1,4-Butynediol
<templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox HazardsTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| UN number | 2716 |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
| Appearance | Colorless crystalline solid[2] |
| Density | 1.11 g/cm3 (at 20 °C)[2] |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
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.
See also
- Acetylenedicarboxylic acid (but-2-ynedioic acid, 2-butynedioic acid)
- cis-Butene-1,4-diol
- 2-Butyne (but-2-yne)
References
- ↑ 1,4-Butynediol at chemicalland21.com
- ↑ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and HealthScript error: No such module "TemplatePar". Script error: No such module "TemplatePar".
- ↑ a b Template:Ullmann
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "citation/CS1".