| Identification | More | [Name]
gamma-Butyrolactone | [CAS]
96-48-0 | [Synonyms]
1,2-BUTANOLIDE
1,4-BUTANOLIDE
1,4-BUTYROLACTONE
4-Butanolide
4-BUTYROLACTONE
4-HYDROXBUTYRIC ACID LACTONE
4-HYDROXYBUTANOIC ACID LACTONE
4-HYDROXYBUTYRIC ACID GAMMA-LACTONE
4-HYDROXYBUTYRIC ACID LACTONE
4-HYROXYBUTYRIC ACID LACTONE
BLO
BUTYROLACTONE
BUTYROLACTONE,GAMMA-
endo-cis-5-norbornene-endo-2,3-dicarboxylic anhydride
FEMA 3291
GAMA-BUTYROLACTONE
GAMMA-BUTYROLACTONE
GAMMA-HYDROXYBUTYRIC ACID LACTONE
GBL
GBL-EL | [EINECS(EC#)]
202-509-5 | [Molecular Formula]
C4H6O2 | [MDL Number]
MFCD00005386 | [Molecular Weight]
86.09 | [MOL File]
96-48-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Oily, colorless, clear liquid. Faint, pleasant
odor. | [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)
| [FEMA ]
3291 | [refractive index ]
n20/D 1.436(lit.)
| [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 | [Odor]
at 100.00 %. creamy oily fatty caramel | [PH Range]
4 at 100 g/l at 20 °C | [Stability:]
Stable. Hygroscopic. Incompatible with strong oxidizing agents, strong acids, strong bases, strong reducing agents. | [explosive limit]
16% | [Odor Type]
creamy | [Water Solubility ]
MISCIBLE | [JECFA Number]
219 | [Merck ]
13,1596 | [BRN ]
105248 | [Dielectric constant]
40.960000000000001 | [InChIKey]
YEJRWHAVMIAJKC-UHFFFAOYSA-N | [LogP]
-0.566 at 25℃ | [CAS DataBase Reference]
96-48-0(CAS DataBase Reference) | [IARC]
3 (Vol. 11, Sup 7, 71) 1999 | [NIST Chemistry Reference]
«gamma»-Butyrolactone(96-48-0) | [EPA Substance Registry System]
96-48-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S39:Wear eye/face protection . | [WGK Germany ]
1
| [RTECS ]
LU3500000
| [Autoignition Temperature]
851 °F | [TSCA ]
Yes | [HS Code ]
29322980 | [Safety Profile]
Moderately 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. | [Hazardous Substances Data]
96-48-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 17.2 ml/kg (Smyth) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Tetrahydrofuran-->Hydrogen-->CIS-BUTENEDIOIC ANHYDRIDE-->Succinic anhydride-->1,4-Butanediol | [Preparation Products]
Tetrahydrofuran-->N-Methyl-2-pyrrolidone-->METHYL 3-(2,2-DICHLOROVINYL)-2,2-DIMETHYL-(1-CYCLOPROPANE)CARBOXYLATE-->Sorbic acid-->Cyclopropylamine-->Glutaric acid-->ethyl 3-(2,2-dichlorovinyl)-2,2-dimethyl-1-cyclopropanecarboxylate-->Cyclopropanecarboxylic acid-->4-Phenylbutyric acid-->GAMMA-CHLOROBUTYROPHENONE-->3-Acetyl-1-propanol-->1-Tetralone-->2-Pyrrolidinone-->3,3,4,4-diphenylsulfonetetracarboxylicdianhydride-->2-Acetylbutyrolactone-->Calcium D-Pantothenate-->4-(2-OXO-1,3-BENZOXAZOL-3(2H)-YL)BUTANOIC ACID-->Indole-3-butyric acid-->2,6-Difluorobenzonitrile-->ALPHA,ALPHA-DIMETHYL-GAMMA-BUTYROLACTONE-->4-Chlorobutyryl chloride-->4-Bromo-2,2-diphenylbutyric acid-->3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2，2-dimethyl cyclopropane carboxylic acid-->Haloperidol-->2-Bromo-4-butanolide-->SODIUM 4-HYDROXYBUTYRATE |
| Hazard Information | Back Directory | [General Description]
Clear colorless oily liquid with a pleasant odor. | [Reactivity Profile]
4-BUTYROLACTONE(96-48-0) can react with oxidizing materials, inorganic acids and bases, alcohols and amines. Rapidly hydrolyzed by bases and slowly hydrolyzed by acids. 4-BUTYROLACTONE(96-48-0) 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]. | [Air & Water Reactions]
Hygroscopic. Soluble in water. | [Hazard]
Toxic by ingestion. Questionable carcino-
gen.
| [Potential Exposure]
Used 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 | [Fire Hazard]
This chemical is combustible. | [First aid]
Eyes: first check the victim for contact lenses
and remove if present. Flush victim’s eyes with water
or normal saline solution for 20 to 30 minutes.
Simultaneously, call a hospital or poison control center.
Do not put any ointments, oils, or medication in the victim’s eyes without specific instructions from a physician.
Immediately transport the victim after flushing eyes to a
hospital even if no symptoms (such as redness or irritation) develop. Skin: immediately flood affected skin with
water while removing and isolating all contaminated
clothing. Gently wash all affected skin areas thoroughly
with soap and water. If symptoms such as redness or irritation develop, immediately call a physician and be prepared to transport the victim to a hospital for treatment.
Inhalation: immediately leave the contaminated area; take
deep breaths of fresh air. If symptoms (such as wheezing,
coughing, shortness of breath, or burning in the mouth,
throat, or chest) develop, call a physician and be preparedto transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, SCBA should be used; if not
available, use a level of protection greater than or equal
to that advised under protective clothing. Ingestion: do
not induce vomiting. If the victim is conscious and not
convulsing, give 1 or 2 glasses of water to dilute the
chemical and immediately call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is
convulsing or unconscious, do not give anything by
mouth, ensure that the victim’s airway is open and lay
the victim on his/her side with the head lower than the
body. Do not induce vomiting. Immediately transport the
victim to a hospital. | [Shipping]
Listed by some sources as unregulated. UN2810
Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels:
6.1—Poisonous materials, Technical Name Required. | [Incompatibilities]
4-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. | [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. | [Waste Disposal]
Use 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. | [Occurrence]
Reported 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. | [Definition]
ChEBI: A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2. | [Preparation]
From acetylene and formaldehyde, also from a number of alternative sources; ethylene chlorohydrin, glutamic acid,
γ-hydroxybutyric acid solutions, tetrahydrofuran, vinyl-acetic acid. | [Aroma threshold values]
Detection: 20 to 50 ppm | [Taste threshold values]
Taste characteristic at 75 ppm: milky, creamy with fruity peach-like afternotes. | [Biochem/physiol Actions]
Precursor 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. | [Purification Methods]
Dry the lactone over anhydrous CaSO4, then fractionally distil it. Handle it in a fume cupboard due to its TOXICITY. [Beilstein 17 V 7.] |
| Questions And Answer | Back Directory | [Chemical properties]
Gamma-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. | [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.
| [Production]
Maleic 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%. | [Category]
Flammable substance | [Toxicity grading]
Middle | [Acute toxicity]
oral-rat LD50: 1540 mg/kg; oral-mouse LD50: 1720 mg/kg | [Hazardous characteristics of the explosive]
Explosible when react with butanol, 2,4-dichlorophenol and sodium hydroxide | [Flammability hazard]
Flammable 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 properties]
Make sure ventilating, low temperature and drying in the warehouse; separate from the oxidant; prevent fires. | [Extinguishing agent]
Dry powder, carbon dioxide, foam |
|