1,4-Butynediol

1,4-Butynediol[1]
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 Y
ChemSpider 7775 Y
KEGG C02497 Y
ChEBI CHEBI:16413 Y
Jmol-3D images Image 1
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
1
2
0
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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.

Contents

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. ^ a b Hazardous Substance Fact Sheet for 1,4-butynediol
  4. ^ 1,4-Butynediol at Sanwei