2-BUTYNE-1,4-DIOL
2-Butyne-1,4-diol is a colorless to slightly yellow, hygroscopic solid that is completely soluble in water and polar organic solvents, and is used primarily as a precursor in the synthesis of 1,4-butanediol and various other chemicals.
2-Butyne-1,4-diol is commercially significant as it serves as an intermediate in the manufacture of pesticides, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes.
2-Butyne-1,4-diol is used in biological studies for its nematocidal activity and is also involved in the cycloaddition reactions for the preparation of substituted acenes and other complex molecules.
CAS Number: 110-65-6
EC Number: 203-788-6
Molecular Formula: C4H6O2
Molecular Weight: 86.09 g/mol
Synonyms: But-2-yne-1,4-diol, Butynediol, 2-Butyne-1,4-diol, 1,4-Dihydroxy-2-butyne, 2-Butyne-1,4-diol, 110-65-6, But-2-yne-1,4-diol, 1,4-Dihydroxy-2-butyne, 1,4-BUTYNEDIOL, Bis(hydroxymethyl)acetylene, 2-Butynediol, 2-Butin-1,4-diol, NSC 834, DTXSID4021921, 2-butyn-1,4-diol, 1,4-Dimethoxyacetylene, AXH202FPQM,
CHEBI:16413, NSC-834, Agrisynth B3D, DTXCID901921, 1,4-Butynediol (VAN), 1,4-Butinodiol, Butynediol-1,4, CAS-110-65-6, HSDB 2004, EINECS 203-788-6, UNII-AXH202FPQM, UN2716, BRN 1071237, AI3-61467, 2-butyne-l,4-diol, but-2-yne-1,4diol, 1,2-Dimethoxyacetylene, 1,4Dihydroxy-2-butyne, 2-butyne-1,4-di-ol, EC 203-788-6, WLN: Q2UU2Q, 1,4-BUTYNE GLYCOL, 4-01-00-02687 (Beilstein Handbook Reference), 1,2-Dihydroxydimethylacetylene, NSC834, 2-Butyne-1,4-diol, 99%, CHEMBL3187551, 1,4-BUTYNEDIOL [HSDB], Tox21_201284, Tox21_302875, MFCD00002915, AKOS000118736, UN 2716, NCGC00249014-01, NCGC00256535-01, NCGC00258836-01, 1,4-Butynediol [UN2716], B0749, NS00009569, EN300-19323, Butynediol 1,4-Butynediol 2-Butyne-1,4-diol, C02497, E78871, Q209328, J-002458, F0001-0223, InChI=1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H, 2-butyne-1,4-diol, butynediol, 1,4-dihydroxy-2-butyne, 1,4-butynediol, bis hydroxymethyl acetylene, 2-butynediol, 2-butin-1,4-diol, agrisynth b3d, unii-axh202fpqm, 1,4-butynediol van, Bis(hydroxymethyl)acetylene, But-2-yne-1,4-diol, 1,4-Butynediol, 1,4-Dihydroxy-2-butyne, 2-Butynediol, Butynediol, 2-Butin-1,4-diol, UN 2716, 1,2-Dimethoxyacetylene, NSC 834, NSC 834, 2-Butynediol 2-Butyne-1,4-diol, Bis(hydroxymethyl)acetylene, UN 2716, 1,4-Dihydroxy-2-butyne, 2-Butynediol, But-2-yne-1,4-diol, Butynediol, Bis (hydroxymethyl) acetylene, 1,2-Dimethoxyacetylene, 1,4-Butynediol, 2-Butin-1,4-diol, 2-Butyne-1,4-diol, 1,4-Butynediol, Butynediol, Bis(hydroxymethyl)acetylene, 2-Butynediol, 1,4-Dihydroxy-2-butyne, NSC 834, BYD, BOZ, But-2-yne-1,4-diol, 1,4-BUTYNEDIOL, Butynediol, 2-BUTYN-1,4-DIOL, 2-Butin-1,4-diol, Dihydroxydimethylacetylene, 2-Butynediol, agrisynthb3d,
2-Butyne-1,4-diol is a colourless, hygroscopic solid that is soluble in water and polar organic solvents.
2-Butyne-1,4-diol is a commercially significant compound in its own right and as a precursor to other products.
2-Butyne-1,4-diol is a colorless to slightly yellow solid, and is almost odorless.
2-Butyne-1,4-diol is completely soluble with water in all proportions.
2-Butyne-1,4-diol is an organic compound that is an alkyne and a diol.
2-Butyne-1,4-diol is a colourless, hygroscopic solid that is soluble in water and polar organic solvents.
2-Butyne-1,4-diol is a commercially significant compound in its own right and as a precursor to other products.
2-Butyne-1,4-diol appears as white to light-brown solid or brownish-yellow aqueous solution.
2-Butyne-1,4-diol is solid sinks and mixes with water.
2-Butyne-1,4-diol is a butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.
2-Butyne-1,4-diol is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 1 000 tonnes per annum.
2-Butyne-1,4-diol is an organic compound combinding an alkyne and a dioland is a precursor to 1,4-Butanediol.
The Boiling point of 2-Butyne-1,4-diol is at 238°C and melting point at 52-55°C.
2-Butyne-1,4-diol is hygroscopic.
2-Butyne-1,4-diol is incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong acids and strong bases.
2-Butyne-1,4-diol is a butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.
2-Butyne-1,4-diol appears as white to light-brown solid or brownish-yellow aqueous solution.
2-Butyne-1,4-diol is water soluble.
2-Butyne-1,4-diol is an organic compound that is an alkyne and a diol.
This yellow crystalline solid, 2-Butyne-1,4-diol, is soluble in water and ethanol.
2-butyne-1,4-diol is an organic compound from the alkyne and diol family .
2-butyne-1,4-diol occurs as colorless to yellow crystals, extremely soluble in water and ethanol.
1,4-butynediol appears as white to light-brown solid or brownish-yellow aqueous solution.
Solid sinks and mixes with water.
2-butyne-1,4-diol is a butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.
2-butyne-1,4-diol is an organic compound that is an alkyne and a diol.
2-butyne-1,4-diol is a colourless, hygroscopic solid that is soluble in water and polar organic solvents.
2-butyne-1,4-diol is a commercially significant compound in its own right and as a precursor to other products.
But-2-yne-1,4-diol is obtained by Reppe synthesis, by reaction of acetylene (ethyne) with an aqueous solution of formaldehyde (methanal) under pressure (2-Butyne-1,4-diol was thus produced on a large scale from 1941) 7:
2 VSH2O + VS2H2⟶VS4H6O2
The reaction normally occurs at a temperature between 90 and 150 °C, depending on the pressure applied to the system which ranges from 1 to 20 bar 8.
Different patented production techniques use catalysts based on copper and bismuth, or even copper acetylide (I) 3.
Annual European production of butynediol is around 200,000 tonnes 3.
2-Butyne-1,4-diol is a colorless to slightly yellow solid, and is almost odorless.
2-Butyne-1,4-diol is completely soluble with water in all proportions.
2-Butyne-1,4-diol is an organic compound combinding an alkyne and a dioland is a precursor to 1,4-Butanediol.
2-butyne-1,4-diol is mainly used in the manufacturing of pesticides, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
The Boiling point of 2-Butin-1,4-diol (BYD, BBD) is at 238°C and melting point at 52-55°C.
Applications of 2-Butyne-1,4-diol:
2-butyne-1,4-diol is transformed by hydrogenation into but-2-ene-1,4-diol and butane-1,4-diol.
2-butyne-1,4-diol is also a precursor of vitamin B6.
2-butyne-1,4-diol is also used in the manufacture of medicines, pesticides , herbicides , flame retardants , anti-corrosion agents , plasticizers , synthetic resins and polyurethanes.
2-butyne-1,4-diol is used in galvanizing processes (by nickel or copper ), and to shine and preserve nickel plating.
2-Butyne-1,4-diol is extensively used in the cycloaddition reactions such as the homologation method for the preparation of substituted acenes, rhodium and iridium-catalyzed [2+ 2+ 2] inter and intramolecular cyclotrimerization.
2-butyne-1,4-diol can also be used in the total synthesis of (−)-isolaurallene, (−)-amphidinolide P and bistramide A.
2-butyne-1,4-diol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation.
2-butyne-1,4-diol is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes.
2-butyne-1,4-diol is the major raw material used in the synthesis of vitamin B6.
2-butyne-1,4-diol is also used for brightening, preserving, and inhibiting nickel plating.
2-butyne-1,4-diol reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO2CC(Cl)=C(Cl)CHO (see mucobromic acid).
Uses of 2-Butyne-1,4-diol:
2-Butyne-1,4-diol is used primarily in the synthesis of organic compounds.
2-Butyne-1,4-diol is a colorless, hygroscopic solid that is soluble in water and polar organic solvents.
2-Butyne-1,4-diol is used basic brightener in nickel electroplating baths, also an important intermediate for organic synthesis; corrosion inhibitor; defoliant ; polymerization accelerator; stabilizer for chlorinated hydrocarbons; cosolvent for paint and varnish removal.
2-Butyne-1,4-diol is used by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
2-Butyne-1,4-diol is used in the following products: washing & cleaning products, coating products, metal surface treatment products and laboratory chemicals.
2-Butyne-1,4-diol is used for the manufacture of: metals, fabricated metal products and electrical, electronic and optical equipment.
Other release to the environment of 2-Butyne-1,4-diol is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
2-Butyne-1,4-diol is used in the following products: washing & cleaning products, water treatment chemicals, pH regulators and water treatment products, coating products and metal surface treatment products.
2-Butyne-1,4-diol has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of 2-Butyne-1,4-diol can occur from industrial use: formulation of mixtures.
2-Butyne-1,4-diol is used in the following products: metal surface treatment products, washing & cleaning products, coating products and laboratory chemicals.
2-Butyne-1,4-diol is used for the manufacture of: fabricated metal products, electrical, electronic and optical equipment, chemicals.
Release to the environment of 2-Butyne-1,4-diol can occur from industrial use: in processing aids at industrial sites and as an intermediate step in further manufacturing of another substance (use of intermediates).
Release to the environment of 2-Butyne-1,4-diol can occur from industrial use: manufacturing of the substance.
2-Butyne-1,4-diol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation.
2-Butyne-1,4-diol is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes.
2-Butyne-1,4-diol is the major raw material used in the synthesis of vitamin B6.
2-Butyne-1,4-diol is also used for brightening, preserving, and inhibiting nickel plating.
2-Butyne-1,4-diol reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO2CC(Cl)=C(Cl)CHO (see mucobromic acid).
2-Butyne-1,4-diol is used as a precursor to prepare 1,4-butanediol, 2-butene-1,4-diol and mucochloric acid.
2-Butyne-1,4-diol is also used in textile additives, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
2-Butyne-1,4-diol is an important raw material of vitamin B6.
Further, 2-Butyne-1,4-diol is used for brightening, preserving and inhibiting nickel plating.
In addition, 2-Butyne-1,4-diol is used in biological studies for nematocidal activity.
2-Butyne-1,4-diol is mainly used in the manufacturing of pesticides, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
2-Butyne-1,4-diol is used as a precursor to prepare 1,4-butanediol, 2-butene-1,4-diol and mucochloric acid.
2-Butyne-1,4-diol is also used in textile additives, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
2-Butyne-1,4-diol is an important raw material of vitamin B6.
Further, 2-Butyne-1,4-diol is used for brightening, preserving and inhibiting nickel plating.
In addition, 2-Butyne-1,4-diol is used in biological studies for nematocidal activity.
2-Butyne-1,4-diol is used to produce butanedioland butenediol, in metal plating andpickling baths, and in making the carbamateherbicide Barban (Carbyne).
2-Butyne-1,4-diol is extensively used in the cycloaddition reactions such as the homologation method for the preparation of substituted acenes, rhodium and iridium-catalyzed [2+ 2+ 2] inter and intramolecular cyclotrimerization.
2-Butyne-1,4-diol can also be used in the total synthesis of (−)-isolaurallene, (−)-amphidinolide P and bistramide A.
2-Butyne-1,4-diol is a precursor to 1,4-butanediol.
2-Butyne-1,4-diol is also used in the manufacture of plant protection agents, pesticides, textile additives, corrosion inhibitors, platicizers, synthetic resins, and polyurethanes.
2-Butyne-1,4-diol is used in biological studies for nematocidal activity.
2-Butyne-1,4-diol uses and applications include: Corrosion inhibitor in acid pickles and cleaners; pharmaceuticals intermediate; electroplating brightener; defoliant; polymerization accelerator; stabilizer for chlorinated hydrocarbons; cosolvent for paint and varnish removal; synthesis of histamine and pyridoxine; alternative route for vitamin B6; emulsifier Suggested storage of 2-Butyne-1,4-diol: Hygroscopic
Functions of 2-Butyne-1,4-diol:
Emulsifier,
Accelerator,
Acid,
Stabilizer
Chemical Properties of 2-Butyne-1,4-diol:
2-Butyne-1,4-diol is a yellow solid.
2-Butyne-1,4-diol is soluble in water, acidic solution, ethanol and acetone, slightly soluble in chloroform, insoluble in benzene and ether.
Solubility of 2-Butyne-1,4-diol:
2-Butyne-1,4-diol is soluble in water, ethanol, acetone, methanol.
2-Butyne-1,4-diol is slightly soluble in ethyl ether and chloroform.
2-Butyne-1,4-diol is insoluble in benzene.
Synthesis of 2-Butyne-1,4-diol:
2-Butyne-1,4-diol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants:
2 CH2O + HCCH → 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.
Handling And Storage of 2-Butyne-1,4-diol:
Precautions for safe handling:
Advice on safe handling:
Work under hood.
Hygiene measures:
Immediately change contaminated clothing.
Wash hands and face after working with substance.
Conditions for safe storage, including any incompatibilities:
Storage:
2-Butyne-1,4-diol can be stored in steel, aluminum, nickel, glass, epoxy, and phenolic liner containers.
Rubber hose may be used for transfer.
Avoid contact with heavy metal salt contaminants.
Storage conditions:
Tightly closed.
Dry.
Keep in a well-ventilated place.
Keep locked up or in an area accessible
Only to qualified or authorized persons.
Air and moisture sensitive.
Handle and store under inert gas.
Stability And Reactivity of 2-Butyne-1,4-diol:
Pure 2-Butyne-1,4-diol is non-explosvie.
Small amounts of certain impurities-alkali hydroxides, alkaline earth hydroxides, halides-may cause explosive decomposition upon distillation.
2-Butyne-1,4-diol should not be treated with basic catalysts in the absence of a solvent at room temperature, and 2-Butyne-1,4-diol’s stability is less with elevated temperatures.
In strong acids, contamination with mercury salts can also result in violent decomposition
Chemical stability:
2-Butyne-1,4-diol is chemically stable under standard ambient conditions (room temperature).
Incompatible materials:
No data available
First Aid Measures of 2-Butyne-1,4-diol:
General advice:
First aiders need to protect themselves.
If inhaled:
After inhalation:
Fresh air.
Immediately call in physician.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Call a physician immediately.
In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.
If swallowed:
Give water to drink (two glasses at most).
Seek medical advice immediately.
Indication of any immediate medical attention and special treatment needed:
No data available
Fire Fighting Measures of 2-Butyne-1,4-diol:
Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
Accidental Release Measures of 2-Butyne-1,4-diol:
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up carefully.
Dispose of properly.
Clean up affected area.
Exposure Controls/Personal Protection of 2-Butyne-1,4-diol:
Personal protective equipment:
Eye/face protection:
Use equipment for eye protection.
Tightly fitting safety goggles
Skin protection:
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Body Protection:
protective clothing
Respiratory protection:
Recommended Filter type: Filter type P3
Control of environmental exposure:
Do not let product enter drains.
Identifiers of 2-Butyne-1,4-diol:
CAS number: 110-65-6
EC index number: 603-076-00-9
EC number: 203-788-6
Hill Formula: C₄H₆O₂
Molar Mass: 86.09 g/mol
HS Code: 2905 39 90
Molecular Weight:86.09 g/mol
Beilstein Number: 1071237
MDL: MFCD00002915
XlogP3-AA: -1.10 (est)
Molecular Weight: 86.09022000
Formula: C4 H6 O2
Appearance: pale brown to brownish-yellow solid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 50.00 °C. @ 760.00 mm Hg
Boiling Point: 238.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.008000 mmHg @ 25.00 °C. (est)
Flash Point: 306.00 °F. TCC ( 152.22 °C. )
logP (o/w): 0.093 (est)
Soluble in: water, 7.958e+005 mg/L @ 25 °C (est)
CAS Min % 98.5
CAS Max % 100.0
Melting Point: 54.0°C to 58.0°C
EC Number：203-788-6
UNII：AXH202FPQM
ICSC Number：1733
NSC Number：834
UN Number：2716
DSSTox ID：DTXSID4021921
Color/Form：Plates from benzene and ethyl acetate
White, orthorhombic crystals
WHITE TO LIGHT YELLOW
Yellow scaley solid at 20 °C and 1,013 hPa
HScode：29053980
PSA：40.5
XLogP3：-0.73
Appearance：slightly brown Crystalline Platelets or Flakes
Density：1.1
Melting Point：58 °C
Properties of 2-Butyne-1,4-diol:
Chemical formula: C4H6O2
Molar mass: 86.090 g·mol−1
Appearance: Colorless crystalline solid
Density: 1.11 g/cm3 (at 20 °C)
Melting point: 58 °C (136 °F; 331 K)
Boiling point: 238 °C (460 °F; 511 K)
Solubility in water: 3740 g/L
Molecular Weight: 86.09 g/mol
XLogP3-AA: -1.1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 86.036779430 g/mol
Monoisotopic Mass: 86.036779430 g/mol
Topological Polar Surface Area: 40.5Ų
Heavy Atom Count: 6
Formal Charge: 0
Complexity: 66
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Boiling point: 125 – 127 °C (3 hPa)
Density: 1.04 – 1.05 g/cm3 (20 °C)
Flash point: 152 °C
Ignition temperature: 410 °C
Melting Point: 56 – 58 °C
pH value: 4 – 7.5 (100 g/l, H₂O, 23 °C)
Vapor pressure: Bulk density: 500 kg/m3
Solubility: 3740 g/l
Physical State :Solid
Solubility :Soluble in water (3740 mg/ml at 20° C),
alcohol, ether, benzene, and acetonez.
Storage :Desiccate at room temperature
Melting Point :53-58° C (lit.)
Boiling Point :238° C (lit.)
Density :1.04 g/cm3
Melting point: 54 °C
Boiling point: 238 °C(lit.)
Density: 1.2
vapor pressure: refractive index: 1.4804
Flash point: 306 °F
storage temp.: Store below +30°C.
solubility: 3740g/l
form: Crystalline Platelets or Flakes
pka: 12.72±0.10(Predicted)
color: slightly brown
PH: 4-7.5 (100g/l, H2O, 23℃)
Water Solubility: 3740 g/L (20 ºC)
BRN: 1071237
Exposure limits ACGIH: TWA 0.1 ppm; STEL 0.3 ppm
OSHA: TWA 0.75 ppm; STEL 2 ppm
NIOSH: IDLH 20 ppm; TWA 0.016 ppm; Ceiling 0.1 ppm
Stability: Stable.