Pyromellitic dianhydride
89-32-7O=c1oc(=O)c2cc3c(=O)oc(=O)c3cc12ANSXAPJVJOKRDJ-UHFFFAOYSA-NSee also: Polyester-10 (monomer of).
89-32-7DTXSID1026536CHEMBL31821401.68 g/cu cm
1.68 g/cm³
1.68 @25 °C
Soluble in some organic solvents
In water, 130 mg/L @ 25 °C /Estimated/
Solubility in water: reaction
397-400 °C
397-400 °C
286 °C
287 °C
0.0000048 [mmHg]
4.8X10-6 mm Hg @ 25 °C /Estimated/
0.0000048 [mm Hg] @25 °C
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Danger
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P354+P338, P317, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P354+P338, P317, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Chemical: 1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone
Hazard Traits - Respiratory Toxicity
1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone 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)
REACH registered substance: Benzene-1,2:4,5-tetracarboxylic dianhydride (EC: 201-898-9)
Pyromellitic dianhydride: Does not have an individual approval but may be used under an appropriate group standard
A skin irritant; [Hawley] Produces the acid on reaction with water; A skin, eye, and respiratory tract irritant; Heavy exposure may cause pulmonary hemorrhage; May cause skin sensitization and asthma; [ICSC] A mild skin sensitizer in guinea pigs; Acute exposure produces CNS depression in animals; Changes in various enzyme activity (cholinesterase, ALT, AST, cytochrome oxidase, etc.) observed in female mice administered 4.4 and 8.8 mg/kg for six months; [HSDB] An irritant that may cause serious eye injury; May cause sensitization by skin contact and inhalation; [Alfa Aesar MSDS] See ACID ANHYDRIDES.
...Acid anhydrides are low-molecular weight, reactive chemicals that can conjugate to human proteins, rendering the chemical-protein complex immunogenic. The major clinical problem in exposed workers appears to be immune sensitization, which can induce any of three clinical syndromes-- asthma-rhinitis, /late respiratory systemic syndrome/, or /pulmonary disease anemia/. /Acid anhydrides/
Occupational asthma reported in workers using epoxy resin adhesives; [Malo] Used as a curing agent for epoxy resins (high-temperature laminates, molds, and coatings), cross-linking agent for epoxy plasticizers in vinyls and alkyd resins, and intermediate for pyromellitic acid; [Hawley]
Working with Glues and Adhesives [Category: Other]
Curing agent for epoxy resins used in high temperature laminates, molds, coatings; crosslinking agent for epoxy plasticizers in vinyls, alkyd resins; intermediate for pyromellitic acid.
Used in the manufacture of aromatic polyamides (synthetic fibers manufacture) and plasticizers.
The oxidation of durene yields pyromellitic acid or pyromellitic dianhydride directly. The oxidation can be carried out with dilute nitric acid in solution, with air and catalyst either in the vapor phase over a solid vanadium pentoxide-based catalyst or in the liquid phase with a soluble catalyst system based on cobalt, manganese, and bromine.
Pyromellitic dianhydride is ... made from pseudocumene by carbonylation to 2,4,5-trimethylbenzaldehyde using HF-BF3 followed by oxidation to pyromellitic acid.
Oxidation of durene, either in wet process by nitric acid or a dichromate, or as direct air oxidation with catalyst.
読み込み中…
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
FCS -> FDA Inventory of Effective Food Contact Substance (FCS) Notifications
Large Crystals; Dry Powder
White hygroscopic solid; [ICSC] White or off-white powder; [Alfa Aesar MSDS]
WHITE HYGROSCOPIC CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.
化学的特性White powder. Soluble in some organic solvents; hydrolyzes to the acid when exposed to moisture.
化学性质水トリメリト酸同様反応性が高く,耐熱性,耐薬品性に優れている。
Skin Sens. 1 (100%)
Eye damage - category 1
Serious eye damage/eye irritation - Category 1
Skin corrosion/irritation - Category 2
Eye Dam. 1
The physiological effects generally resemble those of the corresponding acids, but they are more potent eye irritants in the vapor phase, and may produce chronic conjunctivitis. They are slowly hydrolyzed on contact with body tissue and may occasionally cause sensitization. /acid anhydrides/
The substance is irritating to the eyes, the skin and the respiratory tract. Exposure at high levels may result in pulmonary hemorrhage.
Fresh air, rest. Half-upright position. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
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.
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.
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.
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.
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.
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 178(SRC), determined from a structure estimation method(2), indicates that pyromellitic dianhydride is expected to have moderate mobility in soil(SRC). Volatilization of pyromellitic dianhydride from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.5X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Pyromellitic dianhydride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-6 mm Hg(SRC), determined from a fragment constant method(4). No biodegradation data for pyromellitic dianhydride were located(SRC); however, this compound is expected to hydrolyze in moist environments including soils producing the monohydride and subsequently pyromellitic acid(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 178(SRC), determined from a structure estimation method(2), indicates that pyromellitic dianhydride is 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 7.5X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 9(SRC), from an estimated log Kow of 2.14(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation data for pyromellitic dianhydride were located(SRC); however, this compound is expected to hydrolyze in water producing the monohydride and subsequently pyromellitic acid(8). The hydrolysis half-life of pyromellitic dianhydride at pH 8 is estimated as about 9 days using an estimation method based on perturbed molecular orbital theory and linear free energy relationship (LFER) methods(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyromellitic dianhydride, which has an estimated vapor pressure of 4.8X10-6 mm Hg at 25 °C (SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase pyromellitic dianhydride 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 56 days(SRC), calculated from its rate constant of 2.9X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Pyromellitic dianhydride is a hygroscopic substance that undergoes hydrolysis when contacted by moisture in the atmosphere resulting in the formation of pyromellitic acid(4). Unreacted particulate-phase pyromellitic dianhydride may be removed from the air by wet and dry deposition(SRC). Pyromellitic dianhydride absorbs light greater than 290 nm and is susceptible to direct photolysis in the environment(5), but the kinetics of this reaction are not known.
Cough. Sore throat. Wheezing. Shortness of breath.
Redness. Burning sensation.
Redness. Pain. Blurred vision.
Burning sensation.
Using a structure estimation method based on molecular connectivity indices(1), the Koc for pyromellitic dianhydride can be estimated to be 178(SRC). According to a classification scheme(2), this estimated Koc value suggests that pyromellitic dianhydride is expected to have moderate mobility in soil(SRC).
/HUMAN EXPOSURE STUDIES/ ...Pyromellitic dianhydride... /has/ been reported to cause occupational immune lung disease (OILD).
/HUMAN EXPOSURE STUDIES/ The most common adverse health effects of the acid anhydrides are noncardiac pulmonary edema, immune sensitization, and irritation of mucous membranes and skin. Reports of the irritant effects and pulmonary edema have been extensive; some of the reports of pulmonary edema, pulmonary hemorrhage, and chemical pneumonitis may actually represent immune sensitization that was not evaluated. Immune sensitization, which has been studied only in the last 15 years, is probably the most important problem clinically. The first cases were probably reported in the 1940s, but there was no accompanying immunologic investigation. /Acid anhydrides/
/CASE REPORTS/ A 17-yr-old man was occupationally exposed to pyromellitic acid dianhydride dust during the production of epoxy resin in a chemical factory. He was clinically diagnosed as having acute hemorrhagic alveolitis associated with anemia. The serologic analysis revealed a high concentration of IgG antibodies against pyromellitic acid dianhydride-treated human serum albumin (PMDA-HSA). Immunoblotting with PMDA-treated human serum as antigen and the patient's serum as the first antibody showed that additional PMDA-modified serum proteins other than HSA were recognized by the patient's IgG antibodies in the higher mol. mass range (>67 kDa). No specific IgG could be detected against other anhydride conjugates (maleic acid, MA; phthalic acid, PA) with the exception of a reaction with the trimellitic acid anhydride-conjugated HSA (TMA-HSA). No specific IgE antibodies could be detected against any of the above mentioned antigens, but immunoblotting of the patient's serum indicated IgG4-type autoantibodies against in vitro PMDA-treated Ig molecules of normal serum proteins.
/CASE REPORTS/ Seven workers using an epoxy adhesive cured with pyromellitic dianhydride were studied. Workers both mixed and used the adhesive. Each completed a questionnaire about previous respiratory symptoms, family or personal history of atopy, smoking history and symptoms using the adhesive. FEV1 /(forced expiratory volume in 1 second)/ was measured as a base-line and after working with the adhesive. Skin tests to common allergens were performed on all subjects. Two subjects who stated they wheezed with adhesive had falls in FEV1 of 15% and 18% from base-line. Totally symptom-free subjects had falls of less than 4% from base-line or a rise in FEV1. There was no clear relationship between smoking habits or atopic state or skin rashes with resin and a fall in FEV1. There is no simple way to identify those at risk of developing wheeze. Care should be taken with epoxy adhesives to avoid sensitization and where it occurs a simple questionnaire would provide a screening method.
For more Human Toxicity Excerpts (Complete) data for PYROMELLITIC DIANHYDRIDE (7 total), please visit the HSDB record page.
An estimated BCF of 9 was calculated for pyromellitic dianhydride(SRC), using an estimated log Kow of 2.14(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).
The Henry's Law constant for pyromellitic dianhydride is estimated as 7.5X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pyromellitic dianhydride is expected to be essentially nonvolatile from water surfaces(2). Pyromellitic dianhydride's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). Pyromellitic dianhydride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.8X10-6 mm Hg(SRC), determined from a fragment constant method(3).
/LABORATORY ANIMALS: Acute Exposure/ Poisoning /in animals/ is accompanied by CNS depression including behavioral changes (ataxia, somnolence, adynamia, muscle weakness, etc.). Death within the first three days.
/LABORATORY ANIMALS: Acute Exposure/ /1,2,4,5-Benzenetetracarboxylic, 1,2:4,5 dianhydride/ exhibits mild sensitizing properties on skin application of 0.2 mg/kg bw to guinea pigs.
/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Female rats exposed to 4.4 and 8.8 mg/kg bw for 6 months developed changes in the activities of a number of enzymes (cholinesterase, AST and ALT, cytochrome oxidase, etc.). Gross pathology and histology changes were evident.
The rate constant for the vapor-phase reaction of pyromellitic dianhydride with photochemically-produced hydroxyl radicals has been estimated as 2.9X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 56 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pyromellitic dianhydride is a hygroscopic substance that undergoes hydrolysis initially forming the monohydride and subsequently pyromellitic acid when contacted by moist air(2); however the rate of this reaction was not quantified. The second order base catalyzed rate constant of pyromellitic dianhydride was estimated as 0.868 l/mol-sec using an estimation method based on perturbed molecular orbital theory and linear free energy relationship (LFER) methods(3). This corresponds to a half-life of about 9 days at pH 8(SRC). Pyromellitic dianhydride absorbs light greater than 290 nm and is susceptible to direct photolysis in the environment(4), but the kinetics of this reaction are not known.
NIOSH (NOES Survey 1981-1983) has statistically estimated that 286 workers (16 of these are female) are potentially exposed to pyromellitic dianhydride in the US(1). Occupational exposure to pyromellitic dianhydride may occur through inhalation of dust and dermal contact with this compound at workplaces where pyromellitic dianhydride is produced or used(SRC).
Paint and Coating Manufacturing
1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone: ACTIVE
解説無水ピロメリト酸,白色の固体.融点287 ℃,沸点397~400 ℃.d"1.68.芳香族ジアミンと耐熱,耐薬品性のポリイミド樹脂をつくる.エステル化して塩化ビニル樹脂の可塑剤に使われる.森北出版「化学辞典(第2版)
用途耐熱エポキシ樹脂の架橋剤。アルキド樹脂、合成潤滑油、防さび剤、低揮発可塑剤、アルカリ可溶ポリエステル等の原料。
使用Pyromellitic dianhydride (PMDA) is employed as a curing agent for epoxy agent resins used for casting, laminating, the manufacture of moulding powders, adhesives and coatings.
一般的な説明Pyromellitic dianhydride (PMDA) is an acidic anhydride that can be used as a repair agent and as a chain extender in the formation of polyethylene terephthalate (PET) based chain extensions. It is mainly used in the production of thermoplastics and other coating applications.
製造方法Pyromellitic Dianhydride is prepared by gas-phase oxidation of 1,2,4,5-tetramethylbenzene (or related tetrasubstituted benzene derivatives). An idealized equation is:C6H2(CH3)4 + 6 O2 → C6H2(C2O3)2 + 6 H2OIn the laboratory, it can be prepared by dehydration of pyromellitic acid using acetic anhydride.
合成方法プソイドクメンあるいはデュレンを原料とする方法がある。プソイドクメンを原料とする場合も水トリメリト酸同様,HF-BF触媒存在下でのCOによるカルボニル化反応により得られる2,4,5-トリメチルベンズアルデヒドを水溶媒中で空気酸化した後,脱水することにより得られる。
純化方法Crystallise the dianhydride from ethyl methyl ketone or dioxane. Dry, and sublime it in vacuo.[Beilstein 19 H 196, 19/5 V 407.]