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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.
CAS Number: 110-65-6
Molecular Formula: C4H6O2
Molecular Weight: 86.09
EINECS Number: 203-788-6
Synonyms: 2-Butyne-1,4-diol, 110-65-6, But-2-yne-1,4-diol, Butynediol, 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), Butynediol-1,4 [French], 1,4-Butinodiol [Spanish], 1,4-Butinodiol, Butynediol-1,4, CAS-110-65-6, 2-Butin-1,4-diol [Czech], HSDB 2004, EINECS 203-788-6, UNII-AXH202FPQM, 2-Butin-1,4-diol [Czechoslovakia], 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, STL185542, AKOS000118736, UN 2716, NCGC00249014-01, NCGC00256535-01, NCGC00258836-01, 1,4-Butynediol [UN2716] [Poison], 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, also known as but-2-yne-1,4-diol or butynediol, is a chemical compound with the molecular formula C4H6O2.
It is a diol, meaning it contains two hydroxyl (OH) functional groups.
The compound has a linear structure with a butyne backbone and hydroxyl groups attached to carbon atoms 1 and 4.
2-Butyne-1,4-diol is primarily used as a chemical intermediate in the synthesis of various organic compounds.
It can undergo various chemical reactions, including oxidation, reduction, and substitution reactions, to produce a wide range of products.
2-Butyne-1,4-diol is a butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.
It 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.
It can also be used in the total synthesis of (−)-isolaurallene, (−)-amphidinolide P and bistramide A.
A series of important organic products such as 2-Butyne-1,4-diol, butylene glycol, n-butanol, dihydrofuran, tetrahydrofuran, γ-butyrolactone and pyrrolidone can be used to produce synthetic plastics, synthetic fibers ( Nylon-4), artificial leather, pharmaceuticals, pesticides, solvents (N-methylpyrrolidone) and preservatives.
2-Butyne-1,4-diol itself is a good solvent, in the electroplating industry as a brightener.
2-Butyne-1,4-diol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants.
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.
2-Butyne-1,4-diol is an organic compound combinding an alkyne and a dioland is a precursor to 1,4-Butanediol.
It 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 a precursor to 1,4-butanediol.
It can be used in the manufacture of plant protection agents, pesticides, textile additives, corrosion inhibitors, platicizers, synthetic resins, and polyurethanes.
2-Butyne-1,4-diol is also used for brightening, preserving, and inhibiting nickel plating.
2-Butyne-1,4-diol produced is consumed in the manufacture of butanediol and butenediol.
2-Butyne-1,4-diol undergoes the usual reactions of primary alcohols that contribute to its use as a chemical intermediate.
Because of its rigid, linear structure, many reactions forming cyclic products from butanediol or cis-butenediol give only polymers with butynediol.
Both hydroxyl groups can be esterified normally, and the monoesters are readily prepared as mixtures with diesters and unesterified butynediol, but care must be taken in separating them because the monoesters disproportionate easily.
The hydroxyl groups can be alkylated with the alkylating agents, although a reverse treatment is used to obtain aryl ethers; for example; treatment of butynediol toluene sulfonate or dibromobutyne with a phenol gives the corresponding ether. Reactions of 2-Butyne-1,4-diol with alkylene oxides give ether alcohols.
In the presence of acid catalysts, 2-Butyne-1,4-diol and aldehydes or acetals give polymeric acetals, useful intermediates for acetylenic polyurethanes suitable for high-energy solid propellants.
2-Butyne-1,4-diol is a colorless, hygroscopic solid that is soluble in water and polar organic solvents.
It is primarily used as a synthetic organic intermediate 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 of vitamin B6 and is also used for brightening, preserving, and inhibiting nickel plating.
2-Butyne-1,4-diol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.
White to light-brown solid or brownish-yellow aqueous solution.
2-Butyne-1,4-diol, solid sinks and mixes with water.
2-Butyne-1,4-diol is a colorless to yellow liquid with an amine-like odor.
It is miscible with water in all proportions
2-Butyne-1,4-diol is an organic compound that belongs to the class of diols.
2-Butyne-1,4-diol is a colorless liquid with an odor like that of acetone.
The optimum concentration for the hydrogenation of 2-butene-1,4-diol is between 10 and 30% weight/volume.
The reaction mechanism is a hydrogenation process in which a catalyst promotes the addition of hydrogen molecules to the carbonyl group in 2-Butyne-1,4-diol.
The catalysts used are usually sodium carbonate or potassium carbonate at concentrations between 1 and 10%.
Hydrogenation should be conducted in the presence of x-ray diffraction data as a catalyst identification technique.
2-Butyne-1,4-diol can be used as a solvent for chemical reactions, but it cannot be easily distilled due to its high boiling point (180°C).
2-Butyne-1,4-diol has not been found to exhibit any mutagenic or
2-Butyne-1,4-diol and related compounds involves strategic reactions that enable the formation of the tetraphenyl structure.
For instance, the reaction of 2-Butyne-1,4-diol with chlorodiphenylphosphine leads to significant products other than the 1,4-isomer, showcasing the complex nature of its synthesis and the importance of reaction conditions.
The molecular structure of compounds similar to 2-Butyne-1,4-diol, such as 1,1,6,6-tetraphenylhexa-2,4-diyne-1,6-diol, reveals intricate details about their crystal packing and hydrogen bonding patterns, providing insights into their stability and reactivity.
For example, the inclusion compounds formed with benzene, toluene, and mesitylene exhibit distinct crystal packing arrangements and hydrogen bonding, indicative of the versatile interaction capabilities of these diol compounds.
2-Butyne-1,4-diol and its analogs often lead to the formation of novel structures with unique properties.
For instance, the rhodium-catalyzed double [2 + 2 + 2] cycloaddition provides a modular and versatile synthesis method for biaryl diphosphines, highlighting the compound's reactivity and potential for creating complex molecular systems.
The physical properties of 2-Butyne-1,4-diol derivatives, such as thermal behavior and crystal structure, are critical for understanding their stability and suitability for various applications.
Studies on related compounds demonstrate high thermal stability and distinct crystalline structures, which are essential for their function in material science and organic electronics.
The chemical properties, including reactivity with different reagents and participation in complexation reactions, are pivotal for the utility of 2-Butyne-1,4-diol in synthesizing advanced materials and catalysts.
For example, the inclusion compound formation with acetone and benzophenone showcases the compound's ability to interact and form stable complexes, indicating its utility in host-guest chemistry
2-Butyne-1,4-diol is used as a monomer in the production of certain types of polymers and copolymers, particularly those with special properties such as flexibility, adhesion, or chemical resistance.
2-Butyne-1,4-diol can be incorporated into adhesive and sealant formulations to improve bonding strength and durability.
2-Butyne-1,4-diol is employed in the textile industry as a chemical intermediate for the synthesis of dye intermediates, textile finishing agents, and flame retardants.
Some photographic chemicals and solutions may contain 2-Butyne-1,4-diol as a stabilizer or solvent component.
In coatings and paints formulations, 2-Butyne-1,4-diol can serve as a crosslinking agent or modifier to enhance coating properties such as hardness, flexibility, and weather resistance.
2-Butyne-1,4-diol is used in the synthesis of specialty chemicals, such as pharmaceutical intermediates, agricultural chemicals, and specialty solvents.
It can be used as a plasticizer in polymer formulations to improve flexibility, resilience, and processability of plastics.
In some cases, 2-Butyne-1,4-diol is added to fuels as an additive to enhance combustion efficiency or reduce emissions.
2-Butyne-1,4-diol may be used as a corrosion inhibitor in metalworking fluids, coolants, and other industrial formulations to protect metal surfaces from corrosion and rust.
2-Butyne-1,4-diol is utilized in the synthesis of hydrogels, which are crosslinked polymer networks capable of absorbing and retaining large amounts of water.
In the rubber industry, 2-Butyne-1,4-diol can be used as a crosslinking agent in the vulcanization process to improve the strength, elasticity, and durability of rubber products.
2-Butyne-1,4-diol is sometimes included in antifreeze formulations as a component to lower the freezing point of water and provide protection against cold temperatures.
2-Butyne-1,4-diol can serve as a starting material for the synthesis of surfactants, which are compounds used to reduce surface tension and improve wetting and dispersing properties in various applications.
It may be used in electroplating baths as an additive to improve the quality and uniformity of metal coatings deposited onto substrates.
Some research suggests potential biomedical applications for 2-Butyne-1,4-diol, including its use in drug delivery systems, tissue engineering, and medical device coatings.
2-Butyne-1,4-diol can be used as a reagent in analytical chemistry techniques, such as chromatography and spectroscopy, for the detection and quantification of various compounds.
Melting point: 54 °C
Boiling point: 238 °C(lit.)
Density: 1.2
vapor pressure: <0.1 mm Hg ( 55 °C)
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. Highly flammable solid. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong acids, strong bases.
LogP: -0.73 at 25℃
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 its stability is less with elevated temperatures.
In strong acids, contamination with mercury salts can also result in violent decomposition.
In fuel cell technology, 2-Butyne-1,4-diol has been investigated as a potential material for proton exchange membranes (PEMs) due to its conductivity and stability under certain conditions.
2-Butyne-1,4-diols are essential components in proton exchange membrane fuel cells (PEMFCs), which are used for generating electricity from hydrogen and oxygen.
Research suggests that certain derivatives of 2-Butyne-1,4-diol may have potential applications in hydrogen storage materials.
These materials are crucial for the development of hydrogen fuel technologies, including hydrogen-powered vehicles and portable fuel cells.
Chemists utilize 2-Butyne-1,4-diol as a building block in organic synthesis to introduce functional groups or structural motifs into organic molecules.
Its terminal alkynyl groups make it a valuable precursor for the synthesis of more complex organic compounds.
While primarily used in industrial and chemical processes, 2-Butyne-1,4-diol and its derivatives have also found applications in biological research and pharmaceutical development.
They may serve as starting materials for the synthesis of bioactive compounds or as probes for studying biological processes.
In heterogeneous catalysis, 2-Butyne-1,4-diol-functionalized supports have been investigated for their potential in catalytic reactions.
These functionalized supports can enhance catalyst stability, activity, and selectivity, leading to improved catalytic performance in various chemical transformations.
Due to its ability to form crosslinks between polymer chains, 2-Butyne-1,4-diol is utilized as a crosslinking agent in the production of adhesives, coatings, and elastomers.
Crosslinking enhances the mechanical properties and durability of these materials.
Some derivatives of 2-Butyne-1,4-diol are used as intermediates in the synthesis of dyes and pigments.
These compounds play a crucial role in the coloration of textiles, plastics, paints, and other materials.
Certain derivatives of 2-Butyne-1,4-diol have been investigated as photoinitiators for polymerization reactions initiated by ultraviolet (UV) or visible light.
These photoinitiators enable rapid and controlled polymerization processes in various applications, including coatings, adhesives, and dental materials.
2-Butyne-1,4-diol as a precursor in the synthesis of pharmaceutical compounds.
It serves as a versatile building block for introducing functional groups and structural motifs into drug molecules.
Additionally, certain derivatives of 2-Butyne-1,4-diol exhibit biological activity and are investigated for their potential therapeutic applications.
In the textile industry, 2-Butyne-1,4-diol is utilized as a sizing agent in fabric finishing processes.
Sizing agents improve the weaving and handling properties of yarns by providing lubrication and reducing friction during textile manufacturing.
Some derivatives of 2-Butyne-1,4-diol are employed in water treatment applications as chelating agents or complexing agents.
2-Butyne-1,4-diols can bind to metal ions in water and facilitate their removal through precipitation or filtration processes.
Similar to textile sizing, 2-Butyne-1,4-diol can be used as a sizing agent in paper manufacturing to improve the strength, smoothness, and printability of paper products.
Sizing agents prevent ink from spreading and enhance the performance of printing processes.
Analytical chemists use 2-Butyne-1,4-diol and its derivatives as calibration standards and reference materials in chromatography, spectroscopy, and other analytical techniques.
2-Butyne-1,4-diols aid in the identification, quantification, and characterization of organic compounds in complex mixtures.
In the electronics industry, 2-Butyne-1,4-diol is employed in the production of electronic components, such as printed circuit boards (PCBs) and semiconductor devices.
2-Butyne-1,4-diol may serve as a solvent, cleaning agent, or surface modifier in electronic manufacturing processes.
While not directly used as a food additive, 2-Butyne-1,4-diol and its derivatives may find applications in food packaging materials, coatings, and adhesives.
These materials help improve the safety, shelf life, and quality of packaged food products.
In certain applications, 2-Butyne-1,4-diol derivatives may be used as fuel additives to improve fuel efficiency, combustion performance, and emissions control in internal combustion engines.
Some derivatives of 2-Butyne-1,4-diol are used in cosmetics and personal care products as moisturizing agents, emollients, or humectants.
These compounds help hydrate and soften the skin, hair, and nails.
Uses Of 2-Butyne-1,4-diol:
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, it is used in biological studies for nematocidal activity.
2-Butyne-1,4-diol 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.
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.
It 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 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 and .
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).
2-Butyne-1,4-diol is used as a precursor to prepare 1,4-butanediol, 2-butene-1,4-diol and mucochloric acid.
It 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, it is used in biological studies for nematocidal activity.
2-Butyne-1,4-diol is use for the production of 2-Butyne-1,4-diol, butanediol, γ-butyrolactone series of chemical products.
2-Butyne-1,4-diol is use Used as organic synthesis intermediates and instrument plating materials.
2-Butyne-1,4-diol is use of primary nickel plating brightener.
2-Butyne-1,4-diol is uses for organic raw materials, solvents, cyanide-free plating solution, also used in artificial leather, pharmaceutical and pesticide industry.
2-Butyne-1,4-diol is use of butadiene synthesis of intermediates, corrosion inhibitors, electroplating brightener, polymerization catalyst, defoliants, chlorinated hydrocarbons stabilizer.
2-Butyne-1,4-diol is utilized as a monomer or a building block in the production of various polymers and copolymers.
These polymers find applications in industries such as adhesives, coatings, and plastics.
2-Butyne-1,4-diol is incorporated into adhesive and sealant formulations to enhance bonding strength, flexibility, and durability.
These products are used in construction, automotive, and industrial applications.
2-Butyne-1,4-diol is used in the textile industry as a dye intermediate, softener, or finishing agent.
Additionally, it may be utilized in fabric sizing to improve weaving properties and reduce friction during textile manufacturing.
Certain derivatives of 2-Butyne-1,4-diol are employed in the production of photographic chemicals, including developers and fixing solutions, for traditional film photography.
In the rubber industry, it serves as a crosslinking agent in the vulcanization process, improving the mechanical properties and durability of rubber products such as tires, hoses, and seals.
2-Butyne-1,4-diol is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
2-Butyne-1,4-diol is utilized in the production of hydrogels, which are highly absorbent polymer networks used in medical, agricultural, and personal care applications.
Some derivatives of 2-Butyne-1,4-diol are employed as corrosion inhibitors in metalworking fluids, coolants, and surface treatments to protect metal surfaces from corrosion and rust.
In certain applications, it may be used as a fuel additive to improve combustion efficiency or reduce emissions in internal combustion engines.
Researchers may use 2-Butyne-1,4-diol and its derivatives in biomedical research for applications such as drug delivery systems, tissue engineering, and biomaterials development.
2-Butyne-1,4-diol can be utilized as a starting material for the synthesis of surfactants, which are compounds that lower the surface tension between two substances, such as liquids or a liquid and a solid.
Surfactants have applications in detergents, emulsifiers, and foaming agents.
In the electroplating industry, 2-Butyne-1,4-diol is used as an additive in electroplating baths to improve the quality and uniformity of metal coatings deposited onto substrates.
2-Butyne-1,4-diol can help control the deposition rate and the morphology of the plated metal.
Some derivatives of 2-Butyne-1,4-diol are employed in paper manufacturing processes as sizing agents or additives to improve the strength, smoothness, and printability of paper products.
Sizing agents prevent ink from spreading and enhance the performance of printing processes.
Certain derivatives of 2-Butyne-1,4-diol are used in water treatment applications as chelating agents or complexing agents.
These compounds can bind to metal ions in water and facilitate their removal through precipitation or filtration processes.
2-Butyne-1,4-diol and its derivatives are utilized in analytical chemistry as calibration standards and reference materials in chromatography, spectroscopy, and other analytical techniques.
These compounds aid in the identification, quantification, and characterization of organic compounds in complex mixtures.
In heterogeneous catalysis, 2-Butyne-1,4-diol-functionalized supports have been investigated for their potential in catalytic reactions.
These functionalized supports can enhance catalyst stability, activity, and selectivity, leading to improved catalytic performance in various chemical transformations.
Research suggests that certain derivatives of 2-Butyne-1,4-diol may have potential applications in proton exchange membranes (PEMs) for fuel cells.
These membranes are essential components in proton exchange membrane fuel cells (PEMFCs), which are used for generating electricity from hydrogen and oxygen.
Safety Profile Of 2-Butyne-1,4-diol:
2-Butyne-1,4-diol is corrosive and irritates the skin, eyes, and respiratory tract.
A poison by ingestion.
A skin sensitizer upon long or repeated contact.
When heated to decomposition it emits acrid smoke and fumes and may explode.
Explosive reaction with traces of alkaltes, alkali earth hydroxides, halide salts, strong acids, mercury salts + strong acids.
2-Butyne-1,4-diol exhibits moderate to hightoxicity in test animals.
2-Butyne-1,4-diol is about 10 timesmore toxic than are the saturated C4 diols.
2-Butyne-1,4-diol causes irritation to the skin.
Noncombustible solid, flash point (open cup) 152°C (305.6°F).
2-Butyne-1,4-diol is stable at room temperature.
But the dry compound explodes in the presence of certain heavy metal salts, such as mercuric chloride.
Heating with alkaline solution may result in an explosion.
