111-76-2 Usage
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.
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).
Uses
Different sources of media describe the Uses of 111-76-2 differently. You can refer to the following data:
1. 2-Butoxyethanol is a reagent in the synthesis of 4-butoxyethoxy-N-octadecyl-1,8-naphthalimide as a new fluorescent probe for the determination of proteins. Also used as a reagent in the synthesis of 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors.
2. Ethylene glycol n-butyl ether (EB) is used widely as a coupling solvent because of
its superior coupling efficiency and excellent solvency for resins.
3. Ethylene glycol monobutyl ether (EGBE) is used as a solvent for nitrocellulose, resins, oil, and grease, and in dry cleaning.
4. Solvent 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 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.
Air & Water Reactions
2-Butoxyethanol is sensitive to air and light. Slightly soluble in water.
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. .
Hazard
A toxic material. Eye and upper respiratory
tract irritant. Questionable carcinogen.
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.
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.
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.
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
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
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).
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.
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.]
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 111-76-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 111-76:
(5*1)+(4*1)+(3*1)+(2*7)+(1*6)=32
32 % 10 = 2
So 111-76-2 is a valid CAS Registry Number.
InChI:InChI=1/C6H14O2/c1-3-4-5-8-6(2)7/h6-7H,3-5H2,1-2H3
111-76-2Relevant articles and documents
Preparation method of alkyl diglycol (by machine translation)
-
Paragraph 0031; 0032; 0040-0049, (2020/06/09)
The invention relates to a preparation method of alkyl diglycol with NRE (narrow distribution ethoxylate Narrow Range Ethoxylate) effect while increasing the reaction speed in the presence of a novel aluminum-based catalyst containing alkali metal or alkaline earth metal. (by machine translation)
OPEN-FLASK HYDROBORATION AND THE USE THEREOF
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Paragraph 0046; 0058; 0059, (2018/03/25)
The present disclosure generally relates to a process for hydroboration of an alkene or alkyne using ammonia borane (AB). In particular, the present invention relates to hydroboration of an alkene or alkyne in the presence of air or moisture, and a clean process for facile preparation of an alcohol by oxidizing the organoborane so formed with hydrogen peroxide. The products, including aminodialkylboranes, ammonia trialkylborane complexes, as well as various alcohols so prepared, are within the scope of this disclosure.
Preparation method of ethylene glycol monobutyl ether
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Paragraph 0019; 0021, (2017/07/18)
The invention relates to the field of chemistry and chemical engineering and particularly discloses a preparation method of ethylene glycol monobutyl ether. The preparation method of the ethylene glycol monobutyl ether is characterized in that ethylene oxide and n-butyl alcohol are prepared into a raw material mixed solution, and cold storage is performed for usage; high-silicon-content alloy or an all-silicon molecular sieve and porous silicon dioxide are put in a muffle furnace to perform high-temperature roasting, and a roasting catalyst is put in a dryer for usage after being numbered; the raw material solution and the roasting catalyst are put in a reaction kettle for reaction, and a product is obtained. The high-silicon-content alloy or the all-silicon molecular sieve and the porous silicon dioxide used by the method is low in procurement cost, the treating process is simple, a production process is greatly simplified, the production cost is reduced, the catalyst or ethylene glycol butyl ether is high in selectivity, and the preparation method has very high stability.
Green synthesis method for preparing alcohol ether by using olefin in one step
-
Paragraph 0018, (2018/01/12)
The invention belongs to the field of organic chemical industry, and provides a green synthesis method for preparing alcohol ether by using olefin in one step. The green synthesis method is characterized in that a jet type reactor is used for continuously jetting alcohol, hydrogen peroxide and a cyclization-alcoholysis catalyst into a pressured reaction kettle filled with olefin gas, so that continuous epoxidation and alcoholysis reaction is carried out; after being separated by a ceramic membrane, reaction liquid enters to an olefin and alcohol removal tower; after olefin and alcohol are removed, the reaction liquid directly and continuously enters to a rectifying tower, and the alcohol ether product is obtained by rectifying; the effective utilization rate of the hydrogen peroxide is more than or equal to 98%, the alcohol ether selectively is greater than or equal to 99%, and the product purity is higher than or equal to 99.5%. The green synthesis method can be used for preparing the alcohol ether in one step and is suitable for industrial large-scale production.
Method for preparing butoxy methoxy methane
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Paragraph 0018; 0019, (2017/03/28)
The invention provides a method for preparing butoxy methoxy methane and relates to a method for preparing methane. The method includes a synthesis path of ethylene glycol monobutyl ether, the path includes three steps that 1, methylal and butyl alcohol synthesize the butoxy methoxy methane; 2, directional carbonylation of the butoxy methoxy methane is conducted, and butoxy methyl acetate is generated; 3, hydrogenation is conducted on the butoxy methyl acetate to generate the ethylene glycol monobutyl ether and methane; dimethoxymethane and n-butyl alcohol serve as raw materials, under the temperature and pressure, resin serves as a catalyst, the butoxy methoxy methane is prepared. The brand new synthesis path of the ethylene glycol monobutyl ether and the preparation method of the butoxy methoxy methane are developed; the required raw materials are cheap and easy to obtain, the whole procedure is simple in operation, a product is singular and high in selectivity, good application prospect is achieved, and the butoxy methoxy methane is suitable for industrial production.
A non-dissociative open-flask hydroboration with ammonia borane: Ready synthesis of ammonia-trialkylboranes and aminodialkylboranes
Ramachandran, P. Veeraraghavan,Drolet, Michael P.,Kulkarni, Ameya S.
supporting information, p. 11897 - 11900 (2016/10/09)
Under open-flask conditions, ammonia borane hydroborates olefins in refluxing tetrahydrofuran. Unlike conventional hydroboration, the Lewis base (ammonia) is not dissociated from the boron center. Terminal alkenes selectively provide ammonia-trialkylborane complexes. On the other hand, internal alkenes afford aminodialkylboranes via a metal-free hydroboration-dehydrogenation sequence. Alkaline hydrogen peroxide oxidation of the products provides the corresponding alcohols in high yields.
PRODUCTION OF HYDROXY ETHER HYDROCARBONS BY VAPOR PHASE HYDROGENOLYSIS OF CYCLIC ACETALS AND KETALS
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Page/Page column 11, (2013/02/28)
A vapor phase hydrogenolysis reaction to convert cyclic acetal compounds and/or cyclic ketal compounds in the presence of hydrogen to their corresponding hydroxy ether hydrocarbon reaction products using a supported noble metal catalyst. The hydrogenolysis reaction can be carried out in the vapor phase and in the absence of a polyhydroxyl hydrocarbon co-solvent.
CATALYSTS FOR THE PRODUCTION OF HYDROXY ETHER HYDROCARBONS BY VAPOR PHASE HYDROGENOLYSIS OF CYCLIC ACETALS AND KETALS
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Page/Page column 18, (2013/02/28)
Catalyst compositions of palladium supported on alumina or zirconium oxide supports having low or no silicon dioxide contents and having a specific surface area or modified with alkali, alkaline earth, or phosphine oxide compounds are selective in a vapor phase hydrogenolysis reaction to convert cyclic acetal compounds and/or cyclic ketal compounds in the presence of hydrogen to their corresponding hydroxy ether hydrocarbon reaction products.
NICKEL MODIFIED CATALYST FOR THE PRODUCTION OF HYDROXY ETHER HYDROCARBONS BY VAPOR PHASE HYDROGENOLYSIS OF CYCLIC ACETALS AND KETALS
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Page/Page column 8, (2013/02/28)
Catalyst compositions of alumina supports containing palladium and nickel are selective in a vapor phase hydrogenolysis reaction to convert cyclic acetal compounds and/or cyclic ketal compounds in the presence of hydrogen to their corresponding hydroxy ether hydrocarbon reaction products.
PRODUCTION OF HYDROXY ETHER HYDROCARBONS BY LIQUID PHASE HYDROGENOLYSIS OF CYCLIC ACETALS OR CYCLIC KETALS
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Page/Page column 7, (2013/02/28)
A liquid phase hydrogenolysis of acetal compounds such as cyclic acetals and cyclic ketals are fed to a reaction zone and reacted in the presence of a noble metal catalyst supported on a carbon or silica support to make hydroxy ether mono-hydrocarbons in high selectivity, without the necessity to use acidic co-catalysts such as phosphorus containing acids or stabilizers such as hydroquinone.
