HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Hexan-6-olid
CAPROLACTONE · 2-OXEPANONE · oxepan-2-one · Oxepanone · EPSILON-CAPROLACTONE · E-CAPROLACTONE · 6-HEXANOLACTONE · Polycaprolactone Polyol
Identifikatoren & physikalische Daten
| CAS No. | 502-44-3 |
|---|---|
| Summenformel | C6H10O2 |
| Durchschnittliche Molmasse | 114,14 g/mol |
| Monoisotopische Masse | 114,06807956 g/mol |
| SMILES | O=C1CCCCCO1 |
| InChIKey | PAPBSGBWRJIAAV-UHFFFAOYSA-N |
| PubChem CID | 10401 |
| ChEMBL | CHEMBL373123 |
| ChEBI | CHEBI:17915 |
| EC No. | 207-938-1 |
| DTXSID | DTXSID4027159 |
| Lokaler Name | Hexan-6-olid |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 88,5 |
| Stoffklassen | Other Classes -> Lactones |
| SpringerMaterials Properties | Coriolis coupling |
| LogP (Verteilungskoeffizient) | log Kow= 1.215 (calc)0.68 |
| Dichte | 1.07 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001.0761 @ 20°C1.03 g/mL at 25 °C(lit.) |
| Löslichkeit | Solubility in water: miscibleChloroform, Ethyl Acetate>1000 MG/L (20 ºC) |
| Flammpunkt | 127 °C o.c.229 °F |
| Siedepunkt | 237 °C215 °C @760 [mm Hg]96-97.5 °C10 mm Hg(lit.) |
| Schmelzpunkt | -1.5 °C-1 °C |
| Dampfdichte | Relative vapor density (air = 1): 3.93.9 (vs air) |
| Dampfdruck | 0.13 [mmHg]1.35X10-1 mm Hg at 25 °CVapor pressure, Pa at 25 °C: 0.80.01 [mm Hg] @20 °C0.01 mm Hg ( 20 °C) |
| Food Contact Substances | FCS -> FDA Cumulative Estimated Daily Intake (CEDI) |
| Physical Description | CBILiquidColorless liquidMiscible in water[eChemPortal: SIDSUNEP] Colorless liquid[MSDSonline]COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR. |
| Brechungsindex | n20/D 1.463(lit.) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| Farbe | Clear colorless, yellowing on aging |
| Explosionsgrenze | 1.2-9%(V) |
| BRN | 106919 |
| Henry-Konstante | 5.5×10-2 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2 |
| InChIKey | PAPBSGBWRJIAAV-UHFFFAOYSA-N |
| SMILES | O=C1CCCCCO1 |
| LogP (Verteilungskoeffizient) | 0.32 at 20℃ |
| CAS Datenbank | 502-44-3(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Oxepanone(502-44-3) |
| EPA chemische Informationen | 2-Oxepanone (502-44-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 34.5% (266 of 770) of reports.WarningH319 (60.1%): 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 770 reports by companies from 8 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: 2-OxepanoneCouncil Directive (EEC) No 109/1989 (Repealed by Reg. EC No 1935/2004 (amended))2-Oxepanone is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Oxepanone 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: 07-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14740Caprolactone: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. |
| Gefahrenübersicht | Emergency treatment: irritants[HSDB] Rapidly hydrolyzed in the body to 6-hydroxyhexanoic acid and rapidly excreted in urineIrritating to eyesNo adverse effects in a 9-day inhalation study at 45 ppmNo evidence of reproductive effects[ToxPlanet: UNEP: SIDS] An irritant[MSDSonline] |
| Chemical Dangers | Reacts with strong bases, strong acids and strong oxidants. |
| Hazard Classes and Categories | Eye Irrit. 2A (60.1%) |
| Explosive Limits and Potential | Explosive limits , vol% in air: 1.2-9 |
| Brandbekämpfung | Use powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse skin with plenty of water or shower.Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention.Rinse mouth. |
| Sichere Lagerung | Separated from strong bases, strong acids and strong oxidants. Dry. Well closed. |
| Verschüttetes entsorgen | Personal protection: safety goggles. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | Evaporation at 20 °C is negligiblea nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying. |
| Skin Prevention | Protective gloves. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Inhalation Prevention | Use ventilation. |
| Effects of Short Term Exposure | The substance is irritating to the eyes. |
| Protective Action Criteria (PAC) | 13 [mg/m3]140 [mg/m3]850 [mg/m3] |
| Umweltverhalten | TERRESTRIAL FATE: There are no biodegradation studies in soil to indicate whether biodegradation of caprolactone may be significant. An estimated Koc value of 109.1(1) suggests high mobility in soil(2,SRC).AQUATIC FATE: Volatilization half-lives for caprolactone of 0.35 and 3.9 days have been estimated for a model river (one meter deep) and a model environmental pond, respectively(1-2). An estimated Koc of 109.1 and BCF of 4.94 for caprolactone indicate that adsorption to sediment and bioconcentration in aquatic organisms are not important fate processes(1). No information on biodegradation of caprolactone was available(SRC).ATMOSPHERIC FATE: Based on a measured vapor pressure of 1.35X10-1 mm Hg at 25 °C(1), caprolactone can be expected to exist almost entirely in the vapor-phase in the ambient atmosphere(SRC). Vapor-phase caprolactone is degraded slowly in the ambient atmosphere by reaction with photochemically formed hydroxyl radicalsthe half-life for this reaction in air can be estimated to be about 2.76 days(2,SRC). |
| Signs and Symptoms | Redness. Pain. |
| Effluent Concentrations | Caprolactone was qualitatively identified in advanced waste water treatment concentrates from Pomona, CA(1-2). |
| Soil Adsorption/Mobility | Based on a calculated log Kow of 1.215(1), the Koc for caprolactone can be estimated to be approximately 109.1(2,SRC). This Koc value indicates that caprolactone has high mobility in soil(3). |
| Human Toxicity Excerpts | The efficacy, safety and patient acceptance of a subcutaneous implant of levonorgestrel contained in a biodegradable capsule of poly (E-caprolactone) wax are reported in 48 women, aged 18-40 yr, 32 of whom were given an implant containing a 21.6 mg dose of levonorgestrel, and 16 were initially given an implant containing 12 mg of levonorgestrelpatients were followed up for one yr. Ovulation occurred in all cycles in patients given the 12 mg dose, and in 26.3% of cycles in the group given 21.6 mg. Levonorgestrel blood levels were significantly lower in those given 12 mg. All patients initially given 12 mg were given a second implant of the same dose. Bleeding patterns were regular in most women who ovulated and irregular in most remaining subjects. It was assumed that changes in cervical mucus and the endometrium contributed to effective contraception despite the frequency of ovulation. |
| Artificial Pollution Sources | As a reaction product of peracetic acid and cyclohexanone(1) and during its use as an intermediate or diluent(1), caprolactone may be released to the environment as emissions or in waste streams(SRC). |
| Environmental Bioconcentration | Based on a calculated log Kow of 1.215(1), the BCF for caprolactone can be estimated to be 4.94 using a recommended regression derived equation(2,SRC). This BCF value indicates that bioconcentration of caprolactone in aquatic organisms is not significant(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for caprolactone can be estimated to be 1.809X10-4 atm-cu m/mole at 25 °C(1,SRC). Using this value of Henry's Law constant, one estimates that the volatilization half-life of caprolactone from a model river 1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec has been estimated to be approximately 0.35 days(2,SRC). The volatilization half-life of caprolactone from a model environmental pond can be estimated to be approximately 3.9 days(3,SRC). |
| Non-Human Toxicity Excerpts | THE MUTAGENIC ACTIVITES OF 79 CARCINOGENS, NONCARCINOGENS, & STRUCTURALLY RELATED CMPD TOWARD SALMONELLA TYPHIMURIUM & SACCHAROMYCES CEREVISIAE D3 STRAINS WERE INVESTIGATED IN THE IP HOST-MEDIATED ASSAY. EPSILON-CAPROLACTONE WAS NOT MUTAGENIC TOWARD SALMONELLA TYPHIMURIUM STRAINS TA1530 OR TA1535 IN THE HOST-MEDIATED ASSAY, AND DID NOT INCREASE MITOTIC RECOMBINATION IN SACCHAROMYCES CEREVISIAE D3.OF 13 DIRECT-ACTING ALKYLATING AGENTS, ONLY ONE NONCARCINOGEN, EPSILON-CAPROLACTONE, WAS TESTED IN THE SYRIAN HAMSTER EMBRYO CELL TRANSFORMATION SYSTEM, & IT YIELDED NEGATIVE RESULTS IN BOTH IN VITRO SYSTEMS. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of caprolactone with photochemically produced hydroxyl radicals has been estimated to be 5.81X10-12 cu cm/molecule-sec at 25 °C(1) which corresponds to an atmospheric half-life of about 2.76 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). |
| Probable Routes of Human Exposure | In occupational settings, exposure to caprolactone may occur through inhalation of vapors and through eye and skin contact. (SRC) |
| Environmental Fate/Exposure Summary | Caprolactone may be released to the environment during its use as an intermediate in the manufacture of caprolactam, adhesives, urethane coatings and elastomers, solvents, synthetic fibers, as a diluent for epoxy resins, during organic synthesis, and as a reaction product of peracetic acid and cyclohexanone. If released to the atmosphere, caprolactone is degraded slowly by reaction with photochemically produced hydroxyl radicals (estimated half-life of 2.76 days in air). A calculated Koc value of 109.1 suggests a high mobility of caprolactone in soil. A calculated BCF of 4.94 for caprolactone indicates that its bioconcentration in aquatic organisms should not be important. Based on a calculated Henry's Law constant of 1.809X10-4 atm cu-m/mole at 25 °C, and half-lives of 3.9 and 0.35 days from a model environmental pond and a model river, respectively, caprolactone is expected to volatilize rapidly from water. In occupational settings, exposure to caprolactone may occur through inhalation of vapors and through eye and skin contact. (SRC) |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29322090 |
| RTECS-Nr. | MO8400000 |
| R-Sätze (R) | 37/38-41-36/38 |
| Toxizität | LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-39-37/39 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 502-44-3(Hazardous Substances Data) |
| Gefahrenklasse | Eye Irrit. 2 |
| Selbstentzündungstemperatur | 204 °C |
Anwendungen & Verwendung
Verwenden
ε-Caprolactone is widely used as a monomer in the manufacturing of highly specialized polymers. It is mainly utilized as a precursor to caprolactam. It finds an application in the synthesis of polyglecaprone, which is used as a suture material in surgery.