ブチルグリシジルエーテル

log Kow = 0.63

0.63

0.91 (USCG, 1999) - Less dense than water; will float

0.908 g/cu cm at 25 °C

Relative density (water = 1): 0.91

0.91

0.918 @ 20°C

0.91

10 to 50 mg/mL at 72 °F (NTP, 1992)

In water, 20,000 mg/L at °C

Solubility in water, g/100ml at 20 °C: 2

2%

130 °F (NTP, 1992)

54 °C

54 °C (closed cup)

54 °C c.c.

130 °F

130 °F

327 °F at 760 mmHg (NTP, 1992)

164 °C

164 °C

327 °F

169 °C @760 [mm Hg]

327 °F

When heated to decomposition it emits acrid smoke and irritating fumes.

The substance decomposes on exposure to light and air.

3.78 at 25 °C (Air = 1)

Relative vapor density (air = 1): 3.78

3.2 mmHg at 77 °F (NTP, 1992)

3.2 [mmHg]

3.2 mm Hg at 25 °C

Vapor pressure, kPa at 25 °C: 0.43

3 mmHg at 77 °F

3.2 [mm Hg] @25 °C

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P318, P319, P321, P330, P333+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Chemical: Oxirane, (butoxymethyl)-

Hazard Traits - Carcinogenicity

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

Status: Active Update: 15-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/22306

Butyl glycidyl ether: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: May form explosive peroxides upon contact with air. Toxic fumes such as carbon monoxide may be produced.

Flammable. Above 54 °C explosive vapour/air mixtures may be formed.

Repeated or prolonged contact may cause skin sensitization. [ICSC] BGE causes testicular atrophy in male rats exposed to levels of 75 ppm or higher for 10 weeks. Potential for dermal sensitization; [ACGIH] Causes pulmonary edema in high dose animal studies; [Reference #1]

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, (butoxymethyl)- is included on this list.

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

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

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)

In case of fire: keep drums, etc., cool by spraying with water.

/Use/ water spray, foam, powder, carbon dioxide

If material on fire or involved in fire: Use water in flooding quantities. Use foam, dry chemical, or carbon dioxide. Apply water from as far a distance as possible. Cool all affected containers with flooding quantities of water. Solid streams of water may spread fire. Keep run-off water out of sewers and water sources.

Collect leaking and spilled liquid in sealable containers as far as possible. Wash away remainder with plenty of water.

Environmental considerations: Land Spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. Dike surface flow using soil. sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.

Environmental considerations: Water Spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction.

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors.

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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: particulate filter respirator adapted to the airborne concentration of the substance. 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.

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.

Where there is any possibility of a worker's eyes being exposed to BGE, 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 BGE, 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.

For more Preventive Measures (Complete) data for N-BUTYL GLYCIDYL ETHER (10 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 52(SRC), determined from a log Kow of 0.63(2) and a regression-derived equation(3), indicates that n-butyl glycidyl ether is expected to have high mobility in soil(SRC). Volatilization of n-butyl glycidyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 3.2 mm Hg(4), and water solubility of 2X10+4 mg/L(5). The potential for volatilization of n-butyl glycidyl ether from dry soil surfaces exists(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 52(SRC), determined from a log Kow of 0.63(2) and a regression derived equation(3), indicates that n-butyl glycidyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.5X10-5 atm-cu m/mole(SRC), derived from its vapor pressure of 3.2 mm Hg(4), and water solubility of 2X10+4 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 and 16 days, respectively (SRC). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). n-Butyl glycidyl ether contains an epoxide functional group which is susceptible to hydrolysis, but the rate of this reaction is very slow based upon an estimated half-life of over 60 years at pH 7(8). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyl glycidyl ether, which has a vapor pressure of 3.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyl 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 19 hours(SRC), calculated from its rate constant of 2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.

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

inhalation, ingestion, skin and/or eye contact

Cough. Sore throat.

Redness. Pain.

Redness. Pain.

irritation eyes, skin, nose; skin sensitization; narcosis; possible hematopoietic effects; central nervous system depression

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=2426-08-6]

The Koc of n-butyl glycidyl ether is estimated as 52(SRC), using a log Kow of 0.63(1) and a regression-derived equation(2). According to a classification scheme(2), this estimated Koc value suggests that n-butyl glycidyl ether is expected to have high mobility in soil(SRC).

Glycidyl n-butyl ether was evaluated for the ability to increase the incidence of micronuclei in bone marrow cells of female B6D2F1 mice treated by oral gavage. Ten mice received 1000 mg/kg of the test article (in corn oil) 1x daily for 5 days; animals were sacrificed 4 hours following the final dose. The percentage of cells with micronuclei was not statistically significantly (Dunnett's t-test, p > 0.1) increased compared to controls. The toxicity of glycidyl n-butyl ether to mice at the level tested was not reported.

In a modified dominant lethal and pathology study, mature male B6D2F1 mice were mated with 3 virgin females each. After pre-treatment matings, the males (2 groups/dose level, 20 and 10 males/group) were treated with glycidyl n-butyl ether by dermal application on clipped skin at dose levels of 0, 0.375, 0.75 or 1.5 g/kg/day, 3 times/week for 8 weeks. Two groups of unclipped male mice (10 and 20/group) served as controls. After the treatment period, males and females were mated for 3 weeks. Males were sacrificed following final mating period and females were sacrificed 14 days after the midweek of their mating periods. Variables were analyzed with respect to group differences by dose (dose), overall time period differences (time), and the dose group by time period interaction (dose/time). Significant differences were observed between treated and control animals in the following: decreased pregnancy rates (dose basis, excluding controls), increased implants/pregnant female (time basis, after 1st pre-treatment period with trend back to control value at (3rd post-treatment period), decreased proportion of dead implants (dose and dose/time bases), increased incidence of necrosis of the epidermis at point of application (high-dose group). No significant differences were observed between treated and control animals in the following: pregnancy rates, gross pathology of males, histopathology of the liver, lung, and testes, and numbers of dead cells and necrotic tubules.

The mutagenicity of glycidol n-butyl ether (GBE) was evaluated in Salmonella tester strains TA1535 and TA1538 (Ames Test), both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary bacterial toxicity determinations, GBE, diluted with DMSO, was tested for mutagenicity at concentrations up to 2000 ug/plate using the plate incorporation method. GBE caused a positive response in bacterial tester strain TA1535 at 2000 ug/plate, both with and without metabolic activation, and in bacterial tester strain TA1538 at concentrations of 100 ug/plate and higher without activation and at 500 ug/plate and higher with activation.

The mutagenicity of glycidol n-butyl ether (GBE) was evaluated in male B6D2F1 mice (at least 10) dermally exposed to GBE at a dose level of 1.5 g/kg three times/week for a minimum of 8 weeks. Following the treatment period, the male mice were mated with 3 untreated virgin female B6D2F1f mice for one week and mated with 3 fresh females for a second week. Significant differences were observed between pre- and post-treatment results in the following: proportion of deaths/pregnancy (increased during post-treatment period), number of implants/pregnancy (decreased post-treatment), and percent pregnancy (increased post-treatment).

For more TSCA Test Submissions (Complete) data for N-BUTYL GLYCIDYL ETHER (7 total), please visit the HSDB record page.

/SIGNS AND SYMPTOMS/ Appreciable skin irritation and sensitization have been reported in humans.

/SIGNS AND SYMPTOMS/ Dermal contact is the usual mode of exposure, but droplets in mist can also attack the eyes and respiratory tract. Glycidyl and diglycidyl ethers tend to be irritants and sensitizing agents. /Glycidyl and diglycidyl ethers/

/SIGNS AND SYMPTOMS/ Long-term (chronic): Exposure to BGE can cause inflammation and sensitization of the skin.

/SIGNS AND SYMPTOMS/ N-butyl glycidyl ether possesses satisfactory warning properties. Odor of vapors is not unpleasant but leads to irritation.

For more Human Toxicity Excerpts (Complete) data for N-BUTYL GLYCIDYL ETHER (8 total), please visit the HSDB record page.

n-Butyl glycidyl ether's production and use as a viscosity reducing agent, stabilizer for chlorinated solvents(1), reactive diluent for epxoy resins(2), and chemical intermediate (1) may result in its release to the environment through various waste streams(SRC).

1-Butyl glycidyl ether

Group 2B: Possibly carcinogenic to humans

Volume 125: (2020) Some Industrial Chemical Intermediates and Solvents

2020 online

2019

An estimated BCF of 3 was calculated for n-butyl glycidyl ether(SRC), using a log Kow of 0.63(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).

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, (butoxymethyl)- is included on this list.

BGE is rapidly absorbed and metabolized in both rats and rabbits. The major metabolite in urine was butoxyacetic acid; 23% of an oral (20 mg/kg) dose appeared in rat urine as 3-butoxy-2-acetylaminoproprionic acid. The latter metabolite was not detected in the rabbit.

The metabolism and urinary elimination of n-butyl-glycidyl-ether (2426086) were studied in male Wistar-rats and male New-Zealand-white-rabbits. Each of five rats received a single oral dose of corn-oil containing 20 milligrams per kilogram radiolabeled n-butyl-glycidyl-ether. Two rabbits received the equivalent dose in a gelatin capsule. Excretion was followed by scintillation counting over a period of 96 hours. Analytical methods applied to determine n-butyl-glycidyl-ether and metabolites in urine included thin layer chromatography, autoradiography, nuclear magnetic resonance spectroscopy, and mass spectrometry. Within 24 hours of administration, rats and rabbits excreted 87 percent and 78 percent of the n-butyl-glycidyl-ether dose, respectively. Further elimination was minimal. After 96 hours, total excretion was 92 percent for rats and 80 percent for rabbits. Major urinary metabolites in the rat were 3-butoxy-2-hydroxypropionic-acid, representing 9 percent of total metabolites, 3-butoxy-2-acetylaminopropionic-acid, representing 23 percent of total metabolites, and butoxyacetic-acid (2516930), representing 10 percent of total metabolites measured. In rabbits, the major metabolites included 3-butoxy-2-hydroxypropionic-acid, representing 35 percent of total metabolites, and butoxyacetic-acid, representing 5 percent of the metabolites measured. In both species, a major route of biotransformation was via the hydrolytic opening of the epoxide ring followed by oxidation of the resulting diol to 3-butoxy-2-hydroxypropionic-acid and subsequent oxidative decarboxylation to yield butoxyacetic-acid. The metabolite 3-butoxy-2-acetylaminopropionic-acid may have involved cleavage of the epoxide ring by ammonia (7664417) or an amine or may have occurred by animation of a keto acid. The authors note that these reactions represent efficient detoxication of n-butyl-glycidyl-ether.

Glycidyl ethers are used as reactive diluents in epoxy resins. [LaDou, p. 550]

Plastic Composites Manufacturing [Category: Industry]

Reactive diluent for epoxy resins

Viscosity reducing agent, acid acceptor for stabilizing chlorinated compounds, and chemical intermediate.

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1973) PROBABLY GREATER THAN 9.08X10+5 G

(1974) PROBABLY GREATER THAN 9.08X10+5 G

(1986) >1 million - 10 million pounds

For more U.S. Production (Complete) data for N-BUTYL GLYCIDYL ETHER (8 total), please visit the HSDB record page.