| Revision as of 16:08, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465877166 of page 1,2-Butanediol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 08:17, 8 September 2024 edit Polygnotus (talk | contribs)Extended confirmed users, Rollbackers20,120 edits forula → formula |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443340093 |
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| Watchedfields = changed |
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| verifiedrevid = 477203212 |
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| Name = 1,2-Butanediol |
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| Name = 1,2-Butanediol |
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| ImageFile = 1,2-Butanediol.png |
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| ImageFile = 1,2-Butanediol.png |
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| ImageName = Molecular forula of 1,2-Butanediol |
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| ImageName = Molecular formula of 1,2-Butanediol |
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| ImageFile1 = 1,2-Butanediol-3D-balls-2.png |
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| IUPACName = Butane-1,2-diol |
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| ImageSize1 = |
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| OtherNames = 1,2-Dihydroxybutane<br/>α-Butylene glycol |
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| ImageAlt1 = Butanediol molecule |
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| Section1 = {{Chembox Identifiers |
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| PIN = Butane-1,2-diol |
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| InChI = 1/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 |
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| OtherNames = 1,2-Dihydroxybutane<br/>α-Butylene glycol |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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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 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 |
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| StdInChI = 1S/C4H10O2/c1-2-4(6)3-5/h4-6H,2-3H2,1H3 |
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| InChIKey = BMRWNKZVCUKKSR-UHFFFAOYAV |
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| InChIKey = BMRWNKZVCUKKSR-UHFFFAOYAV |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BMRWNKZVCUKKSR-UHFFFAOYSA-N |
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| StdInChIKey = BMRWNKZVCUKKSR-UHFFFAOYSA-N |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = RUN0H01QEU |
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| UNII = RUN0H01QEU |
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| SMILES = OCC(O)CC |
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| SMILES = OCC(O)CC |
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| SMILES1 = CCC(CO)O |
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| SMILES1 = CCC(CO)O |
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| CASNo = 584-03-2 |
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| CASNo = 584-03-2 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo1_Ref = {{cascite|changed|??}} |
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| EC-number = 209-527-2 |
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| CASNo1 = 40348-66-1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo1_Comment= (''R'') |
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| CASNo2_Ref = {{cascite|changed|??}} |
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| CASNo2 = 73522-17-5 |
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| CASNo2_Comment= (''S'') |
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| EC_number = 209-527-2 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 52682 |
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| ChEBI = 52682 |
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| ChemSpiderID = 10948 |
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| ChemSpiderID = 10948 |
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| RTECS = EK0380000 |
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| RTECS = EK0380000 |
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| PubChem = 11429 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Reference = <ref>{{RubberBible62nd|page=C-190}}.</ref><ref>{{Ullmann | volume = A1 | page = VA4 461}}.</ref><ref name="SIDS">{{SIDS-ref|id=584032|name=1,2-Butanediol|date=February 1995}}.</ref> |
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| Properties_ref = <ref>{{RubberBible62nd|page=C-190}}.</ref> |
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| Formula = C<sub>4</sub>H<sub>10</sub>O<sub>2</sub> |
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| Formula = C{{sub|4}}H{{sub|10}}O{{sub|2}} |
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| MolarMass = 90.121 g/mol |
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| MolarMass = 90.121 g/mol |
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| Density = 1.0023 g/cm<sup>3</sup> (20 °C) |
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| Density = 1.0023 g/cm{{sup|3}} (20 °C) |
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| MeltingPtC = −50 |
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| MeltingPt = −50 °C<ref group="note">The value of −50 °C for the melting point is taken from ''Ullmann's Encyclopedia of Industrial Chemistry'' and used by the ] and the OECD ]. Other reported values of the melting point range from −114 °C to −30 °C.</ref> |
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| MeltingPt_ref = <ref group="note">The value of −50 °C for the melting point is taken from ''Ullmann's Encyclopedia of Industrial Chemistry'' and used by the ] and the OECD ]. Other reported values of the melting point range from −114 °C to −30 °C.</ref> |
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| BoilingPt = 195–196.9 °C<br/>96.5 °C (10 mmHg) |
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| BoilingPtC = 195 to 196.9 |
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| Solubility = miscible |
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| BoilingPt_notes = (96.5 °C at 10 mmHg) |
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| SolubleOther = soluble in ], ]; sparingly soluble in ]s and ]s; insoluble in ]s |
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| Solubility = miscible |
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| RefractIndex = 1.4378 (20 °C) |
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| SolubleOther = soluble in ], ]; sparingly soluble in ]s and ]s; insoluble in ]s |
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| Viscosity = 7.3 mPa s (20 °C) |
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| RefractIndex = 1.4378 (20 °C) |
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| Viscosity = 7.3 mPa·s (20 °C) |
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| Section3 = {{Chembox Thermochemistry |
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|Section3={{Chembox Thermochemistry |
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| Reference = <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> |
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| 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 = ] | year = 1937 | volume = 4 | pages = 637–47}}.</ref> |
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| DeltaHf = −532.8 kJ/mol |
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| DeltaHc = −2479 kJ/mol |
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| DeltaHc = −2479 kJ/mol |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| Reference = <ref name="ICSC">{{ICSC-ref|03|95|name=1,2-Butanediol|date=March 1996}}.</ref> |
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| Hazards_ref = <ref name="ICSC">{{ICSC-ref|03|95|name=1,2-Butanediol|date=March 1996}}.</ref> |
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| ExternalMSDS = |
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| ExternalSDS = |
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| EUIndex = not listed |
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| FlashPtC = 90 |
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| FlashPt = 90 °C |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherFunctn = ]<br/>]<br/>] |
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| OtherFunction = ]<br/>]<br/>] |
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| Function = ]s |
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| OtherFunction_label = ]s |
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| OtherCpds = ]<br/>]<br/>]<br/>]<br/>] |
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| OtherCompounds = ]<br/>]<br/>]<br/>]<br/>] |
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'''1,2-Butanediol''' is the ] with the formula HOCH{{sub|2}}(HO)CHCH{{sub|2}}CH{{sub|3}}. It is classified as a ''vic''-diol (]). It is ], although typically it is encountered as the ]. It is a colorless liquid. |
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==Preparation== |
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This diol was first described by ] 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=]|volume=55|pages=400|year=1859|trans-title=Dissertation on glycols, or diatomic alcohols|authorlink=Charles-Adolphe Wurtz}}.</ref> |
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It is produced industrially by ] of ].<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> |
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:] |
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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> ] or strongly acidic ] may be used as catalysts, which allows the reaction to occur under 160 °C and at slightly above atmospheric pressure. |
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1,2-Butanediol is a byproduct of the production of ] from ].<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 ] to ] and ].<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> |
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It can also be obtained from the ] of ] by ]. |
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==Applications== |
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It has been patented for the production of ] ]s and ]s.<ref name="SIDS"/><ref name="US4596886"/> It is a potential feedstock for the industrial production of ], a precursor to some ]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> |
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==Safety== |
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The ] (rats, oral) is 16g/kg.<ref name=Ullmann/> |
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==Notes== |
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{{reflist|group="note"}} |
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==References== |
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{{reflist}} |
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==External links== |
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*{{ICSC|03|95}} |
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*{{SIDS| id=584032 |name=1,2-Butanediol|date=February 1995}} |
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{{DEFAULTSORT:Butanediol, 1, 2-}} |
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] |
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] |
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] |
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] |