRN ]
1778369 | [InChI]
1S/C14H26O2/c1-3-5-6-7-8-9-10-11-12-13-14(15)16-4-2/h4H,2-3,5-13H2,1H3 | [InChIKey]
GLVVKKSPKXTQRB-UHFFFAOYSA-N | [SMILES]
CCCCCCCCCCCC(=O)OC=C | [LogP]
5.92 at 20℃ | [CAS DataBase Reference]
2146-71-6(CAS DataBase Reference) | [EPA Substance Registry System]
Dodecanoic acid, ethenyl ester (2146-71-6) |
| Safety Data | Back Directory | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HS Code ]
29159000 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [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 stir | [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
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