Phthalic acid
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Phthalic acid
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CAS No:
88-99-3
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Formula:
C8H6O4
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Chemical Name:
Phthalic acid
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Synonyms:
1,2-Benzenedicarboxylic acid;Phthalic acid;o-Benzenedicarboxylic acid;o-Dicarboxybenzene;Sunftal 20;o-Carboxybenzoic acid;M 2;NSC 5348;4401-64-3
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CAS No:
Description
Phthalic acid is the final common metabolite of phthalic acid esters (PAEs). Phthalic acid can be used for the synthesis of synthetic agents, such as isophthalic acid (IPA), and terephthalic acid (TPA). Phthalic acid has applications in the preparation of phthalate ester plasticizers[1].
Phthalic acid appears as white crystals or fine white powder. (NTP, 1992)|Solid|CRYSTALLINE POWDER.|White crystals or a fine white powder.
Phthalic acid appears as white crystals or fine white powder. (NTP, 1992)|Phthalic acid is a benzenedicarboxylic acid cosisting of two carboxy groups at ortho positions. It has a role as a human xenobiotic metabolite. It is a conjugate acid of a phthalate(1-).
Phthalic acid Basic Attributes
166.13
166.13
608199
201-873-2
6O7F7IX66E
0768
5348
DTXSID8021484
Colorless crystals|Plates from water
29173980
Characteristics
74.6
0.7
White Powder
1.593 g/cm3 @ Temp: 15 °C
191 °C (decomp)
Decomposes
168 °C
1.618
H2O: 7 g/L (25 ºC);methanol: 0.1 g/mL, clear
Store below +30°C.
7.8 hPa (191 °C)
Relative vapour density (air = 1): 5.7
LD50 orally in rats: 7.9 g/kg (Shaffer)
Forms anhydride (dust explosion hazard).
2.76(at 25 °C)
Henry's Law constant = 2.1X10-11 atm-cu m/mole at 25 °C (est)
pKa1 = 2.76; pKa2 = 4.92 at 25 °C
...When rapidly heated, forming phthalic anhydride and water|Specific heat = 1138 J/kg-K at 300 K|Specific heat of solid (0-99 °C) 1.214 J/g-K|Heat of fusion = 315.3 J/g|For more Other Experimental Properties (Complete) data for PHTHALIC ACID (6 total), please visit the HSDB record page.
Insoluble in water.
Acids, Carboxylic
PHTHALIC ACID is a carboxylic acid. This chemical is sensitive to exposure to extreme heat. This compound reacts violently with nitric acid. It is incompatible with sodium nitrite. It is also incompatible with oxidizers. (NTP, 1992).
19657.03 J/g
Dust explosion possible if in powder or granular form, mixed with air.
Critical temperature = 800.00 K; Critical pressure = 3.9500X10+6 Pa
Safety Information
NONH for all modes of transport
1
36/37/38
26-36-37/39
TH9625000
Xi
Stable. Combustible. Incompatible with strong oxidizing agents.
P305 + P351 + P338
H315-H319-H335
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Mixtures of sodium nitrite and phthalic acid or phthalic anhydride explode violently on heating. A nitrite ester may have been produced.|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.
o-Phthalic acid is an indirect food additive for use as a component of adhesives.
This chemical is combustible. (NTP, 1992)|Combustible. Finely dispersed particles form explosive mixtures in air.
|Warning|H315 (96.4%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 142 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Protective gloves. Safety spectacles ... Extra personal protection: P1 filter respirator for inert particles.|... Skin contact is to be avoided... Suitable clothing such as rubber hand protection, is recommended.
Combustible when heated.
Finely dispersed particles form explosive mixtures in air.|Forms anhydride (dust explosion hazard).
Powder, water spray, foam, carbon dioxide.
Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.
Sweep spilled substance into containers; if appropriate, moisten first to prevent dusting (extra personal protection: P1 filter respirator for inert particles).
Good local & general ventilation are required where phthalic acid is handled.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|NO open flames ... Prevent deposition of dust; closed system, dust explosion-proof electrical equipment and lighting ... PREVENT DISPERSION OF DUST ... Do not eat, drink, or smoke during work.
ACUTE ... SYMPTOMS: Inhalation--cough, sore throat. Skin--redness. Eyes--redness, pain ... The substance irritates the eyes, the skin and the respiratory tract.|A skin and mucous membrane irritant.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.
A nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
The substance is irritating to the eyes, skin and respiratory tract.
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
PREVENT DISPERSION OF DUST!
Use local exhaust.
Protective gloves.
Wear safety spectacles.
| 1 - Materials that, under emergency conditions, can cause significant irritation.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.
In a comprehensive survey of wastewater from 4000 industrial and publicly owned treatment works (POTWs) sponsored by the Effluent Guidelines Division of the U.S. EPA, phthalic acid was identified in discharges of the following industrial categories (positive occurrences, median concn in ppb): leather tanning (3; 8.8), nonferrous metals (5; 5.0), paint and ink (6; 69.8), printing and publishing (1; 126.2), organics and plastics (5; 269.5), textile mills (3; 46.1), plastics and synthetics (6; 78.3), auto and other laundries (3; 22.9), pesticides manufacture (2; 2986.4), explosives (18; 29.5), foundries (7; 11.8), aluminum (3; 7.4), electronics (6; 60.6), organic chemicals (19; 32.3), mechanical products (2; 11.3), publicly owned treatment works (4; 3.3)(1). The highest effluent concns, and the only ones >1 ppm were 5969 ppb and 4761 ppb in the pesticides manufacture and organics and plastics industries(1). Effluent samples from the Kimberly-Clark Terrace Bay Mill in 1981 contained 0.16 and 0.56 mg/L of phthalic acid(2). Phthalic acid was found in effluent from advanced wastewater treatment plants in Lake Tahoe CA, Orange County CA, Dallas TX, and Washington DC (Blue Plains plant)(3). Phthalic acid was found at concns of 566.9 ug/L of fuel burned from motor vehicle traffic in a Los Angeles roadway tunnel(4). Phthalic acid was found in automobile exhaust: 1982 Toyota Corolla 15 nmol/cu m; 1971 Mercedes Benz 214 nmol/cu m(5).|/detected/ in primary sewage plant effluent: 2 mg/L
SOIL: The concn of phthalic acid in soil (n=2) in Los Angeles was 47.9-52.5 nmol/g(1). Soil from Prince Edward Island, Canada: 0.03% of total organic matter(2).|SEDIMENT: The concn of phthalic acid in bog sediment from the Sierra Nevada mountains was 75 nmol/g(1). Thunder Bay, Lake Superior sediment (11 stations) <0.005 - 1 mg/kg, 0.3 mg/kg, median(1).
URBAN/SUBURBAN: The ambient annual average concn of phthalic acid in fine particle organic compounds at four sites on a west to east trajectory, West Los Angeles, downtown Los Angeles, Pasadena, and Rubidouc for 1982 were 60.6, 60.0, 55.7 and 53.5 ng/cu m, respectively(1). 24-Hr samples were collected at 6 day intervals over the year(1). Concns were lowest from Sept to January and highest in February(1). The concn of phthalic acid at a background site on San Nicolas Island, west of Los Angeles, averaged <0.03 ng/cu m from July to December(1). In a study of long-term transport of photochemical air pollution from coastal areas in Japan with large emission sources to inland mountains, the resulting mean concns of phthalic acid in airborne aerosols in a plume at Takasaki (July 26-31, 1986) and Karuizawa (July 29-31, 1986) were 22.1 and 19.5 ng/cu m, respectively(2). Phthalic acid was identified in airborne particulate matter from a suburban area 60 km northeast of Tokyo, Japan in April 1985(3). The concn range of phthalic acid in aerosol samples (n=21) collected from the spring of 1988 to the winter of 1989 in Tokyo, Japan was 4.9-30 ng/cu m(4).|URBAN/SUBURBAN: Monitoring of phthalic acid in Los Angeles, CA in 1984: West Los Angeles (n=8) 0.12-1.76 nmol/cu m; downtown (n=2) 1.38-1.95 nmol/cu m; greenhouse (n=2) 0.15-0.55 nmol/cu m(1). Atmospheric concns of phthalic acid were measured in the southeastern United States from April 1999 to January 2000; North Birmingham, Al 5.88 ng/cu m, Jefferson Street, Atlanta, GA 5.98 ng/cu m, Gulfport, MS 2.32 ng/cu m, Pensacola, FL 2.87 ng/cu m and OLF#8, FL 2.07 ng/cu m(3). Tokyo aerosol concns: Feb 1992 (n=2): 130 ng/cu m, 85 ng/cu m; July 1992: (n=2) 135 ng/cu m, 157 ng/cu m(2). Phthalic acid was the third most abundant diacid in Tokyo, Japan aerosols(2). A study of water-soluble organic compounds in urban atmospheric particles from Kobe City, Japan found that phthalic acid was detected in the 0.43-1.1 um size fraction with concentrations of <2.80 ng/cu m from Aug 3-14, 1998, 3.03 ng/cu m from Oct 7-19, 1998, 4.20 ng/cu m from Mar 1-26, 1999 and 3.64 ng/cu m from Apr 27- May 17, 1999(4).|URBAN/SUBURBAN: Wintertime atmospheric concentrations of phthalic acid were measured in Fresno, CA as 9.16 ng/cu m for the sampling period Dec 26-28, 1995 and 9.09 ng/cu m for the sampling period of Jan 4-6, 1996(1). Wintertime concentrations were also measured in Bakersfield, CA as 6.78 ng/cu m for the sampling period Dec 26-28, 1995 and 13.1 ng/cu m for the sampling period of Jan 4-6, 1996(9). Five urban sites were analyzed for phthalic acid in southern California in 1995; Long Beach 3.51 ng/cu m, Mira Loma 3.19 ng/cu m, Riverside 4.51 ng/cu m, San Dimas 4.54 ng/cu m and Upland 4.07 ng/cu m(2). Continental background aerosol levels of phthalic acid were measured in Tokyo, Japan, Vienna, Austria and Los Angeles, CA at 135 ng/cu m, 18 ng/cu m and 60 ng/cu m, respectively(3). Samples taken from four sites in the Los Angeles, CA area September 8-9, 1993 found an average of 80.2 ng/cu m of phthalic acid in atmospheric fine particulates(4).|INDOOR AIR: Phthalic acid was identified in particulate matter in air in Chinese homes burning smokeless coal(1).|RURAL/REMOTE: Atmospheric concentrations of phthalic acid were measured in the southeastern United States from April 1999 to January 2000; Centreville, AL 5.94 ng/cu m, Yorkville, GA 3.59 ng/cu m and Oak Grove, MS 2.54 ng/cu m(1). Wintertime atmospheric concentrations of phthalic acid were measured in Kern Wildlife Refuge, CA as 4.71 ng/cu m for the sampling period Dec 26-28, 1995 and 5.43 ng/cu m for the sampling period of Jan 4-6, 1996(2). Four rural sites were analyzed for phthalic acid in southern California in 1995; Atascadere 4.13 ng/cu m, Lake Elsinore 3.01 ng/cu m, Lompoc 1.39 ng/cu m and Santa Maria 1.97 ng/cu m(3). Two mountain sites and one desert site were also analyzed; Alpine 4.6 ng/cu m, Lake Arrowhead 8.17 ng/cu m and Lancaster 2.99 ng/cu m(3). Continental background aerosol levels of phthalic acid were measured in South Africa, Salzburg, Austria and Antarctica at 3.3 ng/cu m, 3.3 ng/cu m and 1.7 ng/cu m, respectively(4). Concentrations of phthalic acid were measured in arctic aerosols from July of 1987 to June of 1988 ranging from <0.005 ng/cu m to 5.8 ng/cu m(5).
The concn of phthalic acid in Los Angeles dust (n=2) was 326-621 nmol/g(1). Phthalic acid was found in tobacco at concn of 0.35 mg/100 g tobacco smoked(2). Phthalic acid was measured with 8 other aromatic acids in the organic film on glass windows(3). The concn decreased from urban to rural areas on the outside of windows and the inside/outside concn ratio for phthalic acid was higher on windows in suburban and rural sites tested suggesting the importance of indoor sources(3).
Toxicity
LD50 Mouse ip 550 mg/kg|LD50 Mouse oral 2,530 mg/kg|LD50 Rat oral 7.9 g/kg
Phthalic acid in soil may originate from lignin-type organic matter (phenols) which may be converted to aromatic diacids by microbial action(1). Phthalic acid has been found in Russian shale, bacteria, fungus, and Lily of the Valley oil (trace)(2).
Phthalic acid's use in the production of dyes, phenolphthalein, phthalimide, anthranilic acid, synthetic perfumes and laboratory reagents(1) may result in its release to the environment through various waste streams.
TERRESTRIAL FATE: Based on a classification scheme(1), experimental Koc values of 2 to 31(2), indicate that phthalic acid is expected to have very high mobility in soil(SRC). Volatilization of phthalic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2X10-11 atm-cu derived from its vapor pressure, 6.36X10-7 mm Hg(3), and water solubility, 6965 mg/L(4). Phthalic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Phthalic acid rapidly degraded in Chalmers soil (1.96% organic carbon, pH 6.0); 100% decomposition was obtained after 53 days(5).|TERRESTRIAL FATE: 14C-Phthalic acid (0.6-600 ppm) was added to the upper 15 cm of Norfolk sandy loam soil in 21 cm high pots and planted with wheat/corn or soybeans/fescue in greenhouse studies(1). The average half-life of phthalic acid (assuming a linear decay) was 37 days for all plantings and application rates. A balance sheet indicated that an average of 5.7% of the originally applied 14C was recovered from soil and plants at the end of the experiment (80 days); most of the phthalic acid was lost through volatilization or decomposition(1). A study was conducted at a plant site where an industrial waste from a terphthalic acid manufacturing facility was injected into the subsurface (259-305 m)(2). While phthalic acid was present at an avg concn of 76 mg/L in the injected waste, phthalic acid was not present in 3 monitoring wells, 2-4 years post injection(2). When phthalic acid was applied at 448,144 kg/ha to field plots in Muskegon City, MI and tilled to 6 inches within 5 days, the 3 plot average in the 0-6 inch layer was 557 ug/kg after 5 days, 424 ug/kg after 122 days and 0 ug/kg after 241 days(3). No phthalic acid was detected in the 9-15 inch core at any of the sampling times(3). No phthalic acid was present in the soil prior to application(3).|AQUATIC FATE: Based on a classification scheme(1), experimental Koc values of 2 and 31(2), indicate that phthalic acid 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 2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 6.36X10-7 mm Hg(4), and water solubility, 6965 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Phthalic acid completely disappeared from Mississippi River water in 2.5 to 5 wk at concns of 12.5 and 50 mg/L, respectively(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phthalic acid, which has a vapor pressure of 6.36X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phthalic acid 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 13 days(SRC), calculated from its rate constant of 1.24X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase phthalic acid may be removed from the air by wet or dry deposition(SRC). Due to its high water solubility and polar nature, phthalic acid is associated with water droplets(4) in the atmosphere and effectively scavenged by rain(5). Experiments suggest that diacids, which mostly exist as particles (aerosols) in the atmosphere, are removed more efficiently during wet precipitation than most water soluble compounds(5).
The rate constant for the vapor-phase reaction of phthalic acid with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Rate constants for photochemical degradation of phthalic acid were measured in river water at 3.06X10-5/sec and sea water at 2.01X10-5/sec(2), corresponding to half-lives of 6.29 hrs and 6.78 hrs, respectively(SRC).
An estimated BCF of 3 was calculated for phthalic acid(SRC), using a log Kow of 0.73(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).|In greenhouse studies in which 14C-phthalic acid (0.6-600 ppm) was applied to soil planted with wheat/corn and soybeans/fescue, the mean bioaccumulation ratios for total 14C were 0.003 for plants and 0.0005 for seeds(1). TLC analysis showed that the percent of extractable 14C in the form of phthalic acid was 4.5% for corn, 5.2% for fescue, 9.2% for mature wheat, 46.7% for wheat seed, and 15.3% for mature soybean plants(1). This study demonstrated the relatively low potential for accumulation of phthalic acid in crops(1).
11.75 L/kg|The Koc values were determined for an acidic forest soil (Podzol, 4.85% organic carbon, pH 2.8), an agricultural soil (Alfisol, 1.25% organic carbon, pH 6.7) and a sublimnic soil (sediment from Lake Constance, Germany, 1.58% organic carbon, pH 7.1) as 31, 2 and 2, respectively(1). According to a classification scheme(2), these Koc values suggest that phthalic acid is expected to have very high mobility in soil. Phthalic acid adsorbs strongly to aluminum and iron oxides via a surface ligand exchange reaction(3). Adsorptivity is sensitive to pH; for aluminum oxide the fraction absorbed is >0.8 below pH 6 and falls below 0.1 above pH 7.5(3).
The Henry's Law constant for phthalic acid is estimated as 2X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 6.36X10-7 mm Hg(1), and water solubility, 6965 mg/L(2). This Henry's Law constant indicates that phthalic acid is expected to be essentially nonvolatile from water surfaces(3). Phthalic acid's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). Phthalic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
DRINKING WATER: Phthalic acid was found in drinking water concentrates from Cincinnati OH, New Orleans LA, Philadelphia PA, Ottuma IA, and Seattle WA(1). The source of water for Seattle was a pristine stream; rivers were the source of water for the other cities(1).|SURFACE WATER: Phthalic acid was not detected in Nipigon Bay or Nipigon River, Ontario, Canada; both are in the Lake Superior basin(1).|RAIN/SNOW: Phthalic acid concentrations in Tokyo, Japan reported as time series concns (ug/L) were: snow/cleet (3/18/92) 4.07, 4.07, 2.25; rain (6/30/92) 4.07, 8.10, 0.78, 0.38; rain (8/11/92) 30.7, 24.6(1). Phthalic acid was detected in precipitation in Norway(2). Less than 0.1 umol/75 cm of rain was found in precipitation in rural Hubbard Brook, NH, and Ithaca, NY(2). Phthalic acid was measured in 13 rain events at concns of 0.04 to 1.87 uM, and three snow events at concns of 0.035 to 0.047 uM(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 19,695 workers (2862 of these are female) are potentially exposed to phthalic acid in the US(1). Occupational exposure to phthalic acid may occur through dermal contact with this compound at workplaces where phthalic acid is produced as a by product(SRC). Monitoring data indicate that the general population may be exposed to phthalic acid via inhalation of ambient air, ingestion of drinking water, and dermal contact with products containing phthalic acid(SRC).
Drug Information
Probably excreted as phthalic acid. /From table/
Yields 4,5-dihydroxyphthalic acid in Pseudomonas. /FROM TABLE/|Dose effects of di(2-ethylhexyl)phthalate distribution, excretion, and binding to macromolecules were studied in rodents. The urinary di(2-ethylhexyl)phthalate metabolite profile was similar for all doses, except that free phthalic acid was 6 times greater on days 3 and 10 at the highest compared to the lowest dose.|The metabolism of di-(5-hexenyl)phthalate and di-(9-decenyl)phthalate was investigated in rats. Male CD rats received two oral doses of 3 to 12 uM/kg radiolabeled or unlabeled di-(5-hexenyl)phthalate and di-(decenyl)phthalate in cottonseed oil 24 hr apart. One third of the radioactivity was found in the urine. The metabolites were identified as mono-5-hexenyl-phthalate. Mono-5-hexenyl-phthalate comprised 21% of the total urinary phthalates while 5-hexenyl-phthalate glucuronide amounted to 13.2% and free 5-hexenyl-phthalate to 7.8%. In contrast no metabolites of di-(9-decenyl)phthalate were excreted as glucuronide conjugates and only a trace of free phthalic acid was detected although 40 to 50% of the compound was recovered in the urine. The distribution of the metabolic phthalates indicated a different metabolic pathway for di-(9-decenyl)phthalate and di-(5-hexenyl)phthalate. /It was/ concluded that the chemically reactive epoxide metabolite of phthalate with unsaturated side chains may play a role in the acute toxicity of di-(5-hexenyl)phthalate and di-(9-decenyl)phthalate.|Phthalate grown cells readily oxidized dibutylphthalate, phthalate, 3,4-dihydroxyphthalate and protocatechuate. Phthalate-3,4-dioxygenase (and possibly the dihydrodiol dehydrogenase) was induced by phthalate or a metabolite and subsequent enzymes were inducible by protocatechuate or a subsequent metabolic product. During growth at 37 °C, strain 12B gave clones at high frequency that had lost the ability to grow with phthalate esters.|For more Metabolism/Metabolites (Complete) data for PHTHALIC ACID (6 total), please visit the HSDB record page.
Although it is well established that high dose administration of di(2-ethylhexyl)phthalate and its monoester metabolite induces severe testicular atrophy in rats the mechanisms of this testicular injury Is not clear. The present experiment was undertaken to examine the effects of di(2-ethylhexyl) phthalate and mono(2-ethylhexyl)phthalate on mitochondrial functions of rat testis. Di(2-ethylhexyl)phthalate and di-n-octyl phthalate, a di(2-ethylhexyl) phthalate isomer which causes less severe testicular injury did not inhibit the state 3 oxygen consumption up to 0.65 umol/mL in vitro. On the other hand, mono(2-ethylhexyl)phthalate and mono-n-octyl phthalate a metabolite of di-n-octyl phthalate inhibited the state 3 oxygen-consumption down to a concentration of 0.065 amble/mL. Testicular mitochondrial respiratory functions of rats administered 2 g/kg di(2-ethylhexyl) phthalate were lower than those of control or di-n-octyl phthalate treated rats. These differences were verified by characteristics of pharmacokinetic parameters and testicular concentrations of mono(2-ethylhexyl)phthalate and mono-n-octyl phthalate. It nay be suggested that a possible mechanism of testicular atrophy induced by di(2-ethylhexyl) phthalate may be due to direct inhibition by mono(2-ethylhexyl)phthalate (and partially di(2-ethylhexyl)phthalate) of the respiratory functions of Sertoli cell mitochondria in rat testis.|... phthalic acid and nonylphenol stimulated PXR-mediated transcription at concentrations comparable to those at which they activate estrogen receptor-mediated transcription using a transient reporter gene expression assay in COS-7 cells.
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes, and respiratory passages. In high concentrations, it can cause narcosis. ACUTE/CHRONIC HAZARDS: This compound is an irritant of the skin, eyes, mucous membranes, and respiratory tract. It is narcotic in high concentrations. When heated, it decomposes to a compound which in the form of dust is an explosion hazard. Hazardous decomposition products include carbon oxides. (NTP, 1992)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest.
Rinse and then wash skin with water and soap.
Rinse with plenty of water for several minutes (remove contact lenses if easily possible).
Inhalation Exposure: Fresh air, rest. Skin Exposure: Remove contaminated clothes. Rinse and then wash skin with water and soap. Eye exposure: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. Ingestion: Rinse mouth.
/SIGNS AND SYMPTOMS/ There have been reports of conjunctivitis, bloody nasal excreta, atrophy of nasal mucosa, hoarseness, cough and bronchitis in workers employed on the production of phthalic acid and anhydride.|/SIGNS AND SYMPTOMS/ ACUTE ... SYMPTOMS: Inhalation--cough, sore throat. Skin--redness. Eyes--redness, pain.|/CASE REPORTS/ ... A factory worker has been in contact with raw tributyl tin phthalate on one leg. Soon after taking a hot-water bath, he developed severely painful erythema on this leg. Patch tests and chemical analysis revealed that hot water hydrolyzed tributyl tin phthalate and produced concentrated phthalic acid.|/EPIDEMIOLOGY STUDIES/ A large population based case control study evaluated occupational exposures in 1,098 Danish males diagnosed with multiple myeloma from 1970 to 1984 and in 4,169 age and gender matched controls alive at the time of case diagnosis. Associations with phthalates persisted, but were inconsistent with duration and probability of exposure. /Phthalates/|/OTHER TOXICITY INFORMATION/ The rapid proliferation of complex plastic polymers and resins has led to a marked incr of work induced asthma due to low molecular weight agents. Phthalates are frequently used in the manufacture of epoxy resins, plasticizers, adhesives and a wide variety of other materials. They have recently been identified as an important irritant and immunogen of at least four occupational respiratory syndromes, ie, asthma/rhinitis, late respiratory systemic syndrome,pulmonary disease-anemia syndrome, and an irritant reaction. /Phthalates/
disodium phthalate
Cough. Sore throat.
Redness.
Redness.
Phthalic acid Use and Manufacturing
By hydrolysis of phthalic anhydride.
Organic reagent used to synthesize phthalates.
This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1972) PROBABLY GREATER THAN 4.54X10+5 G|(1975) PROBABLY GREATER THAN 4.54X10+5 G|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3112]
Grade: Technical, reagent.|Typical assay (by titration) 99.5%/from sole US bulk producer/
1,2-Benzenedicarboxylic acid: ACTIVE|o-Phthalic acid is seldom employed, since its anhydride is easier to use.|Phthalic anhydride is the principal commercial form of phthalic acid and it is presently manufactured by catalytic air oxidation of o-xylene or naphthalene.|Formed as a byproduct in the manufacture of phthalic anhydride.|Industrially unimportant.
Method for determination of phthalic acid using butyl hydrogen phthalate as internal std for determination of contaminants in iv solution stored polyvinyl chloride bags. Determination made by using GC-single ion monitoring mass spectrometry.
Method is presented for determination of phthalic acid in anticoagulant solution in whole blood using reverse phase high pressure liquid chromatography.
Transformation products|Environmental transformation -> Pesticide transformation products (metabolite, successor)|METABOLITES
Phthalic acid is a known environmental transformation product of folpet.|Phthalic acid is a known environmental transformation product of Acequinocyl, Dithianon, Folpet, Napropamide, Phosmet, and Picoxystrobin.
Computed Properties
Molecular Weight:166.13
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:166.02660867
Monoisotopic Mass:166.02660867
Topological Polar Surface Area:74.6
Heavy Atom Count:12
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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