Divinylbenzene
[CAS# 1321-74-0]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Aromatic hydrocarbon
• Name: Divinylbenzene
• Synonyms: 1,2-bis(ethenyl)benzene
• Molecular Formula: C₁₀H₁₀
• Molecular Weight: 131.19
• CAS Registry Number: 1321-74-0
• EC Number: 215-325-5
• SMILES: C=CC1=CC=CC=C1C=C

Properties

• Solubility: 0.005% (Expl.)Density
• Melting point: -66.7 °C (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H315-H317-H319-H411
• Safety Statements: P261-P264-P273-P280-P302+P352-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Reproductive toxicity	Repr.	2	H361
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Germ cell mutagenicity	Muta.	2	H341
Specific target organ toxicity - single exposure	STOT SE	3	H336
Skin corrosion	Skin Corr.	1C	H314
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Skin sensitization	Skin Sens.	1B	H317
Reproductive toxicity	Repr.	2	H361fd

Discovery and Applications

Divinylbenzene (DVB) is an organic compound with the chemical formula C₈H₈(C₂H₃)₂. It consists of a benzene ring attached to two vinyl groups (–CH₂CH=CH₂) at different positions. DVB is a highly reactive compound and is used primarily as a cross-linking agent in the production of polymers. It is a colorless liquid that is insoluble in water but soluble in many organic solvents. DVB is typically obtained through the dehydrohalogenation of 1,2-dichlorobenzene, a process in which two chlorine atoms are replaced by vinyl groups under suitable conditions.

The discovery of divinylbenzene can be traced back to the early 20th century, although its commercial applications began to develop more prominently in the latter half of the century. Its first significant use was in the field of polymer chemistry, where it found applications as a cross-linking agent, contributing to the formation of more rigid and durable materials.

One of the primary uses of divinylbenzene is in the production of cross-linked polystyrene resins. By incorporating DVB into the polymerization process, the polymer network becomes more rigid and resistant to chemical degradation. These cross-linked polymers are widely used in the production of ion-exchange resins, which are essential in water treatment, pharmaceutical applications, and chemical processing. DVB is also employed in the creation of certain types of chromatographic supports, where its high surface area and chemical stability are beneficial for separating complex mixtures.

DVB plays an important role in the manufacture of specialty polymers, such as those used in molecular sieves and catalysts. In addition, it is used in the synthesis of certain rubbers, as it helps improve the elasticity and chemical resistance of the material. Divinylbenzene's versatility as a cross-linking agent also makes it valuable in the production of highly functionalized polymers that are tailored for specific applications in electronics, automotive, and biomedical fields.

In addition to its role in polymer science, divinylbenzene is used in the preparation of various other chemical compounds through reactions such as polymerization and copolymerization. It can also be used in the synthesis of specialty materials that require precise control over molecular structure and properties.

From an environmental and health perspective, divinylbenzene is classified as a volatile organic compound (VOC) and is subject to regulatory guidelines in many regions. Its high reactivity and potential for producing hazardous byproducts in industrial processes require careful handling. Workers involved in its production and use are advised to follow appropriate safety protocols to minimize exposure.

In conclusion, divinylbenzene is a highly reactive compound that plays a crucial role in the production of cross-linked polymers, resins, and specialty materials. Its discovery and development have significantly impacted fields such as polymer chemistry, water treatment, and chromatography. As a versatile cross-linking agent, it contributes to the creation of durable, chemically resistant materials that are used in a wide range of industrial applications.

References

2024. Removal of pyrene from domestic water supply using styrene-based imprinted polymer. Discover Environment, 2(1).
DOI: 10.1007/s44274-024-00168-5

2024. Comparative adsorption studies of modified sulfonated styrene-divinylbenzene with cross-linked DVB for multiple radionuclides removal from radioactive wastewater. International Journal of Environmental Science and Technology, 21(12).
DOI: 10.1007/s13762-024-06133-2

2024. Inhalable nanocatalytic therapeutics for viral pneumonia. Nature Materials, 23(12).
DOI: 10.1038/s41563-024-02041-5