Product
Butadienes
Segment
Chemicals
Main-Family
Unsaturated Monomers
Sub-Family
Aliphatic Olefins
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Description

Butadienes are a group of organic compounds with the molecular formula C₄H₆, characterized by the presence of two double bonds. The two main isomers of butadiene are 1,3-butadiene and 1,2-butadiene, which differ in the arrangement of their double bonds.

1,3-Butadiene

1,3-Butadiene is a conjugated diene, meaning its double bonds are separated by a single bond, allowing for resonance stabilization. Its structure is CH₂=CH−CH=CH₂. This compound is widely used in industrial applications, particularly in the production of synthetic rubbers and polymers like styrene-butadiene rubber (used in tires) and ABS plastics. It is a colorless, flammable gas with a mild aromatic odor and is thermodynamically stabilized due to conjugation effects. The most stable conformation of 1,3-butadiene is the s-trans form, where the molecule adopts a planar geometry to maximize conjugation.

1,2-Butadiene

1,2-Butadiene is an allene (a cumulated diene), meaning its two double bonds are adjacent. Its structure is CH₂=C=CH−CH₃. Unlike 1,3-butadiene, it does not exhibit resonance stabilization and has limited industrial applications. It is less stable thermodynamically and lacks the extensive use seen with 1,3-butadiene.

Comparison of Isomers

Property 1,3-Butadiene 1,2-Butadiene
Structure CH₂=CH−CH=CH₂ CH₂=C=CH−CH₃
Type of Diene Conjugated Cumulated (Allene)
Stability Thermodynamically stable Less stable
Industrial Use Synthetic rubber, plastics Limited
Conformation s-trans (most stable) No significant conformations

 

Both isomers are flammable gases and must be handled carefully due to their explosive potential when mixed with air.

Reference

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Molecular representation of 1,2-butadiene (left hand) and 1,3-butadiene (right hand)
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Unit of Measure
Metric Ton
Physical State

Gas

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Modified by UserPic  Kokel, Nicolas 2/8/2025 2:31 PM
Added 2/15/2021 11:24 PM
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