1,4-Butynediol

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.

1,4-Butynediol[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
But-2-yne-1,4-diol
Other names
Butynediol
2-Butyne-1,4-diol
1,4-Dihydroxy-2-butyne
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.445
EC Number
  • 203-788-6
KEGG
RTECS number
  • ES0525000
UNII
UN number 2716
  • InChI=1S/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2 checkY
    Key: DLDJFQGPPSQZKI-UHFFFAOYSA-N checkY
  • InChI=1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2
    Key: DLDJFQGPPSQZKI-UHFFFAOYAT
  • OCC#CCO
Properties
C4H6O2
Molar mass 86.090 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
GHS labelling:
GHS05: Corrosive GHS06: Toxic GHS07: Exclamation mark GHS08: Health hazard
Danger
H301, H312, H314, H317, H331, H373
P260, P261, P264, P270, P271, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P333+P313, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
1
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).
checkY verify (what is checkY☒N ?)
Infobox references

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.

See also

References
  1. 1,4-Butynediol at chemicalland21.com
  2. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  3. Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 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". Archived from the original on 2010-12-04. Retrieved 2006-11-11.
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