Difference between revisions of "Butane-1,2-diol"

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{{chembox
 
{{chembox
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| Name = 1,2-Butanediol
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| Name = Butane-1,2-diol
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| ImageFile = 1,2-Butanediol.png
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|  ImageName = Molecular forula of 1,2-Butanediol
 
| IUPACName = Butane-1,2-diol
 
| IUPACName = Butane-1,2-diol
 
|  OtherNames = 1,2-Dihydroxybutane<br/>α-Butylene glycol
 
|  OtherNames = 1,2-Dihydroxybutane<br/>α-Butylene glycol
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   }}
 
   }}
 
| Section2 = {{Chembox Properties
 
| Section2 = {{Chembox Properties
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|  Reference = <ref>{{RubberBible62nd|page=C-190}}.</ref><ref>{{Ullmann | volume = A1 | page = VA4&nbsp;461}}.</ref><ref name="SIDS">{{SIDS-ref|id=584032|name=1,2-Butanediol|date=February 1995}}.</ref>
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|  Reference = <ref name="CRC">{{RubberBible62nd|page=C-190}}.</ref><ref>{{Ullmann | volume = A1 | page = VA4&nbsp;461}}.</ref><ref name="SIDS">{{SIDS-ref|id=584032|name=1,2-Butanediol|date=February 1995}}.</ref>
 
|  Formula  = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub>
 
|  Formula  = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub>
 
|  MolarMass = 90.121 g/mol
 
|  MolarMass = 90.121 g/mol
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   }}
 
   }}
 
| Section8 = {{Chembox Related
 
| Section8 = {{Chembox Related
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|  OtherFunctn = [[1,3-Butanediol]]<br/>[[1,4-Butanediol]]<br/>[[2,3-Butanediol]]
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|  OtherFunctn = [[Butane-1,3-diol]]<br/>[[Butane-1,4-diol]]<br/>[[Butane-2,3-diol]]
 
|    Function = [[butanediol]]s
 
|    Function = [[butanediol]]s
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|  OtherCpds = [[Ethylene glycol]]<br/>[[Propylene glycol]]<br/>[[2-Hydroxybutyraldehyde]]<br/>[[2-Hydroxybutyric acid]]
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|  OtherCpds = [[Ethylene glycol]]<br/>[[Propylene glycol]]<br/>[[2-Hydroxybutyraldehyde]]<br/>[[2-Hydroxybutyric acid]]<br/>[[α-Ketobutyric acid]]
 
   }}
 
   }}
 
}}
 
}}
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{{FixBunching|mid}} <!-- specific rotations are: +14.5º (ethanol, ''c'' = 6; ''d''-form); −7.4º (ethanol, ''c'' = 4; ''l''-form). boiling pts: 192.4 ºC, 68 ºC (0.4 mmHg) (''d''-form); 94–96 ºC (12 mmHg) (''l''-form). Source: CRC -->
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{{chembox
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| Name = (''R'')-Butane-1,2-diol
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|  OtherNames =
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| Section1 = {{Chembox Identifiers
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|  InChI = 1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m1/s1
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|  StdInChI = 1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m1/s1
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|  InChIKey = BMRWNKZVCUKKSR-SCSAIBSYBR
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|  StdInChIKey = BMRWNKZVCUKKSR-SCSAIBSYSA-N
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|  ChemSpiderID = 556341
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  }}
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}}
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{{chembox
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| Name = (''S'')-Butane-1,2-diol
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|  OtherNames =
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| Section1 = {{Chembox Identifiers
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|  InChI = 1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m0/s1
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|  StdInChI = 1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m0/s1
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|  InChIKey = BMRWNKZVCUKKSR-BYPYZUCNBC
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|  StdInChIKey = BMRWNKZVCUKKSR-BYPYZUCNSA-N
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|  ChemSpiderID = 5361290
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  }}
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}}
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'''Butane-1,2-diol''' is a ''vic''-diol ([[glycol]]) first described by [[Charles-Adolphe Wurtz]] in 1859.<ref>{{citation | last = Wurtz | first = A. | authorlink = Charles-Adolphe Wurtz | journal = Ann. Chim. Phys. | year = 1859 | volume = 55 | pages = 400}}.</ref> It is produced industrially as a byproduct of the production of [[butane-1,4-diol]] 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> and 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><ref group="note">It should be noted that the catalytic hydrocracking of starches and sugars is not currently a major industrial route to [[ethylene glycol]] and [[propylene glycol]], partly because of the complexity of the mixtures of polyhydric alcohols which is formed.</ref> It is used to produced [[polyester]] [[resin]]s and [[plasticizer]]s,<ref name="SIDS"/><ref name="US4596886"/> and is a potential feedstock for the industrial production of [[α-ketobutyric acid]], a precursor to many [[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>
 
'''Butane-1,2-diol''' is a ''vic''-diol ([[glycol]]) first described by [[Charles-Adolphe Wurtz]] in 1859.<ref>{{citation | last = Wurtz | first = A. | authorlink = Charles-Adolphe Wurtz | journal = Ann. Chim. Phys. | year = 1859 | volume = 55 | pages = 400}}.</ref> It is produced industrially as a byproduct of the production of [[butane-1,4-diol]] 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> and 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><ref group="note">It should be noted that the catalytic hydrocracking of starches and sugars is not currently a major industrial route to [[ethylene glycol]] and [[propylene glycol]], partly because of the complexity of the mixtures of polyhydric alcohols which is formed.</ref> It is used to produced [[polyester]] [[resin]]s and [[plasticizer]]s,<ref name="SIDS"/><ref name="US4596886"/> and is a potential feedstock for the industrial production of [[α-ketobutyric acid]], a precursor to many [[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>
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==External links==
 
==External links==
 +
{{Wikipedia|1,2-Butanediol}}
 
*{{ICSC|03|95}}
 
*{{ICSC|03|95}}
 
*{{SIDS|id=584032|name=1,2-Butanediol|date=February 1995}}
 
*{{SIDS|id=584032|name=1,2-Butanediol|date=February 1995}}

Latest revision as of 11:44, 29 August 2009

Butane-1,2-diol
Molecular forula of 1,2-Butanediol
IUPAC name Butane-1,2-diol
Other names 1,2-Dihydroxybutane
α-Butylene glycol
Identifiers
InChI InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3
InChIKey BMRWNKZVCUKKSR-UHFFFAOYAV
Standard InChI InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3
Standard InChIKey BMRWNKZVCUKKSR-UHFFFAOYSA-N
CAS number [584-03-2]
EC number 209-527-2
RTECS EK0380000
ChemSpider 10948
Properties[1][2][3]
Chemical formula C4H10O2
Molar mass 90.121 g/mol
Density 1.0023 g/cm3 (20 ºC)
Melting point

−50 °C[note 1]

Boiling point

195–196.9 °C
96.5 ºC (10 mmHg)

Solubility in water miscible
Solubility soluble in ethanol, acetone; sparingly soluble in esters and ethers; insoluble in hydrocarbons
Refractive index (nD) 1.4378 (20 ºC)
Viscosity 7.3 mPa s (20 ºC)
Thermochemistry[4]
Std enthalpy of formation ΔfHo298 −532.8 kJ/mol
Std enthalpy of combustion ΔcHo298 −2479 kJ/mol
Hazards[5]
Material safety data sheet (MSDS) ICSC 0395
EU index number not listed
Flash point 90 ºC
Related compounds
Other butanediols Butane-1,3-diol
Butane-1,4-diol
Butane-2,3-diol
Other compounds Ethylene glycol
Propylene glycol
2-Hydroxybutyraldehyde
2-Hydroxybutyric acid
α-Ketobutyric acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
(R)-Butane-1,2-diol
Identifiers
InChI InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m1/s1
InChIKey BMRWNKZVCUKKSR-SCSAIBSYBR
Standard InChI InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m1/s1
Standard InChIKey BMRWNKZVCUKKSR-SCSAIBSYSA-N
ChemSpider 556341
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
(S)-Butane-1,2-diol
Identifiers
InChI InChI=1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m0/s1
InChIKey BMRWNKZVCUKKSR-BYPYZUCNBC
Standard InChI InChI=1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3/t4-/m0/s1
Standard InChIKey BMRWNKZVCUKKSR-BYPYZUCNSA-N
ChemSpider 5361290
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Butane-1,2-diol 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 butane-1,4-diol 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 produced 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 ºC 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. ↑ It should be noted that the catalytic hydrocracking of starches and sugars is not currently a major industrial route to ethylene glycol and propylene glycol, partly because of the complexity of the mixtures of polyhydric alcohols which is formed.

References

  1. ↑ CRC Handbook of Chemistry and Physics, 62nd ed.; Weast, Robert C., Ed.; CRC Press: Boca Raton, FL, 1981; p C-190. ISBN 0-8493-0462-8.
  2. ↑ Ullmann’s Encyclopedia of Industrial Chemistry, 5th ed.; Wiley-VCH: Weinheim, 2005; Vol. A1, p VA4 461.
  3. ↑ 3.0 3.1 1,2-Butanediol; SIDS Initial Assessment Report; Organisation for Economic Co-operation and Development, February 1995, <http://www.inchem.org/documents/sids/sids/584032.pdf>.
  4. ↑ Moureu, H.; Dode, M. Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues. Bull. Soc. Chim. Fr. 1937, 4, 637–47.
  5. ↑ 1,2-Butanediol; International Chemical Safety Card 0395; International Labour Organization: Geneva, March 1996, <http://www.inchem.org/documents/icsc/icsc/eics0395.htm>.
  6. ↑ Wurtz, A. Ann. Chim. Phys. 1859, 55, 400.
  7. ↑ 7.0 7.1 Hasegawa, Ryuichi; Hayashi, Kohji (Mitsubishi Monsanto Chemical Company) Polyester containing impure 1,2-butanediol. US Patent 4596886, published 22 November 1986.
  8. ↑ Berg, Lloyd Recovery of ethylene glycol from butanediol isomers by azeotropic distillation. US Patent 4966658, published 22 November 1990. Berg, Lloyd Separation of propylene glycol from 1,2-butanediol by azeotropic distillation. US Patent 5423955, published 22 November 1995.
  9. ↑ Imanari, Makoto; Iwane, Hiroshi; Suzuki, Masashi, et al. (Mitsubishi Petrochemical Co., Ltd.) Process for preparing α-ketobutyric acid. US Patent 5155263, published 22 November 1992.

External links

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