gamma-Butyrolactone

Base Information

• Chemical Name: gamma-Butyrolactone
• CAS No.: 96-48-0
• Deprecated CAS: 187997-16-6
• Molecular Formula: C4H6O2
• Molecular Weight: 86.0904
• Hs Code.: 2932.29
• European Community (EC) Number: 202-509-5,923-610-7,694-612-0
• ICSC Number: 1020
• NSC Number: 4592
• UNII: OL659KIY4X
• DSSTox Substance ID: DTXSID6020224
• Nikkaji Number: J3.971C
• Wikipedia: Gamma-Butyrolactone
• Wikidata: Q79739
• ChEMBL ID: CHEMBL95681
• Mol file: 96-48-0.mol

Synonyms:1,4 Butanolide;1,4-Butanolide;4 Butyrolactone;4 Hydroxybutyric Acid Lactone;4-Butyrolactone;4-Hydroxybutyric Acid Lactone;Dihydro-2(3H)-furanone;Furanone, tetrahydro 2;Furanone, tetrahydro-2-;gamma Butyrolactone;gamma-Butyrolactone;Lactone, 4-Hydroxybutyric Acid

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of gamma-Butyrolactone

Chemical Property:

• Appearance/Colour: colourless oily liquid
• Vapor Pressure: 1.5 mm Hg ( 20 °C)
• Melting Point: -45 °C(lit.)
• Refractive Index: 1.436-1.437
• Boiling Point: 204 °C at 760 mmHg
• Flash Point: 80.9 °C
• PSA: 26.30000
• Density: 1.128 g/cm³
• LogP: 0.32340
• Storage Temp.: 2-8°C
• Water Solubility.: MISCIBLE
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 86.036779430
• Heavy Atom Count: 6
• Complexity: 67.9

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,F
• Statements: 22-36-67-41-20/21/22-11
• Safety Statements: 26-36-39-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Lactones
• Canonical SMILES: C1CC(=O)OC1
• Recent ClinicalTrials: Effect of Yong Chong Cao Capsule on Outcomes in Patients With Mild to Severe COPD
• 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 is severely irritating to the eyes. Ingestion could cause effects on the central nervous system. This may result in excitement and central nervous system depression. Exposure at high concentrations could cause respiratory failure, convulsions and unconsciousness.
• Uses: Gamma-Butyrolactone (GBL) has widespread industrial use. It is a common solvent found in paint strippers, nail polish removers, stain removers and circuit board cleaners. It is also a common intermediate in industrial chemistry including the manufacture of pyrrolidones and in some pharmaceuticals. Gamma-Butyrolactone is an important organic synthesis intermediate which can be used to synthesize indole butyric acid, butyric acid, succinic acid, α-pyrrolidone, N-methylpyrrolidone, vinyl pyrrolidone, acetyl-γ-butyrolactone, cyclopropylamine, ciprofloxacin, vitamin B1, chlorophyll and so on; It is a non-toxic high boiling point solvent with high solubility and safe and convenient usage and management; It is used as an extractant for butadiene, aromatic, advanced grease petroleum processing; It is used as an acrylonitrile fiber spinning solvent in the chemical fiber industry. It is a thinner and curing agent commonly used in wool, nylon, acrylonitrile and other fiber dyeing auxiliaries and other chemical industries. For the introduction of 3-carboxypropyl side chain. Used as a component of electrolyte solutions in batteries and capacitors. r-butyrolactone is one kind of important fine chemicalintermediate, simultaneously also is one kind of performance fine highboiling point solvent, ideal antioxidant, plasticizer,extracting agent, absorbent, dispersing agent, solid stain, Coagulation Reagent. Intermediate in the synthesis of polyvinylpyrrolidone, DL-methionine, piperidine, phenylbutyric acid, thiobutyric acids. Solvent for polyacrylonitrile, cellulose acetate, methyl methacrylate polymers, polystyrene. Constituent of paint removers, textile aids, drilling oils.
• Description: Dihydro-2(3H)-furanone. An endogenous neuroregulator made from gamma-amino butyrate and the precursor of gamma hydroxybutyrate. It causes selective increase of brain dopamine by inhibiting its release from nerve terminals. The compound has sedative properties at low doses and produces surgical anesthesia at high doses. It is also used as an industrial solvent and precursor.

Technology Process of gamma-Butyrolactone

There total 380 articles about gamma-Butyrolactone 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: 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: 82.0%

Butane-1,4-diol (110-63-4) → 4-butanolide (96-48-0) + 4-chlorobutyraldehyde (6139-84-0)

Guidance literature:

With tetrachloromethane; bis(acetylacetonate)oxovanadium; at 100 ℃; for 1h;

DOI:10.1023/A:1021668011691

Reference yield: 79.1%

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) + 1-methoxy-1,4-butanediol + 2-(4'-hydroxybutoxy)-tetrahydrofuran (64001-06-5) + 4-hydroxy-butanoic acid 4-hydroxybutyl ester + Butane-1,4-diol (110-63-4) + 4-hydroxybutyraldehyde (25714-71-0) + methyl 4-hydroxybutanoate (925-57-5) + butan-1-ol (71-36-3)

Guidance literature:

With hydrogen; at 190 ℃; under 46504.7 Torr; Gas phase;

upstream raw materials:

tetrahydrofuran

2-hydroperoxytetrahydrofuran

lead(IV) tetraacetate

maleic anhydride

Downstream raw materials:

4-piperidin-1-yl-butan-1-ol

(E)-α-(2-furylmethylene)-γ-butyrolactone

α-(3-phenyl-2-propenylidene)-γ-butyrolactone

Methyl 4-bromobutyrate

Refernces

• 1、 Li, Zhanchong,Wu, Liangying,Guo, Jiabao,Shao, Yifei,Song, Yang,Ding, Yuzhou,Zhu, Li,Yao, Xiaoquan. "Light-Promoted Minisci Coupling Reaction of Ethers and Aza Aromatics Catalyzed by Au/TiO2 Heterogeneous Photocatalyst". . p. 3671 - 3678. Retrieved 2021.
• 2、 Friess,Frankenburg. "-". . p. 2679. Retrieved 1952.
• 3、 Amorati, Riccardo,Baschieri, Andrea,Morroni, Gloria,Gambino, Rossana,Valgimigli, Luca. "Peroxyl Radical Reactions in Water Solution: A Gym for Proton-Coupled Electron-Transfer Theories". . p. 7924 - 7934. Retrieved 2016.
• 4、 Chung, Sang-Ho,Eom, Hee-Jun,Kim, Min-Sung,Lee, Myung Suk,Lee, Kwan-Young. "Highly dispersed ruthenium nanoparticle-embedded mesoporous silica as a catalyst for the production of γ-butyrolactone from succinic anhydride". . p. 7701 - 7706. Retrieved 2013.
• 5、 Zhidkova, N. V.,Kobryanskii, V. M.,Turovskaya, L. M.. "REACTION OF SPIRO ORTHO ESTERS WITH POLAR REAGENTS". . p. 1462 - 1465. Retrieved 1986.
• 6、 Glotova, Tatyana E.,Dvorko, Marina Yu.,Ushakov, Igor A.,Shabalin, Dmitrii A.,Schmidt, Elena Yu.,Trofimov, Boris A.. "Modification of γ-aminobutyric Acid with Acylacetylenes: Stereoselective C-Vinylation of the Primary Adducts and Transformation to Acylpyridines". . p. 314 - 316. Retrieved 2012.
• 7、 Al-Shaal, Mohammad Ghith,Calin, Marc,Delidovich, Irina,Palkovits, Regina. "Microwave-assisted reduction of levulinic acid with alcohols producing γ-valerolactone in the presence of a Ru/C catalyst". . p. 65 - 68. Retrieved 2016.
• 8、 Padmalatha, Patnam,Khatri, Praveen K.,Jain, Suman L.. "Selenium-doped TiO2 as an efficient photocatalyst for the oxidation of tetrahydrofuran to γ-butyrolactone using hydrogen peroxide as oxidant". . p. 1405 - 1409. Retrieved 2013.
• 9、 Zhang, Chi,Chen, Lifang,Cheng, Hongye,Zhu, Xuedong,Qi, Zhiwen. "Atomically dispersed Pd catalysts for the selective hydrogenation of succinic acid to γ-butyrolactone". . p. 55 - 61. Retrieved 2016.
• 10、 Oka. "-". . p. 12. Retrieved 1961.