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79-20-9

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Identification

Name
Methyl acetate
CAS
79-20-9
Synonyms
ACETIC ACID METHYL ESTER
FEMA 2676
LABOTEST-BB LT00785639
METHYL ACETATE
RARECHEM AL BF 0544
Acetate de methyle
acetatedemethyle
acetatedemethyle(french)
CH3COOCH3
Devoton
ethanoicacid,methylester
Ethyl ester of monoacetic acid
ethylesterofmonoaceticacid
femanumber2676
Methyl acetic ester
Methyl ester of acetic acid
Methyl ethanoate
Methylacetaat
Methylacetat
methylaceticester
EINECS(EC#)
201-185-2
Molecular Formula
C3H6O2
MDL Number
MFCD00008711
Molecular Weight
74.08
MOL File
79-20-9.mol

Chemical Properties

Appearance
colourless liquid with a pleasant odour
Appearance
Methyl acetate is a colorless liquid with a fruity odor.
mp 
-98 °C
Melting point 
-98 °C (lit.)
Boiling point 
57-58 °C (lit.)
bp 
57-58 °C(lit.)

density 
0.932 g/mL at 25 °C(lit.)

vapor density 
2.55 (vs air)

vapor pressure 
165 mm Hg ( 20 °C)

FEMA 
2676
refractive index 
n20/D 1.361(lit.)

Fp 
3.2 °F

storage temp. 
Flammables area
solubility 
250g/l
form 
Solution
color 
Clear colorless to slightly pale yellow
Odor
Slightly acrid, sweet; fragrant.
Stability:
Stable. Extremely flammable-readily forms explosive mixtures with air. Note low flash point and wide explosion limits. Incompatible with strong oxidizing agents, strong bases, strong acids, nitrates. May be moisture sensitive.
Relative polarity
0.253
Odor Threshold
1.7ppm
explosive limit
3.1-16%(V)
Water Solubility 
250 g/L (20 ºC)
λmax
λ: 255 nm Amax: 1.0
λ: 275 nm Amax: 0.1
λ: 300 nm Amax: 0.01
JECFA Number
125
Merck 
14,6008
BRN 
1736662
Henry's Law Constant
0.90 at 20.00 °C, 1.56 at 30.00 °C (headspace-GC, Hovorka et al., 2002)
Exposure limits
TLV-TWA 200 ppm (~610 mg/m3) (ACGIH, MSHA, and OSHA); TLV-STEL 250 ppm (~760 mg/m3) (ACGIH); IDLH 10,000 ppm (NIOSH).
CAS DataBase Reference
79-20-9(CAS DataBase Reference)
NIST Chemistry Reference
Acetic acid, methyl ester(79-20-9)
EPA Substance Registry System
79-20-9(EPA Substance)

Safety Data

Hazard Codes 
F,Xi
Risk Statements 
R11:Highly Flammable.
R36:Irritating to the eyes.
R66:Repeated exposure may cause skin dryness or cracking.
R67:Vapors may cause drowsiness and dizziness.
Safety Statements 
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S29:Do not empty into drains .
S33:Take precautionary measures against static discharges .
RIDADR 
UN 1231 3/PG 2

WGK Germany 
1

RTECS 
AI9100000

Autoignition Temperature
936 °F
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29153900
Safety Profile
Moderately toxic by several routes. A human systemic irritant by inhalation. A moderate skin and eye irritant. Mutation data reported. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Moderate explosion hazard when exposed to heat or flame. When heated to decomposition it emits acrid smoke and fumes. See also ESTERS.
Hazardous Substances Data
79-20-9(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rat > 2000 mg/kg

Raw materials And Preparation Products

Hazard Information

General Description
A clear colorless liquid with a fragrant odor. Moderately toxic. Flash point 14°F. Vapors heavier than air.
Reactivity Profile
METHYL ACETATE(79-20-9) presents a fire or explosion hazard when exposed to strong oxidizing agents. Emits irritating fumes and acrid smoke when heated to decomposition, [Lewis, 3rd ed., 1993, p. 826]. METHYL ACETATE(79-20-9) reactivity is consistent with other compounds of the ester group.
Air & Water Reactions
Highly flammable. Water soluble.
Hazard
Flammable, dangerous fire and explosion risk, explosive limits in air 3–16%. Irritant to respiratory tract. Headache, dizziness, nausea, eye damage (degeneration of ganglion cells in the retina).
Health Hazard
(Very similar to those of methyl alcohol, which constitutes 20% of commercial grade.) Inhalation causes headache, fatigue, and drowsiness; high concentrations can produce central nervous system depression and optic nerve damage. Liquid irritates eyes and may cause defatting and cracking of skin. Ingestion causes headache, dizziness, drowsiness, fatigue; may cause severe eye damage.
Potential Exposure
Methyl acetate is used as a solvent in lacquers and paint removers; and as an intermediate in pharmaceutical manufacture.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
Fire Hazard
Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back.
Shipping
UN1231 Methyl acetate, Hazard Class: 3; Labels: 3-Flammable liquid.
Incompatibilities
Vapor may form explosive mixture with air. A Strong reducing agent. Incompatible water, acids, nitrates, strong oxidizers; alkalis. Attacks some plastics. Attacks many metals in presence of water. Reacts slowly with water, forming acetic acid and methanol. Decomposes in heat; on contact with air, bases, strong oxidizers; UV-light; possible fire and explosion hazard
Description
Methyl acetate, also known as MeOAc , acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is VOC exempt.
Chemical Properties
Methyl acetate has a pleasant, fruity odor and slightly bitter flavor.
Chemical Properties
Methyl acetate has a pleasant, fruity odor and slightly bitter flavor. May be prepared by boiling acetic acid and methanol in the presence of acid catalysts; or by heating methanol with an excess carbon monoxide under pressure in the presence of a catalyst (phosphoric acid, cobalt salts).
Methyl acetate occurs naturally in low concentrations in mint, fungus,grapes, banana, coffee (Furia and Bellanca, 1975) and is a volatile constituent of nectarines (Takeoka et al., 1988). It is also present in some distilled alcoholic beverages (Shimoda et al., 1993). It is produced industrially via the carbonylation of methanol as a byproduct of acetic acid production or by esterification of acetic acid with methanol in the presence of strong acid such as sulfuric acid.
Waste Disposal
Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
Physical properties
Colorless liquid with a pleasant odor. An odor threshold concentration of 48 ppbv was reported by Nagata and Takeuchi (1990). Cometto-Mu?iz and Cain (1991) reported an average nasal pungency threshold concentration of 112,500 ppmv.
Occurrence
Reported found in apple, banana, sweet and sour cherry, tangerine juice, black currants, guava, grapes, melon, peach, pear, pineapple, strawberry, cabbage, tomato, clove bud, peppermint oil, vinegar, bread, cheeses, butter, yogurt, beef, beer, cognac, rum, whiskies, cider, sherry, grape wines, cocoa, coffee, filbert, peanut, honey, soybean, olive, passion fruit, fruit brandies, fig, gin, kiwifruit, clary sage, arrack and nectarine.
Uses
Solvent for lacquers, oils, and resins
Uses
Solvent for nitrocellulose, acetylcellulose, and many resins and oils; manufacture of artificial leather.
Uses
Methyl acetate is used as a solvent forlacquers, resins, oils, and nitrocellulose; inpaint removers; as a flavoring agent; and inthe manufacture of artificial leather.
Preparation
Methyl acetate is produced industrially via the carbonylation of methanol as a byproduct of the production of acetic acid.Methyl acetate also arises by esterification of acetic acid with methanol in the presence of strong acids such as sulfuric acid, this production process is famous because of Eastman Kodak's intensified process using a reactive distillation.
2–1-Reactions
In the presence of strong bases such as sodium hydroxide or strong acids such as hydrochloric acid or sulfuric acid it is hydrolyzed back into methanol and acetic acid, especially at elevated temperature. The conversion of methyl acetate back into its components, by an acid , is a first-order reaction with respect to the ester. The reaction of methyl acetate and a base, for example sodium hydroxide, is a second-order reaction with respect to both reactants.
3-Applications
A major use of methyl acetate is as a volatile low toxicity solvent in glues, paints, and nail polish removers. Acetic anhydride is produced by carbonylation of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis.
Aroma threshold values
Detection: 1.5 to 47 ppm
Taste threshold values
Taste characteristics at 60 ppm: green, ethereal, fruity, fresh, rum and whiskey-like.
Chemical Reactivity
Reactivity with Water Reacts slowly to form acetic acid and methyl alcohol; the reaction is not violent; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Chemical Synthesis
By boiling acetic acid and methanol in the presence of acid catalysts, or by heating methanol with an excess of carbon monoxide under pressure in the presence of a catalyst (phosphoric acid, cobalt salts).
Environmental Fate
Photolytic. A rate constant of 2.00 x 10-13 cm3/molecule?sec was reported for the reaction of methyl acetate and OH radicals in aqueous solution (Wallington et al., 1988b).
Chemical/Physical. Slowly hydrolyzes in water yielding methyl alcohol and acetic acid (NIOSH, 1997). The estimated hydrolysis half-life in water at 25 °C and pH 7 is 2.5 yr (Mabey and Mill, 1978).
At an influent concentration of 1,030 mg/L, treatment with GAC resulted in an effluent concentration of 760 mg/L. The adsorbability of the carbon used was 54 mg/g carbon (Guisti et al., 1974).
Purification Methods
Methanol in methyl acetate can be detected by measuring its solubility in water. At 20o, the solubility of methyl acetate in water is ca 35g per 100mL, but 1% MeOH confers complete miscibility. Methanol can be removed by conversion to methyl acetate, by refluxing for 6hours with acetic anhydride (85mL/L), followed by fractional distillation. Acidic impurities can be removed by shaking with anhydrous K2CO3 and distilling. An alternative treatment is with acetyl chloride, followed by washing with concentrated NaCl and drying with CaO or MgSO4. (Solid CaCl2 cannot be used because it forms a crystalline addition compound.) Distillation from copper stearate destroys peroxides. Free alcohol or acid can be eliminated from methyl acetate by shaking with strong aqueous Na2CO3 or K2CO3 (three times), then with aqueous 50% CaCl2 (three times), saturated aqueous NaCl (twice), drying with K2CO3 and distilling it from P2O5. [Beilstein 2 IV 122.]

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