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Diethylene glycol

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Name

Diethylene glycol

EINECS 203-872-2
CAS No. 111-46-6 Density 1.106 g/cm3
PSA 49.69000 LogP -1.01240
Solubility miscible with water Melting Point -10 °C(lit.)
Formula C4H10O3 Boiling Point 245.689 °C at 760 mmHg
Molecular Weight 106.122 Flash Point 143.333 °C
Transport Information N/A Appearance colorless liquid
Safety 46 Risk Codes 22
Molecular Structure Molecular Structure of 111-46-6 (Diethylene glycol) Hazard Symbols HarmfulXn,ToxicT,IrritantXi
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;

Article Data 75

Diethylene glycol Synthetic route

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

2-({2-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-dimethyl-silanyl)-2-methyl-propane

111-46-6

diethylene glycol

Conditions
ConditionsYield
With 1,11-bis(3-methyl-3H-imidazolium-1-yl)-3,6,9-trioxaundecane di(methanesulfonate) In methanol at 20℃; for 1.5h;91%
96-49-1

[1,3]-dioxolan-2-one

67-56-1

methanol

A

109-86-4

2-methoxy-ethanol

B

107-21-1

ethylene glycol

C

616-38-6

carbonic acid dimethyl ester

D

111-46-6

diethylene glycol

Conditions
ConditionsYield
at 76.7 - 79.6℃; under 757.576 Torr; Product distribution / selectivity; Industry scale;A n/a
B 72%
C 72%
D n/a
107-21-1

ethylene glycol

A

123-91-1

1,4-dioxane

B

111-46-6

diethylene glycol

Conditions
ConditionsYield
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;
107-21-1

ethylene glycol

A

497-26-7

2-methyl-1,3-dioxolane

B

123-91-1

1,4-dioxane

C

75-07-0

acetaldehyde

D

111-46-6

diethylene glycol

Conditions
ConditionsYield
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
75-21-8

oxirane

107-21-1

ethylene glycol

111-46-6

diethylene glycol

Conditions
ConditionsYield
at 130 - 210℃; unter Druck, 16 Mol Aethylenoxyd;
With sulfuric acid
at 90 - 210℃; unter Druck;
at 100℃;
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

A

107-21-1

ethylene glycol

B

111-46-6

diethylene glycol

Conditions
ConditionsYield
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;
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;

Diethylene glycol Consensus Reports

DIETHYLENE GLYCOL(111-46-6) is reported in EPA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.

Diethylene glycol Standards and Recommendations

DFG MAK: 10 ppm

Diethylene glycol Specification

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.

Diethylene glycol is produced  from hydrolysis of ethylene oxide

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.

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