1,4-Butanediol

13 Jan.,2025

 

1,4-Butanediol

Summary sheet: 1,4-Butanediol 1,4-Butanediol Chemical Nomenclature Common names 1,4-Butanediol, 1,4-B, BD, BDO, One Comma Four, One Four Bee, Butylene Glycol, or One Four B-D-O Systematic name Butane-1,4-diol Class Membership Psychoactive class Depressant Chemical class Alkanediol Routes of Administration ' Oral Dosage Threshold < 0.5 mL Light 0.5 - 1 mL Common 1 - 2.5 mL Strong 2.5 - 4 mL Heavy 4 mL + Warning: Doses above 4 mL can induce heavy sleep and doses above 6 mL can lead to poisoning[2] Duration Total 3 - 5 hours Onset 20 - 60 minutes Peak 1 - 2 hours Offset 1.5 - 2 hours After effects 2 - 4 hours Interactions Stimulants DepressantsDissociatives


1,4-Butanediol (also known as 1,4-B, BDO, BD or 1,4-BD) is a depressant substance and a prodrug for GHB. It occurs as a thick, colorless liquid or solid depending on storage temperature (melting point of 20 '), and has a distinct bitter-sweet taste.[3] It is used as a recreational intoxicant with effects similar to alcohol and GHB.[4] 1 ml of 1,4-butanediol is equivalent to 1.4 g of Na-GHB.

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1,4-Butanediol is used industrially as a solvent and in the manufacture of some types of plastics, elastic fibers and polyurethanes. In organic chemistry, it is used for the synthesis of γ-butyrolactone (GBL).[5]

1,4-Butanediol, as well as GBL, will dissolve most types of plastic over time.[6] For this reason, it is recommended to only transport and store the drug using a glass container, standard gelatin capsules (not vegetarian), or high-density polyethylene plastic (also known as #2 recycled plastic). To check the type of plastic used on a bottle, one can look at the bottom for a number in the triangle-shaped recycling label.

Chemistry

1,4-Butanediol is classified as a subclass of alcoholic compounds called diols. Diols are named for having two alcohol (OH-) substitutions in their structure. 1,4-Butanediol is comprised of a butane chain of four carbon groups with an alcohol group bound to each terminal carbon of this chain. 1,4-Butanediol is named for these alcohol substitutions, which are located at R1 and R4. These alcohol substitutions make 1,4-Butanediol a polar liquid, which explains its good solubility in water.

Physically, it is a hygroscopic colorless oily liquid with a barely noticeable characteristic odor. Unlike GHB, 1,4-Butanediol has a distinct taste, described as being repulsive, plastic-like and chemical.

Pharmacology

Main article: GHB § Pharmacology

1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of GHB.[7]

It is converted into GHB in the liver by the enzymes alcohol dehydrogenase and aldehyde dehydrogenase, which is the same enzyme as alcohol.[8] 1,4-Butanediol is first converted into 4-hydroxybutaldehyde in the liver and is released into the bloodstream before returning to the liver to convert into GHB. This process results in a much more delayed onset than GBL or GHB.[9] 4-hydroxybutaldehyde, even though it is an aldehyde, does not have the same organ toxicity associated with acetaldehyde.[10] One reason could be the very fast metabolism to GHB.

The differing levels of dehydrogenase enzymes can vary between individuals, meaning that, like alcohol, effects can differ greatly between users. In many, this manifests as a slow onset of effects and a higher rate of aldehyde collecting in the bloodstream, causing more toxic side effects. Because of these pharmacokinetic differences, 1,4-butanediol tends to be less potent and with a slower onset than GHB but has a longer duration; the related compound GBL tends to be slightly more potent and faster to take effect but more short-acting than GHB.

Subjective effects

Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.

It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death '.

Experience reports

Anecdotal reports which describe the effects of this compound within our experience index include:

  • Experience:2ml 1,4-Butanediol - Not as good as alcohol

Additional experience reports can be found here

  • Erowid Experience Vaults: 1,4-Butanediol

Toxicity and harm potential

1,4-Butanediol is not active in its own right; its mechanism of action stems from its identity as a prodrug of GHB, meaning that it is rapidly converted into GHB in the body.

GHB is considered to be a safe and non-toxic substance when used responsibly or medically. The LD50 is above the active dosage, and there is no danger of acute toxicity when this compound is taken at appropriate dosages. However, it can be dangerous when used as a recreational drug or abused. There have been many negative reports from recreational users who have overdosed, combined GHB with alcohol or other drugs, or accidentally dosed themselves unexpectedly.[12]

One publication has investigated 226 deaths attributed to GHB.[13] Seventy-one deaths (34%) were caused by GHB alone while the other deaths were from respiratory depression caused by interaction with alcohol or other drugs.

To avoid a possible overdose of GHB/1,4-Butanediol, it is important to start with a low dose and work your way up slowly by increasing the dosage in small increments as the exact toxic dosage is unknown.

Accidental ingestions of 1,4-Butanediol have also occurred due to inadequate storage methods. If 1,4-Butanediol is put into a clear liquid, glass, or bottle, it can be easily mistaken for water. It is recommended to clearly label your 1,4-Butanediol in writing and dye the liquid with blue food coloring so it no longer resembles a drinkable beverage. It is also recommended to store your 1,4-Butanediol in a container that no one would drink out of.

It is strongly recommended that one use harm reduction practices when using this drug.

Neurotoxicity

In multiple studies, GHB has been found to impair spatial memory, working memory, learning and memory in rats with chronic administration.[14][15][16][17] These effects are associated with decreased NMDA receptor expression in the cerebral cortex and possibly other areas as well.[18]

One study found that repeated administration of GHB to rats for 15 days drastically reduced the number of neurons and non-neuronal cells within the hippocampus and in the prefrontal cortex. With doses of 10 mg/kg of GHB, they were decreased by 61% in the hippocampus region and 32% in the prefrontal cortex, and with 100 mg/kg, they were decreased by 38% and 9%, respectively. This paper demonstrates contradicting effects on neuronal loss, with lower doses (10 mg/kg) producing the most neurotoxicity, and higher doses (100 mg/kg) producing less.

Tolerance and addiction potential

GHB/1,4-Butanediol is moderately physically and psychologically addictive. The frequent use of GHB/1,4-Butanediol can cause withdrawal symptoms similar to those caused by other depressants such as alcohol and benzodiazepines if abruptly discontinued.[20][21] These symptoms seem to depend on the dosage and the length of time the drug was used for. Light to moderate users often experience anxiety, insomnia, sleep-related problems, and tremors whereas heavy use can cause severe withdrawal symptoms like delirium, psychosis, and hallucinations.[22][19]

Although there have been reported fatalities due to GHB/1,4-Butanediol withdrawal, reports are inconclusive and further research is needed.[23]

Tolerance will develop to the sedative-hypnotic effects within several weeks of continuous use. After cessation, the tolerance returns to baseline in 7 - 14 days. Withdrawal symptoms or rebound symptoms may occur after ceasing usage abruptly following a few weeks or longer of steady dosing, and may necessitate a gradual dose reduction.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • Depressants (1,4-Butanediol, 2M2B, alcohol, benzodiazepines, barbiturates, GHB/GBL, methaqualone, opioids) - This combination potentiates the muscle relaxation, amnesia, sedation, and respiratory depression caused by one another. At higher doses, it can lead to a sudden, unexpected loss of consciousness along with a dangerous amount of depressed respiration. There is also an increased risk of suffocating on one's vomit while unconscious. If nausea or vomiting occurs before a loss of consciousness, users should attempt to fall asleep in the recovery position or have a friend move them into it.
  • Dissociatives - This combination can unpredictably potentiate the amnesia, sedation, motor control loss and delusions that can be caused by each other. It may also result in a sudden loss of consciousness accompanied by a dangerous degree of respiratory depression. If nausea or vomiting occurs before consciousness is lost, users should attempt to fall asleep in the recovery position or have a friend move them into it.
  • Stimulants - Stimulants mask the sedative effect of depressants, which is the main factor most people use to gauge their level of intoxication. Once the stimulant effects wear off, the effects of the depressant will significantly increase, leading to intensified disinhibition, motor control loss, and dangerous black-out states. This combination can also potentially result in severe dehydration if one's fluid intake is not closely monitored. If choosing to combine these substances, one should strictly limit themselves to a pre-set schedule of dosing only a certain amount per hour until a maximum threshold has been reached.

Legal status

  • United States: While 1,4-butanediol is not currently scheduled federally in the United States, a number of states have classified it as a controlled substance. Additionally, individuals have been prosecuted for this substance under the Federal Analogue Act as being substantially similar to GHB.[24] A federal district court in Chicago ruled that 1,4-butanediol could not be considered an analogue of GHB under federal law, and the Seventh Circuit Court of Appeals upheld that ruling.[25]
  • United Kingdom: In the United Kingdom, 1,4-butanediol was scheduled in December (along with another GHB precursor, gamma-butyrolactone) as a Class C controlled substance.
  • Germany: 1,4-butanediol is not a controlled substance under the BtMG (Narcotics Act) or the NpSG (New Psychoactive Substances Act).[26][27] It is legal, as long as it is not sold for human consumption, according to §2 AMG.[28]
  • Canada: It is controlled as a Schedule VI precursor in Canada.
  • Switzerland: 1,4-Butanediol is a controlled substance specifically named under Verzeichnis E.[29]

See also

  • Responsible use
  • Depressants
  • GHB
  • GBL
  • GABA
  • 1,4-Butanediol (Wikipedia)
  • 1,4-Butanediol (Erowid Vault)
  • 1,4-Butanediol (TiHKAL / Isomer Design)

References

Characteristics That Set Urethane Grade 1,4-Butanediol ...

1,4-butanediol (BDO/1,4-BD) is a versatile liquid diol intermediate with reactive primary hydroxyl functionality and a linear structure that lends itself to formulating polyurethanes with a good balance of hardness and low temperature flexibility; high strength and durability; and thermal stability. 

1,4-butanediol is characterized by'

  • A molecular weight (MW) of 90.12.
  • An equivalent weight (EW) of 45.06.
  • And a hydroxyl value of mg KOH/g.  
  • A melting point of 20.1°C (68.2')
  • A boiling point of 235°C (455')
  • A flash point of 121°C (250')

While 1,4-BDO has a number of uses as a polymer intermediate, BDO plays a key role in the creation of polyurethanes, with urethane grade BDO being particularly advantageous because of its low moisture content (< 150 ppm moisture specification) and very high purity (> 99.85 % purity by gc).

In this article, we'll explain 5 key properties that set urethane grade BDO apart, covering everything from its function as a chain extender to its various applications.

1. The Role of 1,4-Butanediol (BDO/1,4-BD) as a Polyurethane Building Block

The properties of a polyurethane greatly depend on the structure of the molecular backbone, and chain extenders play a significant role in enhancing the final mechanical properties of polyurethanes.

In polyurethanes, BDO is used as a urethane chain extender (difunctional reactants like BDO are considered chain extenders while reactants with higher functionality are considered crosslinkers) and an intermediate for polyester polyols.

And, when it comes to MDI systems, the chain extender of choice for most processors is 1,4-BDO. Functioning in this role, BDO reacts with MDI or MDI-based prepolymers and H12 MDI systems to create the 'hard segment' domains of polyurethanes. 1,4-butanediol yields crystalline urethane domains that efficiently microphase separate to afford tough elastomeric networks.  

In thermoplastic polyurethane (TPU) compositions, uncrosslinked BDO-MDI domains can be melted and will flow at elevated temperatures to allow thermoplastic processing. The associated networks reform when cooled to form tough elastomeric compositions.

For polyurethanes in which butanediol is the chain extender in the hard segment (MDI based), you can find the following structural unit:

   -NH-CO-O-CH2CH2CH2CH2-O-CO-NH-C6H4-CH2-C6H4-

1,4-butanediol also serves as an intermediate for polyester polyols. BDO polyester polyols, such as poly (butylene adipate) polyol, help create the 'soft segment' domains in polyurethane elastomers.  

Using BDO polyester polyol, formulators develop polyurethanes with excellent mechanical properties over a broad temperature range. These polyurethanes exhibit good abrasion resistance; cut and chip resistance; excellent oil, grease, and chemical resistance; and weatherability.  
 

2. The Effectiveness of 1,4-Butanediol as a Chain Extender

To understand the popularity of 1,4-butanediol as a chain extender, it's important to recognize an odd-even effect in polyurethane intermediates.   

The first criterion for an effective diol urethane intermediate is linearity; the second criterion is that it ideally contains an even number of carbon atoms (i.e., the number of CH2 groups in the repeating chain).  

Molecular-level chain packing of the individual hard and soft segments of polyurethanes benefits the overall performance properties of the resulting elastomers. For polyester polyols and diol chain extenders, an odd-even carbon number effect has been observed. 

For example, in adipate polyester polyols based on diols with an even number of carbon atoms (EG-2, BDO-4, and HDO-6), the melting points, glass transition temperatures, and overall performance properties are higher than comparable systems based on diols with an odd number of carbon atoms (PrDO-3 and PeDO-5).

Particularly outstanding is the high degree of crystallinity and melt enthalpy (i.e., heat required to melt the crystalline hard segment) in MDI-BDO hard segments of a polyurethane. Please see the chart below for an example.


Melt Enthalpy for MDI/Diol Segments in BDO/Adipate Polyester Polyol based Polyurethanes

Diol in Hard Block

ΔH(J/g)- TM

TM°C

EG

0.9

175

1,3-PDO

0.4

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145

BDO

2.8

148

1,5-PDO

0.14

167

1,6-HDO

0.69

156

(Source)

The odd-even effect is attributed to the crystal packing of the hard segment and hydrogen bonding between neighboring urethane molecules.

For even-number chain extenders, modelling has shown that the molecular chains align better, and interchain hydrogen bonding is facilitated with chain extenders like BDO.  This drives the beneficial phase separation between the hard and soft polymeric segments. In fact, many studies have demonstrated that the properties of a polyurethane are very dependent on the extent and perfection of this phase separation.

While ethylene glycol (EG) is also an even-carbon-number diol chain extender, it is not a good alternative to BDO.

There are two disadvantages observed with EG: poor miscibility with many polyols leading to processing and performance disadvantages and the polar nature of EG leading to a reduction in hydrolysis resistance.  

Otherwise, EG is a good chain extender and polyester intermediate, affording polyurethanes with good mechanical properties.
 

3. The Processing Conditions for 1,4-Butanediol Chain Extenders

As a liquid diol, 1,4-butanediol can be used as a chain extender at room temperature in MDI and aliphatic diisocyanate systems.

Processing temperature and catalyst loading levels impact the pot life of diol/MDI systems. While uncatalyzed systems can have a pot life of 10'20 minutes at 70°C, processing at higher temperatures or using catalysts will significantly reduce the pot life. Tin and titanate catalysts are commonly used to increase the reaction rate of the diol with the isocyanate.

In addition, BDO freezes at 20°C (68°F). Therefore, it's important to maintain BDO above the freezing point to avoid crystallization in the equipment lines and phase separation in a B-Side formulation.  

BDO is also hygroscopic and requires maintenance in an inert environment to avoid moisture absorption. With its low moisture content, urethane grade BDO permits processors good control of stoichiometry by avoiding the reaction of H2O with isocyanates and concomitant release of CO2 gas bubbles.
 

4. The Mechanical Properties of PTMEG/MDI/1,4-Butanediol  

The mechanical properties of a representative polyurethane based on a PTMEG /MDI prepolymers and BDO as the chain extender are referenced below.  

This table shows the effect of increased hard block content (higher NCO %) on the elastomeric properties. Also note that the tensile properties and tear strength increased with increased hardness.

Mechanical Properties of MDI-PTMEG Prepolymer with BDO Chain Extender

NCO, %

6.60

8.20

Hardness, Shore A

85A

90A

100 % Modulus, psi

830

Tensile Strength, psi

Elongation, %

560

500

Tear Strength, pli

500

540

Bashore Rebound, %

70

64

(Source)
 

5. The Polyurethane Applications of 1,4-Butanediol

Because of BDO's consistency, durability, and other performance attributes, end-use applications for 1,4-butanediol in polyurethanes are wide ranging, both as a chain extender and in polyester polyols.

The main polyurethanes produced using BDO are solid and cellular elastomers.  Applications include a vast array of performance cast urethane parts, such as...

  • Wheels, rollers, and belts.  
  • Recreational equipment.
  • Pipe linings and pipeline products.
  • Pump liners and parts.
  • Hydrocyclones.
  • Conveyor belts.  

Other applications include'

  • High-performance adhesives, sealants, and coatings.
  • RIM and TPU parts.
  • Automotive components.
  • Appliance parts.
  • Footwear.

Polyurethanes based on BDO systems perform well in aggressive environments'for example, exposures in mining, mineral, and oil field operations and in medical devices.

Purchasing Urethane Grade BDO: Availability and Packaging

BDO is a readily available intermediate with a favorable price point. At Gantrade, we offer our urethane grade BDO as a general purpose grade.  

You can select packaging of either 200 Kg. (441 lb. net) factory-sealed drums or ISO tanks, depending on your requirements.   

For more information, please visit cas 110 63 4 bulk.