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Dimethylisophthalat

Dimethyl isophthalate

HCID 15088
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Grundinformationen

CAS
1459-93-4
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

DIMETHYL ISOPHTHALATE1459-93-4Dimethyl m-phthalateDimethyl benzene-1,3-dicarboxylateMethyl isophthalateIsophthalic acid dimethyl esterDimethyl 1,3-benzenedicarboxylateMorflex 11291,3-Benzenedicarboxylic acid, dimethyl esterIsophthalic acid, dimethyl esterMethyl 3-(carbomethoxy)benzoateNSC 15313
Weitere Namen anzeigen
Dimethyl isophthalatUniplex 270RARECHEM AL BF 0071dimethylm-phthalate
HSDB 61381,3-Benzenedicarboxylic acid, 1,3-dimethyl esterEINECS 215-951-9Dimethylester kyseliny isoftaloveDTXSID8027402BRN 1912251Dimethylester kyseliny isoftalove [Czech]AI3-02247

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 StruktureigenschaftenWird ergänzt

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

PolymersPlastics & Rubber -> Phthalate Esters
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
Density1.194 g/cu cm at 20 °C
Color/Form · 2 Einträge

Needles from dilute alcohol

... Solid at room temperature.

Solubility · 2 Einträge

Slightly soluble in alcohol.

In water, 290 mg/L, temperature not specified

Flash Point280 °F (138 °C) (Closed cup)
Boiling Point282 °C
DecompositionWhen heated to decomp it emits acrid smoke and fumes.
Melting Point67.5 °C
Vapor Pressure · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 4 Einträge

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

Hazards SummaryA severe eye irritant after applying to rabbit eye for 26 hours; Oral LD50 (rat) = 4390 mg/kg; [HSDB] An irritant; [MSDSonline] See PHTHALATE ESTERS.
Special ReportsITC/USEPA; Information Review #304 (Draft) Dimethyl Isophthalate (1982)
NFPA Hazard Classification · 3 Einträge

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.

Chemie und Industrie

Verwendung und Herstellung

Uses · 4 Einträge

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 · 5 Einträge

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]

Industry UsesIntermediate
Methods of ManufacturingMethanol + isophthalic acid (esterification)
General Manufacturing Information · 3 Einträge

Plastics Material and Resin Manufacturing

1,3-Benzenedicarboxylic acid, 1,3-dimethyl ester: ACTIVE

"Morflex 1129" [Reilly] ... trademark for chemical intermediate

Anwendungen · 1 Eintrag

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).

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HRID 24300als Eduktuspto-grants-2005_02
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HRID 95837als EduktTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
Reaktionsgleichung von HRID 263215
HRID 263215als Produktuspto-grants-1979_05
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HRID 346470als Eduktuspto-grants-2007_02
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Reaktionsgleichung von HRID 399846
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0.00963 [mmHg]

9.63X10-3 mm Hg at 25 °C /estimated/

Food Contact Substances · 2 Einträge

FCS -> FDA Cumulative Estimated Daily Intake (CEDI)

FCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR

Refractive IndexIndex of refraction: 1.5168 at 20 °C/D

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)

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and CategoriesEye Irrit. 2 (98%)

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresWater or foam may cause frothing.
Disposal Methods · 1 Eintrag

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 · 1 Eintrag

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 · 3 Einträge

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).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Soil Adsorption/Mobility · 1 Eintrag

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.

Natural Pollution SourcesThe identification of dimethyl isophthalate in surface waters near, and shortly after the Mount St. Helens volcano erupted is believed to be due to the destructive pyrolysis of surrounding conifers and other organic matter(1).
Human Toxicity Excerpts · 1 Eintrag

/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.

Artificial Pollution SourcesDimethyl isophthalate's production and use as a polyacrylate resin comonomer and as a perfume fixative(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Dimethyl isophthalate, present at 100 mg/L, reached 94 to 102% of its theoretical BOD after 2 weeks using an activated sludge inoculum(1).
Environmental Bioconcentration · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

/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 · 1 Eintrag

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 · 1 Eintrag

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
Darstellung · 1 Eintrag

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).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Isophthalsure3-Formylbenzoesuremethyl 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoateDimethyl 5-iodoisophthalateMethyl-3-chlorbenzoatMethanol

Nachgelagerte Produkte

polyester-based liquid crystalling ionmer containing sulfonate groupMethyl 3-formylbenzoateIsophthaloyldichloridDiphenylisophthalatDimethyl-5-bromisophthalat1,3-Bis(chlormethyl)benzolDimethyl-5-aminoisophthalat2-(3-(methoxycarbonyl)phenyl)acetic acid3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester