Diethylene glycol divinyl ether
Synonym(s):3,6,9-Trioxaundeca-1,10-diene;Bis[2-(vinyloxy)ethyl] ether;DEGDVE;Diethylene glycol divinyl ether
- CAS NO.:764-99-8
- Empirical Formula: C8H14O3
- Molecular Weight: 158.2
- MDL number: MFCD00054610
- EINECS: 212-133-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-03-19 15:35:46
What is Diethylene glycol divinyl ether?
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.
The Uses of Diethylene glycol divinyl ether
Diethylene glycol divinyl ether is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.
What are the applications of 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):
Properties of Diethylene glycol divinyl ether
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 | n |
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 |
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 information for Diethylene glycol divinyl ether
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H227:Flammable liquids H303:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P370+P378:In case of fire: Use … for extinction. P403+P235:Store in a well-ventilated place. Keep cool. P501:Dispose of contents/container to..… |
Computed Descriptors for Diethylene glycol divinyl ether
InChIKey | SAMJGBVVQUEMGC-UHFFFAOYSA-N |
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