1,4-Butynediol
{{chembox
| Watchedfields = changed
| verifiedrevid = 477205983
| Name = 1,4-Butynediol
| Reference =[http://www.chemicalland21.com/industrialchem/solalc/1,4-BUTYNEDIOL.htm 1,4-Butynediol at chemicalland21.com]
| ImageFile = Butynediol.png
| ImageSize = 160px
| ImageAlt = Skeletal formula
| ImageFile1 = Butynediol-3D-balls.png
| ImageSize1 = 180
| ImageAlt1 = Ball-and-stick model
| PIN = But-2-yne-1,4-diol
| OtherNames = Butynediol
2-Butyne-1,4-diol
1,4-Dihydroxy-2-butyne
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 16413
| ChEMBL = 3187551
| ChemSpiderID = 7775
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C02497
| PubChem = 8066
| EC_number = 203-788-6
| RTECS = ES0525000
| UNNumber = 2716
| UNII = AXH202FPQM
| InChI = 1/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2
| InChIKey = DLDJFQGPPSQZKI-UHFFFAOYAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DLDJFQGPPSQZKI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 110-65-6
| SMILES = OCC#CCO
}}
|Section2={{Chembox Properties
| C=4|H=6|O=2
| Density = 1.11 g/cm3 (at 20 °C){{GESTIS|ZVG=29180}}
| Appearance = Colorless crystalline solid
| MeltingPtC = 58
| BoilingPtC = 238
}}
|Section7={{Chembox Hazards
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| FlashPt = ~{{convert|136|C|F}}
| GHSPictograms = {{GHS05}} {{GHS06}} {{GHS07}} {{GHS08}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|312|314|317|331|373}}
| 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}}
}}
}}
1,4-Butynediol is an organic compound that is an alkyne and a diol. It is a colourless, hygroscopic solid that is soluble in water and polar organic solvents. It is a commercially significant compound in its own right and as a precursor to other products.
Synthesis
1,4-Butynediol can be produced in the Reppe synthesis, where formaldehyde and acetylene are the reactants:{{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}}
:2 CH2O + HC≡CH → HOCH2CCCH2OH
Several patented production methods use copper bismuth catalysts 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.{{cite journal
| title = Butynediol synthesis. A kinetic study
| author = Kale S. S.
| author2 = Chaudhari R. V.
| author3 = Ramachandran P. A.
| journal = Industrial & Engineering Chemistry Product Research and Development
| year = 1981
| volume = 20
| issue = 2
| pages = 309–315
| doi = 10.1021/i300002a015
}}
Applications
1,4-Butynediol is a precursor to 1,4-butanediol and 2-butene-1,4-diol by hydrogenation. It is also used in the manufacture of certain herbicides, textile additives, corrosion inhibitors, plasticizers, synthetic resins, and polyurethanes. It is the major raw material used in the synthesis of vitamin B6.{{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 }} It is also used for brightening, preserving, and inhibiting nickel plating.
It reacts with a mixture of chlorine and hydrochloric acid to give mucochloric acid, HO2CC(Cl)=C(Cl)CHO (see mucobromic acid).
Safety
1,4-Butynediol is corrosive and irritates the skin, eyes, and respiratory tract.
See also
- Acetylenedicarboxylic acid (but-2-ynedioic acid, 2-butynedioic acid)
- cis-Butene-1,4-diol
- 2-Butyne (but-2-yne)