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Bis(2-ethylhexyl)adipat
DEHA · Hexanedioic acid, bis(2-ethylhexyl) ester · Diethylhexyl adipate · dioctyl · Bis(2-ethylhexyl)hexanedioate · bis(2-ethylhexyl) · Beha · hexanedioicacidbis(2-ethylhexyl)ester
Identifikatoren & physikalische Daten
| CAS No. | 103-23-1 |
|---|---|
| Summenformel | C22H42O4 |
| Durchschnittliche Molmasse | 370,6 g/mol |
| Monoisotopische Masse | 370,30830982 g/mol |
| SMILES | CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC |
| InChIKey | SAOKZLXYCUGLFA-UHFFFAOYSA-N |
| PubChem CID | 7641 |
| ChEMBL | CHEMBL1414950 |
| ChEBI | CHEBI:34675 |
| EC No. | 203-090-1 |
| DTXSID | DTXSID0020606 |
| Lokaler Name | Bis(2-ethylhexyl)adipat |
Chemische & physikalische Eigenschaften
| XLogP | 6,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 19 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 320 |
| Stoffklassen | Other Classes -> Esters, OtherCarcinogens |
| Polymers | Plastics -> PURPVC (soft)Plastics -> Plasticisers |
| Kosmetika | Cosmetics ingredient -> Conditioning/EmollientEmulsifierFlavorFragranceSolventCosmetic ingredients (Diethylhexyl Adipate) -> CIR (Cosmetic Ingredient Review)Film formingPlasticiser |
| pH | Acidity: 0.25 (meg/100 gm. max)7 (H2O, 20℃) |
| Duftstoffe | Fragrance Ingredient (Di-(2-ethylhexyl) adipate) -> IFRA transparency List |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | 8.1 |
| Geruch | SLIGHT AROMATIC SMELLOdorlessMild |
| Plasticizers | PlasticizerPlasticizers |
| Dichte | 0.923 (USCG, 1999) - Less dense than waterwill float0.922 @ 25 °C/4 °C0.922 @25 °C0.925 g/mL at 20 °C(lit.) |
| Viscosity | 13.7 cP @ 20 °C |
| Color/Form | COLORLESS OR VERY PALE AMBER LIQLight colored, oily liquid. |
| Schmelzpunkt | -67 °C |
| Siedepunkt | 417 °C |
| Pour Point | -65 |
| Dampfdruck | <0.001 hPa (20 °C) |
| Brechungsindex | n20/D 1.447(lit.) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | <0.0001g/limmiscible |
| Aggregatzustand | Liquid |
| Wichte | 0.99 |
| Farbe | Clear colorless |
| Explosionsgrenze | 0.24%(V) |
| Biologische Quelle | synthetic |
| BRN | 1803774 |
| Henry-Konstante | 2.3×101 mol/(m3Pa) at 25℃, Felder et al. (1986) |
| Stabilität | Stable. Incompatible with oxidizing agents, water, nitrates. |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING - EMOLLIENTPLASTICISERSKIN CONDITIONINGSOLVENTFILM FORMING |
| InChI | 1S/C22H42O4/c1-5-9-13-19(7-3)17-25-21(23)15-11-12-16-22(24)26-18-20(8-4)14-10-6-2/h19-20H,5-18H2,1-4H3 |
| InChIKey | SAOKZLXYCUGLFA-UHFFFAOYSA-N |
| SMILES | CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC |
| LogP (Verteilungskoeffizient) | 8.94 at 25℃ |
| CAS Datenbank | 103-23-1(CAS DataBase Reference) |
| NIST chemische Informationen | Di(2-ethylhexyl)adipate(103-23-1) |
| EPA chemische Informationen | Di(2-ethylhexyl) adipate (103-23-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 96.5% (1012 of 1049) of all reports.Not ClassifiedAggregated GHS information provided per 1049 reports by companies from 12 notifications to the ECHA C&L Inventory.WarningH410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard] |
|---|---|
| Regulatorische Informationen | Chemical: Hexanedioic acid, bis(2-ethylhexyl) esterHazard Traits - Developmental ToxicityReproductive ToxicityRegulation (EC) No 178/2002 (amended)Hexanedioic acid, 1,6-bis(2-ethylhexyl) ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanedioic acid, 1,6-bis(2-ethylhexyl) 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)REACH registered substance: Bis(2-ethylhexyl) adipate (EC: 203-090-1)Dioctyl adipate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Hexanedioic acid, bis(2-ethylhexyl) ester: Human health tier II assessment |
| Brandgefahren | Behavior in Fire: Use water spray to cool exposed containers. (USCG, 1999) |
| Brandpotenzial | SLIGHT, WHEN EXPOSED TO HEAT OR FLAMECAN REACT WITH OXIDIZING MATERIALS.Combustible |
| Gesundheitsgefahren | Liquid may cause mild eye irritation. Repeated or prolonged skin contact may cause irritation. (USCG, 1999) |
| Gefahrenübersicht | An eye irritant[HSDB] May cause effects on the central nervous system and liver[ICSC] A skin and eye irritant[MSDSonline] |
| FDA-Anforderungen | Di(2-ethylhexyl) adipate is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | DHHS/NTPCarcinogenesis Bioassay of Di(2-ethylhexyl)adipate in F344 Rats and B6C3F1 Mice (Feed Study) Technical Report Series No. 212 (1982) NIH Publication No 81-1768USEPA/ODW: Dinking Water Criteria Document for Di(2-Ethylhexyl) Adipate (1990)Final Report on the Safety Assessment of Dioctyl Adipate and Diisopropyl AdipateJ Am Coll Toxicol 3 (3): 101-30 (1984)Ashby J et alMechanistically Based Human Hazard Assessment of Peroxisome Proliferator Induced HepatocarcinogenesisHuman and Experimental Toxicology 13 (Suppl 2): S1-S117 (1994) |
| Reactivity Profile | BIS(2-ETHYLHEXYL) ADIPATE 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. [Handling Chemicals Safely 1980. p. 250]. This chemical is incompatible with oxidizing materials and water. It is also incompatible with nitrates. (NTP, 1992) |
| Flammable Limits | LOWER FLAMMABLE LIMIT: 0.4% BY VOLUME @ 242 °C |
| Air and Water Reactions | This chemical slowly hydrolyzes. Insoluble in water. |
| Brandbekämpfung | Fire Extinguishing Agents Not to Be Used: Water. |
| Erste Hilfe | 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. |
| Brandbekämpfungsverfahren | FOAM, CARBON DIOXIDE, DRY CHEM ... . |
| Lagerbedingungen | IN GENERAL, MATERIALS ... TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS ... SHOULD BE STORED IN COOL ... VENTILATED PLACE, OUT OF ... SUN, AWAY FROM ... FIRE HAZARD ... BE PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED. |
| Freisetung ohne Brand | 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. |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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. |
| Protective Action Criteria (PAC) | 27 [mg/m3]300 [mg/m3]1800 [mg/m3] |
| Personal Protective Equipment (PPE) | Wear splash goggles, impervious apron, and impervious gloves. (USCG, 1999) |
| Körperbelastung | Bis(2-ethylhexyl) adipate was detected, not quantified, in 1 of 8 tissue samples collected from persons between the ages of 0-14 years, 4 of 8 tissue samples collected from persons between the ages of 15-44 years, and 3 of 8 tissue samples collected from persons above 45 years of age(1). Bis(2-ethylhexyl) adipate was detected in 7 of 46 tissue samples collected from people between April and June, 1984 at concentrations ranging from 0.002 to 0.165 ug/g(1). |
| Cancer Sites | Hepatic |
| Zielorgane | Developmental |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49,000(SRC), determined from a structure estimation method(2), indicates that bis(2-ethylhexyl) adipate is expected to be immobile in soil(SRC). The dominant degradation process in the soil environment is expected to be microbial degradation. Biodegradation test results indicate that bis(2-ethylhexyl) adipate is readily biodegradable(3,4). Therefore, the dominant degradation process in the soil environment is expected to be microbial degradation(SRC). Volatilization of bis(2-ethylhexyl) adipate from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 4.34X10-7atm-cu m/mole(3). Bis(2-ethylhexyl) adipate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.5X10-7mm Hg(3).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49,000(SRC), determined from an estimation method(2), indicates that bis(2-ethylhexyl) adipate is expected to adsorb to suspended solids and sediment in water(SRC). Biodegradation test results indicate that bis(2-ethylhexyl) adipate is readily biodegradable(4). Therefore, the dominant degradation process in the aquatic environment is expected to be microbial degradation(4). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 4.34X10-7 atm-cu m/mole(4). According to a classification scheme(5), a BCF of 27(4), suggests the potential for bioconcentration in aquatic organisms is low. Bis(2-ethylhexyl) adipate is expected to hydrolyze producing 2-ethylhexanol and hexanoic acid(SRC). Estimated hydrolysis half-lives are 3 years and 120 days at pH values of 7 and 8, respectively(6).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bis(2-ethylhexyl) adipate, which has a vapor pressure of 8.5X10-7 mm Hg at 20 °C(3), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase bis(2-ethylhexyl) adipate 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 0.63 days(SRC), calculated from its rate constant of 2.5X10-11 cu cm/molecule-sec at 25 °C(4) determined using a structure estimation method(2). Particulate-phase bis(2-ethylhexyl) adipate may be removed from the air by wet and dry deposition(SRC). Bis(2-ethylhexyl) adipate may undergo direct photolysis in the environment, since this compound contains a functional group that can absorb light >290 nm(5). |
| Lebensmitteluntersuchungswerte | Bis(2-ethylhexyl) adipate was qualitatively detected in the aroma isolate of mango fruit(1)the source of the bis(2-ethylhexyl) adipate was migration from the PVC film in which the fruit was wrapped during storage(1). The following concns of bis(2-ethylhexyl) adipate (in mg/kg) were detected in retail foodstuffs packaged in cling-film plastic wrap(2): fresh fruits and vegetables: 0.2-6.4sandwiches: 30-212cheese: 28-135fresh pork: 1.8-64fresh lamb: 2.9-11fresh beef: 1.0-8.0fresh chicken: 8.5-53(2)draught beer had levels of 0.01-0.07 mg/kg which presumably came from plasticizer migration from plastic tubing(2)bottled beverages had levels of 0.01-0.1 mg/kg which presumably came from plastic closure seals(2). Bis(2-ethylhexyl) adipate migrations from PVC food wrap films of 41-362 mg/kg were measured for various exposures of food (sandwich, cheese, cake, chicken, biscuits) to the food wrap(3). Bis(2-ethylhexyl) adipate was detected, not quantified, in 200 g of roasted Chinese chestnuts collected from a commercial grower in Western Pennsylvania(4). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Toxizitätsübersicht | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=103-23-1] |
| Effluent Concentrations | Bis(2-ethylhexyl) adipate concns of 2-70 ppb were detected in effluent waters collected from three NJ POTW (publicly owned treatment works) that were sampled three times during a 1-yr period(1)two of the plants were in industrial areas while the third was in a rural area with no known industrial input(1)however, the rural POTW had the highest detected concn(1). Bis(2-ethylhexyl) adipate was detected in 9 of 28 wastewater samples (detection limit 1 ppb) taken from waste treatment plants, industrial effluents and polluted fiords in Norway(2). A wastewater effluent collected from a chemical plant on the Delaware River in Aug 1977 contained a bis(2-ethylhexyl) adipate concn of 2000 ppb(3). Bis(2-ethylhexyl) adipate was qualitatively detected in water samples collected from advanced waste treatment facilities in Lake Tahoe, CA (Oct 1974), Pomona, CA (Sep 1974), Orange County, CA (Jan 1976), and Washington, DC (Sep 1974)(4). Bis(2-ethylhexyl) adipate was detected in 1 of 4 air samples collected from the 700 MW power station of Flensburg, Germany at a concentration of 73,000 ng/cu nm(5). Bis(2-ethylhexyl) adipate was detected in incoming leachate samples collected from a municipal landfill in Hyllstofta, Sweden with an average concentration of 3250 ng/lafter nitrification an average concentration of 6185 ng/l was detected and after denitrification, an avg concn of 8000 ng/l was detected(6). |
| EPA IRIS Information | Di(2-ethylhexyl)adipateHepaticDevelopmental6 x 10 ^-1 mg/kg-day |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for bis(2-ethylhexyl) adipate can be estimated to be 49,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that bis(2-ethylhexyl) adipate is expected to be immobile in soil. |
| TSCA Test Submissions | The ability of di-2-ethylhexyl adipate to induce morphological transformation in the BALB/3T3 mouse cell line (Cell Transformation Assay) was evaluated. Based on preliminary clonal toxicity determinations (exposure time=72 hrs), di-2-ethylhexyl adipate, in 0.5% acetone, was tested at 3.38, 6.75, 13.5, and 27.0 nl/ml, with cell survival ranging from 89.0-31.7% relative to the solvent control. The material did not induce the appearance of a significant number of transformed foci (Bailey's modification of Student's t-test).Effects on the liver and liver lipids were evaluated in groups of male and female Fischer 344 rats (5/sex/dose) fed nominal concentrations of 0, 0.1, 0.6, 1.2, or 2.5% di-2-ethylhexyl adipate in the diet for 21 days. Toxicity was evident by statistical differences between dosed groups and control groups for: mean body weights (2.5% group, males and females), absolute and relative liver weights (0.6, 1.2 and 2.5% group females, 1.2 and 2.5% group males), relative kidney weights (1.2 and 2.5% groups male and female). There were no statistically significant differences in absolute and relative testes weights or levels of serum triglycerides and cholesterol between dosed and control groups. Liver biochemistry revealed statistically significant differences between treated and controls as indicated by an increase in cyanide-insensitive palmitoyl-CoA oxidation (1.2 and 2.5% group males, 2.5% group females), an increase in the lauric acid 12-hydroxylase activity (0.6-2.5% groups male and female), increase in lauric acid 11-hydroxylase activity (0.6 and 1.2% group males, although no clear dose response was observed), and hepatic protein levels (increased in the 2.5% group males and decreased in the 2.5% group females). There was a dose related increase in peroxisome proliferation at doses above 0.1% although the 0.6 and 1.2% group females were given equal scores.The rate of hydrolysis of di-2-ethylhexyl adipate was determined in intestinal homogenates prepared from male Sprague-Dawley rats at 37 degC in a water bath shaker. Hydrolysis was rapid with an estimated half-life of 6.0 min.The ability of di-2-ethylhexyl adipate to induce morphological transformation in the BALB/3T3 mouse cell line (Cell Transformation Assay) in the presence of added metabolic activation by Aroclor-induced rat liver S9 fraction was evaluated. Based on preliminary clonal toxicity determinations (exposure time=48 hrs), di-2-ethylhexyl adipate, in 0.5% acetone, was tested at 42, 28, 7, 0.7 and 0.07 ul/ml, with cell survival ranging from 52.3% to 11.5% relative to the solvent control. The test material did not induce the appearance of a significant number of transformed foci (Bailey's modification of Student's t-test).For more TSCA Test Submissions (Complete) data for BIS(2-ETHYLHEXYL) ADIPATE (11 total), please visit the HSDB record page. |
| Landesrichtlinien für Trinkwasser | (ME) MAINE 292 ug/l |
| Federal Drinking Water Standards | EPA 400 ug/l |
| Bundesrichtlinien für Trinkwasser | EPA 400 ug/l |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1230 3/PG 2 |
| Zollcode | 29171290 |
| RTECS-Nr. | AU9700000 |
| R-Sätze (R) | 36/38-40-39/23/24/25-23/24/25-11 |
| Toxizität | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit 8410 mg/kg |
| Gefahrensymbole | Xi,Xn,T,F |
| Sicherheitshinweise (S) | 26-36-45-36/37-16-7-24/25 |
| Gefahrenklasse | 9 |
| Verpackungsgruppe | III |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 103-23-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 350 °C DIN 51794 |
Anwendungen & Verwendung
Verwenden
Bis(2-ethylhexyl) adipate also known as dioctyl adipate (DOA) can be used as a plasticizer for improving the impact properties of polymers. DOA is also used to produce clear films for food packaging applications and in synthetic rubber industries due to its compatibility with nitrocellulose and ethylcellulose.