GBL (Gamma-butyrolactone)

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γ-Butyrolactone (GBL) or gamma-butyrolactone is an organic compound with the formula O=CO(CH2)3. This is a hygroscopic, colorless, water-miscible liquid with a pleasant odor. It is the simplest 4-carbon lactone. It is mainly used as an intermediate in the production of other chemicals, such as N-methyl-2-pyrrolidone.[5] In humans, GBL acts as a prodrug for gamma-hydroxybutyric acid (GHB) and is often used as a recreational drug. GHB acts as a central nervous system (CNS) depressant with effects similar to those of barbiturates.[6]

Occurrence

GBL has been found in extracts from samples of unadulterated wines.[7][8] This finding indicates that GBL is a naturally occurring component in some wines and may be present in similar products. The concentration detected was approximately 5 μg/mL and was easily observed using a simple extraction technique followed by GC/MS analysis. GBL can be found in cheese flavorings but typically results in a content of 0.0002% GBL in the final foodstuff.[9]

Production and synthesis

γ-Butyrolactone is produced industrially by dehydrogenation of 1,4-butanediol at a temperature of 180–300 °C and atmospheric pressure in the presence of a copper catalyst.[5]

The yield of this process is approximately 95%. The purification takes place with a liquid-gas-phase extraction.[5] In the laboratory, it may also be obtained via the oxidation of tetrahydrofuran (THF), for example with aqueous sodium bromate.[10] An alternative route proceeds from GABA via a diazonium intermediate.[11]

Reactions

As a lactone, GBL is hydrolyzed under basic conditions, for example in a sodium hydroxide solution into sodium gamma-hydroxybutyrate, the sodium salt of gamma-hydroxybutyric acid. In acidic water, a mixture of the lactone and acid forms exists in an equilibrium. These compounds then may go on to form the polymer poly(4-hydroxybutyrate) as well as the dimer 1,6-Dioxecane-2,7-dione. When treated with a non-nucleophilic base, such as lithium diisopropylamide, GBL undergoes deprotonation of the alpha carbon atom to the carbonyl.Buy Best GBL Wheel Cleaner

Polymerization

The ring-opening polymerization of butyrolactone gives polybutyrolactone. The resulting reverts to the monomer by thermal cracking.[12][13] It is claimed that poly(GBL) is competitive with commercial biomaterial poly(4-hydroxybutyrate), or P4HB. It is further claimed that poly(GBL) is cheaper to make than P4HB, although both are bio-derived.[12][14]

Uses

Gamma-Butyrolactone is used as a chemical solvent and a cleaning agent,[15] for example in paint stripping or for cleaning graffiti.[16] Butyrolactone is a precursor to other chemicals. Reaction with methylamine gives NMP, and with ammonia gives pyrrolidone. It is also used as a solvent in lotions and some polymers.[5] 2-Methyl-4-chlorophenoxybutyric acid is an herbicide produced from butyrolactone.
Butyrolactone, with its wide liquid range, chemical stability, and high dielectric constant, is used in electrolytic capacitors as the organic solvent.[17] It has been used as a solvent in various laboratory experiments, e.g., the preparation of methylammonium lead halide.[18] Another discovered GBL utility is in the synthesis of nicotine (analogs):[19]

Pharmacology

Main article: gamma-hydroxybutyrate § Pharmacology
GBL is not active in its own right; its mechanism of action stems from its identity as a prodrug of GHB.

Pharmacokinetics

GBL is rapidly converted into GHB by paraoxonase (lactonase) enzymes, found in the blood.[20][21][22] Animals which lack these enzymes exhibit no effect from GBL.[21] GBL is more lipophilic (fat soluble) than GHB, and so is absorbed faster and has higher bioavailability. Because of these pharmacokinetic differences, GBL tends to be more potent and faster-acting than GHB, but has a shorter duration; whereas the related compound 1,4-butanediol (1,4-B) tends to be slightly less potent and slower to take effect but longer-acting than GHB.[23]

Quantity
1 L, 5 L, 15 L