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==Preparation==
==Preparation==
It is produced industrially by [[hydration]] of the [[1,2-Epoxybutane|1,2-expoxybutane]].<ref>{{Ullmann | title= Butanediols, Butenediol, and Butynediol|
It is produced industrially by [[hydration]] of the [[1,2-Epoxybutane|1,2-expoxybutane]].<ref name=Ullmann>{{Ullmann | title= Butanediols, Butenediol, and Butynediol|Heinz Gräfje et al.|year=2005|doi=10.1002/14356007.a04_455}}</ref><ref name="SIDS">{{SIDS-ref| id=584032 |name=1,2-Butanediol|date=February 1995}}.</ref>
Heinz Gräfje et al.|year=2005|doi=10.1002/14356007.a04_455}}</ref><ref name="SIDS">{{SIDS-ref| id=584032 |name=1,2-Butanediol|date=February 1995}}.</ref>


1,2-Butanediol is a byproduct of the production of [[1,4-butanediol]] from [[butadiene]],<ref name="US4596886">{{citation | inventor1-last = Hasegawa | inventor1-first = Ryuichi | inventor2-last = Hayashi | inventor2-first = Kohji | assignee = Mitsubishi Monsanto Chemical Company | title = Polyester containing impure 1,2-butanediol | country-code = US | patent-number = 4596886 | year = 1986}}.</ref> It is also a byproduct of the catalytic hydrocracking of starches and sugars such as [[sorbitol]] to [[ethylene glycol]] and [[propylene glycol]].<ref>{{citation | inventor-last = Berg | inventor-first = Lloyd | title = Recovery of ethylene glycol from butanediol isomers by azeotropic distillation | country-code = US | patent-number = 4966658 | year = 1990}}. {{citation | inventor-last = Berg | inventor-first = Lloyd | title = Separation of propylene glycol from 1,2-butanediol by azeotropic distillation | country-code = US | patent-number = 5423955 | year = 1995}}.</ref>
1,2-Butanediol is a byproduct of the production of [[1,4-butanediol]] from [[butadiene]],<ref name="US4596886">{{citation | inventor1-last = Hasegawa | inventor1-first = Ryuichi | inventor2-last = Hayashi | inventor2-first = Kohji | assignee = Mitsubishi Monsanto Chemical Company | title = Polyester containing impure 1,2-butanediol | country-code = US | patent-number = 4596886 | year = 1986}}.</ref> It is also a byproduct of the catalytic hydrocracking of starches and sugars such as [[sorbitol]] to [[ethylene glycol]] and [[propylene glycol]].<ref>{{citation | inventor-last = Berg | inventor-first = Lloyd | title = Recovery of ethylene glycol from butanediol isomers by azeotropic distillation | country-code = US | patent-number = 4966658 | year = 1990}}. {{citation | inventor-last = Berg | inventor-first = Lloyd | title = Separation of propylene glycol from 1,2-butanediol by azeotropic distillation | country-code = US | patent-number = 5423955 | year = 1995}}.</ref>
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==Applications==
==Applications==
It has been patented for the production of [[polyester]] [[resin]]s and [[plasticizer]]s.<ref name="SIDS"/><ref name="US4596886"/> It is a potential feedstock for the industrial production of [[α-ketobutyric acid]], a precursor to some [[amino acid]]s.<ref>{{citation | inventor1-last = Imanari | inventor1-first = Makoto | inventor2-last = Iwane | inventor2-first = Hiroshi | inventor3-last = Suzuki | inventor3-first = Masashi | inventor4-last = Suzuki | inventor4-first = Naoki | assignee = Mitsubishi Petrochemical Co., Ltd. | title = Process for preparing α-ketobutyric acid | country-code = US | patent-number = 5155263 | year = 1992}}.</ref>
It has been patented for the production of [[polyester]] [[resin]]s and [[plasticizer]]s.<ref name="SIDS"/><ref name="US4596886"/> It is a potential feedstock for the industrial production of [[α-ketobutyric acid]], a precursor to some [[amino acid]]s.<ref>{{citation | inventor1-last = Imanari | inventor1-first = Makoto | inventor2-last = Iwane | inventor2-first = Hiroshi | inventor3-last = Suzuki | inventor3-first = Masashi | inventor4-last = Suzuki | inventor4-first = Naoki | assignee = Mitsubishi Petrochemical Co., Ltd. | title = Process for preparing α-ketobutyric acid | country-code = US | patent-number = 5155263 | year = 1992}}.</ref>

==Safety==
The [[LD50]] (rats, oral) is 16g/kg.<ref name=Ullmann/>


==Notes==
==Notes==

Revision as of 21:16, 17 November 2018

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[1]
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 [2]
−2479 kJ/mol
Hazards[3]
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).
☒N verify (what is checkY☒N ?)

1,2-Butanediol is the organic compound with the formula HOCH2(HO)CHCH2CH3. It is classified as a vic-diol (glycol. It is chiral, although typically it is encountered as the racemic mixture. It is a colorless liquid.

Preparation

It is produced industrially by hydration of the 1,2-expoxybutane.[4][5]

1,2-Butanediol is a byproduct of the production of 1,4-butanediol from butadiene,[6] It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[7]

This diol was first described by Charles-Adolphe Wurtz in 1859.[8]

Applications

It has been patented for the production of polyester resins and plasticizers.[5][6] It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids.[9]

Safety

The LD50 (rats, oral) is 16g/kg.[4]

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.

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. ^ 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.
  3. ^ 1,2-Butanediol, International Chemical Safety Card 0395, Geneva: International Programme on Chemical Safety, March 1996.
  4. ^ a b "Butanediols, Butenediol, and Butynediol". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. 2005. doi:10.1002/14356007.a04_455. ISBN 978-3527306732.
  5. ^ a b 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
  6. ^ 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).
  7. ^ 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).
  8. ^ Wurtz, A. (1859), Ann. Chim. Phys., 55: 400{{citation}}: CS1 maint: untitled periodical (link).
  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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