ChemicalBook > Product Catalog > Organic Chemistry > Ethers and derivatives > Ethers, ether-alcohols > 2-Butoxyethanol
2-Butoxyethanol Chemical Properties
- Melting point:-70 °C
- Boiling point:171 °C
- Density 0.902 g/mL at 25 °C(lit.)
- vapor density 4.1 (vs air)
- vapor pressure <1 mm Hg ( 20 °C)
- refractive index n
- Flash point:140 °F
- storage temp. Store below +30°C.
- solubility 900g/l completely miscible
- form Liquid
- color Clear
- OdorMild, characteristic; slightly rancid; mild ethereal.
- PH7 (H2O, 20℃)(as aqueous solution)
- explosive limit1.1-10.6%(V)
- Odor Threshold0.043ppm
- Water Solubility miscible
- λmaxλ: 230 nm Amax: 1.0
λ: 250 nm Amax: 0.10
λ: 275 nm Amax: 0.05
λ: 300-400 nm Amax: 0.01
- Merck 14,1559
- BRN 1732511
- Henry's Law Constant(x 10-6 atm?m3/mol): 2.36 (approximate - calculated from water solubility and vapor pressure)
- Exposure limitsTLV-TWA skin 25 ppm (121 mg/m3) (ACGIH), 50 ppm (242 mg/m3) (OSHA); STEL 75 ppm (363 mg/m3) (ACGIH);IDLH 700 ppm (NIOSH). .
- CAS DataBase Reference111-76-2(CAS DataBase Reference)
- NIST Chemistry Reference2-n-Butoxy-1-ethanol(111-76-2)
- IARC3 (Vol. 88) 2006
- EPA Substance Registry SystemEthylene glycol monobutyl ether (111-76-2)
- Hazard Codes Xn
- Risk Statements 20/21/22-36/38
- Safety Statements 36/37-46
- RIDADR 1986
- WGK Germany 1
- RTECS KJ8575000
- Autoignition Temperature473 °F
- TSCA Yes
- HS Code 2909 43 00
- HazardClass 6.1
- PackingGroup III
- Hazardous Substances Data111-76-2(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 1.48 g/kg (Smyth)
2-Butoxyethanol Usage And Synthesis
- Description2-Butoxyethanol is a clear, colourless liquid with ether-like smell.2-Butoxyethanol is usually produced by a reaction of ethylene oxide with butyl alcohol, but it may also be made by the reaction of ethylene glycol with dibutyl sulphate. 2-Butoxyethanol is widely used as a solvent in protective surface coatings such as spray lacquers, quick-dry lacquers, enamels, varnishes, and latex paints. It is also used as an ingredient in paint thinners and strippers, varnish removers, agricultural chemicals, herbicides, silicon caulks, cutting oils, and hydraulic fluids and as metal cleaners, fabric dyes and inks, industrial and household cleaners (as a degreaser), and dry-cleaning compounds. It is also used in liquid soaps and in cosmetics. 2-Butoxyethanol acetate has been reported to be present in air, water, and soil as a contaminant and exposure to it occurs during its manufacture and use as an intermediate in the chemical industry, and during the formulation and use of its products in multiple industrial activities. The acetate form of 2-butoxyethanol is 2-butoxyethanol acetate and also known as ethylene glycol monobutyl ether acetate.
- Chemical PropertiesEthylene glycol monobutyl ether is a colorless liquid with a mild, rancid, ether-like odor. It is miscible in alI proportions with many ketones, ethers, alcohols, aromatic paraffin and halogenated hydrocarbons. More specifically, it mixes in all proportions with acetone, benzene, carbon tetrachloride, ethyl ether, n-heptane and water. Because of its excellent solvency, low evaporation rate and high dilution ratios, it is used as a solvent in the manufacture and formulation of lacquers, enamels, inks and varnishes, employing such resins as alkyd, phenolic, nitrocellulose, maleic modified, styrene and epoxy. In lacquers butyl "Cellosolve" imparts a slow evaporation rate, strengthens blush resistance, heightens gloss, improves flow-out and helps prevent orange peel. Hot spray lacquers usually contain about 10% of "Dowanol" EB based on the solvent-diluent weight.
- Chemical Properties2-Butoxyethanol is a clear colorless liquid with an ether-like smell and belongs to the family of glycol ether/alkoxy alcohol. 2-Butoxyethanol is miscible in water and soluble in most organic solvents. 2-Butoxyethanol does not occur naturally. It is usually produced by reacting ethylene oxide with butyl alcohol.
2-Butoxyethanol is used as a solvent for nitrocellulose, natural and synthetic resins, soluble oils, in surface coatings, spray lacquers, enamels, varnishes, and latex paints, as an ingredient in paint thinners, quick-dry lacquers, latex paint, and strippers, varnish removers, and herbicides. It is also used in textile dyeing and printing, in the treatment of leather, in the production of plasticizers, as a stabilizer in metal cleaners and household cleaners, and in hydraulic fl uids, insecticides, herbicides, and rust removers. It is also used as an ingredient in liquid soaps, cosmetics, industrial and household cleaners, dry-cleaning compounds, and as an ingredient in silicon caulks, cutting oils, and hydraulic fluids. 2-Butoxyethanol is a fire hazard when exposed to heat, sparks, or open flames.
- Physical propertiesClear, colorless, oily liquid with a mild, ether-like odor. Experimentally determined detection and recognition odor threshold concentrations were 500 μg/m3 (100 ppbv) and 1.7 mg/m3 (350 ppbv), respectively (Hellman and Small, 1974). An odor threshold concentration of 580 ppbv was reported by Nagata and Takeuchi (1990).
- UsesEthylene glycol n-butyl ether (EB) is used widely as a coupling solvent because of its superior coupling efficiency and excellent solvency for resins.
- UsesEthylene glycol monobutyl ether (EGBE) is used as a solvent for nitrocellulose, resins, oil, and grease, and in dry cleaning.
- UsesSolvent for nitrocellulose, resins, grease, oil, albumin; dry cleaning.
- Synthesis Reference(s)The Journal of Organic Chemistry, 45, p. 1095, 1980 DOI: 10.1021/jo01294a034
- General DescriptionA colorless liquid with a mild, pleasant odor. Less dense than water. Flash point 160°F. Irritates skin and eyes and may be toxic by ingestion. Used as a solvent and to make paints and varnish.
- Air & Water Reactions2-Butoxyethanol is sensitive to air and light. Slightly soluble in water.
- Reactivity ProfileETHYLENE GLYCOL N-BUTYL ETHER may react with bases, aluminum and oxidizing materials. 2-Butoxyethanol is liable to form peroxides on exposure to air and light. 2-Butoxyethanol attacks some forms of plastics, rubber and coatings. .
- HazardA toxic material. Eye and upper respiratory tract irritant. Questionable carcinogen.
- Health Hazard2-Butoxyethanol is present in a variety of consumer products, including cleaning agents and surface coatings, such as paints, lacquers, and varnishes. 2-Butoxyethanol is readily absorbed following inhalation, oral, and dermal exposure. 2-Butoxyethanol is released into air or water by different industrial activities and facilities that manu facture, process, or use the chemical. Exposure to 2-butoxyethanol causes irritating effects to the eyes and skin, but it has not induced skin sensitization in guinea pigs. Information on the human health effects associated with exposure to 2-butoxyethanol is limited. However, case studies of individuals who had attempted suicide by ingest ing 2-butoxyethanol-containing cleaning solutions suffered poisoning with symp toms such as hemoglobinuria, erythropenia, and hypotension, metabolic acidosis, shock, non-cardiogenic pulmonary edema, and albuminuria, hepatic disorders and hematuria.
- Fire HazardCombustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Safety ProfilePoison by ingestion, skin contact, intraperitoneal, and intravenous routes. Moderately toxic via inhalation and subcutaneous routes. Human systemic effects by inhalation: nausea or vomiting, headache, unspecified eye effects. Experimental teratogenic and reproductive effects. A skin irritant. Combustible liquid when exposed to heat or flame. To fight fire, use foam, CO2, dry chemical. Incompatible with oxidizing materials, heat, and flame. When heated to decomposition it emits acrid smoke and irritating fumes
- Potential Exposure2-Butoxy ethanol is a colorless liquid with a mild, ether like odor. Molecular weight 5 118.20; Specific gravity (H2O:1) 5 0.90; boiling point 5 171C; freezing/ melting point 5 274.8C; vapor pressure 5 0.8 mmHg @ 20C; Relative vapor density (air 5 1) 5 4.1; Flash point = 61C (cc); Autoignition temperature = 238C
- Environmental FateBiological. Bridié et al. (1979) reported BOD and COD values of 0.71 and 2.20 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. When a sewage seed was used in a
separate screening test, a BOD value of 0.20 g/g was obtained. The ThOD for 2-butoxyethanol is
Chemical/Physical. At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 441 mg/L. The adsorbability of the carbon used was 112 mg/g carbon (Guisti et al., 1974).
- storage2-Butoxyethanol should be kept stored in tightly closed, grounded containers in a cool area with adequate ventilation, away from normal work areas and sources of heat and sparks, and electrical equipment. At the storage and handling area, workers should use solvent resistant materials.
- Purification MethodsPeroxides can be removed by refluxing with anhydrous SnCl2 or by passage under slight pressure through a column of activated alumina. Dry with anhydrous K2CO3 and CaSO4, filter and distil, or reflux with, and distil from NaOH. [Beilstein 1 IV 2380.]
- Toxicity evaluationThe principal toxicological effect observed upon overexposure
to EGBE is the destruction of red blood cells (RBCs) (i.e.,
hemolysis). BAA, the predominant oxidative metabolite of
EGBE, appears responsible for this hemolytic activity. It has
been speculated that BAA may interact with RBC membranes,
disrupting erythrocyte osmotic balance, leading to cellular
swelling, loss of deformability, and eventually hemolysis. In
studies with male rats, treatment with alcohol dehydrogenase
inhibitors protected against EGBE-induced hematotoxicity and
inhibited EGBE metabolism to BAA. Another event in the
sequelae following EGBE exposures is compensatory erythropoiesis,
where as a response to the loss of erythrocytes, the bone
marrow increases production of young RBCs.
In vitro studies have indicated that the RBCs of rats, mice, rabbits, and baboons are susceptible to hemolysis by BAA, whereas blood from pigs, dogs, cats, guinea pigs, and humans are resistant. A number of other studies have confirmed these results in vitro, in RBCs from a large cross-section of the human population, including those with hereditary red cell disease (i.e., sickle cell and spherocytosis) and the aged. These studies indicate that human cells are not as susceptible to hemolysis as rat cells tested under similar conditions. These findings suggest that humans exposed to equivalent doses of EGBE would not be expected to exhibit the same spectrum or severity of hematotoxic-related effects as those produced in rats. In vitro experimental results also suggest that RBCs are more sensitive to hemolysis by BAA than to hemolysis by EGBE.
- IncompatibilitiesMay form explosive mixture with air. Can form unstable and explosive peroxides; check for peroxides prior to distillation; render harmless if positive. Decomposes, producing toxic fumes. Violent reaction with strong caustics and strong oxidizers. Attacks some coatings, plastics and rubber. Attacks metallic aluminum at high temperatures.
- Waste DisposalEGBE is destroyed by burning in an incinerator. In the laboratory, small amounts may be disposed of in the sink with a large volume of water.
- PrecautionsOccupational workers should use minimal quantities of 2-butoxyethanol in designated areas with adequate ventilation and away from sources of heat or sparks. Whenever pos sible, fi re-resistant containers should be used. Wear appropriate protective equipment to prevent skin and eye contact.
2-Butoxyethanol Preparation Products And Raw materials
- 2-Ethoxyethanol 2,5-Furandione,ethenylbenzene polymer,ammonium salt,2-butoxyethanol ester,2,5-Furandione, ethenylbenzene polymer, ammonium salt, 2-butoxyethanol ester N-ETHYL-N-(HEPTADECAFLUOROOCTYL-SO2)GLYC IN K SALT,42 WT% IN H2O/2-BUTOXYETHANOL ETHYLENE GLYCOL MONO TERT-BUTYL ETHER (2-TERT-BUTOXYETHANOL) TRIS(2-BUTOXYETHANOL)PHOSPHATE,Tri(2-butoxyethanol)phosphate,2-BUTOXYETHANOL PHOSPHATE 1,2-Benzenedicarboxylic acid, esters with by-products from manuf. of 2-butoxyethanol 2,4-D Butoxyethanol ester,(2,4-Dichlorophenoxy)acetic acid butoxyethanol ester,Butoxyethanol ester of 2,4-D 1-(1-Methylethoxy)-. 2-propanol. 2-Butoxyethanol ETHYLENE GLYCOL MONO-N-BUTYL ETHER = 2-BUTOXYETHANOL = BUTYL CELLOSOLVE Boric acid (H3BO3), reaction products with by-products from manuf. of 2-butoxyethanol triclopyr, butoxyethanol ester 2-Butoxyethanol/phosphoric acid/potassium,(1:x:x) salt Siloxanes and Silicones, di-Me, [(methylsilylidyne) tris (oxy)] tris-,hydroxy-terminated, ethers with polyethylene-polypropylene glycol mono-Bu ether 1,3-Propanediol, 2-ethyl-2-(hydroxymethyl)-, polymer with 1,3-diisocyanatomethylbenzene, 2-butoxyethanol-blocked Poly[oxy(methyl-1,2-ethanediyl)], α-hydro-ω-hydroxy-, polymer with 1,6-diisocyanatohexane, 2-butoxyethanol-blocked 1-Butoxyethanol 2-Butoxyethanol benzoate butyl rubber
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