Cresyl glycidyl ether

164.2

164.08400

247-711-4

112255

DTXSID3024863

Clear, colorless Liquid

21.8

2.16 (est)

Cresyl glycidyl ether is a colorless liquid. Sinks and mixes with water. (USCG, 1999)

1.14 at 25 deg C

170 to 195 deg C at 100 mbar

200 Deg F (Open Cup)

1.533

In water, 930 mg/L at 25 deg C (est)

4.3X10-2 mm Hg at 25 deg C (est)

Henry's Law constant = 7.6X10-7 atm-cu m/mol at 25 °C (est)

Incompatible with strong oxidizing agents, strong acids, or bases|Hydroxyl radical reaction rate constant = 3.4X10-11 cu cm/molec-sec at 25 °C (est)

Oxidizes readily in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. Insoluble in water.

Ethers

Polymerizable

A phenol and epoxide. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Epoxides are highly reactive. They polymerize in the presence of catalysts or when heated. These polymerization reactions can be violent. Compounds in this group react with acids, bases, and oxidizing and reducing agents. They react, possibly violently with water in the presence of acid and other catalysts.

-16,500 Btu/lb = -9,190 cal/g = -384x10 5 J/kg

UN 3082 9/PG 3

3

61-36/38-43-51/53-62

53-26-36/37-45-61

Xn

Stable. Incompatible with strong acids, bases and oxidizing agents. May attack some types of plastic. Combustible.

P201, P202, P261, P264, P272, P273, P280, P281, P302+P352, P308+P313, P321, P332+P313, P333+P313, P362, P363, P391, P405, P501

H315

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.

/Cresyl glycidyl ether/ is incompatible with strong oxidizing agents, strong acids, or bases.

Special Hazards of Combustion Products: Wear full body and respiratory protection. (USCG, 1999)

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P261, P264, P272, P273, P280, P281, P302+P352, P308+P313, P321, P332+P313, P333+P313, P362, P363, P391, P405, and P501|Aggregated GHS information provided by 318 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P362, P363, and P501

SMALL SPILLS AND LEAKAGE: If you spill this chemical, 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 alcohol followed by washing with a strong 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 chemical under freezer conditions, and keep it away from all oxidizing materials, mineral acids and bases. (NTP, 1992)

Organic canister mask or air pack; rubber gloves; goggles or face shield; body covering clothing. (USCG, 1999)

Dry Chemical, foam, carbon dioxide.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Contact with skin and eyes causes irritation.|/Glycidyl ethers/ are primary skin and eye irritants and may cause sensitization. /Glycidyl ethers/|/Cresyl glycidyl ether and o-cresyl glycidyl ether/ are moderate to severe skin irritants and potent skin sensitizers ... slightly irritating to the eye.|Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl & diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl & diglycidyl ethers/

LD50 Rat oral 5140 mg/kg|LC50 Rat inhalation 1220 ppm/4 hr|LD50 Rat dermal >2150 mg/kg bw[European Chemicals Bureau; IUCLID Dataset,|LD50 Mouse subcutaneous 0.98 g/kg|For more Non-Human Toxicity Values (Complete) data for CRESYL GLYCIDYL ETHER (10 total), please visit the HSDB record page.

Cresyl glycidyl ether is not known to occur as a natural product(1).

Cresyl glycidyl ether's production and use as an ingredient in epoxy resins and a resin modifier(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 67(SRC), determined from a structure estimation method(2), indicates that cresyl glycidyl ether is expected to have high mobility in soil(SRC). Volatilization of cresyl glycidyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(4) through neutral, acid, or base-mediated reactions(5). Cresyl glycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-2 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2006).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 67(SRC), determined from a structure estimation method(2), indicates that cresyl glycidyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important environmental fate process(3) based upon an estimated Henry's Law constant of 7.6X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 9(SRC), from an estimated log Kow of 2.2(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Epoxides in general hydrolyze rapidly at 25 °C and pH 7(7) through neutral, acid, or base-mediated reactions(8). Hydrolysis products are usually the corresponding diol and sometimes re-arranged products(8). While data specific to cresyl glycidyl ether were not located(SRC, 2006), the hydrolysis half-life for an analogous compound glycidyl alcohol is 28 days at pH 7(7). Biodegradation data were not available(SRC, 2006). However, a 33% theoretical BOD using the Japanese MITI test for analogous phenyl glycidyl ether(9) suggests that biodegradation of cresyl glycidyl ether may occur in aquatic environments(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cresyl glycidyl ether, which has an estimated vapor pressure of 4.3X10-2 mm Hg at 25deg C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cresyl 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 11 hrs(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

The rate constant for the vapor-phase reaction of cresyl glycidyl ether with photochemically-produced hydroxyl radicals has been estimated as 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC), using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Glycidyl ethers, such as cresyl 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 cresyl glycidyl ether were not located(SRC, 2006), the hydrolysis half-life for an analogous compound glycidyl alcohol is 28 days at pH 7(3).

An estimated BCF of 9 was calculated for cresyl glycidyl ether(SRC), using an estimated log Kow of 2.2(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).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of cresyl glycidyl ether can be estimated to be 67(SRC). According to a classification scheme(2), this estimated Koc value suggests that cresyl glycidyl ether is expected to have high mobility in soil.

The Henry's Law constant for cresyl glycidyl ether is estimated as 7.6X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that cresyl glycidyl ether is not expected to volatilize from water surfaces(2). Cresyl glycidyl ether's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Cresyl glycidyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.3X10-2 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to cresyl glycidyl ether may occur through dermal contact with this compound at workplaces where cresyl glycidyl ether is produced or used. The general population may be exposed to cresyl glycidyl ether through dermal contact with epoxy resins and other products containing cresyl glycidyl ether. (SRC)

In vitro skin penetration studies with dermatomized human and rat skin and whole mouse skin indicated that o-cresyl glycidyl ether has a potential to penetrate the skin. Permeability was in the order: mouse>rat>human. o-Cresyl glycidyl ether is rapidly hydrolyzed after penetration into the skin; however, a minimum of 10% of the applied dose may be present as unchanged material after absorption through the skin. /o-Cresyl glycidyl ether/|Glycidyl ethers (GE), an important class of industrial chemicals, are considered to be potentially mutagenic in vivo because some GE have been shown to be direct mutagens in short-term in vitro tests. The percutaneous penetration and metabolism of representatives of different classes of GE was studied in the fresh, full-thickness C3H mouse, and dermatomed human and Fisher 344 rat skin to determine the apparent permeability constants, lag times and metabolic profiles. Five different GE, the diglycidyl ethers of bisphenol A (BADGE), 4,4'-dihydroxy-3,3',5,5'-tetramethylbiphenyl (Epikote YX4000) and 1,6-hexanediol (HDDGE) and the GE of 1-dodecanol (C12GE) and o-cresol (o-CGE), were synthesized by reaction of their alcohols with epichlorohydrin. Their radiolabelled analogues were synthesized with a 14C-label using [U-14C]-epichlorohydrin. There was a large variation (four orders of magnitude) in percutaneous penetration between the five GE. In general, penetration through full-thickness mouse skin was higher than through dermatomed rat skin, whereas dermatomed human skin was the least permeable. The permeability increased in the order YX4000 < BADGE < C12GE < o-CGE < HDDGE. The relative skin permeability of the five GE could be explained for a significant part by the lipophilicity, expressed as log P(o/w), in combination with the molecular weight of the compounds.

o-Cresyl glycidyl ether was converted rapidly to the corresponding diol compounds when incubated with guinea pig liver homogenate in vitro. /o-Cresyl glycidyl ether/|Studies in preparations of microsomal and cytosolic fractions of liver and lung derived from human, rat, and mouse showed that o-cresyl glycidyl ether is a good substrate for glutathione tranferase, with mice being the most efficient in enzymatic glutathione conjugation. Overall, enzymatic hydrolysis of the epoxide group is the most important route of in vitro biotransformation of o-cresyl glycidyl ether, with the highest activity located in the microsomes. Human samples generally had a higher efficiency for hydrolysis than mice or rats. /o-Cresyl glycidyl ether/|The urinary metabolite profile of o-cresyl glycidyl ether in rats, following ip administration of single doses up to 164 mg/kg, indicated that glutathione (GSH) conjugation and epoxide hydrolysis were key biotransformation pathways of o-cresyl glycidyl ether. At low dose levels GSH conjugation and epoxide hydrolysis accounted each for about 25% of urinary metabolites; however at higher doses epoxide hydrolysis became the most prominent route of detoxification (40%). /o-Cresyl glycidyl ether/|The urinary metabolite profiles of phenyl-glycidyl-ether (PGE) and its structural analogue ortho-cresyl-glycidyl-ether (oCGE) were determined in male Wistar-rats. Quantitative analytical methods were used to investigate the metabolites of PGE and oCGE, their dose excretion relationships and urinary excretion kinetics. Rats were dosed intraperitoneally with PGE or oCGE in doses ranging from 0.033 to 1.0 mmol/kg. ...Rats treated with oCGE excreted oCGEMA, COLA, and NAPS, showing that the metabolite profiles of PGE and oCGE were comparable. The quantitative methods developed to determine the urinary mercapturic-acid metabolites of PGE and oCGE offered enough selectivity and sensitivity for their determination as low as 0.033mmol/kg. The authors conclude the method can be used for humans with low potential exposures. Human excretion of lactic-acid and the novel serine metabolites of these glycidyl ethers should be further investigated, as possible inactivation of these epoxides may be by epoxide hydrolysis mediated routes.|... During skin penetration, all GE were extensively metabolized to their corresponding (bis-)diols. Virtually no YX4000, and only very small amounts of C12GE and BADGE, penetrated the skin unchanged, but significant amounts of HDDGE and o-CGE penetrated the skin unchanged. For o-CGE, but none of the other GE, the percentage of the applied dose that penetrated the skin unchanged increased over time. The large variation in response observed with the five selected GE indicates that GE should not be considered as a single class of compounds but rather on the basis of their individual properties.

Contact with eyes causes irritation. Contact with skin causes primary irritation and allergic sensitization. (USCG, 1999)

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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. (NTP, 1992)

Skin contact should be followed by thorough and repeated washing with soap and water. Do not use solvents to remove it. Eye contact requires flushing with water immediately and consultation with a physician.|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

/HUMAN EXPOSURE STUDIES/ Epoxy resin systems (ERSs) are a frequent cause of occupational allergic contact dermatitis. Sensitization occurs not only to the resins, but also to hardeners and reactive diluents. However, only a fraction of the ERS components currently in use are available for patch testing. With the multicentre study EPOX 2002, we attempted to improve diagnostics in this field by patch testing with components currently used in ERSs. During the first study period (October 2002 to July 2003), in addition to commercially available ERS patch test substances, 16 study substances (1 resin, 9 hardeners and 6 reactive diluents) were patch tested in 70 patients with suspected contact allergy due to ERSs and 22 patients with a prior positive patch test reaction to epoxy resin (ER) in the standard series. Most frequently, allergic reactions to ER based on diglycidyl ether of bisphenol A and F were observed (55.2% and 43.7%, respectively). Agreement between positive reactions to both resins, which can be explained by immunological cross-sensitization and/or coexposure, was substantial [Cohen's kappa 0.65 (95% CI: 0.49-0.80)]. Among the reactive diluents, 1,6-hexanediol diglycidyl ether (1,6-HDDGE) and 1,4-butanediol diglycidyl ether (1,4-BDDGE) were the most frequent allergens, with 19.5% and 18.4% positive reactions, respectively. Although agreement between positive reactions to 1,6-HDDGE and 1,4-BDDGE was even better than with the 2 resins, the sample size is considered too small to decide reliably whether 1,6-HDDGE alone could serve as a marker allergen for both. Allergic reactions to p-tert-butylphenyl glycidyl ether and to phenyl glycidyl ether (PGE) occurred in 11.5% of the patients tested, with only moderate agreement. All patients positive to cresyl glycidyl ether (6.8%) also reacted to PGE. Of the hardeners tested, m-xylylene diamine was the most frequent allergen (13.8%), followed by isophorone diamine (5.7%). No reactions were observed to several substances, the test concentration of which may have been too low and will be increased in the future.|/SIGNS AND SYMPTOMS/ Cresyl glycidyl ether is a mild irritant and may cause dermatitis.|/SIGNS AND SYMPTOMS/ Cresyl glycidyl ether and o-cresyl glycidyl ether are potent skin sensitizers in humans.|/CASE REPORTS/ A case of contact urticaria due to epoxy resin and reactive diluents was described. A 23 year old male with a 6 month history of pruritis and urticarial weals on the face and upper limbs, occasionally accompanied by angioderma of the lips and tongue, and transient laryngeal constriction was evaluated. He reported being employed for 2 years as a part fitter in an aircraft factory where he was regularly exposed to epoxy products and solvents such as naphtha (8030306) and 1,1,1-trichloroethane (71556). His symptoms would develop within 20 minutes of exposure to epoxy compounds and were worse when he was working within a closed section of fuselage. The symptoms resolved within about 2 hours after exposure ended. Patch testing was performed with the European standard allergen series and epoxy, acrylate, isocyanates, and plastics and glues series. The patient was also tested with a special series of 15 epoxy compounds, hardeners, and solvents which he used at work. The patches were read after 30 minutes and 4 days. Urticarial reactions were observed after 30 minutes to epoxy resin and the reactive diluents phenylglycidyl-ether (122601) and cresylglycidyl-ether (26447143). No delayed reactions were seen at the 4 day reading. The patient agreed to be retested with the three substances. Retesting produced similar urticarial lesions, which were also accompanied by pharyngeal tingling and hoarseness. Oral treatment with 10 milligrams loratadine (79794755) cleared the lesions within 60 minutes. The author notes that contact urticaria caused by epoxy compounds has been infrequently reported. However, this is the first reported case of contact urticaria being caused by reactive diluents.|For more Human Toxicity Excerpts (Complete) data for CRESYL GLYCIDYL ETHER (7 total), please visit the HSDB record page.

cresyl glycidyl ether

Trade names: Heloxy Modifier 62, Grilonit RV1805

Oxirane, 2-[(methylphenoxy)methyl]-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

The pyridinium chloride-chloroform method for epoxy groups and GLC are suggested, but the HCl-dioxane method for epoxides might also be used.