Mason Delacroix
Butane-1,4-diol, also known as 1,4-Butanediol, is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colourless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain. Butane-1,4-diol is used in the synthesis of epothilones, a new class of cancer drugs, and in the stereoselective synthesis of (-)-Brevisamide. It is also used industrially as a solvent and in the manufacture of plastics, elastic fibres, and polyurethanes.
| Characteristics | Values |
|---|---|
| Chemical Formula | HOCH2CH2CH2CH2OH |
| Appearance | Colorless, viscous liquid or solid (depending upon temperature) |
| Odor | Odorless |
| Boiling Point | 230°C |
| Melting Point | 16°C |
| Uses | - Industrial cleaner and glue remover |
- Solvent
- Synthesis of γ-butyrolactone (GBL)
- Production of other organic chemicals
- Reactive diluent for epoxy resins
- Cross-linking agent for thermoplastic urethanes, polyester plasticizers, paints and coatings
- Component in the production of recreational drugs
- Precursor for several industrial chemicals | | Side Effects | Nausea, vomiting, dizziness, sedation, vertigo, and potentially death if ingested in large amounts |
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What You'll Learn
Butane-1,4-diol is a primary alcohol
Butane-1,4-diol, also called 1,4-B, BD, BDO, and 1,4-BD, is a primary alcohol. It is a colourless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain. It has the chemical formula HOCH2CH2CH2CH2OH.
Butane-1,4-diol was first synthesized in 1890 by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol". Dekkers created the compound via acidic hydrolysis of N,N'-dinitro-1,4-butanediamine. Butane-1,4-diol can also be produced industrially through various other chemical processes. For example, acetylene can react with two equivalents of formaldehyde to form butyne-1,4-diol, which can then be hydrogenated to give butane-1,4-diol.
Butane-1,4-diol is used as a precursor for several industrial chemicals, as well as a component in the production of recreational drugs. It is used industrially as a solvent and in the manufacture of plastics, elastic fibres, and polyurethanes. It is also used in the synthesis of γ-butyrolactone (GBL), which is used to make polytetramethylene ether glycol, mainly going into spandex fibres, urethane elastomers, and copolyester ethers.
Butane-1,4-diol has psychoactive effects as it is metabolized into GHB, which can slow the heart and nervous system. It also increases the sleepiness and drowsiness caused by alcohol.
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It is used in the synthesis of epothilones, a new class of cancer drugs
Butane-1,4-diol, also known as 1,4-Butanediol, is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colourless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain. Butane-1,4-diol is used in the synthesis of epothilones, a new class of cancer drugs.
Butane-1,4-diol is used in the synthesis of epothilones, a new class of cancer drugs. It is also used in the stereoselective synthesis of (-)-Brevisamide. Butane-1,4-diol's largest use is within tetrahydrofuran (THF) production, which is used to make polytetramethylene ether glycol. This is used in spandex fibres, urethane elastomers, and copolyester ethers. Butane-1,4-diol is also used as a solvent in the chemical industry to manufacture gamma-butyrolactone and elastic fibres like spandex.
Butane-1,4-diol is used as a cross-linking agent for thermoplastic urethanes, polyester plasticizers, paints and coatings. It acts as an intermediate and is used to manufacture polytetramethylene ether glycol (PTMEG), polybutylene terephthalate (PBT) and polyurethane (PU). Butane-1,4-diol is used industrially as a solvent and in the manufacture of some types of plastics, elastic fibres and polyurethanes. It is also used as a plasticiser, for example in polyesters and cellulosics.
In organic chemistry, Butane-1,4-diol 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. At about 200 °C in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone. It is used to synthesize 1,4-butanediol diglycidyl ether, which is then used as a reactive diluent for epoxy resins.
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It is used as a solvent in the chemical industry
Butane-1,4-diol, also known as 1,4-butanediol, is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colourless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain.
Butane-1,4-diol is commonly used as a solvent in the chemical industry to manufacture gamma-butyrolactone and elastic fibres like spandex. It is also used as a cross-linking agent for thermoplastic urethanes, polyester plasticizers, paints and coatings.
In the chemical industry, butane-1,4-diol undergoes dehydration in the presence of phosphoric acid to yield tetrahydrofuran, an important solvent with various applications. Butane-1,4-diol is also used to manufacture polytetramethylene ether glycol (PTMEG), polybutylene terephthalate (PBT) and polyurethane (PU).
Butane-1,4-diol is used as a carrier solvent in printing ink and as a cleaning agent. It also functions as an industrial cleaner and a glue remover. Additionally, it serves as a humectant and viscosity controller, and can be used to mask odours.
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It has adverse effects when mixed with alcohol
Butane-1,4-diol, also known as 1,4-butanediol, is a primary alcohol and an organic compound. It is a colourless, viscous liquid derived from butane by placing alcohol groups at each end of its molecular chain. It is used in the synthesis of epothilones, a new class of cancer drugs, and in the stereoselective synthesis of (-)-Brevisamide. Butane-1,4-diol is also used in the production of plastics, solvents, elastic fibres, polyurethanes, and electronic chemicals.
When ingested, butane-1,4-diol is rapidly converted into gamma-hydroxybutyrate (GHB) by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase. GHB is a potent central nervous system depressant that can cause sleepiness, drowsiness, slowed breathing, and slowed heart rate. Mixing butane-1,4-diol with alcohol can increase these adverse effects, leading to a dangerous drug interaction. This is because the same enzymes that metabolize alcohol also metabolize butane-1,4-diol, resulting in a competition that slows the metabolism and clearance of both compounds.
The combination of butane-1,4-diol and alcohol can also potentiate the behavioural effects of alcohol, leading to increased intoxication. Emergency room patients who overdose on both ethanol and butane-1,4-diol often present with symptoms of alcohol intoxication initially. As the ethanol is metabolized, butane-1,4-diol is converted into GHB, resulting in a second period of intoxication. This combination can be life-threatening, and individuals have faced prosecution for possession of butane-1,4-diol under the Federal Analog Act due to its similarity to GHB.
Additionally, discontinuing the use of butane-1,4-diol can lead to withdrawal symptoms such as sweating, instability of blood pressure, tremors, nausea, vomiting, and mental disturbances. These symptoms are not relieved by alcohol, and only the use of butane-1,4-diol can improve the patient's condition. The risk of death caused by cerebral edema and acute renal failure is high during the withdrawal phase.
In conclusion, mixing butane-1,4-diol with alcohol can have adverse effects, including increased sleepiness, drowsiness, slowed breathing, and slowed heart rate. It can also lead to dangerous drug interactions and potentiate the behavioural effects of alcohol, resulting in a second period of intoxication. Discontinuing the use of butane-1,4-diol can lead to severe withdrawal symptoms, and alcohol does not alleviate these symptoms. Therefore, it is essential to exercise caution and seek medical advice when dealing with butane-1,4-diol and alcohol.
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It is used in the production of polybutylene terephthalate (PBT) plastic
Butane-1,4-diol, also called butane-1,4-diol (other names include 1,4-B, BD, BDO, and 1,4-BD), is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is used in the production of polybutylene terephthalate (PBT) plastic, an engineering polymer that is used as an insulator in the electrical and electronics industries. PBT is a thermoplastic (semi-)crystalline polymer and a type of polyester.
PBT is produced by the polymerization of 1,4-butanediol and terephthalic acid. It is a thermoplastic injection molding resin that resists solvents, shrinks very little during forming, is mechanically strong, and is heat-resistant up to 150 °C (or 200 °C with glass-fibre reinforcement). It can be treated with flame retardants to make it non-combustible. PBT is used for housings in electrical engineering and in automotive construction as plug connectors. It is also found in household items such as showerheads or irons, and in toothbrush fibers and false eyelashes.
PBT is closely related to other thermoplastic polyesters, such as PET (polyethylene terephthalate). Compared to PET, PBT has slightly lower strength and rigidity, slightly better impact resistance, and a slightly lower glass transition temperature. PBT and PET are sensitive to hot water above 60 °C (140 °F) and need UV protection if used outdoors.
The essential raw material for PBT is butane-1,4-diol, which is supplied by MERCK with a purity of at least 99%. Butane-1,4-diol is also used in the synthesis of γ-butyrolactone (GBL), which is used as a solvent in the chemical industry. It is also used as a cross-linking agent for thermoplastic urethanes, polyester plasticizers, paints and coatings.
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Frequently asked questions
Butane-1,4-diol is a primary alcohol and an organic compound with the formula HOCH2CH2CH2CH2OH. It is a colourless, viscous liquid.
Butane-1,4-diol is used industrially as a solvent and in the manufacture of plastics, elastic fibres, polyurethanes, and epoxy resins. It is also used in the synthesis of γ-butyrolactone (GBL), and as a component in the production of recreational drugs.
Butane-1,4-diol has psychoactive effects and can cause sleepiness and slowed breathing. It should not be taken with alcohol, pain medication, or sedatives. It may also cause nausea, vomiting, dizziness, sedation, vertigo, and potentially death if ingested in large amounts.
Butane-1,4-diol was first synthesized in 1890 by Dutch chemist Pieter Johannes Dekkers, who called it "tetramethylene glycol". It is now produced industrially through various chemical processes and has a world production of about one million metric tons per year.
