Phthalic Anhydride

Hazardous Air Pollutants (HAPs)

Corrosives

Phthalate

log Kow = 1.60

1.6

Mild

Characteristic, acrid odor

1.2 at 275 °F 1.53 at 20 °C (solid) (USCG, 1999) - Denser than water; will sink

1.20 (molten); 1.53 (flake)

1.53 g/cm³

1.53 at 68 °F

1.527 @ 4°C

1.53 (Flake) 1.20 (Molten)

White, lustrous needles

Colorless needles; monoclinic or rhombic prisms

White needles from alcohol and benzene

White solid (flake) or a clear colorless liquid (molten)

Decomposes (NTP, 1992)

In water, 6,000 mg/L at 25 °C

In water, 6,200 mg/L at 26 °C; 5,964 mg/L at room temperature

In water, 6,200 to 6,400 mg/L at 20-25 °C

In water, 16,400 mg/L including rapid hydrolysis to phthalic acid

For more Solubility (Complete) data for PHTHALIC ANHYDRIDE (7 total), please visit the HSDB record page.

305 °F (NTP, 1992)

305 °F (152 °C) (Closed cup)

329 °F (Open cup); 305 °F (Closed cup)

152 °C c.c.

305 °F

305 °F

563 °F at 760 mmHg (sublimes) (NTP, 1992)

285.3 °C

Sublimes below the boiling point

284 °C (sublimes)

563 °F

295 °C @760 [mm Hg]

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.4% (14 of 3919) of reports.

Danger

H302 (99.6%): Harmful if swallowed [Warning Acute toxicity, oral]

Chemical: 1,3-Isobenzofurandione

Hazard Traits - Dermatotoxicity; Respiratory Toxicity

1,3-Isobenzofurandione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Isobenzofurandione are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 10-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15845

Phthalic anhydride: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

· Combustible material: may burn but does not ignite readily.

Combustible. Finely dispersed particles form explosive mixtures in air.

Combustible solid

Combustible when exposed to heat or flame.

Solid irritates skin and eyes, causing coughing and sneezing. Liquid causes severe thermal burns. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Exposure to phthalic anhydride may occur during its use as a chemical intermediate in the plastics industry. The acute (short-term) effects from exposure to phthalic anhydride in humans consists of irritation to the eyes, respiratory tract, and skin, but no permanent injury is observed. Chronic (long-term) effects observed in workers exposed to phthalic anhydride included conjunctivitis, rhinitis, rhinoconjunctivitis, bronchitis, and irritation of the skin and mucous membranes of the respiratory tract. Animal studies indicate that chronic exposure to phthalic anhydride vapor causes congestion, irritation, and injury to lung cells. No studies are available on the reproductive, developmental, or carcinogenic effects of phthalic anhydride in humans. EPA has not classified phthalic anhydride for carcinogenicity.

Occupational asthma reported in plastic resin production workers; [Malo] Solid form causes first degree burns on short exposure; [CHRIS] Phthalic anhydride is a skin irritant. [Quick CPC] Workers exhibiting dermal or respiratory symptoms (e.g., rhinitis) may benefit from early intervention to reduce or eliminate further exposure. . . . A number of human studies found that phthalic anhydride exposure can cause or is associated with sensitization, elevated IgE and IgG, occupational asthma (immediate, late or both), rhinitis, conjunctivitis, chronic bronchitis, respiratory irritation, and contact urticaria. It may also cause allergic contact dermatitis. [ACGIH] See ACID ANHYDRIDES.

2214 156

2214 156

European Chemicals Bureau; IUCLID Dataset, Phthalic anhydride (CAS No. 85-44-9) (2000 CD-ROM edition). Description of information on usage patterns, toxicology, and ecological effects submitted by industry to the European Union.[Available from, as of August 22, 2006: http://esis.jrc.ec.europa.eu/]

DHEW/NCI; Bioassay of Phthalic Anhydride for Possible Carcinogenicity (1979) Technical Report Series No. 159 (DHEW Pub No. (NIH) 79-1715)[Available from, as of April 4, 2003: http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/tr159.pdf]

U190; As stipulated in 40 CFR 261.33, when phthalic anhydride, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:

Use water spray, foam, dry powder, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

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.

Chemical stability: Stable under recommended storage conditions.

Keep container tightly closed in a dry and well-ventilated place.

Separated from combustible ... substances ... food and feedstuffs ... Ventilation along the floor ... Well closed.

Store in a cool, dry, well-ventilated location. Separate from acids, alkalies, oxidizing materials, reducing agents, and moisture.

Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.

Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

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.

For more Cleanup Methods (Complete) data for PHTHALIC ANHYDRIDE (9 total), please visit the HSDB record page.

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.

Offer surpls and non-recyclable solutions to a licensed disposal company. Contact 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.

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 °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 °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/

Respiratory

Eyes, skin, respiratory system, liver, kidneys

LC50; Species: Leuciscus idus (orfe); Conditions: static; Concentration: 313 mg/L for 48 hr

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater; static; Concentration: 41400 ug/L (95% confidence limit: 0 to 109100 ug/L) for 96 hr; Effect: population, biomass /active ingredient/

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater; static; Concentration: 78530 ug/L (95% confidence limit: 0 to 1353330 ug/L) for 96 hr; Effect: population, biomass /active ingredient/

EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater; static; Concentration: 147 ug/L (95% confidence limit: 60 to 350 ug/L) for 96 hr; Effect: population, biomass /active ingredient/

For more Ecotoxicity Values (Complete) data for PHTHALIC ANHYDRIDE (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that phthalic anhydride is expected to have very high mobility in soil(SRC). However, phthalic anhydride hydrolyzes rapidly in water with a half-life of about 25 minutes or less at 25 °C(3,4) which suggests that leaching may not be an important fate process(SRC). Volatilization of phthalic anhydride from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-8 atm-cu m/mole(SRC) based upon its vapor pressure, 5.17X10-4 mm Hg(5), and water solubility, 6000 mg/L(6). Hydrolysis in moist soil will also attenuate volatilization(SRC). Phthalic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. Based on the available experimental biodegradation test results, phthalic anhydride can be classified as readily biodegradable(3). However, biodegradation test results may be reflective of biodegradation of phthalic acid which is the hydrolysis product of phthalic anhydride(3,4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that phthalic anhydride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.7X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 5.17X10-4 mm Hg(4), and water solubility, 6000 mg/L(5). Phthalic anhydride hydrolyzes rapidly in water with a half-life of about 25 minutes or less at 25 °C(6,7). Phthalic acid is the hydrolysis product(6). Hydrolysis half-lives may drop to one minute or less depending on buffering agents in the water and pH(6-8). According to a classification scheme(9), an estimated BCF of 5(SRC), from its log Kow of 1.60(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Any potential volatilization or bioconcentration will be attenuated by hydrolysis(SRC). Based on the available experimental biodegradation test results, phthalic anhydride can be classified as readily biodegradable(6). However, biodegradation test results may be reflective of biodegradation of phthalic acid which is the hydrolysis product of phthalic anhydride(6,7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phthalic anhydride, which has a vapor pressure of 5.17X10-4 mm Hg at 25 °C(2), is expected to exist primarily as a vapor in the ambient atmosphere. However, monitoring data(3) and photoreactor studies(4) have found that phthalic anhydride can exist in ambient air in particulate phase. Vapor-phase phthalic anhydride is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 21 days(SRC), calculated from its rate constant of 7.5X10-13 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(5). Particulate-phase phthalic anhydride may be removed from the air by wet and dry deposition(SRC). Phthalic anhydride absorbs at wavelengths >290 nm(6) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

inhalation, ingestion, skin and/or eye contact

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%.

Cough. Sore throat. Wheezing. Shortness of breath.

Redness. Pain.

Redness. Pain. Corneal damage.

Burning sensation. Abdominal pain.

irritation eyes, skin, upper respiratory system; conjunctivitis; nasal ulcer bleeding; bronchitis, bronchial asthma; dermatitis; In Animals: liver, kidney damage

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=85-44-9]

Phthalic anhydride was identified, not quantified, in advanced waste treatment concentrates(1), fly ash from a municipal solid waste incinerator(2) and effluents from two unspecified chemical plants(3). Identified industrial point sources include industrial plants which oxidize xylenes and naphthalene for phthalic anhydride production; gross estimate of discharge 5,000 tons/yr; waste treatment and disposal sources: incineration of industrial refuse and water sludges and slurries from plastic products and other manufacturing processes; leaches from municipal and industrial wastes containing plastics(4). Phthalic anhydride was identified in diesel exhaust(5) and emissions from polyurethane products(6). Phthalic anhydride had 183 occurrences in the Contract Laboratory Program (CLP) analytical results data base for samples from hazardous waste sites(7).

Phthalic anhydride

Respiratory

2 mg/kg-day

U190; As stipulated in 40 CFR 261.33, when phthalic anhydride, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Phthalic anhydride is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Phthalic anhydride is included on this list.

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

The excretion of phthalic anhydride in humans has been investigated in a study where urine samples were collected from nine subjects occupationally exposed to phthalic anhydride, primarily by the inhalation route... Phthalic anhydride is converted to phthalic acid in the presence of water... The concentration of phthalic acid in the urine was found to increase from the pre-shift level to a maximum in the immediate postshift or evening urine sample. The concentration then decreased, with a half-life of approx. 14 hours (no further information on half-life estimation). No evidence was seen of conjugate formation...

The excretion of phthalic anhydride in humans has been investigated in a study where urine samples were collected from nine subjects occupationally exposed to phthalic anhydride, primarily by the inhalation route. Samples were taken pre-shift (7:00 hours) on-shift, post-shift (15:00 hours) and in the evening and the next morning after work day. Airborne phthalic anhydride levels ranged from 0.03 to 10.5 mg/cu m (mean value, MMAD not stated), determined from personal air samples from the worker breathing zone. Urine was also taken from a control group of 22 persons not occupational exposed to phthalic anhydride. Phthalic anhydride is converted to phthalic acid in the presence of water. Phthalic acid concentration in the urine was measured after esterification with methanol by electron capture gas chromatography, and expressed in terms of urinary creatinine. Urine samples were also subjected to acid, alkaline, and enzymatic hydrolysis by beta-glucuronidase or aryl sulphatase. At low atmospheric phthalic anhydride concentrations (mean +/- SD; 0.15 +/- 0.15 mg/cu m, range 0.03 - 0.33 mg/cu m, n=5) the excretion of phthalic acid increased from the pre-shift (7:00 hours) concentration to the post-shift (15:00 hours) concentration and decreased then until the pre-shift concentration was again reached. The pre-shift phthalic acid concentration in the urine (0.49 +/- 0.15 umol/mmol creatinine) were not significantly different from those of occupationally unexposed people (0.34 +/- 0.25 mol/mmol creatinine, range 0.02-0.089 umol/mmol creatinine, n=22). Exposure to higher concentrations of phthalic anhydride in air (1.63 +/- 0.13 mg/cu m, n=2) resulted in a body load of phthalic acid which was not totally cleared overnight, and with pre-shift phthalic acid concentrations in the urine with a mean value three times the mean control value (1.02 +/- 0.25 umol/mmol creatinine). One worker exposed to high concentration of phthalic anhydride (10.2 mg/cu m) had a pre-shift urinary concentration of 4.8 umol of phthalic acid /mmol creatinine; approximately 14 times that of the control group. The concentration of phthalic acid in the urine was found to increase from the pre-shift level to a maximum in the immediate postshift or evening urine sample. The concentration then decreased, with a half-life of approx. 14 hours (no further information on half-life estimation). No evidence was seen of conjugate formation. Thus, workers occupationally exposed to atmospheric phthalic anhydride absorbed the substance with some being excreted in the urine as unconjugated phthalic acid.

Covalently bound radioactivity was found in all tissues of fetuses of CD-1 mouse dams injected ip with 80 mg/kg (14)C-phthalic anhydride on days 11, 12 and 13 of gestation.

Administration of [(14)-C]- or [(3)H]-phthalic anhydride to pregnant rabbits during embryogenesis /resulted in/ bound radioactivity ... found in all tissues examined.

Bound radioactivity was found in the fetuses of mice receiving [(14)C]- phthalic anhydride by the intraperitoneal route, indicating the phthalic anhydride or a metabolite of the substrate may can cross the placenta.

The excretion of phthalic anhydride in humans has been investigated in a study where urine samples were collected from nine subjects occupationally exposed to phthalic anhydride, primarily by the inhalation route. Samples were taken pre-shift (7:00 hours) on-shift, post-shift (15:00 hours) and in the evening and the next morning after work day. Airborne phthalic anhydride levels ranged from 0.03 to 10.5 mg/cu m (mean value, MMAD not stated), determined from personal air samples from the worker breathing zone. Urine was also taken from a control group of 22 persons not occupational exposed to phthalic anhydride. Phthalic anhydride is converted to phthalic acid in the presence of water. Phthalic acid concentration in the urine was measured after esterification with methanol by electron capture gas chromatography, and expressed in terms of urinary creatinine. Urine samples were also subjected to acid, alkaline, and enzymatic hydrolysis by beta-glucuronidase or aryl sulphatase. At low atmospheric phthalic anhydride concentrations (mean +/- SD; 0.15 +/- 0.15 mg/cu m, range 0.03 - 0.33 mg/cu m, n=5) the excretion of phthalic acid increased from the pre-shift (7:00 hours) concentration to the post-shift (15:00 hours) concentration and decreased then until the pre-shift concentration was again reached. The pre-shift phthalic acid concentration in the urine (0.49 +/- 0.15 umol/mmol creatinine) were not significantly different from those of occupationally unexposed people (0.34 +/- 0.25 mol/mmol creatinine, range 0.02-0.089 umol/mmol creatinine, n=22). Exposure to higher concentrations of phthalic anhydride in air (1.63 +/- 0.13 mg/cu m, n=2) resulted in a body load of phthalic acid which was not totally cleared overnight, and with pre-shift phthalic acid concentrations in the urine with a mean value three times the mean control value (1.02 +/- 0.25 umol/mmol creatinine). One worker exposed to high concentration of phthalic anhydride (10.2 mg/cu m) had a pre-shift urinary concentration of 4.8 umol of phthalic acid /mmol creatinine; approximately 14 times that of the control group. The concentration of phthalic acid in the urine was found to increase from the pre-shift level to a maximum in the immediate postshift or evening urine sample. The concentration then decreased, with a half-life of approx. 14 hours (no further information on half-life estimation). No evidence was seen of conjugate formation. Thus, workers occupationally exposed to atmospheric phthalic anhydride absorbed the substance with some being excreted in the urine as unconjugated phthalic acid.

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 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.

Chemical intermediate for various chemical resins, dyes, and pigments; curing agent for epoxy resins; [HSDB] Occupational asthma reported in plastic resin production workers; [Malo] Used to make alkyd resins in the production of paints; Workers may be exposed while welding on painted metals containing alkyd resin with phthalic anhydride hardener; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

Manufacture phthaleins, phthalates, benzoic acid, synthetic indigo, artificial resins (glyptal). Buffer.

Chem int for dioctyl phthalates-eg, di(2-ethylhexyl), other phthalate plasticizers-eg, dibutyl, insect repellents-eg, dimethyl phthalate, unsaturated polyester resins, alkyd resins, dyes and pigments, isatoic anhydride, halogenated phthalic anhydrides, diallyl phthalate, urethane polyester polyols, phenolphthalein; curing agent for epoxy resins.

Rubber retarder

The most troublesome impurity is phthalide (1(3)-isobenzofuranone), which is structurally similar to phthalic anhydride.

Impure phthalic anhydride may contain small amt of maleic anhydride & traces of naphthoquinone, which might augment irritant action.

(1978) 4.18X10+8 G

(1982) 5.05X10+9 G

(1978) 1.83X10+10 G

(1982) 8.63X10+8 G

2023: 400,000,000 - <550,000,000 lb

(1978) 4.44X10+11 G

(1982) 3.14X10+11 G

(1988) 9.99X10+8 LB

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4706]

For more U.S. Production (Complete) data for PHTHALIC ANHYDRIDE (7 total), please visit the HSDB record page.

CHEM INT FOR: PHTHALATE PLACTICIZERS, 53%; UNSATURATED POLYESTER RESINS, 22%; ALKYD RESINS, 19%; OTHER USES (EG, CHEM INT FOR DYES, RUBBER RETARDER), 6% (1983)

End use pattern: phthalate plasticizers, 50%; unsaturated polyesters, 25%; alkyd resins, 15%; miscellaneous, 10% (1985)

CHEMICAL PROFILE: Phthalic Anhydride. Plasticizers, 48%; polyester resins, 23%; alkyd resins, 19%; miscellaneous, 5%; exports, 5%.

CHEMICAL PROFILE: Phthalic anhydride. Demand: 1988: 1,050 million lb; 1989: 950 million lb; 1993 /projected/: 1,190 million lb. (Includes exports, but not imports, which totaled 30 million lb last year.)

Today 60% of production is used as a plasticizer in vinyl chloride polymerization. About 30% of output is used for the production of saturated & unsaturated polyester resins, for pesticides & as constituents of certain essences & perfumes. The remaining 10% is employed in the production of alkyd resins used in paints & lacquers, of phthalocyanine dyes & also for the preparation of benzoic acid.

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 °C.

/Commercial production by/ ... gas-phase oxidation of naphthalene or o-xylene in an air stream with vanadium oxide as catalyst.

Grade: Pure, technical.

Grades or purity: flake, molten; commercial: 99.8% purity.

Rubber Product Manufacturing

1,3-Isobenzofurandione: ACTIVE