1,4-Butynediol

1,4-Butynediol[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
But-2-yne-1,4-diol
Other names
Butynediol
2-Butyne-1,4-diol
1,4-Dihydroxy-2-butyne
Identifiers
110-65-6 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:16413 YesY
ChemSpider 7775 YesY
ECHA InfoCard 100.003.445
KEGG C02497 YesY
Properties
C4H6O2
Molar mass 86.09 g·mol−1
Appearance Colorless crystalline solid[2]
Density 1.11 g/cm3 (at 20 °C)[2]
Melting point 58 °C (136 °F; 331 K)[2]
Boiling point 238 °C (460 °F; 511 K)[2]
3740 g/L[2]
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Flash point ~136 °C (277 °F)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

1,4-Butynediol is an organic compound that is an alkyne and a diol. It is a colourless, hygroscopic solid that is soluble in water and polar organic solvents. It is a commercially significant compound in its own right and as a precursor to other products.

Synthesis

1,4-Butynediol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants:[3]

2 CH2O + HC≡CH → 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.[4]

Applications

1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes. It is the major raw material used in the synthesis of vitamin B6.[5] It is also used for brightening, preserving, and inhibiting nickel plating.[3]

It reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO2CC(Cl)=C(Cl)CHO (see mucobromic acid).

Safety

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

References

  1. ↑ 1,4-Butynediol at chemicalland21.com
  2. 1 2 3 4 5 6 Record in the GESTIS Substance Database of the IFA
  3. 1 2 Heinz Gräfje, Wolfgang Körnig, Hans-Martin Weitz, Wolfgang Reiß, Guido Steffan, Herbert Diehl, Horst Bosche, Kurt Schneider and Heinz Kieczka Butanediols, Butenediol, and Butynediol" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a04_455
  4. ↑ 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.
  5. ↑ 1,4-Butynediol at Sanwei
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