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112-27-6

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112-27-6 Usage

Description

Triethylene Glycol (TEG) is the third members of a homologous series of dihydroxyalcohols. TEG is produced in the Master Process by the direct hydration of ethylene oxide. TEG is co-produced with MEG and DEG. TEG is a colourless liquid.The main uses for triethylene glycol are based upon its hygroscopic quality. It is used as a dehydrating agent for natural gas pipelines where it removes the water from the gas before being condensed and reused in the system. It is also a dehumidifying agent in air-conditioning units.It is also used to make chemical intermediates such as plasticisers and polyester resins. It is an additive in hydraulic fluids and brake fluids, and TEG is also used as a solvent in many applications, including as a selective solvent for aromatics, and a solvent in textile dyeing.Triethylene glycol also has mild disinfectant qualities and, when volatised, is used as an air disinfectant for virus and bacteria control.

Chemical Properties

Triethylene glycol is a clear, colorless, viscous, stable liquid with a slightly sweetish odor. Soluble in water; immiscible with benzene, toluene, and gasoline. Combustible. Because it has two ether and two hydroxyl groups its chemical properties are closety related to ethers and primary alcohols. It is a good solvent for gums, resins, nitrocellulose, steam-set printing inks and wood stains. With a low vapor pressure and a high boiling point, its uses and properties are similar to those of ethylene glycol and diethylene glycol. Because it is an efficient hygroscopic agent it serves as a liquid desiccant for removing water from natural gas. It is also used in air conditioning systems designed to dehumidify air.

Uses

Different sources of media describe the Uses of 112-27-6 differently. You can refer to the following data:
1. triethylene glycol is a solvent prepared from ethylene oxide and ethylene glycol.Triethylene glycol can be used:To prepare fatty acid gelators, which are used to gelate various edible and vegetable oils.As a solvent to prepare superparamagnetic iron oxide nanoparticles for in situ protein purification.As an absorbent agent in the subsea natural gas dehydration process.
2. In various plastics to increase pliability; in air disinfection.
3. Triethylene glycol is used as a plasticizer, as an additive for hydraulic fluids and brake fluids, and as a disinfectant. It is an active component of certain pigments, printing dyes, inks and paste. It finds application as a liquid desiccant and used in the dehydration of natural gas, carbon dioxide, hydrogen sulfide and air conditioning systems. It plays as an important role in anti-freeze and de-icing products, cleaning and furnishing care products, lubricant and greases.
4. Triethylene glycol is widely used as an excellent dehydrating agent for natural gas, oilfield associated gas and carbon dioxide; Used as solvent for nitrocellulose, rubber, resin, grease, paint, pesticide, etc; Used as air bactericide; Used as triethylene glycol ester plasticizer for PVC, polyvinyl acetate resin, glass fiber and asbestos pressing board; Used as anti drying agent of tobacco, fiber lubricant and desiccant of natural gas; It is also used in organic synthesis, such as the production of brake oil with high boiling point and good low temperature performance. It can be used in gas chromatography as extractant.

Definition

ChEBI: A poly(ethylene glycol) that is octane-1,8-diol in which the carbon atoms at positions 3 and 6 have been replaced by oxygen atoms.

Production Methods

Triethylene glycol, like diethylene glycol, is produced commercially as a by-product of ethylene glycol production. Its formation is favored by a high ethylene oxide to water ratio.

General Description

Colorless liquid with a mild odor. Dense than water.

Reactivity Profile

Triethylene glycol is a ether-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. Reacts with strong oxidants. [Handling Chemicals Safely 1980. p. 932].

Health Hazard

Under normal conditions of use, Triethylene Glycol (TEG) is not expected to cause irritation to the skin, eyes or respiratory tract. However, in applications where vapours or mists are created, inhalation may cause irritation to the respiratory system. No ceiling on worker exposure has been set by the American Conference of Governmental Hygienists (ACGIH), neither has a Workplace Exposure Limit been established for TEG. TEG is readily biodegradable, has a low potential to bioaccumulate and has low toxicity to aquatic organisms. TEG is not flammable, unless preheated.

Flammability and Explosibility

Notclassified

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Poison by intravenous route. Mildly toxic to humans by ingestion. Experimental reproductive effects. An eye and skin irritant. Many glycol ether compounds have dangerous human reproductive effects. Combustible when exposed to heat or flame. Can react with oxidizing materials. Explosive in the form of vapor when exposed to heat, flame, or spark. To fight fire, use alcohol foam, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS and GLYCOL ETHERS.

Purification Methods

Dry the glycol with CaSO4 for 1 week, then it is repeatedly and very slowly fractionally distilled under a vacuum. Store it in a vacuum desiccator over P2O5. It is very hygroscopic. [Beilstein 1 IV 2400.]

Check Digit Verification of cas no

The CAS Registry Mumber 112-27-6 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 2 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 112-27:
(5*1)+(4*1)+(3*2)+(2*2)+(1*7)=26
26 % 10 = 6
So 112-27-6 is a valid CAS Registry Number.
InChI:InChI=1/C6H14O4/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2

112-27-6 Well-known Company Product Price

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

  • (A10772)  Triethylene glycol, 99%   

  • 112-27-6

  • 500ml

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A10772)  Triethylene glycol, 99%   

  • 112-27-6

  • 2500ml

  • 446.0CNY

  • Detail
  • Alfa Aesar

  • (A10772)  Triethylene glycol, 99%   

  • 112-27-6

  • 10000ml

  • 1600.0CNY

  • Detail
  • USP

  • (1683708)  Triethyleneglycol  United States Pharmacopeia (USP) Reference Standard

  • 112-27-6

  • 1683708-0.5ML

  • 4,647.24CNY

  • Detail

112-27-6SDS

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 triethylene glycol

1.2 Other means of identification

Product number -
Other names Triethylene glycol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adsorbents and absorbents,Functional fluids (closed systems),Functional fluids (open systems),Intermediates,Processing aids, specific to petroleum production,Solvents (for cleaning or degreasing),Solvents (which become part of product formulation or mixture)
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:112-27-6 SDS

112-27-6Synthetic route

methyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate
1447497-19-9

methyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate

A

2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoic acid
1447497-21-3

2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoic acid

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With methanol; water; sodium hydroxide for 2h; Reflux;A 72%
B n/a
triethylene glycol bromide

triethylene glycol bromide

2,5-dihydroxy-4-nitrobenzoic acid methyl ester
1447497-17-7

2,5-dihydroxy-4-nitrobenzoic acid methyl ester

A

2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoic acid
1447497-20-2

2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoic acid

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
Stage #1: triethylene glycol bromide; methyl 2,5-dihydroxy-4-nitrobenzoate With potassium carbonate In acetone Inert atmosphere; Reflux;
Stage #2: With methanol; water; sodium hydroxide for 2h; Reflux;
A 50%
B n/a
oxirane
75-21-8

oxirane

ethylene glycol
107-21-1

ethylene glycol

A

diethylene glycol
111-46-6

diethylene glycol

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 100℃;
oxirane
75-21-8

oxirane

ethylene glycol
107-21-1

ethylene glycol

A

Tetraethylene glycol
112-60-7

Tetraethylene glycol

B

diethylene glycol
111-46-6

diethylene glycol

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 130 - 210℃; unter Druck, 1 Mol Aethylenoxyd;
oxirane
75-21-8

oxirane

ethylene glycol
107-21-1

ethylene glycol

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 100℃;
barium(II) oxide at 275℃; for 70h; Yield given;
oxirane
75-21-8

oxirane

diethylene glycol
111-46-6

diethylene glycol

A

Tetraethylene glycol
112-60-7

Tetraethylene glycol

B

Pentaethylene glycol
4792-15-8

Pentaethylene glycol

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

oxirane
75-21-8

oxirane

A

ethylene glycol
107-21-1

ethylene glycol

B

diethylene glycol
111-46-6

diethylene glycol

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 180 - 200℃; Hydrolysis;
With water at 100℃; pH=6; Product distribution / selectivity; Multiclave;
With water; CR11:H+2 at 100℃; pH=5; Product distribution / selectivity; Multiclave;
oxirane
75-21-8

oxirane

A

diethylene glycol
111-46-6

diethylene glycol

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With water at 160 - 200℃; under 11032.6 - 14710.2 Torr;
ethylene glycol
107-21-1

ethylene glycol

ethylene dibromide
106-93-4

ethylene dibromide

A

Tetraethylene glycol
112-60-7

Tetraethylene glycol

B

Pentaethylene glycol
4792-15-8

Pentaethylene glycol

C

diethylene glycol
111-46-6

diethylene glycol

D

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 115 - 120℃; Produkt5: Hexaaethylenglykol;
ethylene glycol
107-21-1

ethylene glycol

ethylene dibromide
106-93-4

ethylene dibromide

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 115 - 120℃;
2-methyl-11-crown-4
68375-96-2

2-methyl-11-crown-4

A

acetaldehyde
75-07-0

acetaldehyde

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With water; hydrogenchloride In 1,4-dioxane Rate constant; Equilibrium constant; Ambient temperature; effect of alkali and alkaline earth metal chlorides, concentrations of HCl and electrolyte;
2,2-diphenyl-1,3,6,9-tetraoxacycloundecane
77130-22-4

2,2-diphenyl-1,3,6,9-tetraoxacycloundecane

A

benzophenone
119-61-9

benzophenone

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 30℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), var. temp.;
ethylene glycol
107-21-1

ethylene glycol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

diethylene glycol
111-46-6

diethylene glycol

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With carbon monoxide; Λ(+)-tris(pentane-2,5-dionato)ruthenium at 200℃; under 112509 Torr;
With carbon monoxide; Λ(+)-tris(pentane-2,5-dionato)ruthenium at 200℃; under 112509 Torr; Product distribution;
C6H14O4*Li(1+)

C6H14O4*Li(1+)

A

lithium cation

lithium cation

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
In acetonitrile at 25℃; Rate constant; Equilibrium constant; different concentrations;
Glyoxal
131543-46-9

Glyoxal

ethylene glycol
107-21-1

ethylene glycol

A

1,4-dioxane
123-91-1

1,4-dioxane

B

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
Multistep reaction;
2-chloro-ethanol
107-07-3

2-chloro-ethanol

aqueous NaOH-solution

aqueous NaOH-solution

A

ethylene glycol
107-21-1

ethylene glycol

B

diethylene glycol
111-46-6

diethylene glycol

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

iodine
7553-56-2

iodine

diethylene glycol
111-46-6

diethylene glycol

A

Tetraethylene glycol
112-60-7

Tetraethylene glycol

B

Pentaethylene glycol
4792-15-8

Pentaethylene glycol

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
at 190℃;
ethylene glycol
107-21-1

ethylene glycol

A

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

B

diethylene glycol, tetraethylene glycol

diethylene glycol, tetraethylene glycol

Conditions
ConditionsYield
With sulfuric acid
oxirane
75-21-8

oxirane

ethylene glycol
107-21-1

ethylene glycol

A

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

B

diethylene glycol, tetraethylene glycol

diethylene glycol, tetraethylene glycol

Conditions
ConditionsYield
With sulfuric acid at 90℃;
at 210℃; unter Druck;
diethylene glycol
111-46-6

diethylene glycol

A

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

B

tetraethylene glycol, pentaethylene glycol

tetraethylene glycol, pentaethylene glycol

Conditions
ConditionsYield
With iodine at 190℃;
oxirane
75-21-8

oxirane

diethylene glycol
111-46-6

diethylene glycol

A

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

B

tetraethylene glycol, pentaethylene glycol

tetraethylene glycol, pentaethylene glycol

Conditions
ConditionsYield
at 193℃;
2-(2-{[(dimethoxytrityl)oxy]ethoxy}ethoxy)ethanol
146669-11-6

2-(2-{[(dimethoxytrityl)oxy]ethoxy}ethoxy)ethanol

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With sodium periodate In acetone at 20℃; for 16h;
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-[2-(2-{2-[2-(2-methoxyethoxy)ethoxy]acetoxy}ethoxy)ethoxy]ethyl ester
862072-76-2

bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-[2-(2-{2-[2-(2-methoxyethoxy)ethoxy]acetoxy}ethoxy)ethoxy]ethyl ester

A

2-[2-(2-methoxyethoxy)etoxy]acetic acid
16024-58-1

2-[2-(2-methoxyethoxy)etoxy]acetic acid

B

bicyclo[2.2.1]hept-2-ene-5-carbonyl chloride
27063-48-5, 34733-86-3, 37750-50-8, 117835-14-0, 143916-13-6

bicyclo[2.2.1]hept-2-ene-5-carbonyl chloride

C

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With phosphate-buffered saline at 80℃; pH=7.4; Kinetics; Further Variations:; pH-values; Temperatures;
oxirane
75-21-8

oxirane

methyloxirane
75-56-9, 16033-71-9

methyloxirane

A

Reaxys ID: 15741318

Reaxys ID: 15741318

B

ethylene glycol
107-21-1

ethylene glycol

C

diethylene glycol
111-46-6

diethylene glycol

D

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
Stage #1: Pentaerythritol; methyloxirane With potassium hydroxide In water at 150℃; under 2250.23 - 3000.3 Torr; for 1.5h;
Stage #2: oxirane at 150℃; under 2250.23 - 3000.3 Torr; for 2.5h;
Stage #3: With acetic acid pH=~ 6; Product distribution / selectivity;
oxirane
75-21-8

oxirane

carbon dioxide
124-38-9

carbon dioxide

A

[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

B

ethylene glycol
107-21-1

ethylene glycol

C

diethylene glycol
111-46-6

diethylene glycol

D

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With Polyglykol DME 500; water; potassium iodide at 200℃; for 2h; Product distribution / selectivity;
pentaethylene glycol
2615-15-8

pentaethylene glycol

A

formic acid
64-18-6

formic acid

B

Tetraethylene glycol
112-60-7

Tetraethylene glycol

C

Pentaethylene glycol
4792-15-8

Pentaethylene glycol

D

ethylene glycol
107-21-1

ethylene glycol

E

acetic acid
64-19-7

acetic acid

F

diethylene glycol
111-46-6

diethylene glycol

G

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

Conditions
ConditionsYield
With titanium(IV) oxide In water for 24h; Concentration; UV-irradiation;
trityl chloride
76-83-5

trityl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

10,10,10-triphenyl-3,6,9-trioxadecan-1-ol
133699-09-9

10,10,10-triphenyl-3,6,9-trioxadecan-1-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h; Inert atmosphere;100%
With pyridine at 45℃; for 16h; Etherification;99%
With pyridine at 45℃;95%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol di-(p-toluenesulfonate)
19249-03-7

triethylene glycol di-(p-toluenesulfonate)

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 24h;100%
With potassium hydroxide In dichloromethane at 0℃; for 3h;100%
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydroxide In tetrahydrofuran; water at 0℃; for 1h;
Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; water at 20℃;
100%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol
201037-95-8

2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.666667h;
Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 20℃; for 23h;
100%
With pyridine; dmap at 20℃;84%
With dmap In dichloromethane at 0 - 20℃; for 4h;80.2%
D,L-4,5-Dihydro-3-isocyanato-(3H)-thiophen-2-on
38869-93-1

D,L-4,5-Dihydro-3-isocyanato-(3H)-thiophen-2-on

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

C11H19NO6S

C11H19NO6S

Conditions
ConditionsYield
With dibutyltin(II) dilaurate In ethyl acetate at 65℃; for 4h; Schlenk technique; Inert atmosphere;100%
ethyl 2-bromo-4-(4-(trifluoromethyl)phenyl)thiazole-5-carboxylate

ethyl 2-bromo-4-(4-(trifluoromethyl)phenyl)thiazole-5-carboxylate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-4-(4-(trifluoromethyl)phenyl)thiazole-5-carboxylic acid

2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-4-(4-(trifluoromethyl)phenyl)thiazole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydride In mineral oil at 0 - 20℃; for 0.166667h; Inert atmosphere;
Stage #2: ethyl 2-bromo-4-(4-(trifluoromethyl)phenyl)thiazole-5-carboxylate In mineral oil at 60℃; for 5h; Inert atmosphere;
100%
2-isocyanato-2-methylpropane-1,3-diyl diacrylate
886577-76-0

2-isocyanato-2-methylpropane-1,3-diyl diacrylate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

2-(((2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)carbonyl)amino)-2-methylpropane-1,3-diyl diacrylate

2-(((2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)carbonyl)amino)-2-methylpropane-1,3-diyl diacrylate

Conditions
ConditionsYield
With dibutyltin dilaurate; 4-methoxy-phenol In diethyl ether at 40℃; for 12h; Flow reactor;99.7%
With dibutyltin dilaurate; 4-methoxy-phenol In tetrahydrofuran at 75℃; for 5h;
2-Isocyanatoethyl methacrylate
30674-80-7

2-Isocyanatoethyl methacrylate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

13-hydroxy-4-oxo-5,8,11-trioxa-3-azatridecyl methacrylate

13-hydroxy-4-oxo-5,8,11-trioxa-3-azatridecyl methacrylate

Conditions
ConditionsYield
With dibutyltin dilaurate; 4-methoxy-phenol In diethyl ether at 40℃; for 12h; Flow reactor;99.5%
With dibutyltin dilaurate; 4-methoxy-phenol In tetrahydrofuran at 75℃; for 5h;
2-(2-methacryloyloxyethyloxy)ethyl isocyanate
107023-60-9

2-(2-methacryloyloxyethyloxy)ethyl isocyanate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

16-hydroxy-7-oxo-3,8,11,14-tetraoxa-6-azahexadecyl methacrylate

16-hydroxy-7-oxo-3,8,11,14-tetraoxa-6-azahexadecyl methacrylate

Conditions
ConditionsYield
With dibutyltin dilaurate; 4-methoxy-phenol In diethyl ether at 40℃; for 12h; Flow reactor;99.3%
With dibutyltin dilaurate; 4-methoxy-phenol In tetrahydrofuran at 75℃; for 5h;
benzyl chloride
100-44-7

benzyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol monobenzyl ether
55489-58-2

triethylene glycol monobenzyl ether

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran; mineral oil for 0.333333h;
Stage #2: benzyl chloride In tetrahydrofuran; mineral oil for 24h; Reflux; Inert atmosphere;
99%
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydroxide In water at 20℃; for 0.5h;
Stage #2: benzyl chloride In water at 100℃; for 24h;
80.7%
With sodium hydroxide at 100℃; for 24h;73%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

8-tosyloxy-3,6-dioxaoctanol
77544-68-4

8-tosyloxy-3,6-dioxaoctanol

Conditions
ConditionsYield
at 0 - 20℃; Alkaline conditions;99%
With sodium hydroxide96%
With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;96%
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,4-dioxane
123-91-1

1,4-dioxane

Conditions
ConditionsYield
With copper(ll) bromide at 175℃; for 6h; Inert atmosphere; Sealed tube;99%
With Sulfate; zirconium(IV) oxide at 180℃; for 1.41667h; cyclodehydration;
acryloyl chloride
814-68-6

acryloyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester
1680-21-3

2-propenoic acid 1,2 ethanediylbis(oxy-2,1-ethanediyl) ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 1h;99%
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With triethylamine In dichloromethane at 0℃; Inert atmosphere;
Stage #2: acryloyl chloride In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;
57%
4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane
56706-10-6

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

bis[tri(hydroxytriethyleneoxy)silylpropyl] disulfide
1036978-39-8

bis[tri(hydroxytriethyleneoxy)silylpropyl] disulfide

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 150℃; under 20 Torr; for 2h; Under reduced presure;99%
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

3-Iodobenzoic acid
618-51-9

3-Iodobenzoic acid

C20H20I2O6

C20H20I2O6

Conditions
ConditionsYield
With dmap; diisopropyl-carbodiimide In dichloromethane99%
4-methoxy-phenol
150-76-5

4-methoxy-phenol

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,10-bis(4-methoxyphenyl)-1,4,7,10-tetraoxaundecane
141788-62-7

1,10-bis(4-methoxyphenyl)-1,4,7,10-tetraoxaundecane

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In acetonitrile at 85℃; for 30h; Temperature; Time;98.46%
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol bis(dichlorophosphate)
352546-86-2

triethylene glycol bis(dichlorophosphate)

Conditions
ConditionsYield
With trichlorophosphate In dichloromethane at 20℃;98%
With trichlorophosphate
1,11-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3,6,9-trioxaundecane-1,11-dione
577794-93-5

1,11-bis(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-3,6,9-trioxaundecane-1,11-dione

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,4,7,10,15,18,21-heptaoxacyclopentacosane-11,13,23,25-tetraone

1,4,7,10,15,18,21-heptaoxacyclopentacosane-11,13,23,25-tetraone

Conditions
ConditionsYield
In chlorobenzene Heating;98%
butanoic acid methyl ester
623-42-7

butanoic acid methyl ester

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol di-n-butyrate
26962-26-5

triethylene glycol di-n-butyrate

Conditions
ConditionsYield
With potassium carbonate at 100 - 110℃;98%
propanoic acid methyl ester
554-12-1

propanoic acid methyl ester

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol dipropionate
141-34-4

triethylene glycol dipropionate

Conditions
ConditionsYield
With potassium carbonate at 90 - 95℃;98%
butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol di-n-butyrate
26962-26-5

triethylene glycol di-n-butyrate

Conditions
ConditionsYield
With potassium carbonate at 115 - 140℃;98%
methyl valerate
624-24-8

methyl valerate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol di-n-pentanoate
97766-66-0

triethylene glycol di-n-pentanoate

Conditions
ConditionsYield
With potassium carbonate at 126 - 165℃; under 750.075 Torr;98%
benzoic acid
65-85-0

benzoic acid

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol dibenzoate
120-56-9

triethylene glycol dibenzoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 180 - 210℃;97%
With H2SO4/TiO2-La2O3-solid acid catalyst In 5,5-dimethyl-1,3-cyclohexadiene at 185 - 190℃; for 11h;92.6%
With toluene-4-sulfonic acid; xylene
With tin(IV) oxide In 5,5-dimethyl-1,3-cyclohexadiene at 180℃;
divinyl sulfoxide
1115-15-7

divinyl sulfoxide

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

C34H66O16S4

C34H66O16S4

Conditions
ConditionsYield
With sodium hydroxide at 65℃; for 5h;97%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethyleneglycol dimesylate
80322-82-3

triethyleneglycol dimesylate

Conditions
ConditionsYield
With triethylamine In dichloromethane97%
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With triethylamine In dichloromethane at 0℃; for 0.166667h;
Stage #2: methanesulfonyl chloride In dichloromethane at 20℃; for 12h;
92.9%
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;86%
4-benzoylbenzoyl chloride
39148-58-8

4-benzoylbenzoyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

1,8-Bis(4-benzoylbenzoyloxy)-3,6-dioxaoctane

1,8-Bis(4-benzoylbenzoyloxy)-3,6-dioxaoctane

Conditions
ConditionsYield
With pyridine In dichloromethane Ambient temperature;97%
cis-1,2,3,6-tetrahydrophthalic anhydride
935-79-5

cis-1,2,3,6-tetrahydrophthalic anhydride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

C22H30O10
888485-47-0

C22H30O10

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 9h;97%
2-Ethylhexanoic acid
149-57-5

2-Ethylhexanoic acid

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol bis(2-ethylhexanoate)
94-28-0

triethylene glycol bis(2-ethylhexanoate)

Conditions
ConditionsYield
With titanium(IV) isopropylate at 220℃; under 225.023 - 450.045 Torr; for 3h; Reagent/catalyst; Pressure; Time; Concentration; pH-value;97%
With pyrographite at 225℃; under 300.03 - 675.068 Torr; for 14.5h; Product distribution / selectivity;
With pyrographite at 225℃; under 300.03 - 675.068 Torr; for 14.5h; Product distribution / selectivity;
para-iodoanisole
696-62-8

para-iodoanisole

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

2-[2-[2-(4-methoxyphenoxy)ethoxy]ethoxy]ethanol
167567-16-0

2-[2-[2-(4-methoxyphenoxy)ethoxy]ethoxy]ethanol

Conditions
ConditionsYield
With potassium carbonate; copper(l) chloride at 130℃; for 24h; Inert atmosphere;97%
Hexanoyl chloride
142-61-0

Hexanoyl chloride

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

triethylene glycol di-n-hexanoate
25176-75-4

triethylene glycol di-n-hexanoate

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane for 3h;96%
tert-Butyl acrylate
1663-39-4

tert-Butyl acrylate

2,2'-[1,2-ethanediylbis(oxy)]bisethanol
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester
186020-66-6

3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium In tetrahydrofuran at 20℃;
Stage #2: tert-Butyl acrylate In tetrahydrofuran at 20℃; for 20h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran
96%
With sodium In tetrahydrofuran at 20℃; for 24h;95.5%
With sodium In tetrahydrofuran for 20h;86%

112-27-6Relevant articles and documents

Boigegrain,R. et al.

, p. 2529 - 2530 (1975)

Substituted diether diols by ring-opening of carbocyclic and stannylene acetals

Martinez-Bernhardt, Rolando,Castro, Peter P.,Godjoian, Gayane,Gutierrez, Carlos G.

, p. 8919 - 8932 (1998)

Reduction of malonaldehyde bis(ethylene and propylene acetals) with borane or monochloroborane produces diether diols 1 and 2 in high yield. Similar reduction of glyoxal his(ethylene acetals) has only limited utility for the preparation of tetrasubstituted triethylene glycols 3. Organotin chemistry is complementary: stannylene acetals prepared from disubstituted vicinal diols can be alkylated with half an equivalent of 1,2-dibromoethane to produce tetrasubstituted triethylene glycols 3, or with two equivalents of 2-chloroethanol to produce disubstituted triethylene glycols 4.

CO2atmosphere enables efficient catalytic hydration of ethylene oxide by ionic liquids/organic bases at low water/epoxide ratios

Ding, Tong,Gao, Guohua,Xia, Fei,Yuan, Huixia,Zha, Jinyin,Zhang, Dawei,Zhang, Jingshun

supporting information, p. 3386 - 3391 (2021/05/25)

The development of an efficient and low-cost strategy for the production of monoethylene glycol (MEG) through hydration of ethylene oxide (EO) at low H2O/EO molar ratios is an important industrial challenge. We have established that by using CO2as the reaction atmosphere, hydration of EO can be achieved at a low H2O/EO ratio of 1.5?:?1 along with high yields (88-94%) and selectivities (91-97%) of MEG catalyzed by binary catalysts of ionic liquids and organic bases. The results are significantly better than those of experiments conducted under an atmosphere of N2. Isotope labeling experiments revealed that CO2had altered the reaction pathway and participated in the reaction, in which cycloaddition of EO with CO2occurred first followed by the hydrolysis of ethylene carbonate (EC) to generate MEG and recover CO2. The ionic liquids and organic bases synergistically catalyzed the one-pot two-step reaction. DFT calculations confirmed that this route is more kinetically favorable compared to the pathway of direct epoxide hydration.

Catalytic hydration process for production of ethylene glycol

-

Paragraph 0035-0042, (2017/02/24)

The invention relates to a method for producing glycol by catalytic hydration, which solves the problems of high equipment investment and high energy consumption existed in the direct hydration production of glycol in prior art. The method comprises the following steps: a) a material flow 1 containing ethylene oxide and water is introduced in a catalytic hydration reaction unit R, a material flow 6 containing glycol can be obtained after the reaction; b) the material flow 6 is introduced in a feed preheater of an evaporation tower D3, and preheating is carried out to obtain a material flow 7; c) the material flow 7 is introduced in the center part of the evaporation tower, after being separated, a glycol aqueous solution 8 is obtained at the bottom of the evaporation tower, and a steam material flow 9 is obtained at the top of the tower; and d) the material flow 9 is divided into a material flow 10 and a material flow 11; the material flow 10 is introduced in the feed preheater of the evaporation tower D3; and the material flow 11 is introduced into a subsequent flow. The technical scheme can better solve the problems, and the method of the invention can be used in an industrial production for producing glycol by ethylene oxide catalytic hydration.

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