카프로락톤

epsilon-CAPROLACTONE

HCID 10401CAS 502-44-3

기본 정보

표준 SMILES
O=C1CCCCCO1
InChIKey
PAPBSGBWRJIAAV-UHFFFAOYSA-N
분자식
C6H10O2
평균 분자량
114.14 g/mol
단동위원소 질량
114.06807956

개요

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

이름 및 식별자

우선 이름
epsilon-CAPROLACTONE
IUPAC
oxepan-2-one
현지명
카프로락톤
영어명
ε-Caprolactone
분자식
C6H10O2
분자량
114.14

이름 및 동의어

Epsilon-caprolactoneCAPROLACTONE502-44-36-Hexanolactone2-Oxepanonehexano-6-lactone6-Hexanolide1,6-Hexanolide1-Oxa-2-oxocycloheptanePlaccel M6-Hydroxyhexanoic acid lactoneHexanoic acid, epsilon-lactone
이름 더 보기
카프로락톤카프롤락톤엡실론-카프롤락톤카프롤락톤2-옥세파논6-헥산올락톤6-하이드록시헥산오익산락톤1,6-헥산올리드6-하이드록시헥산오익 산 락톤헥산-6-오리드헥산오익 산, 엡실론-락톤oxepan-2-oneOxepanoneE-CAPROLACTONEPolycaprolactone Polyol6-CAPROLACTONE6-Hydroxyhexan-6-olide
Hexamethylene oxide, 2-oxo-epsilon-KaprolaktonDTXSID4027159epsilon caprolactoneCHEBI:17915TONE ECEQHexanoic acid, 6-hydroxy-, epsilon-lactone56RE988L1R

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
0
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
8

실험 및 물리화학적 성질

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

log Kow= 1.215 (calc)

0.68

Density · 3건

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.

물리화학적 성질

녹는점
-1 °C · -1 °C
끓는 점
96 · 96-97.5 °C10 mm Hg(lit.)
밀도
1.03 g/mL · 1.03 g/mL at 25 °C(lit.)
증기 밀도
3.9 · 3.9 (vs air)
증기압
0.01 mm · 0.01 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.463(lit.)

화학적 성질

Clear colorless liquid, yellowing on ageing

안전 및 규제

GHS 분류

GHS Classification · 5건

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.

유해성 정보

Regulatory Information · 5건

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Council Directive (EEC) No 109/1989 (Repealed by Reg.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 · 1건

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%)
Explosive Limits and PotentialExplosive limits , vol% in air: 1.2-9

안전 및 보호

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 · 4건

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.

독성 정보

Environmental Fate · 3건

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 · 1건

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).

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
MO8400000
독성
LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg
HS 번호
29322090
risk_code
37/38-41-36/38

화학 및 산업

약리 정보

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.

용도 및 제조

Uses · 3건

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 · 2건

Paint and Coating Manufacturing

2-Oxepanone: ACTIVE

응용 분야 · 2건

용도ε-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.

일반 설명ε-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).

추가 설명

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

관련 반응

212건

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