111-76-2

Basic information

• Product Name: 2-Butoxyethanol
• Synonyms: 2-(1-butoxy)ethanol;2-be;2-Butossi-etanolo;2-Butoxy-1-ethanol;2-Butoxy-aethanol;2-Butoxyethan-1-ol;2-butoxy-ethano;2-butoxyethanol (butyl cellosolve)
• CAS NO: 111-76-2
• Molecular Formula: C₆H₁₄O₂
• Molecular Weight: 118.17416
• EINECS: 203-905-0
• Product Categories: Ethylene Glycols & Monofunctional Ethylene Glycols;Monofunctional Ethylene Glycols;Amber Glass Bottles;Reagent;Solvent Bottles;Solvent Packaging Options;Solvents;ACS and Reagent Grade Solvents;Carbon Steel Flex-Spout Cans;ReagentPlus;ReagentPlus Solvent Grade Products;Semi-Bulk Solvents;Solvent by Application;solvent,make paints and varnish
• Mol File: 111-76-2.mol
• Article Data: 63

Chemical Properties

• Melting Point: -70 °C
• Boiling Point: 171 °C
• Flash Point: 140 °F
• Appearance: Clear/Liquid
• Density: 0.902 g/mL at 25 °C(lit.)
• Vapor Density: 4.1 (vs air)
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.419(lit.)
• Storage Temp.: Store at room temperature.
• Solubility: 900g/l completely miscible
• PKA: 14.42±0.10(Predicted)
• Explosive Limit: 1.1-10.6%(V)
• Water Solubility: miscible
• Merck: 14,1559
• BRN: 1732511
• CAS DataBase Reference: 2-Butoxyethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butoxyethanol(111-76-2)
• EPA Substance Registry System: 2-Butoxyethanol(111-76-2)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/38
• Safety Statements: 36/37-46
• RIDADR: 1986
• WGK Germany: 1
• RTECS: KJ8575000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 111-76-2(Hazardous Substances Data)

Usage

Chemical Reactivity

Reactivity 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.

Uses

Ethylene glycol n-butyl ether (EB) is used widely as a coupling solvent because of its superior coupling efficiency and excellent solvency for resins.

Uses

Solvent for nitrocellulose, resins, grease, oil, albumin; dry cleaning.

Precautions

Occupational 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.

storage

2-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.

Chemical Properties

2-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.

Chemical Properties

Ethylene 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.

Air & Water Reactions

2-Butoxyethanol is sensitive to air and light. Slightly soluble in water.

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 1095, 1980 DOI: 10.1021/jo01294a034

Potential Exposure

2-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

Fire Hazard

Combustible 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.

Safety Profile

Poison 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

Physical properties

Clear, 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).

Purification Methods

Peroxides 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.]

Health Hazard

2-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.

General Description

A 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.

Description

2-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.

Incompatibilities

May 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 Disposal

EGBE 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.

Uses

Ethylene glycol monobutyl ether (EGBE) is used as a solvent for nitrocellulose, resins, oil, and grease, and in dry cleaning.

Hazard

A toxic material. Eye and upper respiratory tract irritant. Questionable carcinogen.

Environmental fate

Biological. 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 2.31 g/g. 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).

Reactivity Profile

ETHYLENE 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. .

InChI:InChI=1/C6H14O2/c1-3-4-5-8-6(2)7/h6-7H,3-5H2,1-2H3

Synthetic route

ethene (74-85-1) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With dihydrogen peroxide Green chemistry;	98.5%

oxirane (75-21-8) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With aluminum tri-n-butoxide; acetic acid at 170℃; for 24h; Reagent/catalyst; Autoclave;	97.75%
With MCM-41-500 ° C catalyst at 100℃; for 4h; Reagent/catalyst; Temperature; Autoclave; High pressure;	86.8%
In dodecane at 100℃; Kinetics;

oxirane (75-21-8) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2) + Diethylene glycol monobutyl ether (112-34-5)

Conditions	Yield
With potassium aluminum sulfate at 170℃; for 24h; Reagent/catalyst; Autoclave;	A 93.1% B 6.63%

-butyl vinyl ether (111-34-2) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
Stage #1: -butyl vinyl ether With borane-ammonia complex In tetrahydrofuran at 90℃; for 3h; Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 20℃; for 3h;	59%

[1,3]-dioxolan-2-one (96-49-1) + sodium butanolate (2372-45-4) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With benzene at 100℃;

[1,3]-dioxolan-2-one (96-49-1) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With dimethyl sulfate at 130℃;

1,1-bis-(2-methoxy-ethoxy)-butane (71808-63-4) → 2-Butoxyethanol (111-76-2) + 1-(2-methoxy-ethoxy)-butane (13343-98-1)

Conditions	Yield
With nickel at 200 - 240℃; under 51485.6 - 77228.3 Torr; Hydrogenation;

Methyl butoxyacetate (10228-54-3) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With ethanol; copper oxide-chromium oxide at 200℃; under 147102 Torr; Hydrogenation;

butyl butoxyacetate (10397-22-5) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With copper-chromium-iron at 280℃; under 95616 Torr; Hydrogenation;

ethylene glycol (107-21-1) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With sodium und anschliessenden Erhitzen mit 1-Brom-butan;

n-Butyl chloride (109-69-3) + ethylene glycol (107-21-1) → 2-Butoxyethanol (111-76-2) + 1,2-dibutoxyethane (112-48-1)

Conditions	Yield
(i) DMSO, NaOH, (ii) /BRN= 1730909/; Multistep reaction;

2-propyl-1,3-dioxolane (3390-13-4) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction;
In ethylene glycol
With hydrogen; 0.6 wt % palladium on alumina at 210℃; under 16274.9 Torr; Product distribution / selectivity;

2-propyl-1,3-dioxolane (3390-13-4) → 2-Butoxyethanol (111-76-2) + ethylene glycol (107-21-1)

Conditions	Yield
With lithium aluminium tetrahydride; boron trichloride 1.) CH2Cl2, 0.2 h, 2.) Et2O, 30 min; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2-ethoxy-ethanol (110-80-5) + 1-butyl-1-nitrosourea (869-01-2) → butyl ethyl ether (628-81-9) + 2-Butoxyethanol (111-76-2) + 1-(2-Ethoxyethoxy)butan (4413-13-2) + ethylene glycol sec-butyl ethyl ether (77078-19-4)

Conditions	Yield
With potassium carbonate Ambient temperature; Further byproducts given;	A 2.7 % Chromat. B 1.8 % Chromat. C 83.2 % Chromat. D 11.6 % Chromat.
With sodium hydrogencarbonate for 24h; Ambient temperature; Further byproducts given;	A 1.3 % Chromat. B 2.9 % Chromat. C 81.9 % Chromat. D 12.6 % Chromat.

2-ethoxy-ethanol (110-80-5) + 1-butyl-1-nitrosourea (869-01-2) → 2-Butoxyethanol (111-76-2) + monoethylene glycol diethyl ether (629-14-1) + 1-(2-Ethoxyethoxy)butan (4413-13-2) + ethylene glycol sec-butyl ethyl ether (77078-19-4)

Conditions	Yield
With sodium hydrogencarbonate for 24h; Ambient temperature; Further byproducts given;	A 2.9 % Chromat. B 0.9 % Chromat. C 81.9 % Chromat. D 12.6 % Chromat.

butyl butoxyacetate (10397-22-5) + Cu-Cr-Fe-catalyst → 2-Butoxyethanol (111-76-2)

Conditions	Yield
at 280℃; under 95616 Torr; Anfangsdruck.Hydrogenation;

1-iodo-butane (542-69-8) + monosodium compound of ethylene glycol → 2-Butoxyethanol (111-76-2)

formaldehyde-<2-butyloxy-ethylacetal> → 2-Butoxyethanol (111-76-2) + 1-(2-methoxy-ethoxy)-butane (13343-98-1)

Conditions	Yield
With nickel at 200 - 240℃; under 51485.6 - 77228.3 Torr; Hydrogenation;

2-methoxy-ethanol (109-86-4) + 1-butyl-1-nitrosourea (869-01-2) → 1,2-dimethoxyethane (110-71-4) + butyl methyl ether (628-28-4) + 2-Butoxyethanol (111-76-2) + 2-(1-Methylpropoxy)ethanol (7795-91-7) + 1-(2-methoxy-ethoxy)-butane (13343-98-1) + 2-(2-Methoxyethoxy)butan + butenes, butanols, sBuOMe

Conditions	Yield
With potassium carbonate for 0.0833333h; Product distribution; Mechanism; Ambient temperature; further reagent: NaHCO3, further reactions with EtOCH2CH2OH, MeOH-oxirane, -oxetane, -tetrahydrofuran;	A 0.5 % Chromat. B 2.9 % Chromat. C 7.2 % Chromat. D 0.5 % Chromat. E 74.4 % Chromat. F 14.2 % Chromat. G n/a

...Expand

oxirane (75-21-8) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2) + Diethylene glycol monobutyl ether (112-34-5) + triethyleneglycol monobutyl ether (143-22-6)

Conditions	Yield
2,4,6-trimethyl-pyridine at 160℃; under 2311.54 - 3345.86 Torr; for 2.5h; Product distribution / selectivity; Inert atmosphere;
sodium butanolate at 140℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;	A 20.16 %Chromat. B 9.07 %Chromat. C 6.10 %Chromat.
catalyst of invention (Sb2O3, copper acetate, hydrogen peroxide; calcined) at 140℃; under 30003 Torr; for 24 - 120h; Product distribution / selectivity;	A 76 - 77 %Chromat. B 13 - 14 %Chromat. C 9 %Chromat.

di-n-butyloxymethane (2568-90-3) → 2-Butoxyethanol (111-76-2)

Ru3 (CO)12 + HCCo(CO)9 + Dimethoxymethane (109-87-5) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With carbon monoxide; hydrogen In butan-1-ol

butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With hydrogen; paraformaldehyde

diphenyl sulfide (139-66-2) + butan-1-ol (71-36-3) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With hydrogen; paraformaldehyde

Tetraethylene glycol (112-60-7) + ethylene glycol (107-21-1) + butyraldehyde (123-72-8) + diethylene glycol (111-46-6) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 2-propyl-1,3-dioxolane (3390-13-4) + 2-Butoxyethanol (111-76-2) + Diethylene glycol monobutyl ether (112-34-5) + triethyleneglycol monobutyl ether (143-22-6) + tetraethylene glycol monobutyl ether (1559-34-8) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h;

...Expand

ethylene glycol (107-21-1) + butyraldehyde (123-72-8) → 2-Butoxyethanol (111-76-2) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h; Product distribution / selectivity; Inert atmosphere;	A 88.7 %Chromat. B 7.2 %Chromat.
With hydrogen; 5%-palladium/activated carbon at 200℃; under 25877.6 Torr; for 1h; Autoclave;
With palladium 10% on activated carbon; hydrogen at 180℃; under 51755.2 Torr; for 2h; Temperature; Concentration;	A 88.7 %Chromat. B 7.2 %Chromat.

ethylene glycol (107-21-1) + butyraldehyde (123-72-8) → 2-Butoxyethanol (111-76-2) + 1,2-dibutoxyethane (112-48-1) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 180℃; under 51716.2 Torr; for 2h; Product distribution / selectivity; Inert atmosphere;	A 79.7 %Chromat. B 7.7 %Chromat. C 7.5 %Chromat.
With palladium 10% on activated carbon; hydrogen at 180℃; under 51755.2 Torr; for 2h;	A 79.7 %Chromat. B 7.7 %Chromat. C 7.5 %Chromat.

ethylene glycol (107-21-1) + butyraldehyde (123-72-8) → 2-Butoxyethanol (111-76-2)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 180℃; under 25858.1 Torr; for 3h; Product distribution / selectivity; Inert atmosphere;	85.5 %Chromat.
With palladium 10% on activated carbon; hydrogen at 180℃; under 26252.6 Torr; for 3h;	85.5 %Chromat.

Upstream product

• 1310-58-3 Potassium hydroxide 
• 108-90-7 Chlorobenzene 
• 123-30-8 4-Aminophenol 
• 67-56-1 Methanol 
• 64-17-5 Etanol 
• 7758-98-7 Copper(II) sulfate 

Downstream Products

• 112-34-5 Butyldiglycol 

Recommend Products

• 101082-17-1  1-butoxy-2-nonyloxy-ethane 
• 111-76-2  2-Butoxyethanol 
• 693-58-3  1-Bromononane 
• 7770-34-5  3-butoxy-propionic acid-(2-butoxy-ethyl ester) 
• 14144-48-0  butyl 3-butoxypropionate 
• 86219-10-5  3-(2-butoxy-ethoxy)-acrylic acid-(2-butoxy-ethyl ester) 
• 10601-80-6  ethyl 3,3-diethoxypropanoate 
• 63021-22-7  2,5,8-trioxa-nonanedioic acid bis-(2-butoxy-ethyl ester) 
• 106-75-2  diethylene glycol bischloroformate 
• 2545-59-7  (2,4,5-trichloro-phenoxy)-acetic acid-(2-butoxy-ethyl ester) 
• 93-76-5  2,4,5-Trichlorophenoxyacetic acid 
• 107-21-1  ethylene glycol 
• 16006-08-9  carbamic acid-(2-butoxy-ethyl ester) 
• 57-13-6  urea 

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