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Encyclopedia > Acetic anhydride
Acetic anhydride
Acetic anhydride
General
Systematic name Ethanoyl ethanoate
Other names Acetic anhydride
Acetic acid anhydride
Acetylacetate
Acetyl oxide
Acetic oxide
Ethanoic anhydride
Molecular formula C4H6O3
SMILES CC(=O)OC(=O)C
Molar mass 102.1 g/mol
Appearance clear liquid
CAS number [108-24-7]
Properties
Density and phase 1.08 g/cm3, liquid
Solubility in water 2.6% by weight; rapidly reacts to
form acetic acid
Melting point −73.1 °C
Boiling point 139.9 °C
Dipole moment  ? D
Hazards
MSDS External MSDS
EU classification Corrosive (C)
NFPA 704 Health Flammability Reactivity
R-phrases R10, R20/22, R34
S-phrases S1/2, S26, S36/37/39, S45
Flash point 54 °C
RTECS number AK1925000
Supplementary data page
Structure and
properties		 n, εr, etc.
Thermodynamic
data		 Phase behaviour
Solid, liquid, gas
Spectral data UV, IR, NMR, MS
Related compounds
Related acid anhydrides Propionic anhydride
Related compounds Acetic acid
Acetyl chloride
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Acetic anhydride, also known as ethanoic anhydride, is one of the simplest of acid anhydrides. It has the chemical formula C4H6O3 or (CH3CO)2O. Acetic anhydride is corrosive, flammable, and its vapour is irritating to the eyes and upper respiratory tract. Image File history File links Acetic_anhydride. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... Flash point 43 Â°C R-phrases , S-phrases , , , U.S. Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Nfpa_f2_w. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a liquid is the lowest temperature at which it can form an ignitable mixture with air. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index of a material is the factor by which the phase velocity of electromagnetic radiation is slowed relative to vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... It has been suggested that Mass spectrum be merged into this article or section. ... Acid anhydrides have the general formula (RCO)2O, and appear to be the dehydration product of two carboxylic acid molecules. ... Flash point 43 Â°C R-phrases , S-phrases , , , U.S. Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... Acetyl chloride, also known as ethanoyl chloride, is an acid chloride derived from acetic acid. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Acid anhydrides have the general formula (RCO)2O, and appear to be the dehydration product of two carboxylic acid molecules. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ...

Contents


Properties

Acetic anhydride is a colourless liquid and smells strongly of vinegar. The smell is due to a reaction with the moisture in the air forming acetic acid. Vinegar is often infused with spices or herbs—as here, with oregano. ... Flash point 43 Â°C R-phrases , S-phrases , , , U.S. Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ...


Acetic anhydride dissolves in water to approximately 2.6% by weight[1]; however, it is not possible to keep a solution of acetic anhydride because it decomposes within a few minutes (the exact time being dependent upon the temperature) into a solution of acetic acid[2].


Production

Acetic acid condensation

The production of acetic anhydride by condensation of acetic acid is a major application using about 25% to 30% of the global production of acetic acid. [3] Condensation is the change in matter of a substance to a denser phase, such as gas (or vapor) to a liquid. ... Flash point 43 Â°C R-phrases , S-phrases , , , U.S. Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... Image File history File links Download high resolution version (4941x773, 21 KB) Summary Description: Condensation of acetic acid to acetic anhydride. ...


Alcohol and ester

Another synthesis of acetic anhydride is the reaction of acetyl chloride with sodium acetate: General formula of an ester of a carboxylic acid. ... Acetyl chloride, also known as ethanoyl chloride, is an acid chloride derived from acetic acid. ... Sodium acetate, also known as sodium ethanoate, is used in a number of industries: Textile industry: to neutralize sulphuric acid and as a resist to aniline dyes Leather industry: as a pickling agent in chrome tanning Chemical industry: in the manufacture of diazo compounds Paper industry: as a buffering agent...

H3C-C(=O)Cl + H3C-COO− Na+ → Na+Cl− + H3C-CO-O-CO-CH3

Uses

Common uses of acetic anhydride are in the production of clothes (cellulose acetate), in the chemical synthesis of aspirin (acetyl salicylic acid) from salicylic acid, and in the production of heroin (diacetylmorphine) from morphine. It is most widely used as a chemical reagent for acetylation. [4] In chemistry, the phrase chemical synthesis appears to have one of two meanings. ... Aspirin or acetylsalicylic acid is a drug in the family of salicylates, often used as an analgesic (against minor pains and aches), antipyretic (against fever), and anti-inflammatory. ... Salicylic acid is a colorless, crystalline organic carboxylic acid. ... Heroin or diacetylmorphine (INN) is a semi-synthetic opioid. ... Morphine (INN), the principal active agent in opium, is a powerful opioid analgesic drug. ... When purchasing or preparing chemicals, reagent describes chemical substances of sufficient purity for use in chemical analysis, chemical reactions or physical testing. ... Acetylation describes a reaction, usually with acetic acid, that introduces an acetyl functional group into an organic compound. ...


Reactions

Hydrolysis of acetic anhydride produces acetic acid slowly at room temperature:

(CH3CO)2O + H2O → 2CH3COOH

Acetic anhydride also reacts under gentle heating with alcohols to form acetic acid and an ester. [5] For example, the reaction of acetic anhydride with ethanol is: Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless chemical compound, one of the alcohols that is most often found in alcoholic beverages. ...

(CH3CO)2O + CH3CH2OH → CH3COOCH2CH3 + CH3COOH

Here, the ester produced is ethyl acetate. Often a base such as pyridine is added to remove the acetic acid by-product. Ethyl acetate, also known as acetic acid ethyl ester, ethyl ethanoate, acetic ether or acetic ester, is a clear, flammable liquid with a characteristic, not unpleasant smell like certain glues or nail polish removers. ... R-phrases , , , S-phrases , , Flash point 20 °C Supplementary data page Structure and properties n, εr, etc. ...


Safety

Corrosive
Enlarge
Corrosive

Acetic anhydride is corrosive and should be handled with care. Contact can cause delayed reaction burns and should be washed immediately with water. It is also moderately flammable therefore should not be used near an open flame. Water should not be used to fight a fire with acetic anhydride, alcohol foam or carbon dioxide are preferred as they will not react. [6] Image File history File links Gefahrensymbol_C.png it corodes ur mom Description: safety label C, corrosive License: public domain Source: w:de:Bild:Gefahrensymbol C.png Original description: Beschreibung: Gefahrensymbol Ätzend Quelle + Fotograf oder Zeichner: Selbst erstellt nach Vorlage Lizenzstatus: Public domain Authors: de:Benutzer:BirgitLachner de:Benutzer:Paddy de... Image File history File links Gefahrensymbol_C.png it corodes ur mom Description: safety label C, corrosive License: public domain Source: w:de:Bild:Gefahrensymbol C.png Original description: Beschreibung: Gefahrensymbol Ätzend Quelle + Fotograf oder Zeichner: Selbst erstellt nach Vorlage Lizenzstatus: Public domain Authors: de:Benutzer:BirgitLachner de:Benutzer:Paddy de... Corrosion is the destructive reaction of a metal with another material, e. ...


The vapour of acetic anhydride is corrosive to the mucous membranes of the respiratory tract and should be handled in a well-ventilated area. If the fumes are inhaled the person should be moved immediately to fresh air and medical attention sought. If the person is not breathing, cardiopulmonary resuscitation should be performed. [7] CPR performed on an adult Cardiopulmonary resuscitation (CPR) is an emergency first aid protocol for an unconscious person on whom both breathing and pulse cannot be detected. ...


Notes and references

  1. ^ British Petroleum. Acetic Anhydride: Frequently Asked Questions (PDF). URL accessed on 2006-05-03.
  2. ^ Celanese. Acetic Anhydride: Material Safety Data Sheet (PDF). URL accessed on 2006-05-03.
  3. ^ Greener Industry. Ethanoic Acid – Major Uses. URL accessed on 2006-03-25.
  4. ^ Science is Fun…. Chemical of the Week. URL accessed on 2006-03-25.
  5. ^ ChemGuide. Acid Anhydrides. URL accessed on 2006-03-25.
  6. ^ Data Sheets. International Occupational Safety and Health Information Centre. URL accessed on 2006-04-13.
  7. ^ NIOSH. Pocket Guide to Chemical Hazards. URL accessed on 2006-04-13.

2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... May 3 is the 123rd day of the year in the Gregorian calendar (124th in leap years). ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... May 3 is the 123rd day of the year in the Gregorian calendar (124th in leap years). ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... March 25 is the 84th day of the year in the Gregorian calendar (85th in leap years). ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... March 25 is the 84th day of the year in the Gregorian calendar (85th in leap years). ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... March 25 is the 84th day of the year in the Gregorian calendar (85th in leap years). ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... April 13 is the 103rd day of the year in the Gregorian calendar (104th in leap years). ... 2006 (MMVI) is a common year starting on Sunday of the Gregorian calendar. ... April 13 is the 103rd day of the year in the Gregorian calendar (104th in leap years). ...

See also

Acid anhydride
Acid anhydrides have the general formula (RCO)2O, and appear to be the dehydration product of two carboxylic acid molecules. ...


  Results from FactBites:
 
Chemical of the Week -- Acetic Acid and Acetic Anhydride (926 words)
Acetic anhydride is a clear, colorless, mobile (free-flowing) liquid with a sharp odor similar to that of acetic acid.
Acetic anhydride melts at –73°C, boils at 139°C, and has a density of 1.080 g/mL at 15°C. It is flammable with a flash point of 54°C. This compound is readily combustible and represents a fire hazard.
Because acetic anhydride reacts with water, it is sometimes used as a dehydrating agent in reaction mixtures where removal of water is necessary.
Reference.com/Encyclopedia/Acetic anhydride (413 words)
O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis.
It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with the moisture in the air.
Because acetic anhydride is not stable in water, the conversion is conducted under anhydrous conditions.
  More results at FactBites »


 

COMMENTARY     

MAKARAND DEOLE
9th May 2009 		In one project we want a concrete pit to be either coated or sprayed with resin .The pit is for acetic anhydride.I want to know the suitable material for the same.
regards

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