| 词条 | Tetrolic acid |
| 释义 |
|Name=Tetrolic acid |ImageFile=Tetrolic acid.png |ImageSize=240px |ImageAlt=Skeletal formula of tetrolic acid |ImageFile2 = Tetrolic acid (2-butynoic acid) crystals.jpg |ImageSize2=240px |ImageAlt2=Crystals of tetrolic acid |PIN=But-2-ynoic acid |OtherNames=2-Butynoic acid But-2-ynoic acid Butynoic acid |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 61810 | PubChem=68535 | SMILES1 = CC#CC(=O)O | CASNo = 590-93-2 | InChI=1S/C4H4O2/c1-2-3-4(5)6/h1H3,(H,5,6)| InChIKey=LUEHNHVFDCZTGL-UHFFFAOYSA-N}} |Section2={{Chembox Properties | C=4|H=4|O=2 | Density = 0.9641 g/cm3[1] | MeltingPtC = 78 | MeltingPt_ref = [1] | BoilingPtC = 203 | BoilingPt_ref = [1] }} }} Tetrolic acid (2-butynoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3-C≡C-CO2H. Salts and esters of tetrolic acid are known as tetrolates. HistoryThe first reported synthesis[2] of tetrolic acid is believed to be by German chemist Johann Georg Anton Geuther in 1871 as part of his work investigating the derivatives of ethyl acetoacetate. ProductionTetrolic acid is manufactured[3] on a commercial scale by treatment of propyne with a strong base (to form an acetylide), followed by carbon dioxide: {{Clear left}}Strong bases such as n-BuLi[4] and NaNH2[5] can be used. PropertiesTetrolic acid is highly soluble in polar solvents (water, ethanol) and may be recrystallized from non polar solvents (such as heptane, toluene). The compound is a white crystalline solid which can exist in two polymorphous crystalline forms.[6] The proton nuclear magnetic resonance (1H-NMR) spectrum in deuterated dimethyl sulfoxide shows a characteristic singlet peak at 1.99 ppm corresponding to the -CH3 protons. References{{Commons category|Tetrolic acid}}1. ^1 2 {{RubberBible92nd|page=3.88}} 2. ^{{cite journal|last=Geuther|first=A.|authorlink=Johann Georg Anton Geuther|title=Ethyldiacetic Acid and some of its Derivatives|journal=J. Chem. Soc.|year=1871|volume=24|pages=812–837|doi=10.1039/JS8712400808 }} 3. ^Smith, W. (1973) "Preparation of tetrolic acid" {{US Patent|3752848A}} 4. ^{{cite journal|doi = 10.1039/P19940002525|first1 = Basil|last1 = Hartzoulakis|first2 = David|last2 = Gani|title = Synthesis of (2S, 3R)- and (2S, 3S)-3-methylglutamic acid|journal = J. Chem. Soc., Perkin Trans. 1|pages = 2525–2531|volume = 1994|issue = 18|year = 1994}} 5. ^{{OrgSynth|doi = 10.15227/orgsyn.042.0097|title = Tetrolic Acid (2-Butynoic Acid)|volume = 42|pages = 97|year = 1962|collvol = 5|collvolpages = 1043|prep = CV5P1043|first1 = J. C.|last1 = Kauer|first2 = M.|last2 = Brown}} 6. ^{{cite journal|doi=10.1016/j.chemphys.2008.01.035|journal=Chemical Physics|year=2008|volume=345|issue=1|pages=49–64|title= Effects of "excessive" exciton interactions in polarized IR spectra of the hydrogen bond in 2-butynoic acid crystals: Proton transfer induced by dynamical co-operative interactions involving hydrogen bonds|last1= Flakus|first1= Henryk T.|last2= Hachuła|first2= Barbara}} 2 : Carboxylic acids|Alkynes |
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