Gamma Butyrolactone

Gamma Butyrolactone Basic information
Chemical properties Uses Production Category Toxicity grading Acute toxicity Hazardous characteristics of the explosive Flammability hazard Storage and transportation properties Extinguishing agent
Product Name:Gamma Butyrolactone
Synonyms:Gamma-Aminobutyric acid(GABA);4-Hydroxybutyric acid-gama-lactone;GAMMA-BUTYROLACTONE, REAGENTPLUS, >=99%;4-HYDROXYBUTANOIC ACID LACTONE 98+% &;GAMMA-BUTYROLACTONE, 99+%;T-Butyrolactone;CadionGr;GAMMA-BUTYROLACTONE,1.0MG/MLINMETHANOL
CAS:96-48-0
MF:C4H6O2
MW:86.09
EINECS:202-509-5
Product Categories:GBL;organic interme;Pharmaceutical Intermediates;Heterocycles;Miscellaneous Reagents;Halogenated Heterocycles ,Thiophenes ,Thiazolines/Thiazolidines
Mol File:96-48-0.mol
Gamma Butyrolactone Structure
Gamma Butyrolactone Chemical Properties
Melting point -45 °C (lit.)
Boiling point 204-205 °C (lit.)
density 1.12 g/mL at 25 °C (lit.)
vapor density 3 (vs air)
vapor pressure 1.5 mm Hg ( 20 °C)
refractive index n20/D 1.436(lit.)
FEMA 3291 | 4-HYDROXYBUTANOIC ACID LACTONE
Fp 209 °F
storage temp. 2-8°C
solubility DMF: 10 mg/ml; DMSO: 10 mg/ml; Ethanol: 10 mg/ml; PBS (pH 7.2): 1 mg/ml
form neat
color Clear colorless
Odorat 100.00 %. creamy oily fatty caramel
PH Range4 at 100 g/l at 20 °C
Odor Typecreamy
explosive limit16%
Water Solubility MISCIBLE
Merck 13,1596
JECFA Number219
BRN 105248
Stability:Stable. Hygroscopic. Incompatible with strong oxidizing agents, strong acids, strong bases, strong reducing agents.
InChIKeyYEJRWHAVMIAJKC-UHFFFAOYSA-N
LogP-0.566 at 25℃
CAS DataBase Reference96-48-0(CAS DataBase Reference)
IARC3 (Vol. 11, Sup 7, 71) 1999
NIST Chemistry Reference«gamma»-Butyrolactone(96-48-0)
EPA Substance Registry System.gamma.-Butyrolactone (96-48-0)
Safety Information
Hazard Codes Xn,F
Risk Statements 22-36-67-41-20/21/22-11
Safety Statements 26-36-39-36/37-16
WGK Germany 1
RTECS LU3500000
Autoignition Temperature851 °F
TSCA Yes
HS Code 29322980
Hazardous Substances Data96-48-0(Hazardous Substances Data)
ToxicityLD50 orally in rats: 17.2 ml/kg (Smyth)
MSDS Information
ProviderLanguage
BLO English
SigmaAldrich English
ACROS English
Gamma Butyrolactone Usage And Synthesis
Chemical propertiesGamma-Butyrolactone (GBL) is a colorless oily liquid. It is miscible with water and the general organic and slightly soluble in aliphatic hydrocarbons. GBL has been characterized as having an intense bitter taste with faint to pleasant odor.
UsesGamma-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.
ProductionMaleic anhydride hydrogenation method is an advanced technology developed in 1970s. It can produce tetrahydrofuran and γ-butyrolactone in any proportion with a hydrogenation reaction, and the usual ratio is tetrachlorofuran: γ-butyrolactone = 3-4:1.
There are many production enterprises, but usually in small scale. The average level is 300t/a. The production capacity account for 30% of the total domestic production capacity.  2.1, 4-butanediol dehydrogenation reactor is a tube array reactor, filled with flake copper catalyst (with zinc oxide as the carrier). The reaction temperature is controlled at 230-240 ° C. The yield of the product is obtained by reduced pressure distillation of and the yield is above 77%.
CategoryFlammable substance
Toxicity gradingMiddle
Acute toxicityoral-rat LD50: 1540 mg/kg; oral-mouse LD50: 1720 mg/kg
Hazardous characteristics of the explosiveExplosible when react with butanol, 2,4-dichlorophenol and sodium hydroxide
Flammability hazardFlammable in case of heat, open flame; being able to react with oxidant; releasing toxic pungent smoke when in the process of pyrolysis.
Storage and transportation propertiesMake sure ventilating, low temperature and drying in the warehouse; separate from the oxidant; prevent fires.
Extinguishing agentDry powder, carbon dioxide, foam
DescriptionDihydro-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.
Chemical Propertiesγ-Butyrolactone is oily, colorless, clear liquid. It has a faint, sweet, aromatic, slightly buttery odor.
Gamma-butyrolactone
γ-Butyrolactone is a lactone. It is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. Under acidic conditions it forms an equilibrium mixture of both compounds. These compounds then may go on to form a polymer.
OccurrenceReported found as a constituent in coffee aroma; a volatile flavor component in roasted filberts as well. Also reported found in tomato, potato, soybeans, beans, vinegar, mushrooms, roasted chicken, beef, cider, beer, wine, scallops and clams.
UsesFor the introduction of 3-carboxypropyl side chain. Used as a component of electrolyte solutions in batteries and capacitors.
Usesr-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.
UsesIntermediate 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.
DefinitionChEBI: A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.
Preparationγ-Butyrolactone is produced by gas phase 1,4-butanediol under the action of Cu catalyst to produce product γ-butyrolactone and by-product hydrogen. Crude γ-Butyrolactone is purified to remove light and heavy components, with a purity of more than 99.5%, as an export product. At the same time, the by-product hydrogen is sent to other hydrogenation processes for recycling after removing CO and CO2 through the methanation process.
Aroma threshold valuesDetection: 20 to 50 ppm
Taste threshold valuesTaste characteristic at 75 ppm: milky, creamy with fruity peach-like afternotes.
General DescriptionClear colorless oily liquid with a pleasant odor.
Air & Water ReactionsHygroscopic. Soluble in water.
Reactivity Profilegamma-Butyrolactone can react with oxidizing materials, inorganic acids and bases, alcohols and amines. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. gamma-Butyrolactone is volatile with steam. . The combination of the lactone, butanol, 2,4-dichlorophenol, and sodium hydroxide in the attempted synthesis of 2,4-dichlorophenoxybutyric acid caused a thermal runaway reaction that eventually exploded, [CISHC Chem. Safety Summ., 1977, 48, 3].
HazardToxic by ingestion. Questionable carcino- gen.
Fire Hazardgamma-Butyrolactone is combustible.
Biochem/physiol ActionsPrecursor of γ-hydroxybutyric acid (GHB). It blocks dopamine release by blocking impulse flow in dopaminergic neurons. Pretreatment with γ-butyrolactone allows detection of autoreceptor-induced dopamine release.
Safety ProfileModerately toxic by ingestion, intravenous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental tumorigenic data by skin contact. Mutation data reported. Less acutely toxic than ppropiolactone. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, alcohol foam, CO2, dry chemical. Potentially explosive reaction with butanol + 2,4 dichlorophenol + sodium hydroxide. When heated to decomposition it emits acrid and irritating fumes.
Potential ExposureUsed as a chemical intermediate for making other chemicals, including pesticides, cosmetics, and pharmaceuticals; as a solvent for paint, nail polish removers, and industrial chemicals. Used in electronics, drilling and petroleum industries as a stabilizer and solvent. Used as a flavoring agent in various foods and beverages, including grains and breakfast foods, candy, and alcoholic and nonalcoholic drinks. Drug of abuse: the United States Food and Drug Administration has warned the public not to purchase or consume products, containing gamma-butyrolactone (GBL). FDA has also asked the companies that manufacture these products to voluntarily recall them. The agency has received reports of serious health problems—some that are potentially life-threatening—associated with the use of these products. Although labeled as dietary supplements and marketed under various brand names, these products are illegally marketed unapproved new drugs. False advertising claims include building muscles, improved physical performance, enhanced sex, reduced stress and induced sleep
ShippingListed by some sources as unregulated. UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1—Poisonous materials, Technical Name Required.
Purification MethodsDry the lactone over anhydrous CaSO4, then fractionally distil it. Handle it in a fume cupboard due to its TOXICITY. [Beilstein 17 V 7.]
Incompatibilities4-Butyrolactone is incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, alcohols, amines, strong and inorganic acids, strong bases. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. It is hygroscopic and volatile with steam. Combustible; vapor may form explosive mixture with air.
Waste DisposalUse a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. All federal, state, and local environmental regulations must be observed.
BETA-BUTYROLACTONE Erythromycin Estolate TRIOXSALEN (-)-Corey lactone diol Acetic anhydride 4-Aminobutyric acid Maleic anhydride Indole-3-butyric acid Isobutyric acid Di-tert-butyl dicarbonate 6-Amino-4-hydroxy-2-naphthalenesulfonic acid Succinic anhydride 2,3,4-Trihydroxybenzoic acid 4-Cyanophenol Cyclobutane-1,2,3,4-tetracarboxylic dianhydride Phthalic anhydride Glutaric anhydride Gamma Butyrolactone

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