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{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 477203212
| verifiedrevid = 477203212
| Name = 1,2-Butanediol
| Name = 1,2-Butanediol
| ImageFile = 1,2-Butanediol.png
| ImageFile = 1,2-Butanediol.png
| ImageName = Molecular forula of 1,2-Butanediol
| ImageName = Molecular formula of 1,2-Butanediol
| ImageFile1 = 1,2-Butanediol-3D-balls-2.png
| ImageFile1 = 1,2-Butanediol-3D-balls-2.png
| ImageSize1 =
| ImageSize1 =
| ImageAlt1 = Butanediol molecule
| ImageAlt1 = Butanediol molecule
| IUPACName = Butane-1,2-diol
| PIN = Butane-1,2-diol
| OtherNames = 1,2-Dihydroxybutane<br/>α-Butylene glycol
| OtherNames = 1,2-Dihydroxybutane<br/>α-Butylene glycol
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
Line 23: Line 24:
| CASNo = 584-03-2
| CASNo = 584-03-2
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1_Ref = {{cascite|changed|??}}
| CASNo1 = 40348-66-1
| CASNo1_Comment= (''R'')
| CASNo2_Ref = {{cascite|changed|??}}
| CASNo2 = 73522-17-5
| CASNo2_Comment= (''S'')
| EC_number = 209-527-2
| EC_number = 209-527-2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChemSpiderID = 10948
| ChemSpiderID = 10948
| RTECS = EK0380000
| RTECS = EK0380000
| PubChem = 11429
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| 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>
| Properties_ref = <ref>{{RubberBible62nd|page=C-190}}.</ref>
| Formula = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub>
| Formula = C{{sub|4}}H{{sub|10}}O{{sub|2}}
| MolarMass = 90.121 g/mol
| MolarMass = 90.121 g/mol
| Density = 1.0023 g/cm<sup>3</sup> (20 °C)
| Density = 1.0023 g/cm{{sup|3}} (20 °C)
| MeltingPtC = −50
| MeltingPtC = −50
| 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>
| 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>
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| 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
| RefractIndex = 1.4378 (20 °C)
| RefractIndex = 1.4378 (20 °C)
| Viscosity = 7.3 mPa&thinsp;s (20 °C)
| Viscosity = 7.3 mPa·s (20 °C)
}}
}}
|Section3={{Chembox Thermochemistry
|Section3={{Chembox Thermochemistry
| DeltaHf = −532.8 kJ/mol <ref>{{citation | last1 = Moureu | first1 = H. | last2 = Dode | first2 = M. | title = Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues | journal = Bull. Soc. Chim. Fr. | year = 1937 | volume = 4 | pages = 637–47}}.</ref>
| DeltaHf = −532.8 kJ/mol <ref>{{citation | last1 = Moureu | first1 = H. | last2 = Dode | first2 = M. | title = Chaleurs de formation de l'oxyde d'ethylene, de l'ethanediol et de quelques homologues | journal = [[Bull. Soc. Chim. Fr.]] | year = 1937 | volume = 4 | pages = 637–47}}.</ref>
| DeltaHc = −2479 kJ/mol
| DeltaHc = −2479 kJ/mol
}}
}}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| Reference = <ref name="ICSC">{{ICSC-ref|03|95|name=1,2-Butanediol|date=March 1996}}.</ref>
| Hazards_ref = <ref name="ICSC">{{ICSC-ref|03|95|name=1,2-Butanediol|date=March 1996}}.</ref>
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0395.htm ICSC 0395]
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0395.htm ICSC 0395]
| FlashPtC = 90
| FlashPtC = 90
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}}
}}


'''1,2-Butanediol''' is the [[organic compound]] with the formula HOCH{{sub|2}}(HO)CHCH{{sub|2}}CH{{sub|3}}. 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.
⚫
'''1,2-Butanediol''' is a ''vic''-diol ([[glycol]]) first described by [[Charles-Adolphe Wurtz]] in 1859.<ref>{{citation |title=none| 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 [[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> 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"> 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</ref> It is used to produce [[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>

==Preparation==
This diol was first described by [[Charles-Adolphe Wurtz]] in 1859.<ref>{{citation|last=Wurtz|first=A.|title=Mémoire sur les glycols ou alcools diatomique|url=https://gallica.bnf.fr/ark:/12148/bpt6k6567326h/f403.item|journal=[[Ann. Chim. Phys.]]|volume=55|pages=400|year=1859|trans-title=Dissertation on glycols, or diatomic alcohols|authorlink=Charles-Adolphe Wurtz}}.</ref>

It is produced industrially by [[Hydration reaction|hydration]] of [[1,2-Epoxybutane|1,2-epoxybutane]].<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>

:[[File:Industrial_synthesis_of_1,2-butanediol.svg|378x378px]]
This process requires a ten- to twenty-fold excess of water to suppress the formation of polyethers. Depending on the amount of excess water, the selectivity varies from 70 to 92%.<ref>{{Citation|last1=Gräfje|first1=Heinz|title=Butanediols, Butenediol, and Butynediol|date=2019-07-23|url=https://onlinelibrary.wiley.com/doi/10.1002/14356007.a04_455.pub2|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|pages=1–12|place=Weinheim, Germany|publisher=Wiley-VCH Verlag GmbH & Co. KGaA|language=en|doi=10.1002/14356007.a04_455.pub2|isbn=978-3-527-30673-2|access-date=2022-02-18|last2=Körnig|first2=Wolfgang|last3=Weitz|first3=Hans-Martin|last4=Reiß|first4=Wolfgang|last5=Steffan|first5=Guido|last6=Diehl|first6=Herbert|last7=Bosche|first7=Horst|last8=Schneider|first8=Kurt|last9=Kieczka|first9=Heinz}}</ref> [[Sulfuric acid]] or strongly acidic [[ion exchange resins]] may be used as catalysts, which allows the reaction to occur under 160&nbsp;°C and at slightly above atmospheric pressure.

⚫
1,2-Butanediol is a byproduct of the production of [[1,4-butanediol]] from [[butadiene]].<ref name="US4596886">{{cite patent | inventor1-last = Hasegawa | inventor1-first = Ryuichi | inventor2-last = Hayashi | inventor2-first = Kohji | assign = Mitsubishi Monsanto Chemical Company | title = Polyester containing impure 1,2-butanediol | country= US | number = 4596886 | pubdate = 1986-06-24}}.</ref> It is also a byproduct of the catalytic hydrocracking of starches and sugars such as [[sorbitol]] to [[ethylene glycol]] and [[propylene glycol]].<ref>{{cite patent | inventor-last = Berg | inventor-first = Lloyd | title = Recovery of ethylene glycol from butanediol isomers by azeotropic distillation | country= US | number = 4966658 | pubdate = 1990-10-30}}. {{cite patent | inventor-last = Berg | inventor-first = Lloyd | title = Separation of propylene glycol from 1,2-butanediol by azeotropic distillation | country = US | number = 5423955 | pubdate = 1995-06-13}}.</ref>

It can also be obtained from the [[dihydroxylation]] of [[1-Butene|but-1-ene]] by [[OsO4|OsO<sub>4</sub>]].

==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>{{cite patent | inventor1-last = Imanari | inventor1-first = Makoto | inventor2-last = Iwane | inventor2-first = Hiroshi | inventor3-last = Suzuki | inventor3-first = Masashi | inventor4-last = Suzuki | inventor4-first = Naoki | assign = Mitsubishi Petrochemical Co., Ltd. | title = Process for preparing α-ketobutyric acid | country = US | number = 5155263 | pubdate = 1992-10-13}}.</ref>

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


==Notes==
==Notes==
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*{{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}}
*{{HSDB|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~1xTLm7:1|name=1,2-butanediol}}


{{DEFAULTSORT:Butanediol, 1,2-}}
{{DEFAULTSORT:Butanediol, 1, 2-}}
[[Category:Alkanediols]]
[[Category:Alkanediols]]
[[Category:Vicinal diols]]
[[Category:Substances discovered in the 19th century]]
[[Category:Butane]]

Latest revision as of 08:17, 8 September 2024

1,2-Butanediol
Molecular formula of 1,2-Butanediol
Butanediol molecule
Names
Preferred 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

[edit]

This diol was first described by Charles-Adolphe Wurtz in 1859.[4]

It is produced industrially by hydration of 1,2-epoxybutane.[5][6]

This process requires a ten- to twenty-fold excess of water to suppress the formation of polyethers. Depending on the amount of excess water, the selectivity varies from 70 to 92%.[7] Sulfuric acid or strongly acidic ion exchange resins may be used as catalysts, which allows the reaction to occur under 160 °C and at slightly above atmospheric pressure.

1,2-Butanediol is a byproduct of the production of 1,4-butanediol from butadiene.[8] It is also a byproduct of the catalytic hydrocracking of starches and sugars such as sorbitol to ethylene glycol and propylene glycol.[9]

It can also be obtained from the dihydroxylation of but-1-ene by OsO4.

Applications

[edit]

It has been patented for the production of polyester resins and plasticizers.[6][8] It is a potential feedstock for the industrial production of α-ketobutyric acid, a precursor to some amino acids.[10]

Safety

[edit]

The LD50 (rats, oral) is 16g/kg.[5]

Notes

[edit]
  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

[edit]
  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. ^ Wurtz, A. (1859), "Mémoire sur les glycols ou alcools diatomique" [Dissertation on glycols, or diatomic alcohols], Ann. Chim. Phys., 55: 400.
  5. ^ 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.
  6. ^ a b 1,2-Butanediol (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, February 1995.
  7. ^ Gräfje, Heinz; Körnig, Wolfgang; Weitz, Hans-Martin; Reiß, Wolfgang; Steffan, Guido; Diehl, Herbert; Bosche, Horst; Schneider, Kurt; Kieczka, Heinz (2019-07-23), "Butanediols, Butenediol, and Butynediol", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. 1–12, doi:10.1002/14356007.a04_455.pub2, ISBN 978-3-527-30673-2, retrieved 2022-02-18
  8. ^ a b US 4596886, Hasegawa, Ryuichi & Hayashi, Kohji, "Polyester containing impure 1,2-butanediol", published 1986-06-24, assigned to Mitsubishi Monsanto Chemical Company .
  9. ^ US 4966658, Berg, Lloyd, "Recovery of ethylene glycol from butanediol isomers by azeotropic distillation", published 1990-10-30 . US 5423955, Berg, Lloyd, "Separation of propylene glycol from 1,2-butanediol by azeotropic distillation", published 1995-06-13 .
  10. ^ US 5155263, Imanari, Makoto; Iwane, Hiroshi & Suzuki, Masashi et al., "Process for preparing α-ketobutyric acid", published 1992-10-13, assigned to Mitsubishi Petrochemical Co., Ltd. .
[edit]
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