Diethylene glycol divinyl ether Property

Melting point:

-21°C

Boiling point:

198-199 °C (lit.)

Density 

0.968 g/mL at 25 °C (lit.)

vapor pressure 

17Pa at 20℃

refractive index 

n20/D 1.446(lit.)

Flash point:

160 °F

storage temp. 

Store below +30°C.

form 

clear liquid

color 

Colorless to Almost colorless

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

BRN 

1752316

InChIKey

SAMJGBVVQUEMGC-UHFFFAOYSA-N

LogP

1.8 at 23℃

CAS DataBase Reference

764-99-8(CAS DataBase Reference)

NIST Chemistry Reference

Ethene, 1,1'-[oxybis(2,1-ethanediyloxy)]bis-(764-99-8)

EPA Substance Registry System

Ethene, 1,1'-[oxybis(2,1-ethanediyloxy)]bis- (764-99-8)

Safety

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

KN3850000

TSCA 

Yes

HS Code 

2909 19 90

Toxicity

LD50 oral in rat: 3730mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H303May be harmfulif swallowed

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

Diethylene glycol divinyl ether Chemical Properties,Usage,Production

Chemical Properties

diethylene glycol divinyl ether is monomeric in character and is used as a chemical intermediate or as a crosslinking agent. Addition of isocyanic acid produces secondary diisocyanates. Divinyl ethers hydrolyze to the glycol and acetaldehyde. Chlorine or bromine add to the double bonds. Reaction with an alcohol in the presence of water produces a diacetal. Polymerization of divinyl ether of diethylene glycol with acidic catalysts produce crosslinked gels. Unsaturated polyesters, crosslinked with styrene, have been made noncorrosive to metals through use of divinyl ethers to reduce hydroxyl ond acid numbers.

Chemical Properties

Diethylene glycol divinyl ether (DEGDVE) is a colorless and transparent liquid with a boiling point of 198 °C under atmospheric pressure. It is miscible with alcohol, ether, ester and aromatic hydrocarbon, but only slightly soluble in water. Both DEGMVE and DEGDVE are chemical active and easy to be polymerized, and a small amount of NaOH is often added as a polymerization inhibitor.

Uses

Diethylene glycol divinyl ether is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Application

Diethylene glycol divinyl ether (DEGDVE) has attracted much attention due to the homopolymerization and structural diversity of copolymerization products, and it is often used as a cross-linking agent in various functional materials. Hydrogels are hydrophilic network polymers that absorb large amounts of water but are insoluble in water. The properties of high water content and insolubility in water make the materials widely used in biomedical fields such as drug delivery systems, biosensors, contact lenses, catheters, and wound dressings. Using DEGDVE as a cross-linking agent and 60Co as γ-radiation light source, hydrogels were prepared by radiation copolymerization of hydrophilic ethylene glycol monovinyl ether, hydrophobic BVE, and acidic acrylic acid. The resulting hydrogels were pH- and temperature-sensitive functional materials.
Using DEGDVE as a cross-linking agent, 2-acrylamido-2-methylpropanesulfonic acid and sodium styrene sulfonate as monomers, a plugging agent with high-temperature resistance and salt resistance was synthesized by emulsion polymerization, which has practical significance in solving the problem of water production in oil wells and plays a vital role in improving oil recovery ratio.
A three-dimensional substance with a special space structure can be synthesized by cross-linking copolymerization with DEGDVE and used as a modified substrate material. For example, cross-linking copolymerization of methyl vinyl sulfide with DEGDVE gave a solid polymer with a crown structure, which was modified and used as active matrices of solid superbases for ethynylation of acetone and vinylation of diethylene glycol or ethylene glycol.

Flammability and Explosibility

Non flammable

Synthesis

Acetylene reacts with diethylene glycol in the presence of a catalyst such as potassium hydroxide or potassium diethylene glycol to yield DEGMVE and Diethylene glycol divinyl ether (DEGDVE):