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Acetic anhydride

Description References
Acetic anhydride
Acetic anhydride structure
CAS No.
108-24-7
Chemical Name:
Acetic anhydride
Synonyms
AC2O;acetic;(CH3CO)2O;acetylether;Acetyl ether;ACETYL OXIDE;ACETIC OXIDE;Acetanhydrid;Acetanhydride;Acetyl acetate
CBNumber:
CB2852742
Molecular Formula:
C4H6O3
Formula Weight:
102.08864
MOL File:
108-24-7.mol

Acetic anhydride Properties

Melting point:
-73.1 °C
Boiling point:
140 °C
Density 
1.087
vapor density 
3.5 (vs air)
vapor pressure 
10 mm Hg ( 36 °C)
refractive index 
n20/D 1.390(lit.)
Flash point:
130 °F
storage temp. 
Store at RT.
solubility 
Miscible with ether, chloroform and benzene.
form 
Liquid
color 
Colorless
Specific Gravity
1.082
PH
3 (10g/l, H2O, 20°C)
Odor
Very strong; pungent; vinegar-like characteristic odor.
explosive limit
2.0-10.2%(V)
Water Solubility 
REACTS
Sensitive 
Moisture Sensitive
Merck 
14,56
BRN 
385737
Stability:
Stability Flammable. Incompatible with strong oxidizing agents, water, strong bases, alcohols.
CAS DataBase Reference
108-24-7(CAS DataBase Reference)
NIST Chemistry Reference
Acetic acid anhydride(108-24-7)
EPA Substance Registry System
Acetic acid, anhydride(108-24-7)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  C,Xn,F,Xi
Risk Statements  11-20/21/22-37/38-41-34-20/21-10-20/22-19-40
Safety Statements  26-39-45-36/37/39-33-16
RIDADR  UN 2924 3/PG 2
WGK Germany  3
RTECS  AK1925000
21
Autoignition Temperature 629 °F
TSCA  Yes
HazardClass  8
PackingGroup  II
HS Code  29152400
Hazardous Substances Data 108-24-7(Hazardous Substances Data)
Toxicity LD50 orally in rats: 1.78 g/kg (Smyth)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H226 Flammable liquid and vapour Flammable liquids Category 3 Warning
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H314 Causes severe skin burns and eye damage Skin corrosion/irritation Category 1A, B, C Danger P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

NFPA 704

Diamond Hazard Value Description
2
3 1
Health   3 Short exposure could cause serious temporary or moderate residual injury (e.g. liquid hydrogen, sulfuric acid, calcium hypochlorite, hexafluorosilicic acid)
Flammability   2 Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur and multiple finely divided suspended solids that do not require heating before ignition can occur. Flash point between 37.8 and 93.3 °C (100 and 200 °F). (e.g. diesel fuel, sulfur)
Instability   1 Normally stable, but can become unstable at elevated temperatures and pressures (e.g. propene)
Special  

(NFPA, 2010)

Acetic anhydride price

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Acetic anhydride Chemical Properties,Uses,Production

Description

Acetic anhydride (chemical formula: (CH3CO)2O) is the simplest isolable anhydride of a carboxylic acid, is widely used as a reagent in organic synthesis. It has an internal asymmetric structure, leading to its potent electrophilicity. In organic chemistry, it is mainly used in acetylation for the manufacture of commercially significant materials, e.g. it can be used for the conversion of cellulose to cellulose acetate and aspirin. It can also be used as a wood preservative. In starch industry, it is a common acetylation compound for acetylation of monoglyceride. It is also an esterification agent for the production of modified starches. It is produced by carbonylation of methyl acetate or the reaction between ketene and acetic acid.

References

https://en.wikipedia.org/wiki/Acetic_anhydride
https://pubchem.ncbi.nlm.nih.gov/compound/acetic_anhydride#section=Top

Description

Acetic anhydride is a colourless liquid and appreciably soluble in water. It is of ethanoic acid smell. Acetic acid anhydride is flammable, moisture sensitive, and incompatible with strong oxidising agents, water, strong bases, alcohols, metals, reducing agents, amines, ammonia, nitrates, nitric acid, permanganates, phenols, sodium hydroxide, hydrogen peroxide, chromium trioxide, potassium hydroxide, perchloric acid, and ethanol. Acetic anhydride is mainly used for the acetylation of cellulose to cellulose acetate for photographic film and other applications. Upon burning, acetic anhydride decomposes and produces toxic gases and toxic fumes including acetic acid fumes. It attacks many metals with or without the presence of water.

Chemical Properties

Acetic anhydride is a combustible, colorless, strongly refractive, liquid which has a strongly irritating odor.

Chemical Properties

Colorless liquid

Chemical Properties

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, formed by its reaction with the moisture in the air.
Formic anhydride is an even simpler acid anhydride, but it spontaneously decomposes, especially once removed from solution.

Uses

Acetic Anhydride is an esterifier for food starch; also used in combi- nation with adipic anhydride.

Uses

Acetic anhydride is an important solvent and acetylation agent. It is used for the manufacture of acetylcellulose, acetylsalicylic acid, acetanilide, nitrofurane, sulfonamides, vitamin B6 etc. Product Data Sheet

Uses

Preparation of anhydrous acetic acid in nonaqueous titrimetry.

Uses

manufacture of acetyl compounds, cellulose acetates. As acetulizer and solvent in examining wool fat, glycerol, fatty and volatile oils, resins; detection of rosin. Widely used in organic syntheses, e.g., as dehydrating agent in nitrations, sulfonations and other reactions where removal of water is necessary.

Definition

ChEBI: An cyclic carboxylic anhydride of acetic acid.

Production Methods

Acetic anhydride is produced by carbonylation of methyl acetate :
CH3CO2CH3 + CO → (CH3CO)2O
This process involves the conversion of methyl acetate to methyl iodide and an acetate salt. Carbonylation of the methyl iodide in turn affords acetyl iodide, which reacts with acetate salts or acetic acid to give the product. Rhodium iodide and lithium iodide are employed as catalysts. Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions. In contrast, the Monsanto acetic acid process, which also involves a rhodium catalyzed carbonylation of methyl iodide, is at least partially aqueous.
To a decreasing extent, acetic anhydride is also prepared by the reaction of ethenone (ketene) with acetic acid at 45–55 °C and low pressure (0.05–0.2 bar).
H2C= C= O + CH3COOH → (CH3CO)2O (ΔH = ?63 kJ/mol)
Ketene is generated by dehydrating acetic acid at 700–750 °C in the presence of triethyl phosphate as a catalyst or (in Switzerland and the CIS) by the thermolysis of acetone at 600–700 °C in the presence of carbon disulfide as a catalyst.
CH3COOH H2C= C= O + H2O (ΔH = +147 kJ/mol)
CH3COCH3 → H2C= C= O + CH4
The route from acetic acid to acetic anhydride via ketene was developed by Wacker Chemie in 1922, when the demand for acetic anhydride increased due to the production of cellulose acetate.
Due to its low cost, acetic anhydride is purchased, not prepared, for use in research laboratories.

Application

As indicated by its organic chemistry, Ac2O is mainly used for acetylations leading to commercially significant materials. Its largest application is for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. Similarly it is used in the production of aspirin (acetylsalicylic acid), which is prepared by the acetylation of salicylic acid.It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber.
In starch industry, acetic anydride is a common acetylation compound, used for the production of modified starches
Because of its use for the synthesis of heroin by the diacetylation of morphine, acetic anhydride is listed as a U.S. DEA List II precursor, and restricted in many other countries.

Reactions

introduction of acetyl groups to organic substrates . In these conversions, acetic anhydride is viewed as a source of CH3CO+. Alcohols and amines are readily acetylated. For example, the reaction of acetic anhydride with ethanol yields ethyl acetate:
(CH3CO)2O + CH3CH2OH → CH3CO2CH2CH3 + CH3COOH
Often a base such as pyridine is added to function as catalyst. In specialized applications, Lewis acidic scandium salts have also proven effective catalysts.
Aromatic rings are acetylated, usually in the presence of an acid catalyst. Illustrative is the conversion of benzene to aceto phenone:
(CH3CO)2O + C6H6 → CH3COC6H5 + CH3CO2H
Ferrocene can be acetylated as well:
Cp2Fe + (CH3CO)2O → CpFe(C5H4COCH3).

General Description

A clear colorless liquid with a strong odor of vinegar. Flash point 129°F. Corrosive to metals and tissue. Density 9.0 lb /gal. Used to make fibers, plastics, pharmaceuticals, dyes, and explosives.

Air & Water Reactions

Flammable. Reacts violently with water to generate acetic acid . This reaction is heightened by the presence of mineral acids (nitric, perchloric, sulfuric acid, etc.) [Chem. Eng. News 25, 3458].

Reactivity Profile

Acetic anhydride reacts violently on contact with water, steam, methanol, ethanol, glycerol and boric acid. Reaction with water is particularly dangerous in presence with mineral acids (e.g., nitric, perchloric, chromic, sulfuric acid) [Chem. Eng. News 25, 3458]. Potentially explosive reactions with oxidizing reagents such as barium peroxide, chromium trioxide, chromic acid, hypochlorous acid, nitric acid, perchloric acid, peroxyacetic acid, potassium permanganate, hydrogen peroxide. [Sax, 9th ed., 1996, p. 15]. Reacts violently with metal nitrates used as nitrating agents [Davey W. et al., Chem. & Ind., 1948, p. 814].

Health Hazard

Liquid is volatile and causes little irritation on uncovered skin. However, causes severe burns when clothing is wet with the chemical or if it enters gloves or shoes. Causes skin and eye burns and irritation of respiratory tract. Nausea and vomiting may develop after exposure.

Fire Hazard

Flash Point (°F): 136 ℃; 120 ℃; Flammable Limits in Air (%): 2.7 - 10.0; Fire Extinguishing Agents: Water spray, dry chemical, alcohol foam, or carbon dioxide; Fire Extinguishing Agents Not To Be Used: Water and foam react, but heat liberated is not enough to create a hazard. Dry chemical forced below the surface can cause foaming and boiling; Special Hazards of Combustion Products: Irritating vapors generated upon heating; Behavior in Fire: Not pertinent; Ignition Temperature (°F): 600; Electrical Hazard: Not pertinent; Burning Rate: 3.3 mm/min.

Chemical Reactivity

Reactivity with Water: Reacts slowly with water, but considerable heat is liberated when contacted with spray water; Reactivity with Common Materials: Corrodes iron, steel and other metals; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Dilute with water and use sodium bicarbonate solution to rinse; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Moderately toxic by inhalation, ingestion, and skin contact. A skin and severe eye irritant. A flammable liquid. A fire and explosion hazard when exposed to heat or flame. Potentially explosive reactions with barium peroxide, boric acid, chromium trioxide, 1,3diphenyltriazene, hydrochloric acid + water, hypochlorous acid, nitric acid, perchloric acid + water, peroxyacetic acid, potassium permanganate, tetrafluoroboric acid, 4toluenesulfonic acid + water, and acetic acid + water. Reactions with ethanol + sodium hydrogen sulfate, and hydrogen peroxide form explosive products. Reactions with ammonium nitrate + hexamethylenetetrammonium acetate + nitric acid form as products the military explosives RDX and HMX. Reacts violently with N-tert-butyl-phthalimic acid + tetrafluoroboric acid, chromic acid, glycerol + phosphoryl chloride, and metal nitrates (e.g., copper or sodium nitrates). Incompatible with 2-aminoethanol, aniline, chlorosulfonic acid, (CrOs + acetic acid), ethylene-diamine, ethyleneimine, glycerol, oleum, HF, permanganates, NaOH, Na2O2, H2SO4, water, N2O2, (glycerol + phosphoryl chloride). When heated to decomposition it emits toxic fumes; can react vigorously with oxidizing materials, wdl react violently on contact with water or steam. Used in production of drugs of abuse. To fight fire, use CO2, dry chemical, water mist, alcohol foam. See also ANHYDRIDES.

Potential Exposure

Acetic anhydride is used as an acetylating agent or as a solvent in the manufacture of cellulose acetate, acetanilide, aspirin, synthetic fibers, plastics, explosives, resins, perfumes, and flavorings; and it is used in the textile dyeing industry. It is widely used as a pharmaceutical intermediate and as a pesticide intermediate

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately with large amounts of water. If this chemical contacts the skin, quickly remove clothing and immediately wash area with large amounts of water. If a person breathes this chemical, move the exposed person to fresh air at once and perform (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if hearth action hasstopped. When this chemical has been swallowed, get medical attention immediately. If victim is conscious, administer water or milk. Do not induce vomiting

Shipping

UN1715 Acetic anhydride, Hazard class: 8; Labels: 8-Corrosive material, 3-Flammable liquid.

Purification Methods

Adequate purification can usually be achieved by fractional distillation through an efficient column. Acetic acid can be removed by prior refluxing with CaC2 or with coarse Mg filings at 80-90o for 5days, or by distillation from a large excess of quinoline (1% AcOH in quinoline) at 75mm pressure. Acetic anhydride can also be dried by standing with Na wire for up to a week, removing the Na and distilling it under vacuum. (Na reacts vigorously with acetic anhydride at 65-70o). Dippy & Evans [J Org Chem 15 451 1950] let the anhydride (500g) stand over P2O5 (50g) for 3hours, then decanted it and stood it with ignited K2CO3 for a further 3hours. The supernatant liquid was distilled and the fraction b 136-138o was further dried with P2O5 for 12hours, followed by shaking with ignited K2CO3, before two further distillations through a five-section Young and Thomas fractionating column. The final material distilled at 137.8-138.0o. It can also be purified by azeotropic distillation with toluene: the azeotrope boils at 100.6o. After removal of the remaining toluene, the anhydride is distilled [sample had a specific conductivity of 5 x 10-9 ohm-1cm -1]. [Beilstein 2 H 96, 2 I 39, 2 II 91, 2 III 134, 2 IV 94.] Rapid procedure: Shake with P2O5, separate, shake with dry K2CO3 and fractionally distil.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, alcohols, chromic acid (violent reaction), amines, strong caustics; finely divided metals. Contact with water forms acetic acid and liberates a large amount of heat. Corrosive to iron, steel and other metals.

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.

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