1,4-Butynediol is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
that is an
alkyne
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Acetylene
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Propyne
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1-Butyne
In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and n ...
and a
diol
A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol may also be called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. They are used as protecting gro ...
. It is a colourless, hygroscopic solid that is soluble in water and polar
organic solvent
A solvent (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for p ...
s. 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
Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
and
acetylene
Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...
are the reactants:
:2 CH
2O + HC≡CH → HOCH
2CCCH
2OH
Several patented production methods use
copper
Copper is a chemical element; it has symbol Cu (from Latin ) and atomic number 29. It is a soft, malleable, and ductile metal with very high thermal and electrical conductivity. A freshly exposed surface of pure copper has a pinkish-orang ...
bismuth
Bismuth is a chemical element; it has symbol Bi and atomic number 83. It is a post-transition metal and one of the pnictogens, with chemical properties resembling its lighter group 15 siblings arsenic and antimony. Elemental bismuth occurs nat ...
catalyst
Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...
s 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 and
2-butene-1,4-diol by
hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and
polyurethane
Polyurethane (; often abbreviated PUR and PU) is a class of polymers composed of organic chemistry, organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane term ...
s. It is the major raw material used in the synthesis of
vitamin B6.
It is also used for brightening, preserving, and inhibiting nickel plating.
It reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO
2CC(Cl)=C(Cl)CHO (see
mucobromic acid
Mucobromic acid is an organic compound that consists of a dibrominated alkene with aldehyde and carboxylic acid functional groups. It easily tautomerizes to a furanone hemiacetal form. This compound, and the analogous mucochloric acid (CAS #87-56-9 ...
).
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
{{DEFAULTSORT:Butynediol14
Alkyne derivatives
Diols