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| CAS No.: | 107-21-1 |
|---|---|
| Name: | Ethylene glycol |
| Article Data: | 958 |
| Molecular Structure: | |
|
|
|
| Formula: | C2H6O2 |
| Molecular Weight: | 62.0684 |
| Synonyms: | Glycol;Norkool;Ethylene dihydrate;1,2-Dihydroxyethane;Monoethylene glycol;146AR;M.e.g.;Ethylenglykol;Monoethylenglykol tech.;Ethyleneglycol;Glycol alcohol;Ethylene alcohol;Tescol;ethanediol;Ethane-1,2-diol;Athylenglykol;2-hydroxyethanol;Lutrol 9;LUTROL-9;Ethylene glycol-D6;Zerex;Dowtherm SR 1;Fridex;Ucar 17;1,2-Ethanediol; |
| EINECS: | 203-473-3 |
| Density: | 1.097 g/cm3 |
| Melting Point: | -13 °C |
| Boiling Point: | 197.5 °C at 760 mmHg |
| Flash Point: | 108.2 °C |
| Solubility: | miscible with water |
| Appearance: | clear, colorless syrupy liquid |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 22-36 |
| Safety: | 26 |
| Transport Information: | UN 1219 3/PG 2 |
| PSA: | 40.46000 |
| LogP: | -1.02900 |
| Conditions | Yield |
|---|---|
| With 1,1′-(pyridine-2,6-diylbis(methylene))bis(3-butylimidazolium) dibromide; carbonylchlorohydridobis(tricyclohexylphosphine)ruthenium(II); potassium tert-butylate; hydrogen In 1,4-dioxane at 130℃; under 37503.8 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Autoclave; | A 39% B 100% |
| With hydrogen In 1,4-dioxane at 250℃; under 30003 Torr; for 4h; Temperature; Solvent; Reagent/catalyst; Flow reactor; | A 93% B 99% |
| With C24H38Cl2N3PRu; hydrogen; sodium methylate In tetrahydrofuran at 25℃; under 38002.6 Torr; for 16h; Autoclave; | A 99 %Chromat. B 95% |
[1,3]-dioxolan-2-one
methanol
A
ethylene glycol
B
carbonic acid dimethyl ester
| Conditions | Yield |
|---|---|
| anion exchanging resin at 80.4 - 98℃; for 6h; Product distribution / selectivity; | A 99% B 99.7% |
| potassium hydroxide In water at 98℃; under 838.584 Torr; for 500 - 6000h; Product distribution / selectivity; Heating / reflux; | A n/a B 99.88% |
| potassium hydroxide at 98 - 130℃; under 784.578 - 838.584 Torr; for 500 - 6000h; Product distribution / selectivity; Heating / reflux; | A n/a B 99.99% |
[1,3]-dioxolan-2-one
methanol
A
ethylene glycol
B
carbonic acid dimethyl ester
C
diethylene glycol
| Conditions | Yield |
|---|---|
| potassium hydroxide at 63.8 - 98℃; for 6.7h; Product distribution / selectivity; | A 99.1% B 99.8% C n/a |
| sodium hydroxide at 49.8 - 56.2℃; under 342.034 Torr; Product distribution / selectivity; Industry scale; | A 91.3% B 91.3% C n/a |
| potassium hydroxide at 47 - 56℃; under 228.023 - 342.034 Torr; Product distribution / selectivity; Industry scale; | A 90.5% B 90.5% C n/a |
| at 55.9 - 56℃; under 342.034 Torr; Product distribution / selectivity; Industry scale; | A 38.9% B 38.9% C n/a |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; [RuCl2(CO)2(Ph2P-3-C6H4COOH)2] In methanol; water at 75℃; for 0.333333h; | A 99.1% B n/a C n/a |
| Conditions | Yield |
|---|---|
| With C19H21N2(1+)*CHO2(1-); water at 110℃; under 15001.5 Torr; for 0.5h; Reagent/catalyst; Temperature; Autoclave; Inert atmosphere; | 99% |
| With water at 98℃; under 9000.9 Torr; Reagent/catalyst; | 95% |
| With water at 94℃; Kinetics; Concentration; Temperature; Autoclave; | 87.2% |
| Conditions | Yield |
|---|---|
| With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 0.5h; Time; Pressure; Autoclave; | 99% |
| In water at 250℃; for 2h; Temperature; Sealed tube; Inert atmosphere; | 99% |
| With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave; | 92% |
ethylene glycol
| Conditions | Yield |
|---|---|
| With methanol; bromine for 0.5h; Heating; | 99% |
| Conditions | Yield |
|---|---|
| With water under 76.0051 - 760.051 Torr; Reflux; | 99% |
| With water; silica gel In neat (no solvent) at 150℃; under 1147.61 Torr; for 24h; Autoclave; | 10% |
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In water at 160℃; under 103430 Torr; for 4h; | 98.3% |
| Conditions | Yield |
|---|---|
| With cerium(III) chloride; sodium iodide In acetonitrile for 2h; tosylate cleavage; Heating; | 98% |
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Ethylene glycol, also known as ethylene glycol, is clear, colorless, syrupy, liquid with sweet taste. It is used as an antifreeze in cooling and heating systems. In organic synthesis, it is used as a protecting group for carbonyl groups. Ethylene glycol is miscible with water, ethanol, acetone, acetic acid, glycerol, pyridine, but difficultly soluble in chloroform, ether, benzene, carbon disulfide, and insoluble in hydrocarbons, chlorinated hydrocarbons, oils, rubber, natural resin. It also can dissolve table salt, zinc chloride, potassium carbonate, potassium chloride, potassium iodide, potassium hydroxide and other inorganic compounds.
Physical properties about Ethylene glycol are: (1)ACD/LogP: -1.688; (2)# of Rule of 5 Violations:0; (3)ACD/LogD (pH 5.5): -1.69; (4)ACD/LogD (pH 7.4): -1.69; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 2.87; (8)ACD/KOC (pH 7.4): 2.87; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.422; (13)Molar Refractivity: 14.384 cm3; (14)Molar Volume: 56.561 cm3; (15)Polarizability: 5.702 10-24cm3; (16)Surface Tension: 43.4129981994629 dyne/cm; (17)Density: 1.097 g/cm3; (18)Flash Point: 108.171 °C; (19)Enthalpy of Vaporization: 50.468 kJ/mol; (20)Boiling Point: 197.539 °C at 760 mmHg ; (21)Vapour Pressure: 0.096000000834465 mmHg at 25°C
Preparation of Ethylene glycol: In industrial, Ethylene glycol can be produced by chlorohydrin method, oxirane hydration and direct ethylene hydration.
1. Chlorohydrin method: Use chlorohydrin as raw material which hydrolyzes in the alkaline medium at 100 °C. It can generate oxirane first, and then hydrolyze to produce Ethylene glycol at pressure of 1.01 MPa.
2. Oxirane hydration: This method has catalytic hydration and direct hydration. The hydration process can be carried out both at atmospheric pressure and under pressure. Ordinary pressure uses a small amount of inorganic acid as catalyst and reacts at 50 ~ 70 °C. The molar ratio of oxirane and water of pressurized hydration is higher in the 1:6 or more, in order to reduce the side effect of generating ether. The reaction temperature is 150 °C and pressure is 147kPa. Ethylene glycol can be obtained by hydration. Now, there is gas-phase catalytic hydration, which uses silver oxide as catalyst, alumina as carrier, and reacts at 150 ~ 240 °C to produce 1,2-ethanediol.
3. Direct ethylene hydration: First, the single-acetate or diacetate can be produced by oxidation from ethylene in the presence of catalyst (such as antimony oxide TeO2, palladium catalyst) in acetic acid solution. Then, Ethylene glycol is obtained by further hydrolysis.
Uses of Ethylene glycol: Ethylene glycol is mainly used to make PET melt, which accounted for 86% of total consumption in 2009, and antifreeze, at around 7% of total consumption. It also has many niche applications due to its cheaply price. Ethylene glycol is used for the manufacture of resins, plasticizers, synthetic fibers, cosmetics, explosives and engine antifreeze. What's more, it is used as raw material for polyester fiber terylene. Ethylene glycol can often be instead of glycerin used as water mixture and solvent in the leather and pharmaceutical industries, respectively. Although the dissolving capacity of Ethylene glycol is strong, it can not be widely used as a solvent. Because it can be easy to be metabolized to produce toxic oxalic acid. Besides, Ethylene glycol is used as a medium for convective heat transfer in, for example, automobiles and liquid cooled computers. It is also commonly used in chilled water air conditioning systems that place either the chiller or air handlers outside, or systems that must cool below the freezing temperature of water. In addition, minor uses of Ethylene glycol include analysis reagents, liquid chromatography eluent, non-aqueous media of electrochemical analysis, and degreaser in electronic industry.
When you are using this chemical, please be cautious about it as the following: Due to the sweet taste of 1,2-ethanediol, children and animals are more inclined to consume large quantities of it than of other poisons. It is harmful if swallowed and it is irritating to eyes. It and its toxic byproducts first affect the central nervous system, then the heart, and finally the kidneys. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)Smiles:C(CO)O;
(2)InChI:InChI=1/C2H6O2/c3-1-2-4/h3-4H,1-2H2;
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LD50 | oral | 1650mg/kg (1650mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Recueil de Medecine Veterinaire. Vol. 154, Pg. 137, 1978. |
| cat | LDLo | subcutaneous | 2gm/kg (2000mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS BLOOD: OTHER CHANGES | Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933. |
| child | TDLo | oral | 5500mg/kg (5500mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Postgraduate Medical Journal. Vol. 52, Pg. 598, 1976. |
| dog | LD50 | oral | 5500mg/kg (5500mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Recueil de Medecine Veterinaire. Vol. 154, Pg. 137, 1978. |
| guinea pig | LD50 | oral | 6610mg/kg (6610mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941. |
| guinea pig | LD50 | unreported | 11150mg/kg (11150mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT GASTROINTESTINAL: NAUSEA OR VOMITING | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(3), Pg. 16, 1968. |
| guinea pig | LDLo | subcutaneous | 5gm/kg (5000mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 51, Pg. 398, 1935. | |
| human | LDLo | oral | 398mg/kg (398mg/kg) | BEHAVIORAL: HEADACHE GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: OTHER CHANGES | Sudebno-Meditsinskaya Ekspertiza. Forensic Medical Examination. Vol. 26(2), Pg. 48, 1983. |
| human | LDLo | oral | 786mg/kg (786mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: COMA | European Journal of Toxicology and Environmental Hygiene. Vol. 9, Pg. 373, 1976. |
| human | TCLo | inhalation | 10000mg/m3 (10000mg/m3) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: COUGH LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933. |
| man | LDLo | unreported | 1637mg/kg (1637mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
| man | TDLo | oral | 1195mg/kg (1195mg/kg) | PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED | Annals of Emergency Medicine. Vol. 20, Pg. 208, 1991. |
| man | TDLo | oral | 15gm/kg (15000mg/kg) | PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED | Annals of Emergency Medicine. Vol. 20, Pg. 208, 1991. |
| man | TDLo | oral | 16gm/kg (16000mg/kg) | BEHAVIORAL: COMA KIDNEY, URETER, AND BLADDER: RENAL FUNCTION TESTS DEPRESSED | Human & Experimental Toxicology. Vol. 9, Pg. 317, 1990. |
| man | TDLo | oral | 24gm/kg (24000mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 445, 2000. |
| mouse | LC | inhalation | > 200mg/m3/2H (200mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(11), Pg. 57, 1981. | |
| mouse | LD50 | intraperitoneal | 5614mg/kg (5614mg/kg) | LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA KIDNEY, URETER, AND BLADDER: CHANGES IN BOTH TUBULES AND GLOMERULI BLOOD: CHANGES IN SPLEEN | Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 6, Pg. 342, 1947. |
| mouse | LD50 | intravenous | 3gm/kg (3000mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 65, Pg. 89, 1939. | |
| mouse | LD50 | oral | 5500mg/kg (5500mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 32(3), Pg. 31, 1967. | |
| mouse | LD50 | unreported | 8050mg/kg (8050mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: EXCITEMENT | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(3), Pg. 16, 1968. |
| mouse | LDLo | subcutaneous | 2700mg/kg (2700mg/kg) | British Journal of Industrial Medicine. Vol. 1, Pg. 207, 1944. | |
| rabbit | LD50 | skin | 9530uL/kg (9.53mL/kg) | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 731, 1969. | |
| rabbit | LD50 | unreported | 5017mg/kg (5017mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: EXCITEMENT GASTROINTESTINAL: NAUSEA OR VOMITING | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(3), Pg. 16, 1968. |
| rabbit | LDLo | intramuscular | 5500mg/kg (5500mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: COMA | Journal of Pharmacology and Experimental Therapeutics. Vol. 41, Pg. 387, 1931. |
| rabbit | LDLo | intraperitoneal | 1gm/kg (1000mg/kg) | Pesticide Chemicals Official Compendium, Association of the American Pesticide Control Officials, Inc., 1966. Vol. -, Pg. 502, 1966. | |
| rabbit | LDLo | intravenous | 5gm/kg (5000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: TREMOR | Journal of Pharmacology and Experimental Therapeutics. Vol. 41, Pg. 387, 1931. |
| rat | LC | inhalation | > 200mg/m3/4H (200mg/m3) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(11), Pg. 57, 1981. | |
| rat | LD50 | intraperitoneal | 5010mg/kg (5010mg/kg) | Kriobiologiya i Kriomeditsina. Cryobiology and Cryomedicine. Vol. 9, Pg. 36, 1981. | |
| rat | LD50 | intravenous | 3260mg/kg (3260mg/kg) | Kriobiologiya i Kriomeditsina. Cryobiology and Cryomedicine. Vol. 9, Pg. 36, 1981. | |
| rat | LD50 | oral | 4700mg/kg (4700mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 26(6), Pg. 28, 1982. | |
| rat | LD50 | subcutaneous | 2800mg/kg (2800mg/kg) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 49, 1974. | |
| rat | LD50 | unreported | 13gm/kg (13000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: EXCITEMENT | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 33(3), Pg. 16, 1968. |
| rat | LDLo | intramuscular | 3300mg/kg (3300mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Journal of Pharmacology and Experimental Therapeutics. Vol. 41, Pg. 387, 1931. |
