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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 acetylene-based process is illustrative of what is known as "Reppe chemistry", after German chemist Walter Reppe. Hydrogenation of 1,4-butynediol gives 1,4-butanediol.
LyondellBasell manufactures 1,4-butanediol in a proprietary, multi-step process without the use of acetylene. First, propylene oxide is converted to allyl alcohol. The allyl alcohol is then hydroformylated to 4-hydroxybutyraldehyde. Hydrogenation of the 4-hydroxybutyraldehyde yields 1,4-butanediol.
It is also manufactured on an industrial scale from maleic anhydride, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are from butadiene, allyl acetate and succinic acid.
Genomatica (a San Diego-based company) has genetically engineered E. coli to metabolize sugar into 1,4-butanediol. They expect to build and begin operating a pilot plant by the end of 2009. Genomatica CEO Christopher Gann said the process consumes 32,000 BTU per pound of 1,4-butanediol (75 MJ/kg), far less than the acetylene-based process, and does not have any by-products.
World production of 1,4-butanediol is about one million metric tons per year and market price is about 2,000 USD (1,600 EUR) per ton (2005). Almost half of it is dehydrated to tetrahydrofuran to make fibers such as Spandex. The largest producer is BASF.
Health effects and use as a drug
FDA warning against products containing GHB and its prodrugs, such as 1,4-Butanediol.
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.
Anecdotal reports indicate that 1,4-butanediol produces a strong toxic feeling not present with GHB when ingested. These reports also indicate that it may cause damage to the liver as well as to other vital organs. Abuse has also resulted in addiction and death.
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. Because these enzymes are also responsible for metabolizing alcohol there is a strong chance of a dangerous drug interaction. 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.
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.
Like GHB, 1,4 is only safe in small amounts, usually between 1cc to 1.5 cc. 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 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. Additionally, individuals have been prosecuted for 1,4-butanediol under the Federal Analog Act as substantially similar to GHB. A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered an analogue of GHB under federal law. Scheduling of 1,4-butanediol on a federal level may be unlikely considering its legitimate industrial applications.
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 was detected by GC-MS. The production plant seems to have intended to cut costs by replacing less toxic 1,5-pentanediol with 1,4-butanediol. ChemNet China listed 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.
References
Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C-190. ISBN0-8493-0462-8..
^ 1,4-Butanediol, International Chemical Safety Card 1104, Geneva: International Programme on Chemical Safety, March 1999.
Zhao, Jing; Hartwig, John F. (2005), "Acceptorless, neat, ruthenium-catalyzed dehydrogenative cyclization of diols to lactones", Organometallics, 24 (10): 2441–46, doi:10.1021/om048983m
Satta, Rosalba; Dimitrijevic, Nikola; Manev, Hari (2003), "Drosophila metabolize 1,4-butanediol into γ-hydroxybutyric acid in vivo", Eur. J. Pharmacol., 473 (2–3): 149–52, doi:10.1016/S0014-2999(03)01993-9, PMID12892832.
Carai, Maurio A. M.; Colombo, Giancarlo; Reali, Roberta; Serra, Salvatore; Mocci, Ignazia; Castelli, M. Paola; Cignarella, Giorgio; Gessa, Gian Luigi (2002), "Central effects of 1,4-butanediol are mediated by GABAB receptors via its conversion into γ-hydroxybutyric acid", Eur. J. Pharmacol., 441 (3): 157–63, doi:10.1016/S0014-2999(02)01502-9, PMID12063087.
Zvosec, Deborah L.; Smith, Stephan W.; McCutcheon, J. Rod; Spillane, Joe; Hall, Bradley J.; Peacock, Elizabeth A. (2001), "Adverse events, including death, associated with the use of 1,4-butanediol", New Engl. J. Med., 344 (2): 87–94, doi:10.1056/NEJM200101113440202, PMID11150358.
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