540-88-5 Usage
Chemical Properties
tert-Butyl acetate or t-butyl acetate is a colorless flammable liquid with a camphoror
blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks,
adhesives, thinners, and industrial cleaners. It is also used as an additive to improve the
antiknock properties of motor fuels. tert-Butyl acetate has three isomers: n-butyl acetate,
isobutyl acetate, and sec-butyl acetate.
Physical properties
Colorless liquid with a fruity odor. Odor threshold concentration in water is 4 ppm (CHRIS,
1994). Nagata and Takeuchi (1990) reported an odor threshold concentration of 71 ppbv.
Uses
tert-Butyl acetate is common industrial solvent used in the making of lacquers, artificial leather, airplane dope, perfume, and as a food additive.
Production Methods
tert-Butyl acetate is prepared from isobutylene reacting with
acetic acid in the liquid phase with vanadium pentoxideimpregnated
silica as the catalyst and with heat to increase
the yield .
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 3, p. 142, 1955Synthesis, p. 1015, 1987Tetrahedron Letters, 37, p. 4555, 1996 DOI: 10.1016/0040-4039(96)00902-1
General Description
Tert-butyl acetate is a colorless liquid with a mild odor. Floats on water. Produces irritating vapor. (USCG, 1999)
Air & Water Reactions
Highly flammable. Insoluble in water.
Reactivity Profile
tert-Butyl acetate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. tert-Butyl acetate is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids .
Hazard
Flammable, moderate fire risk. Eye and
upper respiratory tract irritant.
Health Hazard
Exposure to tert-butyl acetate causes eye, skin, and respiratory irritation in workers. By
analogy with the effects of exposure to similar esters, tert-butyl acetate may act as a CNS
depressant at high concentrations. The signs and symptoms of acute exposure to tert-butyl
acetate include, but are not limited to, itchy or inflamed eyes and irritation of the nose and
upper respiratory tract. Exposures to tert-butyl acetate at high concentrations may cause
headache, drowsiness, and other narcotic effects.
Safety Profile
Poison by inhalation
and ingestion. Flammable. To fight fire, use
alcohol foam, CO2, dry chemical. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Environmental fate
Chemical/Physical. Hydrolyzes in water to tert-butyl alcohol and acetic acid. The estimated
hydrolysis half-life at 25 °C and pH 7 is 140 yr (Mabey and Mill, 1978).
storage
tert-Butyl acetate should be stored in a cool, dry, well-ventilated area in tightly sealed
containers that are labeled in accordance with regulatory standards. Containers of tert butyl acetate should be protected from physical damage and should be stored separately
from nitrates, strong oxidizers, strong acids, strong alkalis, heat, sparks, and open flame.
Because containers that formerly contained tert-butyl acetate may still hold product resi dues, they should be handled appropriately
Purification Methods
Wash the ester with 5% Na2CO3 solution, then saturated aqueous CaCl2, dry with CaSO4 and distil it. [McClosky et al. Org Synth Coll Vol IV 263 1963, Mangia et al. Org Prep Proc Int 18 13 1986, Beilstein 2 IV 151.]
Precautions
If exposures to tert-butyl acetate or a solution in work areas gets into the eyes, immediately
fl ush the eyes with large amounts of water for a minimum of 15 min, lifting the lower and
upper lids occasionally. Always use safety goggles or eye protection in combination with
breathing protection.
Check Digit Verification of cas no
The CAS Registry Mumber 540-88-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 540-88:
(5*5)+(4*4)+(3*0)+(2*8)+(1*8)=65
65 % 10 = 5
So 540-88-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O2/c1-5(7)8-6(2,3)4/h1-4H3
540-88-5Relevant articles and documents
Esterification of tert-butanol and acetic acid by silicotungestic acid catalyst supported on bentonite
Jin, Jian-Zhong,Sun, Na-Bo
, p. 4441 - 4443 (2013)
A series of solid acid catalysts were synthesized by incipient wetness impregnation method by varying the wt % of silicotungstic acid on bentonite. Silicotungestic acid supported on bentonite was used to catalytic synthesis of tert-butyl acetate with acetic acid and tert-butyl alcohol. The main reaction parameters such as silicotungstic acid loading on bentonite, the amount of catalyst, molar ratio of reactants, reaction temperature and reaction time have been investigated. The optimum conditions were determined as follows: silicotungstic acid loading on bentonite 25 wt %, catalyst 0.7 g, mole ratio of tert-butanol to acetic acid 1:1.1, reaction temperature 110 °C and reaction time 2 h. The esterification yield of tert-butyl acetate was about 87.2 %. The catalyst could be used repeatedly for many times without distinct loss in activity.
Dehydrogenative ester synthesis from enol ethers and water with a ruthenium complex catalyzing two reactions in synergy
Ben-David, Yehoshoa,Diskin-Posner, Yael,Kar, Sayan,Luo, Jie,Milstein, David,Rauch, Michael
supporting information, p. 1481 - 1487 (2022/03/07)
We report the dehydrogenative synthesis of esters from enol ethers using water as the formal oxidant, catalyzed by a newly developed ruthenium acridine-based PNP(Ph)-type complex. Mechanistic experiments and density functional theory (DFT) studies suggest that an inner-sphere stepwise coupled reaction pathway is operational instead of a more intuitive outer-sphere tandem hydration-dehydrogenation pathway.
Molybdenum-modified mesoporous SiO2as an efficient Lewis acid catalyst for the acetylation of alcohols
Hlatshwayo, Xolani S.,Ndolomingo, Matumuene Joe,Bingwa, Ndzondelelo,Meijboom, Reinout
, p. 16468 - 16477 (2021/05/19)
A suitable, expeditious and well-organized approach for the acetylation of alcohols with acetic anhydride in the presence of 5%MoO3-SiO2 as an optimum environmentally benign heterogeneous catalyst was developed. The high surface area obtained for 5%MoO3-SiO2, 101 m2 g-1 compared to other catalysts, 22, 23, and 44 m2 g-1 for 5%WO3-ZrO2, 5%WO3-SiO2, and 5%MoO3-ZrO2, respectively, appears to be the driving force for better catalytic activity. Amongst the two dopants used, molybdenum oxide is the better dopant compared to its tungsten oxide counterpart. High yields of up to 86% were obtained with MoO3 doping while WO3 containing catalysts did not show any activity. Other reaction parameters such as reactor stirring speed, and solvent variation were studied and revealed that the optimum stirring speed is 400 rpm and cyclohexane is the best solvent. Thus, the utilization of affordable and nontoxic materials, short reaction times, reusability, and producibility of excellent yields of the desired products are the advantages of this procedure.
Scalable green approach toward fragrant acetates
Puchl'Ová, Eva,Szolcsányi, Peter
, (2020/08/07)
The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.
