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m Chembox: rm/replace deprecated params. Fix unknown parameters (via AWB script)
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| CASNo = 584-03-2
| CASNo = 584-03-2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| EC-number = 209-527-2
| EC_number = 209-527-2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
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| Density = 1.0023 g/cm<sup>3</sup> (20 °C)
| Density = 1.0023 g/cm<sup>3</sup> (20 °C)
| MeltingPtC = −50
| MeltingPtC = −50
| Melting_ref = <ref group="note">The value of −50&nbsp;°C for the melting point is taken from ''Ullmann's Encyclopedia of Industrial Chemistry'' and used by the [[Hazardous Substances Data Bank]] and the OECD [[Screening Information Dataset]]. Other reported values of the melting point range from −114&nbsp;°C to −30&nbsp;°C.</ref>
| MeltingPt_ref = <ref group="note">The value of −50&nbsp;°C for the melting point is taken from ''Ullmann's Encyclopedia of Industrial Chemistry'' and used by the [[Hazardous Substances Data Bank]] and the OECD [[Screening Information Dataset]]. Other reported values of the melting point range from −114&nbsp;°C to −30&nbsp;°C.</ref>
| BoilingPtC = 195 to 196.9
| BoilingPtC = 195 to 196.9
| Boiling_notes = (96.5 °C at 10 mmHg)
| BoilingPt_notes = (96.5 °C at 10 mmHg)
| Solubility = miscible
| Solubility = miscible
| SolubleOther = soluble in [[ethanol]], [[acetone]]; sparingly soluble in [[ester]]s and [[ether]]s; insoluble in [[hydrocarbon]]s
| SolubleOther = soluble in [[ethanol]], [[acetone]]; sparingly soluble in [[ester]]s and [[ether]]s; insoluble in [[hydrocarbon]]s
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|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| Reference = <ref name="ICSC">{{ICSC-ref|03|95|name=1,2-Butanediol|date=March 1996}}.</ref>
| Reference = <ref name="ICSC">{{ICSC-ref|03|95|name=1,2-Butanediol|date=March 1996}}.</ref>
| ExternalMSDS = [http://www.inchem.org/documents/icsc/icsc/eics0395.htm ICSC 0395]
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0395.htm ICSC 0395]
| EUIndex = not listed
| FlashPtC = 90
| FlashPtC = 90
}}
}}
|Section8={{Chembox Related
|Section8={{Chembox Related
| OtherFunctn = [[1,3-Butanediol]]<br/>[[1,4-Butanediol]]<br/>[[2,3-Butanediol]]
| OtherFunction = [[1,3-Butanediol]]<br/>[[1,4-Butanediol]]<br/>[[2,3-Butanediol]]
| Function = [[butanediol]]s
| OtherFunction_label = [[butanediol]]s
| OtherCpds = [[Ethylene glycol]]<br/>[[Propylene glycol]]<br/>[[2-Hydroxybutyraldehyde]]<br/>[[2-Hydroxybutyric acid]]<br/>[[α-Ketobutyric acid]]
| OtherCompounds = [[Ethylene glycol]]<br/>[[Propylene glycol]]<br/>[[2-Hydroxybutyraldehyde]]<br/>[[2-Hydroxybutyric acid]]<br/>[[α-Ketobutyric acid]]
}}
}}
}}
}}

Revision as of 01:38, 15 July 2015

1,2-Butanediol
Molecular forula of 1,2-Butanediol
Butanediol molecule
Names
IUPAC name
Butane-1,2-diol
Other names
1,2-Dihydroxybutane
α-Butylene glycol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.663 Edit this at Wikidata
EC Number
  • 209-527-2
RTECS number
  • EK0380000
UNII
  • InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 checkY
    Key: BMRWNKZVCUKKSR-UHFFFAOYSA-N checkY
  • InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3
    Key: BMRWNKZVCUKKSR-UHFFFAOYAV
  • OCC(O)CC
  • CCC(CO)O
Properties
C4H10O2
Molar mass 90.121 g/mol
Density 1.0023 g/cm3 (20 °C)
Melting point −50 °C (−58 °F; 223 K)[note 1]
Boiling point 195 to 196.9 °C (383.0 to 386.4 °F; 468.1 to 470.0 K) (96.5 °C at 10 mmHg)
miscible
Solubility soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons
1.4378 (20 °C)
Viscosity 7.3 mPa s (20 °C)
Thermochemistry
−532.8 kJ/mol [4]
−2479 kJ/mol
Hazards
Flash point 90 °C (194 °F; 363 K)
Safety data sheet (SDS) ICSC 0395
Related compounds
Related butanediols
 1,3-Butanediol
1,4-Butanediol
2,3-Butanediol
Related compounds
 Ethylene glycol
Propylene glycol
2-Hydroxybutyraldehyde
2-Hydroxybutyric acid
α-Ketobutyric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1,2-Butanediol is a vic-diol (glycol) first described by Charles-Adolphe Wurtz in 1859.[6] It is produced industrially as a byproduct of the production of 1,4-butanediol from butadiene,[7] and is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[8][note 2] It is used to produce polyester resins and plasticizers,[3][7] and is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to many amino acids.[9]

Notes

  1. ^ The value of −50 °C for the melting point is taken from Ullmann's Encyclopedia of Industrial Chemistry and used by the Hazardous Substances Data Bank and the OECD Screening Information Dataset. Other reported values of the melting point range from −114 °C to −30 °C.
  2. ^ The catalytic hydrocracking of starches and sugars has been successfully commercialized by S2G Biochem Inc. in partnership with International Polyol Chemical, Inc., as of 2007. http://www.s2gbiochem.com/technology.html

References

  1. ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-190. ISBN 0-8493-0462-8..
  2. ^ Ullmann's Encyclopedia of Industrial Chemistry. Vol. A1. Weinheim: Wiley-VCH. p. VA4 461. ISBN 978-3527306732..
  3. ^ a b 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
  4. ^ Moureu, H.; Dode, M. (1937), "Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues", Bull. Soc. Chim. Fr., 4: 637–47.
  5. ^ 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.
  6. ^ Wurtz, A. (1859), Ann. Chim. Phys., 55: 400{{citation}}: CS1 maint: untitled periodical (link).
  7. ^ a b Polyester containing impure 1,2-butanediol, 1986 {{citation}}: Unknown parameter |assignee= ignored (help); Unknown parameter |country-code= ignored (help); Unknown parameter |inventor1-first= ignored (help); Unknown parameter |inventor1-last= ignored (help); Unknown parameter |inventor2-first= ignored (help); Unknown parameter |inventor2-last= ignored (help); Unknown parameter |patent-number= ignored (help).
  8. ^ Recovery of ethylene glycol from butanediol isomers by azeotropic distillation, 1990 {{citation}}: Unknown parameter |country-code= ignored (help); Unknown parameter |inventor-first= ignored (help); Unknown parameter |inventor-last= ignored (help); Unknown parameter |patent-number= ignored (help). Separation of propylene glycol from 1,2-butanediol by azeotropic distillation, 1995 {{citation}}: Unknown parameter |country-code= ignored (help); Unknown parameter |inventor-first= ignored (help); Unknown parameter |inventor-last= ignored (help); Unknown parameter |patent-number= ignored (help).
  9. ^ Process for preparing α-ketobutyric acid, 1992 {{citation}}: Unknown parameter |assignee= ignored (help); Unknown parameter |country-code= ignored (help); Unknown parameter |inventor1-first= ignored (help); Unknown parameter |inventor1-last= ignored (help); Unknown parameter |inventor2-first= ignored (help); Unknown parameter |inventor2-last= ignored (help); Unknown parameter |inventor3-first= ignored (help); Unknown parameter |inventor3-last= ignored (help); Unknown parameter |inventor4-first= ignored (help); Unknown parameter |inventor4-last= ignored (help); Unknown parameter |patent-number= ignored (help).
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