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1,4-Butynediol

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1,4-Butynediol
1,4-Butynediol
Names
IUPAC name But-2-yne-1,4-diol
Other names Butynediol
2-Butyne-1,4-diol
1,4-Dihydroxy-2-butyne
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.003.445 Edit this at Wikidata
KEGG
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2Key: DLDJFQGPPSQZKI-UHFFFAOYSA-N
  • InChI=1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2Key: DLDJFQGPPSQZKI-UHFFFAOYAT
SMILES
  • OCC#CCO
Properties
Chemical 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 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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. It is the major raw material of vitamin B6. It is also used for brightening, preserving, and inhibiting nickel plating.

Safety

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

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Hazardous Substance Fact Sheet for 1,4-butynediol
  4. 1,4-Butynediol at Sanwei
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