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629-14-1

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629-14-1 Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 629-14-1 differently. You can refer to the following data:
1. Clear colorless liquid
2. Ethylene glycol diethyl ether is a colorless liquid.

Uses

Ethylene glycol diethyl ether is a important solvent, used for ink, paint and coating industry. Mainly used in polymer, electrochemistry, boracium chemistry, resin, nitro cellulose, In this product , the benzene, xenene, terphenyl, anthracene reacts with sodium and then bring about the complex; it is also used in surface treatment, halogen analysis in gasoline, acetic acid recycle in diluted acetic acid, depaint agent, thinner, flushing agent, stabilizer, anti oxidant , thickener of lube.

General Description

A clear colorless liquid with a faint ether-like odor. Flash point 95°F. Less dense than water and insoluble in water. Vapors heavier than air.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Ethylene glycol diethyl ether can react with oxidizers. Ethylene glycol diethyl ether is incompatible with strong acids.

Health Hazard

Inhalation causes irritation of nose and throat. Contact with liquid irritates eyes but has little or no effect on skin. Ingestion causes irritation of mouth and stomach.

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. Mildly toxic by inhalation. An experimental teratogen. Experimental reproductive effects. An eye irritant. An aprotic solvent. A very dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. To fight fire, use CO2, dry chemical. See also GLYCOL ETHERS and various cellosolve entries.

Potential Exposure

Ethylene glycol diethyl ether is used as an aprotic solvent; in chemical manufacturing; as a solvent for detergents and in other cleaning products

Shipping

UN1153 Ethylene glycol diethyl ether, Hazard Class: 3; Labels: 3-Flammable liquid

Purification Methods

After refluxing for 12hours, a mixture of the ether (2L), conc HCl (27mL) and water (200mL), is added with slow passage of nitrogen. The solution is cooled, and KOH pellets are added slowly and with shaking until no more dissolves. The organic layer is decanted, treated with some KOH pellets and again decanted. It is then refluxed with, and distilled from sodium immediately before use. Alternatively, after removal of peroxides by treatment with activated alumina, the ether is refluxed in the presence of the blue ketyl formed by sodium-potassium alloy with benzophenone, then distilled. [Beilstein 1 H 468, 1 II 519, 1 III 2078, 1 IV 2379.]

Incompatibilities

Forms explosive mixture with air when heated. Incompatible with oxidizers (chlorates, nitrates,peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, and epoxides. Attacks some plastics, rubber and coatings. May slowly form unstable reactive peroxides during prolonged storage or on exposure to air and light. Also incompatible with strong acids; aluminum and its alloys

Check Digit Verification of cas no

The CAS Registry Mumber 629-14-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 9 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 629-14:
(5*6)+(4*2)+(3*9)+(2*1)+(1*4)=71
71 % 10 = 1
So 629-14-1 is a valid CAS Registry Number.

629-14-1 Well-known Company Product Price

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

  • (L14283)  1,2-Diethoxyethane, 98%   

  • 629-14-1

  • 100ml

  • 492.0CNY

  • Detail
  • Alfa Aesar

  • (L14283)  1,2-Diethoxyethane, 98%   

  • 629-14-1

  • 500ml

  • 1636.0CNY

  • Detail
  • Sigma-Aldrich

  • (224111)  Ethyleneglycoldiethylether  98%

  • 629-14-1

  • 224111-100ML

  • 776.88CNY

  • Detail
  • Sigma-Aldrich

  • (224111)  Ethyleneglycoldiethylether  98%

  • 629-14-1

  • 224111-500ML

  • 2,424.24CNY

  • Detail

629-14-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethylene glycol diethyl ether

1.2 Other means of identification

Product number -
Other names 1,2-diethoxyethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:629-14-1 SDS

629-14-1Synthetic route

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

ethene
74-85-1

ethene

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With sulfuric acid at 40 - 70℃; under 3000.3 Torr; for 3h; Autoclave; Inert atmosphere;74.6%
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With sulfuric acid
With H-type ZSM-5(SiO2/Al2O3=280) at 180℃; for 3h;
With sulfuric acid
1-ethoxy-2-vinyloxy-ethane
18861-14-8

1-ethoxy-2-vinyloxy-ethane

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With nickel Hydrogenation.von gasfoermigem oder in Alkoholen geloestem;
With nickel Hydrogenation.von gasfoermigem oder in Alkoholen geloestem;
2-chloroethyl ethyl ether
628-34-2

2-chloroethyl ethyl ether

sodium ethanolate
141-52-6

sodium ethanolate

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With ethanol
1-ethoxy-2-trityloxy-ethane
4673-60-3

1-ethoxy-2-trityloxy-ethane

A

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

B

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

C

triphenylmethane
519-73-3

triphenylmethane

D

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
at 325 - 330℃;
ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With copper
With tetrahydrofuran; magnesium
With tetrahydrofuran; sodium
With diethyl ether; sodium
Diazoethan
1117-96-0

Diazoethan

ethylene glycol
107-21-1

ethylene glycol

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

ethoxymethylmagnesium chloride
4279-03-2

ethoxymethylmagnesium chloride

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With benzyl bromide In tetrahydrofuran at -30℃;
2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

A

ethanol
64-17-5

ethanol

B

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

C

acetaldehyde
75-07-0

acetaldehyde

D

ethyl acetate
141-78-6

ethyl acetate

Conditions
ConditionsYield
With hydrogen; Ni-Cab-O-Sil at 300℃; Yield given. Yields of byproduct given;
2-methyl-1,3-dioxolane
497-26-7

2-methyl-1,3-dioxolane

A

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

B

ethanol
64-17-5

ethanol

C

ethane
74-84-0

ethane

D

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

E

acetic acid
64-19-7

acetic acid

F

ethyl acetate
141-78-6

ethyl acetate

Conditions
ConditionsYield
With hydrogen; Pt-Cab-O-Sil at 300℃; Product distribution; Mechanism; var. of catalyst, temp.;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

1-butyl-1-nitrosourea
869-01-2

1-butyl-1-nitrosourea

A

2-Butoxyethanol
111-76-2

2-Butoxyethanol

B

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

C

1-(2-Ethoxyethoxy)butan
4413-13-2

1-(2-Ethoxyethoxy)butan

D

ethylene glycol sec-butyl ethyl ether
77078-19-4

ethylene glycol sec-butyl ethyl ether

Conditions
ConditionsYield
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.
(E/Z)-1,2-dibromo-1,2-difluoroethylene
359-21-7

(E/Z)-1,2-dibromo-1,2-difluoroethylene

sodium 2-ethoxyethoxide
16993-83-2

sodium 2-ethoxyethoxide

A

3,6,9-trioxaundecane
112-36-7

3,6,9-trioxaundecane

B

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

C

(E)-1,2-Dibromo-1-(2-ethoxy-ethoxy)-2-fluoro-ethene

(E)-1,2-Dibromo-1-(2-ethoxy-ethoxy)-2-fluoro-ethene

D

2-ethoxyethyl bromofluoroacetate

2-ethoxyethyl bromofluoroacetate

E

(E)-1-Bromo-2-(2-ethoxy-ethoxy)-1,2-difluoro-ethene

(E)-1-Bromo-2-(2-ethoxy-ethoxy)-1,2-difluoro-ethene

F

(Z)-1-Bromo-2-(2-ethoxy-ethoxy)-1,2-difluoro-ethene

(Z)-1-Bromo-2-(2-ethoxy-ethoxy)-1,2-difluoro-ethene

Conditions
ConditionsYield
In 2-ethoxy-ethanol at 30 - 40℃; Product distribution;
O,O'-diethyl dithiooxalate
54129-84-9

O,O'-diethyl dithiooxalate

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With nickel In diethyl ether 1.) -15 deg C, 2.) -10 deg C, 2 min;23 % Chromat.
tetrahydrofuran
109-99-9

tetrahydrofuran

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

magnesium

magnesium

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

tetrahydrofuran
109-99-9

tetrahydrofuran

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

sodium

sodium

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

chloroethane
75-00-3

chloroethane

sodium compound of ethylene glycol-monoethyl ether

sodium compound of ethylene glycol-monoethyl ether

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

1,1-bis-(2-ethoxy-ethoxy)-ethane
39114-77-7

1,1-bis-(2-ethoxy-ethoxy)-ethane

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: platinized asbestos / 260 °C
2: nickel / Hydrogenation.von gasfoermigem oder in Alkoholen geloestem
View Scheme
3,6,9-trioxaundecane
112-36-7

3,6,9-trioxaundecane

A

1,4-dioxane
123-91-1

1,4-dioxane

B

diethyl ether
60-29-7

diethyl ether

C

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With Cp*Si(1+)* B(C6F5)4(1-) In dichloromethane-d2 at -30℃; for 144h; Inert atmosphere;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

ethanol
64-17-5

ethanol

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With MCM-22 zeolite at 50℃; under 750.075 Torr; Reagent/catalyst; Pressure; Temperature;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

diethyl ether
60-29-7

diethyl ether

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With MCM-22 In 1,4-dioxane at 90℃; under 6750.68 Torr; Reagent/catalyst; Temperature; Pressure; Inert atmosphere;
With hydrogen-type Beta molecular sieve at 220℃; under 22502.3 Torr; Temperature; Pressure; Reagent/catalyst; Autoclave;
ethanol
64-17-5

ethanol

ethylene glycol
107-21-1

ethylene glycol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

C

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With HY zeolite In water at 209.84℃; under 2250.23 Torr; for 4h; Catalytic behavior; Time; Flow reactor; Inert atmosphere; Green chemistry;
2-ethoxy-ethanol
110-80-5

2-ethoxy-ethanol

diethyl ether
60-29-7

diethyl ether

A

1,4-dioxane
123-91-1

1,4-dioxane

B

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

Conditions
ConditionsYield
With sulfonated styrene-divinylbenzene copolymer acidic cation exchange resin (D005) at 140℃; under 45004.5 Torr; Reagent/catalyst; Autoclave;
tantalum pentafluoride

tantalum pentafluoride

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

[TaF4(κ2-1,2-diethoxyethane)2][Ta2F11]
1203465-01-3

[TaF4(κ2-1,2-diethoxyethane)2][Ta2F11]

Conditions
ConditionsYield
In dichloromethane a suspn. of TaF5 treated with ligand, stirred at room temp.; filtered, evapd. (vac.), crystd. from CH2Cl2/heptane at room temp.; elem. anal.;78%
benzoxazole
273-53-0

benzoxazole

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

2-(1-(2-ethoxyethoxy)ethyl)benzo[d]oxazole

2-(1-(2-ethoxyethoxy)ethyl)benzo[d]oxazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; cobalt(II) carbonate In decane at 120℃; for 14h; Sealed tube; regioselective reaction;78%
With tert.-butylhydroperoxide In decane at 100℃; for 24h; Inert atmosphere;61%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

niobium pentachloride
10026-12-7

niobium pentachloride

NbCl4O(CH2CH3)CH2CH2O
1107601-61-5

NbCl4O(CH2CH3)CH2CH2O

Conditions
ConditionsYield
In dichloromethane (under Ar, Schlenk); suspn. of NbCl5 in CH2Cl2 treated with 1,2-diethoxyethane, stirred at room temp. for 30 min; filtered, layered with pentane, 12 h at -20°C; elem. anal.;77%
niobium pentafluoride

niobium pentafluoride

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

[NbF4(κ2-1,2-diethoxyethane)2][NbF6]
1203464-93-0

[NbF4(κ2-1,2-diethoxyethane)2][NbF6]

Conditions
ConditionsYield
In dichloromethane a suspn. of NbF5 treated with ligand, stirred at room temp.; evapd. (vac.), crystd. from CH2Cl2/pentane at room temp.; elem. anal.;77%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

niobium pentabromide
13478-45-0

niobium pentabromide

NbBr4[OCH2CH2OEt]
1310341-75-3

NbBr4[OCH2CH2OEt]

Conditions
ConditionsYield
In dichloromethane byproducts: CH3CH2Br; (Ar); addn. of dme to a suspn. of Nb compd. in CH2Cl2, stirring for 1 h at room temp.; pptn. by addn. of pentane; elem. anal.;77%
In chloroform-d1 byproducts: CH3CH2Br; (Ar); react. dme and Nb compd. in CDCl3; detected by NMR;
i-Amyl alcohol
123-51-3

i-Amyl alcohol

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

6-n-decyloxynaphthalene-2-carboxylic acid
122527-97-3

6-n-decyloxynaphthalene-2-carboxylic acid

1,2,3,4-tetrahydro-6-n-decyloxynaphthalene-2-carboxylic acid
137270-01-0

1,2,3,4-tetrahydro-6-n-decyloxynaphthalene-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water75%
In ethanol; water
In ethanol; water
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(Z)-1,2-bis(phenylsulfonyl)ethene
963-15-5

(Z)-1,2-bis(phenylsulfonyl)ethene

A

C14H20O4S

C14H20O4S

B

C14H20O4S

C14H20O4S

Conditions
ConditionsYield
With Benzoylformic acid at 20℃; Sealed tube; Irradiation; diastereoselective reaction;A 75%
B 21%
5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate rhodium(II)
121393-39-3

5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate rhodium(II)

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate)rhodium(III) methyl

(5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate)rhodium(III) methyl

Conditions
ConditionsYield
With PPh3; KOH; Ph4PBr In further solvent(s) under N2; in the dark; Rh compd. reacted with (MeCH2OCH2)2 in presence of PPh3 (1 equiv.), KOH (10 equiv.), H2O (50 equiv.) and Ph4PBr (0.1 equiv.) at 25°C for 10 min;74%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

tri-n-butyl(vinyl)tin
7486-35-3

tri-n-butyl(vinyl)tin

7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol
544704-73-6

7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol

prinaberel
524684-52-4

prinaberel

Conditions
ConditionsYield
trans-dichlorobis(tri-o-tolyl-phosphine)palladium(II)72%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

molybdenum(V) chloride
10241-05-1

molybdenum(V) chloride

MoCl4[κ2-ROCH2CH2OEt]

MoCl4[κ2-ROCH2CH2OEt]

Conditions
ConditionsYield
In dichloromethane at 20℃; Inert atmosphere;72%
niobium(V) iodide
13779-92-5

niobium(V) iodide

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

[NbI4(κ1-OCH2CH2OEt))2
1310341-78-6

[NbI4(κ1-OCH2CH2OEt))2

Conditions
ConditionsYield
In dichloromethane byproducts: CH3CH2I; (Ar); addn. of dme to a suspn. of Nb compd. in CH2Cl2, stirring for 120 h at room temp.; pptn. by addn. of pentane; elem. anal.;61%
In chloroform-d1 byproducts: CH3CH2I; (Ar); react. dme and Nb compd. in CDCl3; detected by NMR;
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(5-fluoro-2-isocyanophenyl)(methyl)sulfane

(5-fluoro-2-isocyanophenyl)(methyl)sulfane

2-(1-(2-ethoxyethoxy)ethyl)-6-fluorobenzo[d]thiazole

2-(1-(2-ethoxyethoxy)ethyl)-6-fluorobenzo[d]thiazole

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; Green chemistry;60%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

tetramethyl titanium
2371-70-2

tetramethyl titanium

(CH3)4Ti(C2H5OC2H4OC2H5)

(CH3)4Ti(C2H5OC2H4OC2H5)

Conditions
ConditionsYield
In diethyl ether addn. of precooled 1,2-diethoxyethane to a soln. of Me4Ti in Et2O at -30°C; evapn. of solvent in vac. at -30°C;; dissolving residue in cold pentane, filtering; cooling to -78°C; crystn. after several days; decanting, drying at -30°C in vac.;;59.4%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(η6-indenyl-1,3-(SiMe3)2)(η5-indenyl-1,3-(SiMe3)2)Zr
573982-92-0, 831174-19-7

(η6-indenyl-1,3-(SiMe3)2)(η5-indenyl-1,3-(SiMe3)2)Zr

(η6-indenyl-1,3-(SiMe3)2)(η5-indenyl-1,3-(SiMe3)2)Zr(1,2-diethoxyethane)
863313-34-2

(η6-indenyl-1,3-(SiMe3)2)(η5-indenyl-1,3-(SiMe3)2)Zr(1,2-diethoxyethane)

Conditions
ConditionsYield
In pentane ligand added to Zr complex in pentane at 23°C; NMR;58%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(2-isocyanophenyl)(methyl)sulfane
175694-99-2

(2-isocyanophenyl)(methyl)sulfane

2-(1-(2-ethoxyethoxy)ethyl)benzo[d]thiazole

2-(1-(2-ethoxyethoxy)ethyl)benzo[d]thiazole

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; Green chemistry;54%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

4-methoxybenzoic acid
100-09-4

4-methoxybenzoic acid

A

ethoxymethyl 4-methoxybenzoate
1380825-76-2

ethoxymethyl 4-methoxybenzoate

B

1,2-diethoxyethyl 4-methoxybenzoate
1380825-77-3

1,2-diethoxyethyl 4-methoxybenzoate

Conditions
ConditionsYield
With copper(I) oxide; oxygen; potassium carbonate at 110℃; under 760.051 Torr; for 18h;A 43%
B 50%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(2-isocyano-5-methylphenyl)(methyl)sulfane

(2-isocyano-5-methylphenyl)(methyl)sulfane

2-(1-(2-ethoxyethoxy)ethyl)-6-methylbenzo[d]thiazole

2-(1-(2-ethoxyethoxy)ethyl)-6-methylbenzo[d]thiazole

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; Green chemistry;50%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(5-chloro-2-isocyanophenyl)(methyl)sulfane

(5-chloro-2-isocyanophenyl)(methyl)sulfane

6-chloro-2-(1-(2-ethoxyethoxy)ethyl)benzo[d]thiazole

6-chloro-2-(1-(2-ethoxyethoxy)ethyl)benzo[d]thiazole

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile at 20℃; for 24h; Inert atmosphere; Irradiation; Green chemistry;48%
benzoimidazole
51-17-2

benzoimidazole

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

A

1-(1-(2-ethoxyethoxy)ethyl)-1H-benzo[d]imidazole
1224507-26-9

1-(1-(2-ethoxyethoxy)ethyl)-1H-benzo[d]imidazole

B

1-(1,2-diethoxyethyl)-1H-benzo[d]imidazole
1224507-27-0

1-(1,2-diethoxyethyl)-1H-benzo[d]imidazole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iron(III) chloride hexahydrate In decane; ethyl acetate at 80℃; for 3h; Inert atmosphere; Molecular sieve;A 46%
B 40%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

tungsten(VI) chloride
13283-01-7

tungsten(VI) chloride

A

[WCl5(κ1-OCH2CH2OEt)]

[WCl5(κ1-OCH2CH2OEt)]

B

[WCl4(κ2-EtOCH2CH2OEt)]

[WCl4(κ2-EtOCH2CH2OEt)]

Conditions
ConditionsYield
In dichloromethane at 24.84℃; for 24h;A 45%
B 9%
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

A

2-(1-(2-ethoxyethoxy)ethyl)benzo[d]thiazole

2-(1-(2-ethoxyethoxy)ethyl)benzo[d]thiazole

B

C13H17NO2S

C13H17NO2S

Conditions
ConditionsYield
With tert.-butylhydroperoxide In decane at 100℃; for 24h; Inert atmosphere;A 45%
B 21%
monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

2-methyl-N-(2-(pyridin-2-yl)propan-2-yl)benzamide
1620193-47-6

2-methyl-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

A

2-(1-(2-ethoxyethoxy)ethyl)-6-methyl-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

2-(1-(2-ethoxyethoxy)ethyl)-6-methyl-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

B

2-(1,2-diethoxyethyl)-6-methyl-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

2-(1,2-diethoxyethyl)-6-methyl-N-(2-(pyridin-2-yl)propan-2-yl)benzamide

Conditions
ConditionsYield
With di-tert-butyl peroxide; bis(acetylacetonato)cobalt(II) at 140℃; for 12h; Schlenk technique; Inert atmosphere;A 36%
B 42%
perfluoropropylene
116-15-4

perfluoropropylene

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

1,1,1,2,3,3,10,10,11,12,12,12-dodecafluoro-4,9-dimethyl-6-(1,1,2,3,3,3-hexafluoropropyl)-5,8-dioxadodecane
166166-63-8

1,1,1,2,3,3,10,10,11,12,12,12-dodecafluoro-4,9-dimethyl-6-(1,1,2,3,3,3-hexafluoropropyl)-5,8-dioxadodecane

Conditions
ConditionsYield
In acetone for 72h; Addition; UV-irradiation;41%
α-picoline
109-06-8

α-picoline

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

A

2-(1-(2-ethoxyethoxy)ethyl)-6-methylpyridine

2-(1-(2-ethoxyethoxy)ethyl)-6-methylpyridine

B

2-(1,2-diethoxyethyl)-6-methylpyridine

2-(1,2-diethoxyethyl)-6-methylpyridine

Conditions
ConditionsYield
With di-tert-butyl peroxide; yttrium(III) trifluoromethanesulfonate at 120℃; for 24h; Sealed tube;A 33%
B 14%
triiron dodecarbonyl
17685-52-8

triiron dodecarbonyl

(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

triethylamine
121-44-8

triethylamine

phenylmercury(II) chloride
100-56-1

phenylmercury(II) chloride

[(μ-SHg(phenyl))[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ]

[(μ-SHg(phenyl))[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ]

Conditions
ConditionsYield
In tetrahydrofuran N2; stirring Fe3(CO)12, CH3(CH2OCH2)2CH3, triethylamine in THF at room temp. for 45 min, adding (S2)Fe2(CO)6 to the resulting soln., stirring for 2 h at room temp., addn. of ClHgC6H5, stirring for 24 h; solvent removal under reduced pressure, chromy. (TLC, CH2Cl2/petroleum ether 2:1 vol.); elem. anal.;30%
triiron dodecarbonyl
17685-52-8

triiron dodecarbonyl

(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

1,2-bis-(2-bromo-ethoxy)-ethane
31255-10-4

1,2-bis-(2-bromo-ethoxy)-ethane

triethylamine
121-44-8

triethylamine

[[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ]2
681801-92-3

[[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ]2

Conditions
ConditionsYield
In tetrahydrofuran N2; stirring Fe3(CO)12, CH3(CH2OCH2)2CH3, triethylamine in THF at room temp. for 45 min, adding (S2)Fe2(CO)6 to the resulting soln., stirring for 2 h at room temp., addn. of BrCH2(CH2OCH2)2CH2Br, stirring for 24 h; solvent removal under reduced pressure, chromy. (TLC, CH2Cl2/petroleum ether 2:1 vol.); elem. anal.;23%
triiron dodecarbonyl
17685-52-8

triiron dodecarbonyl

(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

triethylamine
121-44-8

triethylamine

[(μ-SCH2COO(ethyl)[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ]
681801-81-0

[(μ-SCH2COO(ethyl)[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ]

Conditions
ConditionsYield
In tetrahydrofuran N2; stirring Fe3(CO)12, CH3(CH2OCH2)2CH3, triethylamine in THF at room temp. for 45 min, adding (S2)Fe2(CO)6 to the resulting soln., stirring for 2 h at room temp., addn. of ClCH2C(O)OC2H5, stirring for 24 h; solvent removal under reduced pressure, chromy. (TLC, CH2Cl2/petroleum ether 2:1 vol.); elem. anal.;20%
triiron dodecarbonyl
17685-52-8

triiron dodecarbonyl

(μ-dithio)bis(tricarbonyliron)
14243-23-3

(μ-dithio)bis(tricarbonyliron)

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

1-bromo-2-{2-[2-(2-bromoethoxy)ethoxy]-ethoxy}ethane
31255-26-2

1-bromo-2-{2-[2-(2-bromoethoxy)ethoxy]-ethoxy}ethane

triethylamine
121-44-8

triethylamine

[[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ][μ-SCH2(CH2OCH2)3CH2S-μ]
681801-97-8

[[Fe2(CO)6]2(μ4-S)]2[μ-SCH2(CH2OCH2)2CH2S-μ][μ-SCH2(CH2OCH2)3CH2S-μ]

Conditions
ConditionsYield
In tetrahydrofuran N2; stirring Fe3(CO)12, CH3(CH2OCH2)2CH3, triethylamine in THF at room temp. for 45 min, adding (S2)Fe2(CO)6 to the resulting soln., stirring for 2 h at room temp., addn. of BrCH2(CH2OCH2)3CH2Br, stirring for 24 h; solvent removal under reduced pressure, chromy. (TLC, CH2Cl2/petroleum ether 2:1 vol.); elem. anal.;19%
(5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinato)rhodium(III) iodide
85990-32-5

(5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinato)rhodium(III) iodide

monoethylene glycol diethyl ether
629-14-1

monoethylene glycol diethyl ether

(5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate)rhodium(III) methyl

(5,10,15,20-tetra(2,4,6-trimethylphenyl)porphyrinate)rhodium(III) methyl

Conditions
ConditionsYield
With KOH In further solvent(s) reaction of rhodium compd. with diisopentyl ether in presence of 10 equiv. of KOH at 100°C for 1 d under N2;19%

629-14-1Relevant articles and documents

METHOD FOR PREPARING DOUBLE-SEALED-END GLYCOL ETHER

-

Paragraph 0042; 0043; 0045; 0047, (2017/12/27)

Disclosed is a method for preparing a double end capped glycol ether, the method comprising: introducing into a reactor a raw material comprising a glycol monoether and a monohydric alcohol ether, and enabling the raw material to contact and react with an acidic molecular sieve catalyst to generate a double end capped glycol ether, a reaction temperature being 50-300° C., a reaction pressure being 0.1-15 MPa, a WHSV of the glycol monoether in the raw material being 0.01-15.0 h?1, and a mole ratio of the monohydric alcohol ether to the glycol monoether in the raw material being 1-100:1. The method of the present invention enables a long single-pass lifespan of the catalyst and repeated regeneration, has a high yield and selectivity of a target product, low energy consumption during separation of the product, a high economic value of a by-product, and is flexible in production scale and application.

Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol

Yu, Weiqiang,Lu, Fang,Huang, Qianqian,Lu, Rui,Chen, Shuai,Xu, Jie

supporting information, p. 3327 - 3333 (2017/07/28)

Etherification of ethylene glycol with methanol provides a sustainable route for the production of widely used dimethoxyethane; dimethoxyethane is a green solvent and reagent that is applied in batteries and used as a potential diesel fuel additive. SAPO-34 zeolite was found to be an efficient and highly selective catalyst for this etherification via a continuous flow experiment. It achieved up to 79.4% selectivity for dimethoxyethane with around 96.7% of conversion. The relationship of the catalyst's structure and the dimethoxyethane selectivity was established via control experiments. The results indicated that the pore structure of SAPO-34 effectively limited the formation of 1,4-dioxane from activated ethylene glycol, enhanced the reaction of the activated methanol with ethylene glycol in priority, and thus resulted in high selectivity for the desired products. The continuous flow technology used in the study could efficiently promote the complete etherification of EG with methanol to maintain high selectivity for dimethoxyethane.

Preparation method for double-terminated glycol ether

-

Paragraph 0068; 0069; 0070; 0097, (2017/04/03)

The invention discloses a preparation method for double-terminated glycol ether. The preparation method comprises the following steps: a) introducing raw materials containing glycol monoether and monohydric ether alcohol into a reactor for contact and reaction with an acidic molecular sieve catalyst under the conditions that reaction temperature is 50 to 300 DEG C, reaction pressure is 0.1 to 15 MPa, the mass space velocity of the glycol monoether in the raw materials is 0.01 to 15.0/h, and a mol ratio of monohydric ether alcohol to glycol monoether in the raw materials is 1-100: 1, and separating obtained products so as to obtain a double-terminated glycol ether product, unreacted glycol monoether and monohydric ether alcohol, by-product components and other components; and b) returning the unreacted glycol monoether and monohydric ether alcohol and the by-product components obtained in the step a) to the reactor. The preparation method has the advantages that the catalyst has long single-pass life; the target product, i.e., double-terminated glycol ether has high yield and selectivity; energy consumption in separation of the products is low; by-products have high economic value; production scale can be large or small; and application of the method is flexible.

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