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1,1'-Oxydipropan-2-ol
DPG · 2-Propanol, 1,1'-oxybis- · DPGF · 2-HYDROXYPROPYL ETHER · 1,1'-oxybis(propan-2-ol) · ,’-Dihydroxy-dipropylether · dipropyleneglycol,mixtureofisomericpropyleneglycolethers · dipropylglycol
Identifikatoren & physikalische Daten
| CAS No. | 110-98-5 |
|---|---|
| Summenformel | C6H14O3 |
| Durchschnittliche Molmasse | 134,17 g/mol |
| Monoisotopische Masse | 134,0942943 g/mol |
| SMILES | CC(O)COCC(C)O |
| InChIKey | AZUXKVXMJOIAOF-UHFFFAOYSA-N |
| PubChem CID | 8087 |
| ChEMBL | CHEMBL3182176 |
| EC No. | 203-821-4 |
| DTXSID | DTXSID7026863 |
| Lokaler Name | 1,1'-Oxydipropan-2-ol |
Chemische & physikalische Eigenschaften
| XLogP | -0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 49,7 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 57 |
| Geruch | Nearly odorless |
| Dichte | 1.0252 at 20 °C/20 °CCoefficient of expansion: 0.00073/K at 20 °Cbulk density:8.5 lb/gal at 20 °C |
| Viscosity | 1.07 cP at 20 °C |
| Color/Form | Colorless, slightly viscous liquid |
| Löslichkeit | In water, 100 g/L /1X10+5 mg/L/, temperature not specifiedSoluble in tolueneMiscible with ether |
| Flammpunkt | 137.7 °C280 °F (open cup)138 °C |
| Siedepunkt | 232.8 °C229-232 °C |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | less than -40 °C |
| Dampfdichte | 4.63 (Air = 1) |
| Dampfdruck | 0.03 [mmHg]VP: 0.03 mm Hg at 25 °C (extrapolated)VP: 1 mm Hg at 73.8 °C |
| Brechungsindex | Index of refraction: 1.439 at 25 °C1.44-1.442 |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| pKa (Säurekonstante) | 14.19±0.20(Predicted) |
| Farbe | Colorless,sltly viscous liquid |
| Geruch | nearly odorless |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCEPERFUMINGVISCOSITY CONTROLLINGSOLVENT |
| InChI | InChI=1S/C6H14O3/c1-5(7)3-9-4-6(2)8/h5-8H,3-4H2,1-2H3 |
| InChIKey | AZUXKVXMJOIAOF-UHFFFAOYSA-N |
| SMILES | O(CC(O)C)CC(O)C |
| LogP (Verteilungskoeffizient) | -0.820 |
| CAS Datenbank | 110-98-5(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propanol, 1,1'-oxydi-,(110-98-5) |
| EPA chemische Informationen | Bis(2-hydroxypropyl) ether (110-98-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 97.2% (1893 of 1947) of all reports.Not ClassifiedReported as not meeting GHS hazard criteria by 1893 of 1947 companies (only 2.8% companies provided GHS information). For more detailed information, please visit ECHA C&L website.Aggregated GHS information provided per 1947 reports by companies from 6 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 1893 of 1947 reports by companies.There are 5 notifications provided by 54 of 1947 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propanol, 1,1'-oxybis-2-Propanol, 1,1'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanol, 1,1'-oxybis- 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)2-Propanol, 1,1'-oxybis-: Does not have an individual approval but may be used under an appropriate group standard |
| Brandpotenzial | Combustible when exposed to heat or flame, can react vigorously with oxidizing materials. |
| Gefahrenübersicht | A mild skin and eye irritant[ICSC] May cause irritationTargets the liver, kidneys, and nerves[MSDSonline] See Dipropylene glycol.The major hazards encountered in the use and handling of 1,1'-oxydi-2-propanol stem from its toxicologic properties. Exposure to this practically odorless, colorless, slightly viscous liquid may occur from its use as a solvent in the manufacture of printing inks, resins, plastics, and antifreeze. Effects from exposure may include liver and kidney damage, and CNS depression. In activities and situations where over-exposure may occur, wear a self-contained breathing apparatus. 1,1'-Oxydi-2-propanol is only slightly flammable and must be preheated before ignition can occur. For fires involving this substance, extinguish with dry chemical, CO2, alcohol foam, or water spray (applied gently to the surface). |
| FDA-Anforderungen | Dipropylene glycol is an indirect food additive for use only as a component of adhesives. |
| Special Reports | USEPA/Office of Prevention, Pesticides and Toxic SubstancesReregistration Eligibility Decision for Propylene Glycol and Dipropylene Glycol, EPA 739-R-06-002 (September 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of August 12, 2015: http://www.epa.gov/pesticides/reregistration/status.htm] |
| TSCA-Anforderungen | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 1/26/94Reporting date: 3/28/94. |
| EPA Safer Chemical | Chemical: 1,1'-Dimethyldiethylene glycolGreen circle - The chemical has been verified to be of low concern based on experimental and modeled data. |
| FIFRA-Anforderungen | The Agency has completed its assessment of the dietary, drinking water, residential, ecological and occupational risks associated with the use of pesticide products containing the active ingredients propylene glycol and dipropylene glycol. Based on a review of these data, the Agency has sufficient information on the human health and ecological effects of propylene glycol and dipropylene glycol to make a decision as part of the tolerance reassessment process under FFDCA and reregistration under FIFRA, as amended by FQPA. The Agency has determined that propylene glycol and dipropylene glycol containing products are eligible for reregistration.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Dipropylene glycol is found on List C. Case No: 3126Pesticide type: insecticide, fungicide, antimicrobialCase Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.Active ingredient (AI): dipropylene glycolData Call-in (DCI) Date(s): 8/2/93AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. |
| 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. |
| Hazard Classes and Categories | Not Classified |
| Skin, Eye, and Respiratory Irritations | A skin and eye irritant. |
| Hazardous Reactivities and Incompatibilities | ...can react vigorously with oxidizing materials. |
| Brandbekämpfungsverfahren | Alcohol foam, carbon dioxide, dry chemical. |
| Entsorgungsverfahren | SRP: 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 qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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. |
| Ökotoxizitätswerte | LC50Species: Xenopus laevis (African Clawed Frog) age 3-4 wkConditions: freshwater, static, 20 °CConcentration: 3181000 ug/L for 48 hr /formulation/ |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2,2'-dihydroxydi-n-propyl ester is expected to have very high mobility in soil(SRC). Volatilization of 2,2'-dihydroxydi-n-propyl ester from moist soil surfaces is not expected(SRC) given an estimated Henry's Law constant of 3.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(2). 2,2'-Dihydroxydi-n-propyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 1% of theoretical BOD using activated sludge in the Japanese MITI test(3) suggests that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that 2,2'-dihydroxydi-n-propyl ester 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 3.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). 2,2'-Dihydroxydi-n-propyl ester is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(4), BCFs of <2.2-4.6 and 0.3-1.4 reported in carp (Cyprinus carpio) exposed over a 6 week period to 0.3 and 3 mg/L of 2,2'-dihydroxydi-n-propyl ester(5), respectively, suggest bioconcentration in aquatic organisms is low(SRC). A 1% of theoretical BOD using activated sludge in the Japanese MITI test(5) suggests that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2'-dihydroxydi-n-propyl ester, which has an estimated vapor pressure of 6.3X10-3 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 2,2'-dihydroxydi-n-propyl ester 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 12 hours(SRC), calculated from its rate constant of 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). 2,2'-Dihydroxydi-n-propyl ester does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Toxizitätsübersicht | IDENTIFICATION AND USE: 1,1'-Oxydi-2-propanol is a colorless slightly viscous liquid that is nearly odorless. Commercial dipropylene glycol is composed of 3 isomers and is typically 98% pure. The commercial product is typically composed of up to 48% of the isomer 1,1'-oxydi-2-propanol. 1,1'-Oxydi-2-propanol is registered for use as an approved pesticide in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. It is also used as a solvent and in the production of polyester and alkyd resins, reinforced plastics, and plasticizers. Uses for dipropylene glycol include in printing industry, in antifreeze, and air sanitation, since its vapor is highly germicidal. HUMAN EXPOSURE AND TOXICITY: There is no human toxicity data reported for 1,1'-oxydi-2-propanol. ANIMAL STUDIES: All toxicity data reported is for the related chemical dipropylene glycol. Although more acutely depressant to the central nervous system than ethylene, diethylene or propylene glycol, dipropylene glycol is still low in toxicity to animals, especially to the liver. It is not irritating to the skin and is not absorbed in toxic amounts through intact skin. Dipropylene glycol did cause death from kidney injury when administered at 10%. Chronic administration to rats caused degeneration of tubular epithelium in the kidneys and liver degeneration of parenchyma. In dogs, repeated gastric dosage of dipropylene glycol resulted in moderate degenerative changes in kidney and only minimal evidence of liver damage. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,2'-dihydroxydi-n-propyl ester can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2'-dihydroxydi-n-propyl ester is expected to have very high mobility in soil. |
| Artificial Pollution Sources | 2,2'-Dihydroxydi-n-propyl ester's production and use in hydraulic and brake fluids, inks, paint and as a plasticizer and lubricant(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: 2,2'-Dihydroxydi-n-propyl ester, present at 100 mg/L, reached 1% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). |
| Environmental Bioconcentration | BCFs of <2.2-4.6 and 0.3-1.4 were reported in carp (Cyprinus carpio) exposed over a 6 week period to 0.3 and 3 mg/L of 2,2'-dihydroxydi-n-propyl ester, respectively(1). According to a classification scheme(2), these BCFs suggest bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for 2,2'-dihydroxydi-n-propyl ester is estimated as 3.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2'-dihydroxydi-n-propyl ester is expected to be essentially nonvolatile from moist soil and water surfaces(2). 2,2'-Dihydroxydi-n-propyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-3 mm Hg(SRC), determined from a fragment constant method(1). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Acute: /SRP: CNS depression/ was produced in dogs by iv injection of 5.9 mL/kg ... chronic: depression of running activity occurred in rats given 12% in diet for 15 wk ... in contrast to incr activity produced by propylene glycol. /Dipropylene glycol//LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... By oral admin, for rats: addition to drinking water of 5% for 77 days had no injurious effect10% was followed by death of some animals from kidney injury ... . /Dipropylene glycol//LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Chronic: kidney of rats showed ... hydropic degeneration of tubular epithelium, & liver degeneration of parenchyma, but these lesions were less severe & less uniformly produced than with diethylene glycol. /Dipropylene glycol//LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Chronic: dogs ... after survival of repeated gastric dosage of dipropylene glycol showed only moderate degenerative changes in kidney & only minimal evidence of liver damage. /Dipropylene glycol//OTHER TOXICITY INFORMATION/ Although more acutely depressant to /central nervous system/ CNS than ethylene, diethylene or propylene glycol, dipropylene glycol is still low in toxicity to animals, especially to the liver. It is not irritating to the skin & not absorbed in toxic amt through intact skin. /Dipropylene Glycol/ |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of 2,2'-dihydroxydi-n-propyl ester with photochemically-produced hydroxyl radicals has been estimated as 3.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,2'-Dihydroxydi-n-propyl ester is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,2'-Dihydroxydi-n-propyl ester does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Probable Routes of Human Exposure | According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimates the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of 2,2'-dihydroxydi-n-propyl ester in the United States may be 25-49 workers per plantthe data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).NIOSH (NOES Survey 1981-1983) has statistically estimated that 3536 workers (1385 of these are female) were potentially exposed to 1,1-oxydi-2-propanol in the US(1). Occupational exposure to 2,2'-dihydroxydi-n-propyl ester may occur through inhalation and dermal contact with this compound at workplaces where 2,2'-dihydroxydi-n-propyl ester is produced or used. Monitoring data indicate that the general population may be exposed to 2,2'-dihydroxydi-n-propyl ester via ingestion of contaminated drinking water, and dermal contact with consumer products containing 2,2'-dihydroxydi-n-propyl ester(SRC). |
| Environmental Water Concentrations | DRINKING WATER: 2,2'-Dihydroxydi-n-propyl ester was qualitatively detected in drinking water concentrates collected in Cincinnati, OH on Oct 17, 1978 and Jan 14, 1980(1).GROUND WATER: 2,2'-Dihydroxydi-n-propyl ester was qualitatively detected in ground water samples collected from a well adjacent to a landfill facility in Norman, OK. The occurrence of 2,2'-dihydroxydi-n-propyl ester in the well water is probably the result of leaching from the landfill(1). |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29094400 |
| RTECS-Nr. | UB8785000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orl-rat: 14,850 mg/kg 34ZIAG -,731,69 |
| Sicherheitshinweise (S) | 24/25 |
| Gefahrstoffdaten | 110-98-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
1,1'-Oxydi-2-propanol is commonly used as a plasticizer, an intermediate in industrial chemical reactions.