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Cas Database

108-10-1

108-10-1

Identification

  • Product Name:2-Pentanone,4-methyl-

  • CAS Number: 108-10-1

  • EINECS:203-550-1

  • Molecular Weight:100.161

  • Molecular Formula: C6H12O

  • HS Code:2914.13 Oral rat LD50; 2737 mg/kg

  • Mol File:108-10-1.mol

Synonyms:2-Methyl-4-pentanone;2-Methylpropyl methyl ketone;4-Methyl-2-oxopentane;Hexone;Isobutyl methyl ketone;Isopropylacetone;MIBK;MIK;Methyl2-methylpropyl ketone;Methyl iso-butyl ketone;Methyl isobutyl ketone;NSC5712;Methyl Isobutyl Ketone (MIBK);4-Methyl-2-pentanone;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,HarmfulXn,ToxicT

  • Hazard Codes:F,Xn,T

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Refer for medical attention . Vapor causes irritation of eyes and nose; high concentrations cause anesthesia and depression. Liquid dries out skin and may cause dermatitis; irritates eyes but does not injure them. (USCG, 1999) INHALATION: Symptoms: Cough. Diarrhea. Dizziness. Headache. Nausea. Sore throat. Unconsciousness. Vomiting. Weakness. Loss of appetite. First aid: Fresh air, rest. Refer for medical attention. SKIN: Symptoms: Dry skin. Redness. Pain. First aid: Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention. EYES: Symptoms: Redness. Pain. First aid: First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then take to a doctor. INGESTION: Symptoms: Abdominal pain. First aid: Rinse mouth. Do NOT induce vomiting. Refer for medical attention.

  • Fire-fighting measures: Suitable extinguishing media ... Water should not be used, since this may cause the fire to spread, though a water spray can be used to cool containers. Special Hazards of Combustion Products: Irritating vapors are generated when heated. Behavior in Fire: Vapors may travel a considerable distance and ignite. (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Oil-skimming equipment and sorbent foams can be applied to slick if done immediately. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from strong oxidants. Well closed.... OPEN LIGHTS OR OTHER AGENCIES LIABLE TO IGNITE THE VAPOR SHOULD BE EXCLUDED FROM THOSE AREAS WHERE LIQUID IS BEING STORED OR USED. /KETONES/

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 50 ppm (205 mg/cu m).Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 75 ppm (300 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:4-Methyl-2-pentanone
  • Packaging:25g
  • Price:$ 135
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Methyl-2-pentanone >99.5%(GC)
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  • Price:$ 16
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Methyl-2-pentanone >99.5%(GC)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:4-Methyl-2-pentanone 99%
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  • Product Description:Methyl Isobutyl Ketone Pharmaceutical Secondary Standard; Certified Reference Material
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  • Product Description:4-Methyl-2-pentanone ≥99%, FCC
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  • Product Description:4-Methyl-2-pentanone ≥99%
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Relevant articles and documentsAll total 253 Articles be found

Palladium catalyzed mild reduction of α,β-unsaturated compounds by triethylsilane

Mirza-Aghayan, Maryam,Boukherroub, Rabah,Bolourtchian, Mohammad,Rahimifard, Mahshid

, p. 5113 - 5116 (2007)

The palladium(II) chloride/triethylsilane system has been successfully applied for the selective hydrogenation of the carbon-carbon double bond of α,β-unsaturated ketones to yield the corresponding saturated carbonyl compounds. The reaction takes place under mild conditions and affords high yields.

Multifunctional catalysis by Pd-polyoxometalate: One-step conversion of acetone to methyl isobutyl ketone

Hetterley, Robert D.,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.

, p. 782 - 784 (2006)

Pd metal supported on Cs2.5H0.5PW12O 40 is an efficient bifunctional catalyst for the one-step conversion of acetone to methyl isobutyl ketone in gas and liquid phase. The Royal Society of Chemistry 2006.

2-Phenylbenzothiazoline as a Reducing Agent in the Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds

Chikashita, Hidenori,Miyazaki, Makoto,Itoh, Kazuyoshi

, p. 308 - 310 (1984)

-

Use of reductive properties of iodotrichlorosilane II: Chemoselective reduction of α,β-unsaturated ketones and nitriles

Elmorsy, Saad S.,El-Ahl, Abdel-Aziz S.,Soliman, Hanan,Amer, Fathy A.

, p. 2297 - 2298 (1996)

A new synthetic procedure for the selective reduction of α,β-unsaturated ketones and nitriles, using iodotrichlorosilane (ITCS generated in situ from SiCl4-NaI) under mild conditions to produce the corresponding saturated ketone and nitrile compounds in quantitative yields, is described.

Selective deoximation using alumina supported potassium permanganate

Chrisman, William,Blankinship, Michael J,Taylor, Brady,Harris, Clifford E

, p. 4775 - 4777 (2001)

Ketoximes are converted to the parent ketones in good yields when treated with potassium permanganate supported on neutral alumina (ASPP). An optimized procedure has been developed, the simple work-up minimizes loss of product and oximes have been selectively oxidized in the presence of alkenes.

-

Dauben et al.

, p. 1849 (1969)

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Alkoxy radical isomerization products from the gas-phase OH radical- initiated reactions of 2,4-dimethyl-2-pentanol and 3,5-dimethyl-3-hexanol

Atkinson,Aschmann

, p. 528 - 536 (1995)

The products of the gas-phase reactions of the OH radical with 2,4- dimethyl-2-pentanol and 3,5-dimethyl-3-hexanol in the presence of NO(x) have been determined at atmospheric pressure of air and 296 ± 2 K to assess the occurrence and importance of alkoxy radical isomerization. The products identified and quantified and their formation yields were as follows: from 2,4-dimethyl-2-pentanol: acetone, 0.92 ± 0.15; 2-methylpropanal, 0.209 ± 0.022; 4-methyl-2-2-pentanone, 0.046 ± 0.008; and 4-hydroxy-4-methyl-2- pentanone, 0.116 ± 0.018; from 3,5-dimethyl-3-hexanol: acetone, 0.120 ± 0.029; 2-butanone, 0.275 ± 0.021; 2-methylpropanal, 0.169 ± 0.016; 4- methyl-2-pentanone, 0.161 ± 0.012; and 4-hydroxy-4-methyl-2-pentanone, 0.250 ± 0.023. The observed formation of 4-hydroxy-4-methyl-2-pentanone provides conclusive evidence for the occurrence of isomerization of the alkoxy radicals (CH3)2C(OH)CH2C(O)(CH3)2 and CH3CH2C(CH3)(OH)CH2C(O)(CH3)2 via 1,5-H shifts. The reaction mechanisms are discussed, and isomerization rate constants for 1,5-H-atom abstraction from the -CH3 and -CH2- groups in the RCH2C(CH3)(OH)- CH2C(O)(CH3)2 alkoxy radicals (R = H and CH3) are derived.

Chemical aspects of electrocatalytic reduction of carbonyl compounds. Mesityl oxide

Shchelkunov,Mazakova,Bekenova,Amirkhanova,Shchelkunov

, p. 446 - 447 (2001)

-

Ethanolic or aqueous formic acid (1:1) - A new efficient reagent for the regeneration of ketones from phenylhydrazones

Chakrabarty, Manas,Khasnobis, Shampa

, p. 1361 - 1368 (1998)

50% Ethanolic or aqueous formic acid has been found to be extremely efficacious for the regeneration of aliphatic and aromatic ketones from phenylhydrazones.

Variable regiochemistry in the stoichiometric and catalytic hydroamination of alkynes by imidozirconium complexes caused by an unusual dependence of the rate law on alkyne structure and temperature

Baranger, Anne M.,Walsh, Patrick J.,Bergman, Robert G.

, p. 2753 - 2763 (1993)

We have investigated the regiochemistry of the stoichiometric and catalytic hydroamination of disubstituted alkynes by imidozirconium complexes. The addition of alkynes to Cp2Zr=NR occurred regioselectively to give metallacycles 2, with the larger alkyne substituent RL located α to the metal center. Hydrolysis of the metallacycles then gave enamines and their tautomeric imines which were the net result of anti-Markovnikov addition to the alkyne. The size of the R group on the imido ligand and the size of the alkyne were influential in determining the degree of regioselectivity. By utilizing Cp2(THF)Zr=NR to generate Cp2Zr=NR at room temperature and Cp2Zr(R′)(NHR) to generate Cp2Zr=NR at high temperature, it was determined that the thermodynamic and kinetic regioselectivities were nearly identical for dialkylacetylenes. In contrast, for 1-phenylpropyne, the thermodynamic regioselectivity was found to be greater than the kinetic regioselectivity. The regioselectivity was found to be invariant from -6 to 45°C in the addition of both 4-methyl-2-pentyne and 2-hexyne to Cp2(THF)Zr=NAr. However, a significant erosion of regioselectivity was observed when 2-hexyne and 4-methyl-2-pentyne were catalytically hydroaminated by Cp2Zr(NHAr)2 at 120°C. A kinetic study of the catalytic reaction suggested that the reason for this erosion was that the protonation step in the catalytic cycle (k3[amine]) was slower than the cycloreversion of the stereoisomeric metallacycles to alkyne and Cp2Zr=NAr (k-2) (the step that leads to regioequilibration). Because the protonation is selective for the metallacycle in which the smaller substituent is located at the position adjacent to the metal center, it counters the regioselectivity of the cycloaddition. This was an unexpected result because (1) an earlier study showed that k3 [amine] was larger than k-2 for the addition of diphenylacetylene to Cp2Zr=NR at both 25°C and the catalytic reaction temperature (95°C in this case) and (2) in the present work, it was demonstrated that k3 [amine] was also larger than k-2 for dialkylacetylenes at 25°C. It was concluded that the relative magnitudes of the rate constants k3 (protonation) and k-2 (reversion) must vary with temperature more dramatically in the dialkylacetylene + Cp2Zr=NR reaction than in the diarylacetylene + Cp2Zr=NR reaction. This was confirmed by direct competition experiments carried out at 25, 60, and 100°C. We believe that the cycloreversion step k-2 is characterized by both a larger ΔH? and a larger ΔS? than protonation because the former is a unimolecular and the latter a bimolecular reaction.

Dehydration of 4-methylpentan-2-ol over lanthanum and cerium oxides

Auroux,Artizzu,Ferino,Monaci,Rombi,Solinas,Petrini

, p. 2619 - 2624 (1996)

Lanthanum and cerium oxides have been tested for the title reaction at 623 K and atmospheric pressure in a flow reactor. Lanthanum oxide (prepared from the corresponding nitrate) gives mainly 4-methylpent-1-ene (80% of the products). Similar results are observed with cerium oxide obtained from the corresponding hydroxide, whereas cerium oxide prepared from nitrate is less selective towards alk-1-enes. In addition to dehydration, dehydrogenation to 4-methylpentan-2-one is also observed to a limited extent for all the catalysts. Information on the acid-base properties of the samples was obtained by adsorption microcalorimetry of ammonia and carbon dioxide and correlated to reaction selectivities. Possible changes in the oxidation state of cerium ions due to the reaction atmosphere are considered. The present results are compared with former data for zirconia catalysts. Modification of cerium oxide via immersion in NaOH solution does not appear to be useful for improving alk-1-ene selectivity.

The mechanism and kinetics of methyl isobutyl ketone synthesis from acetone over ion-exchanged hydroxyapatite

Ho, Christopher R.,Zheng, Steven,Shylesh, Sankaranarayanapillai,Bell, Alexis T.

, p. 174 - 183 (2018)

The synthesis of methyl isobutyl ketone (MIBK) can be carried out by the condensation of acetone in the presence of hydrogen over a supported metal catalyst. Previous studies have shown that hydroxyapatite is an excellent catalyst for condensation reactions. The present investigation was undertaken in order to elucidate the reaction mechanism and site requirements for acetone coupling to MIBK over a physical mixture of hydroxyapatite and Pd/SiO2. The reaction is found to proceed by consecutive aldol addition to form diacetone alcohol (DAA), dehydration of DAA to mesityl oxide (MO), and hydrogenation of MO to MIBK. The products formed by feeding DAA and MO reveal that aldol addition of acetone is rapid and reversible, and that the subsequent dehydration of DAA is rate-limiting. Pyridine and CO2 titration show that aldol dehydration occurs over basic sites via an E1cB mechanism. A series of cation-substituted hydroxyapatite samples were prepared by ion-exchange to further investigate the role of acid-base strength on catalyst performance. Characterization of these samples by PXRD, BET, ICP-OES, XPS, CO2-TPD, and Raman spectroscopy demonstrated that the exchange procedure used does not affect the bulk properties of hydroxyapatite. DFT calculations reveal that in addition to affecting the Lewis acidity/basicity of the support, the size of the cation plays a significant role in the chemistry: cations that are too large (Ba2+) or too small (Mg2+) adversely affect reaction rates due to excessive stabilization of intermediate species. Strontium-exchanged hydroxyapatite was found to be the most active catalyst because it promoted α-hydrogen abstraction and C–O bond cleavage of DAA efficiently.

-

De Puy

, p. 33,41 (1968)

-

Catalytic Hydration of Alkynes with Platinum(II) Complexes

Hartman, J. W.,Hiscox, W. C.,Jennings, P. W.

, p. 7613 - 7614 (1993)

-

-

Baum,K.

, p. 7083 - 7089 (1968)

-

-

Adkins,Kutz,Coffman

, p. 3212,3217 (1930)

-

-

Davis,Woodgate

, p. 65 (1966)

-

Petrow,Kupin

, p. 3153; engl.Ausg.S.3122 (1959)

Effect of metal modification of titania and hydrogen co-feeding on the reaction pathways and catalytic stability in the acetone aldol condensation

Quesada,Faba,Díaz, Eva,Ordó?ez, Salvador

, p. 133 - 144 (2019)

A stable performance of TiO2 catalysts for gas-phase acetone aldol condensation was observed when reduced metals were added (Pt or Ni, 1.5 wt%) and the reactions were conducted in presence of hydrogen. In both cases, the resulting metal-loaded catalysts are stable for 10 h, whereas continuous deactivation is observed for the parent TiO2 catalyst (573 K). Both the activation of the H2 molecule by metal nanoparticles and the change of the catalytic surface by metal insertion (in the case of Ni-loaded catalyst) enable suppressing oligomerization (by hindering enolates formation) and the strong adsorption of intermediates (by decreasing the concentration of high-strength acid-basic active sites), respectively. More interestingly, these metals allow to tune the selectivity of the reaction. Indeed, the Ni-loaded titania catalyst is highly selective for the synthesis of α,β-unsaturated ketones (selectivity to unsaturated C6 and C9 species >98%, at ~12% acetone conversion), whereas the Pt-loaded one is highly selective to the formation of saturated C6 and C9 ketones (MIBK and DIBK, with selectivities >95% at ~42% acetone conversion). The catalytic activity and stability of the two materials (Ni/TiO2 and Pt/TiO2) in both absence and presence of H2 are compared between them and with those of the parent TiO2. The results obtained by the reaction gas-phase analysis are supplemented through different solid characterization techniques (i.e., CO2-TPD and NH3-TPD, HRTEM, XPS, TPO, and DRIFTS).

-

Fahey,Lee

, p. 2124 (1968)

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Regiospecific solvent-free transfer hydrogenation of α,β-unsaturated carbonyl compounds catalyzed by a cationic ruthenium(II) compound

Naskar, Sipra,Bhattacharjee, Manish

, p. 465 - 467 (2007)

[(PPh3)2Ru(CH3CN)3Cl][BPh4] has been found to catalyze the selective reduction of double bonds in α,β-unsaturated ketones with high conversions when formic acid is the hydrogen donor.

An efficient bifunctional catalyst of TiO2 coating and supported Pd on cordierite for one-pot synthesis of MIBK from acetone

Zhang, Shoude,Wu, Pengcheng,Yang, Lequn,Zhou, Yonghua,Zhong, Hong

, p. 61 - 64 (2015)

We report here an efficient bifunctional catalyst of TiO2 coating and supported Pd on cordierite (T500/Cor&Pd/Cor) for one-pot synthesis of MIBK from acetone. The obtained 75% MIBK selectivity at 60% acetone conversion was the best performance ever reported for metal oxide based catalyst, without obvious deactivation for at least 12 h on stream. The superior performance of T500/Cor&Pd/Cor could be attributed to the dominant base sites and moderate acid sites on TiO2 coating caused by the nanoscale anatase crystallite, and its combination style of being physically mixed with Pd.

CONVERSION OF ALKANES BY THE ACTION OF ACYL HALIDES AND AlBr3 UNDER MILD CONDITIONS

Akhrem, I. S.,Orlinkov, A. V.,Mysov, E. I.,Enaleeva, R. Ya.,Vol'pin, M. E.

, (1983)

-

Bifunctionalized hollow nanospheres for the one-pot synthesis of methyl isobutyl ketone from acetone

Wang, Peng,Bai, Shiyang,Zhao, Jiao,Su, Panpan,Yang, Qihua,Li, Can

, p. 2390 - 2396 (2012)

Pd-doped propyl sulfonic acid-functionalized hollow nanospheres proved to be efficient bifunctionalized catalysts for the one-pot synthesis of methyl isobutyl ketone (MIBK) from acetone and hydrogen in liquid phase. These hollow nanospheres exhibited a higher activity than their bulk mesoporous counterparts (SBA-15 or FDU-12), mainly due to the short diffusion resistance of hollow nanospheres. Hollow nanospheres with silica frameworks showed higher activity and selectivity for MIBK than those with ethane-bridged frameworks, suggesting that hollow nanospheres with hydrophilic surface properties favor the formation of MIBK. This is probably due to the increased affinity of the hydrophilic surface towards acetone and its decreased affinity towards MIBK, which precludes deep condensation of MIBK with acetone. Under optimal conditions, up to 90 % selectivity for MIBK can be obtained with conversions of acetone as high as 43 %. This result is among the best reported so far for mesoporous silica-based catalysts. The control/fine-tuning of morphology and surface properties provides an efficient strategy for improving the catalytic performance of solid catalysts.

Intramolecular Activation of a N-Methyl C-H Bond by an Electron Rich Iridium Centre: a Novel Chemoselective Reduction Catalyst

Farnetti, Erica,Nardin, Giorgio,Graziani, Mauro

, p. 1264 - 1265 (1989)

The iridium complex > formed by intramolecular C-H oxidative addition, as shown by X-ray analysis, behaves as a chemoselective catalyst in hydrogen transfer reduction of α,β-unsaturated ketones to unsaturated alcohols.

One-step MIBK synthesis: A new process from 2-propanol

Di Cosimo,Torres,Apesteguia

, p. 114 - 123 (2002)

The one-step MIBK synthesis from 2-propanol was investigated as an alternative process to current conventional technology that produces MIBK from acetone. The reaction was studied at 473 K and atmospheric pressure using bifunctional Cu-base catalysts. Single MIOx, binary MIMIIOx, and Cu-containing CuMI(MII)Ox mixed oxides, where MI and MII are metal cations such as Mg2+, Al3+, or Ce3+, were obtained by thermal decomposition of precipitated precursors. The density and strength of surface basic sites were obtained by CO2 chemisorption and by temperature-programmed desorption (TPD) of CO2, whereas the acid site densities were measured by TPD of NH3. The MIBK synthesis reaction network involves consecutively the initial 2-propanol dehydrogenation to acetone, the aldol condensation of acetone to mesityl oxide, and the final hydrogenation of this compound to MIBK. Cu/SiO2 promoted 2-propanol dehydrogenation to acetone but did not form any C6 condensation products. When copper was supported on protonic HY zeolite, 2-propanol was essentially dehydrated to propylene and the formation of acetone was negligible. Bifunctional Cu-base catalysts were active and selective for MIBK synthesis. The highest MIBK formation rates were obtained on Cu-base solids containing a high density of medium-strength Bronsted base-weak Lewis acid pair sites for promoting the acetone aldol condensation step. CuMg10Al7Ox was the best catalyst because it contained in intimate contact highly dispersed Cu0 crystallites with proper Al3+ Lewis sites and Mg+2-O2- basic pairs and efficiently combines the active sites required for consecutive reactions leading to MIBK. Catalysts containing strongly basic O2- sites, such as CuMg10Ox and CuMg10Ce2Ox, presented lower condensation rates because isolated O2- hindered stabilization of anionic intermediates for acetone condensation. The effect that the reacting atmosphere (N2 or H2) has on catalyst activity and selectivity was investigated on CuMg10Al7Ox. It was found that the catalyst activity is enhanced in N2, but for a given 2-propanol conversion the selectivity for C6 aldol condensation products is higher in hydrogen. MIBK yields as high as 25% were achieved in comparison to the 30% typically obtained in current commercial high-pressure processes from acetone.

The hydroxyl radical reaction rate constant and products of 3,5-dimethyl-1-hexyn-3-ol

Wells

, p. 534 - 544 (2004)

A bimolecular rate constant, κDHO, of (29 ± 9) × 10-12 cm3 molecule-1 s-1 was measured using the relative rate technique for the reaction of the hydroxyl radical (OH) with 3,5-dimethyl-1-hexyn-3-ol (DHO, HC≡CC(OH)(CH3)CH2CH(CH3 2) at (297 ± 3) K and 1 atm total pressure. To more clearly define DHO's indoor environment degradation mechanism, the products of the DHO + OH reaction were also investigated. The positively identified DHO/OH reaction products were acetone ((CH3 2C=O), 3-butyne-2-one (3B2O, HC≡CC(=O)(CH3)), 2-methyl-propanal (2MP, H(O=)CCH(CH3)2), 4-methyl-2-pentanone (MIBK, CH3C(=O CH2 CH(CH3)2), ethanedial (GLY, HC(=O C(=O)H), 2-oxopropanal (MGLY, CH3C(=O)C(=O)H), and 2,3-butanedione (23BD, CH3C(=O)C(=O)CH3). The yields of 3B2O and MIBK from the DHO/OH reaction were (8.4 ± 0.3) and (26 ± 2)%, respectively. The use of derivatizing agents O-(2,3,4,5,6-pentalfluorobenzyl)hydroxylamine (PFBHA) and N,O-bis (trimethylsilyl)trifluoroacetamide (BSTFA) clearly indicated that several other reaction products were formed. The elucidation of these other reaction products was facilitated by mass spectrometry of the derivatized reaction products coupled with plausible DHO/OH reaction mechanisms based on previously published volatile organic compound/OH gas-phase reaction mechanisms.

-

Sato,T. et al.

, p. 1176 - 1179 (1972)

-

One-step synthesis of methyl isobutyl ketone from acetone and hydrogen over Cu-on-MgO catalysts

Chikan, Viktor,Molnar, Arpad,Balazsik, Katalin

, p. 134 - 143 (1999)

The one-step synthesis of methyl isobutyl ketone (MIBK) from acetone and hydrogen over Cu-on-MgO catalysts was studied at atmospheric pressure in a fixed bed continuous flow reactor. Catalysts with various copper loadings were prepared by impregnation and coprecipitation and characterized by BET and Cu(O) surface area measurements, XRD, SAXS, thermal analysis, and basicity measurements. A 3.46% Cu-on-MgO prepared by coprecipitation, calcined at 723 K for 4 h, and pretreated in hydrogen (673 K, 1 h) showed high and stable activity and selectivity in the production of MIBK. Under the best conditions (553 K reaction temperature, 15% molar excess of hydrogen to acetone, and 1920 ml h-1 gcat-1 space velocity) MIBK is formed in 45-48% yield (60-80% conversion and 60-75% selectivity) over a period of 24 h-on-stream. The results of deuterium labeling studies point to metallic sites catalyzing deuterium exchange and basic sites catalyzing dimerization of acetone, leading eventually to MIBK with high deuterium content. A comparison of deuterium contents of acetone, mesityl oxide (MO), and MIBK shows that the surface deuterium pool is highly diluted with hydrogen, formed during the exchange process. Deuterium incorporation during the saturation of the carbon-carbon double bond of MO to form MIBK, therefore, is less than expected. Formation of diisobutyl ketone with very low deuterium content is suggested to result from the involvement of strongly bound surface intermediates with long residence time not allowing exchange process.

Multifunctional catalysis by Pd@MIL-101: One-step synthesis of methyl isobutyl ketone over palladium nanoparticles deposited on a metal-organic framework

Pan, Yingyi,Yuan, Bizhen,Li, Yingwei,He, Dehua

, p. 2280 - 2282 (2010)

Palladium nanoparticles deposited on a chromium terephthalate MIL-101 is a highly efficient multifunctional catalyst for the one-step synthesis of methyl isobutyl ketone, with significantly higher activity than palladium on traditional materials, such as metal oxides and zeolites.

1,3-Dichloro-5,5-dimethylhydantoin (DCDMH) as a new oxidizing agent for the facile and selective oxidation of oximes to their carbonyl compounds

Khazaei, Ardeshir,Manesh, Abbas Amini

, p. 1017 - 1020 (2005)

Oximes are converted to the parent carbonyl compounds in good yields when treated with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) (1). An optimized procedure has been developed; the simple work-up minimizes loss of product and oximes have been selectively oxidized in the presence of alcohols and alkenes.

-

Davis,Woodgate

, p. 2006 (1966)

-

Copper(I)-catalysed Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds by Lithium Aluminium Hydride

Tsuda, Tetsuo,Fujii, Tomoyuki,Kawasaki, Kaoru,Saegusa, Takeo

, p. 1013 - 1014 (1980)

CuI catalyses an efficient conjugate reduction of α,β-unsaturated carbonyl compounds by LiAlH4 in the presence of hexamethylphosphoric triamide at -78 degC.

-

Renfrow

, p. 146 (1944)

-

Oxidative cleavage of oximes with silica-gel-supported chromic acid in nonaqueous media

Ali, Mohammed Hashmat,Greene, Stacie,Wiggin, Candace J.,Khan, Saira

, p. 1761 - 1767 (2006)

A simple procedure for a clean and high-yielding oxidative deoximation of benzaldoximes and ketoximes using a silica-gel-supported chromic acid reagent has been developed. This solid-supported reagent allows us to carry out this reaction in nonaqueous dichloromethane reaction media. Copyright Taylor & Francis Group, LLC.

-

Hightower,L.E. et al.

, p. 1881 - 1886 (1970)

-

Catalytic synthesis of cumene from benzene and acetone

Shutkina,Ponomareva,Ivanova

, p. 20 - 26 (2013)

The reaction of benzene hydroalkylation with acetone on bifunctional catalysts has been studied and the principal features of the process have been revealed, wherein the catalysts contain a copper oxide-copper chromite binary system as a hydrogenating component and BEA, MOR, FAU, or MFI zeolite as an alkylating component. It has been found that the use of the catalyst based on the mixed copper-chromium oxide and mordenite, running the process at 150 C and 3 MPa, and feedstock dilution with benzene (C6H6: C 3H6O = 9: 1) facilitate increasing of the yield of cumene as a main product.

Synthesis of Acetone-Derived C6, C9, and C12Carbon Scaffolds for Chemical and Fuel Applications

Moore, Cameron M.,Jenkins, Rhodri W.,Janicke, Michael T.,Kubic, William L.,Polikarpov, Evgueni,Semelsberger, Troy A.,Sutton, Andrew D.

, p. 3382 - 3386 (2016)

A simple, inexpensive catalyst system (Amberlyst 15 and Ni/SiO2–Al2O3) is described for the upgrading of acetone to a range of chemicals and potential fuels. Stepwise hydrodeoxygenation of the produced ketones can yield branched alcohols, alkenes, and alkanes. An analysis of these products is provided, which demonstrates that this approach can provide a product profile of valuable bioproducts and potential biofuels.

-

Rastetter,Frost

, p. 3353,3354,3355 (1979)

-

DILITHIO ACETOACETATE AS AN ACETONE ENOLATE EQUIVALENT

Kjonaas, Richard A.,Patel, Dhiren D.

, p. 5467 - 5468 (1984)

Dilithio acetoacetate, which can be generated from acetoacetic acid and n-butyllithium, undergoes alkylation followed by facile decarboxylation to give methyl ketones.

Nickel catalyzed silane reductions of α, β - Unsaturated ketones and nitriles

Boudjouk, Philip,Choi, Seok-Bong,Hauck, Brian J.,Rajkumar, Amirthini B.

, p. 3951 - 3952 (1998)

Activated nickel, produced by the ultrasound-promoted reduction of nickel iodide with lithium, catalyzes the 1,4 addition of phenylsilane to α, β-unsaturated ketones and α, β-unsaturated nitriles to give, after hydrolysis, high yields of the products of 1, 2 hydrogenation.

Aerobic oxidation of alcohols using a novel combination of N-hydroxyphthalimide (NHPI) and CuBr

Yang, Gang,Wang, Lianyue,Li, Jun,Zhang, Yi,Dong, Xiaoli,Lv, Ying,Gao, Shuang

, p. 775 - 783 (2012)

A new catalytic system for oxidation of alcohols with oxygen by N-hydroxyphthalimide (NHPI) combined with CuBr has been developed. The reaction results showed that this catalytic system can effectively catalyze the oxidation of alcohols to the corresponding carboxylic acids or ketones. We obtained 100% selectivity for acetophenone at 94.2% conversion of phenylethanol at 75 °C for 20 h. A mechanism of oxidation of alcohols catalyzed by NHPI/CuBr was proposed. Springer Science+Business Media B.V. 2011.

Study on the selective hydrogenation of isophorone

Xu, Lei,Sun, Shaoyin,Zhang, Xing,Gao, Haofei,Wang, Wei

, p. 4465 - 4471 (2021)

3,3,5-Trimethylcyclohexanone (TMCH) is an important pharmaceutical intermediate and organic solvent, which has important industrial significance. The selective hydrogenation of isophorone was studied over noble metal (Pd/C, Pt/C, Ir/C, Ru/C, Pd/SiO2, Pt/SiO2, Ir/SiO2, Ru/SiO2), and non-noble metal (RANEY Ni, RANEY Co, RANEY Cu, RANEY Fe, Ni/SiO2, Co/SiO2, Cu/SiO2, Fe/SiO2) catalysts and using solvent-free and solvent based synthesis. The results show that the solvent has an important effect on the selectivity of TMCH. The selective hydrogenation of isophorone to TMCH can be influenced by the tetrahydrofuran solvent. The conversion of isophorone is 100%, and the yield of 3,3,5-trimethylcyclohexanone is 98.1% under RANEY Ni and THF. The method was applied to the selective hydrogenation of isopropylidene acetone, benzylidene acetone and 6-methyl-5-ene-2-heptanone. The structures of the hydrogenation product target (4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one) were characterized using 1H-NMR and 13C-NMR. The yields of 4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one were 97.2%, 98.5% and 98.2%, respectively. The production cost can be reduced by using RANEY metal instead of noble metal palladium. This method has good application prospects. This journal is

-

Roscher

, p. 474 (1971)

-

Hobbs,Houston

, p. 1254 (1954)

Dendrimer-Palladium complex catalyzed oxidation of terminal alkenes to methyl ketones

Zweni, Pumza P.,Alper, Howard

, p. 849 - 854 (2004)

Silica-supported polyamidoamine (PAMAM) dendrimers with different spacer lengths were prepared. After the introduction of diphenylphosphino groups, complexation to dibenzylidenepalladium(0) gave the desired silica-supported dendrimer - palladium catalyst complexes G0 to G4-C2-Pd. These catalysts showed activity towards the oxidation of terminal alkenes to methyl ketones. A dependence of catalytic activity on the spacer length of the diamine in PAMAM was observed.

An exceptionally rapid and selective hydrogenation of 2-cyclohexen-1-one in supercritical carbon dioxide

Chatterjee, Maya,Yokoyama, Toshirou,Kawanami, Hajime,Sato, Masahiro,Suzuki, Toshishige

, p. 701 - 703 (2009)

Selective hydrogenation of 2-cyclohexen-1-one over Pt-MCM-41 proceeds at a very high rate and produces cyclohexanone with selectivity of 100% in a batch reactor; a marked increase in the reaction rate (TOF) from 2283 min-1 to 5051 min-1 is observed on increasing the pressure from 7 MPa to 14 MPa at 40°C. The Royal Society of Chemistry 2009.

Pd supported on ZnII-CrIII mixed oxide as a catalyst for one-step synthesis of methyl isobutyl ketone

Al-Wadaani, Fahd,Kozhevnikova, Elena F.,Kozhevnikov, Ivan V.

, p. 199 - 205 (2008)

Pd metal supported on ZnII-CrIII mixed oxide is an efficient bifunctional catalyst for the one-step synthesis of methyl isobutyl ketone (MIBK) from acetone and H2 in the gas and liquid phases. The reaction involves acid-catalysed condensation of acetone to mesityl oxide, followed by its hydrogenation to MIBK. Diisobutyl ketone (DIBK) is a useful byproduct in this process. Zn-Cr oxides (Zn/Cr = 20:1-1:30) are prepared by coprecipitation of ZnII and CrIII hydroxides. The texture and acid properties (i.e., the nature, density, and strength of acid sites) of Zn-Cr oxides, as well as the Pd dispersion in the catalysts, are thoroughly characterised. For both the continuous gas-phase process and the batch liquid-phase process, the preferred catalyst formulation is 0.3 wt% Pd on the amorphous Zn-Cr (1:1) oxide (SBET = 132 m2 / g) having Lewis acid sites (1.2 mmol/g density) with an enthalpy of NH3 adsorption of - 155 kJ / mol. Both processes produce MIBK with a selectivity of 70-78% and 90% MIBK + DIBK total selectivity at 38-40% acetone conversion. Evidence is provided that hydrogenation of mesityl oxide to MIBK is the rate-limiting step in the gas-phase process.

Selective Catalytic Oxidation of Organic Compounds by Nitrogen Dioxide

Nyarady, Stefan A.,Sievers, Robert E.

, p. 3726 - 3727 (1985)

-

The application of palladium and zeolite incorporated chip-based microreactors

Truter,Ordomsky,Schouten,Nijhuis

, p. 72 - 82 (2016)

The ability to successfully incorporate heterogeneous catalysts into chip-microreactors is demonstrated in the application of a Pd/ZSM-5 and Pd/silicalite chip-based microreactor for the synthesis of methyl-iso-ketone (MIBK) and the hydrogenation of 3-methyl-1-pentyn-3-ol. The bifunctional Pd/ZSM-5 chip-microreactor provides a high selectivity (>90%) to MIBK due to the incorporation of palladium and high Br?nsted acidity while demonstrating the ability to regenerate and reuse the Pd/ZSM-5 chip-microreactor. The Pd/silicalite chip-microreactor illustrated the advantage of improved control of residence time in the microreactor to obtain high alkene yields. In addition, the design of chip-holders which are operable at high temperature, pressure and have a high chemical resistance further extend the operability of chip-based microreactors for use in the special chemical industry.

Merging N-Hydroxyphthalimide into Metal-Organic Frameworks for Highly Efficient and Environmentally Benign Aerobic Oxidation

Wang, Man,Liang, Gan,Wang, Yunhao,Fan, Tao,Yuan, Baoling,Liu, Mingxian,Yin, Ying,Li, Liangchun

supporting information, p. 9674 - 9685 (2021/06/09)

Two highly efficient metal-organic framework catalysts TJU-68-NHPI and TJU-68-NDHPI have been successfully synthesized through solvothermal reactions of which the frameworks are merged with N-hydroxyphthalimide (NHPI) units, resulting in the decoration of pore surfaces with highly active nitroxyl catalytic sites. When t-butyl nitrite (TBN) is used as co-catalyst, the as-synthesized MOFs are demonstrated to be highly efficient and recyclable catalysts for a novel three-phase heterogeneous oxidation of activated C?H bond of primary and secondary alcohols, and benzyl compounds under mild conditions. Based on the high efficiency and selectivity, an environmentally benign system with good sustainability, mild conditions, simple work-up procedure has been established for practical oxidation of a wide range of substrates.

Visible-light photocatalytic selective oxidation of C(sp3)-H bonds by anion-cation dual-metal-site nanoscale localized carbon nitride

Duan, Limei,Li, Peihe,Li, Wanfei,Liu, Jinghai,Liu, Ying,Liu, Zhifei,Lu, Ye,Sarina, Sarina,Wang, Jinghui,Wang, Yin,Wang, Yingying,Zhu, Huaiyong

, p. 4429 - 4438 (2021/07/12)

Selective oxidation of C(sp3)-H bonds to carbonyl groups by abstracting H with a photoinduced highly active oxygen radical is an effective method used to give high value products. Here, we report a heterogeneous photocatalytic alkanes C-H bonds oxidation method under the irradiation of visible light (λ= 425 nm) at ambient temperature using an anion-cation dual-metal-site modulated carbon nitride. The optimized cation (C) of Fe3+or Ni2+, with an anion (A) of phosphotungstate (PW123?) constitutes the nanoscale dual-metal-site (DMS). With a Fe-PW12dual-metal-site as a model (FePW), we demonstrate a A-C DMS nanoscale localized carbon nitride (A-C/g-C3N4) exhibiting a highly enhanced photocatalytic activity with a high product yield (86% conversion), selectivity (up to 99%), and a wide functional group tolerance (52 examples). The carbon nitride performs the roles of both the visible light response, and improves the selectivity for the oxidation of C(sp3)-H bonds to carbonyl groups, along with the function of A-C DMS in promoting product yield. Mechanistic studies indicate that this reaction follows a radical pathway catalyzed by a photogenerated electron and hole on A-C/g-C3N4that is mediated by thetBuO˙ andtBuOO˙ radicals. Notably, a 10 g scale reaction was successfully achieved for alkane photocatalytic oxidation to the corresponding product with a good yield (80% conversion), and high selectivity (95%) under natural sunlight at ambient temperature. In addition, this A-C/g-C3N4photocatalyst is highly robust and can be reused at least six times and the activity is maintained.

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Ye, Yang,Ma, Guobin,Yao, Ken,Gong, Hegui

supporting information, p. 1625 - 1628 (2021/01/18)

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

PhIO-Mediated oxidative dethioacetalization/dethioketalization under water-free conditions

Du, Yunfei,Ouyang, Yaxin,Wang, Xi,Wang, Xiaofan,Yu, Zhenyang,Zhao, Bingyue,Zhao, Kang

, p. 48 - 65 (2021/06/16)

Treatment of thioacetals and thioketals with iodosobenzene in anhydrous DCM conveniently afforded the corresponding carbonyl compounds in high yields under water-free conditions. The mechanistic studies indicate that this dethioacetalization/dethioketalization process does not need water and the oxygen of the carbonyl products comes from the hypervalent iodine reagent.

Chemoselective and Site-Selective Reductions Catalyzed by a Supramolecular Host and a Pyridine-Borane Cofactor

Morimoto, Mariko,Cao, Wendy,Bergman, Robert G.,Raymond, Kenneth N.,Toste, F. Dean

supporting information, p. 2108 - 2114 (2021/02/06)

Supramolecular catalysts emulate the mechanism of enzymes to achieve large rate accelerations and precise selectivity under mild and aqueous conditions. While significant strides have been made in the supramolecular host-promoted synthesis of small molecules, applications of this reactivity to chemoselective and site-selective modification of complex biomolecules remain virtually unexplored. We report here a supramolecular system where coencapsulation of pyridine-borane with a variety of molecules including enones, ketones, aldehydes, oximes, hydrazones, and imines effects efficient reductions under basic aqueous conditions. Upon subjecting unprotected lysine to the host-mediated reductive amination conditions, we observed excellent ?-selectivity, indicating that differential guest binding within the same molecule is possible without sacrificing reactivity. Inspired by the post-translational modification of complex biomolecules by enzymatic systems, we then applied this supramolecular reaction to the site-selective labeling of a single lysine residue in an 11-amino acid peptide chain and human insulin.

Process route upstream and downstream products

Process route

4-Methyl-1-pentene
691-37-2,25068-26-2

4-Methyl-1-pentene

4-methylpent-2-enal
5362-56-1

4-methylpent-2-enal

isocaproic aldehyde
1119-16-0

isocaproic aldehyde

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
With dichloro bis(acetonitrile) palladium(II); oxygen; p-benzoquinone; copper(l) chloride; In water; tert-butyl alcohol; at 40 ℃; for 6h; under 760.051 Torr; regioselective reaction;
50 %Spectr.
24 %Spectr.
18 %Spectr.
hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

2-(1-hydroxy-1,3-dimethyl-butyl)-2-methyl-succinic acid dimethyl ester

2-(1-hydroxy-1,3-dimethyl-butyl)-2-methyl-succinic acid dimethyl ester

2-methylbutanedioic acid
498-21-5,636-60-2

2-methylbutanedioic acid

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

4-methyl-pent-3-en-2-one
141-79-7

4-methyl-pent-3-en-2-one

2-Methyl-1-butene
563-46-2

2-Methyl-1-butene

5-Methyl-2-hexanone
110-12-3

5-Methyl-2-hexanone

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
With CH3COCl*2AlBr3; In neat (no solvent); at 20 ℃; for 0.5h; Product distribution; other n-alkanes C6-C12, C18, other reagent;
3,5-Dichloro-phenol; compound with 4-methyl-pentan-2-one

3,5-Dichloro-phenol; compound with 4-methyl-pentan-2-one

3,5-dichlorophenol
591-35-5

3,5-dichlorophenol

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
In cyclohexane; at 24.9 ℃; Equilibrium constant;
3,5-Dichloro-phenol; compound with 4-methyl-pentan-2-one

3,5-Dichloro-phenol; compound with 4-methyl-pentan-2-one

3,5-dichlorophenol
591-35-5

3,5-dichlorophenol

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
In cyclohexane; at 24.9 ℃; Equilibrium constant;
(C<sub>4</sub>H<sub>9</sub>)3SnOCH(CH<sub>3</sub>)C<sub>3</sub>H<sub>4</sub>CH<sub>3</sub>

(C4H9)3SnOCH(CH3)C3H4CH3

n-hexan-2-one
591-78-6

n-hexan-2-one

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
With t-C4H9OOC4H9-t; at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COCH3, n-C4H9COCH3 = 87:3:10;
With t-C4H9OOC4H9-t; at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COCH3, n-C4H9COCH3 = 87:3:10;
(C<sub>4</sub>H<sub>9</sub>)3SnOCH(CH<sub>3</sub>)C<sub>3</sub>H<sub>4</sub>CH<sub>3</sub>

(C4H9)3SnOCH(CH3)C3H4CH3

n-hexan-2-one
591-78-6

n-hexan-2-one

1-(2-methyl-cyclopropyl)-ethanone
930-56-3

1-(2-methyl-cyclopropyl)-ethanone

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
With t-C4H9OOC4H9-t; at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COCH3, n-C4H9COCH3 = 91:1:8; ratio of cis and trans isomer = 1:2;
With t-C4H9OOC4H9-t; at 130-140°C; proportion of c-C3H4(CH3)COCH3, i-C4H9COCH3, n-C4H9COCH3 = 91:1:8; ratio of cis and trans isomer = 1:2;
acetaldehyde
75-07-0,9002-91-9

acetaldehyde

acetone
67-64-1

acetone

3-penten-2-one
625-33-2

3-penten-2-one

2-Pentanone
107-87-9

2-Pentanone

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
With hydrogen; 0.5% Pd/C; caustic solution; at 90 ℃; under 12751.3 Torr; Pro-PAK Product distribution / selectivity;
acetaldehyde; acetone; With hydrogen; 0.5% Pd/C; caustic solution; at 110 ℃; under 12751.3 Torr; Pro-PAK
0.1 % Pd/C; caustic solution; at 110 ℃; under 12751.3 Torr; Product distribution / selectivity;
Methyl isobutyl carbinol
108-11-2,72847-31-5

Methyl isobutyl carbinol

4-methyl-2-pentene
4461-48-7

4-methyl-2-pentene

4-Methyl-1-pentene
691-37-2,25068-26-2

4-Methyl-1-pentene

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

Conditions
Conditions Yield
magnesium oxide; at 313.9 ℃; Mechanism; Product distribution; product distribution depends on temperature and pretreatment of catalyst(H2, or O2); further temperatures, further catalyst CaO;
cerium(IV) oxide; copper(II) oxide; In gas; at 274.9 ℃; Product distribution; Thermodynamic data; Kinetics; E(excit.), var. other lanthanide catalysts, var. temperatures;
zirconium(IV) oxide; at 339.9 ℃; Product distribution; various catalysts, temperatures;
With lanthanum(III) oxide; at 359.9 ℃; Product distribution; further reagent: cerium oxide; various temp.;
cerium(IV) oxide; lanthanum(III) oxide; at 424.85 ℃; for 1h; under 760 Torr; Further Variations:; Catalysts; reaction time; Product distribution;
zirconia aerogel; at 329.84 ℃; Further Variations:; Catalysts; Product distribution;
With zirconium(IV) oxide; at 320 ℃;
acetone
67-64-1

acetone

Methyl isobutyl carbinol
108-11-2,72847-31-5

Methyl isobutyl carbinol

propane
74-98-6

propane

2-Methylpentane
107-83-5

2-Methylpentane

2,6-dimethyl-4-heptanol
108-82-7

2,6-dimethyl-4-heptanol

diisobutyl ketone
108-83-8

diisobutyl ketone

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

Conditions
Conditions Yield
With hydrogen; In neat (no solvent); at 200 ℃; under 2250.23 Torr; Inert atmosphere;

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