Grundinformationen
- Standard-SMILES
CC(C)CCCCCOC(=O)c1ccccc1C(=O)OCCCCCC(C)C- InChIKey
IJFPVINAQGWBRJ-UHFFFAOYSA-N- Summenformel
- C24H38O4
- Durchschnittliche Molmasse
- 390,6 g/mol
- Monoisotopische Masse
- 390,27700969
Namen und Bezeichner
- Bevorzugter Name
- Diisooctyl phthalate
- IUPAC
- bis(6-methylheptyl) benzene-1,2-dicarboxylate
- Englischer Name
- Bis(6-methylheptyl) Phthalate
- Summenformel
- C24H38O4
- Molmasse
- 390.56
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
131-20-4、27554-26-3、71097-28-4- PubChem CID
- 33934
- DTXSID
DTXSID50873226- ChEMBL
CHEMBL3186540- ChEBI
CHEBI:34710- UNII
- 6A121LGB40
- EC Number
- 248-523-5
- Nikkaji
- J60.496H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 8,5
- Polarare Oberfläche (TPSA)
- 52,6 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 16
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 390
Experimentelle und physikochemische Eigenschaften
Density
0.980-0.983 at 20 °C/20 °C
Bulk density: Wt/gal = 8.20 lb at 20 °C
Relative density (water = 1): 0.99
Solubility
... compatible with vinyl chloride resins and some cellulosic resins
In water, 9.0X10-2 mg/L at 25 °C
Solubility in water: none
Flash Point
450 °F (USCG, 1999)
450 °F; 232 °C /(method not specified)/
450 °F (232 °C) (Closed cup)
227 °C c.c.
Boiling Point
1288 °F at 760 mmHg (USCG, 1999)
370 °C
370 °C
Melting Point
-4 °C /From Table/
-45 °C
Vapor Density
13.5 (Air = 1)
Relative vapor density (air = 1): 13.5
Vapor Pressure
0.0000055 [mmHg]
5.5X10-6 mm Hg at 25 °C
Vapor pressure at 20 °C: negligible
Physikochemische Eigenschaften
- Siedepunkt
- 384.9 · 384.9±10.0 °C(Predicted)
- Dichte
- 0.983 · 0.983±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Heated)
- Aggregatzustand
- liquid
- Farbe
- Colourless
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H360FD: May damage fertility; May damage the unborn child [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.8% (1 of 124) of reports.
Gefahrenhinweise
Regulatory Information
Chemical: 1,2-Benzenedicarboxylic acid, diisooctyl ester
Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient
Regulation (EC) No 178/2002 (amended)
1,2-Benzenedicarboxylic acid, 1,2-diisooctyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-diisooctyl 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)
Diisooctyl phthalate: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Special Hazards of Combustion Products: None (USCG, 1999)
Combustible.
Hazards Summary
There is confusion in the naming of the dioctyl phthalate esters: Di-n-octyl phthalate, Di-sec-octyl phthalate, and Diisooctyl phthalate. [CHEMINFO] Female mice fed >190 mg/kg/bw have weight loss and show increased resorptions, fetal malformations, and late fetal deaths; Mice fed 426 mg/kg/day show increased liver weight as well as reproductive effects; Oral LD50 (mouse) >26,000 mg/kg; Dioctyl phthalate may cause CNS depression and mild liver toxicity after ingestion of large amounts; [HSDB] No listed effects of short-term or long-term exposure; [ICSC] May cause irritation and liver damage; [MSDSonline] See PHTHALATE ESTERS.
FDA Requirements
Diisooctyl phthalate is an indirect food additive for use only as a component of adhesives.
Diisooctyl phthalate is classified as a plasticizer when migrating from food-packaging material (for foods of high water content only).
Special Reports
USEPA; Ambient Water Quality Criteria Doc: Phthalate Esters (1980) EPA 440/5-80-067
Nat'l Research Council Canada; Phthalate Esters in the Aquatic Environment (1980) NRCC No. 17583
USEPA; Health and Environmental Effects Profile for Phthalate Esters; (1980) ECAO-CIN-146
USEPA/ECAO; Atlas Document for: Phthalate Esters (1980)
For more Special Reports (Complete) data for DIISOOCTYL PHTHALATE (6 total), please visit the HSDB record page.
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenedicarboxylic acid, diisooctyl ester is included on this list. Efffective date 10/04/82; Sunset date 10/04/92.
Reactivity Profile
DI-ISOOCTYL PHTHALATE reacts exothermically with acids to generate isooctyl alcohol and phthalic acid. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by interaction with caustic solutions. Flammable hydrogen is generated by mixing with alkali metals and hydrides. Can generate electrostatic charges. [Handling Chemicals Safely, 1980. p. 250].
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diisooctyl phthalate is produced, as an intermediate or final product, by process units covered under this subpart.
Sicherheit und Schutzausrüstung
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing;Fire Extinguishing Agents: Dry chemical, carbon dioxide. (USCG, 1999)
Use water spray, foam, powder, carbon dioxide.
First Aid Measures
Fresh air, rest.
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.
Rinse mouth.
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: 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.
Toxikologische Informationen
Health Effects
Phthalate esters are endocrine disruptors. Animal studies have shown that they disrupt reproductive development and can cause a number of malformations in affected young, such as reduced anogenital distance (AGD), cryptorchidism, hypospadias, and reduced fertility. The combination of effects associated with phthalates is called 'phthalate syndrome’. (A2883)
Ecotoxicity Values
EC50; Species: Pseudokirchneriella subcapitata (Green algae); Conditions: freshwater, static, 22-24 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >130 ug/L for 96 hr; Effect: decreased population abundance /> or =95% purity/
EC50; Species: Americamysis bahia (Opossum shrimp, age < or =24 hr); Conditions: freshwater, static, 20 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >550 ug/L for 96 hr; Effect: mortality /> or =95% purity/
EC50; Species: Daphnia magna (Water flea, age < or =24 hr); Conditions: freshwater, static, 20 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >160 ug/L for 48 hr; Effect: intoxication, immobilization /> or =95% purity/
LC50; Species: Cyprinodon variegatus (Sheepshead minnow, juvenile, length 6-17 mm); Conditions: freshwater, static, 22 °C, pH 7.6-7.9, hardness 25-50 mg/L CaCO3, alkalinity 25-50 mg/L CaCO3; Concentration: >480 ug/L for 96 hr /> or =95% purity/
For more Ecotoxicity Values (Complete) data for DIISOOCTYL PHTHALATE (12 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.6X10+4(SRC), determined from a water solubility of 0.09 mg/L(2) and a regression-derived equation(3), indicates that diisooctyl phthalate is expected to be immobile in soil(SRC). Volatilization of diisooctyl phthalate from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 3.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 5.5X10-6 mm Hg(2), and water solubility(2). However, adsorption to soil is expected to attenuate volatilization(SRC). Diisooctyl phthalate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Diisooctyl phthalate is expected to biodegrade in soils based upon screening studies conducted with microbial cultures isolated from sewage and sludge with degradation ranges from 75 to 99%(4-6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.6X10+4(SRC), determined from a water solubility of 0.09 mg/L(2) and a regression-derived equation(3), indicates that diisooctyl phthalate is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 3.1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 5.5X10-6 mm Hg(2), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.5 and 25 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.3 years if adsorption is considered(4). According to a classification scheme(5), a measured BCF of 207 in Mosquito fish(6) suggests bioconcentration in aquatic organisms high(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(6). Hydrolysis is not expected to be an important process(SRC) based on estimated hydrolysis half-lives of 3.4 years and 130 days at pHs 7 and 8, respectively(7). Diisooctyl phthalate incubated for 28 days in fresh water/sediment degraded 2, <1-10, and 4% at 12, 22, and 28 °C, respectively(6).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diisooctyl phthalate, which has a vapor pressure of 5.5X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase diisooctyl 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 19 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase diisooctyl phthalate may be removed from the air by wet or dry deposition(SRC). Diisooctyl phthalate does contain chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Adverse Effects
Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.;Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.
Toxicity Summary
Phthalate esters are endocrine disruptors. They decrease foetal testis testosterone production and reduce the expression of steroidogenic genes by decreasing mRNA expression. Some phthalates have also been shown to reduce the expression of insulin-like peptide 3 (insl3), an important hormone secreted by the Leydig cell necessary for development of the gubernacular ligament. Animal studies have shown that these effects disrupt reproductive development and can cause a number of malformations in affected young. (A2883)
Ecotoxicity Excerpts
/AQUATIC SPECIES/ Chronic toxicity studies were performed with commercial phthalate esters and Daphnia magna (14 phthalates) and rainbow trout (Oncorhynchus mykiss) (6 phthalates). ...For the higher-molecular-weight phthalate esters - dihexyl phthalate (DHP), butyl 2-ethylhexyl phthalate (BOP), di-(n-hexyl, n-octyl, n-decyl) phthalate (610P), di-(2-ethylhexyl) phthalate (DEHP), diisooctyl phthalate (DIOP), diisononyl phthalate (DINP), di-(heptyl, nonyl, undecyl) phthalate (711P), diisodecyl phthalate (DIDP), diundecyl phthalate (DUP), and ditridecyl phthalate (DTDP)-the GM-MATC values ranged from 0.042 to 0.15 mg/L. Survival was equally sensitive and sometimes more sensitive than reproduction. The observed toxicity to daphnids with most of the higher-molecular-weight phthalate esters appeared to be due to surface entrapment or a mode of toxicity that is not due to exposure to dissolved aqueous-phase chemical. ...
Plant Concentrations
Diisooctyl phthalate was found in aquatic organisms June to Sept 1999 from False Harbor, Vancouver, British Columbia; green algae (Enteromorpha intestinalis) 3.85 ng/g lipid and brown algae (Nereocysitis luetkeana, Fucus gardneri) 3.19 ng/g lipid(1).
Effluent Concentrations
Effluent from a municipal waste incinerator in West Germany contained diisooctyl phthalate at a concn of 11.23 ug/cu m(1) and effluent from a hazardous waste incinerator contained concns of 371.93-454.41 ng/cu m(2). Leachate from a pesticide plant contained diisooctyl phthalate at concns of 0.015-30 mg/l(3). Diisooctyl phthalate was found in waste water effluent from a petrochemical plant at concns of not detected, 70.5, and 26.9 ug/L in July 1996, Jan 1997, and March 1997, respectively and found at not detected and 40.5 ug/L in industrial landfill leachate in Dec 1996 and March 1997(4). Diisooctyl phthalate has been identified, not quantified, in emissions of textile floor coverings(5), stack emissions of coal-burning steam plants(6) and fly ash from a municipal waste incinerator(7). Diisooctyl phthalate was identified, not quantified, in leachate from a municipal landfill in Barcelona, Spain(8).
Soil Adsorption/Mobility
The Koc of diisooctyl phthalate is estimated as 1.6X10+4(SRC), using a water solubility of 0.09 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diisooctyl phthalate is expected to be immobile in soil.
TSCA Test Submissions
The ability of diisooctyl phthalate to induce morphological transformation was evaluated in the Balb/3T3 mouse cell line (Cell Transformation Assay). Based on preliminary toxicity determinations (exposure time = 24hrs), diisooctyl phthalate, diluted with acetone, was tested at 0.13, 1.25, 4.25, 12.70 or 42.35ug/ml, resulting in a range of approximately 75% to 20% relative survival. None of the treatments produced significantly greater transformation frequencies (95% confidence level) relative to the negative control (acetone).
Diisooctyl phthalate was examined for mutagenic activity in Salmonella typhimurium tester strains TA98, TA100, TA1535 and TA1537 with and without metabolic activation provided by rat liver S9 fraction. The test article was not mutagenic in the plate incorporation assay when administered at concentrations from 10 to 2000 ug/plate in the presence and absence of activation. Toxicity data was not reported.
Regulatorische Informationen
Regulatory Information
Chemical: 1,2-Benzenedicarboxylic acid, diisooctyl ester
Hazard Traits - Reproductive Toxicity;Authoritative List - EC Annex VI CMRs - Cat. 1B;Report - if used as a fragrance or flavor ingredient
Regulation (EC) No 178/2002 (amended)
1,2-Benzenedicarboxylic acid, 1,2-diisooctyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenedicarboxylic acid, 1,2-diisooctyl 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)
Diisooctyl phthalate: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements
Diisooctyl phthalate is an indirect food additive for use only as a component of adhesives.
Diisooctyl phthalate is classified as a plasticizer when migrating from food-packaging material (for foods of high water content only).
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenedicarboxylic acid, diisooctyl ester is included on this list. Efffective date 10/04/82; Sunset date 10/04/92.
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diisooctyl phthalate is produced, as an intermediate or final product, by process units covered under this subpart.
Sicherheitsdaten
- hs_code
- 2917340090
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Butylglycolbutyl phthalate (BGBP) or diisoocytl phthalate (DIOP) was administered in diet to male Sprague-Dawley rats, beagle dogs and miniature pigs in dose of 50 mg/kg for 21-28 days before oral administration of single dose of same compound labeled with (14)C in carbonyl group. Diisoocytl phthalate was less readily metabolized than butylglycolbutyl phthalate by all species.
Strains of Mycobacterium and Nocardia isolated because of their ability to use di(2-ethylhexyl) phthalate (DEHP) as sole carbon source also grew on diethyl, diisooctyl, and butyl benzyl phthalates. As the two bacteria grew on di(2-ethylhexyl) phthalate, they excreted products that increased the solubility of di(2-ethylhexyl) phthalate and diisooctyl, dihexyl, and diisodecyl but not butyl benzyl or di-n-butyl phthalates. The solubilizer was produced by Mycobacterium sp. even when grown on a water-soluble substrate such as acetate. Addition of the solubilizer to culture media enhanced the degradation of di(2-ethylhexyl) phthalate and diisooctyl phthalate by Mycobacterium sp. and Nocardia sp. but not butyl benzyl phthalate. The extent of di(2-ethylhexyl) phthalate degradation by Mycobacterium sp. in media amended with the solubilizer was reduced and the initiation of degradation was delayed if the solubilizer was first treated with protease. The effect of protease was not a result of its toxicity to Mycobacterium or use of the enzyme preparation for growth of the organism. The results thus show that microbial products increase the solubility of certain phthalates and enhance their degradation.
Phthalate esters are first hydrolyzed to their monoester derivative. Once formed, the monoester derivative can be further hydrolyzed in vivo to phthalic acid or conjugated to glucuronide, both of which can then be excreted. The terminal or next-to-last carbon atom in the monoester can also be oxidized to an alcohol, which can be excreted as is or first oxidized to an aldehyde, ketone, or carboxylic acid. The monoester and oxidative metabolites are excreted in the urine and faeces. (A2884)
Absorption, Distribution and Excretion
In rats, dogs and miniature pigs, 50 mg/kg was administered 21-28 days before oral administration of single dose of same compound labeled with (14)C in carbonyl group. Approximately 1/2 of (14)C was excreted in rat urine and 1/2 in feces, while dogs showed 69-80% in feces, and pigs 65-86% in urine.
Verwendung und Herstellung
Uses
Used as plasticizer for polyvinyl chloride jackets for building wire, cellulosic and acrylate resins, and synthetic rubber; Also used as a penetration agent for fungicides; Permitted for use as an additive in plastics in contact with food in Italy and the US; [HSDB]
Farming (Pesticides) [Category: Industry]
PLASTICIZER FOR POLY VINYL CHLORIDE JACKETS FOR BUILDING WIRE
Plasticizer for vinyl, cellulosic and acrylate resins, and synthetic rubber.
ITS USE AS AN ADDITIVE IN PLASTICS WHICH WILL COME INTO CONTACT WITH FOOD IS PERMITTED IN ITALY AND UNITED STATES.
Phthalate esters are mainly used as plasticizers, primarily used to soften polyvinyl chloride. They are found in a number of products, including glues, building materials, personal care products, detergents and surfactants, packaging, children's toys, paints, pharmaceuticals, food products, and textiles. Phthalates are used in a variety of household applications such as shower curtains, vinyl upholstery, adhesives, floor tiles, food containers and wrappers, and cleaning materials. Personal care items containing phthalates include perfume, eye shadow, moisturizer, nail polish, liquid soap, and hair spray. (L1903)
U.S. Exports
(1972) 7.63X10+9 G (DIOCTYL PHTHALATES)
(1975) 9.26X10+9 G
(1984) 1.41X10+8 G
U.S. Production
2023: <25,000 lb;2022: <25,000 lb;2021: 100,000 - <250,000 lb;2020: 25,000 - <50,000 lb
(1972) 1.47X10+10 G
(1975) GREATER THAN 4.54X10+5 G
(1984) 1.37X10+11 G /DIOCTYL PHTHALATES/
1,2-Benzenedicarboxylic acid, diisooctyl 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#1688]
Methods of Manufacturing
Isomeric esters obtained from phthalic anhydride & the mixed octyl alcohols made by the oxo process.
DIOP is manufactured by reaction of phthalic anhydride with iso-octanol in the presence of an acid catalyst.
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
1,2-Benzenedicarboxylic acid, 1,2-diisooctyl ester: ACTIVE
1,2-Benzenedicarboxylic acid, 1,1'-(2,2-dimethyl-1,3-propanediyl) 2,2'-diisooctyl ester: INACTIVE
Compatible with vinyl chloride resins and some cellulosic resins.
MOST OF THE ISO-OCTYL ALCOHOLS USED TO MAKE ... /DI-ISO-OCTYL PHTHALATE/ ARE MIXTURES OF ISOMERS.
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