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85-44-9

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Identification

Name
Phthalic anhydride
CAS
85-44-9
Synonyms
1,2-BENZENEDICARBONIC ACID, ANHYDRIDE
1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE
1,3-DIOXOPHTHALAN
1,3-DIOXOPHTHALANE
1,3-ISOBENZOFURANDIONE
1,3-ISOBENZOFURANIDONE
AKOS BBS-00004337
O-PHTHALIC ANHYDRIDE
PHTHALANDIONE
PHTHALIC ACID ANHYDRIDE
PHTHALIC ANHYDRIDE
1,2-Benzenedicarboxylic Anhydride
1,2-benzenedicarboxylicanhydride
1,3-dihydro-1,3-dioxo-isobenzofura
1,3-dihydro-1,3-dioxoisobenzofuran
1,3-phthalandion
1,3-Phthalandione
2-Benzofuran-1,3-dione
Anhydrid kyseliny ftalove
Anhydride phtalique
EINECS(EC#)
201-607-5
Molecular Formula
C8H4O3
MDL Number
MFCD00005918
Molecular Weight
148.12
MOL File
85-44-9.mol

Chemical Properties

Appearance
Phthalic Anhydride is moderately flammable, white solid (flake) or a clear, colorless, mobile liquid (molten) Characteristic, acrid, choking odor
Appearance
white crystalline solid with choking odour
Melting point 
131-134 °C(lit.)

mp 
131-134 °C(lit.)

Boiling point 
284 °C(lit.)

bp 
284 °C(lit.)

density 
1,53 g/cm3
vapor density 
5.1 (vs air)

vapor pressure 
<0.01 mm Hg ( 20 °C)

refractive index 
1.4500 (estimate)
Fp 
152 °C
storage temp. 
Store at RT.
solubility 
6g/l (slow decomposition)
form 
Flaky Crystals
color 
White
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, moisture, strong acids. Dust may form an explosive mixture with air.
Odor
Characteristic choking odor
PH
2 (6g/l, H2O, 20℃)
PH Range
2 at 6 g/l at 20 °C
explosive limit
1.7-10.5%(V)
Water Solubility 
6 g/L (20 ºC)
Sensitive 
Moisture Sensitive
Merck 
14,7372
BRN 
118515
Henry's Law Constant
6.29 at 20 °C (approximate - calculated from water solubility and vapor pressure)
Exposure limits
NIOSH REL: TWA 6 mg/m3 (1 ppm), IDLH 60 mg/m3; OSHA PEL: TWA 12 mg/m3 (2 ppm); ACGIH TLV: TWA 1 ppm (adopted).
Contact allergens
Phthalic anhydride is used in the manufacture of unsaturated polyesters and as a curing agent for epoxy resins. When used as a pigment, it can be responsible for sensitization in ceramic workers. Phthalic anhydride per se is not responsible for the sensitization to the resin used in nail varnishes phthalic anhydride/trimellitic anhydride/ glycols copolymer.
CAS DataBase Reference
85-44-9(CAS DataBase Reference)
NIST Chemistry Reference
Phthalic anhydride(85-44-9)
EPA Substance Registry System
85-44-9(EPA Substance)

Hazard Information

Chemical Properties
white crystalline solid with choking odour
Uses
Phthalic Anhydride is an organic compound and the anhydride of phthalic acid (P384480). Phthalic Anhydride is an important industrial chemical commonly used in large-scale production of plasticizers f or plastics. Recent research have also evaluated Phthalic Anhydride as potential antibacterial agent.
Uses
manufacture of phthaleins, phthalates, benzoic acid, synthetic indigo, artificial resins (glyptal).
Definition
ChEBI: The cyclic dicarboxylic anhydride that is the anhydride of phthalic acid.
General Description
A colorless to white lustrous solid in the form of needles with a mild distinctive odor. Moderately toxic by inhalation or ingestion and a skin irritant. Melting point 64°F Flash point 305°F. Forms a corrosive solution when mixed with water. Used in the manufacture of materials such as artificial resins.
Reactivity Profile
PHTHALIC ANHYDRIDE(85-44-9) reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. Undergoes exothmeric nitration with fuming nitric acid-sulfuric acid and may give mixtures of the potentially explosive phthaloyl nitrates or nitrites or their nitro derivatives [Chem. & Ind. 20:790. 1972]. PHTHALIC ANHYDRIDE(85-44-9) reacts violently with CuO at elevated temperatures [Park, Chang-Man, Richard J. Sheehan. hthalic Acids and Other Benzenepolycarboxylic Acids Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. 2005]. Mixtures of PHTHALIC ANHYDRIDE(85-44-9) and anhydrous CO2 explode violently if heated [eaflet No. 5, Inst. of Chem., London, 1940].
Air & Water Reactions
Reacts, usually slowly with water to form phthalic acid and heat [Merck 11th ed. 1989]. The phthalic acid is somewhat soluble in water.
Health Hazard
Solid irritates skin and eyes, causing coughing and sneezing. Liquid causes severe thermal burns.
Potential Exposure
Phthalic anhydride is used in plasticizers; in the manufacture of phthaleins; benzoic acid; alkyd and polyester resins; synthetic indigo; and phthalic acid;which is used as a plasticizer for vinyl resins. To a lesser extent, it is used in the production of alizarin, dye, anthranilic acid; anthraquinone, diethyl phthalate; dimethyl phthalate; erythrosine, isophthalic acid; methylaniline, phenolphthalein, phthalamide, sulfathalidine, and terephthalic acid. It has also found uses as a pesticide intermediate.
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. If victim is conscious, administer water, or milk. Do not induce vomiting.
Fire Hazard
Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.
Shipping
UN2214 Phthalic anhydride with>.05 % maleic anhydride, Hazard class: 8; Labels: 8-Corrosive material.
Incompatibilities
Dust forms an explosive mixture with air. Phthalic anhydride reacts exothermically with water. The reactions are sometimes slow, but can become violent when local heating accelerates their rate. Acids accelerate the reaction with water. Incompatible with acids, strong oxidizing agents, alcohols, amines, and bases. Converted to phthalic acid in hot water. 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. caustics, ammonia, amines, water. Reacts violently with copper oxide or sodium nitrite 1 heat.
Description

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. This colourless solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics.
Phthalic anhydride
Phthalic anhydride is an important chemical intermediate in the plastics industry from which are derived numerous phthalate esters that function as plasticizers in synthetic resins. Phthalic anhydride itself is used as a monomer for synthetic resins such as glyptal, the alkyd resins, and the polyester resins.
Phthalic anhydride is also used as a precursor of anthraquinone, phthalein, rhodamine, phthalocyanine, fluorescein, and xanthene dyes.
Phthalic anhydride is used in the synthesis of primary amines, the agricultural fungicide phaltan, and thalidomide. Other reactions with phthalic anhydride yield phenolphthalein, benzoic acid, phthalylsulfathiazole (an intestinal antimicrobial agent), and orthophthalic acid.


Waste Disposal
Use a licensed professional waste disposal service to dispose of this material. 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. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
Physical properties
Colorless to pale cream crystals with a characteristic, choking odor. Moisture sensitive. Odor threshold concentration is 53 ppb (quoted, Amoore and Hautala, 1983).
Synthesis Reference(s)
The Journal of Organic Chemistry, 25, p. 616, 1960 DOI: 10.1021/jo01074a035
Synthesis, p. 612, 1973
Tetrahedron Letters, 20, p. 2301, 1979 DOI: 10.1016/S0040-4039(01)93957-7
Pharmaceutical Applications
Phthalic anhydride reacted with cellulose acetate forms cellulose acetate phthalate (CAP), a common enteric coating excipient that has also been shown to have antiviral activity. Phthalic anhydride is a degradation product of CAP.
Chemical Synthesis
Phthalic anhydride is a precursor to a variety of reagents useful in organic synthesis. Important derivatives include phthalimide and its many derivatives. Chiral alcohols form half-esters (see above), and these derivatives are often resolvable because they form diastereomeric salts with chiral amines such as brucine. A related ring - opening reaction involves peroxides to give the useful peroxy acid:
C6H4(CO)2O + H2O2 → C6H4(CO3H)CO2H.
Environmental Fate
Chemical/Physical. Reacts with water to form o-phthalic acid (Kollig, 1993; Windholz et al., 1983). Based on an observed rate constant of 7.9 x 10-9/sec, the hydrolysis half-life is 88 sec (Hawkins, 1975).
Pyrolysis of phthalic anhydride in the presence of polyvinyl chloride at 600 °C for 10 min gave the following compounds: biphenyl, fluorene, benzophenone, 9-fluorenone, o-terphenyl, 9-phenylfluorene, and three unidentified compounds (Bove and Dalven, 1984).
Purification Methods
Distil the anhydride under reduced pressure. Purify it from the acid by extracting with hot CHCl3, filtering and evaporating. The residue is crystallised from CHCl3, CCl4 or *benzene, or sublimed. Fractionally crystallise it from its melt. Dry it under vacuum at 100o. [Saltiel J Am Chem Soc 108 2674 1986, Beilstein 17/11 V 253.]
Preparation of phthalate esters
As with other anhydrides, the alcoholysis reaction is the basis of the manufacture of phthalate esters, which are widely used (and controversial - see endocrine disruptor) plasticizers. In the 1980s, approximately 6.5×109 kg of these esters were produced annually, and the scale of production was increasing each year, all from phthalic anhydride. The process begins with the reaction of phthalic anhydride with alcohols, giving the monoesters:
C6H4(CO)2O + ROH → C6H4(CO2H)CO2R
The second esterification is more difficult and requires removal of water:
C6H4(CO2H)CO2R + ROHC6H4(CO2R)2 + H2O
The most important di ester is bis (2-ethyl hexyl) phthalate ("DEHP"), used in the manufacture of polyvinyl chloride.
Precursor to dyestuffs
Phthalic anhydride is widely used in industry for the production of certain dyes. A well-known application of this reactivity is the preparation of the anthroquinone dye quinizarin by reaction with parachloro phenol followed by hydrolysis of the chloride.
Toxicity evaluation
Phthalic anhydride modulates lipid mediator release and cytokine formation and has sensitizing effects on the respiratory tract. The local irritating effect particularly on the mucous membranes probably depends on the hydrolysis to phthalic acid.

Safety Data

Hazard Codes 
Xn
Risk Statements 
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R42/43:May cause sensitization by inhalation and skin contact .
Safety Statements 
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S46:If swallowed, seek medical advice immediately and show this container or label .
S22:Do not breathe dust .
RIDADR 
2214
WGK Germany 
1

RTECS 
TI3150000


10-21
Autoignition Temperature
580 °C
TSCA 
Yes
HazardClass 
8
PackingGroup 
III
HS Code 
29173500
Safety Profile
Poison by ingestion. Experimental teratogenic effects. A corrosive eye, skin , and mucous membrane irritant. A common air contaminant. Combustible when exposed to heat or flame; can react with oxidzing materials. Moderate explosion hazard in the form of dust when exposed to flame. The production of ths material has caused many industrial explosions. Mixtures with copper oxide or sodium nitrite explode when heated. Violent reaction with nitric acid + sulfuric acid above 80℃. To fight fire, use CO2, dry chemical. Used in plasticizers, polyester resins, and alkyd resins, dyes, and drugs. See also ANHYDRIDES.
Hazardous Substances Data
85-44-9(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1530 mg/kg LD50 dermal Rabbit > 3160 mg/kg

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