Phenyl glycidyl ether

150.174

150.17

204-557-2

0188

53476|635

2810

DTXSID8021145|DTXSID2094134

Colorless liquid (Note: A solid below 38 degrees F)

2910900090

21.76000

1.74

Phenyl glycidyl ether is a colorless liquid. (NTP, 1992)

1.1092 g/cm³

3.5 °C

245 °C @ Press: 760 Torr

94.8±19.4 °C

1.537

1 to 5 mg/mL at 64° F (NTP, 1992)

Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

0.01 mm Hg at 68 °F (NTP, 1992)

5.2 (vs air)

Henry's Law constant = 8.2X10-7 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.9X10-11 cu cm/molec-sec at 25 °C (est)

Ethers tend to form unstable peroxides when exposed to oxygen. Ethyl, isobutyl, ethyl tert-butyl, and ethyl tert-pentyl ether are particularly hazardous in this respect. Ether peroxides can sometimes be observed as clear crystals deposited on containers or along the surface of the liquid. Slightly soluble in water.

Ethers

Peroxidizable Compound

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.

1,2-Epoxy-3-phenoxypropane|D: Other compounds that may form peroxides|Kelly

Combustible|Class IIIB Combustible Liquid: Fl.P. at or above 200°F.

NONH for all modes of transport

3

R20;R37/38;R43;R45;R52/53;R68

S53-S45-S61

TZ3675000

T:Toxic;

Stable. Incompatible with strong oxidizing agents.

P201-P261-P273-P280-P305 + P351 + P338-P308 + P313

H312 + H332-H315-H317-H318-H335-H341-H350-H412

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.

Incompatibilities: Contact with strong oxidizing agents may cause fires and explosions. Contact with amines, strong acids, and strong bases may cause polymerization with the liberation of heat and spattering. Exposure to light and air may result in the formation of explosive peroxides.|Strong oxidizers, amines, strong acids, strong bases.

This chemical is probably combustible. (NTP, 1992)|Combustible.

|Danger|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P308+P313, P312, P321, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|Aggregated GHS information provided by 592 companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]|P201, P202, P261, P264, P271, P272, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P332+P313, P333+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P322, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wherever feasible ... enclosure of the operation and/or the application of local exhaust ventilation. ... respirators may be necessary to prevent pulmonary irritation and sensitization in exposed workers. Preferred respirators include gas masks with organic vapour cannisters and high-efficiency particulate filters or supplied-air respirators. All body surfaces should be protected against contact ... through the use of gloves, aprons, face shields, goggles and other protective equipment and clothing as necessary. Contaminated clothing should be removed as soon as possible and the affected areas of the skin washed with soap and water. /Epoxy compounds/|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|For more Personal Protective Equipment (PPE) (Complete) data for PHENYL GLYCIDYL ETHER (7 total), please visit the HSDB record page.|(See protection codes)

The substance can presumably form explosive peroxides.

Dry chemical, carbon dioxide, or alcohol foam.

Do NOT let this chemical enter the environment. Collect leaking liquid in covered containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place.

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.

Irritant to eyes and skin.|/Glycidyl ethers/ are primary skin and eye irritants. ... /Glycidyl ethers/|PGE is ... a skin sensitizer /and/ ... is irritant to the respiratory tract upon single or repeated inhalation exposure.

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.

NIOSH considers phenyl glycidyl ether to be a potential occupational carcinogen.|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration.|Recommended Exposure Limit: 15 Min Ceiling Value: 1 ppm (6 mg/cu m).

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.

Store in an area without drain or sewer access. Separated from strong oxidants, strong bases, strong acids and amines. Cool. Keep in the dark.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is irritating to the eyes, skin and respiratory tract.

Repeated or prolonged contact may cause skin sensitization. This substance is possibly carcinogenic to humans.

NO open flames.

See EFFECTS OF LONG-TERM OR REPEATED EXPOSURE. AVOID ALL CONTACT!

Use ventilation, local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection.

Phenyl glycidyl ether was qualitatively detected in water samples collected from an advanced waste treatment facility in Lake Tahoe, CA on Oct 24, 1974)(1).

LD50 Mouse oral 1400 mg/kg|LD50 Rat oral 2.5 g/kg|LD50 Rabbit dermal 1500 mg/kg|LD50 Mouse sc 760 mg/kg|For more Non-Human Toxicity Values (Complete) data for PHENYL GLYCIDYL ETHER (6 total), please visit the HSDB record page.

Phenyl glycidyl ethers are not known to occur as natural products(1).

Phenyl glycidyl ether's production and use as a component in epoxy resins(1) may result in its release to the environment through various waste streams(SRC).

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 rate constant for the vapor-phase reaction of phenyl glycidyl ether with photochemically-produced hydroxyl radicals has been estimated as 2.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Glycidyl ethers, such as phenyl glycidyl ether, can react readily with water and with nucleophiles such as proteins and nucleic acids(2). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(3) through neutral, acid, or base-mediated reactions(4). Hydrolysis products are usually the corresponding diol and sometimes re-arranged products(4). While data specific to phenyl glycidyl ether were not located(SRC, 2006), the hydrolysis half-life for an analogous compound glycidyl alcohol is 28 days at pH 7(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(1).

An estimated BCF of 8 was calculated for phenyl glycidyl ether(SRC), using a water solubility of 2,400 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

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.

The Henry's Law constant for phenyl glycidyl ether is estimated as 8.2X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 1.0X10-2 mm Hg(1), and water solubility, 2,400 mg/L(1). This Henry's Law constant indicates that phenyl glycidyl ether is expected to be essentially nonvolatile from water surfaces(2). Phenyl glycidyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). The potential for volatilization of phenyl glycidyl ether from dry soil surfaces may(SRC) based upon its vapor pressure(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,551 workers (4,108 of these are female) are potentially exposed to phenyl glycidyl ether in the US(1). Occupational exposure to phenyl glycidyl ether may occur through dermal contact with this compound at workplaces where phenyl glycidyl ether is produced or used. The general population exposure to phenyl glycidyl ether may be limited to dermal contact for those using products containing this compound(2).|Total workers exposed all industries: 356 in small industries (1-99 employees); 6,127 in medium industries (100-499 employees); 4,068 in large industries (500+ employees)

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... .

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.

Exposure Routes: inhalation, skin absorption, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin; upper respiratory system; skin sensitization; narcosis; possible hematopoietic, reproductive effects; [potential occupational carcinogen] Target Organs: Eyes, skin, central nervous system, hematopoietic system, reproductive system (NIOSH, 2016)|Carcinogens

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)|(See procedures)

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.

/HUMAN EXPOSURE STUDIES/ Contact allergy to PGE has been observed in workers handling epoxy resin systems, glues, and plastics. There is some evidence suggesting that cross-sensitization with other glycidyloxy compounds may also occur. No adverse systemic effects have been described ...|/SIGNS AND SYMPTOMS/ Short-term (acute): Exposure to PGE can cause irritation of the eyes, nose, respiratory tract, and skin. Long-term (chronic): Exposure to PGE can cause defatting and drying of the skin, dermatitis, blisters, edema, rash, exzema, and skin sensitization; cross sensitization with other glycidyl ethers can also occur.|/SIGNS AND SYMPTOMS/ Twenty workers in an Italian aircraft factory suffered from an outbreak of contact dermatitis; symptoms ranged from slight erythema to strong edematous-vesicular lesions on the upper extremities and face but rarely on the genitalia and thighs. Patch testing was positive to the epoxy-resin material in 13/20 workers. Thin-layer chromatography identified tetra-glycidyl 4,4-dimethyl dianiline and PGE as the haptens responsible for this outbreak of contact dermatitis.|/CASE REPORTS/ Skin sensitivity studied in 40 workers with dermatitis, and occupationally exposed to epoxy resins, but not to phenylglycidyl ether. Five showed positive skin sensitivity reactions to phenylglycidyl ether. Among 58 dermatitis patients who had been exposed occupationally to phenylglycidyl ether, 9 primarily responded to phenylglycidyl ether.|For more Human Toxicity Excerpts (Complete) data for PHENYL GLYCIDYL ETHER (6 total), please visit the HSDB record page.

phenyl glycidyl ether

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

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

Cough. Sore throat.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain.

Eyes, skin, central nervous system, hematopoietic system, reproductive system

Paint and coating manufacturing|Oxirane, 2-(phenoxymethyl)-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.|Oxirane, 2-(phenoxymethyl)-, homopolymer: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|The epoxy group of the glycidylethers reacts during the curing process, so glycidylethers are generally no longer present in completely cured products.

NIOSH Method S74. Analyte: Matrix: Air. Procedure: Gas chromatography/Flame ionization detector. Method Evaluation: Method was validated over the range of 31 to 121 mg/cu m using a 50 liter sample. Precision (CVt): 0.057. Applicability: Under the conditions of sample size (50 liter) the useful range is 6 to 180 mg/cu m.|Solid sorbent sampling and chromatographic determination of glycidyl ethers in air.|Method: NIOSH 1619, Issue 1; Procedure: gas chromatography with flame ionization detector; Analyte: phenyl glycidyl ether; Matrix: air; Detection Limit: not provided.

Health Hazards -> Carcinogens