1,4-Butynediol

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1,4-Butynediol[1]
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IUPAC name But-2-yne-1,4-diol
Other names Butynediol
2-Butyne-1,4-diol
1,4-Dihydroxy-2-butyne
Identifiers
CAS number 110-65-6
SMILES OCC#CCO
Properties
Molecular formula C4H6O2
Molar mass 86.09 g/mol
Density 1.2 g/cm³
Melting point

52-55 °C

Boiling point

238 °C

Hazards
NFPA 704

NFPA 704.svg

1
2
0
 
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

1,4-Butynediol is an organic compound that is an alkyne and a diol. This yellow crystalline solid is soluble in water and ethanol.

Synthesis

1,4-Butynediol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants:

2 CH2O + HCCH → HOCH2CCCH2OH

Several patented production methods use copper bismuth catalysts coated on an inert material. The normal temperature range for the reaction is 90°C up to 150°C, depending on the pressure used for the reaction which can range from 1 to 20 bar.[2]

Applications

1,4-Butynediol is a precursor to 1,4-butanediol. It is also used in the manufacture of plant protection agents, pesticides, textile additives, corrosion inhibitors, platicizers, synthetic resins, and polyurethanes.[3] It is the major raw material of vitamin B6.[4] It is also used for brightening, preserving, and inhibiting nickel plating.

Safety

1,4-Butynediol is corrosive and irritates the skin and eyes.[3]

References

  1. 1,4-Butynediol at chemicalland21.com
  2. Kale S. S. , Chaudhari R. V., Ramachandran P. A. (1981). "Butynediol synthesis. A kinetic study". Industrial & Engineering Chemistry Product Research and Development. 20 (2): 309 – 315. doi:10.1021/i300002a015. 
  3. 3.0 3.1 Hazardous Substance Fact Sheet for 1,4-butynediol
  4. 1,4-Butynediol at Sanwei

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