Diethylene glycol diethyl ether

log Kow = 0.39

0.39

0.39

0.9063 at 68 °F (NTP, 1992) - Less dense than water; will float

0.907 at 20 °C/4 °C

Relative density (water = 1): 0.91

0.9082 @ 20°C

greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)

Very soluble in ethanol, organic solvents; soluble in ethyl ether

Soluble in hydrocarbons

Infinite /1.0X10+6 mg/L/ solubility water at 25 °C

Solubility in water: very good

130 °F (NTP, 1992)

180 °F (82 °C) (Open Cup)

71 °C c.c.

372 °F at 760 mmHg (NTP, 1992)

188 °C

189 °C

189 °C @760 [mm Hg]

-47.7 °F (NTP, 1992)

-45 °C

-44 °C

-44 °C

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

Relative vapor density (air = 1): 5.6

0.54 mmHg at 77 °F (NTP, 1992)

0.52 [mmHg]

0.520 mm Hg at 25 °C

Vapor pressure, Pa at 20 °C: 79

0.52 [mm Hg] @25 °C

This chemical does not meet GHS hazard criteria for 5.6% (21 of 374) of reports.

Warning

H315 (42.8%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 374 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Chemical: Ethane, 1,1'-oxybis[2-ethoxy-

Ethane, 1,1'-oxybis[2-ethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,1'-oxybis[2-ethoxy- 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)

S - indicates a substance that is identified in a final Significant New Use Rule.

Status: Active Update: 11-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5924

Ethane, 1,1'-oxybis[2-ethoxy-: Does not have an individual approval but may be used under an appropriate group standard

This chemical is combustible. (NTP, 1992)

Combustible. Above 71 °C explosive vapour/air mixtures may be formed.

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and respiratory tract, coughing, dyspnea and kidney damage. Other symptoms may include nausea, vomiting, headache and central nervous system depression. Exposure may also cause diarrhea, abdominal and lumbar pain, mild liver damage, pulmonary edema, transient polyuria, oliguria, anuria and death by acute renal failure.

A mild skin and eye irritant; Defats the skin; [ICSC] A skin, eye, mucous membrane, and respiratory tract irritant; May cause kidney and liver damage and CNS depression; [CAMEO] May form explosive peroxides; An irritant; [MSDSonline] See Monoglyme.

Department of Health & Human Services/National Institute of Environmental Health Sciences, National Toxicology Program; Teratologic Evaluation Diethylene glycol diethyl ether (CAS No.112-36-7) Administered to CD-1 Mice on Gestational Days 6 through 15, NTP Study No. TER86059 (November 6, 1987) and Diethylene glycol diethyl ether (CAS No. 112-36-7) Administered to New Zealand White Rabbits on Gestational Days 6 through 19, NTP Study No. TER87060 (December 7, 1987). Available at http://ntp.niehs.nih.gov/index.cfm?objectid=0847FF31-90CC-C685-88B4D7EAC975BD44 as of August 15, 2002

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diethylene glycol diethyl ether is produced, as an intermediate or a final product, by process units covered under this subpart.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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.

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.

LC50; Species: Nitocra spinipes (Harpacticoid copepod, adults, length 0.6-0.8 mm); Conditions: static, 10 °C, pH 7.8, salinity 7 ppt, alkalinity 75 mg/L CaCO3, dissolved oxygen >5 mg/L; Concentration: 6600 mg/L for 96 hr (95% confidence interval: 6000-7300 mg/L) /98% pure/

LC50; Species: Alburnus alburnus (Bleak, length 8 cm); Conditions: static, 10 °C, pH 7.8, salinity 7 ppt, alkalinity 75 mg/L CaCO3, dissolved oxygen >5 mg/L; Concentration: 10,000 mg/L for 96 hr /98% pure/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 39(SRC), determined from a log Kow of 0.39(2) and a regression-derived equation(3), indicates that diethylene glycol diethyl ether is expected to have very high mobility in soil(SRC). Volatilization of diethylene glycol diethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-7 atm-cu m/mole(SRC), derived from Its vapor pressure, 0.52 mm Hg(4), and water solubility, 1X10+6 mg/L(5). Diethylene glycol diethyl ether may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation of diethylene glycol diethyl ether is not expected to be an important fate process in soil based on biodegradation studies conducted with sewage seed(6-7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 39(SRC), determined from a log Kow of 0.39(2) and a regression-derived equation(3), indicates that diethylene glycol diethyl 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 1.1X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.52 mm Hg(4), and water solubility, 1X10+6 mg/L(5). 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). Biodegradation of diethylene glycol diethyl ether is not expected to be an important fate process in water based on biodegradation studies conducted with sewage seed(8-9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol diethyl ether, which has a vapor pressure of 0.52 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol diethyl 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 14 hours(SRC), calculated from its rate constant of 2.7X10-11 cu cm/molecule-sec at 25 °C(3).

Redness. Dry skin.

Redness.

Diethylene glycol diethyl ether has been qualitatively identified in trench leachates from Maxey Flats and West Valley low-level radioactive waste disposal sites(1). Diethylene glycol diethyl ether has been qualitatively identified in advanced waste treatment water from Lake Tahoe, CA, Pomona, CA, and Blue Plains, Washington, DC(2). Diethylene glycol diethyl ether was tested from a light duty truck using different fuel types; diesel mixed with diethylene glycol diethyl ether: cold start 79 ug/cu m, hot start 52 ug/cu m; diesel fuel: cold start 23 ug/cu m, hot start 25 ug/cu m; diesel fuel mixed with diethylene glycol dimethyl ether: cold start 7.7 ug/cu m, hot start 7.3 ug/cu m; diesel fuel mixed with 2-ethylhexyl nitrate: not detected for cold and hot start(3).

The Koc of diethylene glycol diethyl ether is estimated as 39(SRC), using a log Kow of 0.39(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethylene glycol diethyl ether is expected to have very high mobility in soil.

An oral teratogenicity was conducted with 50 pregnant Charles River (CD-1) mice administered diethylene glycol diethyl ether (bis(2-ethoxyethyl) ether) by oral gavage at a dose level of 3000 mg/kg body weight on gestation days 7 to 14. The dose level chosen was the LD10 calculated from a previous range finding study. Mortality not was observed. Fetal toxicity was evident by statistical differences in number of dead pups per litter, and reduced pup birth weight (by analysis of variance). No significant changes were observed in number of pups per litter, percent pup postnatal survival, and pup weight gain over days 1-3 post partum. Of the pregnant mice, 95 percent of litters were viable. Gross necropsy observations were not reported.

Reproductive toxicity was evaluated in groups of 10 pregnant Charles River CD female mice receiving an oral gavage dose of ethylene glycol at 10 ml/kg body weight on gestation days 7 through 14. Maternal mortality, clinical observations and gross necropsy were not reported. There was a significant reduction (p<0.05) in the number of live pups per litter, reduced survival, and reduced birth weight among offspring of treated dams.

/SIGNS AND SYMPTOMS/ Symptomatology: B. Ethylene glycol and its mono- and diethers... 1. Central nervous depression... 3. Nausea, vomiting, and sometimes diarrhea. 4. ...Headache. Later abdominal and lumbar pain and costovertebral angle tenderness. 5. Transient polyuria and then oliguria, progressing to anuria. 6. Acute renal failure... 7. Less critical pathological lesions may appear in brain, lungs, liver, meninges and heart. /Ethylene glycol alkyl ethers/

/ALTERNATIVE and IN VITRO TESTS/ ...Skin permeation was calculated using the Franz cell method with human skin. A physiological solution was used as the receiving phase. ...A permeation profile was obtained and steady state, lag time and permeation constant flux was calculated for each of the following solvents: ethylene glycol monoethyl ether (EGMEE), propylene glycol mono-methyl ether (PGMME); propylene glycol mono-methyl ether acetate (PGMMEac); 2-propylene glycol 1-butyl ether (2PG1BE), ethylene glycol dimethyl ether (EGDME), ethylene glycol diethyl ether (EGDEE) and diethylene glycol dimethyl ether (DEGDME). All solvents were tested in their pure form and with 70% acetone. For all solvents tested the lag time was <2 hr, and for the majority of them was about 60 min. Flux at steady state ranged between 0.017 +/- 0.005 and 3.435 +/- 1.897 mg/sq cm/hr and permeation rate was from 0.0192 to 1.02 x 10-3 cm/hr. The presence of acetone in the solution caused a reduction in lag time and an increase in permeation rate, higher for EGMEE, lower for EGDEE, indicating the enhancing effect of this mixture of solvents. ...

/EPIDEMIOLOGY STUDIES/ Ethylene glycol ethers (EGEs) including diglyme are used in the manufacture of semiconductors. Epidemiological studies of semiconductor populations evaluated potential adverse reproductive outcomes. ... In each of these studies, workers were exposed to mixtures including diglyme but not to diglyme alone. ... Exposure to EGEs was determined using questionnaires from subjects about the work performed and an assessment of the work environment by industrial hygienists, but no measurements of personal or area exposures were made. Workers in the fabrication area were considered exposed to EGEs. For the retrospective study, information on pregnancy outcomes and potential confounders (age, smoking, ethnicity, education, income, year of pregnancy, and stress) was obtained through a comprehensive interviewer-administered interview of female employees. The prospective study of early fetal loss and fecundity (probability of conception per menstrual cycle) was conducted in a subset of female employees from five plants. Daily diaries and measurements of daily urinary human chorionic gonadotrophin (hCG) levels for 6 months were collected in addition to the comprehensive interview. Of the 891 medically verified pregnancies identified for the retrospective study, 774 (86.9%) were live births, 113 (12.7%) were spontaneous abortions, and 4 (0.4%) were stillbirths. The overall unadjusted relative risk (RR) for spontaneous abortions was 1.45 (95% confidence interval [CI] = 1.02-2.05) and changed little after adjusting for confounders (adjusted RR =1.43; 95% CI = 0.95-2.09). When stratified by work group, the risk of spontaneous abortion was statistically significantly increased for female workers in the photolithography group (RR = 1.67; 95% CI = 1.04-2.55) and in the etching group (RR = 2.08; 95% CI = 1.27-3.19). For women working with higher levels of EGE only in masking, the risk for spontaneous abortion was increased 3-fold (RR = 3.38; 95% CI = 1.61-5.73). In the prospective study, no statistically significant differences were detected in the overall rate of spontaneous abortions between fabrication and non-fabrication workers or when pregnancy outcomes were examined by work group. However, the ability to conceive was lower among female workers exposed to EGEs (fertility rate [FR] = 0.37; 95% CI = 0.11-1.19). /Ethylene glycol ethers/

Diethylene glycol diethyl ether's production and use as a high boiling reaction medium(1), and as a solvent for nitrocellulose, lacquers, resins, and organic syntheses(2) may result in its release to the environment through various waste streams(SRC).

AEROBIC: An aerobic biodegradation study using gram-negative asporogenous rod bacterium isolated from soil by enrichment on triethylene glycol exhibited borderline growth (scarcely detectable growth, not reproducible) with diethylene glycol diethyl ether(1). In a screening study using a sewage seed, diethylene glycol diethyl ether (concentration not specified) had a 10 day BOD of 0.10 g/g (4.2% theoretical BOD) at 20 °C(2). Diethylene glycol diethyl ether had a 21.7% COD removal at 30 °C from a starting concentration of 600 mg COD/L (time period not given) indicating little degradation compared to 95% degradation of ethylene glycol monophenyl ether(3).

An estimated BCF of 3 was calculated in fish for diethylene glycol diethyl ether(SRC), using a log Kow of 0.39(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 Henry's Law constant for diethylene glycol diethyl ether is estimated as 1.1X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 0.52 mm Hg(1), and water solubility, 1X10+6 mg/L(2). This Henry's Law constant indicates that diethylene glycol diethyl ether is expected to be essentially nonvolatile from water surfaces(3). Diethylene glycol diethyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may not occur(SRC). Diethylene glycol diethyl ether may volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diethylene glycol diethyl ether is produced, as an intermediate or a final product, by process units covered under this subpart.

Used as solvent for nitrocellulose, adhesives, sealants, plastic resins and compounds, rubber chemicals, lacquers, and organic synthesis; as high-boiling medium; [HSDB]

Painting (Solvents) [Category: Paint]

Solvent; high boiling reaction medium

Solvent for nitrocellulose, resins, lacquers; high-boiling medium and solvent for organic synthesis

SOLVENT FOR ADHESIVES, SEALANTS, PLASTIC RESINS & CMPDS, RUBBER CHEMS

/Glycol ethers/ are used as coupling agents for preparing miscible organic-aqueous systems

2023: 400,000 - <550,000 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(2006) 1,612 million lb annual capacity /Glycol ethers/

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#195]

REACTION OF ETHYLENE GLYCOL MONOETHYL ETHER WITH DIETHYL SULFATE

Glycol ethers are produced by reacting ethylene with alcohols in presence of either acid or base catalysts. Temperature, pressure, mole ratios of reactants and catalysts are chosen to yield the desired product

Ethylene glycol monoethers are usually produced by reaction of ethylene oxide with the appropriate alcohol. A mixture of homologues is obtained ... The glycol monoethers can be converted to diethers by alkylation with common alkylating agents, such as dimethyl sulfate or alkyl halides ( Williamson synthesis). Glycol dimethyl ethers are formed by treatment of dimethyl ether with ethylene oxide. /Ethers/

Computer and Electronic Product Manufacturing

Ethane, 1,1'-oxybis[2-ethoxy-: ACTIVE