1,4-BUTANEDIOL (1,4- BÜTANDİOL)
1,4-BUTANEDIOL- 1,4-bütandiol
CAS NUMBER : 110-63-4
EC NUMBER : 203-786-5
Synonyms:
1,4-BUTANEDIOL; Butane-1,4-diol; 110-63-4; 1,4-Butylene glycol; Tetramethylene glycol; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; Tetramethylene 1,4-diol ; Sucol B; 1,4-BD; 1,4-BUTANEDİOL
1,4-BUTANEDIOL; 1,4-BÜTANEDIOL; 1,4-BUTANEDiOL; 1 4-BUTANEDIOL; 1,4 BUTANEDIOL; 1,4-BUTANE DIOL; 1,4-BUTANEDIOLE; 1,4-BUTANEDİOLE; 1,4-BÜTANEDİOLE; 1,4-BÜTANDİOL; 1,4-BÜTAN DİOL; 1,4 - BÜTANDİOL; 1,4-BÜTANDİOLE; 1,4 BÜTANDİOL; 1,4-BÜTAN DİOLE; 1 4 BÜTANDİOL; 1,4-butanedıol; 1,4-bütanedıol; 1,4-butanediol; 1 4-butanedıol; 1,4 butanedıol; 1,4-butane dıol; 1,4-butanedıole; 1,4-butanediole; 1,4-bütanediole; 1,4-bütandiol; 1,4-bütan diol; 1,4 - bütandiol; 1,4-bütandiole; 1,4 bütandiol; 1,4-bütan diole; 1 4 bütandiol; 1,4-Butanedıol; 1,4-Bütanedıol; 1,4-Butanediol; 1 4-Butanedıol; 1,4 Butanedıol; 1,4-Butane Dıol; 1,4-Butanedıole; 1,4-Butanediole; 1,4-Bütanediole; 1,4-Bütandiol; 1,4-Bütan Diol; 1,4 - Bütandiol; 1,4-Bütandiole; 1,4 Bütandiol; 1,4-Bütan Diole; 1 4 Bütandiol
Butane-1,4-diol; 110-63-4; 1,4-Butylene glycol; Tetramethylene glycol; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; Tetramethylene 1,4-diol; Sucol B; 1,4-BD; DIOL 14B; Agrisynth B1D; HO(CH2)4OH; NSC 406696; CCRIS 5984; 1,4-Dihdyroxybutane; HSDB 1112; EINECS 203-786-5; HOCH2CH2CH2CH2OH; BRN 1633445; AI3-07553; CHEBI:41189; WERYXYBDKMZEQL-UHFFFAOYSA-N; MFCD00002968; DSSTox_CID_4666; DSSTox_RID_77492; DSSTox_GSID_24666; BDO; BU1; CAS-110-63-4; UNII-7XOO2LE6G3; 4-hydroxybutanol; 1,4butanediol; 1.4-butanediol; Dabco BDO; 1,4-butandiol; 1,4-butane diol; 1,4-butane-diol; butane 1,4-diol; butane diol-1,4; butane-1-4-diol; 1,4- butandiol; Buta
n-1.4-diol; 1.4 - butanediol; butanediol, 1,4-; 1,4 butylene glycol; ACMC-1BRE8; 1,4-Butanediol, 99%; AC1L1Q6L; AC1Q7CS0; WLN: Q4Q; versalink curative 1,4 bdo; 7XOO2LE6G3; akos bbs-00004303; 4-01-00-02515 (Beilstein Handbook Reference); KSC175Q8N; MLS001061198; 1,4-Butanediol 4 M solution; CHEMBL171623; DTXSID2024666; CTK0H5886; KS-00000WMZ; HMS3039N12; LTBB001138; 1,4-Butanediol, 99% 250g; ZINC1599375; Tox21_202245; Tox21_303040; ANW-16175; LS-512; NSC406696; STL283940; AKOS000118735; 1,4-Butanediol, for synthesis, 98%; DB01955; MCULE-2010022287; NSC-406696; RL02831; RP18542; RTR-032026; TRA0075312; 1,4-Butanediol, ReagentPlus(;R), 99%; NCGC00090733-01; NCGC00090733-02; NCGC00257119-01; NCGC00259794-01; 28324-25-6; AJ-27941; AK160801; AN-22614; BP-21418; CJ-05671; CJ-25700; KB-10525; OR012020; SC-79277; SMR000677930; 1,4-Butanediol, ReagentPlus(R), >=99%; TR-032026; B0680; FT-0606811; ST24046254; 3379-EP2272849A1; 3379-EP2292597A1; 3379-EP2301919A1; 3379-EP2305668A1; 1,4-Butanediol, Vetec(TM) reagent grade, 98%; 48881-EP2270101A1; 48881-EP2275417A2; 48881-EP2284162A2; 48881-EP2284163A2; 48881-EP2284165A1; 48881-EP2295399A2; 48881-EP2295438A1; 48881-EP2308865A1; 48881-EP2311841A1; 48881-EP2371797A1; 48881-EP2371798A1; 48881-EP2371805A1; 48881-EP2380568A1; 48881-EP2380873A1; I14-2693; J-503971; J-512798; 3B1-003910; 3B1-004958; 3B1-007610; 3B1-007837; F0001-0222; Z1259087047; InChI=1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H; UNII-TMS4MGA0H4 Component; WERYXYBDKMZEQL-UHFFFAOYSA-N; 732189-03-6; 1,4-Butanediol; 1,4-B; BD; One Comma Four; One Four Bee; Butylene Glycol; or One Four B-D-O; BUTANE-1,4-DIOL , TETRAMETHYLENE GLYCOL 1,4-BUTANDIOL; 1,4-Butanediol; ,4-Butanediol 1,4-butylene glycol butylene glycol; ,4-Butylene glycol; ,4-Dihydroxybutane; ,4-Tetramethylene glycol; Butan-1,4-diol; Butane-1,4-diol; Butano-1,4-diol; Butylene glycol; Dabco DBO ;Diol 14B; NSC 406696; Polycure D; POLYESTER OF 1,4-BUTANEDIOL; Sucol B; Tetramethylene 1,4-diol; Tetramethylene glycol; Vibracure A 250; ZM 0025; BUTANEDIOL; 1,4-BUTYLENE GLYCOL; 1,4-TETRAMETHYLENE GLYCOL; 1,4-Butanediol; Butane-1,4-diol; 1,4-Butylene glycol; Tetramethylene glycol;; 110-63-4; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; BDO; Butanediol-; 1,4; 1,4-BD; 1,4-BDO; 1,4-Tetramethylene ; 11,4-Butanediol ; 1,4-Butandiol ; 1,4-Butanediol ; 110-63-4 ; butane-1,4-diol; (3S)-Butane-1,3-diol; (S)-()-1,3-Butanediol; [110-63-4]; 1,4-BD; 1,4-butane diol; 1,4-BUTANEDIOL, 99%; 1,4-butylene glycol; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; 1,4-丁二醇 ; 1589-49-7 ; 203-786-5 [EINECS]; 25265-75-2 ; 28324-25-6 ; 4-01-00-02515 ; 53504-41-9; 732189-03-6 ; BDO; BU1; BU2; Butane diol-1,4; BUTANEDIOL ; Butylene glycol; Dabco BDO; HO(CH2)4OH; HOCH2CH2CH2CH2OH; InChI=1/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H; MFCD00002968 ; POLYURETHANE ; ST5214425; Tetramethylene 1,4-diol; bütandiol; bütandiyol; diyol; bütanediyol; butanediyol; BÜTANDİYOL; BUTANDİYOLE; 14bütandiol; 14butandiyole; 14bütandiyol; 1,4-Butylene glycol, Tetramethylene glycol; CAS Number 110-63-4; Linear Formula HO(CH2)4OH; Molecular Weight 90.12; Beilstein Registry Number 1633445; EC Number 203-786-5; MDL number MFCD00002968; pubChem Substance ID 24872855; 1,4-Butanediol; 1,4-B; BD; One Comma Four; One Four Bee; Butylene Glycol; One Four B-D-O; Butane-1,4-diol; 1,4-Butylene glycol; 1,4-Butylene glycol; 1,4-Butanediol; InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2; WERYXYBDKMZEQL-UHFFFAOYSA-N; 110-63-4; Diol 14B; Sucol B; Tetramethylene glycol; 1,4-Butylene glycol; 1,4-Dihydroxybutane; 1,4-Tetramethylene glycol; Butane-1,4-diol; Butanediol; 1,4-BD; Tetramethylene 1,4-diol; BDO; Butylene glycol; Dabco BDO; Butane diol-1,4; NSC 406696; 1,4-butylene glycol; 1,4-dihydroxybutane; tetramethylene glycol; 1,4-tetramethylene glycol; tetramethylene-1,4diol; butylene glycol; butanediol; butane-1,4-diol; BUTANE-1,4-DIOL; BUTANEDIOL; 1,4-BUTANEDIOL; BUTYLENE GLYCOL; 1,4-BUTYLENE GLYCOL; DABCO DBO; DIHYDROXYBUTANE; 1,4-DIHYDROXYBUTANE; DIOL 14B; POLYCURE D; SUCOL B; TETRAMETHYLENE 1,4-DIOL; TETRAMETHYLENE GLYCOL; 1,4-TETRAMETHYLENE GLYCOL; Butanediol; 1,4-; (1,4-tetramethylene glycol) (110-63-4); 1,4-Butylene Glycol; 1,4-Dihydroxybutane; Tetramethylene Glycol; BDO; 1,4-bD; sucolb; diol14b; Sucol B; Diol 14B; Dabco BDO; Butanediol; agrisynthb1d; 4-Butanediol; 1,4-Butanediol ≥99%; 1,4-BD; 1,4-Butylene glycol; 1,4-Dihydroxybutane; 1,4-Tetramethylene; glycol; BDO; Butane diol-1,4; Butane-1,4-diol; Butanediol; Butylene glycol; Dabco BDO; Diol 14B; NSC 406696; Sucol B; Tetramethylene; 1,4-diol; Tetramethylene glycol; InChI=1S/C4H10O2/c5-3-1-2-4-6/h5-6H,1-4H2; InChI Key; WERYXYBDKMZEQL-UHFFFAOYSA-N; Formula; C4H10O2; SMILES; OCCCCO; Molecular Weight1; 90.12; CAS; 110-63-4; 732189-03-6; ECHA EINECS; REACH Pre-Reg: 03-786-5; FDA UNII:7XOO2LE6G3; Nikkaji Web:J5.097K; Beilstein Number:1633445; MDL:MFCD00002968; agrisynth B1D; 1,4-butandiol; butane-1,4-diol; 1,4-butanediol; 1,4- butylene glycol; 1,4-dihydroxybutane; tetramethylene glycol; 1,4-tetramethylene glycol; Butane-1,4-diol; 1,4-Butylene glycol; 1,4-Dihdyroxybutane; Tetramethylene 1,4-diol; 1,4-Tetramethylene glycol; Tetramethylene glycol; 1,4; 14bd; 1,4-bütandiol ;1,4 bütandiol; 1 4-bütandiol; 1 4 bütandiol
1,4-Butanediol
14BG (1,4-Butanediol) is a straight chain glycol with hydroxyl groups on both ends. It is used as a raw material for high performance polyester and polyurethane resins as well as for industrial chemicals like tetrahydrofuran and gamma-butyrolactone. Since 1982, Mitsubishi Chemical's Yokkaichi plant has produced high-purity, high-quality 1,4-Butanediol from butadiene using our proprietary technology.
CAS: No. 110-63-4 (T)
EINECS: No. 203-786-5
Applications
Specifications/Quantities
Inquiries
Characteristics [close]
1,4-Butanediol (1,4-Butanediol (BDO), 1,4-Butylene glycol (BG), 1,4-Dihydroxy butane, Tetramethylene glycol (TMG)) is the 4-carbon atoms straight-chain glycol (diol, dihydric alcohol) with a hydroxyl groups at both ends.
Common Names 1,4-Butanediol
1,4-Butylene Glycol
1,4-Dihydroxybutane
Tetramethylene Glycol
Structure 1,4-Butanediol
CAS No. 110-63-4
Japan, Chemical Substances Control Law METI-No. (2)-235
Japan, Poisonous and Deleterious Substances Control Law Not applicable
Japan, Fire Services Law Hazardous material Class 4 Petroleums No.3, water-soluble, Hazardous Rank III
Molecular Weight 90.1
Appearance Clear colorless liquid (wax-like solid when cold)
Odor Faint
Specific Gravity (25/4℃) 1.012
Viscosity(mPa･s) 65（at 25℃）
Boiling Point (℃) 228
Freezing Point (℃) 20.1
Flash Point (℃) 134
Vapor pressure (kPa) 0.001（27℃）
Heat of Vaporization (kJ/mol) 64.9（228℃）
Heat capacity (kJ/kg･K) 2.21（25℃）
Thermal conductivity (W/m･K) 0.22（25℃）
Volume resistivity (Ω • cm) 2.2×107（23℃）
Mitsubishi Chemical's 1,4-Butanediol (1,4-Butanediol (BDO), 1,4-Butylene glycol (BG), 1,4-Dihydroxy butane, Tetramethylene glycol (TMG)) is synthesized from butadiene using our proprietary technology. It is used as a raw material for various synthetic resins of controllable color. Using thorough quality control, 1,4-Butanediol can be offered with low moisture content.
Applications [close]
1,4-Butanediol (1,4-Butanediol (BDO), 1,4-Butylene glycol (BG), 1,4-Dihydroxy butane, Tetramethylene glycol (TMG)) is a raw material for polyester and polyurethane resins (chain extender, hard segment) that show excellent characteristics.
These products find a wide range of applications including everyday consumer products such as clothing and shoe soles, consumer durables such as electrical appliances and cars, industrial materials such as machine parts, as well as medical products. It is anticipated that the use of these polymers will continue to expand.
Main Applications
PBT (Polybutylene terephthalate) Resin Raw Material
Because 1,4-Butanediol diol (dibasic alcohol) is used as a raw materail, PBT is a great engineering plastic with low water-absorbance and an excellent balance of mechanical and electrical properties. Applications are expanding beyond the original electrical/electronic parts and automotive parts markets.
Polyurethane Resin Raw Material
By using 1,4-Butanediol diol for the chain extender, urethane elastomers can be made with excellent mechanical properties and high resistances to heat, oil, and impact.
Other Polyester Raw Materials
1,4-Butanediol is widely used to make various polyester resins and plasticizers.
Raw Material for Industrial Chemicals (Tetrahydrofuran, Gamma-Butyrolactone)
Tetrahydrofuran and gamma-butyrolactone are produced indutrially by dehydration or dehydrogenation of 1,4-Butanediol.
Storage and Handling
1,4-Butanediol is hygroscopic and will be degraded by oxygen, so the storage container should be sealed with dry nitrogen. It is recommended that storage be at 25-40℃. Below 20℃ 1,4-Butanediol will be solid, but can be mellted by careful heating. To melt solidified 1,4-Butanediol in drums, hold overnight at 50-70℃. 1,4-Butanediol is classified under the Japanese Fire Services Act as a hazardous material, Class 4, Petroleums No.3, water soluble, Hazardous Rank III. Volatility is low, and 1,4-Butanediol is unlikely to catch fire by itself at room temperature. However, in case it is burning, dry chemical, foam (alcohol resistant), or large amounts of water are effective. 1,4-Butanediol has relatively low toxicity and is a relatively safe chemical. When handling, however, protective equipment such as protective gloves and goggles should be worn.
Specifications/Quantities [close]
Product Specifications
Item Specification
Hue (Hazen) <10
Moisture (%) <0.05
Specific Gravity (25/4℃) 1.012 - 1.016
Purity (%) >99.5
1,4-butanediol appears as odorless colorless liquid or solid (depending upon temperature). (USCG, 1999)
CAMEO Chemicals
Butane-1,4-diol is a butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16℃) with a high boiling point (230℃), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF). It has a role as a neurotoxin, a protic solvent and a prodrug. It is a butanediol and a glycol.,4-butanediol appears as odorless colorless liquid or solid (depending upon temperature). (USCG, 1999)
CAMEO Chemicals
Butane-1,4-diol is a butanediol that is butane in which one hydrogen of each of the methyl groups is substituted by a hydroxy group. A colourless, water-miscible, viscous liquid at room temperature (m.p. 16℃) with a high boiling point (230℃), it is mainly used for the production of other organic chemicals, particularly the solvent oxolane (also known as tetrahydrofuran or THF). It has a role as a neurotoxin, a protic solvent and a prodrug. It is a butanediol and a glycol.
1,4-Butanediol
1,4-butanediol.svg
1,4-Butanediol-3D-balls.png
Names
IUPAC name
Butane-1,4-diol
Other names
Tetramethylene glycol
Identifiers
CAS Number
110-63-4 ☑
3D model (JSmol)
Interactive image
Interactive image
ChEBI
CHEBI:41189 ☑
ChEMBL
ChEMBL171623 ☑
ChemSpider
13835209 ☑
DrugBank
DB01955 ☑
ECHA InfoCard 100.003.443
EC Number
203-786-5
PubChem CID
8064
RTECS number
EK0525000
UNII
7XOO2LE6G3 ☑
CompTox Dashboard (EPA)
DTXSID2024666 Edit this at Wikidata
InChI[show]
SMILES[show]
Properties[1][2]
Chemical formula
C4H10O2
Molar mass 90.122 g·mol-1
Density 1.0171 g/cm3 (20 °C)
Melting point 20.1 °C (68.2 °F; 293.2 K)
Boiling point 235 °C (455 °F; 508 K)
Solubility in water
Miscible
Solubility in ethanol Soluble
Magnetic susceptibility (χ)
-61.5·10-6 cm3/mol
Refractive index (nD)
1.4460 (20 °C)
Hazards[2][3]
GHS pictograms Acute Tox. (oral) 4
GHS Signal word Warning
GHS hazard statements
H302
GHS precautionary statements
P264, P270, P301+312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
110
Flash point (open cup) 121 °C (250 °F; 394 K)
Autoignition
temperature
350 °C (662 °F; 623 K)
Related compounds
Related butanediols
1,2-Butanediol
1,3-Butanediol
2,3-Butanediol
cis-Butene-1,4-diol
Related compounds
Succinaldehyde
Succinic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
1,4-Butanediol, colloquially known as BD, is a primary alcohol, and an organic compound, with the formula HOCH2CH2CH2CH2OH. It is a colorless viscous liquid. It is one of four stable isomers of butanediol.
Synthesis
In its industrial synthesis, acetylene reacts with two equivalents of formaldehyde to form 1,4-butynediol. 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. It is also manufactured 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.[4]
A biological route to BDO has been commercialized that uses a genetically modified organism.[5] The biosynthesis proceeds via 4-hydroxybutyrate.
Industrial use
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, 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.[6] At about 200 °C in the presence of soluble ruthenium catalysts, the diol undergoes dehydrogenation to form butyrolactone.[7]
World production of 1,4-butanediol was claimed to be about one million metric tons per year and market price is about US$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).[8]
Almost half of it is dehydrated to tetrahydrofuran to make fibers such as Spandex.[9] The largest producer is BASF.[10]
Toxicity and use as a recreational drug
FDA warning against products containing GHB and its prodrugs, such as 1,4-butanediol.
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". It exerts effects similar to γ-hydroxybutyrate (GHB), which is a metabolic product of 1,4-butanediol.[11][12] When mixed with other drugs, misuse of 1,4-butanediol has resulted in addiction and death.[13]
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.[14] 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.[14][15] 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.[14]
Metabolic pathway of 1,4-butanediol, γ-butyrolactone and γ-hydroxybutyric acid (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.[15] 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 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 in rats of 1,4-butanediol.[16] This contradicts the hypothesis of 1,4-butanediol having inherent alcohol-like pharmacological effects.
Like GHB, 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,[17] a number of states have classified 1,4-butanediol as a controlled substance. Individuals have been prosecuted for 1,4-butanediol under the Federal Analog Act as substantially similar to GHB.[18] A federal case in New York in 2002 ruled that 1,4-butanediol could not be considered an analog of GHB under federal law,[19] but that decision was later overturned by the Second Circuit.[20] However, a Federal District Court in Chicago ruled that 1,4-butanediol could not be considered an analog of GHB under federal law, and the Seventh Circuit Court of Appeals upheld that ruling.[21] 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
See also: Bindeez
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.[22] 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.[23]
Property Name of 1,4-Butanediol: Property Value Reference
Molecular Weight of 1,4-Butanediol: 90.12 g/mol
XLogP3 of 1,4-Butanediol: -0.8 XLogP3 3.0
Hydrogen Bond Donor Count of 1,4-Butanediol: 2
Hydrogen Bond Acceptor Count of 1,4-Butanediol: 2
Rotatable Bond Count of 1,4-Butanediol: 3
Exact Mass of 1,4-Butanediol: 90.06808 g/mol PubChem 2.1
Monoisotopic Mass of 1,4-Butanediol: 90.06808 g/mol PubChem 2.1
Topological Polar Surface Area of 1,4-Butanediol: 40.5 Ų Cactvs 3.4.6.11
Heavy Atom Count of 1,4-Butanediol: 6 PubChem
Formal Charge of 1,4-Butanediol: 0 PubChem
Complexity of 1,4-Butanediol: 17.5
Isotope Atom Count of 1,4-Butanediol: 0
Defined Atom Stereocenter Count of 1,4-Butanediol: 0
Undefined Atom Stereocenter Count of 1,4-Butanediol: 0
Defined Bond Stereocenter Count of 1,4-Butanediol: 0
Undefined Bond Stereocenter Count of 1,4-Butanediol: 0
Covalently-Bonded Unit Count of 1,4-Butanediol: 1
Compound Is Canonicalized of 1,4-Butanediol: Yes
Experimental Properties of 1,4-Butanediol:
3.2.1Physical Description of 1,4-Butanediol: HelpNew Window
1,4-butanediol appears as odorless colorless liquid or solid (depending upon temperature). (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
CAMEO Chemicals
Liquid
EPA Chemicals under the TSCA
COLOURLESS VISCOUS LIQUID.
ILO International Chemical Safety Cards (ICSC)
3.2.2Color/Form HelpNew Window
Colorless, oily liquid
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 224
Hazardous Substances Data Bank (HSDB)
Colorless liquid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 268
Hazardous Substances Data Bank (HSDB)
Colorless, viscous liquid or crystals; to needles on chilling
Catalepsy and Comparing Gamma-Hydroxybutyrate, 1,4-Butanediol, and Gamma-Butyrolactone
Siripan Phattanarudee, ... Pasarapa Towiwat, in Neuropathology of Drug Addictions and Substance Misuse, 2016
Summary Points
•
1,4- Butanediol and GBL are chemically related to GHB and, by conversion into GHB in the body, produce effects that are similar to those found following GHB administration.
•
As 1,4- Butanediol and GBL require metabolic conversion into the active compound GHB, via alcohol dehydrogenase and aldehyde dehydrogenase for 1,4- Butanediol, and by nonenzymatic hydrolase or lactonase for GBL, it is plausible that this metabolic conversion can account for differences in the onset and duration of the pharmacological effects of both 1,4- Butanediol and GBL compared with GHB.
•
When comparing the catalepsy produced by GHB, GBL, and 1,4- Butanediol given in equimolar doses, the earliest onset of effects can be seen from GHB and GBL, followed by 1,4- Butanediol. The effect is dissipated by approximately 60 min for GBL and 1,4- Butanediol, while that of GHB's effect disappeared at approximately 70 min after drug administration.
•
1,4- Butanediol and GBL share some of the pharmacological effects of GHB: the acute cataleptic effect, but not the development of tolerance.
•
From the slower onset of cataleptic effect from 1,4- Butanediol administration, together with the decreased tolerance development, as shown in this study, 1,4- Butanediol may have lower abuse liability compared with GHB or GBL.
3.15.3.2 1,4-Butanediol (1,4-BDO)
3.15.3.2.1 Chemical route
1,4- Butanediol is an important raw material in manufacturing plastics, elastic fibers, and films. According to a US DOE report (Industrial Bioproducts: Today and Tomorrow), 49, 22, and 21% of Butanediol produced are used to make THF, polybutylene terephthalate (PBT), and GBL, respectively. In high-temperature condition, THF is synthesized from 1,4- Butanediol in the presence of phosphoric acid, while GBL is dehydrogenated from 1,4- Butanediol in the presence of soluble ruthenium catalyst. Five well-known chemical processes to produce 1,4- Butanediol are summarized in Figure 3. Reppe chemistry, as one of the earlier technologies for 1,4- Butanediol production, includes the production of 1,4-butynediol from acetylene and formaldehyde and the catalytic hydrogenation of 1,4-butynediol to 1,4- Butanediol (Figure 3(a)). The largest share of the world Butanediol production (by BASF, ISP and Dupont) still relies on this process [3]. The Lyondell process utilizes propylene oxide as the starting material and proceeds in the sequence of isomerization of propylene, hydroformylation of allyl alcohol, and hydrogenation of 4-hydroxybutyraldehyde (Figure 3(b)) [35]. The third process is the butadiene acetoxylation process, patented by Mitsubishi-Kasei (Figure 3(c)). Butadiene is reacted with acetic acid and oxygen to produce 1,4-diacetoxy-2-butene, which is then hydrogenated over a catalyst to form a saturated intermediate and subsequently hydrolyzed to make 1,4- Butanediol [35]. The fourth and fifth processes for 1,4- Butanediol production use butane as a starting material. In the fourth process, butane is directly oxidized to maleic anhydride, which is then reacted with methanol to produce dimethyl maleate [35]. Dimethyl maleate is hydrogenated to produce 1,4- Butanediol (Figure 3(d)) [35]. The Davy McKee process requires the esterification of maleic acid and subsequent hydrogenation to produce 1,4- Butanediol
Summary
1,4-butanediol (1,4-BD) is a colorless, viscous liquid derived from butane by placement of
alcohol groups at each end of its molecular chain and is one of four stable isomers of
butanediol. 1,4-Butanediol has widespread industrial use. It is used in the production of spandex
fibers, urethane elastomers, and copolyester ethers. Sizable quantities of 1,4-Butanediol are also used
to make gamma-butyrolactone (GBL), which has outlets in electronics, pharmaceuticals, and
agrochemicals, as well as high-performance polymers. Miscellaneous uses include its use in
solvents, coating resins, and as pharmaceutical intermediates. Worldwide production capacity
for 1,4-Butanediol is measured in the millions of metric tons/year.
1,4-Butanediol is a precursor to gamma-hydroxybutyric acid (GHB), and is readily converted to GHB
upon its ingestion producing clinical effects identical to GHB. 1,4-Butanediol appears not to have
behavioral effects of its own because its direct CNS administration is without effects. 1,4-
BD's biotransformation to GHB involves enzymes also involved in alcohol's metabolism, and
co-ingestion with ethanol can alter the time course and magnitude of 1,4-Butanediol's toxicity.
GHB was marketed to bodybuilders in the 1980s as a purported aid to muscle building and fat
loss. Because of its euphoric and sexual effects, it became a drug of abuse. Reports of the
drug's toxicity resulted in warnings about health risks. Subsequently, 1,4-Butanediol and GBL,
another precursor to GHB, began to be marketed as a "natural," "nontoxic" dietary
supplement, and as a substitute for GHB for its intoxicating effects.
1,4-Butanediol is used as a liquid and a few milliliters would be a typical recreational dose. There is a
steep dose-effect curve between doses producing desired and excessive effects, and there have
been published reports of adverse reactions to 1,4-Butanediol including fatalities. Signs and
symptoms can include: euphoria, relaxation, reduced inhibition and sedation, progressing to
vomiting, urinary and fecal incontinence, agitation, convulsions, bradycardia, respiratory
depression, coma and death.
Because of 1,4-Butanediol's rapid conversion to GHB, the epidemiology of their use and abuse is
intrinsically linked. Also, forensic samples of blood and other tissues are not analyzed for
GHB's precursors and not routinely even for GHB. These observations, coupled with the fact
that most surveys treat incidences of GHB's, GBL's and 1,4-Butanediol's use as if they were one drug,
makes accurately estimating the incidence, prevalence and societal harm produced specifically
by 1,4-Butanediol impossible at present.
In view of concerns about the diversion of 1,4-Butanediol from the domestic distribution channel and
illicit trade of 1,4-Butanediol, some Member States have chosen to control it under drug control or
equivalent legislation. Furthermore, the European Community and the Member States have
taken additional voluntary measures to prevent its diversion. This includes guidance for
operators to be vigilant when placing this substance onto the international market.
1,4-Butanediol has the capacity to produce a state of dependence, and can produce similar effects as
GHB that is in Schedule II of the 1971 Convention. However, the prevalence and magnitude
of the public health and social problems its use specifically creates is difficult to accurately
estimate. Coupled with the appreciation that 1,4-Butanediol is used as an industrial chemical with
production and trade in the millions of metric tons, controlling it as a psychotropic substance
equivalent to GHB would not likely result in benefits sufficient to justify the burdens such
controls would impose.
1,4-Butanediol (1,4-B, butylene glycol, or BD) is a thick, colourless liquid which is nearly odorless with a distinct bitter taste. 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, 1,4-butanediol is used for the synthesis of ?-butyrolactone (GBL). 1,4-Butanediol (1,4-B, butylene glycol, or BD) is a thick, colourless liquid which is nearly odorless with a distinct bitter taste. 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, 1,4-butanediol is used for the synthesis of γ-butyrolactone (GBL). In humans, it acts as a depressant and a prodrug for GHB where 1ml is equivalent to 1g of GHB. It is used as a recreational intoxicant with effects similar to alcohol. 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.
1,4-BUTANEDIOL is heat and light sensitive. This compound reacts with acid chlorides, acid anhydrides and chloroformates. It also reacts with oxidizing agents and reducing agents. It is incompatible with isocyanates and acids. It is also incompatible with peroxides, perchloric acid, sulfuric acid, hypochlorous acid, nitric acid, caustics, acetaldehyde, nitrogen peroxide and chlorine. (NTP, 1992).
1,4-Butanediol, as well as GBL, will dissolve most types of plastic over time.[4] 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. 1,4-Butanediol is the organic compound with the formula HOCH2CH2CH2CH2OH. This colorless viscous liquid is derived from butane by placement of alcohol groups at each end of the chain. 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, 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.
1,4-Butanediol. It is biodegradable with high melting point and is soluble in water, alcohols, ketones and esters. It reacts with terephthalic acid to produce polybutylene terephthalate (PBT). It also reacts with adipic acid to yield polyesters with biodegradability characteristics. It produces polymers which exhibits greater hydrophobicity, crystallinity, strength, hydrolysis resistance and better low temperature flexibility than those produced from ethylene glycol. Used in polyurethane foams, elastomers and adhesives.
In humans, it acts as a depressant and a prodrug for GHB where 1ml is equivalent to 1g of GHB. It is used as a recreational intoxicant with effects similar to alcohol. 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.
1,4-Butanediol, as well as GBL, will dissolve most types of plastic over time.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.
1.4-Butanediol (BDO) is a high-quality intermediate. BDO and its derivatives are widely used for producing plastics, solvents, electronic chemicals and elastic fibers. Butanediol and its derivatives is used in a broad spectrum of applications in the chemical industry; amongst others in the manufacturing of technical plastics, polyurethanes, solvents, electronic chemicals and elastic fibres.
The hydroxyl function of each end group of the Butanediol reacts with different mono- and bifunctional reagents: for example with dicarboxylic acids to polyesters, with diisocyanates to polyurethanes, or with phosgene to polycarbonates. Additionally BDO is also a building block for the synthesis of polyesterpolyols and polyetherpolyols.
1,4-butanediol (1,4-BD) is a colorless, viscous liquid derived from butane by placement of alcohol groups at each end of its molecular chain and is one of four stable isomers of butanediol.the hydroxyl function of each end group of the Butanediol reacts with different mono- and bifunctional reagents: for example with dicarboxylic acids to polyesters, with diisocyanates to polyurethanes, or with phosgene to polycarbonates. 1.4-Butanediol (BDO) is a high-quality intermediate. BDO and its derivatives are widely used for producing plastics, solvents, electronic chemicals and elastic fibers. Additionally BDO is also a building block for the synthesis of polyesterpolyols and polyetherpolyols. BASF is the most significant producer of 1,4-Butanediol and its derivatives worldwide.
Physical Description
1,4-BUTANEDIOL is an odorless colorless liquid or solid (depending upon temperature). COLOURLESS VISCOUS LIQUID. Colorless, oily liquid. Almost odorless. Solubility: greater than or equal to 100 mg/mL at 73° F (NTP, 1992).Water Solubility: 1000000 mg/L (at 20 °C).
Readily soluble in water, alcohols, ketones, glycol ethers, and glycol ether acetates; less soluble in diethyl ether and esters; not miscible with aliphatic and aromatic hydrocarbons and chlorinated hydrocarbons. Miscible in water, soluble in ethanol and dimethyl sulfoxide; slightly soluble in diethyl ether. Decomposition; When heated to decomposition it emits acrid smoke and fumes. Corrosivity; Noncorrosive. Subjective effects; The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include injury or death.
1,4-Butanediol is the organic compound with the formula HOCH2CH2CH2CH2OH. This colorless viscous liquid is derived from butane by placement of alcohol groups at each end of the chain. 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, 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.
1,4-BÜTANDİOL
1,4-bütandiol Görünümü
Berrak sıvı
1,4-bütandiol Kimyasal Adı
• 1,4-bütandiol (BDO)
1,4-bütandiol Kimyasal Formülü
• C4H10O2
1,4-bütandiol Ambalaj Şekli
1,4-bütandiol Açıklama
• 1,4-bütandiol Su, alkol, keton ve esterlerde çözünür. 1,4-bütandiol Biyobozunurdur ve yüksek kaynama noktasına sahiptir.
1,4-bütandiol Kullanım Alanları
1,4-bütandiol Poliüretan, poliüretan terafitalat, poliester sistemleri ve biyo-plastik uygulamalarında kullanım alanına sahiptir. 1,4-bütandiol Doymuş poliester makroglikollerin üretiminde, dökülebilir elastomer ve kaplama malzemelerinin üretminde ve mikroselülar poliüretan yapımında kullanılablir.
1,4-Bütandiol halk dilinde bilinen, BD , bir organik bileşik ile , formül HOCH 2 CH 2 CH 2 CH 2 OH. Bu, renksiz viskoz bir sıvı . Dört sabit biridir izomerleri arasında bütandiol .
sentez
Endüstriyel olarak sentez , asetilen iki eşdeğeri ile reaksiyona girerek formaldehit oluşturmak üzere 1,4-Bütandiol . Asetilen bazlı Sürecin bu tip Alman kimyager sonra "Reppe kimya" olarak bilinen şeyin açıklayıcı olduğu Walter Reppe . Hidrojenasyon 1,4-Bütandiol 1,4-bütandiol verir. Bu rota BASF ve Ashland / ISP tarafından kullanılır. Aynı zamanda, bir endüstriyel ölçekte üretilir maleik anhidrit içinde Davy işleminin birinci metil maleat esterine dönüştürülür, daha sonra hidrojenlenir. Diğer yollar ile ilgili olan butadien , alil asetat ve süksinik asit .
1,4-Bütandiol için bir biyolojik rota kullanan ticarileştirilmiştir genetik olarak modifiye edilmiş bir organizma . Biyosentezi yoluyla ilerleyen ; 4-hidroksi .
1,4-Bütandiol, bir endüstriyel olarak kullanılan çözücü madde ve bazı tiplerinin imalatında da plastik , elastik lifleri ve poliüretanlar . Olarak organik kimya , 1,4-bütandiol sentezi için kullanılan γ-butirolakton (GBL). Varlığında , fosforik asit ve yüksek sıcaklık, önemli bir çözücü üzere suyunu tetrahidrofuran . Çözünür mevcudiyetinde yaklaşık 200 ° C 'de rutenyum katalizörler , diol maruz dehidrojenasyonu oluşturmak üzere butirolakton .
1,4-bütandiol Dünya üretimi yılda yaklaşık bir milyon metrik ton olduğu iddia edilen ve piyasa fiyatı yaklaşık 2,000 edildi USD ton (2005) başına (1,600 Euro). 2013 yılında tüm dünyada (yaklaşık bir milyon metrik ton ile tutarlı) lbs milyarlarca olduğu iddia edildi.
Hemen hemen yarısı için dehidre edilir , tetrahidrofuran gibi elyaf üretmek için Spandeks . Büyük üreticisidir BASF .
bir ilaç olarak insan sağlığı üzerindeki etkileri ve kullanım
GHB ve örneğin 1,4-bütandiol gibi ön ilaçları içeren ürünlere karşı FDA uyarısı.
1,4-bütandiol de olarak kullanılır eğlence ilaç "Tek Virgül Dört", "Sıvı Fantezi", "Bir dört Bee" veya "Tek Dört 1,4-Bütandiol " olarak bazı kullanıcılar tarafından da bilinir. Bu benzer etkiler yaratır -hidroksibutrat y 1,4-bütandiol metabolik bir ürünü olan (GHB). Diğer ilaçlar ile karıştırıldığında, 1,4-bütandiol kötüye bağımlılığı ve ölümle sonuçlanmıştır.
Farmakokinetik
1,4-Bütandiol dönüştürülür GHB'yle enzimler alkol dehidrogenaz ve aldehit dehidrogenazın ve bu enzimlerin farklı seviyeleri etkileri ve farklılıkları hesaba olabilir yan etkileri , kullanıcılar arasında. Birlikte uygulanması da etanol ve GHB'nin önce ciddi riskler birlikte uygulanmasını teşkil etanol önemli ölçüde etkileşimde bulunacak 1,4-bütandiol ile ve diğer pek çok potansiyel riskleri vardır. Tehlikeli bir ihtimali vardır, böylece alkol metabolize sorumlu aynı enzimler de 1,4-bütandiol metabolize olmasıdır ilaç etkileşimi . Her iki doz aşımı acil hasta etanol belirtileri ile ve 1,4-bütandiol, genellikle, bu alkol zehirlenmesi , ilk ve etanol metabolize olduğu gibi 1,4-bütandiol, sonra daha iyi bir enzim ve bir intoksikasyon saniyelik bir süre görüldüğünde için rekabet edebilir 1,4-bütandiol GHB'ye dönüşür olarak.
1,4-bütandiol metabolik yol, γ-bütirolakton ve γ-hidroksibutirik asit (GHB) .
Farmakodinamik
1,4-bütandiol farmakolojik eylemlerin iki tür var gibi görünüyor. Bu GHB'ye metabolize olduğundan, 1,4-bütandiol ana psikoaktif etkiler; Bununla birlikte, 1,4-bütandiol, bu dönüştürme nedeniyle değil, potansiyel alkol gibi farmakolojik etkilere sahip olabileceğini öne süren bir çalışma yoktur. Çalışma etanol ile birlikte uygulandığında 1,4-butandiol etanol davranışsal etkileri bazılarının potensiyelizasyon yol açtığını bulgusuna dayanmaktadır varılmıştır. Ancak, etanolün etkilerini güçlendirilmesi sadece için rekabet neden olabilir alkol dehidrojenaz ve asetaldehit dehidrojenaz birlikte uygulanan 1,4-bütandiol ile enzim. Paylaşılan metabolik hız-sınırlayıcı adımları ve böylece etanolün bilinen toksik metabolitin de dahil olmak üzere, her iki bileşik için yavaşlamış bir metabolizma ve temizlenmesine yol asetaldehit .
Bir başka çalışmada, 1,4-butandiol, sıçanlarda intraserebroventriküler enjeksiyonu takiben bir etkisi bulduk. Bu 1,4-bütandiol doğal alkol gibi farmakolojik etkilere sahip olduğu hipotezini çelişmektedir.
Gibi GHB , 1,4-bütandiol küçük miktarlarda sadece güvenlidir. Büyük miktarlarda yutulduğunda yüksek dozlarda yan etkileri, mide bulantısı, kusma, baş dönmesi, uyuşma, baş dönmesi, ve potansiyel olarak ölüm bulunmaktadır. Anksiyolitik etkileri azalır ve alkol ile kombinasyon halinde kullanıldığı zaman yan etkileri artmıştır.
yasallık
1,4-bütandiol şu anda olmasa da ABD'de federal olarak planlanan , devletler bir dizi uyuşturucu madde olarak 1,4-bütandiol sınıflandırdı. Bireyler altında 1,4-bütandiol için kovuşturuldu Federal Analog Yasası büyük ölçüde benzer şekilde GHB'nin . 2002 yılında New York'taki bir federal dava 1,4-butandiol bir kabul edilemeyeceği hükmetti analog federal yasalara göre GHB ancak karar daha sonra ikinci gezici tarafından bozuldu. Ancak, Chicago Federal Bölge Mahkemesi 1,4-bütandiol federal yasa altında GHB bir analog olarak kabul edilemez olduğuna karar verdi ve Yargıtay Yedinci Devre Mahkemesi kararı onayladı. Olarak , Birleşik Krallık , 1,4-bütandiol (başka bir GHB ön-madde ile birlikte, Aralık 2009'da planlandı gama-bütirolakton bir şekilde) C sınıfı kontrollü bir madde. Almanya'da, uyuşturucu açıkça yasadışı değil ama bir ilaç olarak kullanılması halinde de yasadışı olarak tedavi edilebilir. Bu bir zamanlama VI olarak kontrol edilir öncü içinde Kanada .
1,4-Bütandiol, formülü HOCH2CH2CH2CH2OH organik bir bileşiktir. Bu renksiz viskoz sıvı, bütan zincirinin her iki ucuna da alkol gruplarının yerleştirilmesi ile elde edilir. 1,4-Bütandiol, endüstride bir çözücü olarak plastikler, elastik lifler ve poliüretanların bazı türlerinin üretiminde kullanılır. Organik kimyada, 1,4-bütandiol γ-butirolakton (GBL) sentezi için kullanılır. Fosforik asit ve yüksek sıcaklık varlığında, tetrahidrofuranı suyunun önemli bir çözücüsüdür.
1,4-Butandiol (1,4-B, bütilen glikol veya BD) kalın, renksiz bir sıvıdır ve neredeyse kokusuzdur, farklı acı bir tada sahiptir. 1,4-Bütandiol , endüstriyel olarak bir çözücü olarak ve bazı plastik, elastik lifler ve poliüretan türlerinin imalatında kullanılır. Organik kimyada, 1,4-butandiol, a-bütirolakton (GBL) sentezi için kullanılır. İnsanlarda, 1 ml'lik bir gram GHB'ye denk gelen GHB için bir depresan ve bir ön ilaç olarak görev yapar. Alkole benzer etkilere sahip dinlendirici bir zehirlenme maddesi olarak kullanılır.
1,4-Bütandiol , dioller olarak adlandırılan alkollü bileşiklerin bir alt sınıfı olarak sınıflandırılır. Dioller, yapılarında iki alkol (OH-) ikamesine sahip oldukları için isimlendirilir. 1,4-Butandiol, bu zincirin her bir terminal karbonuna bağlı alkol grubuna sahip dört karbon grubundan bir bütan zincirinden oluşur. 1,4-Bütandiol , R1 ve R4'de bulunan bu alkol ikamelerinin adını alır.
1,4-Bütandiol ve GBL, çoğu plastik türünü zamanla çözer. Bu nedenle, sadece bir cam kap, standart jelatin kapsülleri (vejetaryen değil) veya yüksek dozda jelatin kapsülleri kullanarak ilacın taşınması ve depolanması önerilir. (aynı zamanda # 2 geri dönüştürülmüş plastik olarak da bilinir). Bir şişede kullanılan plastik türünü kontrol etmek için, üçgen şeklindeki geri dönüşüm etiketinde bir numara için alt kısmına bakabilirsiniz.
1,4-bütandiol (BDO), yüksek kaliteli bir ara maddedir. 1,4-bütandiol ve türevleri plastik, solvent, elektronik kimyasallar ve elastik liflerin üretimi için yaygın olarak kullanılmaktadır. Butandiol ve türevleri kimya endüstrisinde geniş bir uygulama yelpazesinde kullanılır; diğerleri arasında teknik plastik, poliüretanlar, solventler, elektronik kimyasallar ve elastik liflerin imalatında. Butandiol'ün her bir uç grubunun hidroksil fonksiyonu, farklı mono- ve iki fonksiyonlu ayıraçlarla reaksiyona girer: örneğin dikarboksilik asitler ile polyesterler, diizosiyanatlar ile poliüretanlar arasında veya fosgen ile polikarbonatlar arasında. Ayrıca BDO, polyesterpolyollerin ve polieterpolyollerin sentezi için bir yapı taşıdır.
Fiziksel tanım
1,4-bütandiol, kokusuz bir renksiz sıvı veya katıdır (sıcaklığa bağlı olarak). Renksiz Viskoz SIVI. renksiz, yağlı sıvı. Neredeyse kokusuz. Çözünürlük: 73 ° F'de 100 mg / mL'ye eşit veya daha yüksek (NTP, 1992). Suda Çözünürlüğü: 1000000 mg / L (20 ° C'de). Suda kolaylıkla çözünür, alkoller, ketonlar, glikol eterleri ve glikol eter asetatları; dietil eter ve esterlerde daha az çözünür; alifatik ve aromatik hidrokarbonlar ve klorlu hidrokarbonlarla karışmaz. Suda karışabilir, etanol ve dimetil sülfokside çözünebilir; dietil eter içinde az çözünür. Ayrışma; Parçalanmaya kadar ısıtıldığında sersemli bir duman ve duman yayar. Aşındırıcılık, Paslanmaz.
Subjektif etkiler
1,4-Butanediol Özellik Adı: Özellik Değer Referansı
1,4-Bütandiolün Molekül Ağırlığı: 90.12 g / mol
1,4-Bütandiolün XLogP3: -0.8 XLogP3 3.0
1,4-Bütandiol'ün Hidrojen Bağ Donör Sayısı: 2
1,4-Bütandiol'ün Hidrojen Bağ Alıcı Sayısı: 2
1,4-Bütandiolün Dönebilir Bağ Sayısı: 3
Tam Kütle 1,4-Bütandiol: 90.06808 g / mol PubChem 2.1
1,4-Bütandiolün Monoizotop Kütlesi: 90.06808 g / mol PubChem 2.1
1,4-Bütandiolün Topolojik Polar Yüzey Alanı: 40.5 Ų Cactvs 3.4.6.11
1,4-Bütandiolün Ağır Atom Sayısı: 6 PubChem
1,4-Bütandiolün Resmi Yükü: 0 PubChem
1,4-Bütandiolün karmaşıklığı: 17.5
1,4-Bütandiolün İzotop Atom Sayısı: 0
1,4-Bütandiolün Tanımlı Atom Stereo Merkezi Sayı: 0
Tanımsız Atom Stereocenter 1,4-Bütandiol Sayısı: 0
1,4-Bütandiolün Tanımlı Bond Stereo Merkezi Sayı: 0
Tanımsız Bond Stereocenter 1,4-Bütandiol Sayısı: 0
1,4-Bütandiolün Kovalent-Bağlı Birim Sayısı: 1
Bileşik 1,4-Bütandiolün Kanonikleştirildi: Evet
1,4-Butandiolün Deneysel Özellikleri:
3.2.1 1,4-Bütandiolün Fiziksel Açıklaması: HelpNew Window
1,4-bütandiol, kokusuz renksiz sıvı veya katı (sıcaklığa bağlı olarak) olarak görünür. (USCG, 1999)
Butane-1,4-diol
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Butane-1,4-diol
Image illustrative de l'article Butane-1,4-diol
Image illustrative de l'article Butane-1,4-diol
Identification
Nom UICPA Butane-1,4-diol
Synonymes
1,4-butanediol
No CAS 110-63-4
No ECHA 100.003.443
No CE 203-786-5
SMILES
[Afficher]
InChI
[Afficher]
Apparence Liquide visqueux incolore
Propriétés chimiques
Formule brute C4H10O2 [Isomères]
Masse molaire2 90,121 ± 0,0045 g/mol
C 53,31 %, H 11,18 %, O 35,51 %,
Moment dipolaire 2,5 D 1
Diamètre moléculaire 0,574 nm 1
Propriétés physiques
T° fusion 20 °C3
T° ébullition 230 °C3
Solubilité miscible à l'eau3
Paramètre de solubilité δ 24,8 MPa1/2 (25 °C)4
Masse volumique 1,02 g·cm-3 (20 °C)3
T° d'auto-inflammation 370 °C3
Point d'éclair 130 °C (coupelle fermée)3
Limites d'explosivité dans l'air 1,8 Vol.-%, 67 g/m3
15,7 Vol.-%, 585 g/m33
Pression de vapeur saturante < 0,1 mbar (20 °C3
Thermochimie
Cp
[+]
Propriétés optiques
Indice de réfraction {\displaystyle {\textit {n}}_{D}^{25}}{\textit {n}}_{{D}}^{{25}} 1,4443 1
Précautions
NFPA 704
Symbole NFPA 704.
110
Directive 67/548/EEC
Nocif
Xn
[+]
Phrases R : 22,
Écotoxicologie
DL50 2 062 mg·kg-1 (souris, oral)6
1 650 mg·kg-1 (souris, i.p.)7
LogP -0,838
Composés apparentés
Isomère(s) butane-1,2-diol
butane-1,3-diol
butane-2,3-diol
Unités du SI et CNTP, sauf indication contraire.
modifier Consultez la documentation du modèle
Le butane-1,4-diol est un composé chimique de la famille des diols, constitué d'une chaine de butane portant un groupe hydroxyle à chaque extrémité. C'est l'un des quatre isomères stables du butanediol.
Il se présente sous la forme d'un liquide visqueux et incolore.
synthese
Le butane-1,4-diol est obtenu industriellement par hydrogénation du but-2-yne-1,4-diol, lui-même obtenu par réaction de l'acétylène sur deux équivalents de méthanal. Ce type de processus basé sur l'acétylène est une illustration de ce qui est appelé « chimie de l'acétylène » ou « chimie de Reppe », du nom du chimiste allemand Walter Reppe qui en est l'un des fondateurs.
Le butane-1,4-diol peut aussi être produit industriellement par hydrogénation en phase vapeur des esters et des anhydres des acides maléique et succinique.
Ce produit peut être aujourd'hui biosourcé : Genomatica (une compagnie de génomatique basée à San Diego) a modifié génétiquement E. coli pour qu'elle métabolise le sucre en butane-1,4-diol9.
Utilisation
Le butane-1,4-diol est utilisé industriellement comme solvant et dans la fabrication de plastiques, fibres élastiques et polyuréthanes. En chimie organique, le butane-1,4-diol permet la synthèse de la γ-butyrolactone (GBL) (réaction à 200 °C en présence de ruthénium comme catalyseur10). En présence de l'acide phosphorique à haute température, il se déshydrate en formant un solvant très utilisé, le tétrahydrofurane (THF)11.
La production mondiale annuelle de butane-1,4-diol est évaluée à un million de tonnes, au prix d'environ deux mille dollars la tonne en 2005. Environ la moitié est déshydratée en THF pour produire des fibres de type élasthanne12. Le plus gros producteur est le groupe chimique allemand BASF13.
Usage détourné
Le butane-1,4-diol est aussi utilisé comme drogue récréative, connu sous le nom de « One Comma Four », « One Four Bee » ou « One Four B-D-O ». Il a des effets similaires au gamma-hydroxybutyrate (GHB), produit métabolique du butane-1,4-diol14,15
Pharmacocinétique
Le butane-1,4-diol est converti en GHB via GHBAL, par les enzymes alcool déshydrogénase et aldéhyde déshydrogénase, avec des différences de niveau selon les individus, provoquant ainsi des effets différents selon les utilisateurs16. Comme ces enzymes sont aussi responsables du métabolisme de l'alcool, il y a de grands risques d'interaction entre les deux processus16,17. Les patients aux urgences faisant une overdose d'alcool et de butane-1,4-diol présentent souvent au départ les symptômes d'une intoxication à l'éthanol, puis quand l'éthanol est métabolisé, le métabolisme du butane-1,4-diol est capable de concurrencer l'utilisation des enzymes et une seconde période d'intoxication se déroule quand le butane-1,4-diol est converti en GHB16.
Pharmacodynamie
Le butane-1,4-diol semble avoir deux types d'actions pharmacologiques. Les principaux effet psychoactifs du butane-1,4-diol sont dus à sa transformation en GHB. Cependant, on soupçonne le butane-1,4-diol d'avoir des effets pharmacologiques de même nature que ceux de l'alcool et qui ne sont pas dus à cette conversion17.
Législation
Aux États-Unis, le butane-1,4-diol n'est pas surveillé fédéralement, mais un certain nombre d'États l'ont classé comme substance à contrôler. Son interdiction au niveau fédéral semble peu probable, du fait du grand nombre de ses applications industrielles légitimes.
Contamination du jeu Bindeez
Un jeu australien, appelé Bindeez (en) (Aqua Dots en Amérique du Nord) constitué de petites billes de plastique coloré contenant normalement du pentane-1,5-diol a été rappelé en novembre 2007 par son fabricant. Il s'est en effet avéré que le fabricant chinois, Wangqi Product Factory, avait substitué sans autorisation le pentane-1,5-diol, physiologiquement sans risque, par du butane-1,4-diol18 vraisemblablement pour des raisons de coût (ChemNet China évalue le prix du butane-1,4-diol entre 1 350 et 2 800 $ la tonne, contre environ 9 700 $ la tonne pour le pentane-1,5-diol19).
