1,4-BUTANEDIOL (1,4-btandiol)

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-BUTANEDOL

1,4-BUTANEDIOL; 1,4-BÜTANEDIOL; 1,4-BUTANEDiOL; 1 4-BUTANEDIOL; 1,4 BUTANEDIOL; 1,4-BUTANE DIOL; 1,4-BUTANEDIOLE; 1,4-BUTANEDOLE; 1,4-BÜTANEDOLE; 1,4-BÜTANDOL; 1,4-BÜTAN DOL; 1,4 – BÜTANDOL; 1,4-BÜTANDOLE; 1,4 BÜTANDOL; 1,4-BÜTAN DOLE; 1 4 BÜTANDOL; 1,4-butanedol; 1,4-bütanedol; 1,4-butanediol; 1 4-butanedol; 1,4 butanedol; 1,4-butane dol; 1,4-butanedole; 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-Butanedol; 1,4-Bütanedol; 1,4-Butanediol; 1 4-Butanedol; 1,4 Butanedol; 1,4-Butane Dol; 1,4-Butanedole; 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; BÜTANDYOL; BUTANDYOLE; 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

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

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 Å² 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-BÜTANDOL

1,4-bütandiol Görünümü

Berrak sv

1,4-bütandiol Kimyasal Ad

• 1,4-bütandiol (BDO)

1,4-bütandiol Kimyasal Formülü

• C4H10O2

1,4-bütandiol Ambalaj ekli

1,4-bütandiol Açklama

• 1,4-bütandiol Su, alkol, keton ve esterlerde çözünür. 1,4-bütandiol Biyobozunurdur ve yüksek kaynama noktasna sahiptir.

1,4-bütandiol Kullanm Alanlar

1,4-bütandiol Poliüretan, poliüretan terafitalat, poliester sistemleri ve biyo-plastik uygulamalarnda kullanm alanna sahiptir. 1,4-bütandiol Doymu poliester makroglikollerin üretiminde, dökülebilir elastomer ve kaplama malzemelerinin üretminde ve mikroselülar poliüretan yapmnda kullanlablir.

1,4-Bütandiol halk dilinde bilinen, BD , bir organik bileik ile , formül HOCH 2 CH 2 CH 2 CH 2 OH. Bu, renksiz viskoz bir sv . Dört sabit biridir izomerleri arasnda bütandiol .

sentez

Endüstriyel olarak sentez , asetilen iki edeeri ile reaksiyona girerek formaldehit oluturmak üzere 1,4-Bütandiol . Asetilen bazl Sürecin bu tip Alman kimyager sonra “Reppe kimya” olarak bilinen eyin açklayc olduu Walter Reppe . Hidrojenasyon 1,4-Bütandiol 1,4-bütandiol verir. Bu rota BASF ve Ashland / ISP tarafndan kullanlr. Ayn zamanda, bir endüstriyel ölçekte üretilir maleik anhidrit içinde Davy ileminin birinci metil maleat esterine dönütürülür, daha sonra hidrojenlenir. Dier yollar ile ilgili olan butadien , alil asetat ve süksinik asit .

1,4-Bütandiol için bir biyolojik rota kullanan ticariletirilmitir genetik olarak modifiye edilmi bir organizma . Biyosentezi yoluyla ilerleyen ; 4-hidroksi .

1,4-Bütandiol, bir endüstriyel olarak kullanlan çözücü madde ve baz tiplerinin imalatnda da plastik , elastik lifleri ve poliüretanlar . Olarak organik kimya , 1,4-bütandiol sentezi için kullanlan γ-butirolakton (GBL). Varlnda , fosforik asit ve yüksek scaklk, önemli bir çözücü üzere suyunu tetrahidrofuran . Çözünür mevcudiyetinde yaklak 200 ° C ‘de rutenyum katalizörler , diol maruz dehidrojenasyonu oluturmak üzere butirolakton .

1,4-bütandiol Dünya üretimi ylda yaklak bir milyon metrik ton olduu iddia edilen ve piyasa fiyat yaklak 2,000 edildi USD ton (2005) bana (1,600 Euro). 2013 ylnda tüm dünyada (yaklak bir milyon metrik ton ile tutarl) lbs milyarlarca olduu iddia edildi.

Hemen hemen yars için dehidre edilir , tetrahidrofuran gibi elyaf üretmek için Spandeks . Büyük üreticisidir BASF .

bir ilaç olarak insan sal üzerindeki etkileri ve kullanm

GHB ve örnein 1,4-bütandiol gibi ön ilaçlar içeren ürünlere kar FDA uyars.

1,4-bütandiol de olarak kullanlr elence ilaç “Tek Virgül Dört”, “Sv Fantezi”, “Bir dört Bee” veya “Tek Dört 1,4-Bütandiol ” olarak baz kullanclar tarafndan da bilinir. Bu benzer etkiler yaratr -hidroksibutrat y 1,4-bütandiol metabolik bir ürünü olan (GHB). Dier ilaçlar ile kartrldnda, 1,4-bütandiol kötüye bamll ve ölümle sonuçlanmtr.

Farmakokinetik

1,4-Bütandiol dönütürülür GHB’yle enzimler alkol dehidrogenaz ve aldehit dehidrogenazn ve bu enzimlerin farkl seviyeleri etkileri ve farkllklar hesaba olabilir yan etkileri , kullanclar arasnda. Birlikte uygulanmas da etanol ve GHB’nin önce ciddi riskler birlikte uygulanmasn tekil etanol önemli ölçüde etkileimde bulunacak 1,4-bütandiol ile ve dier pek çok potansiyel riskleri vardr. Tehlikeli bir ihtimali vardr, böylece alkol metabolize sorumlu ayn enzimler de 1,4-bütandiol metabolize olmasdr ilaç etkileimi . Her iki doz am acil hasta etanol belirtileri ile ve 1,4-bütandiol, genellikle, bu alkol zehirlenmesi , ilk ve etanol metabolize olduu gibi 1,4-bütandiol, sonra daha iyi bir enzim ve bir intoksikasyon saniyelik bir süre görüldüünde için rekabet edebilir 1,4-bütandiol GHB’ye dönüür 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 olduundan, 1,4-bütandiol ana psikoaktif etkiler; Bununla birlikte, 1,4-bütandiol, bu dönütürme nedeniyle deil, potansiyel alkol gibi farmakolojik etkilere sahip olabileceini öne süren bir çalma yoktur. Çalma etanol ile birlikte uygulandnda 1,4-butandiol etanol davransal etkileri bazlarnn potensiyelizasyon yol açtn bulgusuna dayanmaktadr varlmtr. Ancak, etanolün etkilerini güçlendirilmesi sadece için rekabet neden olabilir alkol dehidrojenaz ve asetaldehit dehidrojenaz birlikte uygulanan 1,4-bütandiol ile enzim. Paylalan metabolik hz-snrlayc admlar ve böylece etanolün bilinen toksik metabolitin de dahil olmak üzere, her iki bileik için yavalam bir metabolizma ve temizlenmesine yol asetaldehit .

Bir baka çalmada, 1,4-butandiol, sçanlarda intraserebroventriküler enjeksiyonu takiben bir etkisi bulduk. Bu 1,4-bütandiol doal alkol gibi farmakolojik etkilere sahip olduu hipotezini çelimektedir.

Gibi GHB , 1,4-bütandiol küçük miktarlarda sadece güvenlidir. Büyük miktarlarda yutulduunda yüksek dozlarda yan etkileri, mide bulants, kusma, ba dönmesi, uyuma, ba dönmesi, ve potansiyel olarak ölüm bulunmaktadr. Anksiyolitik etkileri azalr ve alkol ile kombinasyon halinde kullanld zaman yan etkileri artmtr.

yasallk

1,4-bütandiol u anda olmasa da ABD’de federal olarak planlanan , devletler bir dizi uyuturucu madde olarak 1,4-bütandiol snflandrd. Bireyler altnda 1,4-bütandiol için kovuturuldu Federal Analog Yasas büyük ölçüde benzer ekilde GHB’nin . 2002 ylnda New York’taki bir federal dava 1,4-butandiol bir kabul edilemeyecei hükmetti analog federal yasalara göre GHB ancak karar daha sonra ikinci gezici tarafndan bozuldu. Ancak, Chicago Federal Bölge Mahkemesi 1,4-bütandiol federal yasa altnda GHB bir analog olarak kabul edilemez olduuna karar verdi ve Yargtay Yedinci Devre Mahkemesi karar onaylad. Olarak , Birleik Krallk , 1,4-bütandiol (baka bir GHB ön-madde ile birlikte, Aralk 2009’da planland gama-bütirolakton bir ekilde) C snf kontrollü bir madde. Almanya’da, uyuturucu açkça yasad deil ama bir ilaç olarak kullanlmas halinde de yasad olarak tedavi edilebilir. Bu bir zamanlama VI olarak kontrol edilir öncü içinde Kanada .

1,4-Bütandiol, formülü HOCH2CH2CH2CH2OH organik bir bileiktir. Bu renksiz viskoz sv, bütan zincirinin her iki ucuna da alkol gruplarnn yerletirilmesi ile elde edilir. 1,4-Bütandiol, endüstride bir çözücü olarak plastikler, elastik lifler ve poliüretanlarn baz türlerinin üretiminde kullanlr. Organik kimyada, 1,4-bütandiol γ-butirolakton (GBL) sentezi için kullanlr. Fosforik asit ve yüksek scaklk varlnda, tetrahidrofuran suyunun önemli bir çözücüsüdür.

1,4-Butandiol (1,4-B, bütilen glikol veya BD) kaln, renksiz bir svdr ve neredeyse kokusuzdur, farkl ac bir tada sahiptir. 1,4-Bütandiol , endüstriyel olarak bir çözücü olarak ve baz plastik, elastik lifler ve poliüretan türlerinin imalatnda kullanlr. Organik kimyada, 1,4-butandiol, a-bütirolakton (GBL) sentezi için kullanlr. nsanlarda, 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 kullanlr.

1,4-Bütandiol , dioller olarak adlandrlan alkollü bileiklerin bir alt snf olarak snflandrlr. Dioller, yaplarnda iki alkol (OH-) ikamesine sahip olduklar için isimlendirilir. 1,4-Butandiol, bu zincirin her bir terminal karbonuna bal alkol grubuna sahip dört karbon grubundan bir bütan zincirinden oluur. 1,4-Bütandiol , R1 ve R4’de bulunan bu alkol ikamelerinin adn alr.

1,4-Bütandiol ve GBL, çou plastik türünü zamanla çözer. Bu nedenle, sadece bir cam kap, standart jelatin kapsülleri (vejetaryen deil) veya yüksek dozda jelatin kapsülleri kullanarak ilacn tanmas ve depolanmas önerilir. (ayn zamanda # 2 geri dönütürülmü plastik olarak da bilinir). Bir iede kullanlan plastik türünü kontrol etmek için, üçgen eklindeki geri dönüüm etiketinde bir numara için alt ksmna bakabilirsiniz.

1,4-bütandiol (BDO), yüksek kaliteli bir ara maddedir. 1,4-bütandiol ve türevleri plastik, solvent, elektronik kimyasallar ve elastik liflerin üretimi için yaygn olarak kullanlmaktadr. Butandiol ve türevleri kimya endüstrisinde geni bir uygulama yelpazesinde kullanlr; dierleri arasnda teknik plastik, poliüretanlar, solventler, elektronik kimyasallar ve elastik liflerin imalatnda. Butandiol’ün her bir uç grubunun hidroksil fonksiyonu, farkl mono- ve iki fonksiyonlu ayraçlarla reaksiyona girer: örnein dikarboksilik asitler ile polyesterler, diizosiyanatlar ile poliüretanlar arasnda veya fosgen ile polikarbonatlar arasnda. Ayrca BDO, polyesterpolyollerin ve polieterpolyollerin sentezi için bir yap tadr.

Fiziksel tanm

1,4-bütandiol, kokusuz bir renksiz sv veya katdr (scakla bal olarak). Renksiz Viskoz SIVI. renksiz, yal sv. Neredeyse kokusuz. Çözünürlük: 73 ° F’de 100 mg / mL’ye eit veya daha yüksek (NTP, 1992). Suda Çözünürlüü: 1000000 mg / L (20 ° C’de). Suda kolaylkla çözünür, alkoller, ketonlar, glikol eterleri ve glikol eter asetatlar; dietil eter ve esterlerde daha az çözünür; alifatik ve aromatik hidrokarbonlar ve klorlu hidrokarbonlarla karmaz. Suda karabilir, etanol ve dimetil sülfokside çözünebilir; dietil eter içinde az çözünür. Ayrma; Parçalanmaya kadar stldnda sersemli bir duman ve duman yayar. Andrclk, Paslanmaz.

Subjektif etkiler

1,4-Butanediol Özellik Ad: Özellik Deer Referans

1,4-Bütandiolün Molekül Arl: 90.12 g / mol

1,4-Bütandiolün XLogP3: -0.8 XLogP3 3.0

1,4-Bütandiol’ün Hidrojen Ba Donör Says: 2

1,4-Bütandiol’ün Hidrojen Ba Alc Says: 2

1,4-Bütandiolün Dönebilir Ba Says: 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 Alan: 40.5 Å² Cactvs 3.4.6.11

1,4-Bütandiolün Ar Atom Says: 6 PubChem

1,4-Bütandiolün Resmi Yükü: 0 PubChem

1,4-Bütandiolün karmakl: 17.5

1,4-Bütandiolün zotop Atom Says: 0

1,4-Bütandiolün Tanml Atom Stereo Merkezi Say: 0

Tanmsz Atom Stereocenter 1,4-Bütandiol Says: 0

1,4-Bütandiolün Tanml Bond Stereo Merkezi Say: 0

Tanmsz Bond Stereocenter 1,4-Bütandiol Says: 0

1,4-Bütandiolün Kovalent-Bal Birim Says: 1

Bileik 1,4-Bütandiolün Kanonikletirildi: Evet

1,4-Butandiolün Deneysel Özellikleri:

3.2.1 1,4-Bütandiolün Fiziksel Açklamas: HelpNew Window

1,4-bütandiol, kokusuz renksiz sv veya kat (scakla bal 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

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

[+]

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

[+]

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).

1,4-BUTANEDIOL (1,4-btandiol)

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1,4-BUTANEDIOL (1,4-btandiol)

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