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CAS No.: | 111-46-6 |
---|---|
Name: | Diethylene glycol |
Article Data: | 75 |
Molecular Structure: | |
Formula: | C4H10O3 |
Molecular Weight: | 106.122 |
Synonyms: | Dicol;Dissolvant APV;Bis(2-hydroxyethyl) ether;3-Oxa-1,5-pentanediol;2,2-Oxybisethanol;2,2-Di(hydroxyethyl) ether;Ethanol,2,2'-oxybis-;2, 2-Oxybis[ethanol];Ethanol, 2,2-oxydi-;DEG;TL4N;Brecolane NDG;Deactivator E;Digol;Glycol ether;Glycol ethyl ether;3-Oxapentane-1,5-diol;Digenos;2,2-Oxydiethanol;2,2-Oxyethanol;Diglycol;2-(2-hydroxyethoxy)ethanol;2, 2-Oxydiethanol;Ethylene diglycol;Ethanol, 2,2-oxybis-;Diethylenglykol;2,2'-oxydiethanol; |
EINECS: | 203-872-2 |
Density: | 1.106 g/cm3 |
Melting Point: | -10 °C(lit.) |
Boiling Point: | 245.689 °C at 760 mmHg |
Flash Point: | 143.333 °C |
Solubility: | miscible with water |
Appearance: | colorless liquid |
Hazard Symbols: | Xn,T,Xi |
Risk Codes: | 22 |
Safety: | 46 |
PSA: | 49.69000 |
LogP: | -1.01240 |
[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 |
diethylene glycol
Conditions | Yield |
---|---|
With 1,11-bis(3-methyl-3H-imidazolium-1-yl)-3,6,9-trioxaundecane di(methanesulfonate) In methanol at 20℃; for 1.5h; | 91% |
[1,3]-dioxolan-2-one
methanol
A
2-methoxy-ethanol
B
ethylene glycol
C
carbonic acid dimethyl ester
D
diethylene glycol
Conditions | Yield |
---|---|
at 76.7 - 79.6℃; under 757.576 Torr; Product distribution / selectivity; Industry scale; | A n/a B 72% C 72% D n/a |
Conditions | Yield |
---|---|
With sulfuric acid In neat (no solvent) at 150℃; under 1147.61 Torr; for 24h; Time; Autoclave; | A 9% B 65% |
With Cs-P-Si at 300℃; under 75006 Torr; |
ethylene glycol
A
2-methyl-1,3-dioxolane
B
1,4-dioxane
C
acetaldehyde
D
diethylene glycol
Conditions | Yield |
---|---|
With tungsten trioxide on silica; hydrogen In water at 340℃; Temperature; Inert atmosphere; | A 38.8% B 28.7% C 44.9% D n/a |
Conditions | Yield |
---|---|
at 130 - 210℃; unter Druck, 16 Mol Aethylenoxyd; | |
With sulfuric acid | |
at 90 - 210℃; unter Druck; | |
at 100℃; |
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 |
---|---|
With water under 37503.8 Torr; for 5h; Product distribution / selectivity; | |
With water; potassium hydrogencarbonate under 52505.3 Torr; for 3 - 4h; Conversion of starting material; | |
With water; AMBERJET 4200 exchanged with bicarbonate anions at 84 - 93℃; under 7500.75 Torr; for 127 - 2556h; not specified; Product distribution / selectivity; Continuous process; |
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; |
Diethylene glycol, also known as 2,2'-oxybisethanol, is colorless, virtually odorless, viscous, hygroscopic liquid with a sweetish taste. It has a higher boiling point, viscosity and specific gravity compared to MEG. It is miscible with water, ethanol, ethylene glycol, acetone, chloroform, and furfural, but not miscible with ether, carbon tetrachloride, carbon disulfide, straight-chain aliphatic hydrocarbons, or aromatic hydrocarbons. Diethylene glycol is an important industrial solvent. It is utilized in the manufacture of unsaturated polyesters, plasticizer and some important resins.
Diethylene glycol is one kind of glycols derived from oxirane. These glycols have the formula HOCH2CH2(OCH2CH2)nOH are:
n = 0 ethylene glycol; MEG
n = 1 DEG
n = 2 triethylene glycol, TEG, or triglycol
n = 3 tetraethylene glycol
n = 4 pentaethylene glycol
n > 4 polyethylene glycol
Preparation: Diethylene glycol is produced as a by-product, along with triethylene glycol, in the manufacture of ethylene glycol from hydrolysis of ethylene oxide. The industry generally operates to maximize MEG production. Availability of DEG will depend on demand for derivatives of the primary product, ethylene glycol, rather than on DEG market requirements.
Uses: Diethylene glycol is used to produce unsaturated polyester resins, plasticizers, polyurethanes, rubber, fiberglass, oil viscosity improver, and so on. It is also used as antifreeze, gas dehydration, plasticizer, solvent, aromatics extraction agent, cigarette hygroscopic agent, textile lubricant and finishing agent, antidesiccant of paste and a variety of glue, etc. What's more, it is used as solvent for oil, resins, nitrocellulose, printing ink, dyes and other organic compounds. Although a dilute solution of diethylene glycol can also be used as a coolant, ethylene glycol is much more commonly used.
Safty: Firstly, diethylene glycol is irritant, and may cause inflammation to the skin or other mucous membranes. Then, it is harmful and may cause damage to health. Besides, it is toxic and may at low levels cause damage to health. And it could even cause heritable genetic damage. Therefore, if swallowed, seek medical advice immediately and show this container or label. Despite the discovery of diethylene glycol's toxicity in 1937 and its involvement in mass poisonings around the world, it also has caused many deaths in different countries. In China, it was also used as a component of cheap toothpaste and winemakers as an adulterant to create a "sweet" wine. Besides China, there also many countries has been damaged by diethylene glycol. Such as: 1937-The Massengill Incident (United States), 1969–South Africa, 1985-Spain, 1985-Wine Scandal, 1986–India, 1990-Nigeria, 1990-1992-Bangladesh, 1992-Argentina, 1995-1996-Haiti, 2006-China, 2006-Panama, 2007-Worldwide toothpaste incident, and 2008 - Nigeria.
Other properties: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 3.58; (4)ACD/KOC (pH 7.4): 3.58; (5)#H bond acceptors: 3; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 6; (8)Polar Surface Area: 49.69; (9)Index of Refraction: 1.442; (10)Molar Refractivity: 25.39 cm3; (11)Molar Volume: 95.9 cm3; (12)Polarizability: 10.06 ×10-24 cm3; (13)Surface Tension: 42.1 dyne/cm; (14)Density: 1.106 g/cm3; (15)Flash Point: 143.3 °C; (16)Enthalpy of Vaporization: 56.1 kJ/mol; (17)Boiling Point: 245.7 °C at 760 mmHg; (18)Vapour Pressure: 0.00469 mmHg at 25°C; (19)Exact Mass: 106.062994; (20)MonoIsotopic Mass: 106.062994; (21)Topological Polar Surface Area: 49.7; (22)Heavy Atom Count:7; (23)Formal Charge: 0; (24)Complexity: 26.1.
Structure Descriptors:
1. Smiles:O(CCO)CCO
2. InChI:InChI=1/C4H10O3/c5-1-3-7-4-2-6/h5-6H,1-4H2
Toxicity:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | oral | 3300mg/kg (3300mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 21, Pg. 173, 1939. | |
child | TDLo | oral | 2400mg/kg (2400mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: OTHER CHANGES | Journal of Pediatrics. Vol. 109, Pg. 731, 1986. |
dog | LD50 | oral | 9gm/kg (9000mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 67, Pg. 101, 1939. | |
guinea pig | LD50 | oral | 7800mg/kg (7800mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: MUSCLE WEAKNESS LIVER: OTHER CHANGES | Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 4, Pg. 142, 1945. |
guinea pig | LD50 | unreported | 14gm/kg (14000mg/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. |
human | LDLo | oral | 1gm/kg (1000mg/kg) | Journal of Industrial Hygiene and Toxicology. Vol. 21, Pg. 173, 1939. | |
mouse | LCLo | inhalation | 130mg/m3/2H (130mg/m3) | BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: CYANOSIS BEHAVIORAL: EXCITEMENT | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 10(12), Pg. 30, 1966. |
mouse | LD50 | intraperitoneal | 9719mg/kg (9719mg/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 | oral | 23700mg/kg (23700mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: MUSCLE WEAKNESS LIVER: OTHER CHANGES | Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 4, Pg. 142, 1945. |
mouse | LD50 | unreported | 13300mg/kg (13300mg/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. |
mouse | LDLo | subcutaneous | 5gm/kg (5000mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 42, Pg. 355, 1931. | |
rabbit | LD50 | oral | 4400mg/kg (4400mg/kg) | BEHAVIORAL: COMA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Journal of Industrial Hygiene and Toxicology. Vol. 21, Pg. 173, 1939. |
rabbit | LD50 | skin | 11890mg/kg (11890mg/kg) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 25, 1974. | |
rabbit | LD50 | unreported | 2688mg/kg (2688mg/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 | 4472mg/kg (4472mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 59, Pg. 93, 1937. | |
rabbit | LDLo | intravenous | 2236mg/kg (2236mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 59, Pg. 93, 1937. | |
rat | LD50 | intraperitoneal | 7700mg/kg (7700mg/kg) | "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 3836, 1982. | |
rat | LD50 | intravenous | 6565mg/kg (6565mg/kg) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 25, 1974. | |
rat | LD50 | oral | 12565mg/kg (12565mg/kg) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 25, 1974. | |
rat | LD50 | subcutaneous | 18800mg/kg (18800mg/kg) | "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 3836, 1982. | |
rat | LD50 | unreported | 15650mg/kg (15650mg/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 | 7826mg/kg (7826mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 59, Pg. 93, 1937. |