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Cas Database

141-79-7

141-79-7

Identification

  • Product Name:3-Penten-2-one,4-methyl-

  • CAS Number: 141-79-7

  • EINECS:205-502-5

  • Molecular Weight:98.1448

  • Molecular Formula: C6H10O

  • HS Code:2914190090

  • Mol File:141-79-7.mol

Synonyms:2,2-Dimethylvinylmethyl ketone;2-Methyl-2-penten-4-one;2-Methyl-4-oxo-2-pentene;4-Methyl-3-pentene-2-one;Isobutenyl methyl ketone;Isopropylideneacetone;Methyl 2,2-dimethylvinyl ketone;Methyl2-methyl-1-propenyl ketone;Methyl isobutenyl ketone;NSC 38717;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes: Xn:Harmful;

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH302 Harmful if swallowed H312 Harmful in contact with skin H332 Harmful if inhaled

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. 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. Give a slurry of activated charcoal in water to drink. Refer for medical attention . Inhalation causes irritation of nose and throat, headache, dizziness, difficult breathing. Contact with liquid or concentrated vapor causes severe eye irritation. Liquid irritates skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999) Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... Anticipate seizures and treat if necessary ... For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. /Turpentine, terpenes, and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use dry chemical, foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool. Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (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: self-contained breathing apparatus. Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Eliminate all ignition sources. Stop or control the leak, if it can be done without undue risk. Use appropriate foam to blanket release and suppress vapors. Approach release from upwind. Absorb in noncombustible material for proper disposal.

  • 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. Cool. Keep in the dark.Fireproof. Separated from strong oxidants. Cool. Keep in the dark.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (40 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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Relevant articles and documentsAll total 159 Articles be found

CYCLO-ELIMINATION OF SILYL AND SULPHOXIDE GROUPS IN COMPETITION WITH THE CONVENTIONAL CYCLO-ELIMINATION OF SULPHOXIDES

Fleming, Ian,Perry, David A.

, p. 5095 - 5096 (1981)

The β-silylsulphoxides (2 and 4) undergo a fast syn-elimination to give the alkene (3) and the alkyne (6), respectively; however, when there is a hydrogen α to the silyl group, only hydrogen is lost, and the products are β-silylenones.

Grob,Spaar

, p. 1439 (1969)

Highly Stereoselective Synthesis of α,β-Unsaturated Ketones by CeCl3 Mediated Addition of Grignard Reagents to β-Enamino Ketones

Bartoli, Giuseppe,Cimarelli, Cristina,Marcantoni, Enrico,Palmieri, Gianni,Petrini, Marino

, p. 715 - 716 (1994)

A stereoselective synthesis of α,β-unsaturated ketones by direct addition of Grignard reagents to β-enamino ketones, mediated by dry cerium(III) chloride, is described and a trans relationship between the introduced framework and the carbonyl group is predominantly observed.

-

Ciabattoni,Kocienski

, p. 6534 (1969)

-

Fluoride adducts of niobium(V): Activation reactions and alkene polymerizations

Hayatifar, Mohammad,Marchetti, Fabio,Pampaloni, Guido,Patil, Yogesh,Raspolli Galletti, Anna Maria

, p. 214 - 218 (2013)

Fluoride coordination derivatives of niobium(V) were tested for their activation capabilities with respect to acetone and to olefins. Activation of acetone (formation of mesityloxide) was observed with NbF4(OMe). Several fluoride coordination derivatives of niobium(V) of different nature (neutral or ionic) and nuclearity, i.e. NbF5L [L = Et2O, 4, thf, 5 (thf is tetrahydrofuran), MeOH, 6, EtOH, 7], (NbF4L 2)(NbF6) [L = dmf, 8 (dmf is dimethylformamide), dme, 9 (dme is dimethoxyethane)], (NbF4L4)(NbF6) [L = thf, 10, Et2O, 11, MeCN, 12], [S(NMe)3][NbF6], 13, NbF4OMe, 1, NbF4OPh, 3), NbF3(OPh) 2, 14, NbF2(OPh)3, 15 and NbF 2(OEt)3, 16, promoted the polymerization of ethylene using AlMe3-depleted methylaluminoxane as cocatalyst. Highly linear polyethylene was obtained. Compound 3, upon activation with methylaluminoxane, promoted ring-opening metathesis polymerization (ROMP) of norbornene, affording polymers with a slight excess of trans content.

-

Currie

, p. 1061 (1913)

-

Tricyanomethane and Its Ketenimine Tautomer: Generation from Different Precursors and Analysis in Solution, Argon Matrix, and as a Single Crystal

Banert, Klaus,Chityala, Madhu,Hagedorn, Manfred,Beckers, Helmut,Stüker, Tony,Riedel, Sebastian,Rüffer, Tobias,Lang, Heinrich

, p. 9582 - 9586 (2017)

Solutions of azidomethylidenemalononitrile were photolyzed at low temperatures to produce the corresponding 2H-azirine and tricyanomethane, which were analyzed by low-temperature NMR spectroscopy. The latter product was also observed after short thermolysis of the azide precursor in solution whereas irradiation of the azide isolated in an argon matrix did not lead to tricyanomethane, but to unequivocal detection of the tautomeric ketenimine by IR spectroscopy for the first time. When the long-known “aquoethereal” greenish phase generated from potassium tricyanomethanide, dilute sulfuric acid, and diethyl ether was rapidly evaporated and sublimed, a mixture of hydronium tricyanomethanide and tricyanomethane was formed instead of the previously claimed ketenimine tautomer. Under special conditions of sublimation, single crystals of tricyanomethane could be isolated, which enabled the analysis of the molecular structure by X-ray diffraction.

INFRARED STUDY OF THE REACTIVITY OF ACETONE AND HEXACHLOROACETONE ADSORBED ON HAEMATITE

Busca, Guido,Lorenzelli, Vincenzo

, p. 2911 - 2920 (1982)

Infrared spectra of acetone adsorbed at beam temperature on α-Fe2O3 show that acetone can chemisorb on Lewis-acid sites and gives, at least partially, enolate anions; these, by aldolic condensation with molecules from the gas phase, produce a chemisorbed form of mesityl oxide.At 523 K acetate ions are formed.Two different forms of trichloroacetate ions are formed on the surface at beam temperature by the adsorption of hexachloroacetone and trichloroacetic acid.This behaviour indicates the presence of pairs of acid-base sites on the surface of haematite, and also shows that its surface hydroxy groups have a lower degree of nucleophilic character with respect to those of other oxides such as aluminas, SnO2 and alkaline-earth oxides.

Acetone condensation over CaO—SnO2 catalyst

Koklin,Hasyanova,Glukhov,Bogdan

, p. 488 - 490 (2017)

Aldol condensation of acetone was studied over solid base CaO—SnO2 catalyst in the 300—450 °C temperature range and at 15—75 atm pressure in a fixed-bed reactor. The main products are mesityl oxide and isophorone. The high stability of CaO—SnO2 catalyst performance was observed at pressure of 75 atm giving the acetone conversion of 36—41%. Increase in the temperature and pressure led to a simultaneous raise in acetone conversion. The maximum conversion of 41% was achieved at 400 °C, 75 atm and a flow rate of acetone of 8.1 g h–1 (g catalyst)–1.

Facile rearrangement of 3-oxoalkyl radicals is evident in low-temperature gas-phase oxidation of ketones

Scheer, Adam M.,Welz, Oliver,Sasaki, Darryl Y.,Osborn, David L.,Taatjes, Craig A.

, p. 14256 - 14265 (2013)

The pulsed photolytic chlorine-initiated oxidation of methyl-tert-butyl ketone (MTbuK), di-tert-butyl ketone (DTbuK), and a series of partially deuterated diethyl ketones (DEK) is studied in the gas phase at 8 Torr and 550-650 K. Products are monitored as a function of reaction time, mass, and photoionization energy using multiplexed photoionization mass spectrometry with tunable synchrotron ionizing radiation. The results establish that the primary 3-oxoalkyl radicals of those ketones, formed by abstraction of a hydrogen atom from the carbon atom in γ-position relative to the carbonyl oxygen, undergo a rapid rearrangement resulting in an effective 1,2-acyl group migration, similar to that in a Dowd-Beckwith ring expansion. Without this rearrangement, peroxy radicals derived from MTbuK and DTbuK cannot undergo HO2 elimination to yield a closed-shell unsaturated hydrocarbon coproduct. However, not only are these coproducts observed, but they represent the dominant oxidation channels of these ketones under the conditions of this study. For MTbuK and DTbuK, the rearrangement yields a more stable tertiary radical, which provides the thermodynamic driving force for this reaction. Even in the absence of such a driving force in the oxidation of partially deuterated DEK, the 1,2-acyl group migration is observed. Quantum chemical (CBS-QB3) calculations show the barrier for gas-phase rearrangement to be on the order of 10 kcal mol-1. The MTbuK oxidation experiments also show several minor channels, including β-scission of the initial radicals and cyclic ether formation.

-

Huston,Ungnade

, p. 2885 (1940)

-

Lemcoff,Cunningham

, p. 81,83, 85, 87, 89 (1971)

-

Adkins,Connor

, p. 1095 (1931)

-

-

Claisen

, p. 136 (1896)

-

A convenient deoxygenation fo α,β-epoxy ketones to enones

Dos Santos, Reginaldo B.,Brocksom, Timothy John,Brocksom, Ursula

, p. 745 - 748 (1997)

A new and efficient methodology for the deoxigenation of α,β-epoxy ketones to enones has been developed, using aminoiminomethanesulfinic acid (thioulea dioxide) as the reducing agent under phase transfer conditions. The epoxides of mesityl oxide, isophorane (-)-carvone, (+)-6-methyl-carvone, (+)-6-ethyl-carvone and (-)-myrtenal, were converted into their respectives enones in good to excellent yields.

Pommier,Roubineau

, p. P25 (1969)

-

Kremann,Hoenel

, p. 1469 (1913)

-

In-situ IR Spectroscopy Study of Reactions of C3 Oxygenates on Heteroatom (Sn, Mo, and W) doped BEA Zeolites and the Effect of Co-adsorbed Water

Najmi, Sean,So, Jungseob,Stavitski, Eli,McDermott, William P.,Lyu, Yimeng,Burt, Sam P.,Hermans, Ive,Sholl, David S.,Sievers, Carsten

, p. 445 - 458 (2021)

The reactions of acetone and hydroxyacetone over heteroatom doped BEA zeolites (Sn, Mo, and W) in the presence and absence of H2O vapor are investigated using infrared spectroscopy. Acetone is converted to mesityl oxide over Sn-BEA exclusively. At higher temperatures, larger oxygenates such as phorones, aromatics, and coke form. The presence of co-adsorbed water in Sn-BEA suppresses tautomerization. H2O vapor is also beneficial for minimizing coke formation at high temperatures. Hydroxyacetone is converted into 2-hydroxypropanal over Sn-BEA, exhibiting high affinity to Sn sites up to 400 °C. Sn-BEA catalyzes conversion of hydroxyacetone into the enol in the absence of H2O, but exposure to H2O induces the formation of 2-hydroxypropanal and subsequent conversion to acrolein. The Lewis acid descriptors are used to rationalize the reaction pathways. For the isomerization of hydroxyacetone into 2-hydroxypropanal, the hardness of acid sites influences the reaction and correlates with the overall Lewis acidity of the catalysts, respectively. However, the size of the exchanged metal significantly affects aldol condensation, where keto and enol forms of acetone adsorb to active sites simultaneously.

-

France,Maitland,Tucker

, p. 1739,1741 (1937)

-

Silica Chloride (SiO2-Cl) and Trimethylsilyl Chloride (TMSCl) Promote Facile and Efficient Dehydration of Tertiary Alcohols

Firouzabadi, Habib,Iranpoor, Naser,Hazarkhani, Hassan,Karimi, Babak

, p. 3653 - 3660 (2003)

Silica chloride (SiO2-Cl), as a heterogeneous reagent, has been used for the efficient dehydration of tertiary alcohols under mild reaction conditions. For comparison, we have also used trimethylsilyl chloride (TMSCl) as a homogeneous reagent for this purpose. We have found that silica chloride is a more efficient reagnet than trimethylsilyl chloride for this purpose. Handling of SiO2-Cl is much safer and easier than TMSCl, especially for large-scale operation. The selectivity of the method is also demonstrated by several competitive reactions. Ether formation, rearranged products, and polymerization have not been observed in the reactions.

Condensation and esterification reactions of alkanals, alkanones, and alkanols on TiO2: Elementary steps, site requirements, and synergistic effects of bifunctional strategies

Wang, Shuai,Goulas, Konstantinos,Iglesia, Enrique

, p. 302 - 320 (2016)

Rates and selectivity of TiO2-catalyzed condensation of C3 oxygenates (propanal, acetone) are limited by ubiquitous effects of side reactions, deactivation, and thermodynamic bottlenecks. H2 together with a Cu function, present as physical mixtures with TiO2, circumvents such hurdles by scavenging unsaturated intermediates. They also render alkanols and alkanals/alkanones equivalent as reactants through rapid interconversion, while allowing esterification turnovers by dehydrogenating unstable hemiacetals. Oxygenates form molecules with new C-C and C-O bonds and fewer O-atoms at nearly complete conversions with stable rates and selectivities. Kinetic, isotopic, and theoretical methods showed that rates are limited by α-C-H cleavage from carbonyl reactants to form enolate intermediates, which undergo C-C coupling with another carbonyl species to form α,β-unsaturated oxygenates or with alkanols to form hemiacetals with new C-O bonds, via an intervening H-shift that forms alkoxide-alkanal pairs. Titrations with 2,6-di-tert-butylpyridine, pyridine, CO2, and propanoic acid during catalysis showed that Lewis acid-base site pairs of moderate strength mediate enolate formation steps via concerted interactions with the α-H atom and the enolate moiety at transition states. The resulting site-counts allow rigorous comparisons between theory and experiments and among catalysts on the basis of turnover rates and activation free energies. Theoretical treatments give barriers, kinetic isotope effects, and esterification/condensation ratios in excellent agreement with experiments and confirm the strong effects of reactant substituents at the α-C-atom and of surface structure on reactivity. Surfaces with Ti-O-Ti sites exhibiting intermediate acid-base strength and Ti-O distances, prevalent on anatase but not rutile TiO2, are required for facile α-C-H activation in reactants and reprotonation of the adsorbed intermediates that mediate condensation and esterification turnovers.

Tabushi et al.

, p. 2581 (1969)

Rhodium-catalyzed direct aldol condensation of ketones: A facile synthesis of fused aromatic compounds

Terai, Hiroki,Takaya, Hikaru,Naota, Takeshi

, p. 1705 - 1708 (2006)

Cationic rhodium complex [Cp*Rh(η6-C6H 6)](BF4)2 (1) acts as an efficient catalyst for direct aldol condensation of ketones. The method can be applied to one-pot synthesis of fused aromatic compounds from cyclic ketones via sequential C-C bond formations.

-

Kohn

, p. 779 (1913)

-

Acetone condensation reaction on acid catalysts

Panov,Fripiat

, p. 188 - 197 (1998)

The condensation reaction of acetone on alumina and acid zeolites has been followed by FTIR. Under identical conditions, the reaction rate is faster on alumina, and the condensation goes beyond the formation of mesityl oxide. Zeolites without nonframework aluminum are poor catalysts. On HZSM-5 the reaction is about two orders of magnitude slower than on USY at 105°C. From these data, it appears that Lewis sites, even if they bound acetone less energetically than Bronsted sites, are responsible for the activation of the molecule. On alumina, the reaction would take place between gas phase acetone and acetone adsorbed on Lewis sites. On zeolites with nonframework aluminum and, thus, with Lewis sites, the reaction would involve acetone molecules adsorbed on Bronsted and Lewis sites, the activation occurring on the Lewis site.

Induction of chromosome aberrations in cultured human lymphocytes treated with ethoxyquin

Blaszczyk,Osiecka,Skolimowski

, p. 117 - 128 (2003)

The chromosomal aberration test was employed to investigate the effect in vitro of a known antioxidant and food preservative, ethoxyquin (EQ, 1,2-dihydro-6-ethoxy-2,2,4-trimethylquinoline) on human chromosomes. The studies were undertaken because there are no published in vitro data on genotoxicity of EQ in mammalian cells and there are many reports pointing out that it may be harmful to animals and human beings. Lymphocytes obtained from three healthy donors were incubated with EQ (0.01-0.5mM) both with and without metabolic activation. Stability studies performed by HPLC analysis showed that EQ was stable under the conditions of the lymphocyte cultures. The results of the chromosome aberration assay showed that EQ induces chromosome aberrations: gaps and breaks as well as dicentrics and atypical translocation chromosomes.

ELECTROOXIDATIVE DESULFENYLATION OF MICHAEL-TYPE THIOL ADDUCTS OF α,β-UNSATURATED ESTERS, KETONES, AND NITRILES

Kimura, Makoto,Matsubara, Shinichi,Sawaki, Yasuhiko,Iwamura, Hiizu

, p. 4177 - 4178 (1986)

Michael adducts of ethanethiol with α,β-unsaturated esters ketones,and nitriles are conveniently desulfenylated under neutral conditions by an electrooxidation involving bromonium ion mediation.

Asymmetric catalysis at the mesoscale: Gold nanoclusters embedded in chiral self-assembled monolayer as heterogeneous catalyst for asymmetric reactions

Gross, Elad,Liu, Jack H.,Alayoglu, Selim,Marcus, Matthew A.,Fakra, Sirine C.,Toste, F. Dean,Somorjai, Gabor A.

, p. 3881 - 3886 (2013)

Research to develop highly versatile, chiral, heterogeneous catalysts for asymmetric organic transformations, without quenching the catalytic reactivity, has met with limited success. While chiral supramolecular structures, connected by weak bonds, are highly active for homogeneous asymmetric catalysis, their application in heterogeneous catalysis is rare. In this work, asymmetric catalyst was prepared by encapsulating metallic nanoclusters in chiral self-assembled monolayer (SAM), immobilized on mesoporous SiO2 support. Using olefin cyclopropanation as an example, it was demonstrated that by controlling the SAM properties, asymmetric reactions can be catalyzed by Au clusters embedded in chiral SAM. Up to 50% enantioselectivity with high diastereoselectivity were obtained while employing Au nanoclusters coated with SAM peptides as heterogeneous catalyst for the formation of cyclopropane- containing products. Spectroscopic measurements correlated the improved enantioselectivity with the formation of a hydrogen-bonding network in the chiral SAM. These results demonstrate the synergetic effect of the catalytically active metallic sites and the surrounding chiral SAM for the formation of a mesoscale enantioselective catalyst.

Synthesis of Pyranocyclopentaindolines Representing the Western Sections of Janthitrem B, JBIR-137, and Shearinine G

Fresia, Marvin,Lindel, Thomas

supporting information, (2022/02/05)

The synthesis of the ABCD tetracyclic partial structures of the fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported. The route starts from 5-formylated indoline that is coupled to a dihydropyran moiety, followed by Prins cyclization. A diene was obtained that was oxygenated in a divergent manner. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps and 10 % overall yield. We also share our experience with alternative approaches passing via alkynylated precursors. This includes the gold-catalyzed cycloisomerization of a 6-ethynyl-5-prenylindoline.

Cassis and Green Tea: Spontaneous Release of Natural Aroma Compounds from β-Alkylthioalkanones

B?ttig, Sarah,Bochet, Christian G.,Egger, Timothy,Flachsmann, Felix,Gey, Olga

, (2021/10/19)

In depth headspace analysis of the slow degradation of β-alkylthioalkanones in ambient air led to the discovery of a novel δ-cleavage pathway, by which β-mercaptoketones are released. Since β-mercaptoketones are potent natural aroma compounds occurring in many fruits, herbs and flowers, the discovery of an enzyme-independent molecular precursor for this class of high-impact molecules is of practical importance. Moreover, the formation of β-diketones and aldehydes by concomitant oxidation at the α-sulfur-position enhances the versatility of this class of aroma precursors. A mechanistic model is proposed which suggests that the oxidative degradation occurs through a novel Pummerer-type rearrangement of initially formed persulfoxides.

An active and stable multifunctional catalyst with defective UiO-66 as a support for Pd over the continuous catalytic conversion of acetone and hydrogen

Hu, Yingjie,Mei, Yuxin,Lin, Baining,Du, Xuhong,Xu, Fan,Xie, Huasheng,Wang, Kang,Zhou, Yonghua

, p. 48 - 56 (2021/02/09)

The one-pot synthesis of methyl isobutyl ketone (MIBK) and methyl isobutyl methanol (MIBC) from acetone and hydrogen is a typical cascade reaction comprised of aldol condensation-dehydration-hydrogenation. Pd loss and aggregation during long term operation are typical problems in industrial application. In this paper, an active and stable catalyst was achieved with defective UiO-66 as a support for Pd, which was synthesized with the ratio 15?:?1 of ZrOCl2·8H2O to ZrCl4as Zr-precursors. The resultant Pd catalyst remained active for at least 1000 h with a MIBK + MIBC selectivity of 84.87-93.09% and acetone conversion of 45.26-53.22% in a continuous trickle-bed reactor. Besides the increased Br?nsted acid amount generated by the defect sites was favorable for the activity, the cavity confinement in the UiO-66 (R= 15?:?1) structure also efficiently prevented Pd loss and aggregation during the long term run. The contrast of the characterization of the fresh and used Pd/UiO-66 (R= 15?:?1) indicated that the deactivation of the catalyst was attributed to carbonaceous accumulation on the catalyst surface, which could be easily regenerated by calcination. This work supplied a new alternative for the design and utilization of industrial catalysts for MIBK and MIBC synthesis.

Method for preparing triacetone amine

-

Paragraph 0133-0144, (2020/07/05)

An improved method is used for preparing triacetone amine while recycling the by-products. This involves treating the crude product from triacetone amine preparation, which leads to an increase in the content of compounds which react readily with ammonia. This method enables efficient recycling of the by-products formed in the synthesis of triacetone amine.

Process route upstream and downstream products

Process route

1-isobutenylcyclopropanol
73680-09-8

1-isobutenylcyclopropanol

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

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

5-methyl-4-hexen-3-one
13905-10-7

5-methyl-4-hexen-3-one

5-hydroxy-5-methylhexan-3-one
59356-91-1

5-hydroxy-5-methylhexan-3-one

Conditions
Conditions Yield
With perchloric acid; In water; acetone; for 11h; Product distribution; Heating;
12%
acetone
67-64-1

acetone

butanone
78-93-3

butanone

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

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

5-methyl-4-hexen-3-one
13905-10-7

5-methyl-4-hexen-3-one

Conditions
Conditions Yield
With barium dihydroxide; bei 30 Tage langem Kochen folgendem Destillieren mit Jod;
acetone
67-64-1

acetone

butanone
78-93-3

butanone

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

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

5-methyl-4-hexen-3-one
13905-10-7

5-methyl-4-hexen-3-one

Conditions
Conditions Yield
folgender Destillation unter Zusatz von Jod;
niobium pentachloride
10026-12-7

niobium pentachloride

acetone
67-64-1

acetone

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

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

niobium(V) oxide chloride
13597-20-1

niobium(V) oxide chloride

Conditions
Conditions Yield
In acetone; addn. of NbCl5 to waterfree acetone, pptn. after few days;;
2%
acetone
67-64-1

acetone

2-methylfuran
534-22-5

2-methylfuran

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

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

2-hexen-4-yne
14092-20-7

2-hexen-4-yne

2-methyl-1-penten-3-yne
926-55-6

2-methyl-1-penten-3-yne

4-methylpent-4-en-2-one
3744-02-3

4-methylpent-4-en-2-one

prop-1-yne
74-99-7

prop-1-yne

Conditions
Conditions Yield
With silica gel; In water; at 594 - 612 ℃; for 1h; under 750.075 Torr; Reagent/catalyst; Inert atmosphere;
4-methyl-4-(toluene-4-sulfonyl)-pentan-2-one
33895-88-4

4-methyl-4-(toluene-4-sulfonyl)-pentan-2-one

p-toluene sulfinic acid
536-57-2

p-toluene sulfinic acid

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

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

Conditions
Conditions Yield
4-(4-chloro-anilino)-4-methyl-pentan-2-one
88187-87-5

4-(4-chloro-anilino)-4-methyl-pentan-2-one

acetic anhydride
108-24-7

acetic anhydride

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

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

N-(4-chlorophenyl)acetamide
539-03-7

N-(4-chlorophenyl)acetamide

Conditions
Conditions Yield
acetone
67-64-1

acetone

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

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

phorone
504-20-1

phorone

4-Hydroxy-4-methyl-2-pentanone
123-42-2

4-Hydroxy-4-methyl-2-pentanone

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

1,3,5-trimethyl-benzene

Conditions
Conditions Yield
With MgO/ZrO2 mixed oxides; at 449.84 ℃;
acetone
67-64-1

acetone

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

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

phorone
504-20-1

phorone

4-Hydroxy-4-methyl-2-pentanone
123-42-2

4-Hydroxy-4-methyl-2-pentanone

Conditions
Conditions Yield
With titanium tetrachloride; NCNMe2; In benzene; at 25 ℃;
8%
2%
82%
With sodium hydroxide; In benzene; at 40 ℃; Mechanism; Kinetics; benzyltriethylammonium chloride presence;
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In benzene; at 40 ℃; reaction order, effect of concentration on the initial rate;
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In benzene; at 40 ℃; Mechanism; effect concentrations, initial rate;
With MgO/ZrO2 mixed oxides; at 249.84 ℃;
acetone
67-64-1

acetone

3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

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

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

phorone
504-20-1

phorone

4-Hydroxy-4-methyl-2-pentanone
123-42-2

4-Hydroxy-4-methyl-2-pentanone

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

1,3,5-trimethyl-benzene

Conditions
Conditions Yield
With MgO/ZrO2 mixed oxides; at 449.84 ℃;

Global suppliers and manufacturers

Global( 72) Suppliers
  • Company Name
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  • Contact Tel
  • Emails
  • Main Products
  • Country
  • Simagchem Corporation
  • Business Type:Manufacturers
  • Contact Tel:+86-592-2680277
  • Emails:sale@simagchem.com
  • Main Products:110
  • Country:China (Mainland)
  • Chemwill Asia Co., Ltd.
  • Business Type:Manufacturers
  • Contact Tel:021-51086038
  • Emails:sales@chemwill.com
  • Main Products:55
  • Country:China (Mainland)
  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Kono Chem Co.,Ltd
  • Business Type:Other
  • Contact Tel:86-29-86107037-8015
  • Emails:info@konochemical.com
  • Main Products:82
  • Country:China (Mainland)
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