Phthalic anhydride

Iupac Name：2-benzofuran-1,3-dione

CAS No.: 85-44-9

Molecular Weight：148.117

Modify Date.: 2022-11-29 04:28

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Phthalic anhydride
1.2 Synonyms: 1,2-Benzenedicarboxylic Anhydride 1,3-dihydro-2h-imidazol-2-on 1,3-dihydro-2H-imidazol-2-one 1,3-DIHYDRO-IMIDAZOL-2-ONE 1,3-dihydroimidazolone 1,3-dihydroisobenzofuran-1,3-dione 1,3-isobenzofurandione 1H-imidazol-2(3H)-one 2(3H)-Oxo-1H-imidazole 2,3-dihydro-1H-imidazol-2-one 2,3-DIHYDRO-IMIDAZOL-2-ONE 2,3-Dihydroimidazole-2-one 2-Benzofuran-1,3-dione 2-hydroxyimidazole 4-imidazolin-2-one AKOS BBS-00004337 Anhydrid kyseliny ftalove Anhydride phtalique anhydridephtalique anhydridephtalique(etatvitreux) anhydridephtalique(french) EINECS 201-607-5 isobenzofuran-1,3-dione MFCD00005918 o-Phthalic acid anhydride phthallic anhydride sd8591 shellsd-8591

1.3 CAS No.: 85-44-9

1.4 CID: 6811

1.5 EINECS(EC#): 201-607-5

1.6 Molecular Formula: C8H4O3 (isomer)

1.7 Inchi: InChI=1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H

1.8 InChkey: LGRFSURHDFAFJT-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C(=O)OC2=O

1.10 Isomers Smiles: C1=CC=C2C(=C1)C(=O)OC2=O

2. Properties

2.1 Density: 1.53

2.1 Melting point: 129-132℃

2.1 Boiling point: 267.4° F (NTP, 1992)

2.1 Refractive index: 1.646

2.1 Flash Point: 305° F (NTP, 1992)

2.2 Precise Quality: 148.01600

2.2 PSA: 43.37000

2.2 logP: 0.99720

2.2 Solubility: 6g/l (slow decomposition)

2.3 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.4 VaporDensity: 5.1 (vs air)

2.5 AnalyticLaboratory Methods: Method: EPA-RCA 8270D; Procedure: gas chromatography/mass spectrometry; Analyte: phthalic anhydride;; Matrix: solid waste matrices, soils, air sampling media and water; samples; Detection Limit: 100 ug/L.

2.6 Appearance: white crystalline solid with choking odour

2.7 AutoIgnition: 1058° F (USCG, 1999)

2.8 Storage: Moisture Sensitive. Ambient temperatures.

2.9 Chemical Properties: Phthalic Anhydride is moderately flammable, white solid (flake) or a clear, colorless, mobile liquid (molten) Characteristic, acrid, choking odor.

2.10 Physical Properties: Colorless to pale cream crystals with a characteristic, choking odor. Moisture sensitive. Odorthreshold concentration is 53 ppb (quoted, Amoore and Hautala, 1983).

2.11 Color/Form: White

2.12 Contact Allergens: Phthalic anhydride is used in the manufacture of unsaturatedpolyesters and as a curing agent for epoxy resins.When used as a pigment, it can be responsible for sensitizationin ceramic workers. Phthalic anhydride per se isnot responsible for the sensitization to the resin used innail varnishes phthalic anhydride/trimellitic anhydride/glycols copolymer.

2.13 Decomposition: Phthalic anhydride; hydrolyzes rapidly in the presence of water; forming phthalic acid;. Half-life for phthalic anhydride; was 30.5 seconds at pH 7.24. At pH 6.8 the half-life of phthtalic anhydride in water; was prolonged to 61 seconds.

2.14 Heat of Combustion: -3259 kJ/mol at 25 deg C [

2.15 Heat of Vaporization: 65.3 kJ/mol at 131 deg Cl

2.16 Ionization Potential: 10.00 eV

2.17 Odor: Characteristic choking odor

2.18 Odor Threshold: 0.32-0.72 mg/cu m

2.19 PH: 2 (6g/l, H2O, 20℃)

2.20 Physical: PHTHALIC ANHYDRIDE; is 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.

2.21 Water Solubility: 6 g/L (20 oC)

2.22 Spectral Properties: Sadtler reference number: 8656 (prism, ir); max absorption (carbon tetrachloride): 287 nm (log E= 3.2), 295 nm (log E= 3.3)
IR: 4822 (Coblentz Society Spectral Collection)
UV: 18 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 10133 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 281 (Johnson & Jankowski. Carbon-13 NMR Spectra. John Wiley & Sons, New York)
MASS: 34987 (NIST/EPA/MSDC Mass Spectral Database, 1990 version); 847 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

2.23 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, moisture, strong acids. Dust may form an explosive mixture with air.

2.24 StorageTemp: Store below +30°C.

2.25 Surface Tension: 35.5 dynes/cm = 0.0355 N/m at 155 deg C

2.26 Toxicity Summary: IDENTIFICATION AND USE: Phthalic anhydride; presents in many forms including a colorless liquid or needles, white needles, and white flakes. It has a mild, characteristic acrid odor. Phthalic anhydride; is an important intermediate in the chemical industry. The major subsequent product groups are alkyd resins, plasticizers, hardener for resins, polyesters, pigments, chlorinated products, pharmaceutical intermediates, insecticides, diethyl phthalate;, dimethyl phthalate;, and laboratory reagent. It is also widely used in the production of as an anti-scorching agent, a rubber hardener, and as a light- and heat-stabilizer of polyolefins. Phthalic anhydride; containing materials are used in coatings applications for home appliances, automobiles, medical devices and furniture. HUMAN EXPOSURE AND TOXICITY: For humans, phthalic anhydride; in the form of vapor, fume or dust is a primary irritant to mucous membranes and the upper respiratory tract. Workers exposed to mixtures of phthalic acid; and phthalic anhydride; developed conjunctivitis, bloody nasal discharge, atrophy of the nasal mucosa, hoarseness, cough, occasional bloody sputum, bronchitis, and emphysema. Several cases of bronchial asthma resulted; skin sensitization with occasional urticaria and eczematous response were also documented. Clinical sensitization of phthalic anhydride; occurred in a worker who developed symptoms of rhinorrhea, lacrimation, and wheezing after chronic exposure. Positive skin tests, provocative bronchial challenges, and a high serum titer of specific IgE to phthalic anhydride; corroborated his clinical hypersensitivity. Bronchial provocation studies showed immediate airway obstruction. Sensitized people can have serological reactivity of phthalic anhydride;, both immunoglobulin E (IgE) and immunoglobulin G (IgG), but IgE appears to discriminate cases of asthma from workers without asthma better than IgG, because the prevalence of IgG is high in exposed workers. ANIMAL STUDIES: Phthalic anhydride; caused severe skin irritation in rabbits following 24 hr exposure. Phthalic anhydride; was also irritating to rabbit eyes in the Draize test. Phthalic acid; caused statistically significant increases in Th2 cytokines, IL-4, IL-5 and IL-13 in dermally sensitized and intratracheally challenged mice, compared with the control. Guinea pigs exposed to and challenged with 5.0 mg/cu m phthalic anhydride; dust had significant numbers of hemorrhagic lung foci; and animals with the greatest number of foci had high IgG antibody activity to phthalic anhydride;. Cats given 68 mg phthalic anhydride;/kg body weight for 90 days developed meteorism (tympanites) and diarrhea, and some excitation of the NS without other signs of intoxication. Rabbits given 20 mg/kg body weight for 3 months developed leukocytosis and increased aldolase activity. On gross pathology examination there was moderate parenchymatous dystrophy of the liver cells with slight perivascular lymphoid infiltration. In some studies, exposure to high doses of phthalic anhydride; can be fatal. Four mice exposed to sublimation of phthalic anhydride; 10 mg/L, 4 hr/day for 14 days exhibited slightly reduced breathing. One mouse died after the second day while a second one was found dead after the last day on test. Oral doses in rats (starting at 20 mg/kg/day) were doubled weekly; 0.89 g/kg was reached by ninth wk. Rats that died at high dosage had severe nephrosis, with destruction of tubular epithelium. Surviving animals had gastric ulceration. Phthalic acid; did not show evidence of carcinogenicity in male and female mice fed 16,346 or 32,692 ppm (males) and 12,019 or 24,038 ppm (females) for 2 years. Phthalic anhydride; was significantly teratogenic to mice: Branched ribs, fused vertebrae and cleft palate were the most common defects. In regards to genotoxicity, phthalic anhydride; was negative in Ames test using Salmonella typhimurium TA98, TA100, TA1535, and TA1537 with or without rat and hamster liver S-9 metabolic activation. There was a genotoxic effect found with phthalic anhydride; in vitro at extremely high, cytotoxic concentrations, and only in the absence of a metabolic activation system which is not expected to be relevant under in vivo conditions, where phthalic anhydride; is rapidly hydrolyzed to the non-genotoxic phthalic acid;. Chinese hamster ovary cells were exposed to higher doses (6, 8, 10 mM) for 3 hours in the presence or absence of S9; cells were then washed, further incubated and harvested at 20 hours from the beginning of the treatment. Phthalic anhydride; caused a decrease in pH when added to culture medium and was immediately neutralized with NaOH. Effects were observed in the main study only without S9 and only at the highest compound concentration which was very toxic (remaining cell counts 29 %) and gave precipitate. Chromosome aberration rate increased to 18.5 % at the highest dose compared with a control of 3%.

3. Use and Manufacturing

3.1 Definition: ChEBI: The cyclic dicarboxylic anhydride that is the anhydride of phthalic acid.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H315: Causes skin irritation [Warning Skin corrosion/irritation]
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes
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, and P501

3.3 Methods of Manufacturing: Prepared from naphthalene; by oxidation with a mixture of HgSO4 and CuSO4 in presence of H2SO4; by passing naphthalene; and oxygen; over a suitable catalyst at 400-500 deg C.

3.4 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.

3.5 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.]

3.6 Usage: The compound is a high-tonnage chemical and is widely used in a variety of industrial organic syntheses.

4. Safety and Handling

4.1 Symbol: GHS05, GHS07, GHS08

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R22;R37/38;R41;R42/43

4.1 Safety Statements: S22;S24/25;S26;S37/39;S46

4.1 Packing Group: III

4.1 Octanol/Water Partition Coefficient: log Kow = 1.60

4.2 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.

4.3 Other Preventative Measures: If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Neutralize spilled material with crushed limestone, soda ash, or lime.
Personnel protection: Avoid breathing vapors or dusts. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing.
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
NO open flames. Prevent deposition of dust; closed system, dust explosion-proof electrical equipment and lighting. PREVENT DISPERSION OF DUST! AVOID ALL CONTACT ... Do not eat, drink, or smoke during work.

4.4 Hazard Class: 8

4.4 Hazard Declaration: H302-H315-H317-H318-H334-H335

4.4 Cleanup Methods: 1. Ventilate area of spill. 2. For small quantities, sweep onto paper or other suitable material, place in an appropriate container & burn in a safe place (such as a fume hood). Large quantities may be reclaimed; however, if this is not practical, dissolve in a flammable solvent (such as alcohol) & atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. Liquid containing phthalic anhydride should be absorbed in vermiculite, dry sand, earth, or a similar material for disposal in a secure sanitary landfill.
Cover with soda ash or sodium bicarbonate. Mix and add water. Neutralize and drain into sewer with sufficient water.
Keep water away from release. Prompt cleanup and removal are necessary. Shovel into suitable dry container.
Environmental considerations: Air spill: Apply water spray or mist to knock down vapors.
Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
Environmental considerations: Land spill: Dig a pit, pnd, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using solid, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.
Sweep spilled substance into covered containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Personal protection: chemical protection suit including self-contained breathing apparatus.

4.5 DisposalMethods: [40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U190, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U190, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
Phthalic anhydride is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 deg C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 deg C and residence times of seconds for liquids and gases, and longer for solids.
The following wastewater treatment technologies have been investigated for phthalic acid: Concentration process: Biological Treatment. /Phthalic acid/

4.6 DOT Emergency Guidelines: /GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire or Explosion: 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.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat which will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Fire: Note: Most foams will react with the material and release corrosive/toxic gases. Small fires: CO2, dry chemical, dry sand, alcohol-resistant foam. Large fires: Water spray, fog or alcohol-resistant foam. ... Move containers from fire area if you can do it without risk. Use water spray or fog; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. A vapor suppressing foam may be used to reduce vapors. ... DO NOT GET WATER on spilled substance or inside containers. Use water spray to reduce vapors or divert vapor cloud drift. Avoid allowing water runoff to contact spilled material. Prevent entry into waterways, sewers, basements or confined areas. Small spills: Cover with DRY earth, DRY sand, or other non-combustible material followed with plastic sheet to minimize spreading or contact with rain. Use clean non-sparking tools to collect material and place it into loosely covered plastic containers for later disposal.
/GUIDE 156: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE/WATER-SENSITIVE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.

4.7 RIDADR: 2214

4.7 Fire Fighting Procedures: If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.
Use dry chemical, foam, carbon dioxide, or water spray. Water or foam may cause frothing. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.

4.8 FirePotential: Combustible solid
Combustible when exposed to heat or flame.

4.9 Caution Statement: P261-P280-P284-P304 + P340 + P312-P305 + P351 + P338 + P310-P342 + P311

4.9 Formulations/Preparations: Grade: Pure; technical.
Grades or purity: flake, molten; commercial: 99.8% purity.

4.10 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.

4.11 WGK Germany: 1

4.11 RTECS: TI3150000

4.11 Protective Equipment and Clothing: Coveralls &/or rubber apron; rubber shoes or boots; chemical goggles &/or face shield; Bureau of Mines organic vapor respirator (type AB); gauntlet-type leather or rubber gloves.
Wear special protective clothing and positive pressure self-contained breathing apparatus.
If contact with the material is anticipated, wear appropriate chemical protective clothing.
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Respirator Recommendations: Up to 30 mg/cu m: (APF = 5) Any quarter-mask respirator. Substance reported to cause eye irritation or damage; may require eye protection.
Respirator Recommendations: Up to 60 mg/cu m: (Assigned Protection Factor = 10) Any particulate respirator equipped with an N95, R95, or P95 filter (including N95, R95, and P95 filtering facepieces) except quarter-mask respirators. The following filters may also be used: N99, R99, P99, N100, R100, P100. Substance reported to cause eye irritation or damage; may require eye protection./(Assigned Protection Factor = 10) Any air-purifying, full-facepiece respirator equipped with an N95, R95, or P95 filter. The following filters may also be used: N99, R99, P99, N100, R100, P100./(Assigned Protection Factor = 25) Any powered air-purifying respirator with a high-efficiency particulate filter. Substance reported to cause eye irritation or damage; may require eye protection. /(Assigned Protection Factor = 10) Any supplied-air respirator. Substance reported to cause eye irritation or damage; may require eye protection./(Assigned Protection Factor = 50) Any self-contained breathing apparatus with a full facepiece.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned Protection Factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode./(Assigned Protection Factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape: (Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator with an N100, R100, or P100 filter./Any appropriate escape-type, self-contained breathing apparatus.
Safety goggles or eye protection in combination with breathing protection.

4.12 Reactivities and Incompatibilities: Strong oxidizers, water [Note: Converted to phthalic acid in hot water].
The exothermic nitration of phthalic acid or phthalic anhydride by a fuming nitric acid-sulfuric acid mixture may give mixtures of the potentially explosive phthaloyl nitrates or nitrites or their nitro derivatives. Formation of these cmpd may be avoided if nitrating mixture is extensively diluted with sulfuric acid and if a small (1.5 mole equiv) /amount/ of nitric acid is present.
Attempts to follow a published method for nitrating phthalic anhydride in sulfuric acid at 80 to 100 deg C with fuming nitric acid caused an eruptive decomposition to occur after 2 hr delay. The hazard can be eliminated by use of a smaller excess of nitrating acid at 55 to 65 deg C. Acyl nitrates were suggested as a possible cause of the delayed eruption ...
A mixture of /phthalic anhydride/ and anhydrous /copper(II)/ oxide exploded violently on heating.
Mixtures of sodium nitrite and phthalic acid or phthalic anhydride explode violently on heating. A nitrite ester may have been produced.
... Reacts with strong oxidants, strong acids, strong bases and reducing agents ... Attacks many metals in the presence of water.

4.13 Skin, Eye, and Respiratory Irritations: Corrosive. Causes severe eye and skin burns. May be harmful if inhaled. Symptoms of overexposure include ulcer bleeding, upper respiratory irritation, bronchitis, asthma, and dermatitis.
Dust vapor or fumes ... are irritating to eyes ... .
The substance is severely irritating to the eyes, the skin and the respiratory tract ... Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation exposure may cause asthma.

4.14 Safety: Hazard Codes: Xn
Risk Statements: 22-37/38-41-42/43
22:? Harmful if swallowed?
37/38:? Irritating to respiratory system and skin?
41:? Risk of serious damage to eyes?
42/43:? May cause sensitization by inhalation and skin contact
Safety Statements: 23-24/25-26-37/39-46-22
23:? Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)?
24/25:? Avoid contact with skin and eyes?
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
37/39:? Wear suitable gloves and eye/face protection?
46:? If swallowed, seek medical advice immediately and show this container or label?
22:? Do not breathe dust??
RIDADR: 2214
WGK Germany: 1
F: 10-21: Keep under argon. Sensitive to humidity.
HazardClass: 8
PackingGroup: III
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 oxidizing materials. Moderate explosion hazard in the form of dust when exposed to flame.

4.15 Sensitive: Moisture Sensitive

4.16 Specification: ? Phthalic anhydride , with CAS number of 85-44-9, can be called 1,2-Benzenedicarboxylic anhydride ; 1,3-Phthalandione ; 2-Benzofuran-1,3-dione ; Phthalandione ; Phthalanhydride ; Phthalic acid anhydride ; Retarder AK ; Vulkalent B/C ; Sconoc 5 . It is a?white crystalline solid with choking odour.?Phthalic anhydride (CAS NO.85-44-9) is a versatile intermediate in organic chemistry, in part because it is bifunctional and cheaply available. It is widely used in industry for the production of certain dyes. 3、A well-known application of this reactivity is the preparation of the anthroquinone dye quinizarin by reaction with para-chlorophenol followed by hydrolysis of the chloride. It is also used for the manufacture of plasticizers, such as dioctyl phthalate, unsaturated polyester resins, and alkyd resins. Phthalic anhydride reacts with alcohols such as 2-ethylhexanol, and the products are often liquids that, when added to plastics, impart flexibility without adversely affecting the strength of the plastic. Most of these plasticizers are used for poly(vinyl chloride) flexibility. Dioctyl phthalate is a common plasticizer.

4.17 Toxicity: LD50 orally in Rabbit: 1530 mg/kg LD50 dermal Rabbit > 3160 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Serious eye damage, Category 1

Skin sensitization, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

Respiratory sensitization, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage H317 May cause an allergic skin reaction H335 May cause respiratory irritation H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/...
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

1H NMR : 90 MHz in CDCl3

1H NMR : 90 MHz in DMSO-d6

1H NMR : parameter in CDCl3

IR : KBr disc

Mass

7. Synthesis Route

85-44-9Total: 64 Synthesis Route

90-13-1 64 Suppliers

85-44-9 308 Suppliers

117-21-5 67 Suppliers

Literatures:
Angewandte Chemie, , vol. 54, p. 22
Yield: null

91-58-7 42 Suppliers

85-44-9 308 Suppliers

118-45-6 112 Suppliers

Literatures:
Angewandte Chemie, , vol. 54, p. 22
Yield: null

91-20-3 195 Suppliers

85-44-9 308 Suppliers

524-42-5 45 Suppliers

Literatures:
Calderbank Ind. Chemist, 1952 , vol. 28, # 7 p. 291
Yield: null

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8. Other Information

8.0 Merck: 14,7372

8.1 BRN: 118515

8.2 Chemical Properties: white crystalline solid with choking odour

8.3 Chemical Properties: Phthalic Anhydride is moderately flammable, white solid (flake) or a clear, colorless, mobile liquid (molten) Characteristic, acrid, choking odor

8.4 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.

8.5 Definition: ChEBI: The cyclic dicarboxylic anhydride that is the anhydride of phthalic acid.

8.6 Uses: manufacture of phthaleins, phthalates, benzoic acid, synthetic indigo, artificial resins (glyptal).

8.7 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.

8.8 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.

8.9 Reactivity Profile: 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. 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 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 and anhydrous CO2 explode violently if heated [eaflet No. 5, Inst. of Chem., London, 1940].

8.10 Health Hazard: Solid irritates skin and eyes, causing coughing and sneezing. Liquid causes severe thermal burns.

8.11 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.

8.12 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.

8.13 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.

8.14 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.

8.15 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.

8.16 Shipping: UN2214 Phthalic anhydride with＞.05 % maleic anhydride, Hazard class: 8; Labels: 8-Corrosive material.

8.17 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.]

8.18 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.

8.19 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 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.

8.20 Chemical Properties: Phthalic Anhydride is moderately flammable, white solid (flake) or a clear, colorless, mobile liquid (molten) Characteristic, acrid, choking odor. It is very slightly soluble in H2O, soluble in alcohol, and slightly soluble in ether.

8.21 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).

8.22 Definition: ChEBI: Phthalic anhydride is the cyclic dicarboxylic anhydride that is the anhydride of phthalic acid. It has a role as an allergen. It is a cyclic dicarboxylic anhydride and a member of 2-benzofurans.

8.23 Preparation: The most important modifying component used in the manufacture of linear unsaturated polyesters is phthalic anhydride. The anhydride is generally obtained by the oxidation of o-xylene:

The reaction is carried out in the vapour phase by passing a mixture of o-xylene and air over a catalyst such as vanadium pentoxide supported on silica and promoted with titanium dioxide at about 400°C. The exit gases are cooled and the phthalic anhydride is collected and purified by distillation under reduced pressure.

8.24 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

8.25 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.

8.26 Reactivity Profile: 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. 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 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 and anhydrous CO2 explode violently if heated [eaflet No. 5, Inst. of Chem., London, 1940].

8.27 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.

8.28 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.

8.29 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.

8.30 Usage: Phthalic anhydride is used in the preparation of primary amines. It is used as a precursor to prepare anthraquinone, phthalein, rhodamine, phthalocyanine, fluorescein and xanthene dyes. It serves as an important intermediate in the plastics industry, dyes, resins and pigments. It is used as a monomer for synthetic resins such as glyptal, alkyd resins and polyester resins. It plays a vital role in the large-scale production of plasticizers for plastics. Further, it acts as a curing agent for epoxy resins, anti-scaling agents, plating agents, surface treating agents, ion exchange agents, paint additives, adhesives, sealant chemicals and potential antibacterial agent.

8.31 Usage: Phthalic anhydride is used as an intermediate in chemical synthesis and plastics manufacturing.

9. Computational chemical data

Molecular Weight: 148.117g/mol
Molecular Formula: C₈H₄O₃
Compound Is Canonicalized: True
XLogP3-AA: 1.3
Exact Mass: 148.016043985
Monoisotopic Mass: 148.016043985
Complexity: 187
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 43.4
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBwMAAAAAAAAAAAAAAAAAAAASAAAAAwAAAAAAAAAEgBAAAAGgAAAAAADACAmAAwCIAABACIAiDSCAACAAAkAAAIiAEACMgIJjKANRiCMQAkwAEIqYeLyKCOgAAAAAAQAAAAAAAAACAAAAAAAAAAAA==

10. Question & Answer

Applications of Phthalic anhydride Feb 03 2021
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 ch...

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