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Acetic anhydride information


Acetic anhydride
Acetic anhydride
Acetic anhydride
Names
Preferred IUPAC name
Acetic anhydride
Systematic IUPAC name
Ethanoic anhydride
Other names
Ethanoyl ethanoate
Acetic acid anhydride
Acetyl acetate
Acetyl oxide
Acetic oxide
Identifiers
CAS Number
  • 108-24-7 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:36610 checkY
ChEMBL
  • ChEMBL1305819
ChemSpider
  • 7630 checkY
ECHA InfoCard 100.003.241 Edit this at Wikidata
EC Number
  • 203-564-8
PubChem CID
  • 7918
RTECS number
  • AK1925000
UNII
  • 2E48G1QI9Q checkY
UN number 1715
CompTox Dashboard (EPA)
  • DTXSID0024395 Edit this at Wikidata
InChI
  • InChI=1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3 checkY
    Key: WFDIJRYMOXRFFG-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
    Key: WFDIJRYMOXRFFG-UHFFFAOYAH
SMILES
  • O=C(OC(=O)C)C
  • CC(=O)OC(=O)C
Properties
Chemical formula
 C4H6O3
Molar mass 102.089 g·mol−1
Appearance colorless liquid
Density 1.082 g cm−3, liquid
Melting point −73.1 °C (−99.6 °F; 200.1 K)
Boiling point 139.8 °C (283.6 °F; 412.9 K)
Solubility in water
 2.6 g/100 mL, reacts (see text)
Vapor pressure 4 mmHg (20 °C)[1]
Magnetic susceptibility (χ)
 −52.8·10−6 cm3/mol
Refractive index (nD)
 1.3901
Thermochemistry[2]
Std enthalpy of
formation (ΔfH⦵298)
 −624.4 kJ/mol
Pharmacology
Legal status
  • AU: S6 (Poison)
  • CA: Schedule VI
Hazards
GHS labelling:
Pictograms
 GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word
 Danger
Hazard statements
 H226, H302, H314, H330
Precautionary statements
 P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
2
1
W
Flash point 49 °C (120 °F; 322 K)
Autoignition
temperature
 316 °C (601 °F; 589 K)
Explosive limits 2.7–10.3%
Lethal dose or concentration (LD, LC):
LC50 (median concentration)
 1000 ppm (rat, 4 h)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 5 ppm (20 mg/m3)[1]
REL (Recommended)
 C 5 ppm (20 mg/m3)[1]
IDLH (Immediate danger)
 200 ppm[1]
Safety data sheet (SDS) ICSC 0209
Related compounds
Related acid anhydrides
 Propionic anhydride
Related compounds
 Acetic acid
Acetyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

  1. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0003". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
  3. ^ "Acetic anhydride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

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Acetic anhydride

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Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride...

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Organic acid anhydride

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anhydride. Thus, (CH3CO)2O is called acetic anhydride. Mixed (or unsymmetrical) acid anhydrides, such as acetic formic anhydride (see below), are known, whereby...

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Acetic acid

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the condensation of two molecules of acetic acid is acetic anhydride. The worldwide production of acetic anhydride is a major application, and uses approximately...

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Acetic formic anhydride

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Acetic formic anhydride is an organic compound with the chemical formula C 3H 4O 3, which can be viewed as the mixed anhydride of acetic acid and formic...

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Acetic oxalic anhydride

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Acetic oxalic anhydride is an organic compound with a chemical formula of C 6H 6O 6 and a structural formula of (H3C-(C=O)-O-(C=O)-)2. It can be viewed...

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Monsanto process

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acetate salts or acetic acid to give the anhydride. Rhodium iodides and lithium salts are employed as catalysts. Because acetic anhydride hydrolyzes, the...

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Cellulose acetate

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chemist Paul Schützenberger discovered that cellulose reacts with acetic anhydride to form cellulose acetate. The German chemists Arthur Eichengrün and...

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Trifluoroacetic anhydride

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Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride. Trifluoroacetic anhydride was...

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Carbonylation

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Monsanto acetic acid process and Cativa process, which convert methanol to acetic acid. In another major industrial process, acetic anhydride is prepared...

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Acetylated wood

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produced from a chemical reaction (named as acetylation), involving acetic anhydride and a modification process to make wood highly resistant to biological...

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Methyl acetate

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polish removers. Acetic anhydride is produced by carbonylation of methyl acetate in a process that was inspired by the Monsanto acetic acid synthesis....

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Acetaldehyde

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crotonaldehyde. Urea and acetaldehyde combine to give a useful resin. Acetic anhydride reacts with acetaldehyde to give ethylidene diacetate, a precursor...

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Acetylated distarch adipate

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modified starches. This is a starch that is treated with acetic anhydride and adipic acid anhydride to resist high temperatures. No acceptable daily intake...

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Clandestine chemistry

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by acid-base extraction and turned into heroin by reacting it with acetic anhydride. Other drugs (such as methamphetamine and MDMA) are normally made from...

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Methanol

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acetic acid and acetic anhydride. These processes include the Monsanto acetic acid synthesis, Cativa process, and Tennessee Eastman acetic anhydride process...

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Acetyl chloride

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industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: ( CH 3 CO ) 2 O + HCl ⟶ CH...

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Pummerer rearrangement

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acetic anhydride. The stoichiometry of the reaction is: RS(O)CHR'2 + Ac2O → RSC(OAc)R'2 + AcOH Aside from acetic anhydride, trifluoroacetic anhydride...

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Avantor

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opioid epidemic. According to Bloomberg, one of their compounds "acetic anhydride", was used illicitly by drug traffickers to convert crude opium into...

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Hydroxyl value

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substance with acetic anhydride in pyridine solvent. After completion of the reaction, water is added, and the remaining unreacted acetic anhydride is converted...

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Black tar heroin

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acetylating agent, acetic anhydride. The acetic anhydride reacts with the moisture to produce the milder acetylating agent glacial acetic acid which is unable...

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Peracetic acid

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will not form peracetic acid. As an alternative, acetyl chloride and acetic anhydride can be used to generate a solution of the acid with lower water content...

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Acetylation

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achieved using these three reagents: Acetic anhydride. This reagent is common in the laboratory; its use cogenerates acetic acid. Acetyl chloride. This reagent...

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Phenyl acetate

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Phenyl acetate is the ester of phenol and acetic acid. It can be produced by reacting phenol with acetic anhydride or acetyl chloride. Phenyl acetate can...

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RDX

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nitrate/nitric acid mixture as a nitrating agent in a medium of acetic acid and acetic anhydride. RDX was crucial to the war effort and the current batch-production...

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Organorhodium chemistry

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with methyl iodide. The related Tennessee Eastman acetic anhydride process affords acetic anhydride by carbonylation of methyl acetate. CH3CO2CH3 + CO...

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Opium

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Morphine is converted into heroin by a simple chemical reaction with acetic anhydride, followed by purification. Especially in Mexican production, opium...

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Acetyl nitrate

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with the formula CH3C(O)ONO2. It is classified as the mixed anhydride of nitric and acetic acids. It is a colorless explosive liquid that fumes in moist...

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Polyoxymethylene

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Dal Nogare, who discovered that reacting the hemiacetal ends with acetic anhydride converts the readily depolymerizable hemiacetal into a thermally stable...

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