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107-21-1

Basic Information
CAS No.: 107-21-1
Name: Ethylene glycol
Article Data: 958
Molecular Structure:
Molecular Structure of 107-21-1 (Ethylene glycol)
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: HarmfulXn
Risk Codes: 22-36
Safety: 26
Transport Information: UN 1219 3/PG 2
PSA: 40.46000
LogP: -1.02900
Synthetic route
96-49-1

[1,3]-dioxolan-2-one

A

67-56-1

methanol

B

107-21-1

ethylene glycol

Conditions
ConditionsYield
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%
96-49-1

[1,3]-dioxolan-2-one

67-56-1

methanol

A

107-21-1

ethylene glycol

B

616-38-6

carbonic acid dimethyl ester

Conditions
ConditionsYield
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%
96-49-1

[1,3]-dioxolan-2-one

67-56-1

methanol

A

107-21-1

ethylene glycol

B

616-38-6

carbonic acid dimethyl ester

C

111-46-6

diethylene glycol

Conditions
ConditionsYield
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
31637-97-5

ETOFIBRATE

A

59-67-6

nicotinic acid

B

882-09-7

Clofibric acid

C

107-21-1

ethylene glycol

Conditions
ConditionsYield
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
75-21-8

oxirane

107-21-1

ethylene glycol

Conditions
ConditionsYield
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%
96-49-1

[1,3]-dioxolan-2-one

107-21-1

ethylene glycol

Conditions
ConditionsYield
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%

C34H42O2Si2

107-21-1

ethylene glycol

Conditions
ConditionsYield
With methanol; bromine for 0.5h; Heating;99%
497-26-7

2-methyl-1,3-dioxolane

107-21-1

ethylene glycol

Conditions
ConditionsYield
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%
5694-68-8

2-hydroxymethyl-1,3-dioxolane

107-21-1

ethylene glycol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In water at 160℃; under 103430 Torr; for 4h;98.3%
6315-52-2

1,2-bis-tosyloxyethane

107-21-1

ethylene glycol

Conditions
ConditionsYield
With cerium(III) chloride; sodium iodide In acetonitrile for 2h; tosylate cleavage; Heating;98%
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Specification

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.