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.
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| Names | |
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| 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)
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.445 |
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PubChem CID
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| UNII | |
| UN number | 2716 |
CompTox Dashboard (EPA)
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| 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: | |
   
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| 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) | |
| 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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Synthesis
edit1,4-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
edit1,4-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
edit1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.
See also
edit- Acetylenedicarboxylic acid (but-2-ynedioic acid, 2-butynedioic acid)
- cis-Butene-1,4-diol
- 2-Butyne (but-2-yne)
References
edit- ^ 1,4-Butynediol at chemicalland21.com
- ^ a b c d e f Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2000). "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_455. ISBN 978-3527306732.
- ^ 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.
- ^ "1,4-Butynediol at Sanwei". Archived from the original on 2010-12-04. Retrieved 2006-11-11.