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1,4-Butanediol (BDO), also called Butane-1,4-diol (other names include 1,4-B, BD, BDO and 1,4-BD), is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH.
1,4-Butanediol (BDO) is a colorless viscous liquid first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol".
1,4-Butanediol (BDO) is a butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group.
CAS: 110-63-4
MF: C4H10O2
MW: 90.12
EINECS: 203-786-5
Synonyms
1,4-BUTYLENE GLYCOL;1,4-BUTANEDIOL;1,4-DIHYDROXYBUTANE;AKOS BBS-00004303;BDO;BUTANEDIOL, 1,4-;TETRAMETHYLENE GLYCOL;VERSALINK CURATIVE 1,4 BDO;1,4-BUTANEDIOL;Butane-1,4-diol;110-63-4;Tetramethylene glycol;1,4-Butylene glycol;1,4-Dihydroxybutane;1,4-Tetramethylene glycol;Tetramethylene 1,4-diol;Sucol B;DIOL 14B;1,4-BD;Agrisynth B1D;HO(CH2)4OH;CCRIS 5984;NSC 406696;HSDB 1112;HOCH2CH2CH2CH2OH;UNII-7XOO2LE6G3;EINECS 203-786-5;7XOO2LE6G3;MFCD00002968;BRN 1633445;1,4 butylene glycol;DTXSID2024666;CHEBI:41189;AI3-07553;NSC-406696;DTXCID804666;EC 203-786-5;4-01-00-02515 (Beilstein Handbook Reference);BDO;Dabco DBO;BU1;CAS-110-63-4;Dihydroxybutane;4-hydroxybutanol;1,4butanediol;1.4-butanediol;Dabco BDO;1,4-butandiol;1,4-butane diol;1,4-butane-diol;butane 1,4-diol;butane diol-1,4;butane-1-4-diol;1,4- butandiol;Butan-1.4-diol;1.4 - butanediol;1,4-BUTANDIOLE;1,4-Butanediol, 99%;WLN: Q4Q;MLS001061198;CHEMBL171623;1,4-BUTANEDIOL [MI];1,4-BUTANEDIOL [HSDB];HMS3039N12;Tox21_202245;Tox21_303040;NSC406696;STL283940;AKOS000118735;1,4-Butanediol, for synthesis, 98%;CS-W016669;DB01955;1,4-Butanediol, ReagentPlus(R), 99%;NCGC00090733-01;NCGC00090733-02;NCGC00257119-01;NCGC00259794-01;BP-21418;SMR000677930;1,4-Butanediol, ReagentPlus(R), >=99%;Polytetramethylene Ether GlycolPolyol 220;B0680;NS00006936;F71206;1,4-Butanediol, Vetec(TM) reagent grade, 98%;Q161521;J-503971;J-512798;F0001-0222;InChI=1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H
;732189-03-6
A colourless, water-miscible, viscous liquid at room temperature (m.p. 16℃) with a high boiling point (230℃), 1,4-Butanediol (BDO) is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF).
1,4-Butanediol (BDO) has a role as a neurotoxin, a protic solvent and a prodrug.
1,4-Butanediol (BDO) is a butanediol and a glycol.
Butanediol and 1,4-Butanediol (BDO)'s 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.
The hydroxyl function of each end group of the Butanediol reacts with different mono- and bifunctional reagents:
e.g. with dicarboxylic acids to polyesters, with diisocyanates to polyurethanes, or with phosgene to polycarbonates.
Additionally 1,4-Butanediol (BDO) is also a building block for the synthesis of polyesterpolyols and polyetherpolyols.
1,4-Butanediol (BDO), BDO is a building block for unsaturated polyesters, saturated polyesters and polyurethanes.
1,4-Butanediol (BDO)'s suitable for flexible furniture coatings and repair putties and is used for flexible solvent borne paints, plasticizers and soft segments for polyurethanes.
1,4-Butanediol (BDO) is a colorless, high-boiling liquid with a low odor of toxicity.
1,4-Butanediol (BDO) is completely soluble in water, most alcohol, esters, ketones, glycol ethers and acetates, but may be immiscible or partially miscible in common aliphatic and
aromatic/ chlorinated hydrocarbons.
1,4-Butanediol (BDO) is a versatile chemical
intermediate because of its terminal, primary hydroxyl groups and its hydrophilic and
chemical resistant nature.
Polymers produced upon reaction with diacids or diisocyanates are the basis for many commercial polyurethane and polyester applications.
1,4-Butanediol (BDO) is a versatile organic compound primarily used as a solvent, a precursor in the production of various polymers and plastics, and as a chemical intermediate in the synthesis of other compounds.
1,4-Butanediol (BDO) Chemical Properties
Melting point: 16 °C (lit.)
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: n20/D 1.445(lit.)
Fp: 135 °C
Storage temp.: Store below +30°C.
pka: 14.73±0.10(Predicted)
Form: Liquid
Color: Clear colorless
Odor: Odorless
PH: 7-8 (500g/l, H2O, 20℃)
Explosive limit: 1.95-18.3%(V)
Water Solubility: Miscible
Sensitive: Hygroscopic
BRN: 1633445
Dielectric constant: 30.0（30℃）
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, mineral acids, acid chlorides, acid anhydrides.
InChIKey: WERYXYBDKMZEQL-UHFFFAOYSA-N
LogP: -0.88 at 25℃
CAS DataBase Reference: 110-63-4(CAS DataBase Reference)
NIST Chemistry Reference: 1,4-Butanediol(110-63-4)
EPA Substance Registry System: 1,4-Butanediol (BDO) (110-63-4)
1,4-Butanediol (BDO) 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 1,4-Butanediol (BDO) is also a building block for the synthesis of polyesterpolyols and polyetherpolyols.
BASF is the most significant producer of 1,4-Butanediol (BDO) and its derivatives worldwide.
Synthesis
Conversion of butane to butanediol or butyrolactone via oxidation to maleic anhydride followed by hydrogenation over copper chromite.
In one industrial chemical synthesis, acetylene reacts with two equivalents of formaldehyde to form butyne-1,4-diol.
Hydrogenation of butyne-1,4-diol gives butane-1,4-diol.
1,4-Butanediol (BDO) is also made on an industrial scale from maleic anhydride in the Davy process, which is first converted to the methyl maleate ester, then hydrogenated.
Other routes are from butadiene, allyl acetate and succinic acid.
A biological route to BD has been commercialized that uses a genetically modified organism.
The biosynthesis proceeds via 4-hydroxybutyrate.
Uses
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 (BDO) is used in the synthesis of epothilones, a new class of cancer drugs. Also used in the stereoselective synthesis of (-)-Brevisamide.
1,4-Butanediol (BDO)'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.
1,4-Butanediol (BDO) is commonly used as a solvent in the chemical industry to manufacture gamma-butyrolactone and elastic fibers like spandex.
1,4-Butanediol (BDO) is used as a cross-linking agent for thermoplastic urethanes, polyester plasticizers, paints and coatings.
1,4-Butanediol (BDO) undergoes dehydration in the presence of phosphoric acid yielded teterahydrofuran, which is an important solvent used for various applications.
1,4-Butanediol (BDO) acts an intermediate and is used to manufacture polytetramethylene ether glycol (PTMEG), polybutylene terephthalate (PBT) and polyurethane (PU).
1,4-Butanediol (BDO) finds application as an industrial cleaner and a glue remover.
1,4-Butanediol (BDO) 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).
1,4-Butanediol (BDO) is a solvent with good antimicrobial action.
1,4-Butanediol (BDO) enhances the preservative activity of parabens.
Butylene glycol also serves as a humectant and viscosity controller, and to mask odor.
1,4-Butanediol (BDO) is used to produce polybutyleneterephthalate, a thermoplastic polyester;and in making tetrahydrofuran, butyrolactones,and polymeric plasticizers.
Industrial use
1,4-Butanediol (BDO) is used industrially as a solvent and in the manufacture of some types of plastics, elastic fibers and polyurethanes.
In organic chemistry, 1,4-butanediol is used for the synthesis of γ-butyrolactone (GBL).
In the presence of phosphoric acid and high temperature, it dehydrates to the important solvent tetrahydrofuran.
At about 200 °C in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone.
1,4-Butanediol (BDO) is used to synthesize 1,4-Butanediol diglycidyl ether which is then used as a reactive diluent for epoxy resins.
1,4-Butanediol (BDO) is used in the production of polybutylene terephthalate (PBT) plastic.
World production of 1,4-Butanediol (BDO) was claimed to be about one million metric tons per year and market price is about US$ 2,000 (€1,600) per ton (2005).
In 2013, worldwide production was claimed to be billions of pounds (consistent with approximately one million metric tons).
Almost half of 1,4-Butanediol (BDO) is dehydrated to tetrahydrofuran to make fibers such as Spandex.
The largest producer is BASF.
Reactivity Profile
1,4-Butanediol (BDO) is heat and light sensitive.
1,4-Butanediol (BDO) reacts with acid chlorides, acid anhydrides and chloroformates; reacts with oxidizing agents and reducing agents.
1,4-Butanediol (BDO) is incompatible with isocyanates and acids; also incompatible with peroxides, perchloric acid, sulfuric acid, hypochlorous acid, nitric acid, caustics, acetaldehyde, nitrogen peroxide and chlorine.
