1,4-Butanediol, colloquially known as BD or BDO, is a
primary alcohol
A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group.
In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary a ...
, and an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
, with the
formula HOCH
2CH
2CH
2CH
2OH. It is a colorless
viscous
The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water.
Viscosity quantifies the inte ...
liquid. It is one of four stable
isomers of
butanediol Butanediol, also called butylene glycol, may refer to any one of four stable structural isomers:
* 1,2-Butanediol
* 1,3-Butanediol
*1,4-Butanediol
*2,3-Butanediol
2,3-Butanediol is the organic compound with the formula (CH3CHOH)2. It is classif ...
.
Synthesis
In industrial
synthesis,
acetylene reacts with two equivalents of
formaldehyde
Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section ...
to form
1,4-butynediol.
Hydrogenation
Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to reduce or saturate organ ...
of 1,4-butynediol gives 1,4-butanediol. It is also manufactured on an industrial scale from
maleic anhydride
Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and pol ...
in the Davy process, which is first converted to the methyl maleate ester, then hydrogenated. Other routes are from
butadiene
1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two vi ...
,
allyl acetate
Allyl acetate is an organic compound with formula C3H5OC(O)CH3. This colourless liquid is a precursor to especially allyl alcohol, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.
Preparation
Allyl acetate i ...
and
succinic acid
Succinic acid () is a dicarboxylic acid with the chemical formula (CH2)2(CO2H)2. The name derives from Latin ''succinum'', meaning amber. In living organisms, succinic acid takes the form of an anion, succinate, which has multiple biological ro ...
.
A biological route to BD has been commercialized that uses a
genetically modified organism. The
biosynthesis proceeds via
4-hydroxybutyrate.
Industrial use
1,4-Butanediol is used industrially as a
solvent
A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...
and in the manufacture of some types of
plastic
Plastics are a wide range of synthetic or semi-synthetic materials that use polymers as a main ingredient. Their plasticity makes it possible for plastics to be moulded, extruded or pressed into solid objects of various shapes. This adaptab ...
s, elastic
fiber
Fiber or fibre (from la, fibra, links=no) is a natural or artificial substance that is significantly longer than it is wide. Fibers are often used in the manufacture of other materials. The strongest engineering materials often incorpora ...
s and
polyurethane
Polyurethane (; often abbreviated PUR and PU) refers to a class of polymers composed of organic units joined by carbamate (urethane) links. In contrast to other common polymers such as polyethylene and polystyrene, polyurethane is produced from ...
s. In
organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...
, 1,4-butanediol is used for the synthesis of
γ-butyrolactone (GBL). In the presence of
phosphoric acid
Phosphoric acid (orthophosphoric acid, monophosphoric acid or phosphoric(V) acid) is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula . It is commonly encountered as an 85% aqueous solution, w ...
and high temperature, it dehydrates to the important solvent
tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
.
At about 200 °C in the presence of soluble
ruthenium
Ruthenium is a chemical element with the symbol Ru and atomic number 44. It is a rare transition metal belonging to the platinum group of the periodic table. Like the other metals of the platinum group, ruthenium is inert to most other chemical ...
catalyst
Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...
s, the diol undergoes
dehydrogenation
In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...
to form
butyrolactone. It is used to synthesize
1,4-Butanediol diglycidyl ether which is then used as a
reactive diluent for
epoxy resins.
World production of 1,4-butanediol was claimed to be about one million metric tons per year and market price is about 2,000 (€1,600) per ton (2005). In 2013, worldwide production was claimed to be billions of lbs (consistent with approximately one million metric tons).
Almost half of it is dehydrated to
tetrahydrofuran
Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water- miscible organic liquid with low viscosity. It is ...
to make fibers such as
Spandex
Spandex, Lycra, or elastane is a synthetic fiber known for its exceptional elasticity. It is a polyether-polyurea copolymer that was invented in 1958 by chemist Joseph Shivers at DuPont's Benger Laboratory in Waynesboro, Virginia, US.
The g ...
. The largest producer is
BASF
BASF SE () is a German multinational chemical company and the largest chemical producer in the world. Its headquarters is located in Ludwigshafen, Germany.
The BASF Group comprises subsidiaries and joint ventures in more than 80 countries ...
.
Use as a recreational drug
![Dangerous dietary supplements](https://upload.wikimedia.org/wikipedia/commons/3/34/Dangerous_dietary_supplements.gif)
1,4-Butanediol is also used as a
recreational drug known by some users as "One Comma Four", "Liquid Fantasy", "One Four Bee" or "One Four B-D-O". A few Federal Courts have stated that 1,4-butanediol exerts effects similar to
γ-hydroxybutyrate
''gamma''-Hydroxybutyric acid (or γ-hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid) is a naturally occurring neurotransmitter and a depressant drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas. ...
(GHB), which is a metabolic product of 1,4-butanediol. But other Federal Courts have ruled that it is not.
Pharmacokinetics
1,4-Butanediol is rapidly converted into
GHB
''gamma''-Hydroxybutyric acid (or γ-hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid) is a naturally occurring neurotransmitter and a depressant drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas. ...
by the enzymes
alcohol dehydrogenase
Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to NA ...
and
aldehyde dehydrogenase
Aldehyde dehydrogenases () are a group of enzymes that catalyse the oxidation of aldehydes. They convert aldehydes (R–C(=O)) to carboxylic acids (R–C(=O)). The oxygen comes from a water molecule. To date, nineteen ALDH genes have b ...
, and differing levels of these enzymes may account for differences in effects and
side effects
In medicine, a side effect is an effect, whether therapeutic or adverse, that is secondary to the one intended; although the term is predominantly employed to describe adverse effects, it can also apply to beneficial, but unintended, consequence ...
between users.
While co-administration of
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
and GHB already poses serious risks, co-administration of
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
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
Drug interactions occur when a drug's mechanism of action is disturbed by the concomitant administration of substances such as foods, beverages, or other drugs. The cause is often the inhibition of the specific receptors available to the drug, ...
.
Emergency room patients who overdose on both
ethanol
Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...
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.
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 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 1,4-butanediol co-administered 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
Alcohol dehydrogenases (ADH) () are a group of dehydrogenase enzymes that occur in many organisms and facilitate the interconversion between alcohols and aldehydes or ketones with the reduction of nicotinamide adenine dinucleotide (NAD+) to NA ...
and
aldehyde dehydrogenase
Aldehyde dehydrogenases () are a group of enzymes that catalyse the oxidation of aldehydes. They convert aldehydes (R–C(=O)) to carboxylic acids (R–C(=O)). The oxygen comes from a water molecule. To date, nineteen ALDH genes have b ...
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 in rats of 1,4-butanediol. This contradicts the hypothesis of 1,4-butanediol having inherent alcohol-like pharmacological effects.
Like
GHB
''gamma''-Hydroxybutyric acid (or γ-hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid) is a naturally occurring neurotransmitter and a depressant drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas. ...
, 1,4-butanediol is only safe 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 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. Individuals have been prosecuted for possession of 1,4-butanediol under the
Federal Analog Act
The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...
as substantially similar to
GHB
''gamma''-Hydroxybutyric acid (or γ-hydroxybutyric acid (GHB), also known as 4-hydroxybutanoic acid) is a naturally occurring neurotransmitter and a depressant drug. It is a precursor to GABA, glutamate, and glycine in certain brain areas. ...
. A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered an
analog
Analog or analogue may refer to:
Computing and electronics
* Analog signal, in which information is encoded in a continuous variable
** Analog device, an apparatus that operates on analog signals
*** Analog electronics, circuits which use analog ...
of GHB under federal law, but that decision was later overturned by the Second Circuit. 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. In the
United Kingdom
The United Kingdom of Great Britain and Northern Ireland, commonly known as the United Kingdom (UK) or Britain, is a country in Europe, off the north-western coast of the European mainland, continental mainland. It comprises England, Scotlan ...
, 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
Precursor or Precursors may refer to:
* Precursor (religion), a forerunner, predecessor
** The Precursor, John the Baptist
Science and technology
* Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of u ...
in
Canada
Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tot ...
.
2007 contamination of Bindeez toy
A toy called "
Bindeez
Bindeez (also marketed as Aqua Dots, Beados,Moose Beados Site PixOs,Pixos Site http://www.pixos.com/ and Aquabeads) are a children's toy, consisting of small coloured plastic beads that can be arranged in designs.
In 2007, Bindeez was subjec ...
" ("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
1,5-Pentanediol is the organic compound with the formula HOCHCHCHCHCHOH. Like other diols, this viscous colourless liquid is used as plasticizer and also forms polyesters that are used as emulsifying agents and resin intermediates.
1,5-Pentan ...
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.
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
Darmstadt () is a city in the state of Hesse in Germany, located in the southern part of the Rhine-Main-Area (Frankfurt Metropolitan Region). Darmstadt has around 160,000 inhabitants, making it the fourth largest city in the state of Hesse ...
, Germany. Seven showed severe symptoms, two were transported to a hospital in
Frankfurt
Frankfurt, officially Frankfurt am Main (; Hessian: , " Frank ford on the Main"), is the most populous city in the German state of Hesse. Its 791,000 inhabitants as of 2022 make it the fifth-most populous city in Germany. Located on it ...
, and a 30-year-old person was, for a time, in a critical state. 1,4-butanediol had been detected in milk packages, as well as in water filters. At the location, detectives also found
bromophenols and
dicyclohexylamine.
See also
*
1,4-Butanediol diglycidyl ether
References
External links
*
*
Recordin the Household Products Database of
NLM
{{DEFAULTSORT:Butanediol, 1, 4-
Alcohol solvents
Prodrugs
Sedatives
Alkanediols
GABAB receptor agonists
GHB receptor agonists
Designer drugs
GABA analogues
Primary alcohols
1,4-Butanediyl compounds