1,4-Butanediol

One of four stable isomers of butanediol 1,4-butenediol November 2022 cs2 changed 477205926 1,4-Butanediol 1,4-butanediol.svg skin-invert-image 1,4-Butanediol-3D-balls.png bg-transparent 1,4-Butanediol Butane-1,4-diol Tetramethylene glycol 1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2 correct chemspider 1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2 correct chemspider WERYXYBDKMZEQL-UHFFFAOYSA-N C(CCO)CO 110-63-4 correct CAS 203-786-5 correct chemspider correct drugbank DB01955 13835209 correct EBI 171623 41189 correct EBI EK0525000 correct FDA 7XOO2LE6G3 8064 OCCCCO C-190 cs211 04 1,4-Butanediol March 1999 4 10 2 1.0171 g/cm3 (20 °C) 20.1 235 Miscible Soluble ethanol 1.4460 (20 °C) −61.5·10−6 cm3/mol HSNO Chemical Classification Information Database https://www.epa.govt.nz/database-search/chemical-classification-and-information-database-ccid/view/1FE05653-F46B-45F6-AE62-B5D125DD68A0 New Zealand Environmental Protection Authority https://pubchem.ncbi.nlm.nih.gov/compound/8064#datasheet=LCSS&section=GHS-Classification 1,4-Butanediol Laboratory Chemical Safety Summary cs2 exclamation mark Acute Tox. (oral) 4 WARNING 302 336 261 264 270 271 301+312 304+340 312 330 403+233 405 501 1 1 0 121 (open cup) 350 1,2-Butanediol1,3-Butanediol2,3-Butanediolcis-Butene-1,4-diol butanediols SuccinaldehydeSuccinic acid 1,4-Butanediol, also called butane-1,4-diol (other names include 1,4-B, BD, dose, BDO, and 1,4-BD),https://www.webmd.com/vitamins/ai/ingredientmono-21/1-4-butanediol 1,4-Butanediol - Uses, Side Effects, and More WebMD 31 March 2024 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".Dekkers M. P. J. January 1890 Le glycol tétraméthylénique https://books.google.com/books?id=0RjzAAAAMAAJ&pg=PA92 Recueil des Travaux Chimiques des Pays-Bas en 9 4 92–102 10.1002/recl.18900090403 0165-0513 subscription Dekkers Pieter Johannes https://books.google.com/books?id=X_8TAQAAIAAJ Over het Tetramethyleenglycol: Proefschr. ... te verdedigen ... door Pieter Johannes Dekkers 1890 L. van Nifterik Hz. nl Synthesis class=skin-invert-image|thumb|left|380px|Conversion of butane to butanediol or butyrolactone via oxidation to maleic anhydride followed by hydrogenation over copper chromite10.1002/14356007.a13_487 Hydrogenation and Dehydrogenation Ullmann's Encyclopedia of Industrial Chemistry 2000 Rylander Paul N. 3-527-30673-0 In one industrial chemical synthesis, acetylene reacts with two equivalents of formaldehyde to form butyne-1,4-diol. Hydrogenation of butyne-1,4-diol gives butane-1,4-diol.2023-07-30 1,4-Butanediol Production And Uses https://chemcess.com/14-butanediol-production-and-uses/ 2023-07-30 en-US It is also made on an industrial scale from maleic anhydride in the Davy process, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are from butadiene, allyl acetate and succinic acid. A biological route to BD has been commercialized that uses a genetically modified organism.http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=/netahtml/PTO/srchnum.htm&r=1&f=G&l=50&s1=8067214.PN.&OS=PN/8067214&RS=PN/8067214 United States Patent: 8067214 - Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors uspto.gov 1 April 2018 cs2 23 May 2020 https://web.archive.org/web/20200523060621/http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=/netahtml/PTO/srchnum.htm&r=1&f=G&l=50&s1=8067214.PN.&OS=PN/8067214&RS=PN/8067214 dead The biosynthesis proceeds via 4-hydroxybutyrate. Industrial use Butane-1,4-diol is used industrially as a solventOctober 2024 and in the manufacture of some types of plastics, elastic fibers and polyurethanes. 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. Karas L. Piel W. J. Ethers At about 200 °C in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone. Zhao Jing Hartwig John F. John F. Hartwig 2005 Acceptorless, neat, ruthenium-catalyzed dehydrogenative cyclization of diols to lactones Organometallics 24 2441–46 10.1021/om048983m 10 It is used to synthesize 1,4-butanediol diglycidyl ether which is then used as a reactive diluent for epoxy resins.Monte Salvatore J. Diluents and viscosity modifiers for epoxy resins 1998 https://doi.org/10.1007/978-94-011-5862-6_24 Plastics Additives: An A-Z reference Polymer Science and Technology Series 1 211–216 Pritchard Geoffrey Dordrecht Springer Netherlands en 10.1007/978-94-011-5862-6_24 978-94-011-5862-6 2022-03-29 subscription 1,4-Butanediol is used in the production of polybutylene terephthalate (PBT) plastic.Polybutylene Terephthalate (PBT) Material Guide & Properties Info https://omnexus.specialchem.com/selection-guide/polybutylene-terephthalate-pbt-plastic 2023-11-24 omnexus.specialchem.com en https://web.archive.org/web/20231124155646/https://omnexus.specialchem.com/selection-guide/polybutylene-terephthalate-pbt-plastic 2023-11-24 World production of butane-1,4-diol was claimed to be about one million metric tons per year and market price is about yes2,000 (€1,600) per ton in 2005. In 2013, worldwide production was claimed to be billions of pounds (consistent with approximately one million metric tons).Commercial-scale production of bio-based BDO announced http://www.chemengonline.com/commercial-scale-production-of-bio-based-bdo-announced/ Feb 2013 Chemical Engineering 2013-02-21 https://web.archive.org/web/20150204185115/http://www.chemengonline.com/commercial-scale-production-of-bio-based-bdo-announced/ 2015-02-04 live Almost half of it is dehydrated to tetrahydrofuran to make fibers such as Spandex. http://www.accessmylibrary.com/coms2/summary_0286-15012128_ITM Butanediol (price and demand in market) 12 April 2006 Chemical Week 2008-11-21 The largest producer is BASF. Malaysia: New 1,4-butanediol plant used below capacity http://findarticles.com/p/articles/mi_qa5358/is_200404/ai_n21348316 https://web.archive.org/web/20090418012430/http://findarticles.com/p/articles/mi_qa5358/is_200404/ai_n21348316/ usurped 18 April 2009 April 2004 Asian Textile Business 2008-11-21 Use as a recreational drug thumb|right|class=skin-invert-image|FDA warning against products containing GHB and its prodrugs, such as butane-1,4-diol|352x352px Butane-1,4-diol is also used as a recreational drug known by some users as "Bute",Australian Associated Press Date-rape drug 'bute' increasingly linked to sexual assaults in Australia, police say the Guardian 2024-05-30 https://www.theguardian.com/society/article/2024/may/30/australia-date-rape-drug-bute-butanediol-sexual-assaults-police-seizure 2024-05-30 "One Comma Four", "Liquid Fantasy", "One Four Bee" or "One Four B-D-O". Some federal courts in the United States have stated that 1,4-butanediol exerts effects similar to its metabolite, GABA analogue gamma-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. Pharmacokinetics Butane-1,4-diol is rapidly converted into GHB acid 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. Benzer Theodore I. Cameron Scott Russi Christopher Scott 8 January 2007 Toxicity, Gamma-Hydroxybutyrate http://www.emedicine.com/emerg/topic848.htm eMedicine 2009-08-29 While co-administration of ethanol 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 dangerous drug interaction. Poldrugo Flavio Snead III O. Carter 1984 1,4-butanediol, γ-hydroxybutyric acid and ethanol: Relationships and interactions Neuropharmacology 23 1 109–13 10.1016/0028-3908(84)90226-0 6717752 54415695 Emergency room patients who overdose on both ethanol and 1,4-butanediol often present with symptoms of alcohol 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. class=skin-invert-image|thumb|center|600px|Metabolic pathway of butane-1,4-diol, γ-butyrolactone and γ-hydroxybutyric acid (GHB) 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. 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. 17100847 2006 Carter LP Koek W France CP Lack of effects of GHB precursors GBL and 1,4-BD following i.c.v. Administration in rats 24 9 2595–600 10.1111/j.1460-9568.2006.05146.x The European Journal of Neuroscience 24609982 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 scheduled federally in the United States,https://www.law.cornell.edu/uscode/text/21/841 21 U.S. Code § 841 - Prohibited acts A LII / Legal Information Institute 2016-08-02 cs2 a number of states have classified 1,4-butanediol as a controlled substance. Individuals have been prosecuted for possession of 1,4-butanediol under the Federal Analog Act as substantially similar to GHB.USA v Washam (2002) 312 F.3d 926, 930; http://cases.justia.com/us-court-of-appeals/F3/312/926/608696/ A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered an analog of GHB under federal law,http://www.erowid.org/chemicals/14b/14b_law1.shtml Erowid 1,4-Butanediol Vault : Law : New York Federal Court Rules Analogue Act Unconstitutionally Vague with regard to 1,4-Butanediol www.erowid.org 1 April 2018 cs2 but that decision was later overturned by the Second Circuit.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 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.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. In the United Kingdom, 1,4-butanediol was scheduled in December 2009 (along with another GHB precursor, gamma-butyrolactone) as a Class 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 VI precursor in Canada. 2007 contamination of Bindeez toy Bindeez 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 by GC-MS. Wang Linda 9 November 2007 Industrial Chemical Sullies Popular Children's Toy http://pubs.acs.org/cen/news/85/i46/8546news11.html Chemical & Engineering News 2009-08-11 The production plant seems to have intended to cut costs by replacing less toxic pentane-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. US mother says her son began to stumble and vomit after eating Chinese-made toy, now recalled http://news.bostonherald.com/news/national/general/view.bg?articleid=1043462&srvc=next_article Associated Press 8 November 2007 Boston Herald 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 Darmstadt Technical University, Germany. Seven showed severe symptoms, two were transported to a hospital in Frankfurt 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 found bromophenols and dicyclohexylamine.https://www.stern.de/panorama/stern-crime/vergiftungen-an-tu-darmstadt--ermittler-finden-k--o--tropfen-in-kueche-30687682.html Ermittler finden nach Vergiftungen an TU Darmstadt offenbar K.-o.-Tropfen in Küche 2021-08-27 2021-09-01 Stern cs2 Derivatives A variety of 1,4-butanediol derivatives are GHB-like drugs or GHB receptor agonists. These include GHB itself, γ-butyrolactone (GBL), aceburic acid, ethyl acetoxy butanoate (EAB), Γ-crotonolactone, γ-hydroxybutyraldehyde, γ-hydroxyvaleric acid (GHV), γ-valerolactone (GVL), γ-hydroxycrotonic acid (GHC or T-HCA), and 4-hydroxy-4-methylpentanoic acid (UMB68), among others. An analogue that is not a 1,4-butanediol derivative but is related and still shows affinity for the GHB receptor is 3-chloropropanoic acid (UMB66). See also 1,3-Butanediol 1,4-Butanediol diglycidyl ether 2-Methyl-2-propyl-1,3-propanediol 4-Amino-1-butanol References 30em External links 1104 11 1,4-Butanediol 110634 November 2002 Record in the Household Products Database of NLM Category:Alcohol solvents Category:Designer prodrugs Category:Sedatives Category:Alkanediols Category:Neurotransmitter precursors Category:GABAB receptor agonists Category:GHB receptor agonists Category:GABA analogues Category:Primary alcohols Category:1,4-Butanediyl compounds