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Home > Encyclopedia > ε-Caprolactone

ε-Caprolactone

ε-Caprolactone structure

ε-Caprolactone 

structure
  • CAS No:

    502-44-3

  • Formula:

    C6H10O2

  • Chemical Name:

    ε-Caprolactone

  • Synonyms:

    2-Oxepanone;Hexanoic acid,6-hydroxy-,lactone;Caprolactone;ε-Caprolactone;Epsilon-caprolactone;Hexanoic acid,6-hydroxy-,ε-lactone;Hexamethylene oxide,2-oxo-;6-Hexanolactone;6-Hydroxyhexanoic acid lactone;1,6-Hexanolide;Placcel M;Caprolactone A;2-Oxooxopane;6-Hexanolide;ε-Hexanolactone;Tone Monomer EC;Tone ECEQ;Nyrim 1 Additive 6;C 0702;52004-64-5;67184-99-0;80137-66-2

  • Categories:

    Pharmaceutical Intermediates  >  Analgesics

Description

Clear colorless liquid, yellowing on ageing


Liquid|COLOURLESS HYGROSCOPIC LIQUID WITH CHARACTERISTIC ODOUR.


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

ε-Caprolactone Basic Attributes

114.14200

114.14

207-938-1

56RE988L1R

1741

DTXSID4027159

2932209090

Characteristics

26.30000

0

Liquid

1.029 g/cm3 @ Temp: 26 °C

-18 °C

215 °C

109ºC

1.462-1.464

H2O: >1000 MG/L (20 ºC)

0.01 mm Hg ( 20 °C)

3.9 (vs air)

LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit 5990 mg/kg

vol% in air: 1.2

Henry's Law constant= 1.809X10-4 atm-cu m/mole at 25 °C (est)

204 °C

Safety Information

NONH for all modes of transport

2

R36/38

S26-S37/39

MO8400000

Xi

Separated from strong bases, strong acids and strong oxidants. Dry. Well closed.

P280-P305 + P351 + P338-P337 + P313

H319

Combustible.

|Warning|H319 (91.19%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 775 companies from 6 notifications to the ECHA C&L Inventory.|H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P280, P302+P352, P312, P322, P363, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Use powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Explosive limits , vol% in air: 1.2-9

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.

Separated from strong bases, strong acids and strong oxidants. Dry. Well closed.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying.

The substance is irritating to the eyes.

NO open flames.

Use ventilation.

Protective gloves.

Wear safety goggles.

Caprolactone was qualitatively identified in advanced waste water treatment concentrates from Pomona, CA(1-2).

Toxicity

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).

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).

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).

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).

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).

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).

In occupational settings, exposure to caprolactone may occur through inhalation of vapors and through eye and skin contact. (SRC)

Drug Information

The incorporation of estramustine into biodegradable waxy type copolyesters, prepared by direct copolycondensation of epsilon-caprolactone and delta-valerolactone in the absence of catalysts, to apply as implantable matrices for drug delivery systems, is described and the in vivo capability of the implantable device was evaluated by implanting into the back of male rats. The copolyesters are much more subject to erosion than their homopolyesters, in which the degradation is further accelerated by the action of lipase type enzyme. The drug release, although accompanying a burst phenomenon in the initial stage, was kept constant throughout an experimental period of 19 wk from the first to twentieth wk. In this case, the release pattern was parallel to the degradation pattern, in support of the release being the rate-limiting step in the degradation of the polymer. The results showed about 75% of the initial drug content was still present in the device even after 20 wk of implantation. This finding means that the biodegradable poly(epsilon-caprolactone-co-delta-valerolactone) wax is useful as an implantable matrix for a drug delivery system which controls the release over a relatively long period of time. The in vivo activity of the drug was demonstrated by observing atrophy of the seminal vesicles and ventral prostate in male rats 10 wk after implantation.|The release of levonorgestrel from a poly(epsilon-caprolactone) capsule implanted subdermally in 8 women was studied over 5 menstrual cycles. All subjects except one experienced suppression of ovulation while the capsule was in place (one cycle). The capsules contained 16 mg of drug and 61 mg of ethyl oleate as a suspending vehicle. There was a wide range of serum levels of the drug. Suppression of ovulation appeared to occur at a serum level of 300 pg/ml or greater.

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

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.

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.

caprolactone

Redness. Pain.

ε-Caprolactone Use and Manufacturing

Methods of Manufacturing

REACTION PRODUCT OF PERACETIC ACID & CYCLOHEXANONE; AN INTERMEDIATE PRODUCT IN MFR OF CAPROLACTAM.

Uses

Ε-Caprolactone or simply caprolactone is a cyclic ester, a member of the lactone family, with a seven-membered ring with the formula (CH2)5CO2. This colorless liquid is miscible with most organic solvents. It is produced on a large scale as a precursor to polycaprolactones.


Adhesives and sealant chemicals


Paints and coatings

Production

10,000,000 - 50,000,000 lb

Adhesive manufacturing|2-Oxepanone: ACTIVE|2-Oxepanone, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).

Cosmetics -> Stabilizing

Computed Properties

Molecular Weight:114.14
Hydrogen Bond Acceptor Count:2
Exact Mass:114.068079557
Monoisotopic Mass:114.068079557
Topological Polar Surface Area:26.3
Heavy Atom Count:8
Complexity:88.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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