Hexahydrophthalic anhydride
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Hexahydrophthalic anhydride
structure -
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CAS No:
85-42-7
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Formula:
C8H10O3
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Chemical Name:
Hexahydrophthalic anhydride
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Synonyms:
1,3-Isobenzofurandione,hexahydro-;1,2-Cyclohexanedicarboxylic anhydride;Hexahydro-1,3-isobenzofurandione;Hexahydrophthalic anhydride;Araldite HT 907;Lekutherm Hardener H;HHPA;Hexahydrophthalic acid anhydride;1,2-Cyclohexanedicarboxylic acid anhydride;Rikacid HH;Epilox H 11-01;Araldite HT 904;Rikacid HH-A;Araldite HY 907;Cyclohexanedicarboxylic anhydride;Rutapox HX;Rikacid HHPA;Araldite HY 925;Araldite Hardener HY 925;HY 925;Rutadur AG;NSC 8622;Rikacid MH 700E;MH 700E;HT 907;EP 400B;Aradur HY 925;Hexahydro-2-benzofuran-1,3-dione;Cyclohexane-1,2-dicarboxylic acid anhydride;Rikacid MH 600;Hardener HY 925;HV 136;MY 1832;95327-28-9;102483-85-2;109265-67-0;117276-22-9
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CAS No:
Description
White crystalline powder
DryPowder; OtherSolid|SOLID IN VARIOUS FORMS.|Dry powder or solid in various forms, or clear, colorless, viscous liquid.
Hexahydrophthalic anhydride is a cyclic dicarboxylic anhydride that is the cyclic anhydride of hexahydrophthalic acid. It has a role as an allergen. It is a cyclic dicarboxylic anhydride and a tetrahydrofurandione.
Hexahydrophthalic anhydride Basic Attributes
154.163
154.16
238-009-9
1643
8622
DTXSID8026515
Clear, colorless, viscous liquid|... becomes a glassy solid at 35-36 °C
2932999099
Characteristics
43.37000
1.2
DryPowder; OtherSolid
1.2±0.1 g/cm3
32 °C
146 °C @ Press: 15 Torr
143.9±16.5 °C
1.502
Solubility in water: reaction
Keep container tightly closed in a dry and well-ventilated place.
5.35X10-2 mm Hg at 25 deg C (est)
Relative vapour density (air = 1): 5.3
Henry's Law constant = 2.15X10-5 atm-cu m/mol at 25 °C (est)
Hydroxyl radical reaction rate constant = 6.8X10-12 cu cm/molecule-sec at 25 °C (est)
Safety Information
3335
1
R41;R42/43
S23-S24-S26-S37/39
Xn:Harmful;
Dry. Store in an area without drain or sewer access.
Stable under normal temperatures and pressures.
P261-P280-P284-P304 + P340-P305 + P351 + P338 + P310
H317-H318-H334
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.
Materials to avoid: Strong oxidizing agents, strong acids, strong bases.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
|Danger|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P305+P351+P338, P310, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 477 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P271, P272, P280, P285, P302+P352, P304+P340, P304+P341, P305+P351+P338, P310, P312, P321, P333+P313, P342+P311, P363, P403+P233, P405, and P501
Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Handle with gloves.|Face shield and safety glasses.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Special protective equipment for fire-fighter: Wear self contained breathing apparatus for fire fighting if necessary.
ACCIDENTAL RELEASE MEASURES. Personal precautions: Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.|ACCIDENTAL RELEASE MEASURES. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.
Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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: 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. Ensure that the local ventilation moves the contaminant away from the worker.
Strong irritant to eyes and skin
Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers.
Dry. Store in an area without drain or sewer access.
The substance is irritating to the skin. The substance is severely irritating to the eyes.
Repeated or prolonged contact may cause skin sensitization. Repeated or prolonged inhalation may cause asthma.
NO open flames.
AVOID ALL CONTACT!
Use ventilation, local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
Toxicity
LD50 Rabbit (New Zealand White) dermal >2000 mg/kg (limit dose) (24 hr administration, 14 day observation)|LC50 Rat (Sprague-Dawley, M/F) inhalation 1100 mg/cu m (80% in ethanol, 4 hr/15 days)|LD50 Rat oral (gavage) 4040 mg/kg (20% suspension in peanut oil)|LD50 Rats oral 2700 to 2800 mg/kg
Hexahydrophthalic anhydride's production and use as a chemical intermediate and hardener in epoxy resins(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that hexahydrophthalic anhydride is expected to have very high mobility in soil(SRC). Volatilization of hexahydrophthalic anhydride from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Hexahydrophthalic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing the Japanese MITI test, 4% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is not a rapid environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that hexahydrophthalic anhydride is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.1X10-5 atm-cu m/mole(4)((SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.3 and 20 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 13(SRC), from an estimated log Kow of 2.17(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hexahydrophthalic anhydride is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(3). Utilizing the Japanese MITI test, 4% of the Theoretical BOD was reached in 4 weeks(8) indicating that biodegradation is not a rapid environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexahydrophthalic anhydride, which has an estimated vapor pressure of 5.3X10-2 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexahydrophthalic 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 19 hrs(SRC), calculated from its rate constant of 6.8X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Hexahydrophthalic anhydride does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of hexahydrophthalic anhydride with photochemically-produced hydroxyl radicals has been estimated as 6.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 19 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Hexahydrophthalic anhydride is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(2). Hexahydrophthalic anhydride does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 13 was calculated in fish for hexahydrophthalic anhydride(SRC), using an estimated log Kow of 2.17(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).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of hexahydrophthalic anhydride can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that hexahydrophthalic anhydride is expected to have very high mobility in soil.
The Henry's Law constant for hexahydrophthalic anhydride is estimated as 2.1X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that hexahydrophthalic anhydride is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2.3 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 20 days(SRC). Hexahydrophthalic anhydride's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Hexahydrophthalic anhydride is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.3X10-2 mm Hg(SRC), determined from a fragment constant method(3).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of hexahydrophthalic anhydride is 100 to 999; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 15,061 workers (7,356 of these were female) were potentially exposed to hexahydrophthalic anhydride in the US(1). Occupational exposure to hexahydrophthalic anhydride may occur through inhalation and dermal contact with this compound at workplaces where hexahydrophthalic anhydride is produced or used(SRC). Hexahydrophthalic anhydride levels were measured in urine samples from 20 workers exposed to air levels of 11-220 ug hexahydrophthalic anhydride/cu m in plants manufacturing electrical capacitors and automotive ignition systems. Approximately 900 nmol/mmol creatine was reported after 6 hrs of exposure with levels dropping to 50 nmol/mmol by 18 hours post exposure(2).
Drug Information
Agents causing the narrowing of the lumen of a bronchus or bronchiole. (See all compounds classified as Bronchoconstrictor Agents.)
Six healthy volunteers were exposed to gaseous hexahydrophthalic anhydride (HHPA) ... for 8 hr. The respiratory uptake of the inhaled HHPA was almost complete. Rapid increases in plasma and urinary levels of hexahydrophthalic acid (HHP acid) were seen. During the first 4 hr after the end of exposure, the half-time of HHP acid in plasma was about 2 hr. A corresponding decay was seen in urine. The correlations (r > 0.90) between the air concentrations of HHPA and the levels of HHP acid in plasma and urine were close. They were even closer (r > 0.96) when the total respiratory uptake of HHPA was used. Urinary pH adjustment by intake of ammonium chloride or sodium hydrogen carbonate did not significantly alter the excretion of HHP acid. The results show that the analysis of HHP acid in plasma or urine is useful as a biological monitor for exposure to HHPA.|Human volunteers /were/ exposed at vapor levels of 10, 40, or 80 ug/cu m for 8 hours. Inhaled /hexahydrophtalic anhydride/ (HHPA) was almost completely absorbed in the respiratory tract, probably as /hexahydrophthalic acid/ (HHP acid) after hydrolysis on the mucus membrane. HHP acid in plasma rapidly increased without reaching steady state during exposure and decreased rapidly following removal from exposure. HHP acid was excreted through the kidneys.
Human volunteers /were/ exposed at vapor levels of 10, 40, or 80 ug/cu m for 8 hours. Inhaled /hexahydrophtalic anhydride/ (HHPA) was almost completely absorbed in the respiratory tract, probably as /hexahydrophthalic acid/ (HHP acid) after hydrolysis on the mucus membrane. HHP acid in plasma rapidly increased without reaching steady state during exposure and decreased rapidly following removal from exposure. HHP acid was excreted through the kidneys.
Biological half-life of HHP acid in plasma was approximately 2 hr.
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
/HUMAN EXPOSURE STUDIES/ Six healthy volunteers were exposed to gaseous hexahydrophthalic anhydride (HHPA) ... for 8 hr. The respiratory uptake of the inhaled HHPA was almost complete. Rapid increases in plasma and urinary levels of hexahydrophthalic acid (HHP acid) were seen. During the first 4 hr after the end of exposure, the half-time of HHP acid in plasma was about 2 hr. A corresponding decay was seen in urine. The correlations (r > 0.90) between the air concentrations of HHPA and the levels of HHP acid in plasma and urine were close. They were even closer (r > 0.96) when the total respiratory uptake of HHPA was used. Urinary pH adjustment by intake of ammonium chloride or sodium hydrogen carbonate did not significantly alter the excretion of HHP acid. The results show that the analysis of HHP acid in plasma or urine is useful as a biological monitor for exposure to HHPA.|/HUMAN EXPOSURE STUDIES/ Organic acid anhydrides are potential sensitizers and cause occupational airway diseases. In an intervention study the efficacy of measures of hygiene at the workplace and possible selection bias were investigated. A first investigation with 110 workers exposed to hexahydrophthalic acid anhydride (HHPA) and methyltetrahydrophthalic acid anhydride (MTHPA) was carried out in July 1991. The results (skin prick test, specific serum IgE) showed that 20 people were sensitized, and in a challenge test the clinical relevance of the sensitization was confirmed in six subjects...|/HUMAN EXPOSURE STUDIES/ Nasal challenge tests were performed with a conjugate of hexahydro-1,3-isobenzofurandione (HHPA) and human serum albumin (HAS) at three increasing concentrations in exposed workers to test the pathogenetic relevance of serum antibodies (IgE and IgG) . Eleven subjects who reported work-related nasal symptoms and were IgE-sensitized against HHPA (Positive in skin-prick test and RAST against HHPA-HAS conjugate) had a decrease of nasal inspiratory peak flow and a significant increase of symptoms after the challenges. Eleven unsensitized subjects with no symptoms and nine unsensitized subjects who complained of work related nasal symptoms displayed no significant change in any parameter. The authors concluded that symptoms in some of the workers were caused by an IgE-mediated mast cell degranulation and ensuing inflammatory reaction involving eosinophil and neutrophil cells.|/HUMAN EXPOSURE STUDIES/ 53 humans. 5% suspension of hexahydro-1,3-isobenzofurandione in mineral oil (10 repeat test). Four out of fifty-three subjects gave a low grade sensitivity reaction and one marked reaction indicating sensitization. Interpretation of Results: Sensitizing .|For more Human Toxicity Excerpts (Complete) data for Hexahydrophthalic anhydride (14 total), please visit the HSDB record page.
araldite
The substance can be absorbed into the body by inhalation.
Cough. Wheezing.
Redness.
Redness. Pain.
Hexahydrophthalic anhydride Use and Manufacturing
Tetrahydrophthalic anhydride is formed by a Diels - Alder reaction with butadiene; hydrogenation of the anhydride yields hexahydrophthalic anhydride.
Intermediate for alkyds, plasticizers, insect repellents, and rust inhibitors; hardener in epoxy resins.
Adhesives and sealant chemicals
Building/construction materials not covered elsewhere
10,000,000 - 50,000,000 lb|1,3-Isobenzofurandione, hexahydro- is listed as a High Production Volume (HPV) chemical (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).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7761]|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,3-Isobenzofurandione, hexahydro-. Aggregated National Production Volume: 10 to < 50 million lbs.
All other chemical product and preparation manufacturing|1,3-Isobenzofurandione, hexahydro-: ACTIVE
Computed Properties
Molecular Weight:154.16
XLogP3:1.2
Hydrogen Bond Acceptor Count:3
Exact Mass:154.062994177
Monoisotopic Mass:154.062994177
Topological Polar Surface Area:43.4
Heavy Atom Count:11
Complexity:187
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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