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2-Butene-1,4-diol (C₄H₈O₂) is a diol (two hydroxyl groups) with a conjugated double bond between carbons 2 and 3. Its structure, HOCH₂–CH=CH–CH₂OH, allows for cis (Z) and trans (E) stereoisomers. A reactive compound, it undergoes addition reactions (e.g., hydrogenation to 1,4-butanediol) and esterification. Primarily used in polymer production (polyesters, polyurethanes) and as a precursor for specialty chemicals, it also shows potential in electrolytes for batteries. Soluble in water and polar solvents, it is flammable and a skin/eye irritant. Its conjugated system and dual hydroxyl groups make it valuable in materials science and organic synthesis.
2-Butene-1,4-diol is an organic compound with the molecular formula C₄H₈O₂. Below is a detailed breakdown of its properties, structure, synthesis, and applications:
IUPAC Name: (2E)-but-2-ene-1,4-diol or (2Z)-but-2-ene-1,4-diol (depending on stereochemistry).
Structure:
Example Structure:
Four-carbon chain with hydroxyl (-OH) groups on the first (C1) and fourth (C4) carbons.
A double bond between the second (C2) and third (C3) carbons.
Exists as cis (Z) or trans (E) isomers due to the double bond.
Physical State: Typically a viscous liquid or low-melting solid.
Solubility: Soluble in water and polar solvents due to hydroxyl groups.
Reactivity:
Hydroxyl groups: Participate in esterification, etherification, and oxidation.
Double bond: Undergoes addition reactions (e.g., hydrogenation to form 1,4-butanediol).
Common routes include:
Hydration of 2-Butyne: Catalyzed by acid or base to introduce hydroxyl groups.
Reduction of Maleic Acid Derivatives: Using reducing agents like sodium borohydride.
Biochemical Pathways: Some bacteria produce similar diols via fermentation.
Polymer Industry:
Monomer: For synthesizing polyesters, polyurethanes, or resins.
Crosslinker: Enhances durability in coatings/adhesives.
Organic Synthesis:
Intermediate for pharmaceuticals, agrochemicals, or specialty chemicals.
Electrolytes: Potential use in lithium-ion batteries due to its polarity.
Hazards:
Irritant to skin/eyes.
Flammable (flash point varies by isomer).
Precautions: Use PPE (gloves, goggles) and work in well-ventilated areas.
The cis (Z) and trans (E) isomers differ in:
Physical properties (melting point, solubility).
Reactivity in stereospecific reactions.
2-Butene-1,4-diol has a double bond, making it more reactive than 1,4-butanediol (a saturated diol).
A niche chemical with applications in advanced materials and green chemistry (e.g., biodegradable polymers).
For specific data (e.g., CAS number, boiling point), consult technical databases like PubChem or chemical suppliers' SDS.
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