Glycol ethers are federal hazardous air pollutants and were identified as toxic air contaminants in April 1993 under AB 2728.
CAS Registry Numbers: See Table I
Molecular Formulas: See Table I
Glycol ethers, as defined in the federal Clean Air Act Section 112(b) and listed as “Must Be Quantified for Emissions Inventory” for the Air Toxics “Hot Spots” Program (AB 2588), are diethylene glycol dimethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, ethylene glycol diethyl ether, ethylene glycol dimethyl ether, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol monopropyl ether, and triethylene glycol dimethyl ether (CAPCOA, 1993). Currently, the inclusion of propylene glycol ethers in the definition of glycol ethers is being debated within the United States Environmental Protection Agency (U.S. EPA), but no decisions have been made.
The physical properties and characteristics of glycol ethers are described in Tables I and II (Howard, 1990; Merck, 1989; Sax, 1989; U.S. EPA, 1994a).
Glycol ethers are mainly used as solvents (HSDB, 1993). The primary stationary sources that have reported emissions of glycol ethers in California are described in Table III (ARB, 1997b).
Ethylene glycol monobutyl ether (2-butoxyethanol) is registered as an adjuvant for agricultural products; it is used to facilitate the application of other agricultural products. The licensing and regulation of pesticides for sale and use in California are the responsibility of the Department of Pesticide Regulation (DPR). Information presented in this fact sheet regarding the permitted pesticidal uses of ethylene glycol monobutyl ether has been collected from pesticide labels registered for use in California and from DPR's pesticide databases. This information reflects pesticide use and permitted uses in California as of October 15, 1996. For further information regarding the pesticidal uses of this compound, please contact the Pesticide Registration Branch of DPR (DPR, 1996).
The total emissions of glycol ethers from stationary sources in California are estimated to be at least 4.2 million pounds per year, based on data reported under the Air Toxics "Hot Spots" Program (AB 2588). Emissions for some individual glycol ethers are listed in Table III. Of the 4.2 million pounds per year total emissions reported, 2.9 million pounds per year emissions were not specified individually, and were reported under the general group, glycol ethers. This was based on data reported under the Air Toxics "Hot Spots" Program (ARB, 1997b).
No information about the natural occurrence of the glycol ethers was found in the readily-available literature.
No Air Resources Board data exist for ambient measurements of glycol ethers.
Potential sources of glycol ethers in indoor air include paints and other coatings, inks, adhesives, nail polishes, cosmetics, household cleaning products, and other consumer products (Hodgson and Wooley, 1991). Indoor data on glycol ethers is very limited. Sheldon et al. (1988b) measured ethyoxyethyl acetate (ethylene glycol monoethyl ether acetate) levels in six public buildings located in the eastern United States. Ethyoxyethyl acetate was present in measurable levels in four of the buildings at concentrations ranging from 1.31 to 9.58 micrograms per cubic meter. Corresponding outdoor levels were below the limits of detection.
Glycol ethers exist in the atmosphere in the gas phase. The dominant atmospheric loss process for the glycol ethers is by reaction with the hydroxyl radical. Based on this reaction, the atmospheric half-life and lifetime of 2-butoxyethanol, 2-ethoxyethanol, 1-acetoxy- 2-ethoxyethane, and 2-methoxyethanol are in the ranges of 0.6 to 0.9 days and 0.8 to 1.3 days, respectively (Atkinson, 1989, 1994). Its reaction products include hydroxyesters, hydroxyacids, hydroxycarbonyls, peroxyacyl nitrates, and formaldehyde (Kao, 1994).
The Office of Environmental Health Hazard Assessment reviews risk assessments submitted under the Air Toxics "Hot Spots" Program (AB 2588). Of the risk assessments reviewed as of December 1996, for non-cancer health effects, glycol ethers contributed to the total hazard index in 31 of the approximately 89 risk assessments reporting a total chronic hazard index greater than 1, and presented an individual hazard index greater than 1 in 4 of these risk assessments. Glycol ethers also contributed to the total hazard index in 18 of the approximately 107 risk assessments reporting a total acute hazard index greater than 1, and presented an individual hazard index greater than 1 in 9 of these risk assessments (OEHHA, 1996b).
This section discusses the glycol ethers for which there is the most toxicological information.
Possible routes of human exposure to glycol ethers are inhalation, ingestion, and dermal contact.
Non-Cancer: Acute exposure to high levels of the glycol ethers in humans results in narcosis, pulmonary edema, and severe liver and kidney damage. Acute exposure to lower levels of glycol ethers in humans causes conjunctivitis, temporary corneal clouding, and upper respiratory tract irritation. Chronic exposure to the glycol ethers in humans results in fatigue, lethargy, nausea, anorexia, tremor, and anemia (U.S. EPA, 1994a). Some studies have shown that propylene glycol ethers may be safer replacements for ethylene glycol ethers (ARCO, 1996).
Acute and chronic non-cancer Reference Exposure Levels (REL) for the following glycol ethers are listed in the California Air Pollution Control Officers Association Air Toxics "Hot Spots" Program, Revised 1992 Risk Assessment Guidelines. The toxicological endpoints considered are also indicated (CAPCOA, 1993).
| Name | REL(µg/m3) | Toxicological Endpoint | CAS # | |
| Ethylene glycol monobutyl ether | 1.5 x 103 | Blood | 111-76-2 | |
| Ethylene glycol monoethyl ether | 3.7 x 102 | Reproductive/developmental | 110-80-5 | |
| Ethylene glycol monoethyl ether acetate | 1.6 x 103 | Reproductive/developmental | 111-15-9 | |
| Ethylene glycol monomethyl ether | 3.2 x 102 | Reproductive/developmental | 109-86-4 |
| Name | REL(µg/m3) | Toxicological Endpoint | CAS # |
| Ethylene glycol monobutyl ether | 2.0 x 101 | Reproductive/Respiratory | 111-76-2 |
| Ethylene glycol monoethyl ether | 2.0 x 102 | Reproductive/Respiratory | 110-80-5 |
| Ethylene glycol monoethyl ether acetate | 6.4 x 101 | Reproductive/Respiratory | 111-15-9 |
| Ethylene glycol monomethyl ether | 2.0 x 101 | Reproductive/Respiratory | 109-86-4 |
| Ethylene glycol monomethyl ether acetate | 5.7 x 101 | Reproductive/Respiratory | 110-49-6 |
The United States Environmental Protection Agency (U.S. EPA) has established a Reference Concentration (RfC) for ethylene glycol monomethyl ether of 0.02 milligrams per cubic meter (mg/m3) based on testicular effects in rabbits. The U.S. EPA estimates that inhalation of this concentration or less, over a lifetime, would not likely result in the occurrence of chronic non-cancer results. The oral Reference Dose (RfD) is under review, and the provisional RfD is calculated to be 0.001 milligrams per kilogram per day (mg/kg/d). The U.S. EPA estimates that consumption of this dose or less, over a lifetime, would not likely result in the occurrence of chronic non-cancer effects. The U.S. EPA has established a RfC for ethylene glycol monoethyl ether of 0.2 mg/m3 based on decreased testis weight, seminiferous tubule degeneration, and decreased hemoglobin in rabbits, but has not established an oral RfD. However, a provisional oral RfD has been calculated to be 0.4 mg/kg/d.
No information is available on the reproductive or developmental effects of the glycol ethers in humans. Inhalation and oral exposure to several specific glycol ethers has been reported to result in testicular damage, reduced fertility, maternal toxicity, early embryonic death, birth defects, and delayed development in animal studies (U.S. EPA, 1994a). The State of California has determined under Proposition 65 that ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether, and ethylene glycol monomethyl ether acetate are male reproductive and developmental toxicants (CCR, 1996).
Cancer: No information is available on the carcinogenic effects of the glycol ethers in humans. No increase in tumors was reported in rats and mice exposed to ethylene glycol monoethyl ether by gavage. The U.S. EPA has not classified the glycol ethers for carcinogenicity (U.S. EPA, 1994a). The International Agency for Research on Cancer has not classified the glycol ethers as to human carcinogenicity (IARC, 1987a).
TABLE I - PHYSICAL PROPERTIES OF GLYCOL ETHERS
| Molecular Formula, Substance Name, & CAS Registry No. |
Synonyms |
Molecular Weight |
Boiling Point |
Melting Point |
Flash Point |
Vapor Density |
Vapor Pressure |
Density/ Specific Gravity |
Log Octanol/Water Partition Coefficient |
|
C6H14O3 Diethylene glycol dimethyl ether CAS No: 111-96-6 |
bis(2-methoxyethyl) ether; diglyme; diglycol methyl ether; 1,1'-oxybis(2-methyoxyethane) |
134.18 |
162 oC |
-68 oC |
158 oC |
--- |
2.96 mm Hg at 25 oC |
0.9451 at 20/20 oC |
-0.06 (est.) |
|
C8H18O3 Diethylene glycol monobutyl ether CAS No: 112-34-5 |
2-(2-butoxyethoxy)-ethanol; butyl digol |
162.23 |
230.6 oC |
-68.1 oC |
172 oF |
5.58 |
0.02 mm Hg at 25 oC |
0.9536 at 20/20 oC |
0.91 (est.) |
|
C6H14O3 Diethylene glycol monoethyl ether CAS No: 111-90-0 |
2-(2-ethoxyethoxy)-ethanol; diethylene glycol ethyl ether; diglycol monoethyl ether |
134.18 |
195 - 202 oC |
--- |
201 oF |
4.62 (air = 1) |
0.13 mm Hg at 25 oC |
0.9855 at 20/4 oC |
-0.15 (est.) |
|
C5H12O3 Diethylene glycol monomethyl ether CAS No: 111-77-3 |
2-(2-methoxyethoxy)-ethanol; methyl digol; methoxyethoxy ethanol; diethylene glycol methyl ether; diglycol monomethyl ether |
120.15 |
193 oC |
<-84 oC |
200 oF |
4.14 (air = 1) |
0.20 mm Hg at 25 oC |
1.035 at 20/4 oC |
-0.68 (est.) |
|
C6H14O2 Ethylene glycol diethyl ether CAS No: 629-14-1 |
1,2-diethoxyethane; ethyl glyme |
118.18 |
121.4 oC |
-74 oC |
95 oC (open cup) |
4.07 (air = 1) |
9.4 mm Hg at 20 oC |
0.8417 at 20/20 oC |
--- |
|
C4H10O2 Ethylene glycol dimethyl ether CAS No: 110-71-4 |
1,2-dimethoxyethane; glycol dimethyl ether; glyme; monogiyme; dimethaxyethane; 2.5-dioxahexane; ethylene dimethyl ether; monoethylene glycol dimethyl ether |
90.12 |
82 - 83 oC |
-58 oC (also reported at -71 oC) |
4.5 oC |
3.1 (air = 1) |
48 mm Hg at 20 oC |
0.86285 at 20/4 oC |
--- |
(Howard, 1990; Merck, 1989; Sax, 1989; U.S. EPA 1994)
TABLE I - PHYSICAL PROPERTIES OF GLYCOL ETHERS (CONTINUED)
| Molecular Formula, Substance Name, & CAS Registry No. |
Synonyms |
Molecular Weight |
Boiling Point |
Melting Point |
Flash Point |
Vapor Density |
Vapor Pressure |
Density/ Specific Gravity |
Log Octanol/Water Partition Coefficient |
|
C6H14O2 Ethylene glycol monobutyl ether CAS No.: 111-76-2 |
2-butoxyethanol; ethylene glycol-n-butyl ether; butyl glycol; glycol butyl ether; glycol monobutyl ether; monobutyl glycol ether |
118.18 |
171-172 oC |
-70 oC |
141oF (closed cup) |
4.1 |
0.76 mm Hg at 20 oC |
0.912 at 20/4 oC |
0.83 |
|
C4H10O2 Ethylene glycol monoethyl ether CAS No.: 110-80-5 |
2-ethoxyethanol; ethylene glycol ethyl ether; glycol ethyl ether; glycol monoethyl ether; hydroxy ether |
90.12 |
135 oC |
-70 oC |
120 oF (open cup) |
3.1 |
5.5 mm Hg at 25 oC |
0.931 at 20/20 oC |
-0.1 |
|
C6H12O3 Ethylene glycol monoethyl ether acetate CAS No.: 111-15-9 |
1-acetoxy-2-ethoxyethane; 2-ethoxyethyl acetate; 2-ethyoxethanol acetate |
132.16 |
156 oC |
-61.7 oC |
134 oF (open cup) |
4.72 |
1.6 mm Hg at 20 oC |
0.975 at 20/20 oC |
0.65 (est.) |
|
C3H8O2 Ethylene glycol monomethyl ether CAS No.: 109-86-4 |
2-methoxyethanol |
76.09 |
124.5 oC |
-85.1 oC |
115 oF |
2.62 (air = 1) |
9.5 mm Hg at 25 oC |
0.9663 at 20/4 oC |
-0.77 |
|
C5H10O3 Ethylene glycol monomethyl ether acetate CAS No.: 110-49-6 |
ethylene glycol methyl ether accetae; glycol monomethyl ether acetate; 2-methoxyethanol acetate |
118.13 |
145 oC |
-65.1 oC |
55.6 oC (open cup) |
4.1 (air = 1) |
2.0 mm Hg at 20 oC |
1.0067 at 20/20 oC |
--- |
|
C5H12O2 Ethylene glycol monopropyl ether CAS No.: 2807-30-9 |
monopropyl ether of ethylene glycol; 2-propoxyethanol |
104.15 |
150-152 oC |
--- |
--- |
--- |
2.9 mm Hg at 25 oC |
0.9112 at 20/4 oC |
--- |
|
CHO Triethylene glycol dimethyl ether CAS No.: 112-49-2 |
triglyme; 2,5,8,11-tetraoxadodecane |
178.22 |
216. oC |
-45 oC |
111 oC |
--- |
--- |
0.990 at 20/4 oC |
--- |
(Howard, 1990; Merck, 1989; Sax, 1989; U.S. EPA 1994)
TABLE II - PHYSICAL CHARACTERISTICS OF GLYCOL ETHERS
|
Glycol Ether |
Physical Characteristics |
Solubility |
Other Characteristics |
Glycol Ether |
Physical Characteristics |
Solubility |
Other Characteristics |
|
Diethylene glycol dimethyl ether |
Colorless liquid; Mild odor |
Miscible with water hydrocarbon solvents, alcohol, and ether |
Readily forms explosive peroxides upon exposure to air, light, or heat |
Ethylene glycol monoethyl ether |
Colorless liquid; Practically odorless; Slightly bitter taste |
Miscible with water, hydrocarbons, ether, acetone, alcohol, and liquid esters |
Solidifies at -70 oC; Dissolves many oils, resins, and waxes |
|
Diethylene glycol monobutyl ether |
Colorless liquid; Faint butyl odor |
Soluble in alcohol, ether, acetone, oils, benzene, water, and organic solvents |
Can react with oxidizing materials |
Ethylene glycol monoethyl ether acetate |
Colorless liquid; Mild ester-like odor |
Miscible with aromatic hydrocarbons; Slightly miscible with ether |
--- |
|
Diethylene glycol monoethyl ether |
Colorless liquid; Pleasant odor; Bitter taste |
Miscible with water, acetone, chloroform, benzene, ethanol, ether, and pyridine |
Hygroscopic; Slightly viscous; Stable |
Ethylene glycol monomethyl ether |
Colorless liquid; Mild agreeable odor |
Miscible with water, benzene, alcohols, ketones, glycols, hydrocarbons, and dimethylformamide |
Derived from ethylene oxide; Lowest boiling point and greatest rate of evaporation of all available glycol ethers |
|
Diethylene glycol monomethyl ether |
Colorless liquid; Pleasant odor; Bitter taste |
Miscible with water, alcohol, glycerol, ether, acetone, dimethylformamide |
Hygroscopic; Can react with oxidizing materials |
Ethylene glycol monomethyl ether acetate |
Colorless liquid; Pleasant odor |
Miscible with water, oils, and most organic solvents |
Stable; Solidifies at -70 oC |
|
Ethylene glycol diethyl ether |
Colorless liquid; Sweetish odor; Bitter taste |
Immiscible with water; Soluble in oils, alcohol, ether, acetone, benzene, and organic solvents |
Aprotic solvents (a type of solvent which neither donates or accepts protons) |
Ethylene glycol monopropyl ether |
Volatile liquid; Mild ethereal odor; Bitter taste |
Soluble in water, alcohol, and ether |
--- |
|
Ethylene glycol dimethyl ether |
Colorless liquid; Sharp ethereal odor |
Miscible with water, alcohol; Soluble in hydrocarbon solvents, chloroform, ether |
--- |
Triethylene glycol dimethyl ether |
Water-white liquid; Mild ether odor |
Miscible with water and hydrocarbon solvents; Completely soluble in water and hydrocarbons at 20oC |
May contain peroxides |
|
Ethylene glycol monobutyl ether |
Colorless liquid; Pleasant odor; Mobile liquid |
Soluble in water, organic solvents, and mineral oils; Mixes with acetone, benzene, carbon tetrachloride, ethyl ether, n-heptane, ketones, ethers, alcohols, aromatic paraffin, and halogenated hydrocarbons |
High dilution ratio with petroleum hydrocarbons |
--- |
--- |
--- |
--- |
(Howard, 1990; Merck, 1989; Sax, 1989; U.S. EPA 1994)
TABLE III - SOURCES, USES, AND EMISSIONS OF GLYCOL ETHERS
|
Glycol Ether |
California Emission Estimates (Lbs/Yr) |
Major Uses |
Glycol Ether |
California Emission Estimates (Lbs/Yr) |
Major Uses |
|
Diethylene glycol dimethyl ether |
260 |
Solvent: Anhydrous reaction medium for organo-metallic synthesis |
Ethylene glycol monomethyl ether |
30,000 |
Solvent: Jet fuel anti-icing additive; Chemical intermediate; Plasticizer; In liquid soaps, cosmetics, painting plasters, hydraulic fluids, and cleaning compounds |
|
Diethylene glycol monoethyl ether |
5,500 |
Solvent: Plasticizer intermediate; Brake fluid diluent |
Ethylene glycol monomethyl ether acetate |
3,100 |
Solvent: In textile printing, photographic film, and silk-screening inks |
|
Diethylene glycol monobutyl ether |
26,000 |
Solvent: In textile printing; Brake fluid diluent; Chemical intermediate |
Ethylene glycol monopropyl ether |
12,000 |
--- |
|
Diethylene glycol monomethyl ether |
6,500 |
Solvent: Chemical intermediate; Brake fluid diluent; Coupling agent |
Triethylene glycol dimethyl ether |
2,800 |
Solvent: Coupling agent |
|
Ethylene glycol diethyl ether |
No emissions reported |
Inert reaction medium; Solvent: Organic synthesis; Apriotic solvent; Detergent diluent |
Ethylene glycol dimethyl ether |
9,700 |
Solvent: Extractant; Additive in diesel fuel, lubricants, and pesticides |
|
Ethylene glycol monobutyl ether |
430,000 |
In hydraulic fluids; Solvent; Household cleaners; Chemical intermediate; Coupling agent |
Ethylene glycol monoethyl ether |
320,000 |
Solvent; Anti-icing agent; Chemical intermediate |
|
Ethylene glycol monoethyl ether acetate |
150,000 |
Solvent; Automobile lacquers |
(Howard, 1990; Merck, 1989; Sax, 1989; U.S. EPA 1994)