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1,4-butanediol

1,4-Butanediol
1,4-butanediol.svg
14bd3d.png
Names
IUPAC name
Butane-1,4-diol
Other names
Tetramethylene glycol
Identifiers
110-63-4 YesY
3D model (Jmol) Interactive image
Interactive image
ChEMBL ChEMBL171623 YesY
ChemSpider 13835209 YesY
DrugBank DB01955 YesY
ECHA InfoCard 100.003.443
EC Number 203-786-5
RTECS number EK0525000
UNII 7XOO2LE6G3 YesY
Properties
C4H10O2
Molar mass 90.12 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)
Miscible
Solubility in ethanol Soluble
-61.5·10−6 cm3/mol
1.4460 (20 °C)
Hazards
GHS pictograms Acute Tox. (oral) 4
GHS signal word WARNING
H302
P264, P270, P301+312, P330, P501
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 121 °C (250 °F; 394 K)(open cup)
350 °C (662 °F; 623 K)
Related compounds
Related butanediols
1,2-Butanediol
1,3-Butanediol
2,3-Butanediol
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).
YesY  (what is YesYN ?)
Infobox references

1,4-Butanediol, colloquially known as BD, 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. It is one of many stable isomers of butanediol.

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. This route is used by BASF and Ashland/ISP.

LyondellBasell manufactures 1,4-butanediol in a multi-step process without the use of acetylene. First, propylene oxide is converted to allyl alcohol. The allyl alcohol is then hydroformylated to 4-hydroxybutyraldehyde. Hydrogenation of this aldehyde yields 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.

A biological route to BDO has been commerciallized that uses a genetically modified organism. The biosynthesis proceeds via 4-hydroxybutyrate.


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