Dipentyl phthalate
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Dipentyl phthalate
structure -
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CAS No:
131-18-0
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Formula:
C18H26O4
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Chemical Name:
Dipentyl phthalate
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Synonyms:
1,2-Benzenedicarboxylic acid,1,2-dipentyl ester;Phthalic acid,dipentyl ester;1,2-Benzenedicarboxylic acid,dipentyl ester;Amoil;Amyl phthalate;Diamyl phthalate;Dipentyl phthalate;Di-n-amyl phthalate;Di-n-pentyl phthalate;Di-n-pentyl o-phthalate;NSC 4720;1,2-Dipentyl benzene-1,2-dicarboxylate
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CAS No:
Description
PHYSICAL DESCRIPTION: Clear colorless to light yellow liquid. Practically odorless. Floats on water. (NTP, 1992)
Di-n-pentyl phthalate is a clear colorless to light yellow liquid. Practically odorless. Floats on water. (NTP, 1992)
Di-n-pentyl phthalate is a clear colorless to light yellow liquid. Practically odorless. Floats on water. (NTP, 1992)|Dipentyl phthalate is a phthalate ester that is the dipentyl ester of benzene-1,2-dicarboxylic acid. It has a role as a plasticiser. It is a phthalate ester and a diester. It derives from a pentan-1-ol.
Dipentyl phthalate Basic Attributes
306.4
306.40
205-017-9
5DC92K224X
4720
3082
DTXSID5031131
Colorless, oily liquid
2917349000
Characteristics
52.6
5.8
Di-n-pentyl phthalate is a clear colorless to light yellow liquid. Practically odorless. Floats on water. (NTP, 1992)
1.022 g/cm3 @ Temp: 20 °C
-55ºC
342 °C
188.8±8.5 °C
1.496
In water, 0.8 mg/L at 25 deg C
2.8E-05mmHg at 25°C
10.5 (AIR= 1)
Nearly odorless
Henry's Law constant = 8.88X10-7 atm-cu m/mol at 25 °C (est)
Wt/gal = 8.52 lb|... Resistance to migration from polymers, low temperature flexibility ... compatibility with polar polymers and additives over a wide range of compositions. /Phthalate esters/|Phthalate esters would be expected to have UV maxima in the 230 nm and 270 nm regions. /Phthalate esters/|Hydroxyl radical reaction rate constant = 1.21X10-11 cu cm/molec-sec at 25 °C (est)
No rapid reaction with air. No rapid reaction with water. Insoluble in water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
DI-N-AMYL PHTHALATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Can generate electrostatic charges.
-13,900 Btu/lb= -7,720 cal/g= -323X10+5 J/kg
140 Btu/lb= 78 cal/g= 3.2X10+5 J/kg
Safety Information
Ⅲ
3082
3
9
S45;S53;S61
TI1930000
T: Toxic;N: Dangerous for the environment;
P201-P273-P308 + P313
H360-H400
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.
Nat'l Research Council Canada; Phthalate Esters in the Aquatic Environment (1980) NRCC No. 17583|USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067|USEPA/ECAO; Atlas Document for: Phthalate Esters (1980)
This chemical is combustible. (NTP, 1992)
|Danger|H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P273, P281, P308+P313, P391, P405, and P501|Aggregated GHS information provided by 252 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]|H360: May damage fertility or the unborn child [Danger Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed 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 material under ambient temperatures. (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) Wear goggles or face shield; rubber gloves. (USCG, 1999)
SLIGHT, WHEN EXPOSED TO HEAT OR FLAME; IT CAN REACT WITH OXIDIZING MATERIALS.
Water or foam may cause frothing.
... DIAMYL PHTHALATE ... WAS REMOVED FROM AIR BY AN ELECTROFILTER, ... . REMOVAL EFFICIENCY IS 82-93%.
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.
| 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.
Diamyl phthalate was not found in 4 domestic sewages; 6 domestic sewages with storm runoff and small industrial effluent; 2 domestic sewage with storm runoff and large industrial effluent with a detection limit of 0.3 ug/L(1).
Toxicity
Di-N-pentylphthalate (DPP) was tested using the Fertility Assessment by Continuous Breeding (FACB) protocol in Swiss CD-1 mice as part of a structure-activity evaluation of a variety of phthalates. Body weights, food & water consumptions, & clinical signs in a dose-range-finding study were used to set doses for the main study of 0.0, 0.5, 1.25, & 2.50% in feed. Measured feed consumption was increased by 8-35% at the highest concn, but was unchanged in other DPP groups. Based on these measures, these concns produced calculated consumption estimates of nearly =0.76, 2.16, & 4.8 g/kg/day. During the continuous breeding phase (Task 2), all control pairs had at least 1 litter, while only 4 of 19 low dose pairs delivered a litter, & no middle dose or high dose pairs delivered a litter. In the 7 litters delivered at the low dose, the number of live pups/litter was reduced from control values by 90%; there were insufficient live pups to calculate pup weights adjusted for body weight. At the end of Task 2, the control & high dose mice were cross-mated. The groups that contained either treated males, or treated females, gave birth to no live young, while 61% of cohabited control pairs bore live young. The F0 control & high dose mice were necropsied after the crossover mating trial. The treated females weighed 9% less than their controls, while body-weight-adjusted liver weight was 56% greater than controls, & adjusted kidney weight was 12% less. Treated males weighed 10% less than controls, while adjusted liver weight was 55% greater. In males, adjusted kidney weights, seminal vesicles, & epididymal weights were reduced by 30%, 29% & 19% respectively. At the high dose, absolute testis weight was decreased by 78%, & there were no detectable epididymal sperm. A second generation evaluation was not performed for DPP. Thus, DPP at these concns sharply reduced litter size & number of litters/pair in the F0 mice.
Diamyl phthalate's production and use as a plasticizer(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 27,000(SRC), determined from a log Kow values of 5.62(2), and a regression-derived equation(3), indicate that diamyl phthalate is expected to be immobile in soil(SRC). Volatilization of diamyl phthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Diamyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.0X10-4 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation studies using pure cultures indicate that diamyl phthalate may biodegrade under aerobic conditions yielding phthalic acid and amyl alcohol(6). Although biodegradation data on diamyl phthalate are limited, biodegradation studies on a series of phthalate esters have demonstrated that, in general, phthalate esters are readily biodegraded(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 27,000(SRC), determined from a log Kow values of 5.62(2), and a regression-derived equation(3), indicate that diamyl phthalate 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 8.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 420(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(7). Estimated hydrolysis half-lives of 3.4 years and 130 days at pHs 7 and 8, respectively, suggest that hydrolysis is not expected to be an important process(8). Biodegradation studies using pure cultures indicate that diamyl phthalate may biodegrade under aerobic conditions yielding phthalic acid and amyl alcohol(9). Although biodegradation data on diamyl phthalate are limited, biodegradation studies on a series of phthalate esters have demonstrated that, in general, phthalate esters are readily biodegraded(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diamyl phthalate, which has an estimated vapor pressure of 2.0X10-4 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 diamyl phthalate 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 32 hours(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Diamyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of diamyl phthalate with photochemically-produced hydroxyl radicals has been estimated as 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 32 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 6.4X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 3.4 years and 130 days at pH values of 7 and 8, respectively(2). Diamyl phthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 420 was calculated in fish for diamyl phthalate(SRC), using a log Kow of 5.62(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(4).
The Koc of diamyl phthalate is estimated as 27,000(SRC), using a log Kow of 5.62(1), and 5.66(2), respectively, and a regression-derived equation(2). According to a classification scheme(4), this Koc value suggests that diamyl phthalate is expected to be immobile in soil.
The Henry's Law constant for diamyl phthalate is estimated as 8.9X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that diamyl phthalate is expected to be essentially nonvolatile from water surfaces(2). Diamyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.0X10-4 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to diamyl phthalate may occur through inhalation of aerosols and dermal contact with this compound at workplaces where diamyl phthalate is used as a plasticizer or where plastics are produced. Use data indicate that the general population may be exposed via dermal contact with consumer products containing this compound. (SRC)
Drug Information
Diamyl phthalate was metabolized in vivo to its corresponding monoester by nonspecific esterases in the intestinal mucosa and other tissues.
Inhalation of vapors from very hot material may cause headache, drowsiness, and convulsions. Hot vapors may irritate eyes. (USCG, 1999)
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)
/ALTERNATIVE and IN VITRO TESTS/ /It was/ previously found that some phthalates have nongenomic effects, exerting inhibitory effects on the functional activities of nicotinic acetylcholine receptors (nAChRs) in bovine chromaffin cells. ... This study ... investigated the effects of eight phthalates on the calcium signaling of human nAChR by using human neuroblastoma SH-SY5Y cells. All eight phthalates, with different potency, have inhibitory roles on the calcium signaling coupled with human nAChR, but not muscarinic acetylcholine receptors (mAChRs). For inhibition of human nAChR, the strongest to weakest potencies were observed as di-n-pentyl phthalate (DPP) --> butyl benzyl phthalate (BBP) --> di-n-butyl phthalate (DBP) --> dicyclohexyl phthalate (DCHP) --> di-n-hexyl phthalate (DHP) --> di-(2-ethyl hexyl) phthalate (DEHP) --> di-n-propyl phthalate (DPrP) --> diethyl phthalate (DEP). The potencies of phthalates were associated with their structures such that the most effective ones had dialkyl group carbon numbers of C4 or C5, with shorter or longer numbers resulting in decreased potency. At as low as 0.1 uM, DPP, DBP, BBP, DCHP and DHP significantly inhibited the calcium signaling of human nAChR. The IC50 of phthalates on human nAChR, ranging from 0.32 to 7.96 uM, were 10-50 lower than those for bovine nAChR.
di-n-pentyl phthalate
Dipentyl phthalate Use and Manufacturing
By esterification of the phthalic anhydride with amyl alcohol in the presence of approximately 1% concentrated sulfuric acid as catalyst.
Plasticizer
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#998]
1,2-Benzenedicarboxylic acid, 1,2-dipentyl ester: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.
Method: EPA-OSW 8061A; Procedure: gas chromatography with electron capture detection; Analyte: dipentyl phthalate; Matrix: groundwater, leachate, soil, sludge, and sediment; Detection Limit: 0.11 ug/L.|IN AN ATTEMPT TO DEVELOP A METHOD FOR THE DETERMINATION OF PHTHALATE ESTERS IN WATER BY ADSORPTION CHROMATOGRAPHY, THE HIGH PERFORMANCE LIQUID CHROMATOGRAPHIC BEHAVIOR OF DIAMYL PHTHALATE IN WATER USING AN OCTADECYLTRICHLOROSILANE BONDED STATIONARY PHASE WAS EXAMINED. PHTHALATE ESTERS IN WATER WERE COMPLETELY ADSORBED ON OCTADECYLTRICHLOROSILANE BONDED BEADS AND THEIR ELUTION ORDER IN 100% WATER TO 100% METHANOL GRADIENT SYSTEM WAS DIRECTLY RELATED TO THE NUMBER OF ALKYL CARBON ATOMS IN THE ESTER GROUPS OF PHTHALATES. STUDY INDICATED THAT THE SEPARATION MECHANISM MAY BE DUE TO THE INTERACTION OF AFFINITY BETWEEN OCTADECYL GROUPS OF THE BONDED STATIONARY PHASE AND THE LENGTH OF THE ALKYL CHAIN IN THE ESTER GROUP OF EACH PHTHALATE WITH SOLUBILITIES OF EACH PHTHALATE ESTER FOR THE MOBILE PHASE.
THE KOVATS RETENTION INDEX OF DIAMYL PHTHALATE WAS DETERMINED BY GLASS CAPILLARY COLUMN GAS CHROMATOGRAPHY FOR IDENTIFICATION OF THE ESTERS IN BIOLOGICAL FLUIDS. COLUMN PARAMETERS WERE: 0.5% OV-101 COATINGS, 230 °C, HELIUM OR NITROGEN AS CARRIER GAS; 0.5% SE-30 COATING, 250 °C. A FLAME IONIZATION DETECTOR WAS USED WITH BOTH COLUMNS.
Computed Properties
Molecular Weight:306.4
XLogP3:5.8
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:12
Exact Mass:306.18310931
Monoisotopic Mass:306.18310931
Topological Polar Surface Area:52.6
Heavy Atom Count:22
Complexity:295
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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