1,4-Butanediol

Chembox new
Name = 1,4-Butanediol
ImageFile1 = 1,4-butanediol.png ImageSize1 = 200px
ImageFile2 = 14bd3d.png ImageSize2 = 200px
ImageName = 1,4-Butanediol
IUPACName = Butan-1,4-diol
Section1 = Chembox Identifiers
CASNo = 110-63-4
SMILES = OCCCCO
Section2 = Chembox Properties
Formula = C₄H₁₀O₂
MolarMass = 90.12 g/mol
Density = 1.010 g/cm³
MeltingPt = 20 °C
BoilingPt = 230 °C

1,4-Butanediol is the organic compound with the formula HOCH₂CH₂CH₂CH₂OH. This colorless viscous liquid is derived from butane by placement of alcohol groups at each end of the chain. It is one of four stable isomers of butanediol.

ynthesis

In its industrial synthesis, acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol, also known as but-2-yne-1,4-diol. This type of process is illustrative of what is known as Reppe Chemistry. Hydrogenation of 1,4-butynediol gives 1,4-butanediol.

It can also be manufactured on an industrial scale by the vapour phase hydrogenation of the esters and anhydrides of maleic acid and succinic acid.

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.cite encyclopedia
title =Ethers, by Lawrence Karas and W. J. Piel | encyclopedia =Kirk‑Othmer Encyclopedia of Chemical Technology | volume = | pages = | publisher =John Wiley & Sons, Inc | date =2004 | id = | accessdate =2007-09-05] At about 200 °C in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone. [J. Zhao, J. F. Hartwig "Acceptorless, Neat, Ruthenium-Catalyzed Dehydrogenative Cyclization of Diols to Lactones" Organometallics 2005, volume 24, 2441-2446.]

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. [Satta R, Dimitrijevic N, Manev H. "Drosophila metabolize 1,4-butanediol into gamma-hydroxybutyric acid in vivo." Eur J Pharmacol. 2003 Jul 25;473(2-3):149-52. PMID 12892832] [Carai MA, Colombo G, Reali R, Serra S, Mocci I, Castelli MP, Cignarella G, Gessa GL. Central effects of 1,4-butanediol are mediated by GABA(B) receptors via its conversion into gamma-hydroxybutyric acid. "European Journal of Pharmacology". 2002 Apr 26;441(3):157-63. PMID 12063087]

Anecdotal reports indicate that 1,4-butanediol produces a strong toxic feeling not present with GHB when ingested.cite web | title = 1,4-Butanediol Toxicity | author = "Murple" | url = http://leda.lycaeum.org/?ID=15209 | publisher = The Lycaeum | accessdate = 2007-11-11] [cite web | title = Nasty Headache: 1,4 BD, GBL & 5-MeO-DiPT | author = "Itsuoda" | url = http://www.erowid.org/experiences/exp.php?ID=13226 | publisher = Erowid] These reports also indicate that it may cause damage to the liver as well as to other vital organs. [cite web | title = 1,4-Butanediol Toxicity? | author = "Andro" | url = http://www.erowid.org/experiences/exp.php?ID=1929 | publisher = Erowid] Abuse has also resulted in addiction and death. [Zvosec DL, Smith SW, McCutcheon JR, Spillane J, Hall BJ, Peacock EA. "Adverse events, including death, associated with the use of 1,4-butanediol." N Engl J Med. 2001 Jan 11;344(2):87-94. PMID 11150358] [cite web | title = 1,4-B is Not a Toy | author = Anonymous | url = http://www.erowid.org/experiences/exp.php?ID=10082| publisher = Erowid] [cite web | title = Definitely addictive: 1,4-Butanediol | author = "Elizabeth" | url = http://www.erowid.org/experiences/exp.php?ID=3317 | publisher = Erowid]

Pharmacokinetics

1,4-Butanediol 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.cite web | author = Theodore I Benzer, Scott Cameron, Christopher S Russi | title = Toxicity, Gamma-Hydroxybutyrate | date = 2007-01-08 | url = http://www.emedicine.com/emerg/topic848.htm | publisher = eMedicine] Because these enzymes are also responsible for metabolizing alcohol there is a strong chance of a dangerous drug interaction.cite journal
title = 1,4 Butanediol, gamma-hydroxybutyric acid and ethanol: relationships and interactions
author = Poldrugo, F.; Snead, O.C. 3rd.
journal = Neuropharmacology
volume = 59
issue = 23
pages = 109–113
year = 1984
doi =
pmid = 6717752] 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-butanediol 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.

2007 contamination of Bindeez toy

A toy called "Bindeez" ("Aqua Dots" in North America) was recalled by the distributor in November 2007 because of the presence of 1,4-butanediol. The toy consists of small beads that stick to each other by sprinkling water. 1,4-Butanediol, which is metabolized to gamma-hydroxybutyric acid "in vivo", was detected by GC-MS. [cite news | url = http://pubs.acs.org/cen/news/85/i46/8546news11.html | publisher = Chemical & Engineering News | title = Industrial Chemical Sullies Popular Children's Toy | author = Linda Wang | date = 2007-11-09] The production plant seems to have intended to cut costs by replacing 1,5-pentanediol. ChemNet China lists the price of 1,4 butanediol at between about US$1,350-$2,800 per metric ton, while the price for 1,5-pentanediol is about US$9,700 per metric ton. [cite news | author = Associated Press | title = US mother says her son began to stumble and vomit after eating Chinese-made toy, now recalled | publisher = International Herald Tribune | date = 2007 Nov 07]

Pharmacodynamics

1,4-Butanediol seems to have two types of pharmacological actions. The major psychoactive effects of 1,4-butanediol are because 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.

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. Scheduling of 1,4-butanediol on a federal level seems unlikely considering its legitimate industrial applications.Fact|date=February 2007

ee also

* 2,3-Butanediol
* 1,3-Propanediol
* Ethylene glycol

References

External links

* [http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@na+1,4-Butanediol NLM Hazardous Substances Databank – 1,4-Butanediol]