1,4-Butanediol
Names | |
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Preferred IUPAC name
Butane-1,4-diol | |
Other names
Tetramethylene glycol
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.003.443 |
EC Number |
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PubChem CID
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RTECS number
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UNII | |
CompTox Dashboard (EPA)
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Properties[1][2] | |
C4H10O2 | |
Molar mass | 90.122 g·mol−1 |
Density | 1.0171 g/cm3 (20 °C) |
Melting point | 20.1 °C (68.2 °F; 293.2 K) |
Boiling point | 235 °C (455 °F; 508 K) |
Miscible | |
Solubility in ethanol | Soluble |
-61.5·10−6 cm3/mol | |
Refractive index (nD)
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1.4460 (20 °C) |
Hazards[3][4] | |
GHS labelling: | |
Warning | |
H302, H336 | |
P261, P264, P270, P271, P301+P312, P304+P340, P312, P330, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | (open cup) 121 °C (250 °F; 394 K) |
350 °C (662 °F; 623 K) | |
Related compounds | |
Related butanediols
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1,2-Butanediol 1,3-Butanediol 2,3-Butanediol cis-Butene-1,4-diol |
Related compounds
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Succinaldehyde Succinic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,4-Butanediol, also called Butane-1,4-diol (other names include 1,4-B, BD, BDO and 1,4-BD),[5] is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colorless viscous liquid first synthesized in 1890 via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol".[6][7]
Synthesis
In industrial
A biological route to BD has been commercialized that uses a
Industrial use
Butane-1,4-diol is used industrially as a
1,4-Butanediol is used in the production of polybutylene terephthalate (PBT) plastic.[13]
World production of butane-1,4-diol was claimed to be about one million metric tons per year and market price is about US$ 2,000 (€1,600) per ton (2005). In 2013, worldwide production was claimed to be billions of pounds (consistent with approximately one million metric tons).[14]
Almost half of it is dehydrated to tetrahydrofuran to make fibers such as Spandex.[15] The largest producer is BASF.[16]
Use as a recreational drug
Butane-1,4-diol is also used as a
Some federal courts in the USA have stated that 1,4-butanediol exerts effects similar to its metabolite gamma-hydroxybutyrate (GHB), but several other federal courts have ruled that it does not.
Pharmacokinetics
Butane-1,4-diol is rapidly converted into gamma-hydroxybutyric acid by the enzymes
Pharmacodynamics
Butane-1,4-diol 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 a study suggesting that 1,4-butanediol may have potential alcohol-like pharmacological effects on its own.[18] The study arrived at this conclusion based on the finding that butane-1,4-diol coadministered with ethanol led to potentiation of some of the behavioral effects of ethanol. However, potentiation of ethanol's effects may simply be caused by competition for the alcohol dehydrogenase and aldehyde dehydrogenase enzymes with co-administered 1,4-butanediol. The shared metabolic rate-limiting steps thus leads to slowed metabolism and clearance for both compounds including ethanol's known toxic metabolite acetaldehyde.
Another study found no effect following intracerebroventricular injection of butane-1,4-diol in rats.[19] This contradicts the hypothesis of butane-1,4-diol having inherent alcohol-like pharmacological effects.
Like gamma-hydroxybutyric acid, butane-1,4-diol is safe only in small amounts. Adverse effects in higher doses include nausea, vomiting, dizziness, sedation, vertigo, and potentially death if ingested in large amounts. Anxiolytic effects are diminished and side effects increased when used in combination with alcohol.
Legality
While butane-1,4-diol is not currently
2007 contamination of Bindeez toy
A toy called "
2021 poisoning at Darmstadt Technical University
In August 2021, several people fell severely ill after consuming drinks at building L2.01 at the Lichtwiese Campus of
See also
References
- ISBN 0-8493-0462-8
- ^ 1,4-Butanediol, International Chemical Safety Card 1104, Geneva: International Programme on Chemical Safety, March 1999
- ^ HSNO Chemical Classification Information Database, New Zealand Environmental Protection Authority
- ^ "1,4-Butanediol Laboratory Chemical Safety Summary"
- ^ "1,4-Butanediol - Uses, Side Effects, and More". WebMD. Retrieved 31 March 2024.
- ISSN 0165-0513.
- ^ Dekkers, Pieter Johannes (1890). Over het Tetramethyleenglycol: Proefschr. ... te verdedigen ... door Pieter Johannes Dekkers (in Dutch). L. van Nifterik Hz.
- ^ "1,4-Butanediol Production And Uses". 30 July 2023. Retrieved 30 July 2023.
- ^ "United States Patent: 8067214 - Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors", uspto.gov, retrieved 1 April 2018
- ISBN 9780471238966
- ISBN 978-94-011-5862-6, retrieved 29 March 2022
- ^ "Polybutylene Terephthalate (PBT) Material Guide & Properties Info". omnexus.specialchem.com. Archived from the original on 24 November 2023. Retrieved 24 November 2023.
- ^ "Commercial-scale production of bio-based BDO announced", Chemical Engineering, February 2013, archived from the original on 4 February 2015, retrieved 21 February 2013
- Chemical Week, 12 April 2006, retrieved 21 November 2008
- ^ "Malaysia: New 1,4-butanediol plant used below capacity", Asian Textile Business, April 2004, retrieved 21 November 2008
- ^ a b c Benzer, Theodore I.; Cameron, Scott; Russi, Christopher Scott (8 January 2007), Toxicity, Gamma-Hydroxybutyrate, eMedicine, retrieved 29 August 2009
- ^ S2CID 54415695
- S2CID 24609982
- ^ "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2 August 2016
- ^ USA v Washam (2002) 312 F.3d 926, 930; http://cases.justia.com/us-court-of-appeals/F3/312/926/608696/
- ^ "Erowid 1,4-Butanediol Vault : Law : New York Federal Court Rules Analogue Act Unconstitutionally Vague with regard to 1,4-Butanediol", www.erowid.org, retrieved 1 April 2018
- ^ United States v. Roberts, 363 F.3d 118 (2d Cir. 2004); https://scholar.google.com/scholar_case?case=13457043198797192346&q=363+F.3d+118&hl=en&as_sdt=6,39
- ^ United States v. Turcotte, 405 F.3d 515 (7th Cir. 2005) "With specific regard to 1,4 Butanediol, the jury has returned a special verdict which states that 1,4-Butanediol is not a Schedule I Narcotic Drug Controlled Substance analogue, because 1,4-Butanediol's chemical structure is not significantly similar to the chemical structure of GHB.
- ^ Wang, Linda (9 November 2007), "Industrial Chemical Sullies Popular Children's Toy", Chemical & Engineering News, retrieved 11 August 2009
- ^ "US mother says her son began to stumble and vomit after eating Chinese-made toy, now recalled", Boston Herald, Associated Press, 8 November 2007
- ^ "Ermittler finden nach Vergiftungen an TU Darmstadt offenbar K.-o.-Tropfen in Küche", Stern, 27 August 2021, retrieved 1 September 2021
External links
- International Chemical Safety Card 1104
- SIDS Initial Assessment Report for 1,4-Butanediol from the Organisation for Economic Co-operation and Development(OECD)
- Record in the Household Products Database of NLM