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Phthalic anhydride information


Phthalic anhydride
Skeletal formula of phthalic anhydride
Skeletal formula of phthalic anhydride
Space-filing model
Space-filing model
Names
Preferred IUPAC name
2-Benzofuran-1,3-dione[1]
Other names
Isobenzofuran-1,3-dione[1]
Phthalic anhydride[1]
Identifiers
CAS Number
  • 85-44-9 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
118515
ChEBI
  • CHEBI:36605 checkY
ChEMBL
  • ChEMBL1371297 ☒N
ChemSpider
  • 6552 checkY
ECHA InfoCard 100.001.461 Edit this at Wikidata
EC Number
  • 201-607-5
Gmelin Reference
27200
PubChem CID
  • 6811
RTECS number
  • TI3150000
UNII
  • UVL263I5BJ checkY
UN number 2214
CompTox Dashboard (EPA)
  • DTXSID2021159 Edit this at Wikidata
InChI
  • InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H checkY
    Key: LGRFSURHDFAFJT-UHFFFAOYSA-N checkY
SMILES
  • O=C1OC(=O)c2ccccc12
Properties
Chemical formula
C8H4O3
Molar mass 148.1 g/mol
Appearance white flakes
Odor characteristic, acrid[2]
Density 1.53 g/cm3, solid; 1.20 g/mL, molten[2]
Melting point 131.6 °C (268.9 °F; 404.8 K)
Boiling point 295 °C (563 °F; 568 K) sublimates
Solubility in water
0.62 g/100g (20—25 °C);
19.0 g/100g (100 °C);
reacts slowly
Vapor pressure 0.0015 mmHg (20 °C)[2]
Magnetic susceptibility (χ)
−67.31×10−6 cm3/mol
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Signal word
Danger
Hazard statements
H302, H315, H317, H318, H334, H335
Precautionary statements
P261, P264, P270, P271, P272, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P342+P311, P362, P363, P403+P233, 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 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 152 °C (306 °F; 425 K)
Explosive limits 1.7%–10.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
4020 mg/kg (oral, rat)
1520 mg/kg (oral, mouse)
800 mg/kg (oral, cat)
800–1600 mg/kg (oral, rat)
2210 mg/kg (oral, mouse)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 12 mg/m3 (2 ppm)[2]
REL (Recommended)
TWA 6 mg/m3 (1 ppm)[2]
IDLH (Immediate danger)
60 mg/m3[2]
Related compounds
Related compounds
Phthalic acid
Phthalimide
Phthalide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.[4]

  1. ^ a b c "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 835. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0512". National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Phthalic anhydride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).

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change colors depending on pH. They are formed by the reaction of phthalic anhydride with various phenols. They are a subclass of triarylmethane dyes....

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"weak" resistance to both moisture and heat although the inclusion of phthalic anhydride reportedly counteracts both of these characteristics. Cyanoacrylate...

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prolonged skin exposure. Naphthalene is a precursor in the production of phthalic anhydride. This application has been displaced by alternative technologies....

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Thalidomide

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that phthalic anhydride and L-glutamine under suitable conditions can react directly to form thalidomide. In the procedure, phthalic anhydride and L-glutamine...

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Oxo alcohol

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Sasol SABIC Oxo alcohols are used as solvents and are reacted with phthalic anhydride to form phthalates, which find use in commerce as vinyl plasticizers...

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ortho-xylene – both methyl groups can be oxidized to form (ortho-)phthalic acid phthalic anhydride para-xylene – both methyl groups can be oxidized to form terephthalic...

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Structure of an idealized alkyd resin derived from the polyol glycerol (red, a low molecular weight polyol) and phthalic anhydride....

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useful dye quinizarin is produced by diacylation of hydroquinone with phthalic anhydride. Hydroquinone undergoes oxidation under mild conditions to give benzoquinone...

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water. Diethyl phthalate is produced by the reaction of ethanol with phthalic anhydride, in the presence of a strong acid catalyst: It finds some use as a...

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steel/iron. Cast iron & steel are replaced with aluminum and plastics. Phthalic anhydride production shifts from catalytic oxidation of naphthalene to the o-xylol...

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