1,2-Epoxy-3-phenoxypropan

1.1092 at 68 °F (NTP, 1992) - Denser than water; will sink

1.1109 at 21 °C

Relative density (water = 1): 1.11

1.11

1.11

1 to 5 mg/mL at 64 °F (NTP, 1992)

12.9% in octane; completely sol in acetone and toluene

In water, 2,400 mg/L at 25 °C

Solubility in water, g/100ml at 20 °C: 0.24

0.2%

greater than 200 °F (NTP, 1992)

248 °F

248 °F (Closed Cup)

114 °C c.c.

248 °F

248 °F

473 °F at 760 mmHg (NTP, 1992)

245 °C

245 °C

473 °F

473 °F

Energy of decomposition (in range 360-450 °C) measured as 0.626 kJ/g.

When heated to decompostion it emits acid smoke and irritating fumes.

38.3 °F (NTP, 1992)

3.5 °C

3.5 °C

38 °F

38 °F

4.37 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

4.37 (Air = 1)

Relative vapor density (air = 1): 4.37

4.37

Danger

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P203, P261, P264, P271, P272, P273, P280, P302+P352, P304+P340, P317, P318, P319, P321, P332+P317, P333+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H312+H332 (15.6%): Harmful in contact with skin or if inhaled [Warning Acute toxicity, dermal; acute toxicity, inhalation]

P203, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Oxirane, (phenoxymethyl)-

Hazard Traits - Carcinogenicity

Oxirane, 2-(phenoxymethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Oxirane, 2-(phenoxymethyl)- 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)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 26-05-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13512

Phenyl glycidyl ether: HSNO Approval: HSR003051 Approved with controls

This chemical is probably combustible. (NTP, 1992)

Combustible.

PGE is a testicular toxin in male rats exposed by inhalation at 12 ppm for 19 days. [ACGIH] A skin irritant and sensitizer; [ICSC] Can cause narcosis, reproductive effects, and possible hematopoietic effects; [CAMEO] Animals have CNS depression and evidence of liver injury in high-dose studies. [HSDB]

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, (phenoxymethyl)- is included on this list.

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 10 ppm (60 mg/cu m).

Vacated 1989 OSHA PEL TWA 1 ppm (6 mg/cu m) is still enforced in some states.

PHENYL GLYCIDYL ETHER, an ether, can act as a base. They form salts with strong acids and addition complexes with Lewis acids. The complex between diethyl ether and boron trifluoride is an example. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.

Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinquisher. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Where there is any possibility of a worker's eyes being exposed to PGE, an eye-wash fountain should be provided within the immediate work area for emergency use.

Where there is any possibility of a worker's body being exposed to PGE, facilities for quick drenching of the body should be provided within the immediate work area for emergency use.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

For more Preventive Measures (Complete) data for PHENYL GLYCIDYL ETHER (6 total), please visit the HSDB record page.

LC50 Carassius auratus (Goldfish) 69 mg/L/24 hr; static

LC50 Carassius auratus (Goldfish) 43 mg/L/96 hr; static

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a water solubility of 2,400 mg/L(2) and a regression-derived equation(3), indicates that phenyl glycidyl ether is expected to have high mobility in soil(SRC). Volatilization of phenyl glycidyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.0X10-2 mm Hg(2), and water solubility(2). Phenyl glycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). A theoretical BOD range from 0 to 6% after 5 days using activated sludge(4,5) indicates that biodegradation may not be an important fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a water solubility of 2,400 mg/L(2) and a regression-derived equation(3), indicates that phenyl glycidyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.0X10-2 mm Hg(2), and water solubility(2). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(4) through neutral, acid, or base-mediated reactions(5). Hydrolysis products are usually the corresponding diol and sometimes re-arranged products(5). According to a classification scheme(6), an estimated BCF of 8(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A theoretical BOD range from 0 to 6% after 5 days using activated sludge(7,8) indicates that biodegradation may not be an important fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenyl glycidyl ether, which has a vapor pressure of 1.0X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase phenyl glycidyl ether is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 13 hrs(SRC), calculated from its rate constant of 2.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Phenyl glycidyl ether does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

The substance can be absorbed into the body by inhalation of its aerosol and through the skin.

inhalation, skin absorption, ingestion, skin and/or eye contact

Cough. Sore throat.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain.

irritation eyes, skin; upper respiratory system; skin sensitization; narcosis; possible hematopoietic, reproductive effects; [potential occupational carcinogen]

A medical surveillance program should include systematic collection and epidemiologic analysis of relevant environmental and biologic monitoring, medical screening, morbidity, and mortality data. This analysis may provide information about the relatedness of adverse health effects and occupational exposure that cannot be discerned from results in individual workers. Sensitivity, specificity, and predictive values of biologic monitoring and medical screening tests should be evaluated on an industry-wide basis prior to application in any given worker group.

The Koc of phenyl glycidyl ether is estimated as 60(SRC), using a water solubility of 2,400 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that phenyl glycidyl ether is expected to have high mobility in soil.

Chronic toxicity and oncogenicity were evaluated in groups of male and female Chr:CD rats (100/sex/group) receiving whole body exposure to phenyl glycidyl ether vapor at a nominal concentration of 0, 1.0 or 12ppm, six hours a day, five days a week for two years beginning at age 5 to 6 weeks. Survival among the high dose males was significantly lower than for the controls and exhibited a dose response relationship. Survival among low dose females was significantly lower than for controls with no dose-relationship exhibited. The frequency of neoplastic/non-neoplastic lesions contributing to the cause of death of both treated and controls was not statistically significant. Body weights of the high dose males were significantly greater than the controls, but due to the lack of food consumption data, it's biological significance is unclear. Total leukocyte counts tended to be slightly higher among high exposure male rats compared to controls. The 24 month sacrifice revealed a significantly greater incidence of nasal tumors (1 classified as adenoid epidermoid carcinoma and 12 various differentiated epidermoid carcinomas) in high dose male and female rats. After 24 months on study, high dose male and female rats exhibited a significantly greater frequency of rhinitis and squamous metaplasia or dysplasia of the respiratory epithelium and subepithelial gland in the anterior nasal cavity.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Oxirane, (phenoxymethyl)- is included on this list.

2,3-Epoxypropyl phenyl ether metabolized in rat and ferret to 3-(S-glutathionyl)-2-hydroxypropyl phenyl ether. /from table/

Rabbits and rats dosed with 1,2-epoxy-3-phenoxypropane excrete 2-hydroxy-3-phenoxypropionic acid and N-acetyl-S-2-hydroxy-3-phenoxypropyl)-L-cysteine. The administration produces a marked fall in hepatic glutathione level.

In vitro metabolic conjugation is catalyzed by glutathione-S-alkyltransferase.

Studies with PGE in rats and rabbits have shown evidence for two key mechanisms in the metabolism of PGE: hydrolysis of the epoxide group and glutathione conjugation. In rats, the capacity for glutathione (GSH) conjugation is limited and the ratio of GSH conjugation and hydrolysis decreases with increasing exposure to PGE. Urinary metabolites identified for rat following subcutaneous administration of PGE were 3-phenyloxylacetic acid (up to 94% of the administered dose) and small quantities of the mercapturic acid of phenyl glycidyl ether (N-acetyl-S-(2-hydroxy-3-phenoxypropyl)-L-cysteine) ... A novel metabolite (N-acetyl-O-phenylserine) derived from transamination from the epoxide hydrolysis pathway was described.

The urinary excretion of metabolites of phenyl glycidyl ether (PGE) and o-cresyl glycidyl ether (o-CGE) was investigated in rats. Urine was collected, in fractions, from rats intraperitoneally administered PGE or o-CGE in doses ranging from 0.033 to 1.0 mmol/kg. The metabolites were extracted from acidified urine with ethyl acetate or diethyl ether, and their identity was elucidated by GC/MS analysis. The epoxide of PGE can be inactivated by glutathione (GSH) conjugation or epoxide hydrolysis. After further metabolism, these routes lead to the urinary excretion of phenyl glycidyl ether mercapturic acid (PGEMA) and 3-(phenyloxy)lactic acid (POLA). The excretion of PGEMA and POLA was described before and is confirmed in this study. Additionally, a new metabolite was identified as N-acetyl-O-phenylserine (NAPS), which is proposed to be formed from POLA by subsequent oxidation, transamination, and N-acetylation. For PGEMA a linear dose-excretion relationship was found (r2 = 0.988), and the percentage of the dose excreted declined from 27% to 10% with increasing PGE dose. For NAPS also a linear dose-excretion relationship was found (r2 = 0.985), and NAPS accounted for 27% of the PGE dose. The excretion of PGEMA and NAPS was rather fast: 93% and 75%, respectively, of the respective total cumulative amounts excreted was already collected within 6 hr after administration.

Phenyl glycidyl ether percutaneous absorption rates were 13.5 mg/sq cm/hr in rats & 4.2 mg/sq cm/hr for rabbits.

Acute dermal treatment of rats and rabbits with PGE showed that the substance is well absorbed through the skin... .

Glycidyl ethers are used as reactive diluents in epoxy resins. [LaDou, p. 550] Allergic contact dermatitis in shoemakers; [Marks] As a reactive diluent in uncured epoxy resins, it reduces viscosity in casting , adhesive and laminating applications; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

As an acid acceptor it is very effective as a stabilizer of halogenated compounds. Its high solvency for halogenated materials offers many possibilities as an intermediate.

Plasticizer for epoxy resins

Monomer for photoreactive polymers /from table/

PGE is used as a reactive diluent in uncured epoxy resins to reduce the viscosity of the uncured system for ease in casting, adhesives and laminating applications.

2023: <25,000 lb

(1986) 10 thousand-500 thousand pounds

(1990) 10 thousand-500 thousand pounds

(1998) 10 thousand-500 thousand pounds

(2002) 10 thousand-500 thousand pounds

Custom Compounding of Purchased Resins

Oxirane, 2-(phenoxymethyl)-: ACTIVE

The epoxy group of the glycidylethers reacts during the curing process, so glycidylethers are generally no longer present in completely cured products.