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112-27-6

Basic Information
CAS No.: 112-27-6
Name: 2,2'-(Ethylenedioxy)diethanol
Article Data: 33
Molecular Structure:
Molecular Structure of 112-27-6 (2,2'-(Ethylenedioxy)diethanol)
Formula: C6H14O4
Molecular Weight: 150.175
Synonyms: NSC 60758;TEG;TEG(glycol);Trigen;Triglycol;Trigol;Triethyleneglycol (8CI);1,2-Bis(2-hydroxyethoxy)ethane;1,2-Di(b-hydroxyethoxy)ethane;1,8-Dihydroxy-3,6-dioxaoctane;2,2'-Ethylenedioxydiethanol;2-[2-(2-Hydroxyethoxy)ethoxy]ethanol;3,6-Dioxaoctane-1,8-diol;Glycol bis(hydroxyethyl) ether;Triethylene glycol;
EINECS: 203-953-2
Density: 1.124 g/cm3
Melting Point: -7 °C
Boiling Point: 288 °C at 760 mmHg
Flash Point: 165.6 °C
Solubility: 50 mg/mL at 20 °C in water
Appearance: clear liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 58.92000
LogP: -0.99580
Synthetic route
1447497-19-9

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

A

1447497-21-3

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

B

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

1447497-17-7

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

A

1447497-20-2

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

B

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
75-21-8

oxirane

107-21-1

ethylene glycol

A

111-46-6

diethylene glycol

B

112-27-6

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

Conditions
ConditionsYield
at 100℃;
75-21-8

oxirane

107-21-1

ethylene glycol

A

112-60-7

Tetraethylene glycol

B

111-46-6

diethylene glycol

C

112-27-6

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

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

oxirane

107-21-1

ethylene glycol

112-27-6

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

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

oxirane

111-46-6

diethylene glycol

A

112-60-7

Tetraethylene glycol

B

4792-15-8

Pentaethylene glycol

C

112-27-6

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

75-21-8

oxirane

A

107-21-1

ethylene glycol

B

111-46-6

diethylene glycol

C

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;
75-21-8

oxirane

A

111-46-6

diethylene glycol

B

112-27-6

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

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

ethylene glycol

106-93-4

ethylene dibromide

A

112-60-7

Tetraethylene glycol

B

4792-15-8

Pentaethylene glycol

C

111-46-6

diethylene glycol

D

112-27-6

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

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

ethylene glycol

106-93-4

ethylene dibromide

112-27-6

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

Conditions
ConditionsYield
at 115 - 120℃;
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Specification

The IUPAC name of Triethylene glycol is 2-[2-(2-hydroxyethoxy)ethoxy]ethanol. With the CAS registry number 112-27-6, it is also named as 2,2'-(1,2-Ethanediylbis(oxy))bisethanol. The product's categories are ethylene glycol; ethylene glycols; ethylene glycols & monofunctional ethylene glycols. It is colorless, odorless, viscous and hygroscopic liquid which is miscible with water and ethanol, slightly soluble in ether, almost insoluble in petroleum ether. It is slightly toxic and combustible. Additionally, Triethylene glycol is non-corrosive to metal and do not react with the majority plastic and rubber. When not use, it should sealed in the container which must placed in the cool and dry aera.

The other characteristics of Triethylene glycol can be summarized as: 
(1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 2.29; (4)ACD/KOC (pH 7.4): 2.29; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 9; (8)Index of Refraction: 1.45; (9)Molar Refractivity: 36.4 cm3; (10)Molar Volume: 135.3 cm3; (11)Polarizability: 14.43×10-24 cm3; (12)Surface Tension: 41.6 dyne/cm; (13)Enthalpy of Vaporization: 61.18 kJ/mol; (14)Vapour Pressure: 0.000268 mmHg at 25 °C; (15)Rotatable Bond Count: 7; (16)Exact Mass: 150.089209; (17)MonoIsotopic Mass: 150.089209; (18)Topological Polar Surface Area: 58.9; (19)Heavy Atom Count: 10.

Preparation of Triethylene glycol: 
It is obtained, with diethylene glycol, as a by-product in the manufacture of ethylene glycol from hydrolysis of ethylene oxide.
6CH2CH2O + 3H2O → HOCH2CH2OH + HOCH2CH2OCH2CH2OH + HOCH2CH2OCH2CH2OCH2CH2OH
It is separated from the ethylene glycol and diethylene glycol by vacuum distillation.

Uses of Triethylene glycol:
It is not only used as a plasticizer for vinyl, but also used in Air-Sanitizer products. When aerosolized, it acts as a disinfectant. Additionally, Triethylene glycol is also used as liquid desiccants for natural gas and in air conditioning systems. Furthermore, it is an additive for hydraulic fluids and brake fluids and used as a base for "smoke machine" fluid in the entertainment industry. 

Safety information of Triethylene glycol:
When you are using Triethylene glycol, please be cautious about it as the following:It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
(1)Canonical SMILES: C(COCCOCCO)O
(2)InChI: InChI=1S/C6H14O4/c7-1-3-9-5-6-10-4-2-8/h7-8H,1-6H2
(3)InChIKey: ZIBGPFATKBEMQZ-UHFFFAOYSA-N

The following are the toxicity data of Triethylene glycol:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous > 4500mg/kg (4500mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1536, 1968.
 
guinea pig LD50 intravenous 10600mg/kg (10600mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1536, 1968.
 
guinea pig LD50 oral 7900mg/kg (7900mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 28, Pg. 40, 1946.
human LDLo oral 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 17, Pg. 913, 1979.
mammal (species unspecified) LD50 oral 8150mg/kg (8150mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse LD50 intraperitoneal 8141mg/kg (8141mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

BLOOD: CHANGES IN SPLEEN

KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 6, Pg. 342, 1947.
mouse LD50 intravenous 6500mg/kg (6500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 65, Pg. 89, 1939.
mouse LD50 subcutaneous 8750mg/kg (8750mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 65, Pg. 89, 1939.
mouse LDLo oral 18500mg/kg (18500mg/kg)   Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 1186, 1966.
rabbit LD50 intravenous 1900mg/kg (1900mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1536, 1968.
 
rabbit LD50 oral 8400mg/kg (8400mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 28, Pg. 40, 1946.
rabbit LD50 skin > 20mL/kg (20mL/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 731, 1969.
rat LD50 intravenous 11700mg/kg (11700mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1536, 1968.
 
rat LD50 oral 17gm/kg (17000mg/kg)   Journal of Industrial Hygiene and Toxicology. Vol. 28, Pg. 40, 1946.
rat LDLo intramuscular 8400mg/kg (8400mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 29, Pg. 5, 1940.

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