 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Butane-1,4-diol | |
| Other names Tetramethylene glycol | |
| Identifiers | |
| |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.003.443 |
| EC Number |
|
| RTECS number |
|
| UNII | |
| |
| |
| 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) | 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 | |
Relatedbutanediols | 1,2-Butanediol 1,3-Butanediol 2,3-Butanediol cis-Butene-1,4-diol |
Related compounds | Succinaldehyde Succinic acid |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
1,4-Butanediol, also calledbutane-1,4-diol (other names include1,4-B,BD,BDO, and1,4-BD),[5] is aprimary alcohol and anorganic compound with theformula HOCH2CH2CH2CH2OH. It is a colorlessviscousliquid 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]
In one industrialchemical synthesis,acetylene reacts with two equivalents offormaldehyde to formbutyne-1,4-diol.Hydrogenation of butyne-1,4-diol gives butane-1,4-diol.[9] It is also made on an industrial scale frommaleic anhydride in the Davy process, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are frombutadiene,allyl acetate andsuccinic acid.
A biological route to BD has been commercialized that uses agenetically modified organism.[10] Thebiosynthesis proceeds via4-hydroxybutyrate.
Butane-1,4-diol is used industrially as asolvent[additional citation(s) needed] and in the manufacture of some types ofplastics, elasticfibers andpolyurethanes. Inorganic chemistry, 1,4-butanediol is used for the synthesis ofγ-butyrolactone (GBL). In the presence ofphosphoric acid and high temperature, it dehydrates to the important solventtetrahydrofuran.[11] At about 200 °C in the presence of solublerutheniumcatalysts, the diol undergoesdehydrogenation to formbutyrolactone.[12] It is used to synthesize1,4-butanediol diglycidyl ether which is then used as areactive diluent forepoxy resins.[13]
1,4-Butanediol is used in the production ofpolybutylene terephthalate (PBT) plastic.[14]
World production of butane-1,4-diol was claimed to be about one million metric tons per year and market price is aboutUS$2,000 (€1,600) per ton in 2005. In 2013, worldwide production was claimed to be billions of pounds (consistent with approximately one million metric tons).[15]
Almost half of it is dehydrated totetrahydrofuran to make fibers such asSpandex.[16] The largest producer isBASF.[17]
Butane-1,4-diol is also used as arecreational drug known by some users as "Bute",[18] "One Comma Four", "Liquid Fantasy", "One Four Bee" or "One Four B-D-O".
Somefederal courts in the USA have stated that 1,4-butanediol exerts effects similar to its metabolite,GABA analoguegamma-hydroxybutyrate (GHB), but several other federal courts have ruled that it does not.
1,4-butenediol (CAS 110-64-5) may be incorrectly sold as 1,4-butanediol but should not be confused with it.
Butane-1,4-diol is rapidly converted into GHB acid by the enzymesalcohol dehydrogenase andaldehyde dehydrogenase, and differing levels of these enzymes may account for differences in effects andside effects between users.[19] While co-administration ofethanol and GHB already poses serious risks, co-administration of ethanol with 1,4-butanediol will interact considerably and has many other potential risks. This is because the same enzymes that are responsible for metabolizing alcohol also metabolize 1,4-butanediol so there is a strong chance of a dangerousdrug interaction.[19][20] Emergency room patients who overdose on both ethanol and 1,4-butanediol often present with symptoms ofalcohol 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.[19]
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.[20] 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 thealcohol dehydrogenase andaldehyde 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 metaboliteacetaldehyde.
Another study found no effect following intracerebroventricular injection of butane-1,4-diol in rats.[21] 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.
While butane-1,4-diol is not currentlyscheduled federally in the United States,[22] a number of states have classified 1,4-butanediol as a controlled substance. Individuals have been prosecuted for possession of 1,4-butanediol under theFederal Analog Act as substantially similar to GHB.[23] A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered ananalog of GHB under federal law,[24] but that decision was later overturned by the Second Circuit.[25] A jury in Federal District Court in Chicago found that 1,4-butanediol was not an analog of GHB under federal law, which was not disputed on the case's appeal to the Seventh Circuit Court of Appeals, however this finding did not affect the outcome of the case.[26] In theUnited Kingdom, 1,4-butanediol was scheduled in December 2009 (along with another GHB precursor,gamma-butyrolactone) as aClass C controlled substance. In Germany, the drug is not explicitly illegal, but might also be treated as illegal if used as a drug. It is controlled as a Schedule VIprecursor inCanada.
A toy called "Bindeez" ("Aqua Dots" in North America) was recalled by the distributor in November 2007 because of the presence of butane-1,4-diol. The toy consists of small beads that stick to each other by sprinkling water. Butane-1,4-diol was detected byGC-MS.[27] The production plant seems to have intended to cut costs by replacing less toxicpentane-1,5-diol with butane-1,4-diol. ChemNet China listed the price of butane-1,4-diol 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.[28]
In August 2021, several people fell severely ill after consuming drinks at building L2.01 at the Lichtwiese Campus ofDarmstadt Technical University, Germany. Seven showed severe symptoms, two were transported to a hospital inFrankfurt am Main, and a 30-year-old person was, for a time, in a critical state. Butane-1,4-diol had been detected in milk packages, as well as in water filters. At the location, detectives also foundbromophenols anddicyclohexylamine.[29]
A variety of 1,4-butanediolderivatives are GHB-like drugs orGHB receptoragonists. These includeGHB itself,γ-butyrolactone (GBL),aceburic acid,ethyl acetoxy butanoate (EAB),Γ-crotonolactone,γ-hydroxybutyraldehyde,γ-hydroxyvaleric acid (GHV),γ-valerolactone,γ-hydroxycrotonic acid (GHC or T-HCA), and4-hydroxy-4-methylpentanoic acid (UMB68), among others. Ananalogue that is not a 1,4-butanediol derivative but is related and still showsaffinity for the GHB receptor is3-chloropropanoic acid (UMB66).
{{cite book}}: CS1 maint: overridden setting (link){{cite web}}: CS1 maint: overridden setting (link){{cite web}}: CS1 maint: overridden setting (link){{cite web}}: CS1 maint: overridden setting (link){{cite web}}: CS1 maint: overridden setting (link){{cite web}}: CS1 maint: overridden setting (link)