Grundinformationen
- Standard-SMILES
COC(=O)c1cccc(C(=O)OC)c1- InChIKey
VNGOYPQMJFJDLV-UHFFFAOYSA-N- Summenformel
- C10H10O4
- Durchschnittliche Molmasse
- 194,18 g/mol
- Monoisotopische Masse
- 194,0579088
Namen und Bezeichner
- Bevorzugter Name
- Dimethyl isophthalate
- IUPAC
- dimethyl benzene-1,3-dicarboxylate
- Lokaler Name
- Dimethylisophthalat
- Englischer Name
- Dimethyl isophthalate
- Summenformel
- C10H10O4
- Molmasse
- 194.18
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
1459-93-4- PubChem CID
- 15088
- DTXSID
DTXSID8027402- ChEMBL
CHEMBL2010300- UNII
- 2UY9Y3574K
- EC Number
- 215-951-9
- Nikkaji
- J7.498E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,2
- Polarare Oberfläche (TPSA)
- 52,6 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 202
Experimentelle und physikochemische Eigenschaften
Color/Form
Needles from dilute alcohol
... Solid at room temperature.
Solubility
Slightly soluble in alcohol.
In water, 290 mg/L, temperature not specified
Vapor Pressure
0.00963 [mmHg]
9.63X10-3 mm Hg at 25 °C /estimated/
Food Contact Substances
FCS -> FDA Cumulative Estimated Daily Intake (CEDI)
FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physikochemische Eigenschaften
- Schmelzpunkt
- 64 · 64-68 °C (lit.)
- Siedepunkt
- 124 °C · 124 °C (12.0016 mmHg)
- Dichte
- 1.1477 · 1.1477
- Dampfdichte
- 6.8 · 6.8 (vs air)
- Dampfdruck
- 93.7 mm · 93.7 mm Hg ( 208 °C)
- Brechungsindex
- 1.5168 · 1.5168 (estimate)
- Flammpunkt
- 138 °C · 138 °C
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- 0.29 g/l · 0.29g/l insoluble
- Aggregatzustand
- Flakes or Crystalline Powder
- pka
- -5.32 · -5.32[at 20 ℃]
- Farbe
- White to off-white
- Wasserlöslichkeit
- Insoluble
- BRN
- 1912251 · 1912251
- Henry's Law Constant
- 1.6 · 1.6×102 mol/(m3Pa) at 25℃, HSDB (2015)
- InChI
- 1S/C10H10O4/c1-13-9(11)7-4-3-5-8(6-7)10(12)14-2/h3-6H,1-2H3
- InChIKey
- VNGOYPQMJFJDLV-UHFFFAOYSA-N
- SMILES
- COC(=O)c1cccc(c1)C(=O)OC
- LogP
- 2.1 at · 2.1 at 20℃
- CAS Datenbank
- 1459 · 1459-93-4(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · 1,3-Benzenedicarboxylic acid dimethyl ester(1459-93-4)
- EPA chemische Informationen
- Dimethyl isophthalate (1459-93-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2% (3 of 152) of reports.
Warning
H319 (98%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 152 reports by companies from 4 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Chemical: 1,3-Benzenedicarboxylic acid, dimethyl ester
1,3-Benzenedicarboxylic acid, 1,3-dimethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Benzenedicarboxylic acid, 1,3-dimethyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 13-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5958
1,3-Benzenedicarboxylic acid, dimethyl ester: Does not have an individual approval but may be used under an appropriate group standard
NFPA Hazard Classification
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.
Sicherheit und Schutzausrüstung
Disposal Methods
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.
Preventive Measures
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.
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 36(SRC), determined from a structure estimation method(2), indicates that dimethyl isophthalate is expected to have very high mobility in soil(SRC). Volatilization of dimethyl isophthalate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dimethyl isophthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.6X10-3 mm Hg(4). Dimethyl isophthalate, present at 100 mg/L, reached 94 to 102% of its theoretical BOD after 2 weeks using an activated sludge inoculum(5).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 36(SRC), determined from a structure estimation method(2), indicates that dimethyl isophthalate 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 6.1X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 4(SRC), from an estimated log Kow of 1.66(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 350 and 35 days at pHs 7 and 8, respectively(8). Dimethyl isophthalate, present at 100 mg/L, reached 94 to 102% of its theoretical BOD after 2 weeks using an activated sludge inoculum(9).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl isophthalate, which has an estimated vapor pressure of 9.6X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase dimethyl isophthalate 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 25 days(SRC), calculated from its rate constant of 6.4X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dimethyl isophthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of dimethyl isophthalate can be estimated to be 36(SRC). According to a classification scheme(2), this estimated Koc value suggests that dimethyl isophthalate is expected to have very high mobility in soil.
Human Toxicity Excerpts
/ALTERNATIVE and IN VITRO TESTS/ Comparative toxicity of phthalate esters to HeLa-S3 cells was studied by determining their effect on doubling time of the cells. The toxicity of the esters decreasing in order: diethyl phthalate, butyl phthalyl butyl glycolate, di-iso-butyl phthalate, ethyl phthalyl ethyl glycolate, bis(2-ethylhexyl) phthalate, dimethyl isophthalate, dibutyl phthalate, methyl phthalyl ethyl glycolate, dimethyl phthalate, and dioctyl phthalate.
Environmental Bioconcentration
An estimated BCF of 4 was calculated in fish for dimethyl isophthalate(SRC), using an estimated log Kow of 1.66(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).
Volatilization from Water/Soil
The Henry's Law constant for dimethyl isophthalate is estimated as 6.1X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dimethyl isophthalate is expected to be essentially nonvolatile from water surfaces(2). Dimethyl isophthalate is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.6X10-3 mm Hg(3).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ Eye Rabbit 500 mg/26 hr severe toxic effects were observed.
/ALTERNATIVE and IN VITRO TESTS/ To assess the toxicity of dimethyl isophthalate to cells in culture, monolayers of L-cells and chicken embryos cells were overlaid with agar and undiluted dimethyl isophthalate was then applied to paper disks which had previously been placed on the agar overlay. Dimethyl isophthalate was scored as toxic since it created a zone of dead cells in the area adjacent to the test site.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of dimethyl isophthalate with photochemically-produced hydroxyl radicals has been estimated as 6.4X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 25 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.23 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 350 and 35 days at pH values of 7 and 8, respectively(2). Dimethyl isophthalate does contain chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Probable Routes of Human Exposure
Occupational exposure to dimethyl phthalate may occur through inhalation of aerosols and dermal contact with this compound at workplaces where dimethyl isophthalate is produced or used. Use data indicate that the general population may be exposed to dimethyl isophthalate via dermal contact with and inhalation of products containing this compound. (SRC)
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29173980
- RTECS-Nr.
- NT2540000
- risk_code
- 36
- hazard_code
- Xi
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 1459-93-4(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a plasticizer, to make polyester resins, as a polyacrylate resin comonomer, and as a perfume fixative; [HSDB]
PLASTICIZER
CHEM INTERMED FOR POLYESTER RESINS
Polyacrylate resin comonomer; perfume fixative.
U.S. Production
2023: 50,000 - <250,000 lb
(1979) PROBABLY GREATER THAN 2.27X10+6 G
(1981) PROBABLY GREATER THAN 2.27X10+6 G
1,3-Benzenedicarboxylic acid, dimethyl ester 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#5716]
General Manufacturing Information
Plastics Material and Resin Manufacturing
1,3-Benzenedicarboxylic acid, 1,3-dimethyl ester: ACTIVE
"Morflex 1129" [Reilly] ... trademark for chemical intermediate
Anwendungen
VerwendenDimethyl isophthalate is used as a plasticizer, to make polyester resins, as a polyacrylate resin comonomer, and as a perfume fixative. It may be used as an internal standard for determining, dimethyl-tere-phthalate (DMtP), dimethyl-phthalate (DMP), diethyl phthalate (DEP) in soil samples and biosolids using gas-chromatography coupled to mass spectrometry (GC-MS). It may also be used as an analytical reference standard for the quantification of the analyte in complex matrices including plastics, cosmetics, and environmental samples using gas chromatography coupled to positive chemical ionization mass spectrometry (GC-CIMS).
Darstellung
synthetischeDimethyl isophthalate is synthesized by esterifying isophthalic acid with methanol: Isophthalic acid (1.66gm, 0.1mmol) in super dry methanol (60mL) containing 2-3 drops of concentrated H2SO4 (AR) was refluxed till it dissolved. Then, the reaction mixture was poured onto ice cold water, immediately a solid started separating from the clear solution. To this a solution of sodium bicarbonate was added till the effervescence seized. The ester thus obtained was filtered and washed with water for several times (M.P: 64-67°C).
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