| Revision as of 16:27, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465715812 of page 1,4-Butynediol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 21:35, 21 April 2024 edit Teaktl17 (talk | contribs)Extended confirmed users17,864 edits →See also: + alt. names for acetylenedicarboxylic acid |
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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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| Watchedfields = changed |
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| verifiedrevid = 444003443 |
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| verifiedrevid = 477205983 |
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| Name = 1,4-Butynediol |
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| Name = 1,4-Butynediol |
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| Reference =<ref></ref> |
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| Reference =<ref></ref> |
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| ImageFile = Butynediol.png |
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| ImageFile = Butynediol.png |
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| ImageSize = 150px |
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| ImageSize = 160px |
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| ImageAlt = Skeletal formula |
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| ImageName = 1,4-Butynediol |
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| ImageFile1 = Butynediol-3D-balls.png |
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| IUPACName = But-2-yne-1,4-diol |
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| ImageSize1 = 180 |
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| OtherNames = Butynediol<br />2-Butyne-1,4-diol<br />1,4-Dihydroxy-2-butyne |
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| ImageAlt1 = Ball-and-stick model |
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| Section1 = {{Chembox Identifiers |
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| PIN = But-2-yne-1,4-diol |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| OtherNames = Butynediol<br />2-Butyne-1,4-diol<br />1,4-Dihydroxy-2-butyne |
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|Section1={{Chembox Identifiers |
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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 = 16413 |
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| ChEBI = 16413 |
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| ChEMBL = 3187551 |
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| ChemSpiderID = 7775 |
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| ChemSpiderID = 7775 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C02497 |
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| KEGG = C02497 |
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| PubChem = 8066 |
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| EC_number = 203-788-6 |
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| RTECS = ES0525000 |
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| UNNumber = 2716 |
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| UNII = AXH202FPQM |
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| InChI = 1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2 |
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| InChI = 1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2 |
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| InChIKey = DLDJFQGPPSQZKI-UHFFFAOYAT |
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| InChIKey = DLDJFQGPPSQZKI-UHFFFAOYAT |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 110-65-6 |
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| CASNo = 110-65-6 |
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| SMILES = OCC#CCO |
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| SMILES = OCC#CCO |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=4|H=6|O=2 |
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| Formula = C<sub>4</sub>H<sub>6</sub>O<sub>2</sub> |
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| Density = 1.11 g/cm<sup>3</sup> (at 20 °C)<ref name=GESTIS>{{GESTIS|ZVG=29180}}</ref> |
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| MolarMass = 86.09 g/mol |
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| Appearance = Colorless crystalline solid<ref name=GESTIS/> |
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| Density = 1.2 g/cm³ |
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| Solubility = 3740 g/L<ref name=GESTIS/> |
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| MeltingPt = 52–55 °C |
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| MeltingPtC = 58 |
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| BoilingPt = 238 °C |
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| MeltingPt_ref= <ref name=GESTIS/> |
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| BoilingPtC = 238 |
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| BoilingPt_ref= <ref name=GESTIS/> |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| NFPA-H = 2 |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-R = 0 |
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| FlashPt = ~{{convert|136|C|F}} |
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| FlashPt_ref = <ref name=GESTIS/> |
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| GHSPictograms = {{GHS05}} {{GHS06}} {{GHS07}} {{GHS08}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|312|314|317|331|373}} |
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| PPhrases = {{P-phrases|260|261|264|270|271|272|280|301+310|301+330+331|302+352|303+361+353|304+340|305+351+338|310|311|312|314|321|322|330|333+313|363|403+233|405|501}} |
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'''1,4-Butynediol''' is an ] that is an ] and a ]. It is a colourless, hygroscopic solid that is soluble in water and polar ]s. It is a commercially significant compound in its own right and as a precursor to other products. |
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==Synthesis== |
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1,4-Butynediol can be produced in the ], where ] and ] are the reactants:<ref name="Ullmann">{{Ullmann|first1=Heinz|last1=Gräfje|first2=Wolfgang|last2=Körnig|first3=Hans-Martin|last3=Weitz|first4=Wolfgang|last4=Reiß|first5=Guido|last5=Steffan|first6=Herbert|last6=Diehl|first7=Horst |last7=Bosche|first8=Kurt|last8=Schneider|first9=Heinz|last9=Kieczka|title=Butanediols, Butenediol, and Butynediol|year=2000|doi=10.1002/14356007.a04_455}}</ref> |
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:2 CH<sub>2</sub>O + HC≡CH → HOCH<sub>2</sub>CCCH<sub>2</sub>OH |
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Several patented production methods use ] ] ]s coated on an inert material. The normal temperature range for the reaction is 90 °C up to 150 °C, depending on the pressure used for the reaction which can range from 1 to 20 bar.<ref>{{cite journal |
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| title = Butynediol synthesis. A kinetic study |
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| author = Kale S. S. |
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| author2 = Chaudhari R. V. |
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| author3 = Ramachandran P. A. |
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| journal = Industrial & Engineering Chemistry Product Research and Development |
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| year = 1981 |
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| volume = 20 |
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| issue = 2 |
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| pages = 309–315 |
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| doi = 10.1021/i300002a015 |
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}}</ref> |
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== Applications == |
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1,4-Butynediol is a precursor to ] and ] by ]. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and ]s. It is the major raw material used in the synthesis of ].<ref>{{Cite web |url=http://www.swchemical.com.cn/1,4butynediol.htm |title=1,4-Butynediol at Sanwei |access-date=2006-11-11 |archive-url=https://web.archive.org/web/20101204134416/http://www.swchemical.com.cn/1,4butynediol.htm |archive-date=2010-12-04 |url-status=dead }}</ref> It is also used for brightening, preserving, and inhibiting nickel plating.<ref name="Ullmann"/> |
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It reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO<sub>2</sub>CC(Cl)=C(Cl)CHO (see ]). |
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== Safety == |
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1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract. |
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==See also== |
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*] (but-2-ynedioic acid, 2-butynedioic acid) |
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*] |
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*] (but-2-yne) |
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== References == |
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<references/> |
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{{DEFAULTSORT:Butynediol14}} |
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] |
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] |