StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Verbindung

Hexan-6-olid

epsilon-CAPROLACTONE

HCID 10401
Neue NotizNeue ReaktionAnfrage stellen
Druckvorschau

Daten werden ergänzt – lade die Seite später neu, um den aktuellen Stand zu sehen

GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
502-44-3
Standard-SMILES
O=C1CCCCCO1
InChIKey
PAPBSGBWRJIAAV-UHFFFAOYSA-N
Summenformel
C6H10O2
Durchschnittliche Molmasse
114,14 g/mol
Monoisotopische Masse
114,06807956

Überblick

Hexano-6-lactone is a -lactone that is oxepane substituted by an oxo group at position 2.

Namen und Bezeichner

Bevorzugter Name
epsilon-CAPROLACTONE
IUPAC
oxepan-2-one
Lokaler Name
Hexan-6-olid
Englischer Name
ε-Caprolactone
Summenformel
C6H10O2
Molmasse
114.14

Namen und Synonyme

Epsilon-caprolactoneCAPROLACTONE502-44-36-Hexanolactone2-Oxepanonehexano-6-lactone6-Hexanolide1,6-Hexanolide1-Oxa-2-oxocycloheptanePlaccel M6-Hydroxyhexanoic acid lactoneHexanoic acid, epsilon-lactone
Weitere Namen anzeigen
oxepan-2-oneOxepanoneE-CAPROLACTONEPolycaprolactone Polyol6-CAPROLACTONE6-Hydroxyhexan-6-olide
Hexamethylene oxide, 2-oxo-epsilon-KaprolaktonDTXSID4027159epsilon caprolactoneCHEBI:17915TONE ECEQHexanoic acid, 6-hydroxy-, epsilon-lactone56RE988L1R

Datenbank-Bezeichner

CAS
502-44-3
PubChem CID
10401
DTXSID
DTXSID4027159
ChEMBL
CHEMBL373123
ChEBI
CHEBI:17915
UNII
56RE988L1R
EC Number
207-938-1
Nikkaji
J1.566K

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
0
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
8
Formalladung
0
Komplexität
88,5

Experimentelle und physikochemische Eigenschaften

Chemical ClassesOther Classes -> Lactones
SpringerMaterials PropertiesCoriolis coupling
LogP · 2 Einträge

log Kow= 1.215 (calc)

0.68

Density · 3 Einträge

1.07 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.00

1.0761 @ 20°C

SolubilitySolubility in water: miscible
Flash Point127 °C o.c.
Boiling Point · 2 Einträge

237 °C

215 °C @760 [mm Hg]

Melting Point · 2 Einträge

-1.5 °C

-1 °C

Vapor DensityRelative vapor density (air = 1): 3.9
Vapor Pressure

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 34.5% (266 of 770) of reports.

Warning

H319 (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.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 2-Oxepanone

Council 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/14740

Caprolactone: Does not have an individual approval but may be used under an appropriate group standard

Fire HazardsCombustible.
Hazards Summary · 1 Eintrag

Emergency treatment: irritants; [HSDB] Rapidly hydrolyzed in the body to 6-hydroxyhexanoic acid and rapidly excreted in urine; Irritating to eyes; No adverse effects in a 9-day inhalation study at 45 ppm; No evidence of reproductive effects; [ToxPlanet: UNEP: SIDS] An irritant; [MSDSonline]

Chemical DangersReacts with strong bases, strong acids and strong oxidants.
Hazard Classes and CategoriesEye Irrit. 2A (60.1%)

Chemie und Industrie

Pharmakologische Informationen

Mechanism of ActionCAPROLACTONE INHIBITED PROTEOLYTIC & FIBRINOLYTIC ACTIVITIES OF HUMAN PLASMIN. IN VERY LOW CONCN, IT ALSO INHIBITED ACTIVATION OF PLASMINOGEN THROUGH PLASMIN-STREPTOKINASE ACTIVATOR & HUMAN UROKINASE.

Verwendung und Herstellung

Uses · 3 Einträge

Used as a solvent, a diluent for epoxy resins, and an intermediate in adhesives, urethane coatings, and elastomers; [Hawley] Used in the production of polymers (polycaprolactones); [eChemPortal: SIDSUNEP]

Plastic Composites Manufacturing [Category: Industry]

INTERMEDIATE IN ADHESIVES, URETHANE COATINGS & ELASTOMERS; SOLVENT; DILUENT FOR EPOXY RESINS; SYNTHETIC FIBERS; IN ORG SYNTHESIS

U.S. Imports(1983) 4.30X10+8 g /4-Caprolactone/
U.S. Production2023: 10,000,000 - <25,000,000 lb
Industry UsesMonomers
Methods of ManufacturingREACTION PRODUCT OF PERACETIC ACID & CYCLOHEXANONE; AN INTERMEDIATE PRODUCT IN MFR OF CAPROLACTAM.
General Manufacturing Information · 2 Einträge

Paint and Coating Manufacturing

2-Oxepanone: ACTIVE

Anwendungen · 1 Eintrag

Verwendenε-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.

Vor- und nachgelagerte Produkte

Zugehörige Reaktionen

212
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 2257
HRID 2257als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2260
HRID 2260als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2261
HRID 2261als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2262
HRID 2262als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2263
HRID 2263als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2264
HRID 2264als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2265
HRID 2265als Eduktuspto-grants-1998_03
Reaktionsgleichung von HRID 2969
HRID 2969als Eduktuspto-grants-1998_03
Seite 1 von 27

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Weitere Aktionen
Neue NotizNeue ReaktionAnfrage stellen
· 4 Einträge

0.13 [mmHg]

1.35X10-1 mm Hg at 25 °C

Vapor pressure, Pa at 25 °C: 0.8

0.01 [mm Hg] @20 °C

Food Contact SubstancesFCS -> FDA Cumulative Estimated Daily Intake (CEDI)
Physical Description · 3 Einträge

CBI; Liquid

Colorless liquid; Miscible in water; [eChemPortal: SIDSUNEP] Colorless liquid; [MSDSonline]

COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR.

Physikochemische Eigenschaften

Schmelzpunkt
-1 °C · -1 °C
Siedepunkt
96 · 96-97.5 °C10 mm Hg(lit.)
Dichte
1.03 g/mL · 1.03 g/mL at 25 °C(lit.)
Dampfdichte
3.9 · 3.9 (vs air)
Dampfdruck
0.01 mm · 0.01 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.463(lit.)
Flammpunkt
229 °F · 229 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
Chloroform, Ethyl Acetate
Aggregatzustand
Liquid
Farbe
Clear colorless, yellowing on aging
Explosionsgrenze
1.2 · 1.2-9%(V)
Wasserlöslichkeit
1000 MG/L · >1000 MG/L (20 ºC)
BRN
106919 · 106919
Henry's Law Constant
5.5 · 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
0.32 at · 0.32 at 20℃
CAS Datenbank
502 · 502-44-3(CAS DataBase Reference)
NIST chemische Informationen
2 · 2-Oxepanone(502-44-3)
EPA chemische Informationen
2 · 2-Oxepanone (502-44-3)
Explosive Limits and PotentialExplosive limits , vol% in air: 1.2-9

Sicherheit und Schutzausrüstung

Fire FightingUse powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures · 4 Einträge

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.

Safe StorageSeparated from strong bases, strong acids and strong oxidants. Dry. Well closed.
Spillage DisposalPersonal 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 PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskEvaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation.
Effects of Short Term ExposureThe substance is irritating to the eyes.
Protective Action Criteria (PAC) · 3 Einträge

13 [mg/m3]

140 [mg/m3]

850 [mg/m3]

Toxikologische Informationen

Environmental Fate · 3 Einträge

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 radicals; the half-life for this reaction in air can be estimated to be about 2.76 days(2,SRC).

Signs and SymptomsRedness. Pain.
Effluent ConcentrationsCaprolactone was qualitatively identified in advanced waste water treatment concentrates from Pomona, CA(1-2).
Soil Adsorption/MobilityBased 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 · 1 Eintrag

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 levonorgestrel; patients 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 SourcesAs 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 · 1 Eintrag

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 · 1 Eintrag

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 · 2 Einträge

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 · 1 Eintrag

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 ExposureIn occupational settings, exposure to caprolactone may occur through inhalation of vapors and through eye and skin contact. (SRC)
Environmental Fate/Exposure Summary · 1 Eintrag

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)

Sicherheitsdaten

wgk
2
tsca
TSCA listed
hs_code
29322090
RTECS-Nr.
MO8400000
risk_code
37/38-41-36/38
Toxizität
LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg
hazard_code
Xi
safety_code
26-39-37/39
Speicherklasse
10 - Combustible liquids
Giftige Stoffe Daten
502-44-3(Hazardous Substances Data)
Hazard Classifications
Eye Irrit. 2
Selbstentzündungstemperatur
204 °C

Vorgelagerte Rohstoffe

Peroxyessigsäure ...%OzonCyclohexanonDicyclohexanone Diperoxide6-HYDROXYCAPROIC ACID

Nachgelagerte Produkte

(5-Carboxypentyl)(triphenyl)phosphonium bromidetert-Butyl 6-Hydroxyhexanoate6-ChlorhexanoylchloridMethyl-6-oxohexanoat8-fluoro-3-methyl-octanoic acid

Ergänzende Hinweise

DefinitionChEBI: A epsilon-lactone that is oxepane substituted by an oxo group at position 2.