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Chemical Structure| 61305-27-9 Chemical Structure| 61305-27-9
Chemical Structure| 61305-27-9

4-Hydroxy-2-cyclopentenone

CAS No.: 61305-27-9

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Cat. No.: A186756 Purity: 98%

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Product Citations

Orozco-Saumell, Ana ; Mariscal, Rafael ; Vila, Francisco ; Lopez Granados, Manuel ; Alonso, David Martin ;

Abstract: The catalytic transformation of furfural to cyclopentanone has been investigated using two different liquid phases as solvent: water and 30 wt.% tert–butanol in water. When using neat water at 160 °C, 40 bar of H2, and after 2 h of reaction time, furfural polymerizes, and the yield of cyclopentanone is just 42% with a low carbon balance, indicating that furfural is transformed to non-detected by-products, likely heavy resins. When using 30 wt.% tert–butanol in water, the yield of cyclopentanone is ca. 20%, and the major product is furfuryl alcohol with a 47% yield. We have studied the catalytic transformation of the most relevant reaction intermediates in the overall conversion of furfural to cyclopentanone. In the presence of tert–butanol, two steps are inhibited in the overall pathway: (i) the Piancatelli rearrangement of furfuryl alcohol and (ii) the transformation of cyclopentenone. This inhibition is attributed to the neutralization of protons from water dissociation by surface sites on the catalyst, preventing their participation in the overall reaction. To counteract these inhibitions when tert–butanol is present, higher H2 pressure (60 bar) and temperatures (200 °C) are required. We have been able to obtain productivities per gram of catalyst and mols of Cu basis of 411 gprod·h−1·gcat−1 and 14 gprod·s−1·molCu−1, respectively, which is substantially above that found for other copper-based catalysts.

Keywords: cyclopentanone ; furfural ; hydrogenation ; Cu/ZnO/Al2O3 ; reaction intermediates

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Product Details of [ 61305-27-9 ]

CAS No. :61305-27-9
Formula : C5H6O2
M.W : 98.10
SMILES Code : O=C1C=CC(O)C1
MDL No. :MFCD09035055
InChI Key :DHNDDRBMUVFQIZ-UHFFFAOYSA-N
Pubchem ID :4169160

Safety of [ 61305-27-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338
 

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Technical Information

• Appel Reaction • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Halogenation • Heat of Combustion • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Lawesson's Reagent • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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