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Divinylbenzene
Divinylbenzene
Divinylbenzene
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Divinylbenzene
Skeletal formulae of both isomers
Skeletal formulae of both isomers
Ball-and-stick model of m-Divinylbenzene
Ball-and-stick model of m-Divinylbenzene
Ball-and-stick model of p-Divinylbenzene
Ball-and-stick model of p-Divinylbenzene
Names
Other names
Diethylene benzene, DVB, Vinylstyrene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.932 Edit this at Wikidata
EC Number
  • 215-325-5
  • m-: 203-595-7
  • p-: 203-266-8
RTECS number
  • CZ9370000
  • m-: CZ9450000
UNII
UN number 3532 3534
  • p-: InChI=1S/C10H10/c1-3-9-5-7-10(4-2)8-6-9/h3-8H,1-2H2
    Key: WEERVPDNCOGWJF-UHFFFAOYSA-N
  • C=CC1=CC=CC=C1C=C
  • m-: C=CC1=CC(=CC=C1)C=C
  • p-: C=CC1=CC=C(C=C1)C=C
Properties
C10H10
Molar mass 130.190 g·mol−1
Appearance pale, straw-colored liquid[1]
Density 0.914 g/mL
Melting point −66.9 to −52 °C (−88.4 to −61.6 °F; 206.2 to 221.2 K)
Boiling point 195 °C (383 °F; 468 K)
0.005% (20°C)[1]
Solubility in other solvents Soluble in ethanol and ether
Vapor pressure 0.7 mmHg (20°C)[1]
Hazards
Flash point 76 °C (169 °F; 349 K)
Explosive limits 1.1%-6.2%[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 TWA 10 ppm (50 mg/m3)[1]
IDLH (Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Divinylbenzene (DVB) is an organic compound with the chemical formula C6H4(CH=CH2)2 and structure H2C=CH−C6H4−HC=CH2 (a benzene ring with two vinyl groups as substituents). It is related to styrene (vinylbenzene, C6H5−CH=CH2) by the addition of a second vinyl group.[2] It is a colorless liquid manufactured by the thermal dehydrogenation of isomeric diethylbenzenes. Under synthesis conditions, o-divinylbenzene converts to naphthalene and thus is not a component of the usual mixtures of DVB.[3]

Production and use

[edit]

It is produced by dehydrogenation of diethylbenzene:

C6H4(C2H5)2 → C6H4(C2H3)2 + 2 H2

Divinylbenzene is usually encountered as a 2:1 mixture of m- and p-divinylbenzene, containing also the corresponding isomers of ethylvinylbenzene.

Styrene and divinylbenzene react to form the copolymer styrene-divinylbenzene, S-DVB or Sty-DVB. The resulting cross-linked polymer is mainly used for the production of ion exchange resin and Merrifield resins for peptide synthesis.[3]

Nomenclature

[edit]
  • Ortho: variously known as 1,2-diethenylbenzene, 1,2-divinylbenzene, o-vinylstyrene, o-divinylbenzene
  • Meta: known as 1,3-diethenylbenzene, 1,3-divinylbenzene, m-vinylstyrene, m-divinylbenzene
  • Para: known as 1,4-diethenylbenzene, 1,4-divinylbenzene, p-vinylstyrene, p-divinylbenzene.

These compounds are systematically called diethenylbenzene, although this nomenclature is rarely encountered.

References

[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Divinylbenzene

View on Grokipedia
from Grokipedia
Divinylbenzene (DVB) is an organic compound with the molecular formula C₁₀H₁₀, featuring a benzene ring substituted with two vinyl groups (-CH=CH₂), typically as a mixture of meta- and para-isomers in commercial forms. It appears as a colorless to pale yellow liquid with a density of 0.919 g/mL at 20°C, a boiling point of 195°C, and a melting point of -87.1°C. This versatile monomer is essential in polymer chemistry, primarily serving as a cross-linking agent to enhance the structural integrity and thermal stability of resins. In industrial applications, DVB is copolymerized with styrene to form polystyrene-divinylbenzene (PS-DVB) resins, which are crucial for ion-exchange materials, chromatographic packings, and adsorbents used in and chemical separations. Its high reactivity allows for the creation of rigid, porous networks that resist swelling and maintain functionality under harsh conditions. Beyond resins, DVB contributes to the synthesis of synthetic rubbers, adhesives, and like battery components. Commercially, DVB is produced through the catalytic dehydrogenation of diethylbenzene (DEB) in a two-step process: first to ethylvinylbenzene, then to DVB, often facilitated by to shift equilibrium and prevent catalyst . Iron-based s are employed in packed-bed reactors at temperatures around 600°C and , yielding products stabilized with inhibitors like tert-butylcatechol to control during storage. Global production focuses on high-purity grades (e.g., 55% or 80% DVB content), meeting demands from the growing and resin markets.

Structure and nomenclature

Molecular structure

Divinylbenzene has the molecular formula \ceC10H10\ce{C10H10}. It features a central ring with two vinyl substituents (\ce−CH=CH2\ce{-CH=CH2}) attached to the ring carbons, represented by the structural formula \ceC6H4(CH=CH2)2\ce{C6H4(CH=CH2)2}. The molecular is often depicted using a , showing the ring as a with three alternating s and the vinyl groups as linear chains extending from the ring, each containing a terminal carbon-carbon . This highlights the six π\pi electrons in the aromatic ring and the additional π\pi bonds in the vinyl moieties. All carbon atoms in the ring and vinyl groups exhibit sp2sp^2 hybridization, leading to planar geometry with bond angles of approximately 120° throughout the . The aromatic C–C bond lengths in the ring are about 1.39 , while the vinyl C=C bonds are typically around 1.34 . The vinyl groups are conjugated with the ring's π\pi system, enabling delocalization of π\pi electrons across the entire framework, which increases on the vinyl carbons and enhances the molecule's reactivity in reactions.

Isomers

Divinylbenzene exists in three positional : 1,2-divinylbenzene (ortho), 1,3-divinylbenzene (meta), and 1,4-divinylbenzene (para), distinguished by the relative positions of the two ethenyl (-CH=CH₂) groups on the ring—adjacent carbons for ortho, separated by one carbon for meta, and opposite carbons for para. The ortho isomer exhibits the lowest stability among the three, primarily due to steric hindrance between the proximate vinyl groups, which promotes rapid intramolecular cyclization to form under typical production or reaction conditions. In contrast, the meta and para isomers are more stable and dominate commercial formulations, typically in a meta-to-para ratio of approximately 2:1, reflecting the distribution inherited from the precursor diethylbenzene isomers (with ortho comprising only about 4%). Commercial divinylbenzene mixtures, often at 50-55% purity, include significant impurities of ethylvinylbenzene isomers (also known as ethenyl ethylbenzenes), which are structurally analogous but possess one ethyl (-CH₂CH₃) and one on the ring, resulting from incomplete dehydrogenation of diethylbenzene precursors. These impurities, predominantly the meta and para variants, constitute roughly 45% of the technical-grade product and can influence behavior. The positional isomers are readily distinguished by spectroscopic methods, particularly ¹H NMR, where the chemical shifts and coupling patterns of the vinyl protons vary distinctly: for instance, the methylene protons appear at τ 4.74 and 4.47 for ortho, τ 4.85 and 4.68 for meta, and τ 4.90 and 4.72 for para (on the 60-Mc. scale), allowing clear identification of each in mixtures.

Naming conventions

Divinylbenzene is systematically named according to IUPAC recommendations as 1,3-diethenylbenzene for the meta isomer (m-DVB) and 1,4-diethenylbenzene for the para isomer (p-DVB), reflecting the positions of the ethenyl (vinyl) groups on the ring. Alternatively, these may be expressed as 1,3-bis(ethenyl)benzene and 1,4-bis(ethenyl)benzene, emphasizing the two identical substituents. The trivial name "divinylbenzene" (DVB) remains widely used in chemical and polymer contexts, with abbreviations m-DVB and p-DVB specifying the meta and para positional isomers. These abbreviations originated in early polymer research and are standard in literature discussing cross-linking agents. The nomenclature evolved from early 20th-century polymer literature, where divinylbenzene was first described as a cross-linking monomer in the 1930s; notably, Hermann Staudinger reported its copolymerization with styrene in 1934, establishing its role in network polymer formation and solidifying the "divinylbenzene" designation. Commercially, divinylbenzene is designated as technical-grade mixtures, typically containing 50–80% alongside ethylvinylbenzene (EVB) and minor impurities like diethylbenzene, with purity levels such as "55% " or "80% " indicating the active content for industrial applications.

Properties

Physical properties

Divinylbenzene, typically encountered as a commercial mixture of meta- and para-isomers, appears as a colorless to pale yellow liquid. Its density is 0.919 g/mL at 20 °C. The melting point of the mixture ranges from -66.9 °C to -52 °C. The boiling point is 195 °C at 760 mmHg. Divinylbenzene is insoluble in water (solubility <0.005% at 20 °C) but miscible with organic solvents such as ethanol, ether, and acetone. The refractive index is 1.561 (n_D^{20}). Its vapor pressure is 0.9 mmHg at 30 °C. Properties vary with isomer purity; for example, the para-isomer (p-DVB) has a boiling point of approximately 200 °C at 760 mmHg.

Chemical properties

Divinylbenzene is highly reactive due to its two vinyl groups attached to the benzene ring, enabling it to undergo polymerization through free radical, cationic, or anionic mechanisms. The free radical pathway is the most common industrial process, initiated by peroxides or azo compounds, while anionic polymerization can produce well-defined structures under living conditions using organolithium initiators. Cationic polymerization occurs with Lewis acids like BF₃, though it is less frequently employed due to side reactions. To prevent unintended polymerization during storage, commercial divinylbenzene is stabilized with approximately 1000 ppm of tert-butylcatechol, an antioxidant inhibitor that scavenges free radicals. The vinyl double bonds in divinylbenzene are susceptible to electrophilic addition reactions, such as halogenation or hydrohalogenation, similar to other alkenes. These bonds also serve as dienophiles in Diels-Alder cycloadditions with conjugated dienes, facilitated by the electron-withdrawing effect of the aromatic ring. The conjugation between the vinyl groups and the benzene ring enhances the overall reactivity by stabilizing transition states and lowering the activation energy for these additions. Divinylbenzene exhibits good thermal stability up to approximately 150°C under inert conditions, but it readily undergoes exothermic polymerization at higher temperatures, potentially leading to pressure buildup or explosions. It is sensitive to light and oxygen, which can initiate radical formation and promote polymerization, necessitating storage in cool, dark, and oxygen-limited environments. As a non-polar aromatic hydrocarbon lacking functional groups capable of proton donation or acceptance, divinylbenzene is chemically neutral with no significant acid-base properties. Its insolubility in water and miscibility with organic solvents underscore its hydrophobic, non-polar nature.

Production

Industrial production

Divinylbenzene is produced on an industrial scale primarily through the catalytic dehydrogenation of diethylbenzene, a process that occurs in the presence of steam over iron oxide-based catalysts at temperatures ranging from 600°C to 650°C. The reaction follows the stoichiometry C₆H₄(C₂H₅)₂ → C₆H₄(CH=CH₂)₂ + 2H₂, with a steam-to-diethylbenzene weight ratio of 5 to 8 to facilitate heat transfer and suppress side reactions such as coke formation on the catalyst. This endothermic reaction is typically conducted at atmospheric pressure in fixed-bed reactors, achieving diethylbenzene conversions of 79-80% and divinylbenzene selectivity of at least 40% by weight. The feedstock, diethylbenzene, is derived from the sequential Friedel-Crafts alkylation of benzene with ethylene: first to ethylbenzene, then to diethylbenzene using acidic catalysts like aluminum chloride or zeolite-based systems. The dehydrogenation effluent, a gaseous mixture containing divinylbenzene, hydrogen, unreacted diethylbenzene, ethylvinylbenzene (also known as ethylstyrene), and water vapor, is cooled and condensed for subsequent purification. Purification involves fractional distillation under vacuum to separate divinylbenzene from ethylvinylbenzene and other byproducts, with polymerization inhibitors added to prevent premature crosslinking during the high-temperature separation. Overall process yields reach 80-90%, resulting in commercial grades of divinylbenzene with 50-80% purity, typically as a mixture of meta- and para-isomers (approximately 2:1 ratio) stabilized against polymerization. These grades are supplied in inhibited forms to maintain stability during storage and transport. Major producers include Deltech Holdings, Dow Chemical Company, Nippon Steel Chemical & Material Co., Ltd., Mitsubishi Chemical Corporation, and Jiangsu Evergreen Environmental Protection Co., Ltd., which collectively dominate the market. As of 2024, Dow expanded its U.S. production capacity by 15,000 tons annually to meet rising demand, contributing to a global output estimated at around 50,000 tons per year.

Laboratory synthesis

Divinylbenzene can be prepared in the laboratory through acid-catalyzed dehydration of bis(1-hydroxyethyl)benzene isomers, where the secondary alcohol groups are converted to vinyl groups by elimination of water. This method is suitable for small-scale production and pure isomer isolation, using acids such as phosphoric acid or strong acid cation exchange resins. For instance, 1,4-bis(1-hydroxyethyl)benzene is dehydrated in the presence of a styrene-sulfonic acid resin catalyst like Amberlyst 15, typically in an inert solvent such as acetone, at temperatures of 20–100°C under atmospheric pressure, achieving high selectivity (up to 88%) toward the divinyl product. The use of phosphoric acid follows analogous procedures established for the dehydration of 1-phenylethanol to , involving heating the diol with the acid catalyst at 100–150°C to promote E1 or E2 elimination mechanisms. Yields for the meta- and para-divinylbenzene isomers generally range from 60–80%, reflecting efficient conversion under controlled conditions. An alternative route employs base-promoted elimination reactions from dihalogenated precursors, such as 1,4-bis(1-chloroethyl) or 1,4-bis(1-bromoethyl)benzene, to generate the divinyl structure via double dehydrohalogenation. A strong, hindered base like potassium tert-butoxide is added to the dihalide in tetrahydrofuran (THF) at 0–60°C, facilitating selective E2 elimination to minimize side reactions and yield the target compound. This approach is particularly useful for preparing specific isomers, though the ortho isomer exhibits instability due to its propensity for intramolecular cyclization to form bicyclic structures. Following synthesis, the crude divinylbenzene mixture, which often contains ethylvinylbenzene byproducts and unreacted precursors, is purified by vacuum distillation at reduced pressure (typically 10–20 mmHg) to isolate the monomer while preventing thermal polymerization. For separation of the ortho, meta, and para isomers, high-performance liquid chromatography (HPLC) using iron-based metal-organic frameworks like MIL-53(Fe) or MIL-100(Fe) as stationary phases provides baseline resolution, enabling collection of pure fractions in analytical or preparative scales. Gas chromatography with specialized columns, such as those coated with liquid crystals, offers an additional option for isomer analysis and isolation. These techniques ensure high-purity divinylbenzene (>95%) for research applications, adapting principles from industrial dehydrogenation processes of diethylbenzene.

Applications

Cross-linking in polymers

Divinylbenzene (DVB) primarily functions as a cross-linking agent in the free-radical of styrene, yielding polystyrene-divinylbenzene (PS-DVB) copolymers that form three-dimensional network structures essential for various applications. These copolymers are typically synthesized with DVB concentrations ranging from 1% to 20% by weight relative to styrene, where even low levels (e.g., 1-3%) introduce sufficient cross-links to impart structural integrity beyond linear . The cross-linking mechanism relies on the bifunctional vinyl groups of DVB, which participate in the alongside styrene monomers. During the process, one vinyl group of a DVB molecule bonds to a growing chain, while the second vinyl group later reacts with another chain or pending radical, forming covalent bridges that connect multiple strands. This network formation enhances the mechanical rigidity, thermal stability, and resistance to solvents and swelling compared to uncross-linked . In the production of ion-exchange resins, PS-DVB copolymers serve as the base matrix, which is subsequently modified by sulfonation to introduce groups for cation-exchange capabilities or amination for quaternary ammonium groups in anion-exchange resins, enabling selective removal in processes. These resins are manufactured as uniform spherical beads with diameters of 0.3-1.2 mm to optimize flow dynamics and exchange efficiency in packed columns. The degree of cross-linking profoundly affects the polymer's microstructure and performance, with cross-link density often expressed as the molar ratio of DVB to styrene units, ν=nDVBnstyrene\nu = \frac{n_{\text{DVB}}}{n_{\text{styrene}}}, where nn denotes moles. At low ν\nu (e.g., 0.01-0.02), the network remains flexible and swellable, facilitating diffusion; higher ν\nu (e.g., >0.05) yields denser, gel-like structures with reduced and swelling but increased mechanical strength and .

Other uses

Divinylbenzene acts as a crosslinking comonomer in the synthesis of rubber (SBR), contributing to improved elasticity and mechanical properties essential for production. By incorporating small amounts of divinylbenzene during , the resulting terpolymers exhibit enhanced tensile strength and resilience, making them suitable for high-performance automotive s where durability under stress is critical. In , copolymers of divinylbenzene and styrene form rigid macroporous stationary phases for (HPLC) columns, valued for their superior mechanical stability under high pressure and temperature conditions. These poly(styrene-divinylbenzene) materials enable efficient separation of complex mixtures, such as biomolecules and polymers, due to their tunable and chemical inertness, with applications in pharmaceutical and . Their robustness allows operation at elevated temperatures up to 200°C, outperforming traditional silica-based phases in certain reversed-phase separations. Divinylbenzene enhances the durability of adhesives and coatings, particularly in formulations requiring robust crosslinking for improved and resistance to environmental factors. In UV-curable systems, it serves as a reactive and crosslinker, accelerating and yielding coatings with higher hardness, tensile strength, and chemical resistance, as seen in bio-based compositions. This role is prominent in industrial coatings for metal substrates and pressure-sensitive adhesives, where it minimizes shrinkage and boosts long-term performance without compromising flexibility. As of 2025, emerging applications of divinylbenzene include its integration into resins and photoresists, leveraging its rapid crosslinking for high-resolution additive manufacturing. In thiol-ene photopolymerization systems for vat photopolymerization , divinylbenzene provides storage-stable formulations that enable the creation of complex, mechanically robust structures with minimal distortion. For photoresists, divinylbenzene-resorcinol resins offer sensitivity to UV or electron beam exposure, facilitating precise patterning in and advanced processes. These developments highlight divinylbenzene's versatility in next-generation materials for and biomedical devices.

Safety and handling

Hazards and toxicity

Divinylbenzene is a , eye, and irritant, and may cause allergic reactions upon repeated exposure. The acute oral LD50 in rats is approximately 4,000–4,600 mg/kg, indicating relatively low by this route. There is equivocal evidence of carcinogenicity from NTP studies, with potential metabolic activation by enzymes to form intermediates similar to those from styrene. As a combustible liquid, divinylbenzene has a of approximately 70 °C and an around 500 °C. Its vapors are heavier than air and can form explosive mixtures with air when heated, posing a and hazard in enclosed spaces. Divinylbenzene exhibits low water solubility (approximately 20–50 mg/L at 25 °C) but is toxic to aquatic organisms, with 96-hour LC50 values for such as Japanese medaka (Oryzias latipes) approximately 4.2 mg/L; it is classified as toxic to aquatic life with long-lasting effects under regulations. potential is moderate, with a BCF of 206–444 and log Kow of about 3.8–4.2. Regulatory limits include an OSHA (PEL) of 10 ppm as an 8-hour time-weighted average, and under REACH, it is classified as a skin sensitizer (H317).

Storage and polymerization control

Divinylbenzene requires careful storage to maintain stability and prevent unintended . It should be kept in a cool, dark, well-ventilated area at temperatures below 25°C, ideally 2–8°C, in tightly closed containers made of compatible materials such as amber glass or mild drums to minimize exposure to light and air. is recommended, particularly in warmer climates, to extend usability. Commercial divinylbenzene is typically stabilized with inhibitors like 4-tert-butylpyrocatechol (TBC) at concentrations of 10–1000 ppm to suppress free radical . Under proper conditions, including maintenance of inhibitor levels and oxygen content (minimum 15 ppm for TBC efficacy), shelf life can reach 1–2 years, though regular testing of inhibitor concentration is advised as it depletes over time. To prevent polymerization, avoid sources, direct , oxidizing agents, peroxides, strong acids, and metallic salts, as these can initiate or accelerate the reaction. Safe handling involves , including gloves, safety goggles, protective clothing, and respiratory protection if airborne concentrations exceed 10 ppm. Work in well-ventilated areas or under local exhaust to control vapors, and ground equipment to prevent static discharge. For spills, evacuate the area, eliminate ignition sources, contain the liquid with absorbent materials like or sand, and dispose of as without allowing entry into drains. In emergencies, such as runaway , cool the affected containers externally with water spray to dissipate heat without direct contact. For fires involving divinylbenzene, use dry chemical, , foam, or water spray extinguishers; avoid direct water streams on the material to prevent splattering. Poisonous gases may be released during , so firefighters should wear .

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