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Diisopropylether
DIPE · DIISOPROPYL ETHER · ISOPROPYL ETHER · 2-ISOPROPOXYPROPANE · Diisopropyl ethe · Isoprpyl ether · Diisoproyl ether · 2,2'-Oxybispropane
Identifikatoren & physikalische Daten
| CAS No. | 108-20-3 |
|---|---|
| Summenformel | C6H14O |
| Durchschnittliche Molmasse | 102,17 g/mol |
| Monoisotopische Masse | 102,10446507 g/mol |
| SMILES | CC(C)OC(C)C |
| InChIKey | ZAFNJMIOTHYJRJ-UHFFFAOYSA-N |
| PubChem CID | 7914 |
| ChEMBL | CHEMBL3185565 |
| EC No. | 203-560-6 |
| DTXSID | DTXSID4021890 |
| Lokaler Name | Diisopropylether |
Chemische & physikalische Eigenschaften
| XLogP | 1,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 9,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 33,4 |
| Stoffklassen | Flammable agents - 3rd degreeVolatile Organic Compound (VOC) |
| Solvents | Solvents -> Ethers (<C12) |
| SpringerMaterials Properties | Schoenflies notation |
| LogP (Verteilungskoeffizient) | log Kow= 1.521.94 |
| Geruch | Sweet, slightly sharp, pungent like camphor and ethyl etherThe odor is more irritating and less pleasant than that of ethyl ether.Sharp, sweet, ether-like odor. |
| Dichte | 0.724 at 68 °F (USCG, 1999) - Less dense than waterwill float0.7258 @ 20 °C/4 °CBulk density: 6.05 lb/gal @ 15.5 °Csimilar to ethyl ether in properties but does tend to form peroxides more readily than ethyl etherRelative density (water = 1): 0.70.730.719 @25 °C0.725 g/mL at 25 °C(lit.) |
| Viscosity | 0.273 centipoise at 20 °F |
| Color/Form | Colorless volatile liquidColorless liquid. |
| Löslichkeit | 0.2 % (NIOSH, 2024)Sol of commercial grade in water, 1.71% @ 19 °Cmiscible with most organic solvents.Sol in acetonemiscible in ethyl alcohol, ethyl etherMISCIBLE WITH MOST ORG SOLVENTSWater solubility = 8,800 mg/l @ 20 °CSoluble in oxygenated solvents3.11g/l9 g/L (20 ºC) |
| Flammpunkt | -18 °F (USCG, 1999)-28 °C-18 °F (-28 °C) (closed cup)−29 °F |
| Siedepunkt | 156 °F at 760 mmHg (USCG, 1999)68.5 °C69 °C154 °F68.5 °C @760 [mm Hg]68-69 °C(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| Schmelzpunkt | -85.5 °C |
| Dampfdichte | 3.5 (vs air) |
| Dampfdruck | 120 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.367(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | APHA: ≤25 |
| Geruch | Sweet, slightly sharpcharacteristic pungentethereallike amphor and ethyl ether. |
| pH | 7 (20°C) |
| Explosionsgrenze | 1-21%, 100°F |
| Spezifische Wärmekapazität | Cp(liquid): 2.12 J/(g·K), at 25℃ |
| Merck | 14,5212 |
| BRN | 1731256 |
| Henry-Konstante | 2.57 at 25 °C (headspace-GC, Arp and Schmidt, 2004) |
| Dielektrizitätskonstante | 3.9(25℃) |
| Stabilität | Extremely flammable. This material is a serious fire and explosion risk. Vapour may travel considerable distances to an ignition source, which need not be an open flame, but may be a hot plate, steam pipe, etc. Vapour may be ignited by the static electricty which can build up when isopropyl ether is being poured from one vessel |
| InChI | 1S/C6H14O/c1-5(2)7-6(3)4/h5-6H,1-4H3 |
| InChIKey | ZAFNJMIOTHYJRJ-UHFFFAOYSA-N |
| SMILES | CC(C)OC(C)C |
| LogP (Verteilungskoeffizient) | 2.4 at 20℃ |
| Oberflächenspannung | 17.74mN/m at 293.15K |
| CAS Datenbank | 108-20-3(CAS DataBase Reference) |
| NIST chemische Informationen | Diisopropyl ether(108-20-3) |
| EPA chemische Informationen | Isopropyl ether (108-20-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 0.4% (1 of 265) of reports.H225 (99.6%): Highly Flammable liquid and vapor [Danger Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: Propane, 2,2'-oxybis-Propane, 2,2'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2,2'-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)Status: Active Update: 13-01-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/15860Propane, 2,2'-oxybis-: HSNO Approval: HSR001131 Approved with controlsThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. Containers may explode when heated. (USCG, 1999)· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Highly flammable. Vapour/air mixtures are explosive. |
| Brandpotenzial | FLAMMABLE LIQUID.ONLY ELECTRICAL EQUIPMENT OF EXPLOSION-PROOF TYPE (GROUP C CLASSIFICATION) IS PERMITTED TO BE OPERATED IN ETHER AREAS. ETHER SHOULD NOT BE STORED NEAR POWERFUL OXIDIZERS OR IN AREAS OF HIGH FIRE HAZARD. /ETHERS/ |
| Gesundheitsgefahren | Inhalation causes anesthesia, nausea, headache, dizziness, and irritation of the eyes and nose. Contact of liquid with eyes causes only minor injuryrepeated contact with skin will remove natural oils and may cause dermatitis. (USCG, 1999)· Inhalation or contact with material may irritate or burn skin and eyes. |
| Gefahrenübersicht | The odor is more irritating and less pleasant than that of ethyl ether. [ACGIH] A skin, eye, and respiratory tract irritantInhalation of high concentrations can cause CNS depression[ICSC] |
| DOT-Nummer und Handbuch | 1159 127 |
| Reaktive Gruppe | Ethers |
| EG-Einstufung | Symbol: FR: 11-19-66-67S: (2)-9-16-29-33Note: C |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: II |
| Reactivity Alerts | Highly Flammable |
| OSHA Standards | Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 500 ppm (2100 mg/cu m). |
| Brandbekämpfung | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Use water spray, AFFF, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Rest. Refer for medical attention . |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| Erste Hilfe | Excerpt from NIOSH Pocket Guide for Isopropyl ether:General First Aid:(General first aid procedures) |
| Sichere Lagerung | Fireproof. Cool. Keep in the dark. Keep in a well-ventilated room. Store only if stabilized. |
| Firefighting Hazards | VAPORS ARE HEAVIER THAN AIR & MAY TRAVEL TO A SOURCE OF IGNITION & FLASH BACK. LIQUID FLOATS ON WATER & MAY TRAVEL TO A SOURCE OF IGNITION & SPREAD FIRE. ETHER TENDS TO FORM UNSTABLE, EXPLOSIVE PEROXIDES ON STANDING. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).200.0 [ppm] |
| Brandbekämpfungsverfahren | Alcohol foam, CO2, foam, dry chemical. |
| Lagerbedingungen | Store in cool, dry, well-ventilated location. Separate from acids & oxidizing materials. |
| Reinigungsverfahren | 1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quantities, absorb on paper towels. Evaporate in a safe place (such as fume hood). Allow sufficient time for evaporating vapors to completely clear the hood ductwork. Burn the paper in a suitable location away from combustible materials. Large quantities can be reclaimed or collected and atomized in a suitable combustion chamber. |
| Freisetung ohne Brand | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| 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.Isopropylether may be disposed of by atomizing in a suitable combustion chamber.Isopropyl ether is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration.The following wastewater treatment technologies have been investigated for isopropyl ether: Concentration process: Biological treatment.For more Disposal Methods (Complete) data for ISOPROPYL ETHER (8 total), please visit the HSDB record page. |
| Zielorgane | Eyes, skin, respiratory system, central nervous system |
| Ökotoxizitätswerte | LC50 Pimephales promelas (fathead minnow) 91.7 mg/l 96 hr flow-through bioassay, wt 0.12 g, water hardness 45.5 mg/l CaCO3, temp: 25 + or - 1 °C, pH 7.5, dissolved oxygen greater than 60% of saturation |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a log Kow of 1.52(2) and a regression-derived equation(3), indicates that isopropyl ether is expected to have high mobility in soil(SRC). Volatilization of isopropyl ether from moist soil surfaces is expected to be important(3,SRC) given an estimated Henry's Law constant of 2.3X10-3 atm-cu m/mole(SRC), calculated from its water solubility(4) and vapor pressure(5). The potential for volatilization of isopropyl ether from dry soil surfaces may exist(SRC) based on a vapor pressure of 149 mm Hg(5). Isopropyl ether is not expected to hydrolyze in soil due to lack of hydrolyzable functional groups(3). Aqueous screening test data from studies using activated sludge or sewage inocula(6,7) suggest that isopropyl ether may be resistant to biodegradation in environmental media(SRC). Many ethers are known to be resistant to biodegradation(8).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 160(SRC), determined from a log Kow of 1.52(2) and a regression-derived equation(3), indicates that isopropyl ether is not expected to adsorb to suspended solids and sediment in water(SRC). Isopropyl ether is expected to volatilize rapidly from water surfaces(3,SRC) based on an estimated Henry's Law constant of 2.3X10-3 atm-cu m/mole(SRC), calculated from its water solubility(4) and vapor pressure(5). Estimated volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(3,SRC). Isopropyl ether is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Isopropyl ether will not significantly photooxidize via reaction with photochemically produced hydroxyl radicals in the water(6). According to a classification scheme(7), an estimated BCF of 8(3,SRC), from isopropyl ether's log Kow(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Isopropyl ether may be resistant to biodegradation in environmental media based upon screening test data from studies using activated sludge or sewage inocula(8,9,SRC). Many ethers are known to be resistant to biodegradation(10).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl ether, which has a vapor pressure of 149 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropyl ether 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 21 hours(3,SRC). The half-life for the reaction of isopropyl ether with nitrate radicals is estimated as 9 seconds(4,SRC). Direct photolysis will not be an important removal process since aliphatic ethers do not absorb light at wavelengths >290 nm(5). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour.inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Drowsiness. Sore throat.Dry skin. Redness.Further see Inhalation.irritation eyes, skin, noseresp discomfortdermatitisIn Animals: drowsiness, dizziness, unconsciousness, narcosis |
| Effluent Concentrations | Isopropyl ether has been detected in 10 out of 63 samples of industrial effluents collected from a wide variety of industries across the USA (dates not reported)(1). Six of the positive samples contained <10 ug/L isopropyl ether, 3 samples contained 10-100 ug/L and 1 sample contained >100 ug/L(1). Samples of landfill gas from an unspecified landfill which had for more than 15 months accepted municipal and industrial solid wastes and unspecified liquid wastes contained 220 mg/cu m isopropyl ether(2). |
| Medical Surveillance | Employees should be screened for history of certain medical conditions /chronic respiratory disease or skin disease/ which might place the employee at increased risk from isopropylether exposure. In persons with impaired pulmonary function, especially those with obstructive airway diseases, the breathing of isopropylether might cause exacerbation of symptoms due to its irritant properties. Isopropylether is a defatting agent and can cause dermatitis on prolonged exposure. Persons with existing skin disorders may be more susceptible to the effects of this agent. Any employee developing the above-listed conditions should be referred for further medical examination. /Chronic respiratory disease or skin disease/ |
| Soil Adsorption/Mobility | The Koc of isopropyl ether is estimated as approximately 160(SRC), using a log Kow of 1.52(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that isopropyl ether is expected to have high mobility in soil(SRC). |
| Atmospheric Concentrations | Isopropyl ether was identified, but not quantified, at 4 of 7 sites in the Kanawha Valley, WV, sampled in Sept 1977(1). |
| Human Toxicity Excerpts | Toxic symptoms similar to ethyl ether.MILDLY IRRITATING TO SKIN, MUCOUS MEMBRANES. INHALATION OF HIGH CONCENTRATIONS CAUSES /CNS DEPRESSION/, UNCONSCIOUSNESS. DEATH MAY OCCUR DUE TO RESP PARALYSIS. /ETHYL ETHER/Isopropyl ether has an anesthetic action very much like ethyl ether, but is somewhat more toxic.Human exposure to 500 ppm over a 15 min period caused no irritation, but irritation of the eyes and nose was noted at 800 ppm for 5 min with some respiratory discomfort. Industrial exposure has caused but few cases of death or serious injury. Repeated skin contact would be expected to cause dermatitis.... a group of subjects exposed for 15 minutes at 500 ppm did not consider the exposure to be irritating. At a concentration of 300 ppm, however, about one-third of the subjects objected to the unpleasant odor, while at 800 ppm for five minutes most subjects reported irritation of the eyes and nose. |
| Artificial Pollution Sources | Isopropyl ether's production and use as an extraction agent and as a solvent in paints/stain removers(1) may result in its release to the environment through various waste streams(SRC). |
| Landesrichtlinien für Trinkwasser | (NH) NEW HAMPSHIRE 120 ug/L |
| F | 10 |
| Berufliche Expositionsstufe (OEB) | A |
| Arbeitsplatzgrenzwert (OEL) | TWA: 500 ppm (2100 mg/m3) |
| Wassergefährdungsklasse (WGK) | 1 |
| Sofort lebensgefährliche Konzentration | 1,400 ppm [10% LEL] |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1159 |
| Zollcode | 2909 19 90 |
| RTECS-Nr. | TZ5425000 |
| R-Sätze (R) | 11-19-66-67-52/53 |
| Toxizität | LD50 in 14 day old, young adult, adult rats (ml/kg): 6.4, 16.5, 16.0 orally (Kimura) |
| Gefahrensymbole | F |
| Sicherheitshinweise (S) | 9-16-29-33-61 |
| Gefahrenklasse | 3Flam. Liq. 2STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 108-20-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 827 °F |
Anwendungen & Verwendung
Beschreibung
Diisopropyl ether [108-20-3], also known as 2-isopropoxyisopropane or isopropyl ether, is a clear, colorless, mobile, highly flammable liquid with a characteristic ethereal odor. Its solubility in water is low, but it is soluble in organic solvents and readily forms explosive peroxides. It has a higher boiling point, a lower vapor pressure, and a lower water solubility than diethyl ether, which means that diisopropyl ether can be recovered without significant loss after use as a solvent or as an extractant.
Verwenden
Isopropyl ether is used as a solvent for oils,waxes, resins, and dyes; and as a varnishremover.
Herstellung & Synthese
synthetische
Diisopropyl ether can be prepared by liquid-phase dehydration of 2-propanol at 130 – 190°C and 1.96– 7.85 MPa over acidic catalysts containing aluminum.