1,4-Butanediol
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| 1,4-Butanediol | |
|---|---|
| |
| Image:1,4-butanediol-Space-filling.png | |
| IUPAC name | 1,4-Butanediol |
| Identifiers | |
| CAS number | |
| SMILES | OCCCCO |
| Properties | |
| Molecular formula | C4H10O2 |
| Molar mass | 90.12 g/mol |
| Density | 1.010 g/cm³ |
| Melting point |
20 °C |
| Boiling point |
230 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
1,4-Butanediol is an alcohol derivative of the alkane butane, carrying two hydroxyl groups. It is a colorless viscous liquid.
Contents |
Synthesis
Its industrial synthesis starts with acetylene, which is reacted with two molecules of formaldehyde to form 1,4-butynediol, also known as but-2-yne-1,4-diol, a process known as the Reppe synthesis. This product is subsequently hydrogenated to give 1,4-butanediol.
It is also manufactured on an industrial scale by the vapour phase hydrogenation of maleate esters.
Uses
1,4-Butanediol is used industrially as a solvent and in the manufacture of some types of plastics and fibers. In organic chemistry, 1,4-butanediol is used for the synthesis of γ-butyrolactone (GBL). In the presence of phosphoric acid and high temperature, it dehydrates to the important solvent tetrahydrofuran.[1]. At about 200 °C in the presence of a soluble ruthenium catalyst, the diol loses H2 and forms butyrolactone.[1]
It is also used as a recreational drug known by some users as "One Comma Four", "One Four Bee" or "One Four B-D-O". It exerts effects similar to γ-hydroxybutyrate (GHB), which is a metabolic product of 1,4-butanediol.[1]
Anecdotal reports indicate that 1,4-butanediol produces a strong toxic feeling not present with GHB when ingested.[1][1] These reports also indicate that it may cause damage to the liver as well as to other vital organs.[1][1] Abuse has also resulted in addiction and death.[1][1][1]
Pharmacokinetics
1,4-Butandiol is converted into GHB by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase and differing levels of these enzymes may account for differences in effects and side effects between users.[1][1] Because these enzymes are also responsible for metabolizing alcohol there is a strong chance of a dangerous drug interaction.[1][1] Emergency room patients who overdose on both alcohol and 1,4-butanediol often present with symptoms of ethanol intoxication initially and as the ethanol is metabolized the 1,4-butandiol is then able to better compete for the enzyme and a second period of intoxication ensues as the 1,4-butanediol is converted into GHB.[1]
Pharmacodynamics
1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are due to the fact that it is metabolized into GHB, however there is some evidence that 1,4-butanediol may have inherent alcohol-like pharmacological effects that are not due to this conversion.[1]
Legality
While 1,4-butanediol is not currently scheduled federally in the United States, a number of states have classified 1,4-butanediol as a controlled substance and even where it has not yet been scheduled. Scheduling of 1,4-butanediol on a federal level is highly unlikely considering its common industrial use and many industrial applications.[citation needed]
