1,4-Butanediol

Base Information

• Chemical Name: 1,4-Butanediol
• CAS No.: 110-63-4
• Deprecated CAS: 732189-03-6,1204746-06-4,1400594-63-9,1400594-63-9
• Molecular Formula: C4H10O2
• Molecular Weight: 90.1222
• Hs Code.: 2905399090
• European Community (EC) Number: 203-786-5,615-930-8
• ICSC Number: 1104
• NSC Number: 406696
• UNII: 7XOO2LE6G3
• DSSTox Substance ID: DTXSID2024666
• Nikkaji Number: J5.097K
• Wikipedia: 1,4-Butanediol
• Wikidata: Q161521
• Metabolomics Workbench ID: 56409
• ChEMBL ID: CHEMBL171623
• Mol file: 110-63-4.mol

Synonyms:1,4-butanediol;1,4-butylene glycol

Chemical Property of 1,4-Butanediol

Chemical Property:

• Appearance/Colour: viscous colourless liquid
• Vapor Pressure: 0.015mmHg at 25°C
• Melting Point: 20 °C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 227.999 °C at 760 mmHg
• PKA: 14.73±0.10(Predicted)
• Flash Point: 105.909 °C
• PSA: 40.46000
• Density: 1.006 g/cm³
• LogP: -0.24880
• Water Solubility.: Miscible
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 90.068079557
• Heavy Atom Count: 6
• Complexity: 17.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R22:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C(CCO)CO
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system. This may result in narcosis.
• Sources and Categories: 1,4-Butanediol (1,4-BDO) is a tetracarbon diol and an important commodity chemical. It is synthesized through various chemical processes and can also be produced bio-based approaches. It serves as a platform chemical for the synthesis of various chemicals and materials, including polyesters, polyurethanes, tetrahydrofuran, and γ-butyrolactone.
• Market Data: In 2015, the total market size for chemicals and polyesters manufactured using 1,4-BDO as a raw material was valued at over USD 6.19 billion. It is a significant commodity chemical with a growing market.
• Mechanism of Action: 1,4-Butanediol serves as a precursor in various chemical reactions for the synthesis of polyurethanes, polyesters, and other chemicals.
• Industrial Applications: Used in the synthesis of polyurethane elastomers, polyesters (PBT, PBAT), spandex fibers, and special-purpose coatings. Also employed as organic solvents and raw materials for organic synthesis.; Common co-monomer in various polyesters, such as polybutylene terephthalate (PBT) and polybutylene adipate terephthalate (PBAT).
• Production Methods: Chemical catalysis processes such as hydrogenation of maleic anhydride, isomerization of propylene oxide, acetoxylation of butadiene, and reaction between formaldehyde and acetylene are the main industrial methods for 1,4-BDO production.; Recent trends involve utilizing renewable sources such as biomass for production, including de novo biosynthesis and biocatalysis in engineered microorganisms like Escherichia coli. Bio-based methods for 1,4-BDO production involve catalytic hydrogenation or bio-conversion of sugars, succinic acid, and furfural. These methods offer sustainability benefits and competitiveness in the post-petroleum era.

Technology Process of 1,4-Butanediol

There total 314 articles about 1,4-Butanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1,4-dihydroxybut-2-yne (110-65-6) → Butane-1,4-diol (110-63-4) + 1,4-butenediol (6117-80-2)

Guidance literature:

With hydrogen; copper-palladium; silica gel; In ethanol; at 25 ℃; under 760 Torr; Kinetics;

DOI:10.1021/jo001246p

Reference yield: 98.0%

dimethyl cis-but-2-ene-1,4-dioate (624-48-6) → tetrahydrofuran (109-99-9,24979-97-3,77392-70-2) + 2-methoxytetrahydrofuran (13436-45-8) + 4-butanolide (96-48-0) + propan-1-ol (71-23-8) + 2-(4'-hydroxybutoxy)-tetrahydrofuran (64001-06-5) + Butane-1,4-diol (110-63-4) + butan-1-ol (71-36-3)

Guidance literature:

With hydrogen; copper catalyst, T 4489, Sud-Chemie AG, Munich; at 150 - 280 ℃; under 187519 Torr; Neat liquid(s) and gas(es)/vapour(s);

Reference yield: 85.0%

1-(phenylmethyl)-2,5-pyrrolidinedione (2142-06-5) → Butane-1,4-diol (110-63-4) + benzylamine (100-46-9)

Guidance literature:

With C₂₅H₁₉BrMnN₂O₂P; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 130 ℃; for 48h; under 22502.3 Torr; Inert atmosphere; Glovebox; Autoclave; Green chemistry;

DOI:10.1039/d0gc00570c

upstream raw materials:

2,5-dihydrofuran

maleic anhydride

1,4-dibromo-butane

1,4-dihydroxybut-2-yne

Downstream raw materials:

2-phenyl-1,3,2-dioxaphosphepin-2-oxide

2-phenyl-[1,3]dioxepane

1,4-bis-phenylcarbamoyloxy-butane

1-ethylpyrrolidine

Refernces

• 1、 Huang, Zhiwei,Barnett, Kevin J.,Chada, Joseph P.,Brentzel, Zachary J.,Xu, Zhuoran,Dumesic, James A.,Huber, George W.. "Hydrogenation of γ-Butyrolactone to 1,4-Butanediol over CuCo/TiO2 Bimetallic Catalysts". . p. 8429 - 8440. Retrieved 2017.
• 2、 Yamaguchi, Aritomo,Hiyoshi, Norihito,Sato, Osamu,Bando, Kyoko K.,Masuda, Yoshio,Shirai, Masayuki. "Thermodynamic equilibria between polyalcohols and cyclic ethers in high-temperature liquid water". . p. 2666 - 2668. Retrieved 2009.
• 3、 Dyson,Ellis,Welton. "A temperature-controlled reversible ionic liquid - Water two phase - Single phase protocol for hydrogenation catalysis". . p. 705 - 708. Retrieved 2001.
• 4、 Chickos, James S.,Uang, Jack Y.-J.,Keiderling, Tim A.. "A Study of the Catalytic Deuteration of 1,4-Butynediol". . p. 2594 - 2596. Retrieved 1991.
• 5、 Rode,Tayade,Nadgeri,Jaganathan,Chaudhari. "Continuous hydrogenation of 2-butyne-1,4-diol to 2-butene- and butane-1,4-diols". . p. 278 - 284. Retrieved 2006.
• 6、 Kingsbury, Celia L.,Smith, Robin A. J.. "Effect of Ethers on Reactions of Butylcoppers with α,β-Unsaturated Ketones in Toluene". . p. 7637 - 7643. Retrieved 1997.
• 7、 Li, Haomeng,Wang, Xinkui,Chen, Xiao,Li, Chuang,Wang, Min,Yi, Yanhui,Ji, Min,Wang, Huilong,Shao, Zhengfeng,Liang, Changhai. "A Schiff Base Modified Pd Catalyst for Selective Hydrogenation of 2-Butyne-1,4-diol to 2-Butene-1,4-diol". . p. 2150 - 2157. Retrieved 2020.
• 8、 Ryu, Jaeyune,Wuttig, Anna,Surendranath, Yogesh. "Quantification of Interfacial pH Variation at Molecular Length Scales Using a Concurrent Non-Faradaic Reaction". . p. 9300 - 9304. Retrieved 2018.
• 9、 Kaneda, Kiyotomi,Imanaka, Toshinobu,Teranishi, Shiichiro. "DIRECT SYNTHESIS OF 1,4-BUTANEDIOL FROM ALLYL ALCOHOL USING CARBON MONOXIDE AND WATER IN THE PRESENCE OF Rh6(CO)16-PROPANEDIAMINE SYSTEM". . p. 1465 - 1466. Retrieved 1983.
• 10、 Maniar,Kalonia,Simonelli. "Alkaline hydrolysis of oligomers of tartrate esters: Effect of a neighboring carboxyl on the reactivity of ester groups". . p. 705 - 709. Retrieved 1992.