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| CAS No.: | 112-27-6 |
|---|---|
| Name: | 2,2'-(Ethylenedioxy)diethanol |
| Article Data: | 33 |
| Molecular Structure: | |
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| 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: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 58.92000 |
| LogP: | -0.99580 |
methyl 2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate
A
2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoic acid
B
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
| Conditions | Yield |
|---|---|
| With methanol; water; sodium hydroxide for 2h; Reflux; | A 72% B n/a |
2,5-dihydroxy-4-nitrobenzoic acid methyl ester
A
2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoic acid
B
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
| Conditions | Yield |
|---|---|
| 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
ethylene glycol
A
diethylene glycol
B
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
| Conditions | Yield |
|---|---|
| at 100℃; |
oxirane
ethylene glycol
A
Tetraethylene glycol
B
diethylene glycol
C
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
| Conditions | Yield |
|---|---|
| at 130 - 210℃; unter Druck, 1 Mol Aethylenoxyd; |
| Conditions | Yield |
|---|---|
| at 100℃; | |
| barium(II) oxide at 275℃; for 70h; Yield given; |
oxirane
diethylene glycol
A
Tetraethylene glycol
B
Pentaethylene glycol
C
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
oxirane
A
ethylene glycol
B
diethylene glycol
C
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| With water at 160 - 200℃; under 11032.6 - 14710.2 Torr; |
ethylene glycol
ethylene dibromide
A
Tetraethylene glycol
B
Pentaethylene glycol
C
diethylene glycol
D
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
| Conditions | Yield |
|---|---|
| at 115 - 120℃; Produkt5: Hexaaethylenglykol; |
| Conditions | Yield |
|---|---|
| at 115 - 120℃; |
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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. |
