ChemicalBook > Product Catalog > Organic Chemistry > Alcohols,Phenols,Phenol alcohols > Acyclic alcohols > 1,4-Butanediol
1,4-Butanediol Chemical Properties
- Melting point:20 °C
- Boiling point:230 °C(lit.)
- Density 1.017 g/mL at 25 °C(lit.)
- vapor density 3.1 (vs air)
- vapor pressure <0.1 hPa (20 °C)
- refractive index n
- Flash point:135 °C
- storage temp. 2-8°C
- form Liquid
- color Clear colorless
- PH7-8 (500g/l, H2O, 20℃)
- explosive limit1.95-18.3%(V)
- Water Solubility Miscible
- Sensitive Hygroscopic
- BRN 1633445
- Stability:Stable. Combustible. Incompatible with strong oxidizing agents, mineral acids, acid chlorides, acid anhydrides.
- CAS DataBase Reference110-63-4(CAS DataBase Reference)
- NIST Chemistry Reference1,4-Butanediol(110-63-4)
- EPA Substance Registry System1,4-Butanediol (110-63-4)
1,4-Butanediol Usage And Synthesis
- Chemical Properties1,4-butanediol (1,4-BD) is a colorless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain and is one of four stable isomers of butanediol.the hydroxyl function of each end group of the Butanediol reacts with different mono- and bifunctional reagents: for example with dicarboxylic acids to polyesters, with diisocyanates to polyurethanes, or with phosgene to polycarbonates. 1.4-Butanediol (BDO) is a high-quality intermediate. BDO and its derivatives are widely used for producing plastics, solvents, electronic chemicals and elastic fibers. Additionally BDO is also a building block for the synthesis of polyesterpolyols and polyetherpolyols. BASF is the most significant producer of 1,4-Butanediol and its derivatives worldwide.
- Butanediol and its derivatives is used in a broad spectrum of applications in the chemical industry; amongst others in the manufacturing of technical plastics, polyurethanes, solvents, electronic chemicals and elastic fibres.
- 1,4-Butanediol is used in the synthesis of epothilones, a new class of cancer drugs. Also used in the stereoselective synthesis of (-)-Brevisamide.
- 1,4-Butanediol's largest use is within tetrahydrofuran (THF) production, used to make polytetramethylene ether glycol, which goes mainly into spandex fibers, urethane elastomers, and copolyester ethers.
- It is commonly used as a solvent in the chemical industry to manufacture gamma-butyrolactone and elastic fibers like spandex.
- It is used as a cross-linking agent for thermoplastic urethanes, polyester plasticizers, paints and coatings.
- It undergoes dehydration in the presence of phosphoric acid yielded teterahydrofuran, which is an important solvent used for various applications.
- It acts an intermediate and is used to manufacture polytetramethylene ether glycol (PTMEG), polybutylene terephthalate (PBT) and polyurethane (PU).
- It finds application as an industrial cleaner and a glue remover.
- 1,4-butanediol is also used as a plasticiser (e.g. in polyesters and cellulosics), as a carrier solvent in printing ink, a cleaning agent, an adhesive (in leather, plastics, polyester laminates and polyurethane footwear), in agricultural and veterinary chemicals and in coatings (in paints, varnishes and films).
- Usesbutylene glycol is a solvent with good antimicrobial action. It enhances the preservative activity of parabens. Butylene glycol also serves as a humectant and viscosity controller, and to mask odor.
- Uses1,4-Butanediol is used to produce polybutyleneterephthalate, a thermoplastic polyester;and in making tetrahydrofuran, butyrolactones,and polymeric plasticizers.
- Production MethodsMethods of manufacturing:
The most prevalent 1,4-BD production route worldwide is BASF's Reppe process, which reacts acetylene and formaldehyde. Acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol, also known as but-2-yne- 1,4-diol. Hydrogenation of 1,4-butynediol gives 1,4-butanediol. 1,4-BD is also made on a large industrial scale by continuous hydrogenation of the 2-butyne- 1,4-diol over modified nickel catalysts. The one-stage flow process is carried out at 80 - 160 deg C and 300 bar.
Mitsubishi uses a three-step process:
(1) the catalytic reaction of butadiene and acetic acid yields 1,4-diacetoxy-2-butene;
(2) subsequent hydrogenation gives 1,4-diacetoxybutane; and
(3) hydrolysis leads to 1,4-butanediol.
- Synthesis Reference(s)The Journal of Organic Chemistry, 36, p. 2018, 1971 DOI: 10.1021/jo00813a043
Tetrahedron Letters, 33, p. 6371, 1992 DOI: 10.1016/S0040-4039(00)60976-0
- General DescriptionOdorless colorless liquid or solid (depending upon temperature).
- Air & Water ReactionsHighly flammable. 1,4-Butanediol is hygroscopic. Water soluble.
- Reactivity Profile1,4-Butanediol is heat and light sensitive. 1,4-Butanediol reacts with acid chlorides, acid anhydrides and chloroformates; reacts with oxidizing agents and reducing agents. 1,4-Butanediol is incompatible with isocyanates and acids; also incompatible with peroxides, perchloric acid, sulfuric acid, hypochlorous acid, nitric acid, caustics, acetaldehyde, nitrogen peroxide and chlorine.
- HazardToxic by ingestion.
- Health HazardThe acute toxic effects are mild. 1,4-Butanediolis less toxic than its unsaturate analogs,butenediol and the butynediol. The oralLD50 value in white rats and guinea pigsis ~2 mL/kg. The toxic symptoms fromingestion may include excitement, depressionof the central nervous system, nausea, anddrowsiness.
- Health HazardIngestion of large amounts needed to produce any symptoms.
- Fire HazardNonflammable liquid, flash point (open cup) 121°C.
- Safety ProfileA human poison by an unspecified route. Moderately toxic byingestion and intraperitoneal routes. Human systemic effects: altered sleep time. Combustible when exposed to heat or flame. To fight fire, use alcohol foam, mist, foam, CO2, dry chemical. Incompatible with oxidizing materials. When heated to decomposition it emits acrid smoke and fumes.
- Purification MethodsDistil the glycol and store it over Linde type 4A molecular sieves, or crystallise it twice from anhydrous diethyl ether/acetone, and redistil it. It has been recrystallised from the melt and doubly distilled in vacuo in the presence of Na2SO4. [Beilstein 1 IV 2515.]
1,4-Butanediol Preparation Products And Raw materials
- Preparation ProductsTetrahydrofurangamma-ButyrolactonePolyurethane foamsTriethylene glycol dimethacrylate1,4-DibromobutanePOLY(1,4-BUTYLENE TEREPHTHALATE)GD visible light curing composite resinPolyesterPolyol2,3-Dihydrofuran1,4-BUTANEDIOL DIACRYLATE4-Hydroxybutyl acrylatePolyvinylpyrrolidoneBusulfan
- Raw materialsFormaldehydeNickel1,3-BUTADIENEAcetylene2,3-Butanedione2-Butyne-1,4-diol2-CHLORO-1,3-BUTADIENEcis-1,4-Dichloro-2-butene
- 1,3-CYCLOPENTANEDIOL GlycolEthers 1-BUTENE Hexylene Glycol 1,4-Butanediol, d,l-2,3-dibromo-,1,4-BUTANEDIOL, 2,3-DIBROMO-, (+,-)-,1,4-Butanediol, 2,3-dibromo-, (R*,R*)-(.+/-.)-,2,3-dibromo-,(+,-)-4-butanedio DI(PROPYLENE GLYCOL) BUTYL ETHER 1,4-Butanediol (+/-)-1,2-BUTANEDIOL,1,2-BUTANEDIOL 2-Butoxyethyl acetate Dipropylene glycol Diethylene glycol 2,3-Butanediol Ethylene glycol (S,S)-(+)-2,3-BUTANEDIOL,(S,S)-2,3-BUTANEDIOL 2-Butoxyethanol 1,3-Butanediol Ethylene glycol diacetate PROPYLENE GLYCOL
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