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1,4-Butynediol can undergo various chemical reactions, including oxidation, reduction, and substitution reactions, to produce a wide range of products.
1,4-Butynediol is an organic compound combinding an alkyne and a dioland is a precursor to 1,4-Butanediol.
1,4-Butynediol is mainly used in the manufacturing of pesticides, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
CAS Number: 110-65-6
EC Number: 203-788-6
IUPAC Name: But-2-yne-1,4-diol
Chemical Formula: C4H6O2
Other names: 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
1,4-Butynediol is used as a precursor to prepare 1,4-butanediol, 2-butene-1,4-diol and mucochloric acid.
1,4-Butynediol is also used in textile additives, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
1,4-Butynediol is an important raw material of vitamin B6.
Further, 1,4-Butynediol is used for brightening, preserving and inhibiting nickel plating.
In addition, 1,4-Butynediol is used in biological studies for nematocidal activity.
1,4-Butynediol 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.
1,4-Butynediol is also used for brightening, preserving, and inhibiting nickel plating.
1,4-Butynediol 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 1,4-Butynediol 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 1,4-Butynediol 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
1,4-Butynediol 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.
1,4-Butynediol can be incorporated into adhesive and sealant formulations to improve bonding strength and durability.
1,4-Butynediol 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 1,4-Butynediol as a stabilizer or solvent component.
In coatings and paints formulations, 1,4-Butynediol can serve as a crosslinking agent or modifier to enhance coating properties such as hardness, flexibility, and weather resistance.
1,4-Butynediol 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, 1,4-Butynediol is added to fuels as an additive to enhance combustion efficiency or reduce emissions.
1,4-Butynediol may be used as a corrosion inhibitor in metalworking fluids, coolants, and other industrial formulations to protect metal surfaces from corrosion and rust.
1,4-Butynediol 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, 1,4-Butynediol can be used as a crosslinking agent in the vulcanization process to improve the strength, elasticity, and durability of rubber products.
1,4-Butynediol is sometimes included in antifreeze formulations as a component to lower the freezing point of water and provide protection against cold temperatures.
1,4-Butynediol 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 1,4-Butynediol, including its use in drug delivery systems, tissue engineering, and medical device coatings.
1,4-Butynediol can be used as a reagent in analytical chemistry techniques, such as chromatography and spectroscopy, for the detection and quantification of various compounds.
1,4-Butynediol 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).
1,4-Butynediol 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.
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.
1,4-Butynediol is a colourless, hygroscopic solid that is soluble in water and polar organic solvents.
1,4-Butynediol is a commercially significant compound in its own right and as a precursor to other products.
1,4-Butynediol produced is consumed in the manufacture of butanediol and butenediol.
1,4-Butynediol 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 1,4-Butynediol with alkylene oxides give ether alcohols.
In the presence of acid catalysts, 1,4-Butynediol and aldehydes or acetals give polymeric acetals, useful intermediates for acetylenic polyurethanes suitable for high-energy solid propellants.
A series of important organic products such as 1,4-Butynediol, 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.
1,4-Butynediol itself is a good solvent, in the electroplating industry as a brightener.
1,4-Butynediol 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.
1,4-Butynediol is an organic compound that is an alkyne and a diol.
1,4-Butynediol, also known as but-2-yne-1,4-diol or butynediol, is a chemical compound with the molecular formula C4H6O2.
1,4-Butynediol is primarily used as a chemical intermediate in the synthesis of various organic compounds.
1,4-Butynediol 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.
1,4-Butynediol is the major raw material of vitamin B6 and is also used for brightening, preserving, and inhibiting nickel plating.
1,4-Butynediol that is but-2-yne substituted by hydroxy groups at positions 1 and 4.
White to light-brown solid or brownish-yellow aqueous solution.
1,4-Butynediol, solid sinks and mixes with water.
1,4-Butynediol is a colorless to yellow liquid with an amine-like odor.
It is miscible with water in all proportions
1,4-Butynediol is an organic compound that belongs to the class of diols.
1,4-Butynediol 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 1,4-Butynediol.
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.
1,4-Butynediol can be used as a solvent for chemical reactions, but it cannot be easily distilled due to its high boiling point (180°C).
1,4-Butynediol has not been found to exhibit any mutagenic or
1,4-Butynediol and related compounds involves strategic reactions that enable the formation of the tetraphenyl structure.
For instance, the reaction of 1,4-Butynediol 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 1,4-Butynediol, 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.
1,4-Butynediol is non-explosvie.
Small amounts of certain impurities-alkali hydroxides, alkaline earth hydroxides, halides-may cause explosive decomposition upon distillation.
1,4-Butynediol 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, 1,4-Butynediol has been investigated as a potential material for proton exchange membranes (PEMs) due to its conductivity and stability under certain conditions.
1,4-Butynediols 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 1,4-Butynediol 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 1,4-Butynediol 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, 1,4-Butynediol 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, 1,4-Butynediol-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, 1,4-Butynediol 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 1,4-Butynediol 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 1,4-Butynediol 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.
1,4-Butynediol 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 1,4-Butynediol exhibit biological activity and are investigated for their potential therapeutic applications.
In the textile industry, 1,4-Butynediol 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 1,4-Butynediol are employed in water treatment applications as chelating agents or complexing agents.
1,4-Butynediols can bind to metal ions in water and facilitate their removal through precipitation or filtration processes.
Similar to textile sizing, 1,4-Butynediol 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 1,4-Butynediol and its derivatives as calibration standards and reference materials in chromatography, spectroscopy, and other analytical techniques.
1,4-Butynediols aid in the identification, quantification, and characterization of organic compounds in complex mixtures.
In the electronics industry, 1,4-Butynediol is employed in the production of electronic components, such as printed circuit boards (PCBs) and semiconductor devices.
1,4-Butynediol may serve as a solvent, cleaning agent, or surface modifier in electronic manufacturing processes.
While not directly used as a food additive, 1,4-Butynediol 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, 1,4-Butynediol derivatives may be used as fuel additives to improve fuel efficiency, combustion performance, and emissions control in internal combustion engines.
Some derivatives of 1,4-Butynediol 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 1,4-Butynediol:
1,4-Butynediol is use of butadiene synthesis of intermediates, corrosion inhibitors, electroplating brightener, polymerization catalyst, defoliants, chlorinated hydrocarbons stabilizer.
1,4-Butynediol 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.
1,4-Butynediol is incorporated into adhesive and sealant formulations to enhance bonding strength, flexibility, and durability.
These products are used in construction, automotive, and industrial applications.
1,4-Butynediol 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 1,4-Butynediol 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.
1,4-Butynediol is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
1,4-Butynediol is utilized in the production of hydrogels, which are highly absorbent polymer networks used in medical, agricultural, and personal care applications.
Some derivatives of 1,4-Butynediol 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 1,4-Butynediol and its derivatives in biomedical research for applications such as drug delivery systems, tissue engineering, and biomaterials development.
1,4-Butynediol 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, 1,4-Butynediol is used as an additive in electroplating baths to improve the quality and uniformity of metal coatings deposited onto substrates.
1,4-Butynediol is also used in textile additives, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes.
1,4-Butynediol is an important raw material of vitamin B6.
Further, 1,4-Butynediol is used for brightening, preserving and inhibiting nickel plating.
In addition, it is used in biological studies for nematocidal activity.
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.
1,4-Butynediol is the major raw material used in the synthesis of vitamin B6.
1,4-Butynediol 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).
1,4-Butynediol is used in the following products: washing & cleaning products, coating products, metal surface treatment products and laboratory chemicals.
1,4-Butynediol is used for the manufacture of: metals, fabricated metal products and electrical, electronic and optical equipment.
Other release to the environment of 1,4-Butynediol 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.
1,4-Butynediol 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.
1,4-Butynediol has an industrial use resulting in manufacture of another substance (use of intermediates).
Release to the environment of 1,4-Butynediol can occur from industrial use: formulation of mixtures.
1,4-Butynediol is used in the following products: metal surface treatment products, washing & cleaning products, coating products and laboratory chemicals.
1,4-Butynediol is used for the manufacture of: fabricated metal products, electrical, electronic and optical equipment, chemicals and .
Release to the environment of 1,4-Butynediol 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).
1,4-Butynediol 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.
1,4-Butynediol is used as a precursor to prepare 1,4-butanediol, 2-butene-1,4-diol and mucochloric acid.
1,4-Butynediol is an important raw material of vitamin B6.
1,4-Butynediol can help control the deposition rate and the morphology of the plated metal.
Some derivatives of 1,4-Butynediol 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 1,4-Butynediol 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.
1,4-Butynediol 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, 1,4-Butynediol-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 1,4-Butynediol 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.
Further, 1,4-Butynediol is used for brightening, preserving and inhibiting nickel plating.
In addition, it is used in biological studies for nematocidal activity.
1,4-Butynediol is use for the production of 1,4-Butynediol, butanediol, γ-butyrolactone series of chemical products.
1,4-Butynediol is use Used as organic synthesis intermediates and instrument plating materials.
1,4-Butynediol is use of primary nickel plating brightener.
1,4-Butynediol is uses for organic raw materials, solvents, cyanide-free plating solution, also used in artificial leather, pharmaceutical and pesticide industry.
Safety Profile Of 1,4-Butynediol:
1,4-Butynediol 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.
1,4-Butynediol exhibits moderate to hightoxicity in test animals.
1,4-Butynediol is about 10 timesmore toxic than are the saturated C4 diols.
1,4-Butynediol causes irritation to the skin.
Noncombustible solid, flash point (open cup) 152°C (305.6°F).
1,4-Butynediol 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.
