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111-15-9

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111-15-9 Usage

Description

Ethylene glycol monoethyl ether acetate, also known as 2-Ethoxyethyl Acetate, is a colorless liquid with a mild, nonresidual odor. It belongs to the family of glycol ethers and is commonly used in various industries due to its versatile properties. It has a flash point of 120°F and is less dense than water, with vapors heavier than air. The experimentally determined detection and recognition odor threshold concentrations were 300 μg/m3 (60 ppbv) and 700 μg/m3 (130 ppbv), respectively.

Uses

Used in Coatings Industry:
Ethylene glycol monoethyl ether acetate is used as a solvent for nitrocellulose and some resins, particularly in the semiconductor industry. It is also used in coatings for brushing on, dip coating, and spraying, as well as for stove enamels.
Used in Paints, Lacquers, and Varnishes:
Ethylene glycol monoethyl ether acetate is used as a solvent to dissolve resin, leather, and ink. It is essential for the formulation of paints, lacquers, and varnishes for industrial use. Additionally, it is used to study the field evaluation of a passive badge for measuring the level of 2-ethoxyethyl acetate.
Used in Varnish Removers, Wood Stains, Textiles, and Leather:
Ethylene glycol monoethyl ether acetate serves as a solvent for nitrocellulose, oils, and resins. It is also used to retard "blushing" in lacquers, making it a valuable component in varnish removers, wood stains, textiles, and leather products.
Used in Cleaners and Paint Removers:
Another application for Ethylene glycol monoethyl ether acetate is as an additive in cleaners and paint removers, where its solvent properties help in the effective removal of dirt and paint.

Air & Water Reactions

Flammable. Slightly soluble in water.

Reactivity Profile

Mixing Ethylene glycol monoethyl ether acetate in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, oleum, and vinyl acetate, NFPA 1991.

Hazard

Toxic by ingestion and skin absorption. Toxic by skin absorption.

Health Hazard

Vapors irritate nose and eyes in high concentrations. Liquid irritates skin in prolonged or repeated contact.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. A skin and eye irritant. An experimental teratogen. Other experimental reproductive effects. Flammable liquid when exposed to heat or flame; can react with oxidizing materials. Moderate explosion hazard in the form of vapor when heated. Mild explosions have occurred at the end of disullations. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

Potential Exposure

This material is used as a solvent for many different purposes; including for nitrocellulose and other resins. Used in automobile lacquers to retard evaporation and impart a high gloss.

Environmental fate

Biological. Bridié et al. (1979) reported BOD and COD values of 0.74 and 1.76 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. The ThOD for 2-ethoxyethyl acetate is 1.82 g/g. Chemical/Physical. At an influent concentration of 1,000 mg/L, treatment with GAC resulted in an effluent concentration of 342 mg/L. The adsorbability of the carbon used was 132 mg/g carbon (Guisti et al., 1974).

Shipping

UN1172 Ethylene glycol monoethyl ether acetate, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

Shake the ethoxy-ethane with anhydrous Na2CO3, filter and distil it in a vacuum. Redistillation can then be carried out at atmospheric pressure. [Dunbar & Bolstad J Org Chem 21 1041 1956, Beilstein 2 IV 214.]

Incompatibilities

May form explosive mixture with air. Incompatible with strong acids; strong alkalies; nitrates. Violent reaction with oxidizers. May form unstable peroxides. Softens many plastics. Attacks some plastics, rubber, and coatings

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

Check Digit Verification of cas no

The CAS Registry Mumber 111-15-9 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, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 111-15:
(5*1)+(4*1)+(3*1)+(2*1)+(1*5)=19
19 % 10 = 9
So 111-15-9 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O3/c1-3-8-4-5-9-6(2)7/h3-5H2,1-2H3

111-15-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A13639)  2-Ethoxyethyl acetate, 98+%   

  • 111-15-9

  • 500ml

  • 289.0CNY

  • Detail
  • Alfa Aesar

  • (A13639)  2-Ethoxyethyl acetate, 98+%   

  • 111-15-9

  • 2500ml

  • 466.0CNY

  • Detail
  • Sigma-Aldrich

  • (01913)  2-Ethoxyethylacetate  certified reference material, TraceCERT®

  • 111-15-9

  • 01913-100MG

  • 1,075.23CNY

  • Detail

111-15-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethylene glycol monoethyl ether acetate

1.2 Other means of identification

Product number -
Other names EEA

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Flavouring Agent: FLAVOURING_AGENT
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:111-15-9 SDS

111-15-9Synthetic route

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

vinyl acetate
108-05-4

vinyl acetate

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With dilithium tetra(tert-butyl)zincate In toluene at 0℃; for 1h; Inert atmosphere;100%
1-ethoxy-2-methoxymethoxy-ethane
90325-45-4

1-ethoxy-2-methoxymethoxy-ethane

ethyl acetate
141-78-6

ethyl acetate

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With indium (III) iodide for 17h; Heating;82%
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

ethyl acetate
141-78-6

ethyl acetate

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With indium; iodine for 14h; Heating;78%
ethyl acetate
141-78-6

ethyl acetate

2-(2-ethoxy-ethoxy)-tetrahydro-pyran

2-(2-ethoxy-ethoxy)-tetrahydro-pyran

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With indium (III) iodide for 12h; Heating;78%
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

A

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

B

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

C

ethyl acetate
141-78-6

ethyl acetate

Conditions
ConditionsYield
In chlorobenzene at 140℃; for 0.5h;A 27%
B 63%
C 10%
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

A

2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

B

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

C

ethyl acetate
141-78-6

ethyl acetate

Conditions
ConditionsYield
With lead(IV) acetate In chlorobenzene at 140℃; for 0.5h; glass tube;A 27%
B 63%
C 10%
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

Ketene
463-51-4

Ketene

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With sulfuric acid
Acetyl bromide
506-96-7

Acetyl bromide

benzyl cellosolve
61911-33-9

benzyl cellosolve

A

ethyl bromide
74-96-4

ethyl bromide

B

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

C

ethylene glycol diacetate
111-55-7

ethylene glycol diacetate

D

benzyl bromide
100-39-0

benzyl bromide

Conditions
ConditionsYield
at 92℃;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

acetic anhydride
108-24-7

acetic anhydride

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

acetic acid
64-19-7

acetic acid

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid man entfernt das entstehende Wasser durch azeotrope Destillation mit Benzol;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

acetyl chloride
75-36-5

acetyl chloride

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

2-ethoxy-2-methyl-[1,3]dioxolane
13988-69-7

2-ethoxy-2-methyl-[1,3]dioxolane

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate
ethanol
64-17-5

ethanol

2-methyl-1,3-dioxolane-2-ylium tetrafluoroborate

2-methyl-1,3-dioxolane-2-ylium tetrafluoroborate

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

(Z)-1-acetoxy-2-ethoxyethylene
129751-10-6

(Z)-1-acetoxy-2-ethoxyethylene

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With hydrogen; nickel In acetone
(E)-2-Ethoxyvinylacetate
129751-09-3

(E)-2-Ethoxyvinylacetate

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With hydrogen; nickel In acetone
1,2-diacetoxy-1-ethoxy-ethane
3100-09-2

1,2-diacetoxy-1-ethoxy-ethane

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Al2O3 / 320 - 330 °C
2: H2 / Raney-Ni / acetone
View Scheme
Multi-step reaction with 2 steps
1: Al2O3 / 320 - 330 °C
2: H2 / Raney-Ni / acetone
View Scheme
Multi-step reaction with 2 steps
1: Al2O3 / 320 - 330 °C
2: H2 / Raney-Ni / acetone
View Scheme
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

sec-Butyl acetate
105-46-4

sec-Butyl acetate

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

Conditions
ConditionsYield
With tetrabutoxytitanium at 120℃; for 4h;
2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

benzyl alcohol
100-51-6

benzyl alcohol

2-ethoxyethyl 3-phenylpropanoate
22524-30-7

2-ethoxyethyl 3-phenylpropanoate

Conditions
ConditionsYield
With C15H17ClIrNOP; potassium tert-butylate In toluene at 60℃; for 12h; Schlenk technique; Inert atmosphere; Glovebox;82%
butyl ethyl ether
628-81-9

butyl ethyl ether

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

2-(1-(1H-benzo[d]imidazol-1-yl)ethoxy)ethyl acetate
117491-35-7

2-(1-(1H-benzo[d]imidazol-1-yl)ethoxy)ethyl acetate

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iron(III) chloride hexahydrate In decane; ethyl acetate at 80℃; for 3h; Inert atmosphere; Molecular sieve;73%
2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

3-(tert-butylperoxy)-3-methylindolin-2-one

3-(tert-butylperoxy)-3-methylindolin-2-one

2-(2-ethoxyethoxy)-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

2-(2-ethoxyethoxy)-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

Conditions
ConditionsYield
With tin(II) trifluoromethanesulfonate at 60℃; for 14h; Criegee Rearrangement; Sealed tube; Inert atmosphere;70%
indole
120-72-9

indole

2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

A

vibrindole A
5030-91-1

vibrindole A

B

2,2-di-(1H-indol-3-yl)ethyl acetate
88321-08-8

2,2-di-(1H-indol-3-yl)ethyl acetate

Conditions
ConditionsYield
With di-tert-butyl peroxide; iron(II) chloride at 80℃; for 1h; Inert atmosphere;A 30%
B 15%
2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

A

1,2-ethanediol acetate formate
29776-97-4

1,2-ethanediol acetate formate

B

ethylene glycol diacetate
111-55-7

ethylene glycol diacetate

C

formic acid ethyl ester
109-94-4

formic acid ethyl ester

Conditions
ConditionsYield
With methyl nitrite; nitrogen(II) oxide In gas at 25℃; Product distribution; Rate constant; Irradiation; gas-phase reaction of 2-ethoxyethyl acetate with generated hydroxy radicals; proposed reaction mechanism;
2-ethoxyethyl acetate
111-15-9

2-ethoxyethyl acetate

A

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

B

acetic acid
64-19-7

acetic acid

Conditions
ConditionsYield
With hydrogenchloride; water at 27.5 - 48.5℃; Kinetics;

111-15-9Relevant articles and documents

A process for the preparation of acetate

-

Paragraph 0054; 0055; 0056; 0057, (2017/01/26)

The invention relates to an acetate preparation method. The method comprises the following steps: carrying out a contact reaction of sec-butyl acetate and alcohol in the presence of an ester exchange catalyst under an ester exchange reaction condition, adding products obtained after the contact reaction into a separation tower, controlling the tower top temperature to separate unreacted sec-butyl acetate and sec-butyl alcohol generated after the reaction from the tower top, and carrying out normal-pressure or reduced-pressure flash evaporation to separate acetate generated after the reaction from a tower bottom fraction, wherein the alcohol is alcohol having a general formula of R(OH)n and/or polyol alkylether having at least one hydroxy group, R is a C5-C20 n-valence alkyl group, a C5-C20 n-valence alkenyl group, a C5-C12 n-valence cycloalkyl group or a C7-C20 n-valence aryl group, and n is an integer in a range of 1-5. The method has the advantages of high conversion rate of the alcohol as a reaction raw material, and high acetate selectivity.

Highly selective one-pot conversion of THP and MOM ethers to acetates by indium triiodide-catalysed deprotection and subsequent transesterification by ethyl acetate

Ranu, Brindaban C.,Hajra, Alakananda

, p. 2262 - 2265 (2007/10/03)

The chemoselective one-pot conversion of tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers of primary alcohols to the corresponding acetates was presented. It was done using indium triiodide-catalysed deprotection and subsequent acetylation by ethyl acetate through a transesterification process. The advantages offered by the method included operational simplicity, 'green' methodology involving no toxic or hazardous chemicals and high yield.

Highly selective acylation of alcohols and amines by an indium triiodide-catalysed transesterification process

Ranu, Brindaban C.,Dutta, Pinak,Sarkar, Arunkanti

, p. 2223 - 2225 (2007/10/03)

A very simple method has been developed for the acylation of alcohols and amines by ethyl acetate through an indium triiodide-catalysed transesterification process. Using this method acylation of a primary OH group in the presence of secondary and phenolic OH groups, and of a primary NH2 in the presence of secondary NH and primary OH have been achieved with high selectivity. The Royal Society of Chemistry 2000.

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