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epsilon-CAPROLACTONE

HCID 10401
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
502-44-3
Standard SMILES
O=C1CCCCCO1
InChIKey
PAPBSGBWRJIAAV-UHFFFAOYSA-N
Molecular formula
C6H10O2
Average molar mass
114.14 g/mol
Monoisotopic mass
114.06807956

Overview

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

Names & identifiers

Preferred name
epsilon-CAPROLACTONE
IUPAC
oxepan-2-one
English name
ε-Caprolactone
Molecular formula
C6H10O2
Molecular weight
114.14

Names & synonyms

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

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP
0
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
8
Formal charge
0
Complexity
88.5

Experimental & physicochemical properties

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

log Kow= 1.215 (calc)

0.68

Density · 3 items

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 items

237 °C

215 °C @760 [mm Hg]

Melting Point · 2 items

-1.5 °C

-1 °C

Vapor DensityRelative vapor density (air = 1): 3.9
Vapor Pressure · 4 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

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.

Hazard information

Regulatory Information · 5 items

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 item

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%)

Chemistry & industry

Pharmacology

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.

Uses & manufacturing

Uses · 3 items

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 items

Paint and Coating Manufacturing

2-Oxepanone: ACTIVE

Applications · 4 items

UsesIntermediate in adhesives, urethane coatings, and elastomers; solvent; diluent for epoxy resins; synthetic fibers; organic synthesis.

Usesε-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.

Related reactions

212 records
New reaction record
HRID 2257 reaction equation
HRID 2257As reactantuspto-grants-1998_03
HRID 2260 reaction equation
HRID 2260As reactantuspto-grants-1998_03
HRID 2261 reaction equation
HRID 2261As reactantuspto-grants-1998_03
HRID 2262 reaction equation
HRID 2262As reactantuspto-grants-1998_03
HRID 2263 reaction equation
HRID 2263As reactantuspto-grants-1998_03
HRID 2264 reaction equation
HRID 2264As reactantuspto-grants-1998_03
HRID 2265 reaction equation
HRID 2265As reactantuspto-grants-1998_03
HRID 2969 reaction equation
HRID 2969As reactantuspto-grants-1998_03
Page 1 of 27

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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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 items

CBI; Liquid

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

COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR.

Physicochemical properties

Melting point
1 °C · −1 °C (30 °F; 272 K)
Boiling point
241 °C · 241 °C (466 °F; 514 K)
Density
1.03 g/cm3 · 1.030 g/cm3
vapor density
3.9 · 3.9 (vs air)
vapor pressure
0.01 mm · 0.01 mm Hg ( 20 °C)
refractive index
1.46 · 1.46
Flash point
115 °C · 115 °C
storage temp.
30 °C · Store below +30°C.
solubility
Chloroform, Ethyl Acetate
form
clear liquid
color
Colorless to Light yellow to Light orange
explosive limit
1.2 · 1.2-9%(V)
Water Solubility
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 DataBase Reference
502 · 502-44-3(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
56 RE988L1R · 56RE988L1R
NIST Chemistry Reference
2 · 2-Oxepanone(502-44-3)
EPA Substance Registry System
2 · 2-Oxepanone (502-44-3)
UNSPSC Code
12352115 · 12352115
NACRES
23 · NA.23
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319
Precautionary statements
264 · P264-P280-P305+P351+P338-P337+P313
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi
Risk Statements
37 · 37/38-41-36/38
Safety Statements
26 · 26-39-37/39
WGK Germany
2 · 2
RTECS
8400000 · MO8400000
Autoignition Temperature
204 °C · 204 °C
TSCA
TSCA listed
HS Code
2932209090 · 2932209090
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
2 · Eye Irrit. 2
Hazardous Substances Data
502 · 502-44-3(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg
REACH Registrations
Active
Explosive Limits and Potential
Explosive limits , vol% in air: 1.2-9

Safety & protection

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 items

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 items

13 [mg/m3]

140 [mg/m3]

850 [mg/m3]

Toxicology

Environmental Fate · 3 items

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 item

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 item

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 item

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 items

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 item

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 item

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)

Safety data

PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
MO8400000
hs_code
2932209090
Toxicity
LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg
risk_code
37/38-41-36/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-39-37/39
Storage Class
10 - Combustible liquids
Hazard statements
H319
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2
Autoignition Temperature
204 °C
Precautionary statements
P264-P280-P305+P351+P338-P337+P313
Hazardous Substances Data
502-44-3(Hazardous Substances Data)

Usesε-caprolactone is popularly used in the preparation of poly caprolactone (PCL).

General Descriptionε-caprolactone is a cyclic ester. Ring opening polymerization of ε-caprolactone initiated by, tributylin n butoxide, ethyl magnesium bromide, or samarium acetate or heteropolyacid, leads to the formation of poly caprolactone (PCL).

Upstream & downstream products

Upstream raw materials

Peroxyacetic acidOzoneCyclohexanoneDicyclohexanone Diperoxide6-Hydroxycaproic acid

Downstream products

(5-Carboxypentyl)(triphenyl)phosphonium bromidetert-Butyl 6-Hydroxyhexanoate6-Chlorohexanoyl chlorideAdipic semialdehyde methyl ester8-fluoro-3-methyl-octanoic acid

Additional notes

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