111-55-7

Basic information

• Product Name: Ethylene glycol diacetate
• Synonyms: 2-(Acetyloxy)ethyl acetate;Aceticacid2-acetoxy-ethylester;CH3C(O)OCH2CH2OC(O)CH3;diacetated’ethyleneglycol;Ethylene diacetin;Ethylene glycol acetate;Ethylene gycol diacetate;ethylenediethanoate
• CAS NO: 111-55-7
• Molecular Formula: C₆H₁₀O₄
• Molecular Weight: 146.14
• EINECS: 203-881-1
• Product Categories: Organics
• Mol File: 111-55-7.mol

Chemical Properties

• Melting Point: -41 °C
• Boiling Point: 196-198 °C(lit.)
• Flash Point: 198 °F
• Appearance: blue/Liquid
• Density: 1.128 g/mL at 25 °C(lit.)
• Vapor Density: 5.04 (vs air)
• Vapor Pressure: 0.2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: 2-8°C
• Solubility: 160g/l
• Explosive Limit: 1.6%, 135°F
• Water Solubility: 160 g/L (20 ºC)
• Merck: 14,3799
• BRN: 1762308
• CAS DataBase Reference: Ethylene glycol diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylene glycol diacetate(111-55-7)
• EPA Substance Registry System: Ethylene glycol diacetate(111-55-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25-22
• WGK Germany: 1
• RTECS: KW4025000
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 111-55-7(Hazardous Substances Data)

Usage

Uses

Used in Solvent Applications:
Ethylene glycol diacetate is used as a solvent for various substances, including oils, cellulose esters, and explosives. It is effective in dissolving these materials, making it a versatile solvent in different industries.
Used in Baking Lacquers and Enamels:
Ethylene glycol diacetate is used as a flow property enhancer in baking lacquers and enamels. It helps improve the application and performance of these coatings, providing a smooth and even finish.
Used in Thermoplastic Acrylic Resins:
EGDA is used in conjunction with thermoplastic acrylic resins, where it imparts excellent flow properties. This makes it suitable for use in various applications requiring thermoplastic materials.
Used in Cellulosic Coatings:
Ethylene glycol diacetate is a good solvent for cellulosic coatings, making it a valuable component in the formulation of these types of coatings.
Used in Ink Systems:
EGDA can be used in some ink systems, such as screen inks, where its solvent properties are beneficial for the ink's performance and application.
Used in Perfume Fixative:
Ethylene glycol diacetate is used as a perfume fixative, helping to stabilize and prolong the scent of perfumes.
Used in Waterborne Adhesives:
EGDA has reported applications in waterborne adhesives, where it contributes to the adhesive's performance and properties.
Used in the Chemoenzymatic Synthesis of Caprolactone:
Ethylene glycol diacetate may be used as an acyl donor for the in situ generation of peracetic acid during the chemoenzymatic synthesis of caprolactone. This application highlights its versatility in chemical reactions and synthesis processes.
Used in the Enzymatic Synthesis of Poly (Ethylene Glutarate):
EGDA can be employed as a precursor for the enzymatic synthesis of poly (ethylene glutarate), showcasing its potential in polymer synthesis and material development.

Air & Water Reactions

Water soluble.

Reactivity Profile

Ethylene glycol diacetate reacts with aqueous acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction with caustic solutions. Flammable hydrogen is generated with alkali metals and hydrides.

Health Hazard

Inhalation is not hazardous. Liquid causes mild irritation of eyes. Ingestion causes stupor or coma.

Fire Hazard

Ethylene glycol diacetate is combustible.

Flammability and Explosibility

Notclassified

Safety Profile

Moderately toxic by intraperitoneal route. Mildly toxic by ingestion and skin contact. An eye irritant. Combustible when exposed to heat or flame; can react with oxidzing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Dry the di-ester with CaCl2, filter (excluding moisture) and fractionally distil it under reduced pressure. [Beilstein 2 IV 1541.]

InChI:InChI=1/C6H10O4/c1-4(7)9-6(3)10-5(2)8/h6H,1-3H3

Synthetic route

ethylene glycol (107-21-1) + acetic acid (64-19-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
zirconium(IV) oxide at 180℃; for 2h; in autoclave;	100%
With 1-(3-sulfonic acid)propylimidazole bisulfate ([Ps-im]HSO4) supported silica In cyclohexane at 150℃; under 760.051 Torr; for 5h; Pressure; Temperature; Time;	99.61%
With sulfonated charcoal In benzene for 5h; Heating;	95%

acetic anhydride (108-24-7) + ethylene glycol (107-21-1) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With H-Y zeolite at 60℃; for 2h;	100%
With sodium hydroxide for 0.0194444h; microwave irradiation;	99%
With SiO2-supported Co(II) Salen complex catalyst at 50℃; for 0.833333h;	99%

acetic acid methyl ester (79-20-9) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With carbon monoxide; hydrogen; acetic acid; methyl iodide at 176℃; under 15001.5 - 61506.2 Torr; for 7.5h; Reagent/catalyst; Autoclave; Inert atmosphere;
With carbon monoxide; hydrogen; acetic acid; methyl iodide at 176℃; under 15001.5 - 54005.4 Torr; for 8h; Reagent/catalyst; Autoclave; Inert atmosphere;
With carbon monoxide; hydrogen; acetic acid; methyl iodide at 175℃; under 1500.15 - 54755.5 Torr; for 8h; Reagent/catalyst; Autoclave; Inert atmosphere;

acetic acid methyl ester (79-20-9) + acetic acid (64-19-7) + methyl iodide (74-88-4) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With carbon monoxide; hydrogen at 173℃; under 51005.1 Torr; for 8h; Temperature; Pressure; Inert atmosphere; Autoclave; Industrial scale;
With carbon monoxide; hydrogen at 177℃; under 56255.6 Torr; for 7.5h; Temperature; Pressure; Inert atmosphere; Autoclave; Industrial scale;

Tetraethylene glycol (112-60-7) + acetic acid (64-19-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With H+-mont In neat (no solvent) at 160℃; for 2h; Reagent/catalyst; Time;	89 %Chromat.

sodium acetate (127-09-3) + 1,2-dichloro-ethane (107-06-2) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
tetrabutyl phosphonium bromide at 150℃; under 20 Torr; g.l.p.t.c.;	55%
With iron(II) sulfate at 200 - 240℃;
With pyridine at 175℃; auch in Gegenwart von aliphatischen Aminen;

1-ethyl-3-methylimidazolium acetate (143314-17-4) + 1,2-dichloro-ethane (107-06-2) → ethylene glycol diacetate (111-55-7) + 1-ethyl-3-methyl-1H-imidazol-3-ium chloride (65039-09-0)

Conditions	Yield
at 70℃; for 3h; Inert atmosphere;	A 90% B n/a

1-ethyl-3-methylimidazolium acetate (143314-17-4) + ethylene dibromide (106-93-4) → ethylene glycol diacetate (111-55-7) + 3-ethyl-1-methyl-1H-imidazol-3-ium bromide (65039-08-9)

Conditions	Yield
at 20℃; for 3h; Inert atmosphere;	A 90% B n/a

acetic acid methyl ester (79-20-9) + carbon monoxide (201230-82-2) + acetic acid (64-19-7) + methyl iodide (74-88-4) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With hydrogen at 200℃; under 15001.5 - 75007.5 Torr; for 10h; Temperature; Reagent/catalyst; Pressure; Autoclave;

carbon monoxide (201230-82-2) + tetra-n-butylphosphonium acetate (30345-49-4) → acetic acid methyl ester (79-20-9) + 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7) + ethylene glycol (107-21-1)

Conditions	Yield
With hydrogen; ruthenium(IV) oxide at 220℃; under 326800 Torr; Yield given. Further byproducts given. Yields of byproduct given;

ethylene glycol (107-21-1) + ethyl acetate (141-78-6) → 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
sodium hydrogen sulfate In hexane at 50℃; for 5h;	A 78% B 3%
sodium hydrogen sulfate; silica gel In hexane at 50℃; for 5h;	A 78 % Chromat. B 3 % Chromat.

1,4-dioxane (123-91-1) + acetic anhydride (108-24-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With aminosulfonic acid In acetic acid at 60℃; for 4h;	86%

ethylene glycol (107-21-1) + acetyl chloride (75-36-5) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With zinc(II) oxide at 20℃; for 0.133333h;	91%
With ZnAl2O4 nanoparticles at 20℃; for 0.466667h; Neat (no solvent);	90%
With pyridine In diethyl ether	63%

Isopropenyl acetate (108-22-5) + ethylene glycol (107-21-1) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With iodine at 85 - 90℃; for 0.166667h;	91%
With sulfuric acid

carbon monoxide (201230-82-2) + acetic acid (64-19-7) → acetic acid methyl ester (79-20-9) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium; hydrogen at 260℃; under 258400 Torr; for 2h;	A 139 mmol B 1.58 mmol

2-methylene-1,3-dioxolane (4362-23-6) + acetic acid (64-19-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
In tetrahydrofuran at 20℃; for 4h; Acetylation;	87.3%

ethane (74-84-0) + thallium(III) acetate (2570-63-0) + acetic acid (64-19-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
at 180℃; under 26618.1 Torr; for 3h;	43 %Spectr.

ethene (74-85-1) → 1,2-Diiodoethane (624-73-7) + 2-iodoethyl acetate (627-10-1) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
With iodine In acetic acid at 140℃; under 14710.2 Torr; for 1.5h; Yield given. Yields of byproduct given;

Tetraethylene glycol dimethyl ether (143-24-8) + acetic anhydride (108-24-7) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With zinc(II) triflate at 130℃; for 24h; Reagent/catalyst;	88%

Trimethyl orthoacetate (1445-45-0) + ethylene glycol (107-21-1) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 4h;

carbon monoxide (201230-82-2) + acetic acid (64-19-7) → acetic acid methyl ester (79-20-9) + 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7) + ethyl acetate (141-78-6)

Conditions	Yield
With caesium(1+); hydrogen; acetylacetonatodicarbonylrhodium(l); ruthenium acetylacetonate at 230℃; under 760000 Torr; Yield given. Further byproducts given. Yields of byproduct given;

ethene (74-85-1) + acetic acid (64-19-7) → vinyl acetate (108-05-4) + 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
With Pd(MeCN)2Cl(NO2) at 25℃; under 2068.6 Torr; for 4h; Product distribution; various catalysts, times, additives, O2 atmosphere, with 18O containing complex;	A 20% B 50% C 7%

ethene (74-85-1) + acetic acid (64-19-7) → 1,2-Diiodoethane (624-73-7) + 2-iodoethyl acetate (627-10-1) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
With iodine at 140℃; under 14710.2 Torr; for 1.5h; Yield given. Yields of byproduct given;

ethylene glycol (107-21-1) + acetic acid (64-19-7) → 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
at 130℃; for 3h; Product distribution / selectivity;	A 44% B n/a
With Ag(1+)*2H(1+)*PW12O40(3-)=AgH2PW12O40 at 120℃; for 0.25h; Autoclave; Green chemistry;

acetic anhydride (108-24-7) + poly(ethylene glycol) → ethylene glycol diacetate (111-55-7)

Conditions	Yield
With zinc(II) triflate at 150℃; for 24h; Reagent/catalyst; Temperature;	19%

ethylene glycol (107-21-1) + acetyl chloride (75-36-5) → 2-hydroxyethyl acetate (542-59-6) + ethylene glycol diacetate (111-55-7)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 25℃; for 24h;

tolazoline hydrochloride (59-97-2) + acetic acid (64-19-7) → phenylacetic acid (103-82-2) + ethylene glycol diacetate (111-55-7) + N-nitroso-2-imidazolinyl phenyl ketoxime + 2-hydroxyethyl 2-phenylacetate (28481-53-0)

Conditions	Yield
With sodium nitrite at 25℃; for 1h; Further byproducts.;	A 30% B 9% C 19% D 9%

ethylene glycol diacetate (111-55-7) + saccharin (81-07-2) → 2-(2-acetoxy-ethyl)-1,1-dioxo-1,2-dihydro-1λ6-benzo[d]isothiazol-3-one (23302-99-0)

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate at 120℃; for 14h; Sealed tube;	100%

ethylene glycol diacetate (111-55-7) + N-methyl-p-toluenesulfonylamide (640-61-9) → 1-acetoxy-2-[methyl-(toluene-4-sulfonyl)-amino]-ethane (59724-91-3)

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate at 120℃; for 14h; Reagent/catalyst; Temperature;	95%

ethylene glycol diacetate (111-55-7) + 4-bromo-N-methylbenzenesulphonamide (703-12-8) → C11H14BrNO4S

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate at 120℃; for 14h; Sealed tube;	93%

N-methylmethane sulphonamide (1184-85-6) + ethylene glycol diacetate (111-55-7) → C6H13NO4S

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate at 120℃; for 14h; Sealed tube;	92%

ethylene glycol diacetate (111-55-7) + aniline (62-53-3) → N-ethyl-N-phenylamine (103-69-5) + N,N-diethylaniline (91-66-7)

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; under 45004.5 Torr; for 18h; Kinetics; Temperature; Autoclave;	A 12% B 86%
With tris(2,4-pentanedionato)ruthenium(III); hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 130℃; under 45004.5 Torr; for 18h; Kinetics;	A 83% B 9%

ethylene glycol diacetate (111-55-7) + toluene-4-sulfonamide (70-55-3) → C10H13NO4S

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate at 120℃; for 14h; Sealed tube;	85%

ethylene glycol diacetate (111-55-7) + N,N-dimethylammonium chloride (506-59-2) + formic acid ethyl ester (109-94-4) → ethyleneglycoldi(3-N,N-dimethylaminopropyl)acrylate

Conditions	Yield
Stage #1: ethylene glycol diacetate; formic acid ethyl ester With sodium t-butanolate In toluene at 20℃; Stage #2: N,N-dimethylammonium chloride In toluene for 2h;	84%
Stage #1: ethylene glycol diacetate; formic acid ethyl ester With sodium t-butanolate In toluene at 20℃; Stage #2: N,N-dimethylammonium chloride In toluene for 2h;	84%

ethylene glycol diacetate (111-55-7) + 4-Ethoxyaniline (156-43-4) → 4-ethoxyacetanilide (62-44-2)

Conditions	Yield
sodium methylate In ethylene glycol at 120 - 125℃; for 3h; Conversion of starting material;	75%

piperidine (110-89-4) + ethylene glycol diacetate (111-55-7) + formic acid ethyl ester (109-94-4) → ethylene glycol bis(3-(N-piperidyl)acrylate)

Conditions	Yield
Stage #1: ethylene glycol diacetate; formic acid ethyl ester With sodium t-butanolate In toluene at 20℃; Stage #2: piperidine In toluene for 2h;	74.7%
Stage #1: ethylene glycol diacetate; formic acid ethyl ester With sodium t-butanolate In toluene at 20℃; Stage #2: piperidine In toluene for 2h;	74.7%

ethylene glycol diacetate (111-55-7) + diethylamine (109-89-7) + formic acid ethyl ester (109-94-4) → ethylene glycol bis(3-(N,N-diethylamino)acrylate)

Conditions	Yield
Stage #1: ethylene glycol diacetate; formic acid ethyl ester With sodium t-butanolate In toluene at 20℃; Stage #2: diethylamine In toluene for 2h;	70.6%
Stage #1: ethylene glycol diacetate; formic acid ethyl ester With sodium t-butanolate In toluene at 20℃; Stage #2: diethylamine In toluene for 2h;	70.6%

(Z)-3-Hexen-1-ol (928-96-1) + ethylene glycol diacetate (111-55-7) → (Z)-3-Hexenyl acetate (3681-71-8)

Conditions	Yield
With Candida antarctica lipase B immobilized on a macroporous acrylic resin at 40℃; for 19h; Temperature; Green chemistry; Enzymatic reaction;	70%

ethylene glycol diacetate (111-55-7) → vinyl acetate (108-05-4)

Conditions	Yield
With acetic anhydride; benzenesulfonic acid at 140℃; under 1875.19 Torr; for 0.75h; Inert atmosphere;	65.05%
With acetic anhydride; benzenesulfonic acid at 142℃; under 3000.3 Torr; for 0.75h; Inert atmosphere;	64.47%
With acetic anhydride; benzenesulfonic acid at 143℃; under 3000.3 Torr; for 0.666667h; Inert atmosphere;	64.57%

Upstream product

• 75-21-8 oxirane 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 123-91-1 1,4-dioxane 
• 75-36-5 acetyl chloride 
• 506-96-7 Acetyl bromide 
• 61911-33-9 benzyl cellosolve 
• 624-73-7 1,2-Diiodoethane 
• 563-63-3 silver(I) acetate 
• 107-21-1 ethylene glycol 
• 463-51-4 Ketene 
• 108-05-4 vinyl acetate 
• 108-22-5 Isopropenyl acetate 
• 542-59-6 2-hydroxyethyl acetate 

Downstream Products

• 79-20-9 acetic acid methyl ester 
• 542-59-6 2-hydroxyethyl acetate 
• 107-21-1 ethylene glycol 
• 64-19-7 acetic acid 
• 141-78-6 ethyl acetate 
• 108-05-4 vinyl acetate 
• 542-58-5 2-chloro-1-acetoxyethane 
• 38353-69-4 2-(acetyloxy)ethyl benzoate 
• 105-46-4 sec-Butyl acetate 
• 793-06-6 4,4'-diacetylbibenzyl 
• 542-10-9 ethylidene diacetate 
• 108-24-7 acetic anhydride 
• 75-07-0 acetaldehyde 
• 67-64-1 acetone 

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the acidity is solidcarries ionic liquid catalyst for synthesizing ethylene glycol acetate method

The invention discloses a method for synthesizing glycol diacetate under the catalytic action of an acidic immobilized ionic liquid. Under the catalytic action of an acidic immobilized ionic liquid, ethylene glycol and acetic acid used as raw materials are directly esterified to synthesize the glycol diacetate in a batch rectification tower, wherein the acidic immobilized ionic liquid is an acidic ionic liquid immobilized on the surface or in the pores of a support. The method has the advantages of high reaction selectivity, mild conditions, high raw material conversion rate and the like, and the catalyst can be easily separated from the reaction system and is recyclable. The glycol diacetate yield of the method can reach 99.4%, and the reaction selectivity can reach 99.5% above.

Method for synthesizing vinyl acetate

The invention relates to a method for synthesizing vinyl acetate. When vinyl acetate is prepared from methyl acetate through the route of carbonylation and cracking, vinyl acetate yield and selectivity are low. The invention mainly aims at solving the problems. The vinyl acetate synthesis method comprises the following steps: methyl acetate carbonylation is carried out, such that ethylene diacetate is obtained; and ethylene diacetate is cracked, such that vinyl acetate is obtained. A carbonylation catalyst adopts SiO2, Al2O3 or a mixture thereof as a carrier, and has active components comprising at least one selected from iron-series elements, alkaline earth metal and at least one metal element selected from IB and VA. With the technical scheme, the technical problem is well solved. The method can be used in industrial production of vinyl acetate.

Synthetic method for vinyl acetate

The invention relates to a synthetic method for vinyl acetate and is mainly to solve the problems of low yield and selectivity of vinyl acetate in preparation for vinyl acetate from methyl acetate successively through carbonylation and cracking routes. According to a technical scheme of the invention, the synthetic method for vinyl acetate comprises the following steps: subjecting methyl acetate to carbonylation so as to obtain ethylidene diacetate, and subjecting ethylidene diacetate to cracking so as to obtain vinyl acetate, wherein a carbonylation catalyst uses SiO2, Al2O3 or a mixture of SiO2 and Al2O3 as a carrier; an active component is at least one selected from the group consisting of platinum-cluster metals, at least one selected from the group consisting of group-VIB metals, and at least one selected from the group consisting of group-IB metals and lanthanide series metals; thus, the above-mentioned technical problems are well solved, and the synthetic method can be applied in industrial production of vinyl acetate.

Production method of vinyl acetate

The invention relates to a production method of vinyl acetate and mainly solves the problems of low yield and low selectivity of the vinyl acetate when methyl acetate is successively subjected to carbonylation and pyrolysis to prepare the vinyl acetate. The production method includes the following steps: 1) carbonylating the methyl acetate to obtain ethylidene diacetate; and 2) pyrolyzing the ethylidene diacetate to obtain the vinyl acetate. A carbonylation catalyst includes a carrier being formed from SiO2, Al2O3 or a mixture of them, and an active component including at least one of platinum-series elements, at least one element from metalloid elements, and at least one metal element from the groups of IIB and lanthanide-series metals. The method solves the technical problems well and can be used in industrial production of the vinyl acetate.